Novel Antioxidative Metabolites in Rat Liver with Ingested Sesamin

Sesamin, a major lignan in sesame oil, is known to have many biological activities, especially protective effects against oxidative damage in the liver. As sesamin itself has no antioxidative properties in vitro, to elucidate the mechanism of its antioxidative effects, the reaction products of sesam...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2003-03, Vol.51 (6), p.1666-1670
Main Authors: Nakai, Masaaki, Harada, Masami, Nakahara, Koichi, Akimoto, Kengo, Shibata, Hiroshi, Miki, Wataru, Kiso, Yoshinobu
Format: Article
Language:English
Subjects:
Animals
antioxidant activity
Antioxidants - analysis
Antioxidants - metabolism
Antioxidants - pharmacology
Bile - chemistry
Biological and medical sciences
Biphenyl Compounds
catechol
Chromatography, High Pressure Liquid
Dioxoles - metabolism
free radical scavengers
Free Radical Scavengers - chemistry
General pharmacology
glucuronic acid
Hydroxyl Radical - chemistry
Lignans - metabolism
Lipid Peroxidation - drug effects
liver
Liver - metabolism
Magnetic Resonance Spectroscopy
Male
Medical sciences
metabolites
oral administration
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Picrates - chemistry
Rats
Rats, Wistar
sesame oil
Spectrometry, Mass, Electrospray Ionization
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Summary:Sesamin, a major lignan in sesame oil, is known to have many biological activities, especially protective effects against oxidative damage in the liver. As sesamin itself has no antioxidative properties in vitro, to elucidate the mechanism of its antioxidative effects, the reaction products of sesamin in rat liver homogenate were analyzed. The methylenedioxyphenyl moiety in the structure of sesamin was shown to be changed into a dihydrophenyl (catechol) moiety. The enzymatic reaction products in vitro were identified as (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane and (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0]octane, which showed strong radical scavenging activities; the latter was a novel compound. The same metabolites were found as glucuronic acid and/or sulfic acid conjugates in substantial amounts in rat bile after oral administration of sesamin. It is suggested that sesamin is a prodrug and the metabolites containing the catechol moieties in their structures are responsible for the protective effects of sesamin against oxidative damage in the liver. Keywords: Sesamin; antioxidant; metabolite
ISSN:0021-8561
1520-5118
DOI:10.1021/jf0258961