Journal
TETRAHEDRON
Volume 75, Issue 14, Pages 2193-2205Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.02.037
Keywords
Marine fungus; Penicillium brasilianum WZXY-m122-9; DMOA-related meroterpenoids; Brasilianoids G-L; Inhibition of bacteria invasion
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Funding
- National Key Research and Development Program of China [2018ZX09711001-001-008, 2015CB755906, DY135-B2-05]
- National Natural Science Foundation of China [21861142006, 81630089, 81872793, U1606403, 21502004]
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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. (C) 2019 Elsevier Ltd. All rights reserved.
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