Daldipyrenones A-C: Caged [6,6,6,6,6] Polyketides Derived from an Endolichenic Fungus Daldinia pyrenaica 047188

Seungjin Lee, In Guk Park, Jin Won Choi, Jin Young Son, Jin Woo Lee, Jae Seoun Hur, Youngmee Kim, Sang Jip Nam, Hahk Soo Kang, Stephen T. Deyrup, Minsoo Noh, Sang Hee Shim

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Abstract

Daldipyrenones A-C (1-3), three unprecedented caged xanthone [6,6,6,6,6] polyketides featuring a spiro-azaphilone unit, were discovered from an endolichenic fungus, Daldinia pyrenaica 047188. The structures of 1-3 were determined by using spectroscopic analysis and chemical derivatization. Daldipyrenones are likely derived by combining a chromane biosynthesis intermediate, 1-(2,6-dihydroxyphenyl)but-2-en-2-one, and a spiro-azaphilone, pestafolide A, via radical coupling or Michael addition to form a bicyclo[2.2.2]octane ring. Genome sequencing of the strain revealed two separate biosynthetic gene clusters responsible for forming two biosynthetic intermediates, suggesting a proposed biosynthetic pathway. Daldipyrenone A (1) exhibited significant antimelanogenic activity with lower EC50’s than positive controls and moderate adiponectin-secretion promoting activity.

Original languageEnglish
Pages (from-to)6725-6729
Number of pages5
JournalOrganic Letters
Volume25
Issue number36
DOIs
StatePublished - 15 Sep 2023

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