AI Article Synopsis
- Betulinic acid’s low solubility limits its use as an anticancer treatment, prompting researchers to modify it and similar compounds with sugar molecules.
- Synthesis of glycosides led to varying levels of cytotoxicity; adding sugars to betulin reduced its effectiveness, while modifying lupeol significantly increased its potency against cancer cells.
- The study found that the 3-O-alpha-L-rhamnopyranoside form of betulinic acid was particularly effective, making cancer cells much more sensitive than healthy cells, suggesting glycosylated triterpenoids could be promising cancer treatments.
Article Abstract
The weak hydrosolubility of betulinic acid (3) hampers the clinical development of this natural anticancer agent. In order to circumvent this problem and to enhance the pharmacological properties of betulinic acid (3) and the lupane-type triterpenes lupeol (1), betulin (2), and methyl betulinate (7), glycosides (beta-D-glucosides, alpha-L-rhamnosides, and alpha-D-arabinosides) were synthesized and in vitro tested for cytotoxicity against three cancerous (A-549, DLD-1, and B16-F1) and one healthy (WS1) cell lines. The addition of a sugar moiety at the C-3 or C-28 position of betulin (2) resulted in a loss of cytotoxicity. In contrast, the 3-O-beta-D-glucosidation of lupeol (1) improved the activity by 7- to 12-fold (IC50 14-15.0 microM). Moreover, the results showed that cancer cell lines are 8- to 12-fold more sensitive to the 3-O-alpha-L-rhamnopyranoside derivative of betulinic acid (IC50 2.6-3.9 microM, 22) than the healthy cells (IC50 31 microM). Thus, this study indicates that 3-O-glycosides of lupane-type triterpenoids represent an interesting class of potent in vitro cytotoxic agents.
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| http://dx.doi.org/10.1016/j.bmc.2006.05.075 | DOI Listing |
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