Canescones A-E: aromatic polyketide dimers with PTP1B inhibitory activity from Penicillium canescens

被引：13

作者：

Zang, Yi ^{[1
]}

Gong, Yi-Hua ^{[1
]}

Li, Xu-Wen ^{[2
]}

Li, Xiao-Nian ^{[3
]}

Liu, Jun-Jun ^{[1
]}

Chen, Chun-Mei ^{[1
]}

Zhou, Yuan ^{[1
]}

Gu, Liang-Hu ^{[1
]}

Luo, Zeng-Wei ^{[1
]}

Wang, Jian-Ping ^{[1
]}

Sun, Wei-Guang ^{[1
]}

Zhu, Hu-Cheng ^{[1
]}

Zhang, Yong-Hui ^{[1
]}

机构：

[1] Huazhong Univ Sci & Technol, Sch Pharm, Tongji Med Coll, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Hubei, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

[3] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 18期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

NATURAL-PRODUCTS; BIOMIMETIC SYNTHESIS; INSULIN SENSITIVITY; PROTEIN;

D O I：

10.1039/c9qo00820a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three pairs of enantiomers (+/-)-canescones A-C (1-3), along with a pair of stereoisomers canescones D (4) and E (5), aromatic polyketide dimers bearing unprecedented 5/6/6/6/5 heterocyclic chemical architectures with a rare pentacyclic dihydrobenzo[1,4]dioxine core, were isolated from the fungus Penicillium canescens. Structure elucidation unambiguously suggests that 1 and 2 feature a new cyclopentanone ring A rather than a pyrrolidinone or furanone ring present in 3-5. All compounds were assayed for PTP1B inhibitory activity, and their hypothetical biosynthetic pathways were proposed.

引用

页码：3274 / 3281

页数：8

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