A new ceramide and other constituents from Crinum ornatum (L.f.) Herb. (Amaryllidaceae) and their chemophenetic significance

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Biochemical Systematics and Ecology Pub Date : 2025-08-01 Epub Date: 2025-03-03 DOI:10.1016/j.bse.2025.104991

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

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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.

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一种新神经酰胺及其它成分的研究赫伯特。（Amaryllidaceae）及其化学化学意义

一种先前未被描述的神经酰胺，criinceramide(1)，以及19种已知化合物（2-20）从criinum ornatum （L.f）中分离出来。赫伯特。在硅胶和Sephadex LH-20上使用柱层析技术。通过不同的光谱方法，包括1D和2D-NMR， HRESI-MS和化学转换，确定了新化合物的结构。提取物及其组分对肺癌细胞A549、乳腺癌细胞MCF7和宫颈癌细胞HeLa具有较强的抑制活性，IC50值为0.63 ~ 9.76 μg/mL，而化合物的IC50值为39.79 ~ 9.76 μg/mL；100μM。其中，Moupinamide(2)对A549细胞的IC50为39.79±0.47 μM，活性最高；100 μM对所有使用的细胞。结果表明，moupinamide(2)对耻垢分枝杆菌的抑菌活性显著（MIC = 9.7 μg/mL），而其他样品的抑菌活性大多为弱和中等。据我们所知，这项研究是第一次从crium属中分离神经酰胺，为该属的化学多样性提供了新的见解。此外，还获得了有关花楸药理特性的新资料。赫伯特。揭示了其在朱红色属和朱红色科植物中的化学遗传学意义。

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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.