Aromatic Polyketide Production in Cordyceps indigotica, an Entomopathogenic Fungus, Induced by Exposure to a Histone Deacetylase Inhibitor
- 5 April 2012
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (8), 2006-2009
- https://doi.org/10.1021/ol3005062
Abstract
Cultivation of Cordyceps indigotica, an entomopathogenic fungus, in the presence of suberoyl bis-hydroxamic acid (an HDAC inhibitor) greatly activated its polyketide synthesis apparatus to afford six novel aromatic polyketides, indigotides C-F (1-4), 13-hydroxyindigotide A (5), and 8-O-methylindigotide B (6). The structures of these compounds were determined by NMR spectroscopic analyses. Among the compounds, indigotides C-E (1-3) possessed unprecedented dimeric polyketide frameworks possibly generated via a [4 + 2] cycloaddition or Michael type reaction.Keywords
This publication has 9 references indexed in Scilit:
- Aromatic polyketide glycosides from an entomopathogenic fungus, Cordyceps indigoticaTetrahedron Letters, 2012
- Advances in Aspergillus secondary metabolite research in the post-genomic eraNatural Product Reports, 2012
- Histone Deacetylase Inhibitors as a Tool to Up-Regulate New Fungal Biosynthetic Products: Isolation of EGM-556, a Cyclodepsipeptide, from Microascus sp.Organic Letters, 2010
- Chemical Epigenetics Alters the Secondary Metabolite Composition of Guttate Excreted by an Atlantic-Forest-Soil-Derived Penicillium citreonigrumJournal of Natural Products, 2010
- Chemical induction of silent biosynthetic pathway transcription in Aspergillus nigerJournal of Industrial Microbiology & Biotechnology, 2009
- Triggering cryptic natural product biosynthesis in microorganismsOrganic & Biomolecular Chemistry, 2009
- A chemical epigenetics approach for engineering the in situbiosynthesis of a cryptic natural product from Aspergillus nigerOrganic & Biomolecular Chemistry, 2008
- Epigenetic remodeling of the fungal secondary metabolomeOrganic & Biomolecular Chemistry, 2008
- Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoidsPhytochemistry, 2005