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Daldipyrenones A-C: Caged [6,6,6,6,6] Polyketides Derived from an Endolichenic Fungus <i>Daldinia pyrenaica</i> 047188
- Title
- Daldipyrenones A-C: Caged [6,6,6,6,6] Polyketides Derived from an Endolichenic Fungus <i>Daldinia pyrenaica</i> 047188
- Authors
- Lee, Seungjin; Park, In Guk; Choi, Jin Won; Son, Jin Young; Lee, Jin Woo; Hur, Jae-Seoun; Kim, Youngmee; Nam, Sang-Jip; Kang, Hahk-Soo; Deyrup, Stephen T.; Noh, Minsoo; Shim, Sang Hee
- Ewha Authors
- 김영미; 남상집
- SCOPUS Author ID
- 김영미; 남상집
- Issue Date
- 2023
- Journal Title
- ORGANIC LETTERS
- ISSN
- 1523-7060
1523-7052
- Citation
- ORGANIC LETTERS vol. 25, no. 36, pp. 6725 - 6729
- Publisher
- AMER CHEMICAL SOC
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- 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.
- DOI
- 10.1021/acs.orglett.3c02583
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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