Penicamins A-L, Polyoxygenated Diterpenes from Penicillium camemberti JSB-7212.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-10-25 Epub Date: 2024-10-16 DOI:10.1021/acs.jnatprod.4c00700

Jiao Pei, Jin-Ling Chang, Qian-Xi Ouyang, Xiao-Gang Peng, Xianggao Meng, An Jin, Han-Li Ruan

引用次数: 0

Abstract

Penicamins A-L (1-12), 12 highly oxygenated novel diterpenes, were obtained from the fungus Penicillium camemberti JSB-7212. Compounds 1-12 share the same 7/6/5 tricyclic skeleton as valparane-type diterpenes but differ in the absolute configurations at C-7, C-11, and C-14, as well as in the oxidation levels at C-6 and C-8, which were determined through extensive spectroscopic data interpretation. Stereochemical assignments of compounds 1, 2, and 4-12 were established by single-crystal X-ray diffraction, and the absolute configuration of 3 was determined by analysis of the NOESY data and biogenetic consideration. Compounds 2 and 3 were immunosuppressive against lipopolysaccharide (LPS)-induced B cells, with IC₅₀ values of 3.0 and 7.9 μM, respectively. They also moderately suppressed concanavalin A (ConA)-induced T cell proliferation, with IC₅₀ values of 19 and 20 μM, respectively.

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青霉素 A-L，来自卡门贝青霉 JSB-7212 的聚氧二萜。

从真菌 Penicillium camemberti JSB-7212 中获得了青霉酰胺 A-L（1-12），这是 12 种高含氧的新型二萜。化合物 1-12 与缬草烷型二萜具有相同的 7/6/5 三环骨架，但在 C-7、C-11 和 C-14 的绝对构型以及 C-6 和 C-8 的氧化程度上存在差异，这些差异是通过大量光谱数据解读确定的。化合物 1、2 和 4-12 的立体化学分配是通过单晶 X 射线衍射确定的，化合物 3 的绝对构型是通过 NOESY 数据分析和生物遗传学考虑确定的。化合物 2 和 3 对脂多糖（LPS）诱导的 B 细胞具有免疫抑制作用，IC50 值分别为 3.0 和 7.9 μM。它们还能中度抑制由 concanavalin A（ConA）诱导的 T 细胞增殖，IC50 值分别为 19 和 20 μM。

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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.