Densely Functionalized Macrocyclic Sesquiterpene Pyridine Alkaloids from Maytenus austroyunnanensis

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-09-20 DOI:10.1021/acs.jnatprod.3c00504

Kai-Long Ji, Yao-Yue Fan, Qi Gong, Qun-Fang Liu, Ming-Jun Cui, Kai-Cong Fu, Hai-Yan Zhang* and Jian-Min Yue*,

引用次数: 0

Abstract

Eleven densely functionalized new dihydro-β-agarofuran sesquiterpenoid derivatives, named maytenoids A–K (1–11), as well as one known analog, were isolated and characterized from Maytenus austroyunnanensis. Their structures were assigned based on analysis of spectroscopic data and X-ray crystallography. Compounds 1–9 are macrocyclic sesquiterpene pyridine alkaloids generated by the respective acylation of the hydroxy groups at C-3 and C-13 of dihydro-β-agarofuran sesquiterpenoids via diverse pyridine dicarboxylic acids. Compounds 1, 2, 5–10, and 12 exhibited significant inhibitory effects on NO production at 10 μM in lipopolysaccharide (LPS)-stimulated BV2 cells.

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云南梅藤大环倍半萜吡啶生物碱的高密度功能化研究

从澳大利亚Maytenus austroyunensis中分离并表征了11种新的高度官能化的二氢-β-无盖呋喃倍半萜衍生物，命名为maytenoids A–K（1–11），以及一种已知的类似物。根据光谱数据和X射线晶体学的分析，确定了它们的结构。化合物1–9是大环倍半萜吡啶生物碱，通过不同的吡啶二羧酸分别酰化二氢-β-琼脂倍半萜C-3和C-13的羟基而产生。化合物1、2、5-10和12对脂多糖（LPS）刺激的BV2细胞中10μM的NO产生表现出显著的抑制作用。

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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.