Decomposition reaction of sesamin in supercritical water.
The methylenedioxyphenyl moiety in the structure of sesamin and episesamin was changed into the catechol moieties, (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane, (1R,2R,5R,6S)-2-(3,4-dihydroxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane, (1R,2R,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane, (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0]octane, and (1R,2R,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0]octane, in supercritical water. These products had same structures as the sesamin metabolites which act as antioxidants in the liver. These features suggested the direct preparation of antioxidants from sesamin by a one-step reaction using supercritical water.
Nakai
Masaaki
M
Suntory Research Center, Suntory Ltd, Osaka, Japan. Masaaki_Nakai@suntory.co.jp
Kageyama
Norihiko
N
Nakahara
Koichi
K
Miki
Wataru
W
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid; D004149:Dioxoles / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification*; D006358:Hot Temperature; D017705:Lignans / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000975:Antioxidants; D004149:Dioxoles; D016166:Free Radical Scavengers; D017705:Lignans; D014867:Water; C054125:sesamin