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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 Text availability Citation in PubAg Remove constraint Text availability: Citation in PubAg
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1. 1,4-Benzodioxane Lignans: An Efficient, Asymmetric Synthesis of Flavonolignans and Study of Neolignan Cytotoxicity and Antiviral Profiles

Author:
Lisa I. Pilkington; Jessica Wagoner; Toni Kline; Stephen J. Polyak; David Barker
Source:
Journal of natural products 2018 v.81 no.12 pp. 2630-2637
ISSN:
1520-6025
Subject:
alcohols; antiviral properties; bioactive compounds; cytotoxicity; dioxane; lignans; moieties
Abstract:
... 1,4-Benzodioxane lignans are a class of bioactive compounds that have received much attention through the years. Herein research pertaining to both 1,4-benzodioxane flavonolignans and 1,4-benzodioxane neolignans is presented. A novel synthesis of both traditional 1,4-benzodioxane flavonolignans and 3-deoxyflavonolignans is described. The antiviral and cytotoxic activities of 1,4-benzodioxane neoli ...
DOI:
10.1021/acs.jnatprod.8b00416

2. 3,4-seco-Norclerodane Diterpenoids from the Roots of Polyalthia laui

Author:
Zhang-Xin Yu; Cai-Juan Zheng; Guang-Ying Chen; Rong-Li Huang; Xue-Ming Zhou; Zhi-Gang Niu; Xiao-Bao Li; Chang-Ri Han; Xiao-Ping Song
Source:
Journal of natural products 2018 v.82 no.1 pp. 27-34
ISSN:
1520-6025
Subject:
Polyalthia; X-ray diffraction; antiretroviral properties; biosynthesis; circular dichroism spectroscopy; diterpenoids; median effective concentration; nuclear magnetic resonance spectroscopy; roots; spectral analysis
Abstract:
... Ten new clerodane diterpenoids, polylauioids A–J (1–10), and five known analogues (11–15) were isolated from the roots of Polyalthia laui. Among the new compounds, 3 and 8 are artifacts. The structures were elucidated using spectroscopic methods and by comparison with published NMR spectroscopic data. The absolute configurations of 4, 5, and 7 were defined based on single-crystal X-ray diffraction ...
DOI:
10.1021/acs.jnatprod.8b00243

3. 7α,20-Epoxy-ent-kaurane Diterpenoids from the Aerial Parts of Isodon pharicus

Author:
Zheng-Xi Hu; Miao Liu; Wei-Guang Wang; Xiao-Nian Li; Kun Hu; Xing-Ren Li; Xue Du; Yong-Hui Zhang; Pema-Tenzin Puno; Han-Dong Sun
Source:
Journal of natural products 2018 v.81 no.1 pp. 106-116
ISSN:
1520-6025
Subject:
X-ray diffraction; aerial parts; cell lines; chemical constituents of plants; circular dichroism spectroscopy; cytotoxicity; diterpenoids; ethyl acetate; inhibitory concentration 50; neoplasm cells; spectral analysis
Abstract:
... A phytochemical investigation of an ethyl acetate extract of the aerial parts of Isodon pharicus led to the isolation of 21 new 7α,20-epoxy-ent-kaurane diterpenoids, pharicins C–W (1–21), and 29 known (22–50) analogues. The structural characterization of 1–21 and assignment of their relative configurations were accomplished by spectroscopic data interpretation, while the structures of 1 and 16 wer ...
DOI:
10.1021/acs.jnatprod.7b00723

4. A Bowman–Birk Inhibitor from the Seeds of Luetzelburgia auriculata Inhibits Staphylococcus aureus Growth by Promoting Severe Cell Membrane Damage

Author:
Thiago F. Martins; Ilka M. Vasconcelos; Rodolpho G. G. Silva; Fredy D. A. Silva; Pedro F. N. Souza; Anna L. N. Varela; Louise M. Albuquerque; Jose T. A. Oliveira
Source:
Journal of natural products 2018 v.81 no.7 pp. 1497-1507
ISSN:
1520-6025
Subject:
Bowman-Birk inhibitor; Luetzelburgia; Staphylococcus aureus; antibacterial properties; bacteria; boiling; cell membranes; chymotrypsin; death; health services; multiple drug resistance; pH; public health; scanning electron microscopy; seeds; trypsin
Abstract:
... Staphylococcus aureus is a multidrug-resistant bacterium responsible for several cases of hospital-acquired infections, which constitute a global public health problem. The introduction of new healthcare strategies and/or the discovery of molecules capable of inhibiting the growth or killing S. aureus would have a huge impact on the treatment of S. aureus-mediated diseases. Herein, a Bowman–Birk p ...
DOI:
10.1021/acs.jnatprod.7b00545

5. A Pair of Enantiomeric Bis-seco-abietane Diterpenoids from Cryptomeria fortunei

Author:
Lu Feng; Attila Mándi; Chunping Tang; Tibor Kurtán; Shuai Tang; Chang-Qiang Ke; Ning Shen; Ge Lin; Sheng Yao; Yang Ye
Source:
Journal of natural products 2018 v.81 no.12 pp. 2667-2672
ISSN:
1520-6025
Subject:
Cryptomeria; X-ray diffraction; bark; circular dichroism spectroscopy; cytotoxicity; diterpenoids; enantiomers; high performance liquid chromatography; human cell lines; neoplasm cells; quinones; spectral analysis
Abstract:
... (±)-Cryptomeriolide, a pair of racemic bis-seco-abietane diterpenoids, were isolated from the bark of Cryptomeria fortunei. The separation of enantiomers was achieved by using chiral stationary phase HPLC. Their structures including the absolute configuration and conformations in solution and solid state were determined by extensive analysis of spectroscopic data, single-crystal X-ray diffraction, ...
DOI:
10.1021/acs.jnatprod.8b00482

6. A Series of Enthalpically Optimized Docetaxel Analogues Exhibiting Enhanced Antitumor Activity and Water Solubility

Author:
Yun-Tao Ma; Yanting Yang; Pei Cai; De-Yang Sun; Pedro A. Sánchez-Murcia; Xiao-Ying Zhang; Wen-Qiang Jia; Lei Lei; Mengqi Guo; Federico Gago; Hongbo Wang; Wei-Shuo Fang
Source:
Journal of natural products 2018 v.81 no.3 pp. 524-533
ISSN:
1520-6025
Subject:
alcohols; antineoplastic activity; binding capacity; drug resistance; hydrogen bonding; hydrophobicity; mice; microtubules; moieties; molecular models; neoplasm cells; ovarian neoplasms; paclitaxel; water solubility
Abstract:
... A dual-purpose strategy aimed at enhancing the binding affinity for microtubules and improving the water solubility of docetaxel led to the design and synthesis of a series of C-2- and C-3′-modified analogues. Both aims were realized when the C-3′ phenyl group present in docetaxel was replaced with a propargyl alcohol. The resulting compound, 3f, was able to overcome drug resistance in cultured P- ...
DOI:
10.1021/acs.jnatprod.7b00857

7. A Steroid-Type Antioxidant Targeting the Keap1/Nrf2/ARE Signaling Pathway from the Soft Coral Dendronephthya gigantea

Author:
Jianzhang Wu; Yiyuan Xi; Lili Huang; Ge Li; Qiqi Mao; Chengyan Fang; Tizhuang Shan; Wei Jiang; Min Zhao; Wenfei He; Jianyong Dong; Xiubao Li; Peihong Qiu; Pengcheng Yan
Source:
Journal of natural products 2018 v.81 no.11 pp. 2567-2575
ISSN:
1520-6025
Subject:
antioxidants; corals; signal transduction; spectral analysis; steroids; South China Sea
Abstract:
... Four new steroids, named 7-dehydroerectasteroid F (1), 11α-acetoxyarmatinol A (2), 22,23-didehydroarmatinol A (3), and 3-O-acetylhyrtiosterol (4), together with 11 previously described analogues, were isolated from a South China Sea collection of the soft coral Dendronephthya gigantea. The structures of the new steroids were elucidated by comprehensive spectroscopic analysis and by comparison with ...
DOI:
10.1021/acs.jnatprod.8b00728

8. Abietane Diterpenoids from the Roots of Clerodendrum trichotomum and Their Nitric Oxide Inhibitory Activities

Author:
Hai-Jun Hu; Yue Zhou; Zhu-Zhen Han; Yan-Hong Shi; Shu-Sheng Zhang; Zheng-Tao Wang; Li Yang
Source:
Journal of natural products 2018 v.81 no.7 pp. 1508-1516
ISSN:
1520-6025
Subject:
Clerodendrum trichotomum; X-ray diffraction; diterpenoids; inhibitory concentration 50; nitric oxide; roots; structure-activity relationships
Abstract:
... Twelve new abietane diterpenoids (1–12) and 31 known analogues (13–43) were isolated from a medicinal Chinese herb, Clerodendrum trichotomum Thunberg. The absolute configurations of 1–3 were established on the basis of ECD and X-ray crystallography data, whereas that of 4 was elucidated by comparison of experimental and calculated ECD data. Eight diterpenoids, 15,16-dehydroteuvincenone G (1), tric ...
DOI:
10.1021/acs.jnatprod.7b00814

9. Absolute Configuration of the Cytotoxic Marine Alkaloid Monanchocidin A

Author:
Larisa K. Shubina; Tatyana N. Makarieva; Alla G. Guzii; Vladimir A. Denisenko; Roman S. Popov; Pavel S. Dmitrenok; Valentin A. Stonik
Source:
Journal of natural products 2018 v.81 no.4 pp. 1113-1115
ISSN:
1520-6025
Subject:
Porifera; alcohols; alkaloids; cytotoxicity; guanidines
Abstract:
... The absolute configuration of the cytotoxic guanidine alkaloid monanchocidin A with 11 stereogenic centers from the marine sponge Monanchora pulchra was determined as 5R, 8S, 10S, 13R, 14S, 15R, 19R, 23R, 37S, 42S, 43R after extensive reductive degradation and conversion of the resulting alcohols to MTPA derivatives. ...
DOI:
10.1021/acs.jnatprod.8b00105

10. Absolute Configurations and Bioactivities of Guaiane-Type Sesquiterpenoids Isolated from Pogostemon cablin

Author:
Qin-Mei Zhou; Ming-Hua Chen; Xiao-Hong Li; Cheng Peng; Da-Sheng Lin; Xiao-Nian Li; Yang He; Liang Xiong
Source:
Journal of natural products 2018 v.81 no.9 pp. 1919-1927
ISSN:
1520-6025
Subject:
Candida albicans; Pogostemon cablin; X-ray diffraction; antifungal properties; aorta; essential oils; median effective concentration; minimum inhibitory concentration; neuroprotective effect; rats; sesquiterpenoids; spectral analysis; vasodilator agents
Abstract:
... Seven novel guaiane sesquiterpenoids (1–7) and three known seco-guaianes were isolated from the volatile oil of Pogostemon cablin. Their structures including absolute configurations were determined by spectroscopic analyses, a modified Mosher’s method, and X-ray diffraction and ECD data. The results indicated that the ECD Cotton effects arising from one or two nonconjugated olefinic chromophores c ...
DOI:
10.1021/acs.jnatprod.7b00690

11. Absolute Configurations of Naturally Occurring [5]- and [3]-Ladderanoic Acids: Isolation, Chiroptical Spectroscopy, and Crystallography

Author:
Vijay Raghavan; Jordan L. Johnson; Donald F. Stec; Bongkeun Song; Grzegorz Zajac; Malgorzata Baranska; Constance M. Harris; Nathan D. Schley; Prasad L. Polavarapu; Thomas M. Harris
Source:
Journal of natural products 2018 v.81 no.12 pp. 2654-2666
ISSN:
1520-6025
Subject:
X-ray diffraction; anaerobic ammonium oxidation; biomass; bioreactors; crystallography; esters; high performance liquid chromatography; optical properties; quantum mechanics; spectroscopy
Abstract:
... We have isolated mixtures of [5]- and [3]-ladderanoic acids 1a and 2a from the biomass of an anammox bioreactor and have separated the acids and their phenacyl esters for the first time by HPLC. The absolute configurations of the naturally occurring acids and their phenacyl esters are assigned as R at the site of side-chain attachment by comparison of experimental specific rotations with correspon ...
DOI:
10.1021/acs.jnatprod.8b00458

12. Abyssomicin Monomers and Dimers from the Marine-Derived Streptomyces koyangensis SCSIO 5802

Author:
Hongbo Huang; Yongxiang Song; Xin Li; Xin Wang; Chunyao Ling; Xiangjing Qin; Zhenbin Zhou; Qinglian Li; Xiaoyi Wei; Jianhua Ju
Source:
Journal of natural products 2018 v.81 no.8 pp. 1892-1898
ISSN:
1520-6025
Subject:
Streptomyces; Vesiculovirus; antibiotic resistance; biosynthesis; methicillin; methicillin-resistant Staphylococcus aureus
Abstract:
... Three new abyssomicin monomers designated neoabyssomicins D (1), E (2), and A2 (3) and the two dimeric neoabyssomicins F (4) and G (5) were discovered from the marine-derived Streptomyces koyangensis SCSIO 5802, and their structures rigorously elucidated. Neoabyssomicin D (1) possesses an unprecedented 8/5/5/7 ring skeleton, the biosynthesis of which (as well as 2) is proposed herein. Additionally ...
DOI:
10.1021/acs.jnatprod.8b00448

13. Active Natural Product Scaffolds against Trypanosomatid Parasites: A Review

Author:
Peter E. Cockram; Terry K. Smith
Source:
Journal of natural products 2018 v.81 no.9 pp. 2138-2154
ISSN:
1520-6025
Subject:
adverse effects; animal and human health; bioactive compounds; drugs; parasites; therapeutics; tropical diseases
Abstract:
... Neglected tropical diseases caused by trypanosomatid parasites are a continuing and escalating problem, which devastate the less economically developed cultures in countries in which they are endemic by impairing both human and animal health. Current drugs for these diseases are regarded as out-of-date and expensive, with unacceptable side-effects and mounting parasite resistance, meaning there is ...
DOI:
10.1021/acs.jnatprod.8b00159

14. Additional Insights into Hypericum perforatum Content: Isolation, Total Synthesis, and Absolute Configuration of Hyperbiphenyls A and B from Immunomodulatory Root Extracts

Author:
Dimitri Bréard; Guillaume Viault; Marie-Charlotte Mezier; Sylvain Pagie; Antoine Bruguière; Pascal Richomme; Béatrice Charreau; Séverine Derbré
Source:
Journal of natural products 2018 v.81 no.8 pp. 1850-1859
ISSN:
1520-6025
Subject:
Hypericum perforatum; bioactive properties; biochemical compounds; biomimetics; biphenyl; chemical constituents of plants; endothelial cells; esters; major histocompatibility complex; nuclear magnetic resonance spectroscopy; stereoselectivity; xanthone
Abstract:
... Phytochemical investigation of the root extracts of Hypericum perforatum led to the isolation of two biphenyl derivatives named hyperbiphenyls A and B (1 and 2) and four known xanthones (3–6). These structures were elucidated by spectroscopic and spectrometric methods including UV, NMR, and HRMS. The absolute configuration of the biphenyl derivatives was defined by two different approaches: biomim ...
DOI:
10.1021/acs.jnatprod.8b00325

15. Advanced NMR-Based Structural Investigation of Glucosinolates and Desulfoglucosinolates

Author:
Nada Ibrahim; Ingrid Allart-Simon; Gina R. De Nicola; Renato Iori; Jean-Hugues Renault; Patrick Rollin; Jean-Marc Nuzillard
Source:
Journal of natural products 2018 v.81 no.2 pp. 323-334
ISSN:
1520-6025
Subject:
Brassicales; carbon; computer software; databases; glucosinolates; hydrophilicity; hydrophobicity; models; moieties; nuclear magnetic resonance spectroscopy; secondary metabolites; spectral analysis; stable isotopes
Abstract:
... Glucosinolates (GLs) constitute a class of plant secondary metabolites that are characteristic of the order Brassicales. They each contain a common hydrophilic moiety connected to a mostly hydrophobic side chain whose constitution is the most frequent structural variant. Their transformations by myrosinases lead to intensively studied and highly reactive compounds of biological relevancy. In other ...
DOI:
10.1021/acs.jnatprod.7b00776

16. Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana

Author:
Joanne Soon-Yee Yeap; Suerialoasan Navanesan; Kae-Shin Sim; Kien-Thai Yong; Subramaniam Gurusamy; Siew-Huah Lim; Yun-Yee Low; Toh-Seok Kam
Source:
Journal of natural products 2018 v.81 no.5 pp. 1266-1277
ISSN:
1520-6025
Subject:
Alstonia; X-ray diffraction; alkaloids; cytotoxicity; ethanol; human cell lines; humans; inhibitory concentration 50; neoplasm cells; spectral analysis
Abstract:
... Examination of the EtOH extract of the Malayan Alstonia penangiana resulted in the isolation of 10 new alkaloids, comprising two ajmaline (1, 2), four macroline oxindole (3–6), and four macroline–akuammiline bisindole alkaloids (7–10). The structures of these alkaloids were determined based on analysis of the spectroscopic data and, in the case of the oxindole 6 and the bisindole alkaloid 7, also ...
DOI:
10.1021/acs.jnatprod.8b00170

17. Alkaloids with Immunosuppressive Activity from the Bark of Pausinystalia yohimbe

Author:
Ye Liu; Heng-Yi Yu; Hong-Zhe Xu; Jun-Jun Liu; Xiang-Gao Meng; Ming Zhou; Han-Li Ruan
Source:
Journal of natural products 2018 v.81 no.8 pp. 1841-1849
ISSN:
1520-6025
Subject:
B-lymphocytes; Pausinystalia; T-lymphocytes; X-ray diffraction; alkaloids; bark; immunosuppression; inhibitory concentration 50; lymphocyte proliferation; spectroscopy
Abstract:
... Ten new alkaloids (1–10), including two pairs of enantiomeric mixtures (5a,b and 6a,b), and 15 known analogues (11–25) were obtained from the bark of Pausinystalia yohimbe. The structures of 1–25 were established by spectroscopic methods, and the absolute configurations of compounds 1–10 were resolved by X-ray diffraction and ECD data analyses. The in vitro immunosuppressive activities of selected ...
DOI:
10.1021/acs.jnatprod.8b00324

18. Alveolarides: Antifungal Peptides from Microascus alveolaris Active against Phytopathogenic Fungi

Author:
Serge Fotso; Paul Graupner; Quanbo Xiong; Jeffrey R. Gilbert; Don Hahn; Cruz Avila-Adame; George Davis; Kengo Sumiyoshi
Source:
Journal of natural products 2018 v.81 no.1 pp. 10-15
ISSN:
1520-6025
Subject:
Magnaporthe oryzae; Mycosphaerella graminicola; Phakopsora pachyrhizi; Puccinia recondita; Ustilago zeae; antimicrobial peptides; bioactive properties; culture media; mass spectrometry; nuclear magnetic resonance spectroscopy; phenylalanine; plant pathogenic fungi
Abstract:
... Three novel cyclodepsipeptides, alveolarides A (1), B (2), and C (3), each possessing the rare 2,3-dihydroxy-4-methyltetradecanoic acid unit and a β-phenylalanine amino acid residue, along with the known peptide scopularide were isolated and identified from the culture broth of Microascus alveolaris strain PF1466. The pure compounds were evaluated for biological activity, and alveolaride A (1) pro ...
DOI:
10.1021/acs.jnatprod.7b00337

19. Amarisolide F, an Acylated Diterpenoid Glucoside and Related Terpenoids from Salvia amarissima

Author:
Mabel Fragoso-Serrano; Naytzé Ortiz-Pastrana; Norma Luna-Cruz; Rubén A. Toscano; Angel G. Alpuche-Solís; Alfredo Ortega; Elihú Bautista
Source:
Journal of natural products 2018 v.82 no.3 pp. 631-635
ISSN:
1520-6025
Subject:
Salvia; X-ray diffraction; cell lines; cytotoxicity; diterpenoids; flowers; glucosides; leaves; methanolysis; nuclear magnetic resonance spectroscopy; phenotype; reserpine
Abstract:
... Nine terpenoids were isolated from the leaves and flowers of Salvia amarissima, including a new acylated diterpenoid glucoside, amarisolide F (1), a new neo-clerodane diterpenoid, amarissinin D (2), which was isolated as an acetyl derivative (2a), and four known diterpenoids. The structure of amarisolide F (1) was elucidated by NMR and MS data analyses, as well as its methanolysis products 7 and 8 ...
DOI:
10.1021/acs.jnatprod.8b00565

20. An Alkaloid from Scorpion Venom: Chemical Structure and Synthesis

Author:
Shibdas Banerjee; Elumalai Gnanamani; Stephen R. Lynch; Fernando Zamudio Zuñiga; Juana María Jiménez-Vargas; Lourival Domingos Possani; Richard N. Zare
Source:
Journal of natural products 2018 v.81 no.8 pp. 1899-1904
ISSN:
1520-6025
Subject:
Scorpiones; alkaloids; chemical structure; insecticidal properties; mass spectrometry; medicinal properties; nuclear magnetic resonance spectroscopy; scorpion venoms
Abstract:
... While most scorpion venom components identified in the past are peptidic or proteinic in nature, we report here a new alkaloid isolated from the venom of the Mexican scorpion Megacormus gertschi. Nuclear magnetic resonance and mass spectrometric investigations elucidate the structure of the alkaloid as (Z)-N-(2-(1H-imidazol-4-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)-2-methoxyacrylamide (1). A chemi ...
DOI:
10.1021/acs.jnatprod.8b00527

21. An Anti-Inflammatory PPAR-γ Agonist from the Jellyfish-Derived Fungus Penicillium chrysogenum J08NF-4

Author:
Sen Liu; Mingzhi Su; Shao-Jiang Song; Jongki Hong; Hae Young Chung; Jee H. Jung
Source:
Journal of natural products 2018 v.81 no.2 pp. 356-363
ISSN:
1520-6025
Subject:
Penicillium chrysogenum; agonists; fungi; hepatocytes; in vitro studies; inducible nitric oxide synthase; inflammation; interleukin-1beta; interleukin-6; macrophages; mice; nitric oxide; phosphorylation; protein content; signal transduction; transcription factor NF-kappa B; tumor necrosis factor-alpha
Abstract:
... An investigation of the jellyfish-derived fungus Penicillium chrysogenum J08NF-4 led to the isolation of two new meroterpene derivatives, chrysogenester (1) and 5-farnesyl-2-methyl-1-O-methylhydroquinone (2), and four known farnesyl meroterpenes. Docking analysis of 1 showed that it binds to PPAR-γ in the same manner as the natural PPAR-γ agonist amorfrutin B (7). Compound 1 activated PPAR-γ in mu ...
DOI:
10.1021/acs.jnatprod.7b00846

22. 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

23. Analytical Method To Detect and Quantify Avocatin B in Hass Avocado Seed and Pulp Matter

Author:
Nawaz Ahmed; Richard W. Smith; Juan J. Aristizabal Henao; Ken D. Stark; Paul A. Spagnuolo
Source:
Journal of natural products 2018 v.81 no.4 pp. 818-824
ISSN:
1520-6025
Subject:
antineoplastic activity; avocados; fatty alcohols; fruit pulp; gas chromatography-mass spectrometry; leukemia; liquid chromatography; nuclear magnetic resonance spectroscopy; quality control; seeds; stem cells
Abstract:
... Avocatin B, an avocado-derived compound mixture, was demonstrated recently to possess potent anticancer activity by selectively targeting and eliminating leukemia stem cells. Avocatin B is a mixture of avocadene and avocadyne, two 17-carbon polyhydroxylated fatty alcohols (PFAs), first discovered in avocado seeds; their quantities in avocado pulp are unknown. Analytical methods to detect avocado s ...
DOI:
10.1021/acs.jnatprod.7b00914

24. Ancistrolikokine E₃, a 5,8′-Coupled Naphthylisoquinoline Alkaloid, Eliminates the Tolerance of Cancer Cells to Nutrition Starvation by Inhibition of the Akt/mTOR/Autophagy Signaling Pathway

Author:
Suresh Awale; Dya Fita Dibwe; Chandrasekar Balachandran; Shaimaa Fayez; Doris Feineis; Blaise Kimbadi Lombe; Gerhard Bringmann
Source:
Journal of natural products 2018 v.81 no.10 pp. 2282-2291
ISSN:
1520-6025
Subject:
Ancistrocladus; alkaloids; anaerobic conditions; antineoplastic agents; autophagy; cell movement; cytotoxicity; humans; neoplasm cells; nutrients; oxygen; pancreatic neoplasms; signal transduction; starvation
Abstract:
... PANC-1 human pancreatic cancer cells are characterized by their ability to proliferate aggressively under hypovascular and hypoxic conditions in the tumor microenvironment, displaying a remarkable tolerance to nutrition starvation. The antiausterity strategy is a new approach in anticancer drug discovery aiming at the identification of potent agents that inhibit preferentially the survival of tumo ...
DOI:
10.1021/acs.jnatprod.8b00733

25. Aniline-Tetramic Acids from the Deep-Sea-Derived Fungus Cladosporium sphaerospermum L3P3 Cultured with the HDAC Inhibitor SAHA

Author:
Zhenzhen Zhang; Xueqian He; Guangwei Wu; Congcong Liu; Changjun Lu; Qianqun Gu; Qian Che; Tianjiao Zhu; Guojian Zhang; Dehai Li
Source:
Journal of natural products 2018 v.81 no.7 pp. 1651-1657
ISSN:
1520-6025
Subject:
Cladosporium sphaerospermum; acids; aniline; biotransformation; cell lines; cytotoxicity; enzyme inhibitors; fungi; histone deacetylase; inhibitory concentration 50; moieties; nuclear magnetic resonance spectroscopy; polyketides
Abstract:
... Four new tetramic acids, cladosins H–K (1–4), and a related known compound, cladodionen (5), were isolated from the culture of the Mariana Trench (depth 6562 m) sediment-derived fungus Cladosporium sphaerospermum L3P3 treated with the histone deacetylase inhibitor SAHA (suberanilohydroxamic acid). Interestingly, compounds 1–5 existed as equilibrium E/Z mixtures and 1–4 were the first cases of tetr ...
DOI:
10.1021/acs.jnatprod.8b00289

26. Ansamycins with Antiproliferative and Antineuroinflammatory Activity from Moss-Soil-Derived Streptomyces cacaoi subsp. asoensis H2S5

Author:
Dan Tang; Ling-Li Liu; Qiu-Rui He; Wen Yan; Ding Li; Jin-Ming Gao
Source:
Journal of natural products 2018 v.81 no.9 pp. 1984-1991
ISSN:
1520-6025
Subject:
apoptosis; flow cytometry; human cell lines; inhibitory concentration 50; liquids; mosses and liverworts; nitric oxide; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... Three new 21-membered macrocyclic benzenoid ansamycins, trienomycins J–L (1–3), together with seven known analogues, trienomycins A–G (4–10), were isolated from liquid culture of the moss soil-derived actinomycete Streptomyces cacaoi subsp. asoensis H2S5. The structures of the new compounds were elucidated by extensive NMR spectroscopic analysis and HRESIMS data. The absolute configurations of tri ...
DOI:
10.1021/acs.jnatprod.8b00203

27. Anti-Inflammatory Prenylated Phenylpropenols and Coumarin Derivatives from Murraya exotica

Author:
Bing-Yu Liu; Chen Zhang; Ke-Wu Zeng; Jun Li; Xiao-Yu Guo; Ming-Bo Zhao; Peng-Fei Tu; Yong Jiang
Source:
Journal of natural products 2018 v.81 no.1 pp. 22-33
ISSN:
1520-6025
Subject:
Murraya exotica; X-ray diffraction; alcohols; coumarin; cycloaddition reactions; inhibitory concentration 50; metals; moieties; neuroglia; nitric oxide; roots
Abstract:
... Three new prenylated phenylpropenols, exotiacetals A–C (1–3), 10 new coumarin derivatives, exotimarins A–I (4–13), and 35 known analogues (14–48) were isolated from the roots of Murraya exotica. The absolute configurations of the new compounds were assigned via comparison of their specific rotations, single-crystal X-ray diffraction data, Mosher’s method, the ECD exciton coupling method, compariso ...
DOI:
10.1021/acs.jnatprod.7b00518

28. Anti-Staphylococcal Calopins from Fruiting Bodies of Caloboletus radicans

Author:
Fakir Shahidullah Tareq; Choudhury Mahmood Hasan; M. Mukhlesur Rahman; Mohd Mukrish Mohd Hanafi; Lucio Colombi Ciacchi; Monika Michaelis; Tilmann Harder; Jan Tebben; Md. Tofazzal Islam; Peter Spiteller
Source:
Journal of natural products 2018 v.81 no.2 pp. 400-404
ISSN:
1520-6025
Subject:
Enterococcus faecalis; antibiotic resistance; cell lines; fish; fruiting bodies; methicillin; methicillin-resistant Staphylococcus aureus; minimum inhibitory concentration; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; pathogens; stereochemistry
Abstract:
... Three new and seven known calopins were isolated from Caloboletus radicans. The structures of the new cyclocalopins, 8-deacetylcyclocalopin B (1), cyclocalopin A-15-ol (2), and 12,15-dimethoxycyclocalopin A (3), were mainly elucidated by NMR and MS data analysis. The stereochemistry of 1–3 was assigned based on NOE correlations and coupling constants and by comparison of their CD spectra with thos ...
DOI:
10.1021/acs.jnatprod.7b00525

29. Anti-inflammatory Grayanane Diterpenoids from the Leaves of Rhododendron molle

Author:
Junfei Zhou; Tingting Liu; Hanqi Zhang; Guijuan Zheng; Yue Qiu; Mengyi Deng; Chun Zhang; Guangmin Yao
Source:
Journal of natural products 2018 v.81 no.1 pp. 151-161
ISSN:
1520-6025
Subject:
Rhododendron; X-ray diffraction; anti-inflammatory activity; diterpenoids; inhibitory concentration 50; leaves; macrophages; mice; nitric oxide; spectral analysis; structure-activity relationships
Abstract:
... Thirteen new grayanane diterpenoids (1–13), a new dimeric grayanane diterpenoid, bimollfoliagein A (14), and 15 known analogues (15–29) were isolated from the leaves of Rhododendron molle. The structures of the new compounds (1–14) were determined by extensive spectroscopic data interpretation. The absolute configurations of 1–3, 7, 8, 16, 18, and 24 were defined by single-crystal X-ray diffractio ...
DOI:
10.1021/acs.jnatprod.7b00799

30. Anti-inflammatory Potential of Flavonoids from the Aerial Parts of Corispermum marschallii

Author:
Karolina Pawłowska; Monika E. Czerwińska; Marcin Wilczek; Jakub Strawa; Michał Tomczyk; Sebastian Granica
Source:
Journal of natural products 2018 v.81 no.8 pp. 1760-1768
ISSN:
1520-6025
Subject:
aerial parts; anti-inflammatory activity; derivatization; flavonoids; glycosides; interleukin-8; moieties; neutrophils; nuclear magnetic resonance spectroscopy; phenolic compounds; tumor necrosis factor-alpha
Abstract:
... The isolation of phenolics from aerial parts of Corispermum marschallii yielded a total of 13 compounds including nine previously undescribed patuletin and spinacetin glycosides. These were identified as patuletin 3-O-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (1), spinacetin 3-O-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (2), patuletin 3-O-(6″-O-β-d-glucopyranosyl)-β-d-galactopyranoside (3), ...
DOI:
10.1021/acs.jnatprod.8b00152

31. Antiangiogenic Activity and Chemical Derivatization of the Neurotoxic Acetogenin Annonacin Isolated from Asimina triloba

Author:
Paige J. Monsen; Frederick A. Luzzio
Source:
Journal of natural products 2018 v.81 no.8 pp. 1905-1909
ISSN:
1520-6025
Subject:
Asimina triloba; North Americans; azides; bioassays; derivatization; inhibitory concentration 50; iodination; membrane permeability; neurotoxicity; rats
Abstract:
... Annonacin (1) was isolated from the North American pawpaw (Asimina triloba), as reported earlier from these laboratories. Natural 1 was submitted to the rat aortic ring bioassay for evaluation of antiangiogenic activity and was found to inhibit microvessel growth (IC₅₀ value of 3 μM). 4,10,15,20-Tetraazido derivatives of 1 were prepared by permesylation followed by azide displacement or by iodinat ...
DOI:
10.1021/acs.jnatprod.8b00284

32. Antibacterial Cyclic Lipopeptide Enamidonins with an Enamide-Linked Acyl Chain from a Streptomyces Species

Author:
Sangkeun Son; Sung-Kyun Ko; Seung Min Kim; Eun Kim; Gil Soo Kim; Byeongsan Lee; In-Ja Ryoo; Won-Gon Kim; Jung-Sook Lee; Young-Soo Hong; Jae-Hyuk Jang; Jong Seog Ahn
Source:
Journal of natural products 2018 v.81 no.11 pp. 2462-2469
ISSN:
1520-6025
Subject:
Gram-positive bacteria; Staphylococcus aureus; Streptomyces; acetone; amino acids; antibacterial properties; antibiotic resistance; derivatization; linkage groups; lipopeptides; liquid chromatography; mass spectrometry; methicillin; nuclear magnetic resonance spectroscopy; Korean Peninsula
Abstract:
... Three cyclic lipopeptides, including one known (1) and two new (2 and 3) compounds, that possess the rare enamide linkage group were discovered from Streptomyces sp. KCB14A132, an actinobacterium isolated from a soil sample collected from Jeung Island, Korea. The NMR and MS-based characterization showed that they differed in the amino acid residues in the peptide backbone. Application of Marfey’s ...
DOI:
10.1021/acs.jnatprod.8b00497

33. Antibacterial Dimeric Acylphloroglucinols from Hypericum japonicum

Author:
Yan-Ping Li; Kun Hu; Xing-Wei Yang; Gang Xu
Source:
Journal of natural products 2018 v.81 no.4 pp. 1098-1102
ISSN:
1520-6025
Subject:
Hypericum; X-ray diffraction; antibacterial properties; carboxylic ester hydrolases; enzyme inhibition; inhibitory concentration 50; minimum inhibitory concentration; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... Nine dimeric acylphloroglucinols, including the new hyperjaponicols A–D (1–4), were isolated from the whole plant of Hypericum japonicum. The new structures were determined by the interpretation of NMR and MS data, and the relative configuration of the known compound, sarothralen C (5), was reassigned via NMR spectroscopic analysis and single-crystal X-ray diffraction data. The inhibitory activiti ...
DOI:
10.1021/acs.jnatprod.8b00017

34. Antibacterial Prenylated Isoflavonoids from the Stems of Millettia extensa

Author:
Achara Raksat; Wisanu Maneerat; Raymond J. Andersen; Stephen G. Pyne; Surat Laphookhieo
Source:
Journal of natural products 2018 v.81 no.8 pp. 1835-1840
ISSN:
1520-6025
Subject:
Millettia; antibacterial properties; isoflavones; minimum inhibitory concentration; spectral analysis; stems
Abstract:
... The first phytochemical investigation of the stem extract of Millettia extensa resulted in the isolation and identification of six new isoflavones, millexatins A–F (1–6), together with 16 known compounds. The structures of these new compounds were determined on the basis of their spectroscopic data. Millexatin A (1) is a rare isoflavone containing three isoprenyl units on a modified A ring. Compou ...
DOI:
10.1021/acs.jnatprod.8b00321

35. Antileishmanial Carbasugars from Geosmithia langdonii

Author:
Lourin G. Malak; Mohamed Ali Ibrahim; Ahmed M. Moharram; Pankaj Pandey; Babu Tekwani; Robert J. Doerksen; Daneel Ferreira; Samir A. Ross
Source:
Journal of natural products 2018 v.81 no.10 pp. 2222-2227
ISSN:
1520-6025
Subject:
Geosmithia; Leishmania donovani; antileishmanial properties; carbasugars; circular dichroism spectroscopy; cotton fabric; fungi; inhibitory concentration 50; metabolites; models; nuclear magnetic resonance spectroscopy; Egypt
Abstract:
... Two new carbasugar-type metabolites, (1S,2R,3R,4R,5R)-2,3,4-trihydroxy-5-methylcyclohexyl-2′,5′-dihydroxybenzoate (1) and (1S,2S,3S,4R,5R)-4-[(2′,5′-dihydroxybenzyl)oxy]-5-methylcyclohexane-1,2,3-triol (2), were isolated from the filamentous fungus Geosmithia langdonii isolated from cotton textiles from Assiut, Egypt. The structures of 1 and 2 were elucidated based on comprehensive 1D and 2D NMR a ...
DOI:
10.1021/acs.jnatprod.8b00473

36. Antineoplastic Agents. 606. The Betulastatins

Author:
George R. Pettit; Noeleen Melody; Jean-Charles Chapuis
Source:
Journal of natural products 2018 v.81 no.3 pp. 458-464
ISSN:
1520-6025
Subject:
antineoplastic agents; betulin; cell growth; cell lines; chimerism; growth inhibitors; growth retardation; mechanism of action; neoplasm cells; neoplasms
Abstract:
... The medicinal potential of the plant pentacyclic triterpene betulin has generated long-term interest focused on various SAR research avenues. The present approach was based on producing further analogues (chimeras) arising from a studied modification of betulin bonded to the Dov-Val-Dil-Dap unit of the powerful anticancer drug dolastatin 10, which provided betulastatins 1 (7b), 2 (11b), 3 (16b), a ...
DOI:
10.1021/acs.jnatprod.7b00536

37. Antinociceptive Diterpenoids from the Leaves and Twigs of Rhododendron decorum

Author:
Yu-Xun Zhu; Zhao-Xin Zhang; Hui-Min Yan; Di Lu; Huan-Ping Zhang; Li Li; Yun-Bao Liu; Yong Li
Source:
Journal of natural products 2018 v.81 no.5 pp. 1183-1192
ISSN:
1520-6025
Subject:
Rhododendron; X-ray diffraction; analgesic effect; branches; chemical structure; diterpenoids; ethanol; leaves; nuclear magnetic resonance spectroscopy; writhing test
Abstract:
... Three new leucothane-type (1–3), two new micrathane-type (4, 5), eight new grayanane-type diterpenoids (6–13), and four known compounds were obtained from the ethanol extract of the leaves and twigs of Rhododendron decorum. The structures were determined based on NMR spectra, quantum chemical calculations, and X-ray crystallography. The antinociceptive activities of compounds 1, 3, 4, 6, 8, 10–13, ...
DOI:
10.1021/acs.jnatprod.7b00941

38. Antinociceptive Potential of Zinnia grandiflora

Author:
Valeria Reyes-Pérez; Araceli Pérez Vásquez; Myrna Déciga-Campos; Robert Bye; Edelmira Linares; Rachel Mata
Source:
Journal of natural products 2018 v.82 no.3 pp. 456-461
ISSN:
1520-6025
Subject:
X-ray diffraction; Zinnia; acute toxicity; aerial parts; analgesic effect; anti-inflammatory activity; diclofenac; edema; ethyl acetate; formalin test; fractionation; lethal dose 50; methylene chloride; mice; models; spectral analysis
Abstract:
... An aqueous extract prepared from the aerial parts of Zinnia grandiflora was found not to induce acute toxicity (LD₅₀> 5g/kg, p.o.) in mice when tested by the Lorke method. This extract showed notable antinociceptive and anti-inflammatory actions when evaluated by the formalin- (ED₅₀ = 224.62 ± 38.17 mg/kg, p.o.) and the carrageenan-induced paw edema models in mice, respectively. The organic-solubl ...
DOI:
10.1021/acs.jnatprod.8b00758

39. Antiplasmodial β-Triketone–Flavanone Hybrids from the Flowers of the Australian Tree Corymbia torelliana

Author:
Sarath P. D. Senadeera; Leonardo Lucantoni; Sandra Duffy; Vicky M. Avery; Anthony R. Carroll
Source:
Journal of natural products 2018 v.81 no.7 pp. 1588-1597
ISSN:
1520-6025
Subject:
Corymbia torelliana; Eucalyptus; Plasmodium falciparum; antimalarials; antiplasmodial properties; flowers; inhibitory concentration 50; methanol; nuclear magnetic resonance spectroscopy; trees
Abstract:
... The methanol extract of the flowers of the Australian eucalypt tree Corymbia torelliana yielded six new β-triketone–flavanone hybrids, torellianones A–F (1–6), the tetrahydroxycyclohexane torellianol A (7), and known β-triketones (4S)-ficifolidione (8) and (4R)-ficifolidione (9), and β-triketone–flavanones kunzeanone A (10) and kunzeanone B (11). Torellianones A and B, C and D, and E and F were ea ...
DOI:
10.1021/acs.jnatprod.8b00154

40. Antiproliferative Carvotacetones from Sphaeranthus africanus

Author:
Huyen T. Tran; Eva-Maria Pferschy-Wenzig; Nadine Kretschmer; Olaf Kunert; Loi Huynh; Rudolf Bauer
Source:
Journal of natural products 2018 v.81 no.8 pp. 1829-1834
ISSN:
1520-6025
Subject:
Sphaeranthus; aerial parts; cytotoxicity; fractionation; human cell lines; humans; inhibitory concentration 50; kidney cells; mass spectrometry; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; Vietnam
Abstract:
... Five carvotacetone derivatives, including two known ones, 3,5-diangeloyloxy-7-hydroxycarvotacetone (1) and 3-angeloyloxy-5-[2″,3″-epoxy-2″-methylbutanoyloxy]-7-hydroxycarvotacetone (2), along with three new compounds, 3-angeloyloxy-5-[3″-chloro-2″-hydroxy-2″-methylbutanoyloxy]-7-hydroxycarvotacetone (3), 5-angeloyloxy-7-hydroxy-3-tigloyloxycarvotacetone (4), and 3-angeloyloxy-5,7-dihydroxycarvotac ...
DOI:
10.1021/acs.jnatprod.8b00309

41. Antiproliferative Sesquiterpenoids from Ligularia rumicifolia with Diverse Skeletons

Author:
Ye Ye; Drolma Dawa; Guang-Hui Liu; Min Zhao; Dorje Tseden; Yu-Cheng Gu; Li-Sheng Ding; Zhi-Xing Cao; Yan Zhou
Source:
Journal of natural products 2018 v.81 no.9 pp. 1992-2003
ISSN:
1520-6025
Subject:
Ligularia; X-ray diffraction; chemical structure; human cell lines; humans; inhibitory concentration 50; neoplasm cells; sesquiterpenoids; spectral analysis
Abstract:
... Twenty-two new sesquiterpenoids with four skeletal types and 15 known analogues were isolated from the whole plants of Ligularia rumicifolia. The structures of the isolates were elucidated based on comprehensive spectroscopic data analysis. Compound 1 is a C₁₄ nor-sesquiterpenoid featuring a 6/6/6 tricyclic skeleton with a 9,13-ether bridge. The absolute configuration of 2 was established through ...
DOI:
10.1021/acs.jnatprod.8b00197

42. Antiprotozoal Isoprenoids from Salvia hydrangea

Author:
Marzieh Tabefam; Mahdi Moridi Farimani; Ombeline Danton; Justine Ramseyer; Samad Nejad Ebrahimi; Markus Neuburger; Marcel Kaiser; Peyman Salehi; Olivier Potterat; Matthias Hamburger
Source:
Journal of natural products 2018 v.81 no.12 pp. 2682-2691
ISSN:
1520-6025
Subject:
Leishmania donovani; Plasmodium falciparum; Salvia hydrangea; Trypanosoma cruzi; Trypanosoma rhodesiense; X-ray diffraction; antiprotozoal properties; biochemical pathways; circular dichroism spectroscopy; copper; cytotoxicity; fractionation; hexane; inhibitory concentration 50; isoprenoids; mass spectrometry; myoblasts; nuclear magnetic resonance spectroscopy; rats
Abstract:
... Fractionation of the n-hexane extract of Salvia hydrangea afforded seven isoprenoids including six new compounds (1–6) and salvadione A (7). Their structures were established by comprehensive spectroscopic and spectrometric data analysis (1D and 2D NMR, HRMS). The absolute configuration of salvadione A (7) was established by single-crystal X-ray diffraction analysis with Cu/Kα radiation. In additi ...
DOI:
10.1021/acs.jnatprod.8b00498

43. Antiprotozoal Sesquiterpene Lactones and Other Constituents from Tarchonanthus camphoratus and Schkuhria pinnata

Author:
Njogu M. Kimani; Josphat C. Matasyoh; Marcel Kaiser; Reto Brun; Thomas J. Schmidt
Source:
Journal of natural products 2018 v.81 no.1 pp. 124-130
ISSN:
1520-6025
Subject:
Tarchonanthus camphoratus; Trypanosoma rhodesiense; active ingredients; aerial parts; antiprotozoal agents; antitrypanosomal properties; cell lines; chromatography; cytotoxicity; flavonoids; inhibitory concentration 50; mammals; methylene chloride; nuclear magnetic resonance spectroscopy; sesquiterpenoid lactones; trypomastigotes
Abstract:
... In continuation of a search for new antiprotozoal agents from plants of the family Asteraceae, Tarchonanthus camphoratus and Schkuhria pinnata have been investigated. By following the promising in vitro activity of the dichloromethane extracts from their aerial parts, bioassay-guided chromatographic isolation yielded two known sesquiterpene lactones (1 and 2) from T. camphoratus and 20 known compo ...
DOI:
10.1021/acs.jnatprod.7b00747

44. Antitumor Activity of Diterpenoids from Jatropha gossypiifolia: Cell Cycle Arrest and Apoptosis-Inducing Activity in RKO Colon Cancer Cells

Author:
Chun-Yan Zhang; Li-Jun Zhang; Zhi-Cheng Lu; Chen-Yun Ma; Ying Ye; Khalid Rahman; Hong Zhang; Jian-Yong Zhu
Source:
Journal of natural products 2018 v.81 no.8 pp. 1701-1710
ISSN:
1520-6025
Subject:
Jatropha gossypiifolia; X-ray diffraction; antineoplastic activity; apoptosis; branches; cell cycle checkpoints; circular dichroism spectroscopy; colorectal neoplasms; cytotoxicity; diterpenoids; dose response; flow cytometry; inhibitory concentration 50; leaves; neoplasm cells
Abstract:
... Nine new minor diterpenoids, jatrogossones A–I (1–9), and six known analogues (10–15) were separated from an extract of the branches and leaves of Jatropha gosspiifolia. Compounds 4–6 and 10, possessing a 5/11 fused-ring skeleton, and 8, 9, and 13, with a 5/9/5 fused-ring skeleton, represent rare diterpenoid skeletons that have been found only in compounds isolated from plants of the Jatropha genu ...
DOI:
10.1021/acs.jnatprod.7b01036

45. Applying Molecular Networking for the Detection of Natural Sources and Analogues of the Selective Gq Protein Inhibitor FR900359

Author:
Raphael Reher; Markus Kuschak; Nina Heycke; Suvi Annala; Stefan Kehraus; Hao-Fu Dai; Christa E. Müller; Evi Kostenis; Gabriele M. König; Max Crüsemann
Source:
Journal of natural products 2018 v.81 no.7 pp. 1628-1635
ISSN:
1520-6025
Subject:
Ardisia; G-protein coupled receptors; Oriental traditional medicine; bioactive properties; inhibitory concentration 50; leaves; medicinal plants; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... The cyclic depsipeptide FR900359 (FR), isolated from the traditional Chinese medicine plant Ardisia crenata, is a potent Gq protein inhibitor and thus a valuable tool to study Gq-mediated signaling of G protein-coupled receptors. Two new FR analogues (3 and 4) were isolated from A. crenata together with the known analogues 1 and 2. The structures of compounds 3 and 4 were established by NMR spectr ...
DOI:
10.1021/acs.jnatprod.8b00222

46. Arbutin Derivatives Isolated from Ancient Proteaceae: Potential Phytochemical Markers Present in Bellendena, Cenarrhenes, and Persoonia Genera

Author:
Bianca J. Deans; Nathan L. Kilah; Gregory J. Jordan; Alex C. Bissember; Jason A. Smith
Source:
Journal of natural products 2018 v.81 no.5 pp. 1241-1251
ISSN:
1520-6025
Subject:
Persoonia; chemical constituents of plants; esters; glycosides
Abstract:
... Extensive phytochemical studies of the paleoendemic Tasmanian Proteaceae species Bellendena montana, Cenarrhenes nitida, and Persoonia gunnii were conducted employing pressurized hot water extraction. As part of these studies, six novel glycosides were isolated, including rare examples of glycoside-containing natural products featuring tiglic acid esters. These polar molecules may represent potent ...
DOI:
10.1021/acs.jnatprod.7b01038

47. Aturanosides A and B, Glycosylated Anthraquinones with Antiangiogenic Activity from a Soil-Derived Streptomyces Species

Author:
Jun-Pil Jang; Gwi Ja Hwang; Mina Jang; Shunji Takahashi; Sung-Kyun Ko; Hiroyuki Osada; Jae-Hyuk Jang; Jong Seog Ahn
Source:
Journal of natural products 2018 v.81 no.9 pp. 2004-2009
ISSN:
1520-6025
Subject:
Streptomyces; anthraquinones; cadherins; cytotoxicity; derivatization; glycosylation; human umbilical vein endothelial cells; nuclear magnetic resonance spectroscopy; phosphorylation; protein content; spectral analysis; sugars; vascular endothelial growth factor receptors; vascular endothelial growth factors
Abstract:
... A chemical investigation of a culture extract from a soil-derived Streptomyces sp. RK88-1441 led to the isolation and characterization of two new glycosylated anthraquinones, aturanosides A (1) and B (2), and a new anthraquinone derivative, aturanocin (3). The structures of these compounds were elucidated by detailed NMR and MS spectroscopic analyses. The absolute configurations of the sugar units ...
DOI:
10.1021/acs.jnatprod.8b00307

48. Auranthine, a Benzodiazepinone from Penicillium aurantiogriseum: Refined Structure, Absolute Configuration, and Cytotoxicity

Author:
Svetlana A. Kalinina; Dmitrii V. Kalinin; Yannick Hövelmann; Constantin G. Daniliuc; Christian Mück-Lichtenfeld; Benedikt Cramer; Hans-Ulrich Humpf
Source:
Journal of natural products 2018 v.81 no.10 pp. 2177-2186
ISSN:
1520-6025
Subject:
Penicillium aurantiogriseum; X-radiation; circular dichroism spectroscopy; cytotoxicity; moieties; secondary metabolites
Abstract:
... The structure of the known Penicillium aurantiogriseum-derived secondary metabolite auranthine was refined using a combination of synthetic, spectroscopic, and X-ray diffractometric approaches. Thus, auranthine was shown to be a fused quinazolino benzodiazepinedione (2) bearing an acyclic aliphatic nitrile moiety, thereby significantly differing from the originally proposed structure 1 published i ...
DOI:
10.1021/acs.jnatprod.8b00187

49. Azaphilone Derivatives from the Fungus Coniella fragariae Inhibit NF-κB Activation and Reduce Tumor Cell Migration

Author:
Haiqian Yu; Julia Sperlich; Attila Mándi; Tibor Kurtán; Haofu Dai; Nicole Teusch; Zhi-Yong Guo; Kun Zou; Zhen Liu; Peter Proksch
Source:
Journal of natural products 2018 v.81 no.11 pp. 2493-2500
ISSN:
1520-6025
Subject:
Coniella; breast neoplasms; cell lines; cell movement; cytotoxicity; feces; fungi; geese; inhibitory concentration 50; neoplasm cells; nuclear magnetic resonance spectroscopy; transcription factor NF-kappa B
Abstract:
... Seven new azaphilones, coniellins A–G (1–7), were obtained from the fungus Coniella fragariae that had been isolated from goose dung. Their structures were elucidated by analysis of 1D and 2D NMR as well as HRESIMS data. TDDFT-ECD calculation was used to determine the absolute configuration of 1, while Mosher’s method was applied to determine the absolute configuration of 5. While displaying only ...
DOI:
10.1021/acs.jnatprod.8b00540

50. BACE1 Inhibitory Meroterpenoids from Aspergillus terreus

Author:
Changxing Qi; Mengting Liu; Qun Zhou; Weixi Gao; Chunmei Chen; Yongji Lai; Zhengxi Hu; Yongbo Xue; Jinwen Zhang; Dongyan Li; Xiao-Nian Li; Qing Zhang; Jianping Wang; Hucheng Zhu; Yonghui Zhang
Source:
Journal of natural products 2018 v.81 no.9 pp. 1937-1945
ISSN:
1520-6025
Subject:
Aspergillus terreus; X-ray diffraction; amyloid; circular dichroism spectroscopy; inhibitory concentration 50
Abstract:
... Sixteen 3,5-dimethylorsellinic acid–based (DMOA-based) meroterpenoids, including 10 new compounds, asperterpenes D–M (1–10), were obtained from Aspergillus terreus. The structures and absolute configurations of the new compounds were confirmed by extensive spectroscopy, single-crystal X-ray diffraction analysis, and experimental electronic circular dichroism (ECD) measurements. Compounds 2, 3, and ...
DOI:
10.1021/acs.jnatprod.7b01050