具对环氧化酶-2抑制活性的椭叶南蛇藤种子的成分

Constituents of the seeds of Hernandia ovigera with inhibitory activity against cyclooxygenase-2.

作者信息

Jang Dae Sik, Cuendet Muriel, Su Bao-Ning, Totura Steven, Riswan Soedarsono, Fong Harry H, Pezzuto John M, Kinghorn A Douglas

机构信息

Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, IL, USA.

出版信息

Planta Med. 2004 Oct;70(10):893-6. doi: 10.1055/s-2004-832612.

DOI:10.1055/s-2004-832612

PMID:15490314

Abstract

A new dibenzylbutyrolactone lignan, (2 R,3 R)-5'-methoxyguayarol (1), was isolated from an EtOAc-soluble extract of the seeds of Hernandia ovigera using an in vitro activity-guided fractionation procedure based on the inhibition of cyclooxygenase-2. Also obtained were three known fatty acid derivatives, (S)-coriolic acid, (+/-)-12,13-epoxyoleic acid, and (+/-)-glycerol 1-monolinolate, and seven known lignans, epiashantin, dehydrodesoxypodophyllotoxin, dehydropodophyllotoxin, (-)-hernolactone, (-)-pinoresinol, (-)-syringaresinol, and (-)-yatein. The structure, including absolute stereochemistry, of compound 1 was determined using spectroscopic methods. All isolates were tested for their inhibitory effects against both cyclooxygenases-1 and -2, with (S)-coriolic acid and (+/-)-glycerol 1-monolinolate shown to have selective inhibitory activity with cyclooxygenase-2.

摘要

采用基于环氧合酶-2抑制作用的体外活性导向分级分离法，从卵形莲叶桐种子的乙酸乙酯可溶提取物中分离出一种新的二苄基丁内酯木脂素，即(2R,3R)-5'-甲氧基愈创木酚(1)。还获得了三种已知的脂肪酸衍生物，即(S)-科里奥利酸、(±)-12,13-环氧油酸和(±)-甘油1-单亚麻酸酯，以及七种已知的木脂素，表阿散蒂因、脱氢脱氧鬼臼毒素、脱氢鬼臼毒素、(-)-赫诺内酯、(-)-松脂醇、(-)-丁香树脂醇和(-)-叶亭。通过光谱方法确定了化合物1的结构，包括绝对立体化学。对所有分离物进行了对环氧合酶-1和-2的抑制作用测试，结果表明(S)-科里奥利酸和(±)-甘油1-单亚麻酸酯对环氧合酶-2具有选择性抑制活性。