从海南软珊瑚 Sarcophyton trocheliophorum Marenzeller 中发现的作为 PTP1B 抑制剂的新型二萜类化合物。

Unprecedented diterpenoids as a PTP1B inhibitor from the Hainan soft coral Sarcophyton trocheliophorum Marenzeller.

机构信息

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhang Jiang Hi-Tech Park, Shanghai, 201203, PR China.

出版信息

Org Lett. 2013 Jan 18;15(2):274-7. doi: 10.1021/ol303110d. Epub 2012 Dec 28.

DOI:10.1021/ol303110d

PMID:23273218

Abstract

Methyl sarcotroates A and B (3 and 4), two unprecedented diterpenoids possessing a tetradecahydrocyclopenta[3',4']cyclobuta[1',2':4,5]cyclonona[1,2-b]oxirene ring system, along with their probable biogenetic precursor, sarcophytonolide M (1), were isolated from the Hainan soft coral Sarcophyton trocheliophorum. Their structures were elucidated by detailed spectroscopic analysis, and the absolute configuration of compound 3 was determined by TDDFT ECD calculations. Compound 4 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), being similar to that of positive control oleanolic acid.

摘要

甲基珊瑚醇 A 和 B（3 和 4），两个具有十四氢环戊[a3',4']环丁[a1',2':4,5]环壬[a1,2-b]环氧系统的前所未有的二萜类化合物，以及它们可能的生物合成前体，珊瑚醇 M（1），从海南软珊瑚 Sarcophyton trocheliophorum 中分离得到。通过详细的光谱分析阐明了它们的结构，并且通过 TDDFT ECD 计算确定了化合物 3 的绝对构型。化合物 4 对蛋白酪氨酸磷酸酶 1B（PTP1B）表现出显著的抑制活性，与阳性对照齐墩果酸相似。