Structurally Diverse Alkaloids with Anti-Renal-Fibrosis Activity from the Centipede Scolopendra subspinipes mutilans

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-04-10 DOI:10.1021/acs.jnatprod.4c00044

Bin-Yuan Hu, Wu-Mei Sun, Cheng-Tian Tao, Sheng-Hong Li, Qiang Gao, Yong-Ming Yan and Yong-Xian Cheng*,

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Abstract

Twelve new alkaloids, scolopenolines A–L (1–7, 9–11, 13, 14), along with six known analogues, were isolated from Scolopendra subspinipes mutilans, identified by analysis of spectroscopic data and quantum chemical and computational methods. Scolopenoline A (1), a unique guanidyl-containing C₁₄ quinoline alkaloid, features a 6/6/5 ring backbone. Scolopenoline B (2) is a novel sulfonyl-containing heterodimer comprising quinoline and tyramine moieties. Scolopenoline G (7) presents a rare C₁₂ quinoline skeleton with a 6/6/5 ring system. Alkaloids 1, 8, 10, and 15–18 display anti-inflammatory activity, while 10 and 16–18 also exhibit anti-renal-fibrosis activity. Drug affinity responsive target stability and RNA-interference assays show that Lamp2 might be a potentially important target protein of 16 for anti-renal-fibrosis activity.

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蜈蚣中具有抗肾脏纤维化活性的结构多样的生物碱

通过光谱数据分析、量子化学和计算方法鉴定，从 Scolopendra subspinipes mutilans 分离出了 12 种新生物碱，即 Scolopenolines A-L（1-7、9-11、13、14）以及 6 种已知类似物。Scolopenoline A（1）是一种独特的含胍基 C14 喹啉生物碱，具有 6/6/5 环骨架。Scolopenoline B (2) 是一种新型含磺酰基的杂二聚体，由喹啉和酪胺分子组成。Scolopenoline G（7）具有罕见的 C12 喹啉骨架和 6/6/5 环系统。生物碱 1、8、10 和 15-18 具有抗炎活性，而 10 和 16-18 还具有抗肾脏纤维化活性。药物亲和力反应靶标稳定性和 RNA 干扰试验表明，Lamp2 可能是 16 具有抗肾脏纤维化活性的潜在重要靶蛋白。

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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.