Chlorotheolides A and B, Spiroketals Generated via Diels–Alder Reactions in the Endophytic Fungus Pestalotiopsis theae

Chlorotheolides A (1) and B (2), two new spiroketals possessing the unique [4,7]­methanochromene and dispiro-trione skeletons, respectively, and their putative biosynthetic precursors, 1-undecen-2,3-dicarboxylic acid (3) and maldoxin (4), were isolated from the solid substrate fermentation of the pl...

Full description

Saved in:
Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2016-10, Vol.79 (10), p.2616-2623
Main Authors: Liu, Ling, Han, Yu, Xiao, Junhai, Li, Li, Guo, Liangdong, Jiang, Xuejun, Kong, Lingyi, Che, Yongsheng
Format: Article
Language:English
Subjects:
Ascomycota - chemistry
China
Cycloaddition Reaction
Drug Screening Assays, Antitumor
Furans - chemistry
HeLa Cells
Humans
Lactones - metabolism
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plants
Spiro Compounds - chemistry
Spiro Compounds - isolation & purification
Spiro Compounds - metabolism
Stereoisomerism
Xylariales - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Chlorotheolides A (1) and B (2), two new spiroketals possessing the unique [4,7]­methanochromene and dispiro-trione skeletons, respectively, and their putative biosynthetic precursors, 1-undecen-2,3-dicarboxylic acid (3) and maldoxin (4), were isolated from the solid substrate fermentation of the plant endophytic fungus Pestalotiopsis theae (N635). Their structures were elucidated based on NMR spectroscopic data and electronic circular dichroism calculations. Biogenetically, compounds 1 and 2 could be generated from the co-isolated 3 and 4 via Diels–Alder reactions. Chlorotheolide (2) showed an antiproliferative effect against the human tumor cell line HeLa and induced an autophagic process in the cells.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00550