Peniapyrones A–I, Cytotoxic Tricyclic-Fused α‑Pyrone Derivatives from an Endophytic Penicillium brefeldianum F4a

Five cyclopenta­[d]­pyrano­[4,3-b]­pyran-1,7­(6H)-dione 6/6/5-fused tricyclic ring system containing metabolites peniapyrones A–E (1–5), and four previously undescribed cyclopenta­[4,5]­furo­[3,2-c]­pyran-1-one 6/5/5-fused tricyclic ring system containing compounds peniapyrones F–I (6–9), were isola...

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Published inJournal of natural products (Washington, D.C.) Vol. 87; no. 6; pp. 1643 - 1651
Main Authors Bai, Yan, Ma, Xiaodong, Ren, Duo, Yu, Guoqing, Hu, Jiangchun, Hua, Huiming, Pan, Huaqi
Format Journal Article
LanguageEnglish
Published United States American Chemical Society and American Society of Pharmacognosy 28.06.2024
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Summary:Five cyclopenta­[d]­pyrano­[4,3-b]­pyran-1,7­(6H)-dione 6/6/5-fused tricyclic ring system containing metabolites peniapyrones A–E (1–5), and four previously undescribed cyclopenta­[4,5]­furo­[3,2-c]­pyran-1-one 6/5/5-fused tricyclic ring system containing compounds peniapyrones F–I (6–9), were isolated from the endophytic Penicillium brefeldianum F4a. Their structures, including absolute configurations, were determined through spectroscopic analysis and quantum chemical calculations. Peniapyrones D (4) and E (5) were a pair of diastereoisomers. Compounds 1, 3, and 5–9 showed cytotoxic activity against AsPC-1, CRL-2234, and MCF-7 cancer cell lines. Compounds 1, 3, 6, 8, and 9 inhibited the Kirsten rat sarcoma viral oncogene homologue (KRAS) mutant AsPC-1 cell line.
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ISSN:0163-3864
1520-6025
1520-6025
DOI:10.1021/acs.jnatprod.4c00383