来源于海洋真菌紫色被孢霉的烯基化吲哚二酮哌嗪生物碱作为磷酸酶抑制剂。

Prenylated indole diketopiperazine alkaloids as phosphatase inhibitors from the marine-derived fungus Talaromyces purpureogenus.

机构信息

CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, China.

New Drug Research & Development Center of North China Pharmaceutical Group Corporation, National Engineering Research Center of Microbial Medicine, Hebei Industry Microbial Metabolic Technology Innovation Centre, Shijiazhuang Microbial Drugs Technology Innovation Center, Hebei Synthetic Biology High-Energy-Level Technology Innovation Center, Shijiazhuang, Hebei, 050015, China.

出版信息

Phytochemistry. 2024 Jul;223:114119. doi: 10.1016/j.phytochem.2024.114119. Epub 2024 May 3.

DOI:10.1016/j.phytochem.2024.114119

PMID:38705266

Abstract

Six previously undescribed prenylated indole diketopiperazine alkaloids, talaromyines A-F (1-6), were isolated from the marine-derived fungus Talaromyces purpureogenus SCSIO 41517. Their structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data including NMR, HR-ESI-MS, and electronic circular dichroism calculations, together with chemical analysis of hydrolysates. Compounds 1-5 represent the first example of spirocyclic indole diketopiperazines biosynthesized from the condensation of L-tryptophan and L-alanine. Compounds 2 and 4-5 showed selective inhibitory activities against phosphatases TCPTP and MEG2 with IC value of 17.9-29.7 μM, respectively. Compounds 4-5 exhibited mild cytotoxic activities against two human cancer cell lines H1975 and HepG-2.

摘要

从海洋来源真菌塔玛多粘菌 SCSIO 41517 中分离到 6 种以前未描述的prenylated indole diketopiperazine 生物碱，分别命名为 talaromyines A-F (1-6)。基于包括 NMR、HR-ESI-MS 和电子圆二色性计算在内的综合光谱数据以及水解产物的化学分析，确定了它们的结构包括绝对构型。化合物 1-5 代表了第一个由 L-色氨酸和 L-丙氨酸缩合生成的 spirocyclic indole diketopiperazines 的生物合成。化合物 2 和 4-5 对磷酸酶 TCPTP 和 MEG2 表现出选择性抑制活性，IC 值分别为 17.9-29.7 μM。化合物 4-5 对两种人癌细胞系 H1975 和 HepG-2 表现出温和的细胞毒性活性。