Antimutagens from Momordica charantia.
The antimutagenic principle of the green fruits of Momordica charantia was shown by the micronucleus test to be an intractable mixture of novel acylglucosylsterols. The antimutagens were extracted from the green fruits with ethanol and isolated from the bioactive petroleum ether and carbon tetrachloride extracts by repeated and sequential flash column chromatography. The major component of the mixture is 3-O-[6'-O-palmitoyl-beta-D-glucosyl-stigmasta-5,25(27)-dien and the minor component is the stearyl derivative (Guevara, 1989). At a dosage range in mice of 50-12.5 micrograms extract/g, the mixture reduced by about 80% the number of micronucleated polychromatic erythrocytes induced by the well-known mutagen mitomycin C. Structure-activity correlation studies suggested that the antimutagenic activity may reside in the peculiar lipid-like structure of the acylglucosylsterols. Ingestion of these compounds may result in their absorption in the plasma membrane lipid bilayer which could adversely affect the membrane permeability towards mitomycin C and disrupt the cellular activity of the latter.
Guevara
A P
AP
Institute of Chemistry, University of the Philippines, Quezon City.
Lim-Sylianco
C
C
Dayrit
F
F
Finch
P
P
D000818:Animals; D000431:Ethanol; D005960:Glucosides / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000494:pharmacology*; D051379:Mice; D015162:Micronucleus Tests; D016685:Mitomycin; D008937:Mitomycins / Q000494:pharmacology; D015394:Molecular Structure; D009154:Mutation; D010840:Phytosterols / Q000494:pharmacology*; D010936:Plant Extracts / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000032:analysis*; D013265:Stigmasterol / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology*
D005960:Glucosides; D006027:Glycosides; D008937:Mitomycins; D010840:Phytosterols; D010936:Plant Extracts; C065015:3-O-(6'-O-palmitoylglucosyl)stigmasta-5,25(27)-diene; C065016:3-O-(6'-O-stearoylglucosyl)stigmasta-5,25(27)-diene; D000431:Ethanol; D016685:Mitomycin; D013265:Stigmasterol