Three pairs of variecolortide enantiomers from Eurotium sp. with caspase-3 inhibitory activity

Guo-Dong Chen; Yan-Ru Bao; Yuan-Fan Huang; Dan Hu; Xiao-Xia Li; Liang-Dong Guo; Jia Li; Xin-Sheng Yao; Hao Gao

doi:10.1016/j.fitote.2013.11.012

Three pairs of variecolortide enantiomers from Eurotium sp. with caspase-3 inhibitory activity

Fitoterapia. 2014 Jan:92:252-9. doi: 10.1016/j.fitote.2013.11.012. Epub 2013 Dec 7.

Authors

Guo-Dong Chen¹, Yan-Ru Bao², Yuan-Fan Huang², Dan Hu², Xiao-Xia Li², Liang-Dong Guo³, Jia Li⁴, Xin-Sheng Yao⁵, Hao Gao⁶

Affiliations

¹ Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China; Department of Pharmaceutical Engineering, South China Agricultural University, Guangzhou 510642, PR China.
² Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
³ State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
⁴ National Center for Drug Screening, and State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai 201203, PR China.
⁵ Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China. Electronic address: tyaoxs@jnu.edu.cn.
⁶ Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China. Electronic address: tghao@jnu.edu.cn.

PMID: 24321580
DOI: 10.1016/j.fitote.2013.11.012

Abstract

7-O-methylvariecolortide A (1), variecolortide B (2), and variecolortide C (3), the rare variecolortides existing in racemic manner, were isolated from an endolichenic fungal strain Eurotium sp. (No. 17-11-8-1). With the chiral HPLC technology, (-)-(S)-7-O-methylvariecolortide A (1a), (+)-(R)-7-O-methylvariecolortide A (1b), (-)-(S)-variecolortide B (2a), (+)-(R)-variecolortide B (2b), (-)-(S)-variecolortide C (3a), and (+)-(R)-variecolortide C (3b) were successfully separated and obtained. Their absolute configurations were firstly assigned by ECD experiment and ECD calculation. According to the relation of isolated compounds, a plausible biosynthetic pathway for variecolortides was proposed. In caspase-3 enzymatic assay, compounds 1-3 showed inhibitory activity, with IC50 values of 1.7, 0.8 and 15.7 μM, respectively.

Keywords: Caspase-3 inhibitor; Eurotium sp.; Variecolortides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthracenes / chemistry
Anthracenes / isolation & purification
Anthracenes / pharmacology*
Biological Products / chemistry
Biological Products / pharmacology*
Caspase 3 / metabolism*
Chromatography, High Pressure Liquid
Diketopiperazines / chemistry
Diketopiperazines / isolation & purification
Diketopiperazines / pharmacology
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology*
Eurotium / chemistry*
Indole Alkaloids / chemistry
Indole Alkaloids / isolation & purification
Indole Alkaloids / pharmacology
Inhibitory Concentration 50
Molecular Structure
Piperazines / chemistry
Piperazines / isolation & purification
Piperazines / pharmacology*
Stereoisomerism

Substances

7-O-methylvariecolortide A
Anthracenes
Biological Products
Diketopiperazines
Enzyme Inhibitors
Indole Alkaloids
Piperazines
variecolortide B
variecolortide C
Caspase 3