来自一株藻生赤霉菌的一种新的吡咯烷衍生物和甾体化合物。

A new pyrrolidine derivative and steroids from an algicolous Gibberella zeae strain.

作者信息

Liu Xiang-Hong, Tang Xiao-Zhen, Miao Feng-Ping, Ji Nai-Yun

机构信息

College of Food Science and Engineering, Shandong Agricultural University, Taian 271018, China.

出版信息

Nat Prod Commun. 2011 Sep;6(9):1243-6.

PMID:21941888

Abstract

A new pyrrolidine derivative, 3-hydroxy-5-(hydroxymethyl)-4-(4'-hydroxyphenoxy)pyrrolidin-2-one (1), and eight known steroids, (22E,24R)-7beta,8beta-epoxy-3beta,5alpha,9alpha-trihydroxyergosta-22-en-6-one (2, a reassigned structure of (22E,24R)-5alpha,6alpha-epoxy-3beta,8beta,14alpha-trihydroxyergosta-22-en-7-one), (22E,24R)-3beta,5alpha,9alpha-trihydroxyergosta-7,22-dien-6-one (3), (22E,24R)-3beta,5alpha-dihydroxyergosta-7,22-dien-6-one (4), (22E,24R)-ergosta-7,22-dien-3beta/,5alpha,6beta-triol (5), (22E,24R)-ergosta-5,22-dien-3beta-ol (6), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol (7), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,9(11),22-trien-3beta-ol (8), and (22E,24R)-1(10 --> 6)-abeo-ergosta-5,7,9,22-tetraen-3alpha-ol (9), were isolated from the cultures of Gibberella zeae, an endophytic fungus isolated from the marine green alga Codium fragile. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. Compound 1 showed cytotoxicity against A-549 and BEL-7402 cell lines.

摘要

从分离自海洋绿藻脆弱刚毛藻的内生真菌玉米赤霉中培养物中分离得到一种新的吡咯烷衍生物3-羟基-5-(羟甲基)-4-(4'-羟基苯氧基)吡咯烷-2-酮(1)和8种已知甾体，分别为(22E,24R)-7β,8β-环氧-3β,5α,9α-三羟基麦角甾-22-烯-6-酮(2，(22E,24R)-5α,6α-环氧-3β,8β,14α-三羟基麦角甾-22-烯-7-酮的重新归属结构)、(22E,24R)-3β,5α,9α-三羟基麦角甾-7,22-二烯-6-酮(3)、(22E,24R)-3β,5α-二羟基麦角甾-7,22-二烯-6-酮(4)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(5)、(22E,24R)-麦角甾-5,22-二烯-3β-醇(6)、(22E,24R)-5α,8α-环氧麦角甾-6,22-二烯-3β-醇(7)、(22E,24R)-5α,8α-环氧麦角甾-6,9(11),22-三烯-3β-醇(8)和(22E,24R)-1(10→6)-去甲-麦角甾-5,7,9,22-四烯-3α-醇(9)。通过一维、二维核磁共振和质谱技术阐明了它们的结构和相对立体化学。化合物1对A-549和BEL-7402细胞系显示出细胞毒性。