title: Three pairs of variecolortide enantiomers from Eurotium sp. with caspase-3 inhibitory activity.
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.
authors: 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.
authors: Guo-Dong
authors: GD
authors: Chen
authors: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors: Yan-Ru
authors: YR
authors: Bao
authors: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors: Yuan-Fan
authors: YF
authors: Huang
authors: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors: Dan
authors: D
authors: Hu
authors: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
authors: Xiao-Xia
authors: XX
authors: Li
authors: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
authors: Liang-Dong
authors: LD
authors: Guo
authors: National Center for Drug Screening, and State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai 201203, PR China.
authors: Jia
authors: J
authors: Li
authors: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China. Electronic address: tyaoxs@jnu.edu.cn.
authors: Xin-Sheng
authors: XS
authors: Yao
authors: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China. Electronic address: tghao@jnu.edu.cn.
authors: Hao
authors: H
authors: Gao
mesh_terms: D000873:Anthracenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology*; D053148:Caspase 3 / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D055325:Eurotium / Q000737:chemistry*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: C554759:7-O-methylvariecolortide A; D000873:Anthracenes; D001688:Biological Products; D054659:Diketopiperazines; D004791:Enzyme Inhibitors; D026121:Indole Alkaloids; D010879:Piperazines; C000591474:variecolortide B; C000591475:variecolortide C; D053148:Caspase 3
keywords: Caspase-3 inhibitor; Eurotium sp.; Variecolortides