First chemical synthesis of antioxidative metabolites of sesamin.
The first chemical synthesis of two metabolites ((1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-1) and (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-2)) of sesamin was achieved by a simple two-step approach from sesamin. The approach consists of acetoxylation of the methylenedioxy moiety(ies) with lead(IV) tetraacetate and acid hydrolysis of the resulting hemiorthoester to SC-1 and SC-2.
Urata
Hidehito
H
Osaka University of Pharmaceutical Sciences, Osaka, Japan. urata@gly.oups.ac.jp
Nishioka
Yuka
Y
Tobashi
Takafumi
T
Matsumura
Yasuo
Y
Tomimori
Namino
N
Ono
Yoshiko
Y
Kiso
Yoshinobu
Y
Wada
Shun-Ichi
S
D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004149:Dioxoles / Q000493:pharmacokinetics* / Q000494:pharmacology* / Q000652:urine; D006868:Hydrolysis; D007202:Indicators and Reagents; D017705:Lignans / Q000493:pharmacokinetics* / Q000494:pharmacology* / Q000652:urine; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D000975:Antioxidants; D004149:Dioxoles; D007202:Indicators and Reagents; D017705:Lignans; D009942:Organometallic Compounds; C029433:lead tetraacetate; C054125:sesamin