A new 7,9′-monoepoxylignan glucoside and other phytochemicals from Centaurea granatensis and their chemotaxonomic significance

IF 1.4 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Biochemical Systematics and Ecology Pub Date : 2024-07-30 DOI:10.1016/j.bse.2024.104874

Meriem Belaid , Soumia Mouffouk , Sonia Chabani , Chaima Mouffouk , Mohammed Benkhaled , Hamada Haba

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Abstract

The chemical study of Centaurea granatensis Boiss. ex DC. allowed the isolation and structural elucidation of eighteen secondary metabolites (1–18) from ethyl acetate (EtOAc) and n-butanol (n-BuOH) extracts. These compounds are divided into one new epoxylignan glucoside (1) and seventeen known phytochemicals including seven flavonoids (2–8), four triterpenes (9–12), and six phytosterols (13–18). Structures of the isolates were identified using various spectroscopic methods, namely 1D NMR (¹H and ¹³C), 2D NMR (HSQC, ¹H–¹H COSY, HMBC, and NOESY), and mass spectrometry (HR-ESIMS), as well as by comparison with literature data. The obtained results showed the abundance of triterpenoids and flavonoids particularly flavones in C. granatensis. Apigenin (3) could be used as a chemotaxonomic marker of this genus due to its presence in approximately forty plant species. Furthermore, tiliroside (2) and stigmasteryl-3-O-β-D-glucoside-6′-palmitate (18) were first detected in Centaurea genus, but had previously been found in species of the Asteraceae family. Additionally, the chemotaxonomic significance of all isolated molecules was fully discussed.

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一种新的 7,9′-单环氧木犀草苷和其他植物化学物质及其化学分类学意义

的化学研究，从乙酸乙酯（EtOAc）和丁醇（-BuOH）提取物中分离并阐明了 18 种次级代谢产物（-）。这些化合物分为一种新的环木质素葡萄糖苷和 17 种已知的植物化学物质，包括 7 种黄酮类化合物、4 种三萜类化合物和 6 种植物甾醇。利用各种光谱方法，即一维核磁共振（H 和 C）、二维核磁共振（HSQC、H-H COSY、HMBC 和 NOESY）和质谱法（HR-ESIMS），以及与文献数据的比较，对分离物的结构进行了鉴定。结果表明，芹菜中含有丰富的三萜类化合物和黄酮类化合物，尤其是黄酮类化合物。芹菜甙可作为该属植物的化学分类标记，因为它存在于大约 40 种植物中。此外，桔梗甙和豆甾醇-3--D-葡萄糖甙-6′-棕榈酸酯也是首次在该属植物中发现，但此前曾在菊科植物中发现过。此外，还充分讨论了所有分离分子的化学分类学意义。

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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.