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You searched for: Journal name Journal of natural products Remove constraint Journal name: Journal of natural products Publication year rev 7982-2018 Remove constraint Publication year rev: 7982-2018 Source 2018 v.81 no.4 Remove constraint Source: 2018 v.81 no.4
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1. Absolute Configuration and Pharmacology of the Poison Frog Alkaloid Phantasmidine

Author:
Richard W. Fitch; Barry B. Snider; Quan Zhou; Bruce M. Foxman; Anshul A. Pandya; Jerrel L. Yakel; Thao T. Olson; Nour Al-Muhtasib; Yingxian Xiao; Kevin D. Welch; Kip E. Panter
Source:
Journal of natural products 2018 v.81 no.4 pp. 1029-1035
ISSN:
1520-6025
Subject:
Epipedobates; agonists; carbon; enantiomers; enantioselectivity; liquid chromatography; mass spectrometry; nicotine; nicotinic receptors; pharmacology; poisonous frogs; therapeutics; toxicity
Abstract:
... Phantasmidine, a rigid congener of the well-known nicotinic acetylcholine receptor agonist epibatidine, is found in the same species of poison frog (Epipedobates anthonyi). Natural phantasmidine was found to be a 4:1 scalemic mixture, enriched in the (2aR,4aS,9aS) enantiomer by chiral-phase LC-MS comparison to the synthetic enantiomers whose absolute configurations were previously established by M ...
DOI:
10.1021/acs.jnatprod.8b00062
PubMed:
29671588
PubMed Central:
PMC7142328

2. Antibacterial Muraymycins from Mutant Strains of Streptomyces sp. NRRL 30471

Author:
Zheng Cui; Xiachang Wang; Stefan Koppermann; Jon S. Thorson; Christian Ducho; Steven G. Van Lanen
Source:
Journal of natural products 2018 v.81 no.4 pp. 942-948
ISSN:
1520-6025
Subject:
Aquifex; Escherichia coli; Staphylococcus aureus; Streptomyces; antibacterial properties; antibiotics; fatty acids; inhibitory concentration 50; mutagenesis; mutants; nuclear magnetic resonance spectroscopy; nucleosides; spectral analysis
Abstract:
... Muraymycins are nucleoside antibiotics isolated from Streptomyces sp. NRRL 30471 and several mutant strains thereof that were generated by random, chemical mutagenesis. Reinvestigation of two mutant strains using new media conditions led to the isolation of three new muraymycin congeners, named B8, B9, and C6 (1–3), as well as a known muraymycin, C1. Structures of the compounds were elucidated by ...
DOI:
10.1021/acs.jnatprod.7b01054
PubMed:
29553733
PubMed Central:
PMC6434714

3. Bioactive α-Pyrone Derivatives from the Endolichenic Fungus Dothideomycetes sp. EL003334

Author:
Gil Soo Kim; Wonmin Ko; Jong Won Kim; Min-Hye Jeong; Sung-Kyun Ko; Jae-Seoun Hur; Hyuncheol Oh; Jae-Hyuk Jang; Jong Seog Ahn
Source:
Journal of natural products 2018 v.81 no.4 pp. 1084-1088
ISSN:
1520-6025
Subject:
Dothideomycetes; fungi; gene expression; inducible nitric oxide synthase; inhibitory concentration 50; interleukin-6; lipopolysaccharides; messenger RNA; nitric oxide; prostaglandin synthase; protein synthesis; spectral analysis; tumor necrosis factor-alpha
Abstract:
... Two new α-pyrones, dothideopyrones E (1) and F (2), were isolated from a culture of the endolichenic fungus Dothideomycetes sp. EL003334. Their structures were elucidated by spectroscopic data analysis. Their absolute configurations were established by the modified Mosher’s method. Compound 2 inhibited nitric oxide (NO) production with IC₅₀ values of 15.0 ± 2.8 μM in lipopolysaccharide (LPS)-induc ...
DOI:
10.1021/acs.jnatprod.7b01022

4. Bioactivity-Based Molecular Networking for the Discovery of Drug Leads in Natural Product Bioassay-Guided Fractionation

Author:
Louis-Félix Nothias; Mélissa Nothias-Esposito; Ricardo da Silva; Mingxun Wang; Ivan Protsyuk; Zheng Zhang; Abi Sarvepalli; Pieter Leyssen; David Touboul; Jean Costa; Julien Paolini; Theodore Alexandrov; Marc Litaudon; Pieter C. Dorrestein
Source:
Journal of natural products 2018 v.81 no.4 pp. 758-767
ISSN:
1520-6025
Subject:
Euphorbia; active ingredients; antiviral agents; bioactive compounds; bioactive properties; bioassays; bioinformatics; fractionation; prediction; tandem mass spectrometry; therapeutics
Abstract:
... It is a common problem in natural product therapeutic lead discovery programs that despite good bioassay results in the initial extract, the active compound(s) may not be isolated during subsequent bioassay-guided purification. Herein, we present the concept of bioactive molecular networking to find candidate active molecules directly from fractionated bioactive extracts. By employing tandem mass ...
DOI:
10.1021/acs.jnatprod.7b00737

5. Coculture of Two Developmental Stages of a Marine-Derived Aspergillus alliaceus Results in the Production of the Cytotoxic Bianthrone Allianthrone A

Author:
P. E. Mandelare; D. A. Adpressa; E. N. Kaweesa; L. N. Zakharov; S. Loesgen
Source:
Journal of natural products 2018 v.81 no.4 pp. 1014-1022
ISSN:
1520-6025
Subject:
Aspergillus alliaceus; X-ray diffraction; anamorphs; anthraquinones; antibiotics; anticarcinogenic activity; cell lines; coculture; colorectal neoplasms; cytotoxicity; developmental stages; diastereomers; fungi; melanoma; nuclear magnetic resonance spectroscopy; ochratoxins; optical properties; sclerotia; secondary metabolites; sexual development; spectral analysis; teleomorphs; toxicity testing; vegetative growth
Abstract:
... The genetically encoded, small-molecule chemical diversity of filamentous fungi is still largely unexplored and represents an attractive source for the discovery of new compounds. Here we report the production of new chlorinated bianthrones from coculture of two different developmental stages, or morphs, of a marine alga-derived Aspergillus alliaceus (teleomorph: Petromyces alliaceus) strain. The ...
DOI:
10.1021/acs.jnatprod.8b00024

6. Concise Total Synthesis of (±)-Deguelin and (±)-Tephrosin Using a Vinyl Iodide as a Key Building Block

Author:
Shengtao Xu; Guangyu Wang; Feijie Xu; Wenlong Li; Aijun Lin; Hequan Yao; Jinyi Xu
Source:
Journal of natural products 2018 v.81 no.4 pp. 1055-1059
ISSN:
1520-6025
Subject:
antineoplastic agents; hydroxylation; organoiodine compounds
Abstract:
... A concise and protecting-group-free total synthesis of the antiproliferative natural product (±)-deguelin (2) was accomplished in four steps and 62% overall yield from commercially available precursors. The key transformation employed a vinyl iodide as the pivotal building block to construct the 4-acylchromene substructure present in deguelin. Subsequent Cu₂O-mediated α-hydroxylation of deguelin ( ...
DOI:
10.1021/acs.jnatprod.7b00794

7. Drimane Sesquiterpenoids Noncompetitively Inhibit Human α4β2 Nicotinic Acetylcholine Receptors with Higher Potency Compared to Human α3β4 and α7 Subtypes

Author:
Hugo R. Arias; Dominik Feuerbach; Bernd Schmidt; Matthias Heydenreich; Cristian Paz; Marcelo O. Ortells
Source:
Journal of natural products 2018 v.81 no.4 pp. 811-817
ISSN:
1520-6025
Subject:
Drimys winteri; calcium; humans; inhibitory concentration 50; ligands; medicinal properties; molecular models; nicotinic receptors; sesquiterpenoids; spectroscopy; structure-activity relationships; trees
Abstract:
... The drimane sesquiterpenoids drimenin, cinnamolide, dendocarbin A, and polygodial were purified from the Canelo tree (Drimys winteri) and chemically characterized by spectroscopic methods. The pharmacological activity of these natural compounds were determined on hα4β2, hα3β4, and hα7 nicotinic acetylcholine receptors (AChRs) by Ca²⁺ influx measurements. The results established that drimane sesqui ...
DOI:
10.1021/acs.jnatprod.7b00893

8. An Efficient Method for Determining the Relative Configuration of Furofuran Lignans by 1H NMR Spectroscopy

Author:
Si-Yuan Shao; Ya-Nan Yang; Zi-Ming Feng; Jian-Shuang Jiang; Pei-Cheng Zhang
Source:
Journal of natural products 2018 v.81 no.4 pp. 1023-1028
ISSN:
1520-6025
Subject:
data collection; lignans; moieties; nuclear magnetic resonance spectroscopy
Abstract:
... An efficient ¹H NMR spectroscopic approach for determining the relative configurations of lignans with a 7,9′:7′,9-diepoxy moiety has been established. Using the chemical shift differences of H₂-9 and H₂-9′ (ΔδH₋₉ and ΔδH₋₉′), the configurations of 8-H and 8-OH furofuran lignans can be rapidly and conveniently determined. The rule is applicable for data acquired in DMSO-d₆, methanol-d₄, or CDCl₃. ...
DOI:
10.1021/acs.jnatprod.8b00044

9. Estrogen Receptor (ER) Subtype Selectivity Identifies 8-Prenylapigenin as an ERβ Agonist from Glycyrrhiza inflata and Highlights the Importance of Chemical and Biological Authentication

Author:
Atieh Hajirahimkhan; Obinna Mbachu; Charlotte Simmler; Sarah G. Ellis; Huali Dong; Dejan Nikolic; David C. Lankin; Richard B. van Breemen; Shao-Nong Chen; Guido F. Pauli; Birgit M. Dietz; Judy L. Bolton
Source:
Journal of natural products 2018 v.81 no.4 pp. 966-975
ISSN:
1520-6025
Subject:
Glycyrrhiza glabra; Glycyrrhiza inflata; agonists; alkaline phosphatase; breast neoplasms; estrogen receptors; estrogenic properties; estrogens; fractionation; licorice; neoplasm cells; postmenopause; quality control; quantitative analysis; risk; therapeutics; women
Abstract:
... Postmenopausal women are increasingly using botanicals for menopausal symptom relief due to the increased breast cancer risk associated with traditional estrogen therapy. The deleterious effects of estrogens are associated with estrogen receptor (ER)α-dependent proliferation, while ERβ activation could enhance safety by opposing ERα effects. Three medicinal licorice species, Glycyrrhiza glabra (G. ...
DOI:
10.1021/acs.jnatprod.7b01070
PubMed:
29641206
PubMed Central:
PMC5928484

10. Exploring an Artificial Metabolic Route in Fusarium sporotrichioides: Production and Characterization of 7-Hydroxy T-2 Toxin

Author:
Kentaro Kamata; Hiroki Sato; Kazuyuki Maeda; Kazuo Furihata; Shunichi Aikawa; Kentaro Adachi; Akira Tanaka; Takeshi Tokai; Yuichi Nakajima; Yasuhiko Yoshida; Shohei Sakuda; Makoto Kimura; Naoko Takahashi-Ando
Source:
Journal of natural products 2018 v.81 no.4 pp. 1041-1044
ISSN:
1520-6025
Subject:
Fusarium sporotrichioides; T-2 toxin; biosynthesis; enzymes; fungi; metabolic engineering; mutants; secondary metabolites; substrate specificity; toxicity
Abstract:
... An artificial metabolic route to an unnatural trichothecene was designed by taking advantage of the broad substrate specificities of the T-2 toxin biosynthetic enzymes of Fusarium sporotrichioides. By feeding 7-hydroxyisotrichodermin, a shunt pathway metabolite of F. graminearum, to a trichodiene synthase-deficient mutant of F. sporotrichioides, 7-hydroxy T-2 toxin (1) was obtained as the final me ...
DOI:
10.1021/acs.jnatprod.7b00398

11. Glycosides of the Neurotoxin Tutin in Toxic Honeys Are from Coriaria arborea Phloem Sap, Not Insect Metabolism

Author:
Oliver C. Watkins; Nigel I. Joyce; Nick Gould; Nigel B. Perry
Source:
Journal of natural products 2018 v.81 no.4 pp. 1116-1120
ISSN:
1520-6025
Subject:
Coriaria; bees; glycosides; honey; honeydew; leaves; liquid chromatography; mass spectrometry; metabolism; neurotoxins; phloem; sap; sucrose; toxicity
Abstract:
... Some honeys contain the neurotoxin tutin (1) plus hyenanchin (2), 2-(β-d-glucopyranosyl)tutin (3), and 2-[6′-(α-d-glucopyranosyl)-β-d-glucopyranosyl]tutin (4). These honeys are made by bees collecting honeydew from passionvine hoppers feeding on the sap of tutu plants (Coriaria spp.). We report a LC-MS study showing that all these picrotoxanes are of plant, not insect, origin. Hyenanchin was barel ...
DOI:
10.1021/acs.jnatprod.8b00120

12. Identification of Gibberellic Acid Derivatives That Deregulate Cholesterol Metabolism in Prostate Cancer Cells

Author:
Folake A. Egbewande; Martin C. Sadowski; Claire Levrier; Kaylyn D. Tousignant; Jonathan M. White; Mark J. Coster; Colleen C. Nelson; Rohan A. Davis
Source:
Journal of natural products 2018 v.81 no.4 pp. 838-845
ISSN:
1520-6025
Subject:
X-ray diffraction; cholesterol; cholesterol metabolism; cytotoxicity; diterpenoids; gibberellic acid; hydrogen bonding; molecular weight; neoplasm cells; nuclear magnetic resonance spectroscopy; prostatic neoplasms
Abstract:
... The naturally occurring pentacyclic diterpenoid gibberellic acid (1) was used in the generation of a drug-like amide library using parallel-solution-phase synthesis. Prior to the synthesis, a virtual library was generated and prioritized based on drug-like physicochemical parameters such as log P, hydrogen bond donor/acceptor counts, and molecular weight. The structures of the synthesized analogue ...
DOI:
10.1021/acs.jnatprod.7b00929

13. Imidazole Alkaloids and Their Zinc Complexes from the Calcareous Marine Sponge Leucetta chagosensis

Author:
Wei-Zhuo Tang; Zhong-Zhen Yang; Wei Wu; Jie Tang; Fan Sun; Shu-Ping Wang; Chun-Wei Cheng; Fan Yang; Hou-Wen Lin
Source:
Journal of natural products 2018 v.81 no.4 pp. 894-900
ISSN:
1520-6025
Subject:
Porifera; breast neoplasms; cell lines; cytotoxicity; humans; imidazole alkaloids; inhibitory concentration 50; interleukin-6; neoplasm cells; nitrogen; spectroscopy; stem cells; zinc; South China Sea
Abstract:
... Five new imidazole derivatives (1–5), together with eight related known alkaloids, were isolated from a calcareous marine sponge, Leucetta chagosensis, collected from the South China Sea. Their structures were fully characterized by spectroscopic methods. Structurally, 1 possesses an unusual skeleton featuring imidazole and oxazolone rings linked via a nitrogen atom, whereas 2 bears an intriguing ...
DOI:
10.1021/acs.jnatprod.7b01006

14. Isolation, Characterization, and Structure–Activity Relationship Analysis of Abietane Diterpenoids from Callicarpa bodinieri as Spleen Tyrosine Kinase Inhibitors

Author:
Jun-Bo Gao; Shuang-Jing Yang; Zi-Ru Yan; Xing-Jie Zhang; De-Bing Pu; Li-Xia Wang; Xiao-Li Li; Rui-Han Zhang; Wei-Lie Xiao
Source:
Journal of natural products 2018 v.81 no.4 pp. 998-1006
ISSN:
1520-6025
Subject:
Callicarpa bodinieri; Oriental traditional medicine; acids; branches; diterpenoids; enzyme inhibitors; inhibitory concentration 50; leaves; molecular models; non-specific protein-tyrosine kinase; nuclear magnetic resonance spectroscopy; pharmacology; structure-activity relationships; therapeutics
Abstract:
... Species belonging to the genus Callicarpa are used traditionally in Chinese medicine for the treatment of inflammation, rheumatism, and pain. Investigation of the leaves and twigs of Callicarpa bodinieri resulted in the isolation of nine new abietane diterpenoids, bodinieric acids A–I (1–9), along with six known compounds (10–15). The structures of 1–9 were elucidated on the basis of the interpret ...
DOI:
10.1021/acs.jnatprod.7b01082

15. Lichen Biosynthetic Gene Clusters. Part I. Genome Sequencing Reveals a Rich Biosynthetic Potential

Author:
Robert L. Bertrand; Mona Abdel-Hameed; John L. Sorensen
Source:
Journal of natural products 2018 v.81 no.4 pp. 723-731
ISSN:
1520-6025
Subject:
Cladonia; algae; antibiotics; biosynthesis; fungi; lichens; ligases; metabolome; multigene family; polyketide synthases; secondary metabolites; sequence analysis; symbionts
Abstract:
... Lichens are symbionts of fungi and algae that produce diverse secondary metabolites with useful properties. Little is known of lichen natural product biosynthesis because of the challenges of working with lichenizing fungi. We describe the first attempt to comprehensively profile the genetic secondary metabolome of a lichenizing fungus. An Illumina platform combined with the Antibiotics and Second ...
DOI:
10.1021/acs.jnatprod.7b00769

16. Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities

Author:
Dieudonné Tshitenge Tshitenge; Doris Feineis; Virima Mudogo; Marcel Kaiser; Reto Brun; Ean-Jeong Seo; Thomas Efferth; Gerhard Bringmann
Source:
Journal of natural products 2018 v.81 no.4 pp. 918-933
ISSN:
1520-6025
Subject:
Plasmodium falciparum; alkaloids; antiparasitic agents; cytotoxicity; humans; leukemia; malaria; moieties; multiple drug resistance; naphthalene; neoplasm cells; optical isomerism; parasites
Abstract:
... Four new dimeric naphthylisoquinoline alkaloids, michellamine A₅ (2) and mbandakamines C–E (4–6), were isolated from the Congolese plant Ancistrocladus ealaensis, along with the known dimer mbandakamine A (3). They represent constitutionally unsymmetric dimers, each consisting of two 5,8′-coupled naphthylisoquinoline monomers. While the molecular halves of michellamine A₅ (2) are linked via C-6′ o ...
DOI:
10.1021/acs.jnatprod.7b01041

17. Microporenic Acids A–G, Biofilm Inhibitors, and Antimicrobial Agents from the Basidiomycete Microporus Species

Author:
Clara Chepkirui; Kamila T. Yuyama; Lucy A. Wanga; Cony Decock; Josphat C. Matasyoh; Wolf-Rainer Abraham; Marc Stadler
Source:
Journal of natural products 2018 v.81 no.4 pp. 778-784
ISSN:
1520-6025
Subject:
Candida albicans; Gram-positive bacteria; Polyporales; Staphylococcus aureus; anti-infective agents; antibacterial properties; antibiotic resistance; antifungal properties; biofilm; diterpenoids; dose response; forests; isocitric acid; yeasts; Kenya
Abstract:
... The need for effective compounds to combat antimicrobial resistance and biofilms which play important roles in human infections continues to pose a major health challenge. Seven previously undescribed acyclic diterpenes linked to isocitric acid by an ether linkage, microporenic acids A–G (1–7), were isolated from the cultures of a hitherto undescribed species of the genus Microporus (Polyporales, ...
DOI:
10.1021/acs.jnatprod.7b00764

18. Miuramides A and B, Trisoxazole Macrolides from a Mycale sp. Marine Sponge That Induce a Protrusion Phenotype in Cultured Mammalian Cells

Author:
Rei Suo; Kentaro Takada; Hisanori Kohtsuka; Yuji Ise; Shigeru Okada; Shigeki Matsunaga
Source:
Journal of natural products 2018 v.81 no.4 pp. 1108-1112
ISSN:
1520-6025
Subject:
Mycale; cytotoxicity; derivatization; macrolides; mammals; phenotype; screening; spectral analysis
Abstract:
... Morphology-guided cell-based screening of the extract of a Mycale sp. marine sponge led to the isolation of two trisoxazole macrolides, miuramides A (1) and B (2), which induced characteristic morphological changes in 3Y1 cells. The structure of 1 including absolute configuration was elucidated by a combination of the analysis of spectroscopic data, derivatization, and degradation. Both compounds ...
DOI:
10.1021/acs.jnatprod.8b00101

19. Nitric Oxide Inhibitory Sesquiterpenoids and Its Dimers from Artemisia freyniana

Author:
Chen Zhang; Ran Wen; Xiao-Li Ma; Ke-Wu Zeng; Yang Xue; Pu-Ming Zhang; Ming-Bo Zhao; Yong Jiang; Guo-Qing Liu; Peng-Fei Tu
Source:
Journal of natural products 2018 v.81 no.4 pp. 866-878
ISSN:
1520-6025
Subject:
Artemisia; X-ray diffraction; biochemical pathways; inhibitory concentration 50; macrophages; nitric oxide; nuclear magnetic resonance spectroscopy; sesquiterpenoids; spectral analysis
Abstract:
... Two new disesquiterpenoids (1 and 2) and 11 new (3–13) and 10 known (14–23) sesquiterpenoids were isolated from the whole plants of Artemisia freyniana. Their structures were elucidated by spectroscopic data analysis and comparison with published NMR data. The absolute configurations of the new isolates (1–13) were assigned based on single-crystal X-ray diffraction data and comparison of the exper ...
DOI:
10.1021/acs.jnatprod.7b00947

20. Penicilindoles A–C, Cytotoxic Indole Diterpenes from the Mangrove-Derived Fungus Eupenicillium sp. HJ002

Author:
Cai-Juan Zheng; Meng Bai; Xue-Ming Zhou; Guo-Lei Huang; Tai-Ming Shao; You-Ping Luo; Zhi-Gang Niu; Yan-Yan Niu; Guang-Ying Chen; Chang-Ri Han
Source:
Journal of natural products 2018 v.81 no.4 pp. 1045-1049
ISSN:
1520-6025
Subject:
Eupenicillium; X-ray diffraction; antibacterial properties; anticarcinogenic activity; copper; cytotoxicity; diterpenoids; fungi; human cell lines; humans; inhibitory concentration 50; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... Three new indole diterpenes, penicilindoles A–C (1–3), were isolated from the mangrove-derived fungus Eupenicillium sp. HJ002. Their planar structures and absolute configurations were determined by interpretation of NMR spectroscopic data, HR-ESIMS, and X-ray diffraction analysis using Cu Kα radiation. The cytotoxic and antibacterial activities were evaluated in vitro; penicilindole A (1) showed c ...
DOI:
10.1021/acs.jnatprod.7b00673