{"title":"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","authors":"Meriem Belaid , Soumia Mouffouk , Sonia Chabani , Chaima Mouffouk , Mohammed Benkhaled , Hamada Haba","doi":"10.1016/j.bse.2024.104874","DOIUrl":null,"url":null,"abstract":"<div><p>The chemical study of <em>Centaurea granatensis</em> Boiss. ex DC. allowed the isolation and structural elucidation of eighteen secondary metabolites (<strong>1</strong>–<strong>18)</strong> from ethyl acetate (EtOAc) and <em>n</em>-butanol (<em>n</em>-BuOH) extracts. These compounds are divided into one new epoxylignan glucoside <strong>(1)</strong> and seventeen known phytochemicals including seven flavonoids <strong>(2</strong>–<strong>8)</strong>, four triterpenes <strong>(9</strong>–<strong>12)</strong>, and six phytosterols <strong>(13</strong>–<strong>18)</strong>. Structures of the isolates were identified using various spectroscopic methods, namely 1D NMR (<sup>1</sup>H and <sup>13</sup>C), 2D NMR (HSQC, <sup>1</sup>H–<sup>1</sup>H 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 <em>C. granatensis</em>. Apigenin <strong>(3)</strong> could be used as a chemotaxonomic marker of this genus due to its presence in approximately forty plant species. Furthermore, tiliroside <strong>(2)</strong> and stigmasteryl-3-<em>O</em>-<em>β</em>-D-glucoside-6′-palmitate <strong>(18)</strong> were first detected in <em>Centaurea</em> genus, but had previously been found in species of the Asteraceae family. Additionally, the chemotaxonomic significance of all isolated molecules was fully discussed.</p></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"116 ","pages":"Article 104874"},"PeriodicalIF":1.4000,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A new 7,9′-monoepoxylignan glucoside and other phytochemicals from Centaurea granatensis and their chemotaxonomic significance\",\"authors\":\"Meriem Belaid , Soumia Mouffouk , Sonia Chabani , Chaima Mouffouk , Mohammed Benkhaled , Hamada Haba\",\"doi\":\"10.1016/j.bse.2024.104874\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The chemical study of <em>Centaurea granatensis</em> Boiss. ex DC. allowed the isolation and structural elucidation of eighteen secondary metabolites (<strong>1</strong>–<strong>18)</strong> from ethyl acetate (EtOAc) and <em>n</em>-butanol (<em>n</em>-BuOH) extracts. These compounds are divided into one new epoxylignan glucoside <strong>(1)</strong> and seventeen known phytochemicals including seven flavonoids <strong>(2</strong>–<strong>8)</strong>, four triterpenes <strong>(9</strong>–<strong>12)</strong>, and six phytosterols <strong>(13</strong>–<strong>18)</strong>. Structures of the isolates were identified using various spectroscopic methods, namely 1D NMR (<sup>1</sup>H and <sup>13</sup>C), 2D NMR (HSQC, <sup>1</sup>H–<sup>1</sup>H 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 <em>C. granatensis</em>. Apigenin <strong>(3)</strong> could be used as a chemotaxonomic marker of this genus due to its presence in approximately forty plant species. Furthermore, tiliroside <strong>(2)</strong> and stigmasteryl-3-<em>O</em>-<em>β</em>-D-glucoside-6′-palmitate <strong>(18)</strong> were first detected in <em>Centaurea</em> genus, but had previously been found in species of the Asteraceae family. Additionally, the chemotaxonomic significance of all isolated molecules was fully discussed.</p></div>\",\"PeriodicalId\":8799,\"journal\":{\"name\":\"Biochemical Systematics and Ecology\",\"volume\":\"116 \",\"pages\":\"Article 104874\"},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-07-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Biochemical Systematics and Ecology\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0305197824000929\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biochemical Systematics and Ecology","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0305197824000929","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
A new 7,9′-monoepoxylignan glucoside and other phytochemicals from Centaurea granatensis and their chemotaxonomic significance
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.
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.
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