Monoterpenoid indole alkaloids from the stem barks of Voacanga africana and their chemotaxonomic significance

IF 1.4 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Biochemical Systematics and Ecology Pub Date : 2024-06-22 DOI:10.1016/j.bse.2024.104863

Malong Qin , Wen Gao , Haiyin Wang , Shanze Yin , Jianlin Hu , Weimin Gao , Caifeng Ding

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Abstract

The phytochemical investigation of the stem barks of Voacanga africana resulted in the isolation of fifteen known monoterpenoid indole alkaloids (1–15). The structures of the alkaloids were determined by comparison of their physical and spectroscopic data with those reported in literature. Twelve of these metabolites (4–15) were previously unreported within the genus Voacanga, thus they can serve as chemotaxonomic markers for V. africana to differentiate between V. africana from other species of the genus Voacanga. The alkaloids 3-oxoconopharyngine (6), ervahainanmine (10), crassanine (14) and conolobine A (15) hold the potential to serve as chemical markers for distinguishing V. africana from other family species. Furthermore, compounds 3, 6, 10, 12 showed potential antimicrobial activities against Candida albicans and Bacillus subtilis with MIC values of 6.25–12.50 μg/mL.

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非洲疣螈茎皮中的单萜吲哚生物碱及其化学分类学意义

对 Voacanga africana 的茎皮进行植物化学研究后，分离出 15 种已知的单萜吲哚生物碱（1-15）。通过将这些生物碱的物理和光谱数据与文献报道的数据进行比较，确定了它们的结构。这些代谢物（4-15）中有 12 种以前在 Voacanga 属中未见报道，因此它们可以作为 V. africana 的化学分类标记，以区分 V. africana 和 Voacanga 属的其他物种。生物碱 3-oxoconopharyngine（6）、ervahainanmine（10）、crassanine（14）和 conolobine A（15）有可能成为区分 V. africana 和其他科物种的化学标记。此外，化合物 3、6、10 和 12 对白色念珠菌和枯草芽孢杆菌具有潜在的抗菌活性，其 MIC 值为 6.25-12.50 μg/mL。

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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.