Genome Mining-Driven Discovery of 5-Methylorsellinate-Derived Meroterpenoids from <i>Aspergillus funiculosus</i>
Dexiu Yan, Yudai Matsuda
Abstract
Heterologous expression of a cryptic gene cluster in the fungus Aspergillus funiculosus CBS 116.56 led to the discovery of four new meroterpenoids, funiculolides A–D (1–4), derived from the aromatic polyketide 5-methylorsellinic acid (5-MOA). Intriguingly, funiculolide D (4), the apparent end product of the pathway, harbors an unusual spirocyclopentanone moiety, which is synthesized by the oxidative rearrangement catalyzed by the ferrous iron and α-ketoglutarate-dependent dioxygenase FncG.
Topics & Concepts
ChemistryMoietyHeterologous expressionGene clusterStereochemistryPolyketideAspergillusHeterologousDioxygenaseFungusGeneFerrousBiochemistryBiosynthesisMicrobiologyBiologyOrganic chemistryBotanyRecombinant DNAMicrobial Natural Products and BiosynthesisSynthetic Organic Chemistry MethodsMetal-Catalyzed Oxygenation Mechanisms