期刊
NATURAL PRODUCT RESEARCH
卷 36, 期 20, 页码 5189-5198出版社
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786419.2021.1922904
关键词
Alpha-glucosidase; anticancer; antiviral; betulin; betulonic acid; chalcone; Claisen‒ Schmidt reaction; messagenin; platanic acid
资金
- Wellcome Trust (UK)
- University of Queensland (Australia)
- Federal funds from the National Institutes of Allergy and Infectious Diseases, National Institutes of Health, Department of Health and Human Services [HHSN272201100016I]
Chalcone derivatives of 20-oxo-lupanes were synthesized and screened for biological activity, showing potential cytotoxic effects on cancer cell lines. The E configuration of one derivative was confirmed via X-ray analysis. Additionally, some compounds demonstrated inhibitory activity against enzymes and potential antiviral effects.
The chalcone derivatives of 20-oxo-lupanes have been synthesised and screened for some types of biological activity. Ozonolysis of lupanes afforded 20-oxo-derivatives with the following condensation using different aromatic aldehydes by Claisen-Schmidt reaction to the target compounds. The E configuration of 19-[3-(pyridin-3-yl)-prop-2-en-1-one]-fragment was established by X-ray analysis. Screening of cytotoxic activity against NCI-60 cancer cell line panel revealed, that messagenin derivative 9 has the highest activity with GI(50) value ranged from 0.304 to 0.804 mu M. A colorimetric SRB assay revealed for the 2,30-bis-furfurylidene derivative 11 and 30-bromo-20-oxo-29-nor-3,28-diacetoxy-betulin 16 cytotoxic activity against breast carcinoma MCF-7 and ovarian carcinoma A2780 cell lines. Compounds 11 and 13 acted also as inhibitors of the enzyme alpha-glucosidase (from S. saccharomyces) with IC50 values of 1.76 mu M and 3.3 mu M thus being 97- and 52-fold more active than standard acarbose. Antiviral potency of compounds 12 and 14 against HCMV, HSV-1 and HPV is also discussed.
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