Unravelling the Enantiomeric Distribution of Key Sandalwood Sesquiterpenoids by Enantioselective Gas Chromatography and Molecular Rotational Resonance

IF 3.7 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2026-09-25 Epub Date: 2026-09-04 DOI:10.1021/acs.jnatprod.6c00530

Cecilia L. Cagliero, Reilly E. Sonstrom, Carlo Bicchi, Norbert A. Braun, Daniel Joulain, Nicolas Baldovini

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Abstract

The enantiomeric distribution of α- and β-santalol in various Santalum and Osyris species of different origins was determined by the combination of enantioselective gas chromatography and chiral tagging molecular rotational resonance spectroscopy, supported by the preparation of (+)- and (−)-α-santalol standards by total synthesis and isolation of (−)-β-santalol from Santalum album essential oil. (−)-β-Santalol was largely dominant in all Santalum essential oil samples (>99%) except for the mixtures of santalols produced by biotechnology. The enantiomeric distribution of α-santalol was much less in favor of the levorotatory enantiomer, contained in percentages up to 5 and 45% in some Santalum and Osyris samples, respectively. The olfactory evaluations of synthetic (+)- and (−)-α-santalol samples by a panel of 56 assessors showed that they were very weak to odorless for most panelists.

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对映选择气相色谱和分子旋转共振揭示檀香主要倍半萜的对映体分布

采用对映选择气相色谱法和手性标记分子旋转共振光谱相结合的方法，测定了不同产地桑菖蒲和山药中α-和β-桑他洛尔的对映体分布，并从桑菖蒲精油中分离(−)-β-桑他洛尔，合成(+)- α-桑他洛尔和(−)-α-桑他洛尔标准品。（−）-β-桑塔洛尔在所有桑塔洛尔精油样品中占绝大多数（>99%），但生物技术生产的桑塔洛尔混合物除外。α-桑他洛尔的对映体分布更倾向于左旋对映体，在桑他洛尔和奥西里斯样品中所占的比例分别高达5%和45%。由56人组成的评估小组对合成(+)-和(−)-α-桑他洛尔样品的嗅觉评估表明，对大多数小组成员来说，它们是非常弱到无味的。

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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.