Breviane Spiroditerpenoids with Anti-inflammatory and Antiviral Activities from Deep-Sea-Derived Fungus Penicillium sp. F59.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-12-17 DOI:10.1021/acs.jnatprod.4c00997

Yinghui Lv, Wenping Song, Zongze Shao, Tianlei Ying, Bihong Hong, Wenjing Tian, Siwen Niu

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Abstract

Twelve new breviane spiroditerpenoids, namely, chrysobreviones A-L (1-12), together with seven structurally related analogues (13-19) were isolated from the EtOAc extract of the fermented cultures of deep-sea-derived fungus Penicillium sp. F59. These structures including absolute configurations were resolved on the basis of extensive analysis of NMR spectroscopic data and HRESIMS, in association with experimental and calculated ECD data as well as the modified Mosher's method. Compound 1 represented the first breviane derivative containing an unusual octahydrodifuro[2,3-b:2',3'-d]furan moiety, while 7 and 9 were the first breviones featuring an epoxy ring and an 18-hydroxymethyl group, respectively. The anti-inflammatory and antiviral activities of compounds 1-19 were evaluated. Compounds 1, 8, 16, and 17 showed inhibitory effects against NO secretion in LPS-activated Raw264.7 macrophage cells with IC₅₀ values ranging from 1.4 to 12.9 μM, while 1 and 7 exhibited antiviral effects against severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) omicron subvariant BA.2 pseudovirus with IC₅₀ values of 8.5 and 10.3 μM, respectively.

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从深海源真菌青霉菌 F59 的发酵培养物的乙酸乙酯提取物中分离出了 12 种新的囟素螺虫烷类化合物，即 Chrysobreviones A-L (1-12)，以及 7 种结构相关的类似物 (13-19)。在对核磁共振光谱数据和 HRESIMS 进行广泛分析的基础上，结合实验和计算的 ECD 数据以及改进的 Mosher 方法，对这些结构（包括绝对构型）进行了解析。化合物 1 是首个含有不常见的八氢二呋喃并[2,3-b:2',3'-d]呋喃分子的囟素衍生物，而 7 和 9 则分别是首个具有环氧环和 18- 羟甲基的囟素。对化合物 1-19 的抗炎和抗病毒活性进行了评估。化合物 1、8、16 和 17 对 LPS 激活的 Raw264.7 巨噬细胞的 NO 分泌有抑制作用，IC50 值在 1.4 到 12.9 μM 之间；而 1 和 7 对严重急性呼吸系统综合征冠状病毒-2（SARS-CoV-2）奥米克隆亚变种 BA.2 伪病毒有抗病毒作用，IC50 值分别为 8.5 和 10.3 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.