{"title":"A new ceramide and other constituents from Crinum ornatum (L.f.) Herb. (Amaryllidaceae) and their chemophenetic significance","authors":"Kedeu Kouvourbe , Christine Claire Waleguele , Yves Martial Mba Nguekeu , Elise Vanessa Ngouadjio Temgoua , Elodie Gaële Matheuda , Marie Germaine Tsepeupon Matchide , Marthe Aimée Tchuente Tchuenmogne , Arno Rusel Donfack Nanfack , Takeshi Kodama , Stijn Anthonissen , Wim Dehaen , Silvère Augustin Ngouela , Mathieu Tene , Morita Hiroyuki , Maurice Ducret Awouafack","doi":"10.1016/j.bse.2025.104991","DOIUrl":null,"url":null,"abstract":"<div><div>A previously undescribed ceramide, crinceramide (<strong>1</strong>), along with nineteen known compounds (<strong>2</strong>–<strong>20</strong>) were isolated from <em>Crinum ornatum</em> (L.f.) Herb. using column chromatography techniques over silica gel and Sephadex LH-20. The structure of the new compound was established by different spectroscopic methods including 1D and 2D-NMR, HRESI-MS and chemical conversions. The extract and fractions had strong activities on three human cancer cells (lung A549, breast MCF7, and cervical HeLa) with IC<sub>50</sub> from <0.63 to 9.76 μg/mL whereas compounds displayed IC<sub>50</sub> ranging from 39.79 to > 100 μM. Moupinamide (<strong>2</strong>) was the most active with IC<sub>50</sub> 39.79 ± 0.47 μM on A549 cell and <strong>1</strong> had IC<sub>50</sub> > 100 μM against all cells used. The antibacterial activity was also assayed and moupinamide (<strong>2</strong>) had significant activity against <em>Mycobacterium smegmatis</em> (MIC = 9.7 μg/mL) while other samples possessed mostly weak and moderate activities. To the best of our knowledge, this study is the first isolation of ceramide from the <em>Crinum</em> genus, providing new insights into the chemodiversity of this genus. Moreover, new data concerning the pharmacological properties of <em>C. ornatum</em> (L.f.) Herb. and its chemophenetic significance in the genus <em>Crinum</em> and the Amaryllidaceae family were revealed.</div></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"121 ","pages":"Article 104991"},"PeriodicalIF":1.4000,"publicationDate":"2025-03-03","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/S0305197825000407","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}
引用次数: 0
Abstract
A previously undescribed ceramide, crinceramide (1), along with nineteen known compounds (2–20) were isolated from Crinum ornatum (L.f.) Herb. using column chromatography techniques over silica gel and Sephadex LH-20. The structure of the new compound was established by different spectroscopic methods including 1D and 2D-NMR, HRESI-MS and chemical conversions. The extract and fractions had strong activities on three human cancer cells (lung A549, breast MCF7, and cervical HeLa) with IC50 from <0.63 to 9.76 μg/mL whereas compounds displayed IC50 ranging from 39.79 to > 100 μM. Moupinamide (2) was the most active with IC50 39.79 ± 0.47 μM on A549 cell and 1 had IC50 > 100 μM against all cells used. The antibacterial activity was also assayed and moupinamide (2) had significant activity against Mycobacterium smegmatis (MIC = 9.7 μg/mL) while other samples possessed mostly weak and moderate activities. To the best of our knowledge, this study is the first isolation of ceramide from the Crinum genus, providing new insights into the chemodiversity of this genus. Moreover, new data concerning the pharmacological properties of C. ornatum (L.f.) Herb. and its chemophenetic significance in the genus Crinum and the Amaryllidaceae family were revealed.
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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