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 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 beta-glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor, with IC(50) values of 3.07, 4.16, 4.95, and 1.98 microM, 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.
Wang
Jia-Ming
JM
Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, No. 1 Xian Nong Tan Street, Beijing People's Republic of China.
Ding
Guang-Zhi
GZ
Fang
Lei
L
Dai
Jun-Gui
JG
Yu
Shi-Shan
SS
Wang
Ying-Hong
YH
Chen
Xiao-Guang
XG
Ma
Shuang-Gang
SG
Qu
Jing
J
Xu
Song
S
Du
Dan
D
D000818:Animals; D001203:Ascomycota / Q000737:chemistry*; D002681:China; D018360:Crystallography, X-Ray; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D007887:Fabaceae / Q000382:microbiology*; D005966:Glucuronidase / Q000037:antagonists & inhibitors*; D006801:Humans; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000382:microbiology; D051381:Rats
D054659:Diketopiperazines; D005966:Glucuronidase