DMOA-based meroterpenoids with diverse scaffolds from the sponge-associated fungus Penicillium brasilianum |
| |
Authors: | Jianping Zhang Yifan Wu Bochuan Yuan Dong Liu Kui Zhu Jian Huang Peter Proksch Wenhan Lin |
| |
Affiliation: | 1. State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University, Beijing, 100191, PR China;2. College of Veterinary Medicine, China Agricultural University, Beijing 100193, PR China;3. Institute für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität üsseldorf, 40225 Düsseldorf, Germany |
| |
Abstract: | Bioinformatics analysis of the synthetic gene clusters in association with the qRT-PCR detection led to speculate a marine derived fungus, Penicillium brasilianum WZXY-m122-9, to be potential to produce meroterpenoids. Chromatographic separation of the EtOAc extract of this fungal strain on a large-scale fermentation resulted in the isolation of six new DMOA-related meroterpenoids, namely brasilianoids G?L (1–6), together with nine known meroterpenes. Their structures were determined by extensive analyses of spectroscopic data, including the X-ray diffraction and the ECD data for configurational assignment. Brasilianoid G is characterized by the presence of an unprecedented scaffold bearing a 6/6/5/5/5 pentacyclic nucleus, while brasilianoid K possessing a 7/6/6/6/5 pentacyclic system is uncommonly found from nature. The biogenetic relationship among the isolated compounds was postulated based on the comparative analyses of gene clusters. Brasilianoid L (6), austinol (12), and dehydroaustin (14) exhibited significant inhibition against bacteria invasion into host cells, that was suggested to be mediated by preventing the polymerization of actin in the host cells. |
| |
Keywords: | Marine fungus DMOA-related meroterpenoids Brasilianoids G-L Inhibition of bacteria invasion |
本文献已被 ScienceDirect 等数据库收录! |
|