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

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-06-07 DOI:10.1021/acs.jnatprod.4c00383

Yan Bai, Xiaodong Ma, Duo Ren, Guoqing Yu, Jiangchun Hu, Huiming Hua and Huaqi Pan*,

引用次数: 0

Abstract

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

研究人员从内生青霉菌(Penicillium brefeldianum F4a)中分离出了五种环戊并[d]吡喃并[4,3-b]吡喃-1,7(6H)-二酮 6/6/5-融合三环系统含代谢物五并吡喃酮 A-E (1-5)，以及四种以前未曾描述过的环戊并[4,5]呋喃并[3,2-c]吡喃-1-酮 6/5/5-融合三环系统含化合物五并吡喃酮 F-I (6-9)。通过光谱分析和量子化学计算确定了它们的结构，包括绝对构型。青霉烯酮 D（4）和 E（5）是一对非对映异构体。化合物 1、3 和 5-9 对 AsPC-1、CRL-2234 和 MCF-7 癌细胞株具有细胞毒性活性。化合物 1、3、6、8 和 9 对 Kirsten 大鼠肉瘤病毒癌基因同源物（KRAS）突变的 AsPC-1 细胞系有抑制作用。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.