Journal name: Journal of natural products / Publication year rev: 7981-2019 / Text availability: Citation in PubAg

1. (+)- and (−)-Alternarilactone A: Enantiomers with a Diepoxy-Cage-like Scaffold from an Endophytic Alternaria sp.

Author:: Jian-Wei Tang; Hou-Chao Xu; Wei-Guang Wang; Kun Hu; Yuan-Fei Zhou; Rong Chen; Xiao-Nian Li; Xue Du; Han-Dong Sun; Pema-Tenzin Puno
Source:: Journal of natural products 2019 v.82 no.4 pp. 735-740
ISSN:: 1520-6025
Subject:: Alternaria; X-ray diffraction; enantiomers; endophytes; fungi; moieties; nuclear magnetic resonance spectroscopy; probability analysis; quantum mechanics; risk
Abstract:: ... The enantiomers (+)- and (−)-alternarilactone A (1), the first examples of dibenzo-α-pyrones bearing a diepoxy-cage-like moiety, were isolated from the endophytic fungus Alternaria sp. hh930. The deficiency in ¹H–¹H COSY and HMBC correlations caused by the highly oxidized caged system of 1 and the deceptive and ambiguous signals such as “W” couplings in NMR data increased the risk of structure mis ...
DOI:: 10.1021/acs.jnatprod.8b00571
: https://doi.org/10.1021/acs.jnatprod.8b00571

2. (−)-Epigallocatechin 3-O-Gallate as a New Approach for the Treatment of Visceral Leishmaniasis

Author:: Job D.F. Inacio; Myslene S. Fonseca; Elmo E. Almeida-Amaral
Source:: Journal of natural products 2019 v.82 no.9 pp. 2664-2667
ISSN:: 1520-6025
Subject:: Leishmania infantum; adverse effects; median effective concentration; mice; oral administration; visceral leishmaniasis
Abstract:: ... In addition to generating side effects and resistance, treatment for visceral leishmaniasis remains mostly ineffective and expensive, and it has a long duration. Thus, natural products are an important alternative for treatment of the disease. In this study, we demonstrate the in vitro and in vivo activity of (−)-epigallocatechin 3-O-gallate (1) against Leishmania infantum. Compound 1 reduced the ...
DOI:: 10.1021/acs.jnatprod.9b00632
: https://doi.org/10.1021/acs.jnatprod.9b00632

3. 11-Aminostrychnine and N-(Strychnine-11-yl)propionamide: Synthesis, Configuration, and Pharmacological Evaluation at Glycine Receptors

Author:: Darius P. Zlotos; Amal M. Y. Mohsen; Yasmine M. Mandour; Mohamed A. Marzouk; Ulrike Breitinger; Carmen Villmann; Hans-Georg Breitinger; Christoph Sotriffer; Anders A. Jensen; Ulrike Holzgrabe
Source:: Journal of natural products 2019 v.82 no.8 pp. 2332-2336
ISSN:: 1520-6025
Subject:: antagonists; binding sites; glycine (amino acid); glycine receptors; strychnine
Abstract:: ... (11S)-11-Aminostrychnine (1) and N-[(11S)-strychnine-11-yl]propionamide (2) were synthesized and characterized as antagonists of homomeric α1 and heteromeric α1β glycine receptors in a functional fluorescence-based assay and a patch-clamp assay and in radioligand binding studies. The absolute configuration at C-11 of 1 was determined based on vicinal coupling constants and NOESY data. Docking expe ...
DOI:: 10.1021/acs.jnatprod.9b00180
: https://doi.org/10.1021/acs.jnatprod.9b00180

4. 17-nor-Cephalotane-Type Diterpenoids from Cephalotaxus fortunei

Author:: Zhan-Peng Ge; Hong-Chun Liu; Guo-Cai Wang; Qun-Fang Liu; Cheng-Hui Xu; Jian Ding; Yao-Yue Fan; Jian-Min Yue
Source:: Journal of natural products 2019 v.82 no.6 pp. 1565-1575
ISSN:: 1520-6025
Subject:: Cephalotaxus fortunei; X-ray diffraction; cytotoxicity; diterpenoids; moieties; seeds; structure-activity relationships
Abstract:: ... Seventeen new 17-nor-cephalotane-type diterpenoids, fortalpinoids A–Q (1–17), were isolated from the seeds of Cephalotaxus fortunei var. alpine. Compound 12 represents the first 17-nor-cephalotane-type diterpenoid featuring an 8-oxabicyclo[3.2.1]oct-2-ene moiety. The absolute configuration of fortunolide A (18) was determined for the first time, and the structure of cephinoid Q was revised to 14-e ...
DOI:: 10.1021/acs.jnatprod.9b00059
: https://doi.org/10.1021/acs.jnatprod.9b00059

5. 2-(Tetrahydrofuran-2-yl)acetic Acid and Ester Derivatives as Long-Range Pollinator Attractants in the Sexually Deceptive Orchid Cryptostylis ovata

Author:: Björn Bohman; Alyssa M. Weinstein; Ryan D. Phillips; Rod Peakall; Gavin R. Flematti
Source:: Journal of natural products 2019 v.82 no.5 pp. 1107-1113
ISSN:: 1520-6025
Subject:: Orchidaceae; acetic acid; attractants; bioassays; ejaculation; enantiomers; females; flowers; high performance liquid chromatography; insects; males; pollination; pollinators; semiochemicals; solvents
Abstract:: ... Sexually deceptive orchids achieve pollination by luring male insects to flowers through chemical and sometimes visual mimicry of females. An extreme example of this deception occurs in Cryptostylis, one of only two genera where sexual deception is known to induce pollinator ejaculation. In the present study, bioassay-guided fractionations of Cryptostylis solvent extracts in combination with field ...
DOI:: 10.1021/acs.jnatprod.8b00772
: https://doi.org/10.1021/acs.jnatprod.8b00772

6. A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea

Author:: Soon-Kit Wong; Suet-Pick Wong; Kae-Shin Sim; Siew-Huah Lim; Yun-Yee Low; Toh-Seok Kam
Source:: Journal of natural products 2019 v.82 no.7 pp. 1902-1907
ISSN:: 1520-6025
Subject:: X-ray diffraction; alkaloids; bark; biochemical pathways; copper; cytotoxicity; human cell lines; humans; inhibitory concentration 50; monoterpenoids; neoplasm cells; nuclear magnetic resonance spectroscopy; oxygen
Abstract:: ... Three new alkaloids were isolated from the bark extract of the Malayan Kopsia arborea, viz., arbophyllidine (1), an unusual pentacyclic, monoterpenoid indole characterized by an absence of oxygen atoms and incorporating a new carbon–nitrogen skeleton, and arbophyllinines A (2) and B (3), two pentacyclic corynanthean alkaloids incorporating a hydroxyethyl-substituted tetrahydrofuranone ring. The st ...
DOI:: 10.1021/acs.jnatprod.9b00255
: https://doi.org/10.1021/acs.jnatprod.9b00255

7. A Near-Complete Series of Four Atropisomeric Jozimine A₂-Type Naphthylisoquinoline Dimers with Antiplasmodial and Cytotoxic Activities and Related Alkaloids from Ancistrocladus abbreviatus

Author:: Shaimaa Fayez; Jun Li; Doris Feineis; Laurent Aké Assi; Marcel Kaiser; Reto Brun; Mohamed A. Anany; Harald Wajant; Gerhard Bringmann
Source:: Journal of natural products 2019 v.82 no.11 pp. 3033-3046
ISSN:: 1520-6025
Subject:: Ancistrocladus; alkaloids; antimalarials; antiplasmodial properties; colorectal neoplasms; cytotoxicity; fibrosarcoma; human diseases; inhibitory concentration 50; moieties; myeloma; naphthalene; neoplasm cells; optical isomerism; oxygen; shrubs
Abstract:: ... Three new naphthylisoquinoline dimers, jozibrevines A–C (1a–c), were isolated from the West African shrub Ancistrocladus abbreviatus, along with the known dimer jozimine A₂ (1d). The two molecular moieties of 1a–d are coupled via the sterically constrained 3′,3″-positions of their two naphthalene units, so that the central biaryl linkage is rotationally hindered. With the two outer axes also being ...
DOI:: 10.1021/acs.jnatprod.9b00589
: https://doi.org/10.1021/acs.jnatprod.9b00589

8. A Systematic Cheminformatics Analysis of Functional Groups Occurring in Natural Products

Author:: Peter Ertl; Tim Schuhmann
Source:: Journal of natural products 2019 v.82 no.5 pp. 1258-1263
ISSN:: 1520-6025
Subject:: chemoinformatics; derivatization; moieties
Abstract:: ... The two most striking features that discriminate natural products from synthetic molecules are their characteristic scaffolds and unique functional groups (FGs). In this study we systematically investigate the distribution of FGs in natural products from a cheminformatics perspective by comparing FG frequencies in natural products with those found in average synthetic molecules. We thereby aim for ...
DOI:: 10.1021/acs.jnatprod.8b01022
: https://doi.org/10.1021/acs.jnatprod.8b01022

9. Absolute Configuration and Biological Activities of Meroterpenoids from an Endophytic Fungus of Lycium barbarum

Author:: Yi Long; Ting Tang; Li-Ying Wang; Bin He; Kun Gao
Source:: Journal of natural products 2019 v.82 no.8 pp. 2229-2237
ISSN:: 1520-6025
Subject:: Bipolaris; Lycium barbarum; X-ray diffraction; benzoquinones; biosynthesis; cytotoxicity; endophytes; fungi; hydroquinone; inhibitory concentration 50; meroterpenoids; moieties; spectral analysis
Abstract:: ... Eleven new meroterpenoids, bipolahydroquinones A–C (1–3), cochlioquinones I–N (4–8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compou ...
DOI:: 10.1021/acs.jnatprod.9b00288
: https://doi.org/10.1021/acs.jnatprod.9b00288

10. Absolute Configuration of Alkaloids from Uncaria longiflora through Experimental and Computational Approaches

Author:: Fatimah Salim; Yusri Mohd Yunus; El Hassane Anouar; Khalijah Awang; Moses Langat; Geoffrey A. Cordell; Rohaya Ahmad
Source:: Journal of natural products 2019 v.82 no.11 pp. 2933-2940
ISSN:: 1520-6025
Subject:: Uncaria; alkaloids; biochemical pathways; density functional theory; leaves; quantum mechanics
Abstract:: ... The structure elucidation of three new alkaloids named isoformosaninol (1), formosaninol (2), and longiflorine (3), isolated from the leaves of Uncaria longiflora var. pteropoda (Miq.) Ridsdale, along with their biosynthetic pathways are discussed. Their absolute structures were determined through a combination of physical data interpretation and quantum chemical calculations using the time-depend ...
DOI:: 10.1021/acs.jnatprod.8b00380
: https://doi.org/10.1021/acs.jnatprod.8b00380

11. Absolute Configuration of Bioactive Azaphilones from the Marine-Derived Fungus Pleosporales sp. CF09-1

Author:: Fei Cao; Zhi-Hui Meng; Xing Mu; Yu-Fei Yue; Hua-Jie Zhu
Source:: Journal of natural products 2019 v.82 no.2 pp. 386-392
ISSN:: 1520-6025
Subject:: Alternaria brassicicola; Botryosphaeria dothidea; Fusarium oxysporum; Vibrio anguillarum; Vibrio parahaemolyticus; antifungal properties; circular dichroism spectroscopy; fungi; ketoconazole; minimum inhibitory concentration; nuclear magnetic resonance spectroscopy
Abstract:: ... Investigation of the marine-derived fungus Pleosporales sp. CF09-1 cultured in modified PDB medium led to the isolation of six new azaphilone derivatives, pleosporalones B and C (1 and 2) and pleosporalones E–H (4–7), and one known analogue (3). The absolute configurations of C-2′ and C-3′ in 3 were assigned by a vibrational circular dichroism method. The C-11 relative configurations for the pair ...
DOI:: 10.1021/acs.jnatprod.8b01030
: https://doi.org/10.1021/acs.jnatprod.8b01030

12. Access to Natural Valparanes and Daucanes: Enantioselective Synthesis of (−)-Valpara-2,15-diene and (+)-Isodaucene

Author:: José F. Quílez del Moral; Álvaro Pérez; María del Mar Herrador; Alejandro F. Barrero
Source:: Journal of natural products 2019 v.82 no.1 pp. 9-15
ISSN:: 1520-6025
Subject:: acetates; cyclization reactions; diterpenoids; enantioselective synthesis; moieties; sesquiterpenoids; titanium
Abstract:: ... The first total synthesis of a natural diterpene valparane, (−)-valpara-2,15-diene (1), has been achieved from all-trans-geranylgeraniol (9), a natural renewable compound. The key steps involve a Ti(III)-mediated radical cyclization of the chiral monoepoxypolyene (14R,15R)-14,15-epoxy,16-tert-butyldimethylsilyloxygeranyllinalyl acetate (8) to give the 6,6,7-tricyclic intermediate 7 with stereocont ...
DOI:: 10.1021/acs.jnatprod.8b00129
: https://doi.org/10.1021/acs.jnatprod.8b00129

13. Acidiphilamides A–E, Modified Peptides as Autophagy Inhibitors from an Acidophilic Actinobacterium, Streptacidiphilus rugosus

Author:: Sunghoon Hwang; Yejin Yun; Won Hoon Choi; Seung Bum Kim; Jongheon Shin; Min Jae Lee; Dong-Chan Oh
Source:: Journal of natural products 2019 v.82 no.2 pp. 341-348
ISSN:: 1520-6025
Subject:: Actinobacteria; autophagy; derivatization; forest soils; human cell lines; isothiocyanates; nuclear magnetic resonance spectroscopy; proteasome endopeptidase complex; secondary metabolites; spectral analysis; tripeptides
Abstract:: ... Five new tripeptides, acidiphilamides A–E (1–5), were discovered along with two previously reported compounds, l-isoleucinamide (6) and l-valinamide (7), from Streptacidiphilus rugosus AM-16, an acidophilic actinobacterial strain isolated from acidic forest soil. The structures of 1–5 were elucidated as modified tripeptides bearing phenylalaninol or methioninol fragments with C₃–C₅ acyl chains bas ...
DOI:: 10.1021/acs.jnatprod.8b00828
: https://doi.org/10.1021/acs.jnatprod.8b00828

14. Acrotrione: An Oxidized Xanthene from the Roots of Acronychia pubescens

Author:: Luke P. Robertson; Leonardo Lucantoni; Sandra Duffy; Vicky M. Avery; Anthony R. Carroll
Source:: Journal of natural products 2019 v.82 no.4 pp. 1019-1023
ISSN:: 1520-6025
Subject:: Acronychia; Plasmodium falciparum; acetophenones; antiplasmodial properties; inhibitory concentration 50; methanol; moieties; nuclear magnetic resonance spectroscopy; oxidation; roots; xanthenes
Abstract:: ... A new oxidized xanthene, acrotrione (1), and two known acetophenones (2 and 3) were isolated from a methanol extract of the roots of Acronychia pubescens. The structure of 1 was elucidated on the basis of its (+)-HRESIMS, 2D NMR, and ECD data. Acritrione (1) contains an unusual oxidized furo[2,3-c]xanthene moiety that has not been previously reported. Moderate antiplasmodial activity for these nat ...
DOI:: 10.1021/acs.jnatprod.8b00956
: https://doi.org/10.1021/acs.jnatprod.8b00956

15. Acylated Lignans Isolated from Brachanthemum gobicum and Their Trypanocidal Activity

Author:: Batsukh Odonbayar; Toshihiro Murata; Keisuke Suganuma; Yoshinobu Ishikawa; Buyanmandakh Buyankhishig; Javzan Batkhuu; Kenroh Sasaki
Source:: Journal of natural products 2019 v.82 no.4 pp. 774-784
ISSN:: 1520-6025
Subject:: Asteraceae; Trypanosoma congolense; aerial parts; animals; bovine trypanosomiasis; enantiomers; high performance liquid chromatography; lignans; nuclear magnetic resonance spectroscopy
Abstract:: ... Eight isovaleryllignans (1–4 and 8–11), three isovalerylphenylpropanoids (5–7), three known lignans (12–14), and four known compounds were isolated from an extract of the aerial part of Brachanthemum gobicum. The structures of the isolated compounds were elucidated based on NMR and MS data analyses. The enantiomers of compounds 1–3, 5, 8, and 9 were isolated using chiral-phase HPLC, and the absolu ...
DOI:: 10.1021/acs.jnatprod.8b00670
: https://doi.org/10.1021/acs.jnatprod.8b00670

16. Adiponectin-Secretion-Promoting Phenylethylchromones from the Agarwood of Aquilaria malaccensis

Author:: Sungjin Ahn; Chi Thanh Ma; Jung Min Choi; Seungchan An; Moonyoung Lee; Thi Hong Van Le; Jeong Joo Pyo; Joochang Lee; Min Sik Choi; Sung Won Kwon; Jeong Hill Park; Minsoo Noh
Source:: Journal of natural products 2019 v.82 no.2 pp. 259-264
ISSN:: 1520-6025
Subject:: Aquilaria malaccensis; adipogenesis; adiponectin; agonists; atherosclerosis; bone marrow; diabetes; human diseases; humans; mesenchymal stromal cells; neoplasms; obesity; secretion; therapeutics
Abstract:: ... The therapeutic potential of adiponectin regulation has received interest because of its association with diverse human disease conditions, such as diabetes, obesity, atherosclerosis, and cancer. Phenylethylchromone derivatives from Aquilaria malaccensis-derived agarwood promoted adiponectin secretion during adipogenesis in human bone marrow mesenchymal stem cells, and 5,6-dihydroxy-2-(2-phenyleth ...
DOI:: 10.1021/acs.jnatprod.8b00635
: https://doi.org/10.1021/acs.jnatprod.8b00635

17. Albanitriles A–G: Antiprotozoal Polyacetylene Nitriles from a Mycale Marine Sponge

Author:: Samuele Sala; Jane Fromont; Oliver Gomez; Daniel Vuong; Ernest Lacey; Gavin R. Flematti
Source:: Journal of natural products 2019 v.82 no.12 pp. 3450-3455
ISSN:: 1520-6025
Subject:: Giardia lamblia; Mycale; mass spectrometry; metronidazole; nitriles; nuclear magnetic resonance spectroscopy; polyacetylenes; Western Australia
Abstract:: ... Seven new nitrile-bearing polyacetylenes, named albanitriles A–G, were isolated from a marine sponge of the Mycale genus (Order: Poecilosclerida, Family: Mycalidae) collected near Albany, Western Australia. Structural elucidation was achieved using a combination of high-resolution mass spectrometry and ultraviolet/visible, infrared, and nuclear magnetic resonance spectroscopy. The compounds were f ...
DOI:: 10.1021/acs.jnatprod.9b00840
: https://doi.org/10.1021/acs.jnatprod.9b00840

18. Alkaloids Purified from Aristotelia chilensis Inhibit the Human α3β4 Nicotinic Acetylcholine Receptor with Higher Potencies Compared with the Human α4β2 and α7 Subtypes

Author:: Hugo R. Arias; Marcelo O. Ortells; Dominik Feuerbach; Viviana Burgos; Cristian Paz
Source:: Journal of natural products 2019 v.82 no.7 pp. 1953-1960
ISSN:: 1520-6025
Subject:: Aristotelia chilensis; alkaloids; calcium; computer simulation; humans; inhibitory concentration 50; ion channels; leaves; ligands; lipophilicity; medicinal properties; nicotinic receptors; nuclear magnetic resonance spectroscopy; structure-activity relationships; trees
Abstract:: ... The alkaloids aristoteline (1), aristoquinoline (2), and aristone (3) were purified from the leaves of the Maqui tree Aristotelia chilensis and chemically characterized by NMR spectroscopy. The pharmacological activity of these natural compounds was evaluated on human (h) α3β4, α4β2, and α7 nicotinic acetylcholine receptors (AChRs) by Ca²⁺ influx measurements. The results suggest that these alkalo ...
DOI:: 10.1021/acs.jnatprod.9b00314
: https://doi.org/10.1021/acs.jnatprod.9b00314

19. Alkaloids from the Branches and Leaves of Elaeocarpus angustifolius

Author:: Wei Hong; Yu Zhang; Jun Yang; Meng-Yuan Xia; Ji-Feng Luo; Xiao-Nian Li; Yue-Hu Wang; Jun-Song Wang
Source:: Journal of natural products 2019 v.82 no.12 pp. 3221-3226
ISSN:: 1520-6025
Subject:: Elaeocarpus sphaericus; alkaloids; branches; cholinesterase; circular dichroism spectroscopy; enzyme inhibition; inhibitory concentration 50; leaves; nuclear magnetic resonance spectroscopy
Abstract:: ... Nine new alkaloids, (+)-1, (−)-1, 2, (+)-3, (−)-3, and 4–7, along with five known compounds (8–12), were obtained from the branches and leaves of Elaeocarpus angustifolius. The alkaloids were structurally characterized by NMR and MS data. The absolute configurations of (+)-1, (−)-1, (+)-3, and (−)-3 were determined by comparing their experimental and computed electronic circular dichroism spectra. ...
DOI:: 10.1021/acs.jnatprod.8b01027
: https://doi.org/10.1021/acs.jnatprod.8b01027

20. Alopecuroides A–E, Matrine-Type Alkaloid Dimers from the Aerial Parts of Sophora alopecuroides

Author:: Chun-Lin Fan; Yu-Bo Zhang; Ye Chen; Pei Xie; Guo-Cai Wang; Hai-Yan Tian; Yao-Lan Li; Xiao-Jun Huang; Xiao-Qi Zhang; Zhi-Yong Li; Jun-Shan Liu; Wen-Cai Ye; Wei-Min Chen
Source:: Journal of natural products 2019 v.82 no.12 pp. 3227-3232
ISSN:: 1520-6025
Subject:: Sophora alopecuroides; X-ray diffraction; aerial parts; alkaloids; anti-inflammatory activity; epoxides; moieties; spectroscopy
Abstract:: ... Five new matrine-type alkaloid dimers, alopecuroides A–E, were isolated from the aerial parts of Sophora alopecuroides. Alopecuroides A and B represent the first dimeric matrine-type alkaloids possessing a cyano group and an epoxy moiety. Alopecuroides C and D are dimeric matrine-type alkaloids connected via C-2–C-9′ and C-10–C-3′ bonds, respectively. The chemical structures of alopecuroides A–E w ...
DOI:: 10.1021/acs.jnatprod.8b01081
: https://doi.org/10.1021/acs.jnatprod.8b01081

21. Alternatone A, an Unusual Perylenequinone-Related Compound from a Soft-Coral-Derived Strain of the Fungus Alternaria alternata

Author:: Dong-Lin Zhao; Fei Cao; Chao-Yi Wang; Lu-Jia Yang; Ting Shi; Kai-Ling Wang; Chang-Lun Shao; Chang-Yun Wang
Source:: Journal of natural products 2019 v.82 no.11 pp. 3201-3204
ISSN:: 1520-6025
Subject:: Alternaria alternata; X-ray diffraction; biochemical pathways; circular dichroism spectroscopy; cytotoxicity; fungi; human cell lines; inhibitory concentration 50; quinones; spectral analysis
Abstract:: ... A novel perylenequinone-related compound, alternatone A (1), with an unprecedented tricyclo[6.3.1.0²,⁷] dodecane skeleton, together with three known perylenequinones, altertoxin I (2), stemphyperylenol (3), and alterperylenol (4), was isolated from the soft-coral-derived fungus Alternaria alternata L3111′. Their structures including absolute configurations were elucidated on the basis of comprehen ...
DOI:: 10.1021/acs.jnatprod.9b00905
: https://doi.org/10.1021/acs.jnatprod.9b00905

22. Ambiguity of NRPS Structure Predictions: Four Bidentate Chelating Groups in the Siderophore Pacifibactin

Author:: Clifford D. Hardy; Alison Butler
Source:: Journal of natural products 2019 v.82 no.4 pp. 990-997
ISSN:: 1520-6025
Subject:: Alcanivorax; bioinformatics; biosynthesis; chelation; enzymes; gallium; genome mining; iron; ligands; multigene family; nuclear magnetic resonance spectroscopy; peptides; photochemical reactions; prediction; siderophores; titration
Abstract:: ... Identified through a bioinformatics approach, a nonribosomal peptide synthetase gene cluster in Alcanivorax pacificus encodes the biosynthesis of the new siderophore pacifibactin. The structure of pacifibactin differs markedly from the bioinformatic prediction and contains four bidentate metal chelation sites, atypical for siderophores. Genome mining and structural characterization of pacifibactin ...
DOI:: 10.1021/acs.jnatprod.8b01073
: https://doi.org/10.1021/acs.jnatprod.8b01073

23. Amides and Flavonoids from the Fruit and Leaf Extracts of Melodorum siamensis

Author:: Wuttichai Jaidee; Raymond J. Andersen; Miguel A. G. Chavez; Yan A. Wang; Brian O. Patrick; Stephen G. Pyne; Chatchai Muanprasat; Suparerk Borwornpinyo; Surat Laphookhieo
Source:: Journal of natural products 2019 v.82 no.2 pp. 283-292
ISSN:: 1520-6025
Subject:: X-ray diffraction; amides; cell lines; chalcones; flavanones; fruits; inhibitory concentration 50; islets of Langerhans; leaf extracts; nuclear magnetic resonance spectroscopy; transcription factor NF-kappa B
Abstract:: ... Four new chalcones (1, 10, 13, and 14), a new flavanone, (9), a new amide (8), and 19 known compounds were acquired from Melodorum siamensis. The structures were established by NMR and MS data analyses. Compounds 1 (er 1.4:1) and 2 (er 1.1:1) were scalemic and were resolved to yield (−)-1 and (+)-1 and (−)-2 and (+)-2, respectively. The absolute configurations of these compounds were determined fr ...
DOI:: 10.1021/acs.jnatprod.8b00696
: https://doi.org/10.1021/acs.jnatprod.8b00696

24. An Acetylenic Lipid from the New Zealand Ascidian Pseudodistoma cereum: Exemplification of an Improved Workflow for Determination of Absolute Configuration of Long-Chain 2-Amino-3-alkanols

Author:: A. Norrie Pearce; Cameron A. E. Hill; Michael J. Page; Robert A. Keyzers; Brent R. Copp
Source:: Journal of natural products 2019 v.82 no.8 pp. 2291-2298
ISSN:: 1520-6025
Subject:: circular dichroism spectroscopy; lipids; New Zealand
Abstract:: ... An acetylenic 2-amino-3-alcohol, distaminolyne B (2), isolated from the New Zealand ascidian Pseudodistoma cereum, is reported. The isolation and structure elucidation of 2 and assignment of 2S,3S absolute configuration (AC) using the exciton coupled circular dichroism technique are described. Using a methodologically facile workflow, the same AC was also established by analysis of specific rotati ...
DOI:: 10.1021/acs.jnatprod.9b00504
: https://doi.org/10.1021/acs.jnatprod.9b00504

25. An Effective Strategy for Identification of Highly Unstable Bacillaenes

Author:: Huayue Li; Xiao Han; Jun Zhang; Yujing Dong; Shanshan Xu; Yilei Bao; Chao Chen; Yingang Feng; Qiu Cui; Wenli Li
Source:: Journal of natural products 2019 v.82 no.12 pp. 3340-3346
ISSN:: 1520-6025
Subject:: antibacterial properties; genomics; glycosylation; metabolomics; multiple drug resistance; nuclear magnetic resonance spectroscopy
Abstract:: ... Exploration of unstable compounds is a rarely explored area of natural product research. We describe the integration of genomic and metabolomic analyses with bioassay-guided compound mining to effectively explore unstable bacillaenes. New bacillaene structures (2, 4, and 5) were identified from compound mixtures using the DANS-SVI (differential analysis of 2D NMR spectrum–single spectrum with vari ...
DOI:: 10.1021/acs.jnatprod.9b00609
: https://doi.org/10.1021/acs.jnatprod.9b00609

26. An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray

Author:: Lin Du; Charissa Munteanu; Jarrod B. King; Doug E. Frantz; Robert H. Cichewicz
Source:: Journal of natural products 2019 v.82 no.7 pp. 1989-1999
ISSN:: 1520-6025
Subject:: Lewis acids; anal glands; chemical defenses; clothing; deodorization; eye irritation; fungi; humans; ingredients; metabolites; neutralization; odors; people; pets; predators; secretion; skunks; thiols
Abstract:: ... The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans and their pets. The extremely low thresholds for detection of the organosulfur metabolites make efforts to “de-skunk” people, animals, and clothin ...
DOI:: 10.1021/acs.jnatprod.9b00415
: https://doi.org/10.1021/acs.jnatprod.9b00415

27. An Orbitide from Ratibida columnifera Seed Containing 16 Amino Acid Residues

Author:: Mark F. Fisher; Colton D. Payne; K. Johan Rosengren; Joshua S. Mylne
Source:: Journal of natural products 2019 v.82 no.8 pp. 2152-2158
ISSN:: 1520-6025
Subject:: Ratibida; amino acids; bioactive properties; cyclic peptides; disulfide bonds; drugs; nuclear magnetic resonance spectroscopy
Abstract:: ... Cyclic peptides are abundant in plants and have attracted interest due to their bioactivity and potential as drug scaffolds. Orbitides are head-to-tail cyclic peptides that are ribosomally synthesized, post-translationally modified, and lack disulfide bonds. All known orbitides contain 5−12 amino acid residues. Here we describe PLP-53, a novel orbitide from the seed of Ratibida columnifera. PLP-53 ...
DOI:: 10.1021/acs.jnatprod.9b00111
: https://doi.org/10.1021/acs.jnatprod.9b00111

28. Anacolosins A–F and Corymbulosins X and Y, Clerodane Diterpenes from Anacolosa clarkii Exhibiting Cytotoxicity toward Pediatric Cancer Cell Lines

Author:: Shengxin Cai; April L. Risinger; Cora L. Petersen; Tanja Grkovic; Barry R. O’Keefe; Susan L. Mooberry; Robert H. Cichewicz
Source:: Journal of natural products 2019 v.82 no.4 pp. 928-936
ISSN:: 1520-6025
Subject:: cell lines; circular dichroism spectroscopy; cytotoxicity; diterpenoids; esterification; fractionation; high performance liquid chromatography; moieties; neoplasm cells; nuclear magnetic resonance spectroscopy; sarcoma
Abstract:: ... An extract of the plant Anacolosa clarkii was obtained from the NCI Natural Products Repository, and it showed cytotoxic activity toward several types of pediatric solid tumor cell lines. Bioassay-guided fractionation led to the purification of eight new clerodane diterpenes [anacolosins A–F (1–6) and corymbulosins X and Y (7 and 8)] and two known compounds (9 and 10) that contained an isozuelanin ...
DOI:: 10.1021/acs.jnatprod.8b01015
: https://doi.org/10.1021/acs.jnatprod.8b01015

29. Antcamphorols A–K, Cytotoxic and ROS Scavenging Triterpenoids from Antrodia camphorata

Author:: Bin Li; Yi Kuang; Jun-Bin He; Rui Tang; Lu-Lu Xu; Chung-Hang Leung; Dik-Lung Ma; Xue Qiao; Min Ye
Source:: Journal of natural products 2019 v.83 no.1 pp. 45-54
ISSN:: 1520-6025
Subject:: Taiwanofungus camphoratus; X-ray diffraction; cytotoxicity; human cell lines; human diseases; inhibitory concentration 50; medicinal fungi; moieties; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; triterpenoids
Abstract:: ... Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A–K (1–11), together with 10 known triterpenoids, 12–21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C₃₁ lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21–O–C-24 tetrahydropyran ring at C-17. Compounds 2–11 are ergostane-t ...
DOI:: 10.1021/acs.jnatprod.9b00580
: https://doi.org/10.1021/acs.jnatprod.9b00580

30. Anti-Lymphangiogenic Alkaloids from the Zoanthid Zoanthus vietnamensis Collected in Taiwan

Author:: Shu-Rong Chen; Shih-Wei Wang; Fang-Rong Chang; Yuan-Bin Cheng
Source:: Journal of natural products 2019 v.82 no.10 pp. 2790-2799
ISSN:: 1520-6025
Subject:: X-ray diffraction; alkaloids; cell growth; endothelial cells; human cell lines; nuclear magnetic resonance spectroscopy; secondary metabolites; spectral analysis; structure-activity relationships; Taiwan
Abstract:: ... Eleven new secondary metabolites [kuroshines H–J (1–3), 27-methyl glycinate zoanthenamine (4), 27-hydroxyzoanthenamine (5), 27-methyl glycinate kuroshine A (6), 27-hydroxykuroshine A (7), 3β-hydroxy-28-deoxyzoanthenamine (8), 14α-hydroxy-28-deoxyzoanthenamine (9), 27-hydroxy-28-deoxyzoanthenamine (10), and kuroshine K (11)], along with seven known compounds (12–18), were isolated from the zoanthar ...
DOI:: 10.1021/acs.jnatprod.9b00451
: https://doi.org/10.1021/acs.jnatprod.9b00451

31. Anti-inflammatory Chalcone–Isoflavone Dimers and Chalcone Dimers from Caragana jubata

Author:: Lina Wang; Xuedong Yang; Yi Zhang; Ruixue Chen; Yuanyuan Cui; Qiulin Wang
Source:: Journal of natural products 2019 v.82 no.10 pp. 2761-2767
ISSN:: 1520-6025
Subject:: Caragana; anti-inflammatory activity; biochemical pathways; chalcone; heartwood; inhibitory concentration 50; interleukin-6; lipopolysaccharides; macrophages; mass spectrometry; mice; nitric oxide; nuclear magnetic resonance spectroscopy; rhizomes; secretion; tumor necrosis factor-alpha
Abstract:: ... Two new chalcone–isoflavone dimers, caraganins A (1) and B (2), two new chalcone dimers, caraganins C (3) and D (4), and eight known compounds (5–12) were obtained from the red heartwood of the rhizomes of Caragana jubata. The structures of caraganins A–D were established by 1D and 2D NMR spectroscopy, HRMS and ECD analysis, and comparison with previously known compounds. The anti-inflammatory act ...
DOI:: 10.1021/acs.jnatprod.9b00365
: https://doi.org/10.1021/acs.jnatprod.9b00365

32. Anti-inflammatory Ellagitannins from Cleidion brevipetiolatum for the Treatment of Rheumatoid Arthritis

Author:: Min Zhao; Xue Yuan; Ying-He Pei; Hao-Yu Ye; Ai-Hua Peng; Ming-Hai Tang; Da-Le Guo; Yun Deng; Li-Juan Chen
Source:: Journal of natural products 2019 v.82 no.9 pp. 2409-2418
ISSN:: 1520-6025
Subject:: IKappaB kinase; cytosol; edema; gene expression; glucosides; inducible nitric oxide synthase; inhibitory concentration 50; medicinal plants; messenger RNA; models; nitric oxide; oral administration; phosphorylation; prostaglandin synthase; rats; rheumatoid arthritis; spectral analysis; transcription factor NF-kappa B
Abstract:: ... Six new ellagitannins, brevipetins B–G (5 and 7–11), and a new phenolic glucoside, brevipetin A (4), along with six known compounds were isolated from the traditional Chinese medicinal plant Cleidion brevipetiolatum. Their structures and absolute configurations were determined by spectroscopic analyses, chemical methods, and TD-DFT-ECD calculations. Compounds 5–11 exhibited NO inhibitory effects w ...
DOI:: 10.1021/acs.jnatprod.8b00984
: https://doi.org/10.1021/acs.jnatprod.8b00984

33. Anti-inflammatory Lathyrane Diterpenoids from Euphorbia lathyris

Author:: Cui-Yun Zhang; Yan-Li Wu; Peng Zhang; Zhuang-Zhuang Chen; Hua Li; Li-Xia Chen
Source:: Journal of natural products 2019 v.82 no.4 pp. 756-764
ISSN:: 1520-6025
Subject:: Euphorbia lathyris; IKappaB kinase; X-ray diffraction; anti-inflammatory agents; cytotoxicity; diterpenoids; inducible nitric oxide synthase; inhibitory concentration 50; interleukin-1beta; interleukin-6; lipopolysaccharides; macrophages; nitric oxide; protein synthesis; seeds; transcription factor NF-kappa B
Abstract:: ... Six new lathyrane diterpenoids (1–6) and 10 known analogues (7–16), were separated from the seeds of Euphorbia lathyris. The absolute configuration of 1 was determined by X-ray crystallography, and the C-2′ configuration of 5 was elucidated by comparing experimental and calculated ECD data. These compounds were studied for their inhibition against nitric oxide (NO) generation induced by lipopolysa ...
DOI:: 10.1021/acs.jnatprod.8b00600
: https://doi.org/10.1021/acs.jnatprod.8b00600

34. Anti-inflammatory Mono- and Dimeric Sorbicillinoids from the Marine-Derived Fungus Trichoderma reesei 4670

Author:: Panpan Zhang; Yanlian Deng; Xiaojing Lin; Bin Chen; Jing Li; Hongju Liu; Senhua Chen; Lan Liu
Source:: Journal of natural products 2019 v.82 no.4 pp. 947-957
ISSN:: 1520-6025
Subject:: Trichoderma reesei; X-ray diffraction; anti-inflammatory activity; fungi; inhibitory concentration 50; lipopolysaccharides; moieties; nitric oxide; nuclear magnetic resonance spectroscopy; spectral analysis; structure-activity relationships
Abstract:: ... Eight new dimeric sorbicillinoids (1–3, 5–9) and 12 new monomeric sorbicillinoids (10–20, 25), along with five known analogues (4 and 21–24), were isolated from the marine-derived fungus Trichoderma reesei 4670. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography. Compound 1, containing a pyrrolidin-2-one mo ...
DOI:: 10.1021/acs.jnatprod.8b01029
: https://doi.org/10.1021/acs.jnatprod.8b01029

35. Anti-inflammatory Potential of Saponins from Aster tataricus via NF-κB/MAPK Activation

Author:: Xiang-Dong Su; Hyun-Jae Jang; Cai-Yi Wang; Seung Woong Lee; Mun-Chual Rho; Young Ho Kim; Seo Young Yang
Source:: Journal of natural products 2019 v.82 no.5 pp. 1139-1148
ISSN:: 1520-6025
Subject:: Aster tataricus; anti-inflammatory activity; chemical structure; inducible nitric oxide synthase; inhibitory concentration 50; lipopolysaccharides; macrophages; mice; nitric oxide; phosphorylation; prostaglandin synthase; protein content; saponins; spectral analysis; transcription factor NF-kappa B
Abstract:: ... Four new aster saponins (1–4) together with five known analogues (5–9) were isolated from Aster tataricus. The chemical structures of 1–4 were elucidated based on spectrometric and spectroscopic analysis and comparison with reported data. The potential anti-inflammatory activities of aster saponins 1–9 were evaluated subsequently by measuring lipopolysaccharide (LPS)-enhanced nitric oxide (NO) for ...
DOI:: 10.1021/acs.jnatprod.8b00856
: https://doi.org/10.1021/acs.jnatprod.8b00856

36. Anti-inflammatory Property of Imperatorin on Alveolar Macrophages and Inflammatory Lung Injury

Author:: Ya-Zhen Li; Jia-Hong Chen; Cheng-Fang Tsai; Wei-Lan Yeh
Source:: Journal of natural products 2019 v.82 no.4 pp. 1002-1008
ISSN:: 1520-6025
Subject:: anti-inflammatory activity; anti-inflammatory agents; edema; fibrosis; in vivo studies; inducible nitric oxide synthase; inflammation; interleukin-6; lungs; macrophages; medicinal plants; mice; respiratory tract diseases; signal transduction; transcription factor NF-kappa B; tumor necrosis factor-alpha; zymosan
Abstract:: ... Imperatorin is one of the furanocoumarin derivatives and exists in many medicinal herbs with anticancer, antiviral, antibacterial, and antihypertensive activities. In this study, we examined the anti-inflammatory effects of imperatorin on inflammation-associated lung diseases. Imperatorin reduced iNOS and COX-2 expression and also IL-6 and TNFα production enhanced by zymosan. Imperatorin also inhi ...
DOI:: 10.1021/acs.jnatprod.9b00145
: https://doi.org/10.1021/acs.jnatprod.9b00145

37. Anti-inflammatory and α-Glucosidase Inhibitory Activities of Labdane and Norlabdane Diterpenoids from the Rhizomes of Amomum villosum

Author:: Hong Yin; Wen-Jia Dan; Bo-Yi Fan; Chao Guo; Kui Wu; Ding Li; Kui-Feng Xian; Gennaro Pescitelli; Jin-Ming Gao
Source:: Journal of natural products 2019 v.82 no.11 pp. 2963-2971
ISSN:: 1520-6025
Subject:: Wurfbainia villosa; alpha-glucosidase; anhydrides; enzyme activity; enzyme inhibition; inhibitory concentration 50; labdane; moieties; nitric oxide; rhizomes; spectral analysis
Abstract:: ... A new tetranorditerpenoid (1), two new labdane diterpenoids (2, 3), and nine known analogues (4–12) were isolated from the rhizomes of Amomum villosum var. xanthioides. Compound 1 is an unprecedented rearranged tetranorlabdane diterpenoid, featuring a 6/6/5 fused tricarbocyclic skeleton with an α,β-unsaturated cyclopentenone unit, while 2 is a structurally rare labdane diterpenoid carrying a five- ...
DOI:: 10.1021/acs.jnatprod.9b00283
: https://doi.org/10.1021/acs.jnatprod.9b00283

38. Anti-prion Butenolides and Diphenylpropanones from the Australian Ascidian Polycarpa procera

Author:: Laurence K. Jennings; Luke P. Robertson; Kathryn E. Rudolph; Alan L. Munn; Anthony R. Carroll
Source:: Journal of natural products 2019 v.82 no.9 pp. 2620-2626
ISSN:: 1520-6025
Subject:: Polycarpa; bioactive compounds; bioactive properties; invertebrates; median effective concentration; metabolites; nuclear magnetic resonance spectroscopy
Abstract:: ... A library of 500 Australian marine invertebrate extracts was screened for anti-prion activity using a yeast-based assay, and this resulted in an extract from the ascidian Polycarpa procera showing potent activity. Purification of this extract led to the isolation of six new butenolide metabolites, the procerolides 1–4 and two related diphenylpropanones, the procerones 5 and 6, as the bioactive com ...
DOI:: 10.1021/acs.jnatprod.9b00551
: https://doi.org/10.1021/acs.jnatprod.9b00551

39. Antiangiogenic Activity of Compounds Isolated from Anarrhinum pedatum

Author:: Khadidja Aya Beladjila; Djemaa Berrehal; Zahia Kabouche; Maria Paola Germanò; Valeria D’Angelo; Nunziatina De Tommasi; Felicia D’Andrea; Alessandra Braca; Marinella De Leo
Source:: Journal of natural products 2019 v.82 no.3 pp. 510-519
ISSN:: 1520-6025
Subject:: Anarrhinum; Danio rerio; aerial parts; blood vessels; butanol; chickens; embryo (animal); iridoid glycosides; models; monoterpenoids; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:: ... Ten new iridoid glycosides (1–10) and two new monoterpenoids (11 and 12), together with nine known compounds (13–21), were isolated from the n-butanol extract of the aerial parts of Anarrhinum pedatum. The structural characterization of all compounds was performed by spectroscopic analysis, including 1D and 2D NMR and HRESIMS experiments. The isolates were assayed for their antiangiogenic activity ...
DOI:: 10.1021/acs.jnatprod.8b00893
: https://doi.org/10.1021/acs.jnatprod.8b00893

40. Antibacterial 5α-Spirostane Saponins from the Fruit of Cordyline manners-suttoniae

Author:: Trong D. Tran; Malin A. Olsson; Md Abu Choudhury; David J. McMillan; Jason K. Cullen; Peter G. Parsons; Paul V. Bernhardt; Paul W. Reddell; Steven M. Ogbourne
Source:: Journal of natural products 2019 v.82 no.10 pp. 2809-2817
ISSN:: 1520-6025
Subject:: Cordyline; Gram-positive bacteria; Staphylococcus aureus; X-ray diffraction; active ingredients; antibiotics; chloramphenicol; cytotoxicity; fractionation; fruits; methylene chloride; nuclear magnetic resonance spectroscopy; saponins; structure-activity relationships
Abstract:: ... Antibacterial-activity-guided fractionation of a dichloromethane extract from the fruit of Cordyline manners-suttoniae and subsequent structure–activity investigations resulted in the identification of 10 new (1–10) and one known (11) 5α-spirostane saponin. The structures of the new compounds were established by 1D and 2D NMR analyses. The absolute configurations of the isolated compounds were det ...
DOI:: 10.1021/acs.jnatprod.9b00502
: https://doi.org/10.1021/acs.jnatprod.9b00502

41. Antibacterial Aromatic Polyketides Incorporating the Unusual Amino Acid Enduracididine

Author:: Paolo Monciardini; Alice Bernasconi; Marianna Iorio; Cristina Brunati; Margherita Sosio; Laura Campochiaro; Paolo Landini; Sonia I. Maffioli; Stefano Donadio
Source:: Journal of natural products 2019 v.82 no.1 pp. 35-44
ISSN:: 1520-6025
Subject:: Nonomuraea; Staphylococcus aureus; amino acids; antibiotics; biosynthesis; cell walls; eukaryotic cells; genes; mechanism of action; minimum inhibitory concentration; multiple drug resistance; nuclear magnetic resonance spectroscopy; pathogens; peptidoglycans; polyketide synthases; polyketides; screening; toxicity
Abstract:: ... The increasing incidence of infections caused by drug-resistant pathogens requires new efforts for the discovery of novel antibiotics. By screening microbial extracts in an assay aimed at identifying compounds interfering with cell wall biosynthesis, based on differential activity against a Staphylococcus aureus strain and its isogenic l-form, the potent enduracyclinones (1, 2), containing the unc ...
DOI:: 10.1021/acs.jnatprod.8b00354
: https://doi.org/10.1021/acs.jnatprod.8b00354

42. Antibacterial Salinaphthoquinones from a Strain of the Bacterium Salinispora arenicola Recovered from the Marine Sediments of St. Peter and St. Paul Archipelago, Brazil

Author:: Alison B. da Silva; Edilberto R. Silveira; Diego V. Wilke; Elhton G. Ferreira; Leticia V. Costa-Lotufo; Maria Conceição M. Torres; Alejandro Pedro Ayala; Wendell S. Costa; Kirley M. Canuto; Alyne R. de Araújo-Nobre; Ana Jérsia Araújo; José Delano B. Marinho Filho; Otilia Deusdenia L. Pessoa
Source:: Journal of natural products 2019 v.82 no.7 pp. 1831-1838
ISSN:: 1520-6025
Subject:: Enterococcus faecalis; Staphylococcus aureus; X-ray diffraction; bacteria; biochemical pathways; marine sediments; minimum inhibitory concentration; nuclear magnetic resonance spectroscopy; quinones; Brazil
Abstract:: ... Salinaphthoquinones A–E (1–5) were isolated from a marine Salininispora arenicola strain, recovered from sediments of the St. Peter and St. Paul Archipelago, Brazil. The structures of the compounds were elucidated using a combination of spectroscopic (NMR, IR, HRESIMS) data, including single-crystal X-ray diffraction analysis. A plausible biosynthetic pathway for 1–5 is proposed. Compounds 1 to 4 ...
DOI:: 10.1021/acs.jnatprod.9b00062
: https://doi.org/10.1021/acs.jnatprod.9b00062

43. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa

Author:: Jovana Stanković; Dejan Gođevac; Vele Tešević; Zora Dajić-Stevanović; Ana Ćirić; Marina Soković; Miroslav Novaković
Source:: Journal of natural products 2019 v.82 no.6 pp. 1487-1495
ISSN:: 1520-6025
Subject:: Atriplex; Pseudomonas aeruginosa; antibacterial properties; butanol; flavonoids; glucosides; high performance liquid chromatography; nuclear magnetic resonance spectroscopy; salt marsh plants; secondary metabolites; silica gel; triterpenoid saponins
Abstract:: ... A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-β-d-glucuronopyranosyl-(1→2)-β-d-glucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, β-d-glucopyranosyl-3-O-(2-O-sulfo-β-d-galactopyranosyl)-(1→2)-α-l-arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, β-d-glucopyranosyl-3-O-(2-O-sulfo-β-d-galactopyranosyl ...
DOI:: 10.1021/acs.jnatprod.8b00970
: https://doi.org/10.1021/acs.jnatprod.8b00970

44. Antibacterial and Inhibitory Activities against Nitric Oxide Production of Coumaronochromones and Prenylated Isoflavones from Millettia extensa

Author:: Achara Raksat; Wisanu Maneerat; Narawadee Rujanapun; Raymond J. Andersen; Stephen G. Pyne; Surat Laphookhieo
Source:: Journal of natural products 2019 v.82 no.8 pp. 2343-2348
ISSN:: 1520-6025
Subject:: Gram-positive bacteria; Millettia; antibacterial properties; inhibitory concentration 50; isoflavones; macrophages; minimum inhibitory concentration; moieties; nitric oxide; nuclear magnetic resonance spectroscopy; root extracts
Abstract:: ... A chemical investigation of leaf and root extracts of Millettia extensa led to the isolation and structural elucidation of four new prenylated isoflavones, millexatins G–J (1–4), and three new coumaronochromones, millexatins K–M (5–7), along with 16 known compounds. The structures of the new compounds were determined on the basis of NMR and MS data. Compound 4 is a rare isoflavone having a 2-hydro ...
DOI:: 10.1021/acs.jnatprod.9b00216
: https://doi.org/10.1021/acs.jnatprod.9b00216

45. Antifungal Phenylpropanoid Glycosides from Lippia rubella

Author:: Gabriel R. Martins; Thamirys Silva da Fonseca; Lucero Martínez-Fructuoso; Rosineide Costa Simas; Fabio T. Silva; Fatima Regina G. Salimena; Daniela S. Alviano; Celuta Sales Alviano; Gilda Guimarães Leitão; Rogelio Pereda-Miranda; Suzana G. Leitão
Source:: Journal of natural products 2019 v.82 no.3 pp. 566-572
ISSN:: 1520-6025
Subject:: Cryptococcus neoformans; Lippia; active ingredients; amphotericin B; countercurrent chromatography; flavonoids; fractionation; glycosides; glycosylation; high performance liquid chromatography; lungs; medicinal properties; nuclear magnetic resonance spectroscopy; prototypes; spectral analysis; synergism; verbascoside
Abstract:: ... Lippia species share various pharmacological activities and are used in traditional cooking and medicine worldwide. Combined chromatographic techniques such as column chromatography, high-performance liquid chromatography, and countercurrent chromatography led to the purification of two new antifungal phenylpropanoid glycosides, lippiarubelloside A (1) and lippiarubelloside B (2), by bioactivity-d ...
DOI:: 10.1021/acs.jnatprod.8b00975
: https://doi.org/10.1021/acs.jnatprod.8b00975

46. Antifungal Sesquiterpenoids, Rhodocoranes, from Submerged Cultures of the Wrinkled Peach Mushroom, Rhodotus palmatus

Author:: Birthe Sandargo; Maira Michehl; Marc Stadler; Frank Surup
Source:: Journal of natural products 2019 v.83 no.3 pp. 720-724
ISSN:: 1520-6025
Subject:: Basidiomycota; antifungal properties; culture media; cytotoxicity; metabolites; mushrooms; nuclear magnetic resonance spectroscopy; sesquiterpenoids
Abstract:: ... Seven previously unknown sesquiterpenoids and norsesquiterpenoids, rhodocoranes F–L (1–7), were isolated from the fermentation broth of the basidiomycete Rhodotus palmatus. Their structures were elucidated utilizing 1D and 2D NMR techniques as well as HRESIMS; they are unusual noracorane, spiro[4.4]nonene, and acorane-type sesquiterpenoids. They include the first naturally occurring cyclopentylide ...
DOI:: 10.1021/acs.jnatprod.9b00871
: https://doi.org/10.1021/acs.jnatprod.9b00871

47. Antimicrobial Chrysophaentin Analogs Identified from Laboratory Cultures of the Marine Microalga Chrysophaeum taylorii

Author:: Jack R. Davison; Carole A. Bewley
Source:: Journal of natural products 2019 v.82 no.1 pp. 148-153
ISSN:: 1520-6025
Subject:: Bayesian theory; antibacterial properties; biochemical pathways; biphenyl; genes; metabolites; microalgae; nuclear magnetic resonance spectroscopy; ribosomal RNA; structure-activity relationships; Virgin Islands of the United States
Abstract:: ... A laboratory culture of the colonial marine alga Chrysophaeum taylorii NIES-1699 yielded a set of new bioactive chrysophaentin analogs, and their structures were determined by HRESIMS and NMR spectroscopy. Differences in the metabolites identified between cultured C. taylorii NIES-1699 and field-collected strains from the U.S. Virgin Islands revealed additional structure–activity relationships for ...
DOI:: 10.1021/acs.jnatprod.8b00858
: https://doi.org/10.1021/acs.jnatprod.8b00858

48. Antimicrobial Dolabellanes and Atranones from a Marine-Derived Strain of the Toxigenic Fungus Stachybotrys chartarum

Author:: Beiye Yang; Yan He; Shuang Lin; Jinwen Zhang; Huaqiang Li; Jianping Wang; Zhengxi Hu; Yonghui Zhang
Source:: Journal of natural products 2019 v.82 no.7 pp. 1923-1929
ISSN:: 1520-6025
Subject:: Acinetobacter baumannii; Candida albicans; Enterococcus faecalis; Stachybotrys chartarum; X-ray diffraction; antibiotic resistance; antimicrobial properties; chemical bonding; diterpenoids; fungi; methicillin; methicillin-resistant Staphylococcus aureus; minimum inhibitory concentration; spectroscopy; toxigenic strains
Abstract:: ... Three new dolabellane-type diterpenoids (1–3) and three new atranones (4–6) were isolated and identified from a marine-derived strain of the toxigenic fungus Stachybotrys chartarum. The planar and relative structures of 1–6 were elucidated using extensive spectroscopic methods, and their absolute configurations were fully confirmed via single-crystal X-ray diffraction analysis. Structurally, compo ...
DOI:: 10.1021/acs.jnatprod.9b00305
: https://doi.org/10.1021/acs.jnatprod.9b00305

49. Antinociceptive Grayanane Diterpenoids from the Leaves of Pieris japonica

Author:: Guijuan Zheng; Junfei Zhou; Lang Huang; Hao Zhang; Na Sun; Hanqi Zhang; Pengfei Jin; Mingbo Yue; Lingkui Meng; Guangmin Yao
Source:: Journal of natural products 2019 v.82 no.12 pp. 3330-3339
ISSN:: 1520-6025
Subject:: Pieris japonica; X-ray diffraction; analgesic effect; diterpenoids; leaf extracts; leaves; mice; morphine; nuclear magnetic resonance spectroscopy; structure-activity relationships; writhing test
Abstract:: ... Thirteen new grayanane diterpenoids (1–13) and 15 known analogues (14–28) were isolated from a leaf extract of Pieris japonica. Their structures were determined by spectrometric and spectroscopic methods, including HRESIMS, NMR, IR, and UV. The absolute configurations of 1, 3, 7–9, and 16 were defined by single-crystal X-ray diffraction analysis. 17-Hydroxygrayanotoxin XIX (1) represents the first ...
DOI:: 10.1021/acs.jnatprod.9b00569
: https://doi.org/10.1021/acs.jnatprod.9b00569

50. Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents

Author:: Alexander V. Samet; Oksana G. Shevchenko; Vyacheslav V. Rusak; Eduard M. Chartov; Andrey B. Myshlyavtsev; Daniil A. Rusanov; Marina N. Semenova; Victor V. Semenov
Source:: Journal of natural products 2019 v.82 no.6 pp. 1451-1458
ISSN:: 1520-6025
Subject:: 2,2-diphenyl-1-picrylhydrazyl; antioxidant activity; brain; erythrocytes; essential oils; free radical scavengers; hemolysis; lipid peroxidation; metabolites; mice; models; oxidation; parsley; structure-activity relationships
Abstract:: ... Free-radical-scavenging capacity antioxidant and membrane-protective properties of natural and related synthetic allylpolyalkoxybenzenes with different numbers of alkoxy/methoxy groups in the aromatic ring were evaluated using several in vitro models. These included the DPPH assay, inhibition of lipid peroxidation products accumulation, inhibition of H₂O₂-induced hemolysis, and oxidation of oxyhem ...
DOI:: 10.1021/acs.jnatprod.8b00878
: https://doi.org/10.1021/acs.jnatprod.8b00878

51. Antiplasmodial Diterpenoids from Psiadia arguta

Author:: Keshika Mahadeo; Gaëtan Herbette; Isabelle Grondin; Olivia Jansen; Hippolyte Kodja; Joyce Soulange; Sabina Jhaumeer-Laulloo; Patricia Clerc; Anne Gauvin-Bialecki; Michel Frederich
Source:: Journal of natural products 2019 v.82 no.5 pp. 1361-1366
ISSN:: 1520-6025
Subject:: Plasmodium falciparum; Psiadia; antimalarials; antiplasmodial properties; diterpenoids; ethyl acetate; formates; inhibitory concentration 50; leaves; mass spectrometry; nuclear magnetic resonance spectroscopy; phytochemicals
Abstract:: ... An ethyl acetate extract of Psiadia arguta leaves showed in vitro antiplasmodial activity against Plasmodium falciparum with IC₅₀ values of 12.3 ± 2.4 μg/mL (3D7 strain) and 13.5 ± 3.4 μg/mL (W2 strain). Phytochemical investigation led to the isolation and characterization of 16 compounds including four new diterpenoids: labdan-8α-ol-15-yl-(formate) (1), labdan-8α-ol-15-yl-(2-methylbutanoate) (2), ...
DOI:: 10.1021/acs.jnatprod.8b00698
: https://doi.org/10.1021/acs.jnatprod.8b00698

52. Antiproliferative Acylated Glycerols from New Zealand Propolis

Author:: Stephen Bloor; Owen Catchpole; Kevin Mitchell; Rosemary Webby; Paul Davis
Source:: Journal of natural products 2019 v.82 no.9 pp. 2359-2367
ISSN:: 1520-6025
Subject:: Populus; acetic acid; fatty acids; gastrointestinal system; inhibitory concentration 50; monoacylglycerols; neoplasm cells; phenolic compounds; propolis; stomach neoplasms; trees; New Zealand
Abstract:: ... Previous work has shown that a number of phenolic components of NZ propolis possess antiproliferative activity against certain human gastrointestinal cancer cell lines. Here we report on a series of acylglycerols isolated from the nonpolar fraction of propolis resin, which represent further bioactive constituents unrelated to the more usual phenolic compounds generally found in propolis. NZ propol ...
DOI:: 10.1021/acs.jnatprod.8b00562
: https://doi.org/10.1021/acs.jnatprod.8b00562

53. Antiproliferative Cardenolides from the Aerial Parts of Pergularia tomentosa

Author:: Seyed Hamzeh Hosseini; Milena Masullo; Antonietta Cerulli; Stefania Martucciello; Mahdi Ayyari; Cosimo Pizza; Sonia Piacente
Source:: Journal of natural products 2019 v.82 no.1 pp. 74-79
ISSN:: 1520-6025
Subject:: Pergularia; aerial parts; cardenolides; cell cycle; flavonols; glycosides; human cell lines; inhibitory concentration 50; liquid chromatography; mass spectrometry; methanol; neoplasm cells; nuclear magnetic resonance spectroscopy; prostatic neoplasms; roots; spectral analysis
Abstract:: ... The LC-MS analysis of the MeOH extract of the aerial parts of Pergularia tomentosa led to the isolation of 23 compounds, of which the structures were elucidated unambiguously by NMR spectroscopic data analysis. Three new doubly linked cardenolides (4, 13, 14) along with several known cardenolides (1–3, 5, 7, 8, 15–23) and flavonol glycosides (6, 9–12) were identified. LC-HRESIMS analysis, in the n ...
DOI:: 10.1021/acs.jnatprod.8b00630
: https://doi.org/10.1021/acs.jnatprod.8b00630

54. Antiproliferative Pterocarpans and Coumestans from Lespedeza bicolor

Author:: Nguyen Thi Thanh Thuy; Joo-Eun Lee; Hee Min Yoo; Namki Cho
Source:: Journal of natural products 2019 v.82 no.11 pp. 3025-3032
ISSN:: 1520-6025
Subject:: Lespedeza bicolor; apoptosis; blood; cell cycle checkpoints; chromatography; humans; mass spectrometry; methanol; mitochondria; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; roots; toxicity testing; ultraviolet-visible spectroscopy
Abstract:: ... Chromatographic purification of a methanol extract of the roots of Lespedeza bicolor led to the isolation of four new pterocarpans (1–4), two new coumestans (6 and 7), two new arylbenzofurans (8 and 9), and the known pterocarpan 1-methoxyerythrabyssin II (5). Their structures were identified using NMR spectroscopy, UV spectroscopy, and mass spectrometry. Cytotoxicity assays showed that compounds 1 ...
DOI:: 10.1021/acs.jnatprod.9b00567
: https://doi.org/10.1021/acs.jnatprod.9b00567

55. Antitrypanosomal Activity of Acetogenins Isolated from the Seeds of Porcelia macrocarpa Is Associated with Alterations in Both Plasma Membrane Electric Potential and Mitochondrial Membrane Potential

Author:: Emerson A. Oliveira; Ivanildo A. Brito; Marta L. Lima; Maiara Romanelli; José T. Moreira-Filho; Bruno J. Neves; Carolina H. Andrade; Patricia Sartorelli; Andre G. Tempone; Thais A. Costa-Silva; João Henrique G. Lago
Source:: Journal of natural products 2019 v.82 no.5 pp. 1177-1182
ISSN:: 1520-6025
Subject:: acetogenins; amastigotes; antitrypanosomal properties; death; drugs; flora; fluorometry; inhibitory concentration 50; membrane permeability; membrane potential; metabolites; mitochondrial membrane; nuclear magnetic resonance spectroscopy; parasites; pharmacokinetics; plasma membrane; reactive oxygen species; seeds; toxicity
Abstract:: ... As part of a drug discovery program aimed at the identification of anti-Trypanosoma cruzi metabolites from Brazilian flora, four acetogenins (1–4) were isolated from the seeds of Porcelia macrocarpa and were identified by NMR spectroscopy and HRESIMS. The new compounds 1 and 2 displayed activity against the trypomastigote (IC₅₀ = 0.4 and 3.6 μM) and amastigote (IC₅₀ = 23.0 and 27.7 μM) forms. The ...
DOI:: 10.1021/acs.jnatprod.8b00890
: https://doi.org/10.1021/acs.jnatprod.8b00890

56. Antitumor Activity of Vanicoside B Isolated from Persicaria dissitiflora by Targeting CDK8 in Triple-Negative Breast Cancer Cells

Author:: Donghwa Kim; Cai Yi Wang; Ruoci Hu; Ji Yun Lee; Thi-Thu-Trang Luu; Hee-Juhn Park; Sang Kook Lee
Source:: Journal of natural products 2019 v.82 no.11 pp. 3140-3149
ISSN:: 1520-6025
Subject:: Persicaria; antineoplastic activity; apoptosis; breast neoplasms; cell cycle checkpoints; cell lines; cyclin-dependent kinase; mice; molecular models; neoplasm cells; proteins; quercitrin; signal transduction; sucrose; toxicity
Abstract:: ... A flavonoid glycoside, quercitrin (1), and two phenylpropanoyl sucrose derivatives, vanicoside B (2) and lapathoside C (3), were isolated for the first time from the herb Persicaria dissitiflora. Vanicoside B (2) exhibited antiproliferative activity against a panel of cancer cell lines in triple-negative breast cancer (TNBC) MDA-MB-231 cells. The underlying mechanisms of the antitumor activity of ...
DOI:: 10.1021/acs.jnatprod.9b00720
: https://doi.org/10.1021/acs.jnatprod.9b00720

57. Antiviral Compounds from Codiaeum peltatum Targeted by a Multi-informative Molecular Networks Approach

Author:: Florent Olivon; Simon Remy; Gwendal Grelier; Cécile Apel; Cécilia Eydoux; Jean-Claude Guillemot; Johan Neyts; Leen Delang; David Touboul; Fanny Roussi; Marc Litaudon
Source:: Journal of natural products 2019 v.82 no.2 pp. 330-340
ISSN:: 1520-6025
Subject:: Chikungunya virus; Codiaeum; antiviral agents; bark; dengue; diterpenoids; enzyme inhibition; ions; moieties; nuclear magnetic resonance spectroscopy; ortho esters; phenanthrenes; prioritization; proteins; quinolones; spectral analysis; virus replication
Abstract:: ... From a set of 292 Euphorbiaceae extracts, the use of a molecular networking (MN)-based prioritization approach highlighted three clusters (MN1–3) depicting ions from the bark extract of Codiaeum peltatum. Based on their putative antiviral potential and structural novelty, the MS-guided purification of compounds present in MN1 and MN2 afforded two new daphnane-type diterpenoid orthoesters (DDO), co ...
DOI:: 10.1021/acs.jnatprod.8b00800
: https://doi.org/10.1021/acs.jnatprod.8b00800

58. Aphidicolin Chemistry of the Deep-Sea-Derived Fungus Botryotinia fuckeliana MCCC 3A00494

Author:: Siwen Niu; Jin-Mei Xia; Zengpeng Li; Long-He Yang; Zhi-Wei Yi; Chun-Lan Xie; Guizhen Peng; Zhu-Hua Luo; Zongze Shao; Xian-Wen Yang
Source:: Journal of natural products 2019 v.82 no.8 pp. 2307-2331
ISSN:: 1520-6025
Subject:: Botrytis cinerea; DNA damage; DNA-directed DNA polymerase; X-ray diffraction; apoptosis; clinical trials; cytotoxicity; derivatization; fungi; inhibitory concentration 50; neoplasm cells; neoplasms; optical isomerism; spectral analysis; tetrahydrofuran; Pacific Ocean
Abstract:: ... Aphidicolin, a potent DNA polymerase α inhibitor, has been explored in clinical trials for the treatment of cancer. So far, about 300 modified aphidicolins have been discovered. However, none have shown a stronger effect. Herein, we report 71 new (aphidicolins A1–A71, 1–71) and eight known (72–79) aphidicolin congeners from Botryotinia fuckeliana MCCC 3A00494, a fungus isolated from the western Pa ...
DOI:: 10.1021/acs.jnatprod.9b00705
: https://doi.org/10.1021/acs.jnatprod.9b00705

59. Arabinoxyloglucan Oligosaccharides May Contribute to the Antiadhesive Properties of Porcine Urine after Cranberry Consumption

Author:: Christina M. Coleman; Kimberly M. Auker; K. Brian Killday; Parastoo Azadi; Ian Black; Daneel Ferreira
Source:: Journal of natural products 2019 v.82 no.3 pp. 589-605
ISSN:: 1520-6025
Subject:: Escherichia coli; Vaccinium macrocarpon; adhesion; adults; catheters; cranberries; derivatization; erythrocytes; gel chromatography; high performance liquid chromatography; humans; juices; light scattering; metabolites; nuclear magnetic resonance spectroscopy; oligosaccharides; proanthocyanidins; sorbents; sows; spray drying; urinary tract diseases; urine
Abstract:: ... Cranberry (Vaccinium macrocarpon) juice is traditionally used for the prevention of urinary tract infections. Human urine produced after cranberry juice consumption can prevent Escherichia coli adhesion, but the antiadhesive urinary metabolites responsible have not been conclusively identified. Adult female sows were therefore fed spray-dried cranberry powder (5 g/kg/day), and urine was collected ...
DOI:: 10.1021/acs.jnatprod.8b01043
: https://doi.org/10.1021/acs.jnatprod.8b01043

60. Aromaticity and Electron Density of Hypericin

Author:: Sebastian Szymanski; Irena Majerz
Source:: Journal of natural products 2019 v.82 no.8 pp. 2106-2115
ISSN:: 1520-6025
Subject:: geometry; hypericin; quantum mechanics
Abstract:: ... The influence of the substituents on the geometry of the central ring system of hypericin has been analyzed. Substitution that causes flattening of the hypericin central rings is connected with introducing the aromatic character of the empty rings. All the hypericin rings have an aromatic character illustrated by the Harmonic Oscillator Measure of Aromaticity (HOMA), Nucleus Independent Chemical S ...
DOI:: 10.1021/acs.jnatprod.8b00872
: https://doi.org/10.1021/acs.jnatprod.8b00872

61. Ascomylactams A–C, Cytotoxic 12- or 13-Membered-Ring Macrocyclic Alkaloids Isolated from the Mangrove Endophytic Fungus Didymella sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C

Author:: Yan Chen; Zhaoming Liu; Yun Huang; Lan Liu; Jianguo He; Lan Wang; Jie Yuan; Zhigang She
Source:: Journal of natural products 2019 v.82 no.7 pp. 1752-1758
ISSN:: 1520-6025
Subject:: Didymella; X-ray diffraction; alkaloids; crystal structure; cytotoxicity; endophytes; fungi; human cell lines; humans; inhibitory concentration 50; mass spectrometry; moieties; neoplasm cells; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:: ... Three new 12- or 13-membered-ring macrocyclic alkaloids, named ascomylactams A–C (1–3), along with the analogues phomapyrrolidone C (4) and phomapyrrolidone A (5) were isolated from the mangrove endophytic fungus Didymella sp. CYSK-4. Their structures were elucidated by analysis of extensive spectroscopic data and mass spectrometric data. The structures and absolute configurations of 1 and 2 were ...
DOI:: 10.1021/acs.jnatprod.8b00918
: https://doi.org/10.1021/acs.jnatprod.8b00918

62. Asperpyridone A: An Unusual Pyridone Alkaloid Exerts Hypoglycemic Activity through the Insulin Signaling Pathway

Author:: Yuben Qiao; Qianqian Xu; Wenya Feng; Li Tao; Xiao-Nian Li; Junjun Liu; Hucheng Zhu; Yuanyuan Lu; Jianping Wang; Changxing Qi; Yongbo Xue; Yonghui Zhang
Source:: Journal of natural products 2019 v.82 no.10 pp. 2925-2930
ISSN:: 1520-6025
Subject:: Aspergillus; X-ray diffraction; alkaloids; bioassays; circular dichroism spectroscopy; electrospray ionization mass spectrometry; endophytes; fibroblast growth factors; fungi; gene ontology; genes; glucose; glycemic effect; human cell lines; insulin; insulin resistance; liver; metformin; nuclear magnetic resonance spectroscopy; pyridones; quantum mechanics; reverse transcriptase polymerase chain reaction; signal transduction
Abstract:: ... A pyridone alkaloid, asperpyridone A (1), which possesses an unusual pyrano[3,2-c]pyridine scaffold, was isolated from solid cultures of the endophytic fungus Aspergillus sp. TJ23. Its structure, including its absolute configuration, was determined using a combination of nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, quantum chemical calculations (electronic ...
DOI:: 10.1021/acs.jnatprod.9b00188
: https://doi.org/10.1021/acs.jnatprod.9b00188

63. Asperunguisins A–F, Cytotoxic Asperane Sesterterpenoids from the Endolichenic Fungus Aspergillus unguis

Author:: Yue-Lan Li; Yun Gao; Chun-Yu Liu; Chun-Jing Sun; Zun-Tian Zhao; Hong-Xiang Lou
Source:: Journal of natural products 2019 v.82 no.6 pp. 1527-1534
ISSN:: 1520-6025
Subject:: Aspergillus; DNA damage; X-ray diffraction; apoptosis; cell cycle checkpoints; cytotoxicity; fungi; human cell lines; humans; hydroxylation; inhibitory concentration 50; neoplasm cells; nuclear magnetic resonance spectroscopy
Abstract:: ... Six new asperane-type sesterterpenoids, asperunguisins A–F (1–6), were isolated from the endolichenic fungus Aspergillus unguis, together with a known analogue, aspergilloxide (7); these are rare asperane-type sesterterpenoids, characterized by a unique hydroxylated 7/6/6/5 tetracyclic system. The structures of asperunguisins A–F (1–6) were elucidated on the basis of spectroscopic methods (NMR and ...
DOI:: 10.1021/acs.jnatprod.8b01066
: https://doi.org/10.1021/acs.jnatprod.8b01066

64. Astratides: Insulin-Modulating, Insecticidal, and Antifungal Cysteine-Rich Peptides from Astragalus membranaceus

Author:: Jiayi Huang; Ka H. Wong; Stephanie V. Tay; Aida Serra; Siu Kuan Sze; James P. Tam
Source:: Journal of natural products 2019 v.82 no.2 pp. 194-204
ISSN:: 1520-6025
Subject:: Astragalus membranaceus; albumins; antifungal properties; blood glucose; cluster analysis; cytotoxicity; enzyme inhibitors; glucose; homeostasis; insects; insulin secretion; islets of Langerhans; medicinal plants; mice; new subfamily; peas; peptides; phylogeny; prolyl oligopeptidase; proteomics; roots; sequence homology; therapeutics
Abstract:: ... Astragalus membranaceus root, Huang Qi in Chinese, is a popular medicinal herb traditionally used to regulate blood glucose. Herein, the identification and characterization of two families of cysteine-rich peptides (CRPs), designated α- and β-astratides, from A. membranaceus roots are reported. Proteomic analysis showed that α-astratide aM1 and β-astratide bM1 belong to two distinct CRP families. ...
DOI:: 10.1021/acs.jnatprod.8b00521
: https://doi.org/10.1021/acs.jnatprod.8b00521

65. Austalides, Osteoclast Differentiation Inhibitors from a Marine-Derived Strain of the Fungus Penicillium rudallense

Author:: Weihong Wang; Jusung Lee; Kwang-Jin Kim; Youjung Sung; Kyu-Hyung Park; Eunseok Oh; Chanyoon Park; Young-Jin Son; Heonjoong Kang
Source:: Journal of natural products 2019 v.82 no.11 pp. 3083-3088
ISSN:: 1520-6025
Subject:: Penicillium; ligands; marine fungi; meroterpenoids; osteoclasts; phthalides; spectroscopy; transcription factor NF-kappa B
Abstract:: ... Four new meroterpenoids, austalides V–X (1–3) and a farnesylated phthalide derivative (4), were isolated from the culture of the marine fungus Penicillium rudallense, together with eight known meroterpenoids derivatives (5–12). Their structures, including absolute configurations, were determined by spectroscopic methods. All of the isolated compounds were evaluated for their inhibitory activities ...
DOI:: 10.1021/acs.jnatprod.9b00690
: https://doi.org/10.1021/acs.jnatprod.9b00690

66. Basimarols A, B, and C, Highly Oxygenated Pimarane Diterpenoids from Basilicum polystachyon

Author:: Yuen P. Tan; Yongbo Xue; Andrei I. Savchenko; Sevan D. Houston; Naphak Modhiran; Christopher L. D. McMillan; Glen M. Boyle; Paul V. Bernhardt; Paul R. Young; Daniel Watterson; Craig M. Williams
Source:: Journal of natural products 2019 v.82 no.10 pp. 2828-2834
ISSN:: 1520-6025
Subject:: Orthomyxoviridae; West Nile virus; X-ray diffraction; antiviral properties; arid zones; diterpenoids; human influenza; spectroscopy
Abstract:: ... The highly oxygenated pimarane diterpenoids basimarols A, B, and C (3–5) were isolated from the plant species Basilicum polystachyon, which was collected within the Australian arid zone. Structure elucidation was performed using a suite of spectroscopic techniques, including X-ray crystallography. Anticancer and anti-DENV activity of 3–5 was explored, but only limited activity was observed. More e ...
DOI:: 10.1021/acs.jnatprod.9b00522
: https://doi.org/10.1021/acs.jnatprod.9b00522

67. Benzophenone Compounds, from a Marine-Derived Strain of the Fungus Pestalotiopsis neglecta, Inhibit Proliferation of Pancreatic Cancer Cells by Targeting the MEK/ERK Pathway

Author:: Weihong Wang; Chanyoon Park; Eunseok Oh; Youjung Sung; Jusung Lee; Kyu-Hyung Park; Heonjoong Kang
Source:: Journal of natural products 2019 v.82 no.12 pp. 3357-3365
ISSN:: 1520-6025
Subject:: Pestalotiopsis; X-ray diffraction; antineoplastic agents; apoptosis; benzophenones; cell lines; cell proliferation; cytoplasm; drug therapy; enzyme activity; fractionation; fungi; human diseases; mitogen-activated protein kinase; neoplasm cells; pancreatic neoplasms; prognosis; spectroscopy
Abstract:: ... Pancreatic cancer, which has an extremely poor prognosis, is one of the most fatal human cancers. Chemotherapy is the main palliative treatment for advanced cancer patients and also plays an indispensable role in postoperative treatments for surgical patients. Therefore, there is an urgent need to develop more innovative anticancer drugs to fight against this fatal disease. Here, we investigate th ...
DOI:: 10.1021/acs.jnatprod.9b00646
: https://doi.org/10.1021/acs.jnatprod.9b00646

68. Bialternacins A–F, Aromatic Polyketide Dimers from an Endophytic Alternaria sp.

Author:: Cheng Long Yang; Hui Min Wu; Cheng Li Liu; Xuan Zhang; Zhi Kai Guo; Yu Chen; Fang Liu; Yong Liang; Rui Hua Jiao; Ren Xiang Tan; Hui Ming Ge
Source:: Journal of natural products 2019 v.82 no.4 pp. 792-797
ISSN:: 1520-6025
Subject:: Alternaria; X-ray diffraction; acetylcholinesterase; biochemical pathways; circular dichroism spectroscopy; endophytes; enzyme inhibition; inhibitory concentration 50; polyketides; spectral analysis
Abstract:: ... Six novel aromatic polyketide dimers, bialternacins A–F (1–6), were isolated from a plant endophytic Alternaria sp. The structures of compounds 1–6 were elucidated on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism analysis. Compounds 1, 2, 5, and 6 were characterized as four pairs of racemic mixtures. Compound (+)-5 was demonstrat ...
DOI:: 10.1021/acs.jnatprod.8b00705
: https://doi.org/10.1021/acs.jnatprod.8b00705

69. Bifunctional Duocarmycin Analogues as Inhibitors of Protein Tyrosine Kinases

Author:: Christian De Ford; Kamala Penchalaiah; Alexander Kreft; Matjaz Humar; Wolfgang Heydenreuter; Mehrnoush Kangani; Stephan A. Sieber; Lutz F. Tietze; Irmgard Merfort
Source:: Journal of natural products 2019 v.82 no.1 pp. 16-26
ISSN:: 1520-6025
Subject:: aldehyde dehydrogenase; cytotoxicity; in vitro studies; neoplasm cells; neoplasms; principal component analysis; vascular endothelial growth factor receptor-2
Abstract:: ... Bifunctional duocarmycin analogues are highly cytotoxic compounds that have been shown to be irreversible aldehyde dehydrogenase 1 inhibitors. Interestingly, cells with low aldehyde dehydrogenase 1 expression are also sensitive to bifunctional duocarmycin analogues, suggesting the existence of another target. Through in silico approaches, including principal component analysis, structure-similarit ...
DOI:: 10.1021/acs.jnatprod.8b00233
: https://doi.org/10.1021/acs.jnatprod.8b00233

70. Bioactive Dimeric Acylphloroglucinols from the Mexican Fern Elaphoglossum paleaceum

Author:: María Goretti Arvizu-Espinosa; Gilsane Lino von Poser; Amelia Teresinha Henriques; Aniceto Mendoza-Ruiz; Anaberta Cardador-Martínez; Reinier Gesto-Borroto; Pablo Noé Núñez-Aragón; María Luisa Villarreal-Ortega; Ashutosh Sharma; Alexandre Cardoso-Taketa
Source:: Journal of natural products 2019 v.82 no.4 pp. 785-791
ISSN:: 1520-6025
Subject:: Elaphoglossum; amine oxidase (flavin-containing); breasts; cell lines; cervix; chloroform; colorectal neoplasms; cytotoxicity; ferns and fern allies; hexane; inhibitory concentration 50; macrophages; mass spectrometry; mice; models; moieties; neoplasm cells; nitric oxide; nuclear magnetic resonance spectroscopy; plant extracts; rhizomes
Abstract:: ... Two new prenylated acylphloroglucinols, paleacenins A (1) and B (2), were isolated from the rhizome n-hexane and chloroform extracts of the fern Elaphoglossum paleaceum. Both compounds were found to possess the same geranylated filicinic acid moiety but have a different phloroglucinol ring substituent. Their structures were determined using ¹H and ¹³C NMR spectroscopic, HRMS, and ECD analysis. The ...
DOI:: 10.1021/acs.jnatprod.8b00677
: https://doi.org/10.1021/acs.jnatprod.8b00677

71. Bioactive Diterpenoids from the Stems of Euphorbia antiquorum

Author:: Yue Liang; Lijun An; Zhaoyu Shi; Xuke Zhang; Chunfeng Xie; Muhetaer Tuerhong; Zhaohui Song; Yasushi Ohizumi; Dongho Lee; Ling Shuai; Jing Xu; Yuanqiang Guo
Source:: Journal of natural products 2019 v.82 no.6 pp. 1634-1644
ISSN:: 1520-6025
Subject:: Euphorbia antiquorum; biological assessment; circular dichroism spectroscopy; computer simulation; diterpenoids; inducible nitric oxide synthase; nitric oxide; stems
Abstract:: ... A total of 18 diterpenoids, including 10 new analogues (1–10), were isolated from Euphorbia antiquorum. The structures were characterized by spectroscopic techniques, and circular dichroism data analysis was adopted to confirm the absolute configurations of 1–10. Compounds 1–9 were classified as ent-atisane diterpenoids, and 10 was assigned as an ent-kaurane diterpenoid. The biological evaluation ...
DOI:: 10.1021/acs.jnatprod.9b00134
: https://doi.org/10.1021/acs.jnatprod.9b00134

72. Bioactive Diterpenoids from the Stems of Euphorbia royleana

Author:: Peixia Wang; Chunfeng Xie; Lijun An; Xueyuan Yang; Yaru Xi; Shuo Yuan; Chenyue Zhang; Muhetaer Tuerhong; Da-Qing Jin; Dongho Lee; Jie Zhang; Yasushi Ohizumi; Jing Xu; Yuanqiang Guo
Source:: Journal of natural products 2019 v.82 no.2 pp. 183-193
ISSN:: 1520-6025
Subject:: Euphorbia; computer simulation; diterpenoids; inhibitory concentration 50; nitric oxide; spectroscopy; stems
Abstract:: ... Two ingenane- (1 and 2), two ent-atisane- (3 and 4), two ent-kaurane- (5 and 6), two ent-abietane- (7 and 8), and one ent-isopimarane-type (9) diterpenoid and 12 known analogues have been isolated from the methanolic extract of the stems of Euphorbia royleana. Their structures, including absolute configurations, were determined by extensive spectroscopic methods and ECD data analysis. The nitric o ...
DOI:: 10.1021/acs.jnatprod.8b00493
: https://doi.org/10.1021/acs.jnatprod.8b00493

73. Bioactive Meroterpenoids and Isocoumarins from the Mangrove-Derived Fungus Penicillium sp. TGM112

Author:: Meng Bai; Cai-Juan Zheng; Guo-Lei Huang; Rong-Qing Mei; Bin Wang; You-Ping Luo; Chao Zheng; Zhi-Gang Niu; Guang-Ying Chen
Source:: Journal of natural products 2019 v.82 no.5 pp. 1155-1164
ISSN:: 1520-6025
Subject:: Caenorhabditis elegans; Helicoverpa armigera; Penicillium; X-ray diffraction; chemical bonding; circular dichroism spectroscopy; fungi; growth retardation; inhibitory concentration 50; isocoumarins; larvae; median effective concentration; meroterpenoids; moieties; nuclear magnetic resonance spectroscopy; oxidation; spectral analysis
Abstract:: ... Two new meroterpenoids, penicianstinoids A and B (1 and 2), and eight new isocoumarins, peniciisocoumarins A–H (3–10), together with 10 known analogues (11–20) were obtained from the mangrove-derived fungus Penicillium sp. TGM112. The structures and absolute configurations of 1–10 were determined by interpretation of detailed NMR, MS spectroscopic data, X-ray diffraction analyses, modified Mosher’ ...
DOI:: 10.1021/acs.jnatprod.8b00866
: https://doi.org/10.1021/acs.jnatprod.8b00866

74. Bioactive Polyketide Derivatives from the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

Author:: Hai-Xia Liao; Cai-Juan Zheng; Guo-Lei Huang; Rong-Qing Mei; Xu-Hua Nong; Tai-Ming Shao; Guang-Ying Chen; Chang-Yun Wang
Source:: Journal of natural products 2019 v.82 no.8 pp. 2211-2219
ISSN:: 1520-6025
Subject:: Daldinia; alpha-glucosidase; circular dichroism spectroscopy; fungi; inhibitory concentration 50; lactones; metabolites; nuclear magnetic resonance spectroscopy; polyketides; quantum mechanics; stable isotopes
Abstract:: ... Five new tetralones, daldiniones A–E (1–5), three new chromones, 7-hydroxy-5-methoxy-2,3-dimethylchromone (9), 5-methoxy-2-propylchromone (10), and 7-ethyl-8-hydroxy-6-methoxy-2,3-dimethylchromone (11), and two new lactones, helicascolides D and E (16 and 17), together with nine known metabolites (6–8, 12–15, and 18–19) were isolated from the mangrove-derived fungus Daldinia eschscholtzii HJ004. T ...
DOI:: 10.1021/acs.jnatprod.9b00241
: https://doi.org/10.1021/acs.jnatprod.9b00241

75. Bioactive Secondary Metabolites from Bacillus subtilis: A Comprehensive Review

Author:: Felix Kaspar; Peter Neubauer; Matthias Gimpel
Source:: Journal of natural products 2019 v.82 no.7 pp. 2038-2053
ISSN:: 1520-6025
Subject:: Bacillus subtilis; antimicrobial properties; bacteria; biosurfactants; biosynthesis; drugs; fermentation; genetically engineered microorganisms; lipopeptides; macrolides; medicine; nonribosomal peptides; plant pathogens
Abstract:: ... Bacillus subtilis is widely underappreciated for its inherent biosynthetic potential. This report comprehensively summarizes the known bioactive secondary metabolites from B. subtilis and highlights potential applications as plant pathogen control agents, drugs, and biosurfactants. B. subtilis is well known for the production of cyclic lipopeptides exhibiting strong surfactant and antimicrobial ac ...
DOI:: 10.1021/acs.jnatprod.9b00110
: https://doi.org/10.1021/acs.jnatprod.9b00110

76. Bioactive Streptoglutarimides A–J from the Marine-Derived Streptomyces sp. ZZ741

Author:: Di Zhang; Wenwen Yi; Hengju Ge; Zhizhen Zhang; Bin Wu
Source:: Journal of natural products 2019 v.82 no.10 pp. 2800-2808
ISSN:: 1520-6025
Subject:: Candida albicans; Escherichia coli; Streptomyces; X-ray diffraction; antibiotic resistance; antimicrobial properties; glioma; human cell lines; inhibitory concentration 50; methicillin; methicillin-resistant Staphylococcus aureus; minimum inhibitory concentration; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:: ... The new streptoglutarimides A–J (1–10) and the known streptovitacin A (11) were isolated from a marine-derived actinomycete, Streptomyces sp. ZZ741. Structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, ECD calculations, Mosher′s method, and a single-crystal X-ray diffraction experiment. Streptoglutarimide H (8) and streptovitacin A ...
DOI:: 10.1021/acs.jnatprod.9b00481
: https://doi.org/10.1021/acs.jnatprod.9b00481

77. Bioassay-Guided Isolation of Fungistatic Compounds from Mimosa caesalpiniifolia Leaves

Author:: Marcelo J. Dias Silva; Ana M. Simonet; Naiara C. Silva; Amanda L. T. Dias; Wagner Vilegas; Francisco A. Macías
Source:: Journal of natural products 2019 v.82 no.6 pp. 1496-1502
ISSN:: 1520-6025
Subject:: Candida krusei; Mimosa caesalpiniifolia; antifungal properties; apigenin; azoles; ethyl gallate; inhibitory concentration 50; leaf extracts; leaves; mass spectrometry; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:: ... A bioassay-guided phytochemical study of a Mimosa caesalpiniifolia leaf extract with antifungal activity permitted the identification of 28 compounds, including the new 6-(β-boivinopyranosyl)apigenin (1), 8-(β-oliopyranosyl)apigenin (2), (E)-6-(2-carboxyethenyl)apigenin (3), (E)-8-(2-carboxyethenyl)apigenin (4), and 7,5″-anhydro-6-(α-2,6-dideoxy-5-hydroxyarabinohexopyranosyl)apigenin (5). The stru ...
DOI:: 10.1021/acs.jnatprod.8b01025
: https://doi.org/10.1021/acs.jnatprod.8b01025

78. Biomimetic Transformation of p-Menthene Glucosides into p-Cymenes and Carvotanacetone

Author:: Julio C. Pardo-Novoa; Héctor M. Arreaga-González; Sinuhé Galván-Gómez; Gabriela Rodríguez-García; Rosa E. del Río; Carlos M. Cerda-García-Rojas; Pedro Joseph-Nathan; Mario A. Gómez-Hurtado
Source:: Journal of natural products 2019 v.82 no.3 pp. 485-491
ISSN:: 1520-6025
Subject:: Ageratina; acetylation; acid treatment; biomimetics; carvacrol; essential oils; glucosides; metabolism; monoterpenoids; oxidation; p-cymene; reaction mechanisms
Abstract:: ... A biomimetic transformation of p-menthene glucosides into aromatic monoterpenoids that alluded to mechanisms for essential oil metabolism, which lines up with the precepts of molecular economy, is described. Acid treatment of (−)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-β-d-glucopyranoside (1) and (−)-(3S,4R,5R,6S)-3,5,6-trihydroxy-1-menthene 3-O-β-d-glucopyranoside (2), from Ageratina glabrata, yi ...
DOI:: 10.1021/acs.jnatprod.8b00855
: https://doi.org/10.1021/acs.jnatprod.8b00855

79. Biosynthesis of Nonimmunosuppressive FK506 Analogues with Antifungal Activity

Author:: Ji Yoon Beom; Jin A Jung; Kyung-Tae Lee; Areum Hwangbo; Myoung Chong Song; Yeonseon Lee; Soo Jung Lee; Ji Hoon Oh; Sang-Jun Ha; Sang-Jip Nam; Eunji Cheong; Yong-Sun Bahn; Yeo Joon Yoon
Source:: Journal of natural products 2019 v.82 no.8 pp. 2078-2086
ISSN:: 1520-6025
Subject:: Aspergillus fumigatus; Candida albicans; Cryptococcus neoformans; Streptomyces; T-lymphocytes; antifungal properties; biosynthesis; drugs; fluconazole; fungi; immunosuppression; interleukin-2; macrolides; pathogenesis; pathogens; phosphoprotein phosphatase; signal transduction
Abstract:: ... A reduction in the strong immunosuppressive activity of FK506 (1) is essential for developing this compound as an antifungal agent. Seven new FK506 analogues modified at both the FK506-binding protein 12- and the calcineurin-binding regions were biosynthesized. 9-DeoxoFK520 (7) exhibited a >900-fold reduction in the in vitro immunosuppressive activity but maintained significant antifungal activity ...
DOI:: 10.1021/acs.jnatprod.9b00144
: https://doi.org/10.1021/acs.jnatprod.9b00144

80. Bipolaricins A–I, Ophiobolin-Type Tetracyclic Sesterterpenes from a Phytopathogenic Bipolaris sp. Fungus

Author:: Mengting Liu; Weiguang Sun; Ling Shen; Xincai Hao; Weaam Hasan Al Anbari; Shuang Lin; Huaqiang Li; Weixi Gao; Jianping Wang; Zhengxi Hu; Yonghui Zhang
Source:: Journal of natural products 2019 v.82 no.10 pp. 2897-2906
ISSN:: 1520-6025
Subject:: Bipolaris; X-ray diffraction; chemokine CCL4; chemokine CCL5; copper; cytotoxicity; enzyme inhibition; enzyme inhibitors; ethyl acetate; fungi; hydroxymethylglutaryl-CoA reductases; inhibitory concentration 50; interleukin-13; interleukin-1beta; lipopolysaccharides; macrophages; nitric oxide; nuclear magnetic resonance spectroscopy; phytochemicals; phytotoxins; spectral analysis; therapeutics; transcription factor NF-kappa B; tumor necrosis factor-alpha
Abstract:: ... A preliminary phytochemical investigation on the EtOAc extracts of the fungus Bipolaris sp. TJ403-B1 resulted in the identification of 12 ophiobolin-type phytotoxins (1–12), including nine new ones, termed bipolaricins A–I (1–9). The structures of 1–9 were elucidated via spectroscopic data (including HRESIMS and 1D and 2D NMR) and single-crystal X-ray diffraction (Cu Kα) analyses. All of the isola ...
DOI:: 10.1021/acs.jnatprod.9b00744
: https://doi.org/10.1021/acs.jnatprod.9b00744

81. Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a

Author:: Marian Frank; Rudolf Hartmann; Malte Plenker; Attila Mándi; Tibor Kurtán; Ferhat Can Özkaya; Werner E. G. Müller; Matthias U. Kassack; Alexandra Hamacher; Wenhan Lin; Zhen Liu; Peter Proksch
Source:: Journal of natural products 2019 v.82 no.8 pp. 2159-2166
ISSN:: 1520-6025
Subject:: Penicillium; benzene; bromination; cytotoxicity; diphenyl ethers; fermentation; fungi; inhibitory concentration 50; mice; moieties; neoplasm cells; nuclear magnetic resonance spectroscopy; ovarian neoplasms; quinones; rice; sodium bromide; stereoisomers
Abstract:: ... The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides. Fermentation of the fungus on solid rice medium yielded one new chlorinated diphenyl ether (1) and 13 known compounds (2–14). Addition of 5% NaBr to the rice medium increased the amounts of 4–6, while lowering the amounts of 8, 12, and 14. Furthermore, it induced the accumulation of 17 a ...
DOI:: 10.1021/acs.jnatprod.9b00151
: https://doi.org/10.1021/acs.jnatprod.9b00151

82. Buxaustroines A–N, a Series of 17(13→18)abeo-Cycloartenol Triterpenoidal Alkaloids from Buxus austro-yunnanensis and Their Cardioprotective Activities

Author:: Zhi-Nan Xiang; Wen-Qin Yi; Yong-Long Wang; Li-Dong Shao; Cheng-Qi Zhang; Yan Yuan; Jun Pan; Luo-Sheng Wan; Jia-Chun Chen
Source:: Journal of natural products 2019 v.82 no.11 pp. 3111-3120
ISSN:: 1520-6025
Subject:: Buxus; X-ray diffraction; alkaloids; biochemical pathways; crystallography; nuclear magnetic resonance spectroscopy; protective effect; structure-activity relationships
Abstract:: ... Buxaustroines A–N (1–14), a series of triterpenoidal alkaloids featuring a novel 17(13→18)abeo motif, were obtained from the extract of Buxus austro-yunnanensis. Their structures were assigned based on NMR data analysis and X-ray diffraction crystallography. A putative biosynthetic pathway for one of the alkaloids from a co-isolate 15 is proposed. In the assessment of their bioactivities, some of ...
DOI:: 10.1021/acs.jnatprod.9b00652
: https://doi.org/10.1021/acs.jnatprod.9b00652

83. C-Phycocyanin from Spirulina Inhibits α-Synuclein and Amyloid-β Fibril Formation but Not Amorphous Aggregation

Author:: Yanqin Liu; Blagojce Jovcevski; Tara L. Pukala
Source:: Journal of natural products 2019 v.82 no.1 pp. 66-73
ISSN:: 1520-6025
Subject:: Parkinson disease; Spirulina; amyloid; anti-inflammatory activity; catalase; cataract; clinical trials; nuclear magnetic resonance spectroscopy; protein folding
Abstract:: ... Proteinopathies including cataracts and neurodegenerative diseases, such as Alzheimer’s and Parkinson’s disease, are characterized by a series of aberrant protein folding events, resulting in amorphous aggregate or amyloid fibril formation. In the latter case, research has heavily focused on the development of small-molecule inhibitors with limited success during clinical trials. However, very few ...
DOI:: 10.1021/acs.jnatprod.8b00610
: https://doi.org/10.1021/acs.jnatprod.8b00610

84. Callistemonols A and B, Potent Antimicrobial Acylphloroglucinol Derivatives with Unusual Carbon Skeletons from Callistemon viminalis

Author:: Jie-Wei Wu; Bai-Lin Li; Chunping Tang; Chang-Qiang Ke; Nan-Lin Zhu; Sheng-Xiang Qiu; Yang Ye
Source:: Journal of natural products 2019 v.82 no.7 pp. 1917-1922
ISSN:: 1520-6025
Subject:: Callistemon viminalis; antibacterial properties; antibiotic resistance; carbon; chemical bonding; dibenzofuran; furans; leaves; methicillin; microorganisms; moieties; nuclear magnetic resonance spectroscopy; phytochemicals; spectral analysis
Abstract:: ... A phytochemical investigation on the leaves of Callistemon viminalis resulted in the isolation of two unusual compounds, callistemonols A (1) and B (2). Callistemonol A (1) possesses a novel skeleton of a furan ring fusing both an α,β-triketone and a phloroglucinol unit, while callistemonol B (2) is an acylphloroglucinol derivative featuring two methyl substituents on a five-membered ring and an i ...
DOI:: 10.1021/acs.jnatprod.9b00064
: https://doi.org/10.1021/acs.jnatprod.9b00064

85. Camporidines A and B: Antimetastatic and Anti-inflammatory Polyketide Alkaloids from a Gut Bacterium of Camponotus kiusiuensis

Author:: Seong-Heon Hong; Yeon Hee Ban; Woong Sub Byun; Donghwa Kim; Yong-Joon Jang; Joon Soo An; Bora Shin; Sang Kook Lee; Jongheon Shin; Yeo Joon Yoon; Dong-Chan Oh
Source:: Journal of natural products 2019 v.82 no.4 pp. 903-910
ISSN:: 1520-6025
Subject:: Camponotus; Streptomyces; alkaloids; amination; anti-inflammatory activity; biochemical pathways; bioinformatics; biosynthesis; breast neoplasms; carpenter ants; cell lines; intestinal microorganisms; lipopolysaccharides; mass spectrometry; metastasis; multigene family; neoplasm cells; nitric oxide; nuclear magnetic resonance spectroscopy; oxidation; polyketides; schiff bases; transferases
Abstract:: ... Chemical studies of gut bacteria of the carpenter ant Camponotus kiusiuensis led to the discovery of two new alkaloids, camporidines A and B (1 and 2), from Streptomyces sp. STA1. The structures of 1 and 2 were established as new polyketide alkaloids bearing a piperidine–cyclopentene–epoxide 6/5/3 tricyclic system based on NMR spectroscopic and mass spectrometric analysis. The relative configurati ...
DOI:: 10.1021/acs.jnatprod.8b01000
: https://doi.org/10.1021/acs.jnatprod.8b01000

86. Characterization of the Biosynthetic Gene Cluster for the Antibiotic Armeniaspirols in Streptomyces armeniacus

Author:: Yongjian Qiao; Jiayan Yan; Jia Jia; Jiao Xue; Xudong Qu; Yunfeng Hu; Zixin Deng; Hongkai Bi; Dongqing Zhu
Source:: Journal of natural products 2019 v.82 no.2 pp. 318-323
ISSN:: 1520-6025
Subject:: Streptomyces armeniacus; antibiotics; antimicrobial properties; biosynthesis; enzymes; mechanism of action; moieties; multigene family; pathogens; pyrroles
Abstract:: ... Armeniaspirols (1–3) are potent antibiotics against Gram-positive pathogens. Through a biosynthetic investigation, we identified four enzymes involved in the structural modification of 1–3. Manipulation of their activity led to the generation of 4–6 and nine novel analogues, 7–15. Bioactivity assessments revealed that the pyrrole chloro group and the methyl group are important for the antimicrobia ...
DOI:: 10.1021/acs.jnatprod.8b00753
: https://doi.org/10.1021/acs.jnatprod.8b00753

87. Charting Angiosperm Chemistry: Evolutionary Perspective on Specialized Metabolites Reflected in Chemical Property Space

Author:: Astrid Henz Ryen; Anders Backlund
Source:: Journal of natural products 2019 v.82 no.4 pp. 798-812
ISSN:: 1520-6025
Subject:: Angiospermae; biochemical pathways; enzymes; metabolism; metabolites; niches; physicochemical properties
Abstract:: ... Plants possess an outstanding chemical diversity of specialized metabolites developed to adapt to environmental niches and increase fitness. The observed diversity is hypothesized to result from various evolutionary mechanisms, such as the continuous branching off and extension of existing biosynthetic pathways or enhanced levels of catalytic promiscuity in certain enzymes. In this study, ChemGPS- ...
DOI:: 10.1021/acs.jnatprod.8b00767
: https://doi.org/10.1021/acs.jnatprod.8b00767

88. Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Author:: Young H. Seo; Shin-Young Kang; Ji-Sun Shin; Seung M. Ryu; A Y. Lee; Goya Choi; Byeong C. Moon; Dae-Sik Jang; Sang H. Shim; Dongho Lee; Kyung-Tae Lee; Jun Lee
Source:: Journal of natural products 2019 v.82 no.12 pp. 3379-3385
ISSN:: 1520-6025
Subject:: Agastache rugosa; aerial parts; anti-inflammatory activity; chemical composition; flavones; glucosides; inhibitory concentration 50; lipopolysaccharides; macrophages; nuclear magnetic resonance spectroscopy; prostaglandins
Abstract:: ... A new flavone glucoside, acacetin-7-O-(3″-O-acetyl-6″-O-malonyl)-β-d-glucopyranoside (1), two new phenolic glucosides, (3R,7R)-tuberonic acid-12-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (14) and salicylic acid-2-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (15), and two new phenylpropanoid glucosides, chavicol-1-O-(6′-O-methylmalonyl)-β-d-glucopyranoside (17) and chavicol-1-O-(6′-O-acetyl)-β-d-gluco ...
DOI:: 10.1021/acs.jnatprod.9b00697
: https://doi.org/10.1021/acs.jnatprod.9b00697

89. Chemical Constituents of Anneslea fragrans and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line

Author:: Ashraf M. Omar; Dya Fita Dibwe; Ahmed M. Tawila; Sijia Sun; Ampai Phrutivorapongkul; Suresh Awale
Source:: Journal of natural products 2019 v.82 no.11 pp. 3133-3139
ISSN:: 1520-6025
Subject:: acid hydrolysis; betulin; cell movement; chalcone; chemical composition; cytotoxicity; glucose; human cell lines; human diseases; lactones; leaves; moieties; neoplasm cells; nuclear magnetic resonance spectroscopy; pancreatic neoplasms; secondary metabolites; spectral analysis
Abstract:: ... An ethanolic extract of Anneslea fragrans leaves showed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under a nutrient-deprived condition, with a PC₅₀ value of 9.6 μg/mL. Phytochemical investigation of this active extract led to the isolation of two new secondary metabolites, fragranones A (1) and B (2), along with 15 previously reported compounds. The structure elu ...
DOI:: 10.1021/acs.jnatprod.9b00735
: https://doi.org/10.1021/acs.jnatprod.9b00735

90. Chivosazole A Modulates Protein–Protein Interactions of Actin

Author:: Shuaijun Wang; Florian A. Gegenfurtner; Alvaro H. Crevenna; Christoph Ziegenhain; Zane Kliesmete; Wolfgang Enard; Rolf Müller; Angelika M. Vollmar; Sabine Schneider; Stefan Zahler
Source:: Journal of natural products 2019 v.82 no.7 pp. 1961-1970
ISSN:: 1520-6025
Subject:: actin; binding sites; crystal structure; polymerization; profilins; protein-protein interactions; transcription (genetics)
Abstract:: ... Actin is a protein of central importance for many cellular key processes. It is regulated by local interactions with a large number of actin binding proteins (ABPs). Various compounds are known to either increase or decrease the polymerization dynamics of actin. However, no actin binding compound has been developed for clinical applications yet because of selectivity issues. We provide a crystal s ...
DOI:: 10.1021/acs.jnatprod.9b00335
: https://doi.org/10.1021/acs.jnatprod.9b00335

91. Chloraserrtone A, a Sesquiterpenoid Dimer from Chloranthus serratus

Author:: Bai Bai; Shao-Xia Ye; De-Po Yang; Long-Ping Zhu; Gui-Hua Tang; Yun-Yun Chen; George Qian Li; Zhi-Min Zhao
Source:: Journal of natural products 2019 v.82 no.2 pp. 407-411
ISSN:: 1520-6025
Subject:: Chloranthus; X-ray diffraction; biosynthesis; inhibitory concentration 50; nitric oxide; nuclear magnetic resonance spectroscopy; sesquiterpenoids
Abstract:: ... Chloraserrtone A (1), a new sesquiterpenoid dimer with two lindenane-type sesquiterpenoid monomers bridged by two six-membered rings, was obtained from Chloranthus serratus. A combination of UV, IR, NMR, HRESIMS, and X-ray diffraction data were used to elucidate the structure of 1. Compound 1 represents the first lindenane-type sesquiterpenoid dimer with extremely unique C-15–C-15′, C-4–C-6′, and ...
DOI:: 10.1021/acs.jnatprod.8b00418
: https://doi.org/10.1021/acs.jnatprod.8b00418

92. Cholinesterase Inhibitory Arisugacins L–Q from a Penicillium sp. Isolate Obtained through a Citizen Science Initiative and Their Activities in a Phenotype-Based Zebrafish Assay

Author:: Wentao Dai; Imelda T. Sandoval; Shengxin Cai; Kaylee A. Smith; Richard Glenn C. Delacruz; Kevin A. Boyd; Jessica J. Mills; David A. Jones; Robert H. Cichewicz
Source:: Journal of natural products 2019 v.82 no.9 pp. 2627-2637
ISSN:: 1520-6025
Subject:: Danio rerio; Penicillium; acetylcholinesterase; bioactive properties; cholinesterase; embryo (animal); enzyme inhibition; fungi; in vitro studies; inhibitory concentration 50; lactones; locomotion; meroterpenoids; metabolites; muscles; nuclear magnetic resonance spectroscopy; phenotype; screening; therapeutics
Abstract:: ... Phenotype-based screening of a fungal extract library yielded an active sample from a Penicillium sp. isolate that impaired zebrafish motility. Bioassay-guided purification led to the identification of 14 meroterpenoids including six new metabolites, arisugacins L–Q (4, 5, 8, and 12–14), seven known arisugacins (1–3, 6, 7, 9, and 10), and one known terreulactone (11). Their structures were determi ...
DOI:: 10.1021/acs.jnatprod.9b00563
: https://doi.org/10.1021/acs.jnatprod.9b00563

93. Cinerols, Nitrogenous Meroterpenoids from the Marine Sponge Dysidea cinerea

Author:: Wei-Hua Jiao; Jing Li; Dan Wang; Meng-Meng Zhang; Li-Yun Liu; Fan Sun; Jing-Ya Li; Robert J. Capon; Hou-Wen Lin
Source:: Journal of natural products 2019 v.82 no.9 pp. 2586-2593
ISSN:: 1520-6025
Subject:: ATP citrate synthase; Porifera; benzimidazole; inhibitory concentration 50; melanoma; meroterpenoids; moieties; protein-tyrosine-phosphatase; spectral analysis; South China Sea
Abstract:: ... Eleven new nitrogenous meroterpenoids, cinerols A–K (1–11), were isolated from the marine sponge Dysidea cinerea collected in the South China Sea, and their structures were determined by detailed spectroscopic analysis. Cinerols A (1) and B (2) feature a rare 5H-pyrrolo[1,2a]benzimidazole moiety, while cinerols C–G (3–7) are examples of rare meroterpene benzoxazoles. The cinerols are noncytotoxic ...
DOI:: 10.1021/acs.jnatprod.9b00471
: https://doi.org/10.1021/acs.jnatprod.9b00471

94. Clavariopsins C–I, Antifungal Cyclic Depsipeptides from the Aquatic Hyphomycete Clavariopsis aquatica

Author:: Thin Wut Soe; Chunguang Han; Ryosuke Fudou; Kenichi Kaida; Yuki Sawaki; Tomohiko Tomura; Makoto Ojika
Source:: Journal of natural products 2019 v.82 no.7 pp. 1971-1978
ISSN:: 1520-6025
Subject:: Alternaria alternata; Aspergillus niger; Botrytis cinerea; Colletotrichum orbiculare; Fusarium oxysporum; Hyphomycetes; Magnaporthe oryzae; amino acids; antifungal agents; antifungal properties; cell lines; cytotoxicity; depsipeptides; high performance liquid chromatography; hyphae; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; plant pathogenic fungi
Abstract:: ... Seven new cyclic depsipeptides, clavariopsins C–I (3–9), together with two known congeners, clavariopsins A and B (1 and 2), were isolated from the aquatic hyphomycete Clavariopsis aquatica. Their planar structures, which consist of nine amino acids and one α-hydroxy acid, were elucidated by NMR spectroscopy and HRESIMS. The absolute configurations were established by the advanced Marfey’s method ...
DOI:: 10.1021/acs.jnatprod.9b00366
: https://doi.org/10.1021/acs.jnatprod.9b00366

95. Clavukoellians A–F, Highly Rearranged Nardosinane Sesquiterpenoids with Antiangiogenic Activity from Clavulariakoellikeri

Author:: Qi Wang; Zhenquan Hu; Xiangchao Luo; Jing Liu; Guoqiang Li; Shugeng Cao; Qingsong Liu
Source:: Journal of natural products 2019 v.82 no.5 pp. 1331-1337
ISSN:: 1520-6025
Subject:: corals; nuclear magnetic resonance spectroscopy; quantum mechanics; sesquiterpenoids; tissue repair
Abstract:: ... Six new nardosinane-type sesquiterpenoids, clavukoellians A–F (1–6), together with one new neolemnane-type sesquiterpene, 4-O-deacetylparalemnolin D (7), were isolated from the marine soft coral Clavularia koellikeri. The structures of compounds 1–7 were elucidated by NMR spectroscopy, ECD analysis, and quantum chemical calculation methods. Compounds 1 and 7 demonstrated significant antiangiogenic ...
DOI:: 10.1021/acs.jnatprod.9b00100
: https://doi.org/10.1021/acs.jnatprod.9b00100

96. Colletopeptides A–D, Anti-inflammatory Cyclic Tridepsipeptides from the Plant Endophytic Fungus Colletotrichum sp. S8

Author:: Li Feng; Jia Wang; Shuai Liu; Xue-Jia Zhang; Qi-Rui Bi; Yan-Yun Hu; Zhe Wang; Ning-Hua Tan
Source:: Journal of natural products 2019 v.82 no.6 pp. 1434-1441
ISSN:: 1520-6025
Subject:: Colletotrichum; IKappaB kinase; Rubia; X-ray diffraction; dodecanoic acid; endophytes; fungi; inhibitory concentration 50; interleukin-6; liquid chromatography; macrophages; nitric oxide; phosphorylation; proteins; spectral analysis; stems; tumor necrosis factor-alpha
Abstract:: ... Four new hybrid peptide-polyketide cyclic tridepsipeptides, colletopeptides A–D (1–4), were isolated and characterized from the endophytic fungus Colletotrichum sp. S8 derived from the stems of Rubia podantha with the guidance of LC-UV-MS detection. Their structures were elucidated by extensive spectroscopic analysis and X-ray crystallography. Compounds 1–4 are rare natural 12-membered cyclic trid ...
DOI:: 10.1021/acs.jnatprod.8b00829
: https://doi.org/10.1021/acs.jnatprod.8b00829

97. Concise Modular Synthesis of Thalassotalic Acids A–C

Author:: Joseph M. Schulz; Hunter T. Lanovoi; Amanda M. Ames; Phillip C. McKegg; James D. Patrone
Source:: Journal of natural products 2019 v.82 no.4 pp. 1045-1048
ISSN:: 1520-6025
Subject:: acids; aquatic bacteria; enzyme inhibition; inhibitory concentration 50; structure-activity relationships
Abstract:: ... The novel N-acyldehydrotyrosine analogues known as thalassotalic acids A–C were isolated from a marine bacterium by Deering et al. in 2016. These molecules were shown to have tyrosinase inhibition activity and thus are an attractive set of molecules for further study and optimization. To this end, a concise and modular synthesis has been devised and executed to produce thalassotalic acids A–C and ...
DOI:: 10.1021/acs.jnatprod.9b00028
: https://doi.org/10.1021/acs.jnatprod.9b00028

98. Configurational Variation of a Natural Compound within Its Source Species. The Unprecedented Case of Areolal in Piptothrix areolare

Author:: Héctor M. Arreaga-González; Gabriela Rodríguez-García; Rosa E. del Río; José A. Ferreira-Sereno; Hugo A. García-Gutiérrez; Carlos M. Cerda-García-Rojas; Pedro Joseph-Nathan; Mario A. Gómez-Hurtado
Source:: Journal of natural products 2019 v.82 no.12 pp. 3394-3400
ISSN:: 1520-6025
Subject:: X-ray diffraction; biochemical pathways; circular dichroism spectroscopy; entropy; environmental factors; humans; isolation techniques; nuclear magnetic resonance spectroscopy
Abstract:: ... The exceptional case of a natural compound that shows drastic absolute configuration variations within the same species was examined. Sequential samples of areolal (1) isolated from Piptothrix areolare showed dextrorotatory (ee 32%), almost racemic (ee 4%), levorotatory (ee 82%), and again dextrorotatory (ee 10%) values. Enantiomeric compositions of this epoxythymol derivative were determined from ...
DOI:: 10.1021/acs.jnatprod.9b00734
: https://doi.org/10.1021/acs.jnatprod.9b00734

99. Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa

Author:: Dawn Su-Yin Sim; Suerialoasan Navanesan; Kae-Shin Sim; Subramaniam Gurusamy; Siew-Huah Lim; Yun-Yee Low; Toh-Seok Kam
Source:: Journal of natural products 2019 v.82 no.4 pp. 850-858
ISSN:: 1520-6025
Subject:: Tabernaemontana; X-ray diffraction; active ingredients; alkaloids; anhydrides; ethanol; human cell lines; humans; inhibitory concentration 50; leaves; neoplasm cells; nuclear magnetic resonance spectroscopy; spectral analysis; tautomers
Abstract:: ... Examination of the EtOH extract of the leaves of the Malayan Tabernaemontana corymbosa resulted in the isolation of four new (1–4) and two known bisindole alkaloids (5, 6) of the Aspidosperma–Aspidosperma type. The structures of these alkaloids were determined based on analysis of the spectroscopic data (NMR and HRESIMS). X-ray diffraction analyses of the related bisindole alkaloids conophylline ( ...
DOI:: 10.1021/acs.jnatprod.8b00919
: https://doi.org/10.1021/acs.jnatprod.8b00919

100. Constituents from Nauclea latifolia with Anti-Haemophilus influenzae Type b Inhibitory Activities

Author:: Jean Jules Kezetas Bankeu; Donald Ulrich Kenou Kagho; Yannick Stéphane Fotsing Fongang; Rufin Marie Kouipou Toghueo; Brice Mittérant Mba’ning; Guy Raymond Tchouya Feuya; Fabrice Boyom Fekam; Jean Claude Tchouankeu; Silvère Augustin Ngouela; Norbert Sewald; Bruno Ndjakou Lenta; Muhammad Shaiq Ali
Source:: Journal of natural products 2019 v.82 no.9 pp. 2580-2585
ISSN:: 1520-6025
Subject:: Haemophilus influenzae; Sarcocephalus latifolius; antibacterial properties; ciprofloxacin; drugs; heartwood; in vitro studies; indole alkaloids; moieties; monoterpenoids; nuclear magnetic resonance spectroscopy; triterpenoids
Abstract:: ... Three previously undescribed indole alkaloids, named latifolianine A (1) and latifoliaindoles A and B (2 and 3), along with 10 known compounds (4–13), were isolated from the heartwood of Nauclea latifolia. Their structures were elucidated based on the analysis of their NMR and MS data. Latifolianine A (1) represents an unusual and unprecedented monoterpene indole alkaloid unit condensed with an ur ...
DOI:: 10.1021/acs.jnatprod.9b00463
: https://doi.org/10.1021/acs.jnatprod.9b00463

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1. (+)- and (−)-Alternarilactone A: Enantiomers with a Diepoxy-Cage-like Scaffold from an Endophytic Alternaria sp.

2. (−)-Epigallocatechin 3-O-Gallate as a New Approach for the Treatment of Visceral Leishmaniasis

3. 11-Aminostrychnine and N-(Strychnine-11-yl)propionamide: Synthesis, Configuration, and Pharmacological Evaluation at Glycine Receptors

4. 17-nor-Cephalotane-Type Diterpenoids from Cephalotaxus fortunei

5. 2-(Tetrahydrofuran-2-yl)acetic Acid and Ester Derivatives as Long-Range Pollinator Attractants in the Sexually Deceptive Orchid Cryptostylis ovata

6. A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea

7. A Near-Complete Series of Four Atropisomeric Jozimine A₂-Type Naphthylisoquinoline Dimers with Antiplasmodial and Cytotoxic Activities and Related Alkaloids from Ancistrocladus abbreviatus

8. A Systematic Cheminformatics Analysis of Functional Groups Occurring in Natural Products

9. Absolute Configuration and Biological Activities of Meroterpenoids from an Endophytic Fungus of Lycium barbarum

10. Absolute Configuration of Alkaloids from Uncaria longiflora through Experimental and Computational Approaches

11. Absolute Configuration of Bioactive Azaphilones from the Marine-Derived Fungus Pleosporales sp. CF09-1

12. Access to Natural Valparanes and Daucanes: Enantioselective Synthesis of (−)-Valpara-2,15-diene and (+)-Isodaucene

13. Acidiphilamides A–E, Modified Peptides as Autophagy Inhibitors from an Acidophilic Actinobacterium, Streptacidiphilus rugosus

14. Acrotrione: An Oxidized Xanthene from the Roots of Acronychia pubescens

15. Acylated Lignans Isolated from Brachanthemum gobicum and Their Trypanocidal Activity

16. Adiponectin-Secretion-Promoting Phenylethylchromones from the Agarwood of Aquilaria malaccensis

17. Albanitriles A–G: Antiprotozoal Polyacetylene Nitriles from a Mycale Marine Sponge

18. Alkaloids Purified from Aristotelia chilensis Inhibit the Human α3β4 Nicotinic Acetylcholine Receptor with Higher Potencies Compared with the Human α4β2 and α7 Subtypes

19. Alkaloids from the Branches and Leaves of Elaeocarpus angustifolius

20. Alopecuroides A–E, Matrine-Type Alkaloid Dimers from the Aerial Parts of Sophora alopecuroides

21. Alternatone A, an Unusual Perylenequinone-Related Compound from a Soft-Coral-Derived Strain of the Fungus Alternaria alternata

22. Ambiguity of NRPS Structure Predictions: Four Bidentate Chelating Groups in the Siderophore Pacifibactin

23. Amides and Flavonoids from the Fruit and Leaf Extracts of Melodorum siamensis

24. An Acetylenic Lipid from the New Zealand Ascidian Pseudodistoma cereum: Exemplification of an Improved Workflow for Determination of Absolute Configuration of Long-Chain 2-Amino-3-alkanols

25. An Effective Strategy for Identification of Highly Unstable Bacillaenes

26. An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray

27. An Orbitide from Ratibida columnifera Seed Containing 16 Amino Acid Residues

28. Anacolosins A–F and Corymbulosins X and Y, Clerodane Diterpenes from Anacolosa clarkii Exhibiting Cytotoxicity toward Pediatric Cancer Cell Lines

29. Antcamphorols A–K, Cytotoxic and ROS Scavenging Triterpenoids from Antrodia camphorata

30. Anti-Lymphangiogenic Alkaloids from the Zoanthid Zoanthus vietnamensis Collected in Taiwan

31. Anti-inflammatory Chalcone–Isoflavone Dimers and Chalcone Dimers from Caragana jubata

32. Anti-inflammatory Ellagitannins from Cleidion brevipetiolatum for the Treatment of Rheumatoid Arthritis

33. Anti-inflammatory Lathyrane Diterpenoids from Euphorbia lathyris

34. Anti-inflammatory Mono- and Dimeric Sorbicillinoids from the Marine-Derived Fungus Trichoderma reesei 4670

35. Anti-inflammatory Potential of Saponins from Aster tataricus via NF-κB/MAPK Activation

36. Anti-inflammatory Property of Imperatorin on Alveolar Macrophages and Inflammatory Lung Injury

37. Anti-inflammatory and α-Glucosidase Inhibitory Activities of Labdane and Norlabdane Diterpenoids from the Rhizomes of Amomum villosum

38. Anti-prion Butenolides and Diphenylpropanones from the Australian Ascidian Polycarpa procera

39. Antiangiogenic Activity of Compounds Isolated from Anarrhinum pedatum

40. Antibacterial 5α-Spirostane Saponins from the Fruit of Cordyline manners-suttoniae

41. Antibacterial Aromatic Polyketides Incorporating the Unusual Amino Acid Enduracididine

42. Antibacterial Salinaphthoquinones from a Strain of the Bacterium Salinispora arenicola Recovered from the Marine Sediments of St. Peter and St. Paul Archipelago, Brazil

43. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa

44. Antibacterial and Inhibitory Activities against Nitric Oxide Production of Coumaronochromones and Prenylated Isoflavones from Millettia extensa

45. Antifungal Phenylpropanoid Glycosides from Lippia rubella

46. Antifungal Sesquiterpenoids, Rhodocoranes, from Submerged Cultures of the Wrinkled Peach Mushroom, Rhodotus palmatus

47. Antimicrobial Chrysophaentin Analogs Identified from Laboratory Cultures of the Marine Microalga Chrysophaeum taylorii

48. Antimicrobial Dolabellanes and Atranones from a Marine-Derived Strain of the Toxigenic Fungus Stachybotrys chartarum

49. Antinociceptive Grayanane Diterpenoids from the Leaves of Pieris japonica

50. Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents

51. Antiplasmodial Diterpenoids from Psiadia arguta

52. Antiproliferative Acylated Glycerols from New Zealand Propolis

53. Antiproliferative Cardenolides from the Aerial Parts of Pergularia tomentosa

54. Antiproliferative Pterocarpans and Coumestans from Lespedeza bicolor

55. Antitrypanosomal Activity of Acetogenins Isolated from the Seeds of Porcelia macrocarpa Is Associated with Alterations in Both Plasma Membrane Electric Potential and Mitochondrial Membrane Potential

56. Antitumor Activity of Vanicoside B Isolated from Persicaria dissitiflora by Targeting CDK8 in Triple-Negative Breast Cancer Cells

57. Antiviral Compounds from Codiaeum peltatum Targeted by a Multi-informative Molecular Networks Approach

58. Aphidicolin Chemistry of the Deep-Sea-Derived Fungus Botryotinia fuckeliana MCCC 3A00494

59. Arabinoxyloglucan Oligosaccharides May Contribute to the Antiadhesive Properties of Porcine Urine after Cranberry Consumption

60. Aromaticity and Electron Density of Hypericin

61. Ascomylactams A–C, Cytotoxic 12- or 13-Membered-Ring Macrocyclic Alkaloids Isolated from the Mangrove Endophytic Fungus Didymella sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C

62. Asperpyridone A: An Unusual Pyridone Alkaloid Exerts Hypoglycemic Activity through the Insulin Signaling Pathway

63. Asperunguisins A–F, Cytotoxic Asperane Sesterterpenoids from the Endolichenic Fungus Aspergillus unguis

64. Astratides: Insulin-Modulating, Insecticidal, and Antifungal Cysteine-Rich Peptides from Astragalus membranaceus

65. Austalides, Osteoclast Differentiation Inhibitors from a Marine-Derived Strain of the Fungus Penicillium rudallense

66. Basimarols A, B, and C, Highly Oxygenated Pimarane Diterpenoids from Basilicum polystachyon

67. Benzophenone Compounds, from a Marine-Derived Strain of the Fungus Pestalotiopsis neglecta, Inhibit Proliferation of Pancreatic Cancer Cells by Targeting the MEK/ERK Pathway

68. Bialternacins A–F, Aromatic Polyketide Dimers from an Endophytic Alternaria sp.

69. Bifunctional Duocarmycin Analogues as Inhibitors of Protein Tyrosine Kinases

70. Bioactive Dimeric Acylphloroglucinols from the Mexican Fern Elaphoglossum paleaceum