trans-Beta-Apo-8'-carotenal
beta-Apo-8'-carotenal, canthaxanthin and astaxanthin, are inducers of CYP1A1 and 1A2 in the rat. These carotenoids form a new class of inducers of CYP1A, structurally very different from the classical inducers as 3-methylcholanthrene, beta-naphtoflavone or dioxin.
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Xenobiotica, 1996, 26(9):909-919.
beta-Apo-8'-carotenal, but not beta-carotene, is a strong inducer of liver cytochromes P4501A1 and 1A2 in rat.[Pubmed:
8893038]
METHODS AND RESULTS:
1. The catalytic activities of several phase I and II xenobiotic-metabolizing enzymes and their immunochemical detection have been investigated in liver microsomes and cytosol of the male rat, which had been fed for 15 days with diets containing 300 mg/kg beta-carotene isomers (all-trans beta-carotene or beta-carotene from Dunaliella salina rich in 9-cis isomer or isomerized beta-carotene), or apocarotenoids as beta-apo-8'-carotenal, ethyl beta-apo-8'-carotenoate and citranaxanthin. 2. Beta-carotene, either all-trans or containing cis isomers, did not induce any significant change in the measured activities. By contrast, beta-apo-8'-carotenal increased the liver content of cytochrome P450, the activity of NADH- and NADPH-cytochrome c reductase, and strongly increased some cytochrome P450-dependent activities, particularly ethoxyresorufin O-deethylase (x158), methoxyresorufin O-demethylase (x22), pentoxy- and benzoxyresorufin O-dealkylases, but did not affect erythromycin N-demethylase nor nitrosodimethylamine N-demethylase activities. Phase II p-nitrophenol- and 4-hydroxy- biphenyl-uridine diphosphoglucuronosyl transferase activities were also increased by beta-apo-8'carotenal. Western blots of microsomal proteins clearly showed the induction of CYP1A1 and 1A2 by beta-apo-8'-carotenal. This induction profile resembles that produced by two other carotenoids: canthaxanthin and astaxanthin. Ethyl beta-apo-8'-carotenoate and citranaxanthin showed similar effects to beta-apo-8'-carotenal but of less intensity.
CONCLUSIONS:
3. Three carotenoids: beta-apo-8'-carotenal, canthaxanthin and astaxanthin, are inducers of CYP1A1 and 1A2 in the rat. These carotenoids form a new class of inducers of CYP1A, structurally very different from the classical inducers as 3-methylcholanthrene, beta-naphtoflavone or dioxin.
Proc Spie, 1995, 2362:231-239.
Photoconductivity of all trans-beta-carotene and all-trans-beta-apo-8'-carotenal crystals.[Reference:
WebLink]
METHODS AND RESULTS:
Three different kinds of condensed samples of all-trans-(beta) -carotene, i.e., a spin-coated film, a cast film, and crystals, were prepared. Excitation spectra of photoconductivity at room temperature and resonance Raman scattering at 11 K were obtained for these samples, and the influence of oxygen to these excitation spectra were examined. In the near infrared region below the lowest allowed transition to the electronically excited 1Bu state, clear bands were observed in those two kinds of excitation spectra and were characteristic of the crystals as well as the cast film. The excitation bands are attributable to the same transition to the 21Ag molecular exciton state. A similar series of experiments were carried out for
all-trans-Beta-Apo-8'-carotenal .
CONCLUSIONS:
The results support the above assignment for all-trans- (beta) -carotene.
