Characterization of a new jasmonate derivative and chemotaxonomical significance of secondary metabolites in the seeds of black soybean (Glycine max)

IF 1.4 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology Pub Date : 2025-06-09 DOI:10.1016/j.bse.2025.105060

Nguyen Viet Phong , Cai-Yi Wang , Sung Don Lim , Seo Young Yang

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引用次数: 0

Abstract

A comprehensive phytochemical investigation of black soybean (Glycine max) led to the isolation of five compounds, including a new jasmonate derivative (1), a β-sitosterol glucoside derivative (2), two isoflavone glycosides (3 and 4), and an aurone glycoside derivative (5). Their chemical structures were determined using nuclear magnetic resonance (NMR) spectroscopy and comparison with previously reported data. The absolute configuration of the new jasmonate derivative (1) was determined through density functional theory calculations of NMR chemical shifts and DP4+ probability analysis. Additionally, marsuposide (5) was identified in black soybean for the first time, expanding the known chemical profile of this crop. Notably, the occurrence of these metabolites provides potential chemotaxonomic markers within the Fabaceae family, highlighting unique metabolic traits of black soybean. These findings contribute not only to the understanding of the secondary metabolism of the species but also to broader discussions on the diversification of legume-specific phytochemicals. The potential agricultural and biological significance of these metabolites is discussed, along with their chemotaxonomic significance, offering insights into the phytochemical composition of black soybean and its relevance to crop improvement and plant classification.

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一种新的茉莉酸衍生物的鉴定及其黑豆种子次生代谢产物的化学分类意义

对黑大豆（Glycine max）进行了全面的植物化学研究，分离出5个化合物，包括一个新的茉莉酸衍生物(1)、一个β-谷甾醇葡萄糖苷衍生物(2)、两个异黄酮苷（3和4）和一个紫金酮苷衍生物(5)。它们的化学结构是用核磁共振（NMR）光谱测定的，并与先前报道的数据进行了比较。通过核磁共振化学位移的密度泛函理论计算和DP4+概率分析确定了新茉莉酸衍生物(1)的绝对构型。此外，首次在黑大豆中鉴定出马鞍子苷(5)，扩大了该作物的已知化学概况。值得注意的是，这些代谢物的出现为豆科植物提供了潜在的化学分类标记，突出了黑豆独特的代谢特征。这些发现不仅有助于了解该物种的次生代谢，而且有助于更广泛地讨论豆类特异性植物化学物质的多样性。讨论了这些代谢物的潜在农业和生物学意义，以及它们的化学分类意义，为黑大豆的植物化学组成及其与作物改良和植物分类的相关性提供了见解。

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来源期刊

Biochemical Systematics and Ecology 生物-进化生物学

CiteScore

3.00

自引率

12.50%

发文量

147

审稿时长

43 days

期刊介绍： Biochemical Systematics and Ecology is devoted to the publication of original papers and reviews, both submitted and invited, in two subject areas: I) the application of biochemistry to problems relating to systematic biology of organisms (biochemical systematics); II) the role of biochemistry in interactions between organisms or between an organism and its environment (biochemical ecology). In the Biochemical Systematics subject area, comparative studies of the distribution of (secondary) metabolites within a wider taxon (e.g. genus or family) are welcome. Comparative studies, encompassing multiple accessions of each of the taxa within their distribution are particularly encouraged. Welcome are also studies combining classical chemosystematic studies (such as comparative HPLC-MS or GC-MS investigations) with (macro-) molecular phylogenetic studies. Studies that involve the comparative use of compounds to help differentiate among species such as adulterants or substitutes that illustrate the applied use of chemosystematics are welcome. In contrast, studies solely employing macromolecular phylogenetic techniques (gene sequences, RAPD studies etc.) will be considered out of scope. Discouraged are manuscripts that report known or new compounds from a single source taxon without addressing a systematic hypothesis. Also considered out of scope are studies using outdated and hard to reproduce macromolecular techniques such as RAPDs in combination with standard chemosystematic techniques such as GC-FID and GC-MS.