Thiodiketopiperazines Produced by the Endophytic Fungus Epicoccum nigrum

Thirteen new thiodiketopiperazines, epicoccin I (1), ent-epicoccin G (2), and epicoccins J−T (3−13), together with six known diketopiperazines (14−19), have been isolated from the endophytic fungus Epicoccum nigrum. The structures of 1, 2, and 10 were confirmed by X-ray crystallography, and the abso...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2010-07, Vol.73 (7), p.1240-1249
Main Authors: Wang, Jia-Ming, Ding, Guang-Zhi, Fang, Lei, Dai, Jun-Gui, Yu, Shi-Shan, Wang, Ying-Hong, Chen, Xiao-Guang, Ma, Shuang-Gang, Qu, Jing, Xu, Song, Du, Dan
Format: Article
Language:English
Subjects:
Animals
Ascomycota - chemistry
Biological and medical sciences
China
Crystallography, X-Ray
Diketopiperazines - chemistry
Diketopiperazines - isolation & purification
Diketopiperazines - pharmacology
Drug Screening Assays, Antitumor
Fabaceae - microbiology
General pharmacology
Glucuronidase - antagonists & inhibitors
Humans
Inhibitory Concentration 50
Medical sciences
Molecular Conformation
Molecular Structure
Neutrophils - drug effects
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Leaves - microbiology
Rats
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Summary:Thirteen new thiodiketopiperazines, epicoccin I (1), ent-epicoccin G (2), and epicoccins J−T (3−13), together with six known diketopiperazines (14−19), have been isolated from the endophytic fungus Epicoccum nigrum. The structures of 1, 2, and 10 were confirmed by X-ray crystallography, and the absolute configurations of 2, 4, 6, and 8 were assigned using Moshers’ method. Compounds 2, 6, 12, and 17 showed potent activities in vitro against the release of β-glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor, with IC50 values of 3.07, 4.16, 4.95, and 1.98 μM, respectively. None of the 19 compounds exhibited detectable cytotoxic activities toward six tumor cell lines (A549, Be-l7402, BGC-823, HCT-8, HCT-116, and A2780) in the MTT assay.
ISSN:0163-3864
1520-6025
DOI:10.1021/np1000895