Direct Identification of α-Bisabolol Enantiomers in an Essential Oil Using a Combined Ion Mobility-Mass Spectrometry/Quantum Chemistry Approach.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2020-03-26 DOI:10.1021/acs.jnatprod.9b00982

Erik Laurini, Stéphane Andreani, Alain Muselli, Sabrina Pricl, Aura Tintaru

引用次数: 0

Abstract

Enantiomer-specific identification of chiral molecules in natural extracts is a challenging task, as many routine analytical techniques fail to provide selectivity in multicomponent mixtures. Here we describe an alternative approach, based on the combination of ion mobility-mass spectrometry (IM-MS) and quantum chemistry (QM), for the direct enantiomers differentiation in crude essential oils. The identification of α-bisabolol enantiomers contained in the raw essential oil (EO) from the Corsican Xanthium italicum fruits is reported as a proof-of-concept. Accordingly, IM-MS experiments performed in Ag⁺-doped methanol revealed the presence of both (+)- and (-)-α-bisabolol in the EO, while molecular simulations provided the structures of the two α-bisabolol enantiomer silver(I) adducts.

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利用离子迁移率-质谱法/量子化学组合方法直接鉴定精油中的α-双香叶醇对映体

天然提取物中手性分子的对映体特异性鉴定是一项极具挑战性的任务，因为许多常规分析技术无法在多组分混合物中提供选择性。在此，我们介绍一种基于离子迁移质谱（IM-MS）和量子化学（QM）相结合的替代方法，用于直接区分粗精油中的对映体。作为概念验证，报告了对科西嘉黄刺玫果实生精油（EO）中所含的α-二苯甲醇对映体的鉴定。因此，在掺有 Ag+ 的甲醇中进行的 IM-MS 实验显示，精油中同时存在 (+)- 和 (-)-α-bisabolol 对映体，而分子模拟提供了两种 α-bisabolol 对映体银（I）加合物的结构。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.