New products in the hepoxilin pathway: isolation of 11-glutathionyl hepoxilin A3 through reaction of hepoxilin A3 with glutathione S-transferase.
We describe herein the metabolism of hepoxilin A3 (HxA3) by glutathione S-transferase (GST) into a glutathione conjugate. The reaction was carried out with HxA3 (unlabelled and 14C-labelled) and glutathione (unlabelled and tritium labelled). When two isomers of HxA3 were reacted with GST, two products were formed. Only one product was formed when a single isomer of HxA3 was used. The isomeric product HxB3 was marginally active indicating considerable specificity in the reaction with GST. The products were characterized by retention of tritium from glutathione and by comparison of their migration on high performance liquid chromatography with authentic reference compounds. The products bear the structure, 11-glutathionyl HxA3.
Pace-Asciak
C R
CR
Research Institute, Hospital for Sick Children, Toronto, Ontario, Canada.
Laneuville
O
O
Chang
M
M
Reddy
C C
CC
Su
W G
WG
Corey
E J
EJ
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives / Q000096:biosynthesis* / Q000302:isolation & purification / Q000378:metabolism*; D001711:Biotransformation; D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis* / Q000378:metabolism*; D005982:Glutathione Transferase / Q000378:metabolism*; D007527:Isoenzymes / Q000378:metabolism; D011865:Radioisotope Dilution Technique
D002250:Carbon Radioisotopes; D005231:Fatty Acids, Unsaturated; D007527:Isoenzymes; C061163:11-glutathionylhepoxilin A3; C038243:8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid; D005982:Glutathione Transferase; D015126:8,11,14-Eicosatrienoic Acid