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Identification of Granatane Alkaloids from Duboisia myoporoides (Solanaceae) using Molecular Networking and Semisynthesis
Journal of Natural Products ( IF 3.3 ) Pub Date : 2024-07-22 , DOI: 10.1021/acs.jnatprod.4c00304
Quentin Dutertre 1, 2 , Philippe A Guy 1 , Sylvain Sutour 3 , Manuel C Peitsch 1 , Nikolai V Ivanov 1 , Gaetan Glauser 3 , Stephan von Reuss 2, 3
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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.

中文翻译:


利用分子网络和半合成鉴定 Duboisia myoporoides(茄科)中的石榴碱生物碱



茄科植物家族包含至少 98 个属、2700 多个物种。 Duboisia属因其生产吡啶和托烷生物碱的能力而脱颖而出,而这些生物碱在植物化学水平上的表征相对较差。在这项研究中,我们分析了Duboisia spp 的干燥叶子。使用超临界CO 2萃取和超高压液相色谱与高分辨率串联质谱联用,然后进行基于特征的分子网络。假定对 31 种已知的托烷生物碱进行了注释,并使用参考标准鉴定了 6 种(阿托品、东莨菪碱、山莨菪碱、阿托菪碱、阿朴托品和去甲托品)的特性。从Duboisia myoporoides中突出显示了两种新的在分子网络中连接的石榴烷生物碱,并通过半合成明确地建立了它们的 α-石榴烷托品酸酯和 α-石榴烷异戊酸酯结构。
更新日期:2024-07-22
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