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. 2006 Jun;3(2):185-90.
doi: 10.3390/ijerph2006030021.

Photoirradiation of retinyl palmitate in ethanol with ultraviolet light--formation of photodecomposition products, reactive oxygen species, and lipid peroxides

Qingsu Xia  1 , Jun J Yin, Wayne G Wamer, Shu-Hui Cherng, Mary D Boudreau, Paul C Howard, Hongtao Yu, Peter P Fu
Affiliations

Photoirradiation of retinyl palmitate in ethanol with ultraviolet light--formation of photodecomposition products, reactive oxygen species, and lipid peroxides

Qingsu Xia et al. Int J Environ Res Public Health. 2006 Jun.

Abstract

We have previously reported that photoirradiation of retinyl palmitate (RP), a storage and ester form of vitamin A (retinol), with UVA light resulted in the formation of photodecomposition products, generation of reactive oxygen species, and induction of lipid peroxidation. In this paper, we report our results following the photoirradiation of RP in ethanol by an UV lamp with approximately equal UVA and UVB light. The photodecomposition products were separated by reversed-phase HPLC and characterized spectroscopically by comparison with authentic standards. The identified products include: 4-keto-RP, 11-ethoxy-12-hydroxy-RP, 13-ethoxy-14-hydroxy-RP, anhydroretinol (AR), and trans- and cis-15-ethoxy-AR. Photoirradiation of RP in the presence of a lipid, methyl linoleate, resulted in induction of lipid peroxidation. Lipid peroxidation was inhibited when sodium azide was present during photoirradiation which suggests free radicals were formed. Our results demonstrate that, similar to irradiation with UVA light, RP can act as a photosensitizer leading to free radical formation and induction of lipid peroxidation following irradiation with UVB light.

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Figures

Figure 1
Figure 1
Structures, names, abbreviations, and numbering of retinol, retinyl palmitate (RP), and anhydroretinol (AR).
Figure 2
Figure 2
The light wavelength distribution of the (A) UVA and (B) UVB light sources
Figure 3
Figure 3
Reversed-phase HPLC profile of the photodecomposition products of RP (0.5% in ethanol) after irradiation with 14 J/cm2 of (A) UVA or (B) UVB light. HPLC analysis was conducted on a Prodigy 5 μ ODS column (4.6 × 250 mm) eluted isocratically with methylene chloride in methanol (1/9; v/v) at 1 mL/min.
Figure 4
Figure 4
UV-visible absorption spectra of RP (--------), 4-keto-RP (–·–·–·–), and anhydroretinol (AR) (———).
Figure 5
Figure 5
Reversed-phase HPLC profile and UV-visible absorption spectra of RP photodecomposition products identified as all-trans-AR (AR) and cis-ARs (6Z-, 8Z-, and 12Z-AR). HPLC analysis was conducted on a Vydac C18 column (4.6 × 250 mm) eluted isocratically with water in methanol (14/86; v/v) at 1 mL/min.
Figure 6
Figure 6
Lipid peroxidation induced by photoirradiation of RP with UVB light, and inhibitory effect of NaN3 on the peroxidation of methyl linoleate. The levels of peroxidation were measured by HPLC analysis in which the eluate was monitored at 235 nm.
Figure 7
Figure 7
The proposed mechanistic pathways initiated by photoirradiation of RP with UVB light leading to generation of RP photodecomposition products, ROS, lipid peroxidation, and DNA damage.
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References

    1. (IARC) International Agency for Research on Cancer. Handbooks of Cancer Prevention: Vitamin A. Vol. 3 Lyon, France: 1998.
    1. Tee E. S. Carotenoids and retinoids in human nutrition. Crit. Rev. Food Sci. Nutr. 1992;31:103–163. - PubMed
    1. Idson B. Vitamins in cosmetics, an update I. Overview and Vitamin A. Drug Cosmet. Ind. 1990;146:26–91.

    1. Data from the U.S. Food and Drug Administration’s Voluntary Cosmetics Registration Program, 2004

    1. Fu P. P., Howard P. C., Culp S., Xia Q., Webb P. J., Blankenship L., Wamer W. G., Bucher J. R. Do topically applied skin creams containing retinyl palmitate affect the photocarcinogenicity of simulated solar light? J. Food Drug Anal. 2002;10:262–268.

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