Immunosuppressive Breviane Spiroditerpenoids from Penicillium bialowiezense Isolated from a Medicinal Plant.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-10-25 Epub Date: 2024-10-09 DOI:10.1021/acs.jnatprod.4c00782

Shu-Shuai Chen, Yuan Gao, Li Chen, Xiao Tong, Pei-Qian Wu, Yi Huang, Shi-Jun He, Jian-Min Yue, Bin Zhou

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Abstract

Breviane spiroditerpenoids are a small group of structurally interesting and complex meroterpenoids. This work focused on an endophytic fungus Penicillium bialowiezense ZBWPQ-27 that was isolated from a medicinal plant Euphorbia neriifolia, leading to the isolation of 15 breviane spiroditerpenoids with four types of polycyclic systems (1-6 and 9-17), and two new carotane sesquiterpenoids (7 and 8). The structures including absolute configurations of the new compounds 1-8 were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. In addition, the misassigned NMR data of several resonances of the 5-methyl-TAL motif (E ring) in those of known brevianes (9-15) were corrected by spectroscopic data analysis. Biological tests revealed that brevianes with the type A ring system (6/6/6/5/6) showed moderate to significant immunosuppressive activities, and compound 11 displayed the most potent inhibitory activities against concanavalin A (ConA)-induced T cell proliferation (IC₅₀ 4.1 ± 0.2 μM) and lipopolysaccharide (LPS)-induced B cell proliferation (IC₅₀ 4.6 ± 0.2 μM), with good SI values of 28 ± 2 and 25 ± 4, respectively.

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从一种药用植物中分离出的青霉 Bialowiezense 中提取的具有免疫抑制作用的 Breviane 疏螺旋体。

Breviane spiroditerpenoids 是一小群结构有趣而复杂的 meroterpenoids。这项研究的重点是从药用植物大戟（Euphorbia neriifolia）中分离出的一种内生真菌青霉菌（Penicillium bialowiezense ZBWPQ-27）中分离出了 15 种含有四种多环系统的布雷维恩螺二萜类化合物（1-6 和 9-17），以及两种新的胡萝卜烷倍半萜类化合物（7 和 8）。通过光谱数据分析和电子圆二色性（ECD）计算，阐明了新化合物 1-8 的结构（包括绝对构型）。此外，还通过光谱数据分析纠正了已知囟素化合物（9-15）中 5-甲基-TAL（E 环）图案的几个共振的错误核磁共振数据。生物测试表明，具有 A 型环系统（6/6/6/5/6）的囟素具有中等至显著的免疫抑制活性，其中化合物 11 对金刚烷胺（ConA）诱导的 T 细胞增殖（IC50 4.1 ± 0.2 μM）和脂多糖（LPS）诱导的 B 细胞增殖（IC50 4.6 ± 0.2 μM）具有最强的抑制活性，其良好 SI 值分别为 28 ± 2 和 25 ± 4。

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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.