Synthesis of messagenin and platanic acid chalcone derivatives and their biological potential

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.

Automated summary

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.