{"title":"Synthesis and evaluation of Calenduloside E against drug-resistant <i>Candida albicans</i>.","authors":"Fei Zou, Shan Yin, Yan-Dan Wu, Rui-Na Liu, Ni-Ni Zhan, Tian-Yu Zhang, Ze-Fei Fan, Bao-Jing Li, Rui-Rui Wang, Guang-Hui Ni","doi":"10.1080/10286020.2025.2471467","DOIUrl":null,"url":null,"abstract":"<p><p>Calenduloside E (CE), also known as a triterpenoid saponin, has demonstrated diverse biological activities. This paper investigates the chemical synthesis of CE, focusing on the key step of glucuronidation of oleanolic acid benzylate. Among trichloroacetimidate, bromide, and thioglucuronide as glucuronyl donors, trichloroacetimidate proved most effective, with scandium(III) trifluoromethanesulfonate identified as the optimal promoter. Notably, CE exhibited significant activity against fluconazole-resistant <i>C. albicans</i> (ATCC14053), with an MIC<sub>80</sub> of 5.5 µg/ml. Further mechanistic studies demonstrated that the combination of CE and FLC significantly inhibits the proliferation of <i>C. albicans</i> hyphae, biofilm formation, and cell membrane function.</p>","PeriodicalId":15180,"journal":{"name":"Journal of Asian Natural Products Research","volume":" ","pages":"1-17"},"PeriodicalIF":1.3000,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Asian Natural Products Research","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1080/10286020.2025.2471467","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
Calenduloside E (CE), also known as a triterpenoid saponin, has demonstrated diverse biological activities. This paper investigates the chemical synthesis of CE, focusing on the key step of glucuronidation of oleanolic acid benzylate. Among trichloroacetimidate, bromide, and thioglucuronide as glucuronyl donors, trichloroacetimidate proved most effective, with scandium(III) trifluoromethanesulfonate identified as the optimal promoter. Notably, CE exhibited significant activity against fluconazole-resistant C. albicans (ATCC14053), with an MIC80 of 5.5 µg/ml. Further mechanistic studies demonstrated that the combination of CE and FLC significantly inhibits the proliferation of C. albicans hyphae, biofilm formation, and cell membrane function.
期刊介绍：
The Journal of Asian Natural Products Research (JANPR) publishes chemical and pharmaceutical studies in the English language in the field of natural product research on Asian ethnic medicine. The journal publishes work from scientists in Asian countries, e.g. China, Japan, Korea and India, including contributions from other countries concerning natural products of Asia. The journal is chemistry-orientated. Major fields covered are: isolation and structural elucidation of natural constituents (including those for non-medical uses), synthesis and transformation (including biosynthesis and biotransformation) of natural products, pharmacognosy, and allied topics. Biological evaluation of crude extracts are acceptable only as supporting data for pure isolates with well-characterized structures.
All published research articles in this journal have undergone rigorous peer review, based on initial editor screening and anonymized refereeing by at least two expert referees.
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