Enzymatic formation of 9-cis, 13-cis, and all-trans retinals from isomers of beta-carotene.
9-cis Retinoic acid is a highly preferred ligand for the nuclear retinoic acid receptor RXR. Although 9-cis retinoic acid can be formed from all-trans retinoic acid in vivo and in vitro, the nature of the isomerization process has not been defined. 9-cis-Retinoic acid might also be formed biologically from 9-cis beta-carotene, an isomer of beta-carotene commonly found in foods. We have observed that enzyme preparations of rat liver and intestine convert highly purified 9-cis beta-carotene (99.8%) to a mixture of 9-cis, all-trans, and 13-cis retinals. Highly purified all-trans beta-carotene (99.7%) and 13-cis beta-carotene (99%) are primarily converted to all-trans retinal. Several aldehyde dehydrogenases in tissues can convert retinal to retinoic acid. Although the rates of cleavage of 9-cis and 13-cis beta-carotenes are slower than that of the all-trans isomer, the oxidative conversion of 9-cis beta-carotene to 9-cis and all-trans retinals is the first identified enzymatic reaction for the formation of 9-cis retinal in animal tissues.
Nagao
A
A
Department of Biochemistry and Biophysics, Iowa State University, Ames 50011.
Olson
J A
JA
D000444:Aldehyde Dehydrogenase / Q000378:metabolism; D000818:Animals; D002338:Carotenoids / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004355:Drug Stability; D007422:Intestines / Q000201:enzymology; D007700:Kinetics; D008099:Liver / Q000201:enzymology; D008297:Male; D051381:Rats; D017207:Rats, Sprague-Dawley; D012172:Retinaldehyde / Q000737:chemistry / Q000378:metabolism*; D013053:Spectrophotometry; D013237:Stereoisomerism; D014212:Tretinoin / Q000737:chemistry / Q000378:metabolism; D019207:beta Carotene
D019207:beta Carotene; D002338:Carotenoids; D014212:Tretinoin; D000444:Aldehyde Dehydrogenase; D012172:Retinaldehyde