A 2H and 13C n.m.r. study of the biosynthesis of the polyketide isocoumarin residue of canescin in Aspergillus malignus from [1,2-13C2]-, and [1-13C, 2-2H3]acetates, [Me-13C, 2H3]methionine, 6,8-dihydroxy-3,7-dimethylisocoumarin, and 6,8-dihydroxy-7-formyl-3-methylisocoumarin

Lewis, Christopher N.; Staunton, James; Sunter, David

doi:10.1039/c39860000058

Cited by 3 publications

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“…Compound 1 has undergone investigation through chemical synthesis [ 19 ] and isotope labeling [ 20 , 21 ] since the 1980s, however, the enzyme responsible for the biosynthesis has not been reported until now. Our report about SlPKS4 is the first discovery of PKS responsible for compound 1 .…”

Section: Resultsmentioning

confidence: 99%

Activation of a Silent Polyketide Synthase SlPKS4 Encoding the C7-Methylated Isocoumarin in a Marine-Derived Fungus Simplicillium lamellicola HDN13-430

Yu,

Liu,

et al. 2023

Marine Drugs

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Coumarins, isocoumarins and their derivatives are polyketides abundant in fungal metabolites. Although they were first discovered over 50 years ago, the biosynthetic process is still not entirely understood. Herein, we report the activation of a silent nonreducing polyketide synthase that encodes a C7-methylated isocoumarin, similanpyrone B (1), in a marine-derived fungus Simplicillium lamellicola HDN13-430 by heterologous expression. Feeding studies revealed the host enzymes can change 1 into its hydroxylated derivatives pestapyrone A (2). Compounds 1 and 2 showed moderate radical scavenging activities with ED50 values of 67.4 µM and 104.2 µM. Our discovery fills the gap in the enzymatic elucidation of naturally occurring C7-methylated isocoumarin derivatives.

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Section: Resultsmentioning

confidence: 99%