Daldipyrenones A-C: Caged [6,6,6,6,6] Polyketides Derived from an Endolichenic Fungus <i>Daldinia pyrenaica</i> 047188
- 주제(기타) Chemistry, Organic
- 설명문(일반) [Lee, Seungjin; Park, In Guk; Choi, Jin Won; Noh, Minsoo; Shim, Sang Hee] Seoul Natl Univ, Nat Prod Res Inst, Coll Pharm, Seoul 08826, South Korea; [Son, Jin Young; Lee, Jin Woo] Duksung Womens Univ, Coll Pharm, Seoul 01369, South Korea; [Hur, Jae-Seoun] Sunchon Natl Univ, Korean Lichen Res Inst KoLRI, Sunchon 57922, South Korea; [Kim, Youngmee; Nam, Sang-Jip] Ewha Womans Univ, Coll Nat Sci, Dept Chem & Nanosci, Seoul 03760, South Korea; [Kang, Hahk-Soo] Konkuk Univ, Dept Biomed Sci & Engn, Seoul 05029, South Korea; [Deyrup, Stephen T.] Siena Coll, Dept Chem & Biochem, Loudonville, NY 12211 USA
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2023
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000211565
- 본문언어 영어
- Published As https://doi.org/10.1021/acs.orglett.3c02583
- PubMed 37650559
초록/요약
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.
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