An improved method to obtain naringin, a bitter flavored flavanone glicoside with proven biological activities, from grapefruit (Citrus x paradisi L.) peel waste is described. The proposed modification of the known process, which involves extraction with methanol and crystallization in water with the addition of dichloromethane, requires shorter processing time and reduced solvent volume. Due to the direct method employed, which did not require the 3-day air-drying stage, the hot extraction of fresh grapefruit albedo using methanol led to higher yields of naringin extract in half the time required. To evaluate the obtained naringin which possessed a wide range of pharmacological properties, it was subjected to chemical transformation into the flavone apigenin, an expensive and naturally-occurring flavonoid obtained in low yields.
Natural steroids and triterpenes such as β-sitosterol, stigmasterol, lupeol, ursolic and betulinic acids were transformed into its hexanoic and oleic esters, to evaluate the influence of chemical modification towards the cytotoxic activities against tumor cells. The derivatives were evaluated against five tumor cell lines [OVCAR-8 (ovarian carcinoma); SF-295 (glioblastoma); HCT-116 (colon adenocarcinoma); HL-60 (leukemia); and PC-3 (prostate carcinoma)] and the results showed only betulinic acid hexyl ester exhibits cytotoxic potential activity.
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