Studies in the biosynthesis of fungal metabolites. 3. The biosynthesis of fungal perinaphthenones

Publisher Website
Google Scholar
Abstract
Possible alternative pathways of biosynthesis of the fungal perinaphthenones atrovenetin (C19H18O6), herqueinone (C20H20O7) and norherqueinone (C19H18O7) are discussed. 2. Penicillium herquei was found to incorporate sodium [l-14C]acetate and DL-[2-14C]mevalonic acid lactone into norherqueinone, in a manner consistent with the derivation of the perinaphthenone nucleus from acetate units and the C5 side chain from acetate or mevalonate. 3. A scheme is proposed for the biosynthesis of the aglycone C20H14O4 of the plant pigment haemOcorin, the only other known perinaphthenone from natural sources. This requires the coupling of one acetate and two shikimic-acid-derived C6-C3 units and involves an intermediate related to the plant product p-phydroxycinnamovl ferulovl methane (C20H18O5) which then undergoes cyclization.