Reaction products of gamma-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile.
gamma-Tocopherol was reacted with (E)-4-oxo-2-nonenal (ONE) at 37 degrees C in an acidic acetonitrile solution. The reaction products were isolated by reversed-phase high-performance liquid chromatography and their structures were characterized to be 5-substituted gamma-tocopherols: 5-(1-(furan-2-yl)pentyl)-gamma-tocopherol (1), 3-(1-butyl-4,5,7-trimethyl-7-(4,8,12-trimethyltridecyl)-8,9-dihydro-7H-furo[3,2-f]chromen-2yl)propanal (2), and 1-(1-butyl-4,5,7-trimethyl-7-(4,8,12-trimethyltridecyl)-8,9-dihydro-7H-furo[3,2-f]chromen-2-yl)-4-(furan-2-yl)octan-3-one (3). Compound 1 was the predominant product under the mild acidic conditions, whereas compounds 2 and 3 were relatively stable and accumulated during the reaction. Compound 1 was detected as the product when gamma-tocopherol and ONE were incubated in methyl linoleate in the presence of dicetyl phosphate. The results indicate that gamma-tocopherol may trap ONE under acidic conditions of lipid peroxidation.
Saito
Fumie
F
The United Graduate School of Agricultural Science, Gifu University, Japan.
Iwamoto
Satoshi
S
Yamauchi
Ryo
R
D000097:Acetonitriles / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005663:Furans / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008041:Linoleic Acids / Q000737:chemistry; D013237:Stereoisomerism; D024504:gamma-Tocopherol / Q000737:chemistry*
C403894:4-oxo-2-nonenal; D000097:Acetonitriles; D000447:Aldehydes; D005663:Furans; D008041:Linoleic Acids; C005575:methyl linoleate; D024504:gamma-Tocopherol; C039281:furan; C032159:acetonitrile