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Title: Microbial metabolism part 13 metabolites of hesperetin

item HERATH, WIMAL - University Of Mississippi
item KHAN, IKHLAS - University Of Mississippi

Submitted to: Chemical and Pharmaceutical Bulletin
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/29/2011
Publication Date: 8/9/2011
Citation: Herath, W., Khan, I.A. 2011. Microbial metabolism part 13 metabolites of hesperetin. Chemical and Pharmaceutical Bulletin. p. 5784-5786.

Interpretive Summary: Hesperetin, a flavonoid found in sweet orange and lemon as rhamnoglucoside (hesperidin) is shown to have important biological activities. Studies show that hespertin is metabolized into glucuronides and sulfonates in mammalian systems. The present work involving the microbial transformation of hesperitin to yield hesperetin 7-sulfate and eriodictyol 4'-O-a-qinovopyranoside as prominent metabolites, indicates the ability of microbes to mimic mammalian metabolism. In addition to the isolation of the above metabolites we were able to obtain Eriodictyol and 8-hydroxyhesperitin with antioxidant properties much higher than those of hesperitin. This may be of help to evaluate the activity of hesperitin in terms of these metabolites not detected in previous experiments. The metabolites formed during microbial transformation studies were in sufficient quantities for determining chemical structures as well as for evaluating their biological properties.

Technical Abstract: The fungal culture, Mucor ramannianus (ATCC 2628) transformed hesperitin to four metabolites: 4'-methoxy -5, 7, 8, 3'-tetrahydroxyflavanone (8-hydroxyhesperetin), 5, 7, 3', 4'-tetrahydroxyflavanone (eriodictyol), 4'-methoxy-5, 3'-dihydroxyflavanone 7-sulfate (hesperetin 7-sulfate) and 5, 7, 3'-trihydroxyflavanone 4'-O-a-quinovopyranoside (eriodictyol 4'-O-a- quinovopyranoside). The structures were established by spectroscopic methods.