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Simple chemical syntheses of TAG monohydroperoxides
Author(s) -
Hui ShuPing,
Murai Tsuyoshi,
Yoshimura Teruki,
Chiba Hitoshi,
Kurosawa Takao
Publication year - 2003
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-003-1191-9
Subject(s) - structural isomer , chemistry , chromatography , high performance liquid chromatography , triolein , organic chemistry , enzyme , lipase
Abstract For the purpose of synthesizing standards to be used in the quantification of TAG hydroperoxides, three TAG (1,2‐dioleoyl‐3‐palmitoylglycerol, 1‐oleoyl‐2‐linoleoyl‐3‐palmitoylglycerol, and triolein) monohydroperoxides were chemically synthesized as authentic specimens. TAG were prepared by using a simple condensation in pyridine of glycerol and the corresponding acid chlorides. These TAG were then converted into monohydroperoxides by a photosensitized peroxidation. The synthesized monohydroperoxides were analyzed by normal‐phase and RP‐HPLC. The results of normal‐phase HPLC analysis showed that monohydroperoxides from a corresponding TAG were a mixture of regioisomers. In RP‐HPLC, however, the regioisomers of monohydroperoxides were not separated and gave a single peak, which may improve the sensitivity for the detection of TAG monohydroperoxides. In this study TAG monohydroperoxide standards were synthesized; these will be useful for the study of yet unknown biological and pathological roles of TAG hydroperoxides.