Identification of Granatane Alkaloids from Duboisia myoporoides (Solanaceae) using Molecular Networking and Semisynthesis.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-08-23 Epub Date: 2024-07-22 DOI:10.1021/acs.jnatprod.4c00304

Quentin Dutertre, Philippe A Guy, Sylvain Sutour, Manuel C Peitsch, Nikolai V Ivanov, Gaetan Glauser, Stephan von Reuss

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Abstract

The Solanaceae plant family contains at least 98 genera and over 2700 species. The Duboisia genus stands out for its ability to produce pyridine and tropane alkaloids, which are relatively poorly characterized at the phytochemical level. In this study, we analyzed dried leaves of Duboisia spp. using supercritical CO₂ extraction and ultra-high-pressure liquid chromatography coupled to high-resolution tandem mass spectrometry, followed by feature-based molecular networking. Thirty-one known tropane alkaloids were putatively annotated, and the identity of six (atropine, scopolamine, anisodamine, aposcopolamine, apoatropine, and noratropine) were identified using reference standards. Two new granatane alkaloids connected in the molecular network were highlighted from Duboisia myoporoides, and their α-granatane tropate and α-granatane isovalerate structures were unambiguously established by semisynthesis.

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利用分子网络和半合成技术从茄科植物蓑衣中鉴定花生烷生物碱

茄科植物包含至少 98 个属和 2700 多个物种。蓑衣属植物因能产生吡啶和对位类生物碱而脱颖而出，但这些生物碱的植物化学特征相对较少。在这项研究中，我们采用超临界二氧化碳萃取和超高压液相色谱法，结合高分辨串联质谱法，分析了蓑衣属植物的干燥叶片，然后进行了基于特征的分子网络分析。对 31 种已知的托烷生物碱进行了推定注释，并利用参考标准鉴定了其中六种（阿托品、东莨菪碱、茴香胺、阿莨菪碱、阿朴托品和去甲托品）的身份。从蓑衣草中发现了两种分子网络连接的新的花生烷生物碱，并通过半合成法明确了它们的α-花生烷托贝特酸盐和α-花生烷异戊酸盐结构。

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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.