Duc Hung Nguyen , Antoine Bruguière , Tomofumi Miyamoto , Alexandre M.M. Dias , Pierre-Simon Bellaye , Betrand Collin , Marc Sautour , Loïc Briand , Anne-Claire Mitaine-Offer
{"title":"Steroidal glycosides from Yucca rostrata and Dracaena braunii and their cytotoxic and antimicrobial evaluation","authors":"Duc Hung Nguyen , Antoine Bruguière , Tomofumi Miyamoto , Alexandre M.M. Dias , Pierre-Simon Bellaye , Betrand Collin , Marc Sautour , Loïc Briand , Anne-Claire Mitaine-Offer","doi":"10.1016/j.bse.2024.104791","DOIUrl":null,"url":null,"abstract":"<div><p><span>Steroidal glycosides are known to possess a wide range of biological activities such as cytotoxicity and antimicrobial effects. To isolate more of these glycosides to get a better understanding at their structure/activity relationship, and to complete chemotaxonomic information, a cultivated </span><span><em>Yucca</em><em> rostrata</em></span> was studied, along with a wild and a cultivated <span><em>Dracaena</em><em> braunii</em></span><span><span>. Thirteen spiro- and furostan glycosides were isolated from those plants and their structure were elucidated using 1D and </span>2D NMR. Since they were already reported from other plant species, it allowed us to get an idea on which type of structure might be specific to which taxon. The compounds from </span><em>D. braunii</em><span> were tested for their antimicrobial activity against </span><span><em>Candida albicans</em><em>, C. glabrata</em></span> and <span><em>Staphylococcus aureus</em><em>.</em></span> Only compound <strong>12 (</strong>CAS 39491-39-9) showed a weak activity on <em>S. aureus</em> with a MIC of 50 μg/mL. The compounds from <em>Y. rostrata</em><span> were tested for their cytotoxicity against a CT26 (murine colorectal carcinoma) cell line. The spirostan glycosides </span><strong>4</strong> (CAS 119459-80-2) and <strong>5</strong> (CAS 164592-97-6) showed an interesting activity with an IC<sub>50</sub> of 2.38 μM and 2.26 μM, respectively. Comparing the structures of the active <em>versus</em> the inactive ones, we were able to formulate some hypotheses regarding the structure/activity relationships, in accordance with the current literature.</p></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-01-30","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/S0305197824000103","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
Steroidal glycosides are known to possess a wide range of biological activities such as cytotoxicity and antimicrobial effects. To isolate more of these glycosides to get a better understanding at their structure/activity relationship, and to complete chemotaxonomic information, a cultivated Yucca rostrata was studied, along with a wild and a cultivated Dracaena braunii. Thirteen spiro- and furostan glycosides were isolated from those plants and their structure were elucidated using 1D and 2D NMR. Since they were already reported from other plant species, it allowed us to get an idea on which type of structure might be specific to which taxon. The compounds from D. braunii were tested for their antimicrobial activity against Candida albicans, C. glabrata and Staphylococcus aureus. Only compound 12 (CAS 39491-39-9) showed a weak activity on S. aureus with a MIC of 50 μg/mL. The compounds from Y. rostrata were tested for their cytotoxicity against a CT26 (murine colorectal carcinoma) cell line. The spirostan glycosides 4 (CAS 119459-80-2) and 5 (CAS 164592-97-6) showed an interesting activity with an IC50 of 2.38 μM and 2.26 μM, respectively. Comparing the structures of the active versus the inactive ones, we were able to formulate some hypotheses regarding the structure/activity relationships, in accordance with the current literature.
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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