Singlet molecular oxygen-quenching activity of carotenoids: Relevance to protection of the skin from photoaging

Journal of Clinical Biochemistry and Nutrition

Volumn 48, Issue 1, 2011, Pages 57-62

  Terao, Junji ^a   Minami, Yuko ^a   Bando, Noriko ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Carotenoids; Cholesterol hydroperoxide; Matrix metalloproteinase; Photoaging; Singlet molecular oxygen

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; BETA CAROTENE; CAROTENOID; CHOLESTEROL; CHOLESTEROL 5ALPHA HYDROPEROXIDE; COPROPORPHYRIN; GELATINASE B; HYDROPEROXIDE; LYCOPENE; OXYGEN; SKIN LIPID; UNCLASSIFIED DRUG; XANTHOPHYLL;

ANTIOXIDANT ACTIVITY; DIET SUPPLEMENTATION; DRUG ABSORPTION; DRUG ACCUMULATION; DRUG EFFICACY; DRUG METABOLISM; ERYTHEMA; HAIRLESS MOUSE; HUMAN; IN VIVO STUDY; LIPID PEROXIDATION; LIPID RAFT; LIPID STORAGE; LOW DRUG DOSE; MOLECULAR MODEL; NONHUMAN; OXIDATIVE STRESS; OXYGENATION; PHAGOCYTOSIS; PHOTOAGING; PHOTODYNAMICS; PHOTOOXIDATION; PROTEIN EXPRESSION; RADIATION EXPOSURE; REVIEW; SKIN; SKIN PROTECTION; ULTRAVIOLET A RADIATION; WRINKLE;

MUS;

EID: 78650737833     PISSN: 09120009     EISSN: None     Source Type: Journal    
DOI: 10.3164/jcbn.11-008FR     Document Type: Review

References (54)

1. Krinsky NI. The antioxidant and biological properties of the carotenoids. Ann N Y Acad Sci 1998; 854: 443-447.
2. Niki E, Yoshida Y, Saito Y, Noguchi N. Lipid peroxidation: mechanism, inhibition, and biological effects. Biochem Biophys Res Commun 2005; 338: 668-676. (Pubitemid 41540614)
3. Burton GW, Ingold KU. β-Carotene: an unusual type of lipid antioxidant. Science 1984; 224: 569-573.
4. Lim BP, Nagao A, Terao J, Tanaka K, Suzuki T, Takama K. Antioxidant activity of xanthophylls on peroxyl radical-mediated phospholipid peroxidation. Biochim Biphys Acta 1992; 1126: 178-184.
5. Tsuchihashi H, Kigoshi M, Iwatsuki M, Niki E. Action of beta-carotene as an antioxidant against lipid peroxidation. Arch Biochem Biophys 1995; 323: 137-147.
6. Foote CS, Chang YC, Denny RW. Chemistry of singlet oxygen. X. Carotenoid quenching parallels biological protection. J Am Chem Soc 1970; 92: 5216-5218.
7. Di Mascio P, Kaiser S, Sies H. Lycopene as the most efficient biological carotenoid singlet oxygen quencher. Arch Biochem Biophys 1989; 274: 532-538. (Pubitemid 19261144)
8. Ouchi A, Aizawa K, Iwasaki Y, and et al. Kinetic study of the quenching reaction of singlet oxygen by carotenoids and food extracts in solution. Development of a singlet oxygen absorption capacity (SOAC) assay method. J Agric food Chem 2010; 58: 9967-9978.
9. 2-chloride system. FEBS Lett 1999; 443: 154-158.
10. Baier J, Maisch T, Maier M, Engel E, Landthaler M, Bäumler W. Singlet oxygen generation by UVA light exposure of endogeneous photosensitizer. Biophys J 2006; 91: 1452-1459. (Pubitemid 44174262)
11. Cadenas E, Sies H. Low-level chemiluminescence as an indicator of singlet molecular oxygen in biological systems. Methods Enzymol 1984; 105: 221-231. (Pubitemid 14165384)
12. Miyamoto S, Ronsein GE, Prado FM, and et al. Biological hydroperoxides and singlet molecular oxygen generation. IUBMB Life 2007; 59: 322-331. (Pubitemid 46763765)
13. Fuchs J. Potentials and limitations of the natural antioxidants RRR-alpha-tocopherol, L-ascorbic acid and β-carotene in cutaneous photoprotection. Free Radic Biol Med 1998; 25: 848-873.
14. Boelsma E, Hendriks HF, Roza L. Nutritional skin care: health effects of micronutrients and fatty acids. Am J Clin Nutr 2001; 73: 853-864. (Pubitemid 32405980)
15. Bruls WA, van Weedlden H, van der Leun JC. Transmission of UV-radiation through human epidermal layers as a factor influencing the minimal erythema dose. Photochem Photobiol 1984; 39: 63-67.
16. Krutmann J. Ultraviolet A radiation-induced biological effects in human skin: relevance for photoaging and photodermatosis. J Dermatol Sci 2000; 23 Suppl 1: S22-S26. (Pubitemid 30182546)
17. Arakane K, Ryu A, Hayashi C, and et al. Singlet oxygen (1 delta g) generation from coproporphyrin in propionibacterium acnes on irradiation. Biochem Biophys Res Commun 1996; 223: 578-582. (Pubitemid 26246115)
18. Wondrak GT, Roberts MJ, Cervantes-Laurean D, Jacobson MK, Jacobson EL. Proteins of the extracellular matrix are sensitizers of photo-oxidative stress in human skin cells. J Invest Dermatol 2003; 121: 578-586. (Pubitemid 37072271)
19. Wondrak GT, Roberts MJ, Jacobson MK, Jacobson EL. 3-hydroxypyridine chromophores are endogeneous sensitizers of photooxidative stress in human skin cells. J Biol Chem 2004; 279: 30009-30020.
20. Vever-Bizet C, Dellinger M, Brault D, Rougee M, Bensasson RV. Singlet molecular oxygen quenching by saturated and unsaturated fatty-acids and by cholesterol. Photochem Photobiol 1989; 50: 321-325.
21. Girotti AW, Korytowski W. Cholesterol as a singlet oxygen detector in biological systems. Methods Enzymol 2000; 319: 85-100. (Pubitemid 30448033)
22. Yamazaki S, Ozawa N, Hiratsuka A, Watanabe T. Quantitative determination of cholesterol 5α, 7α, and 7β-hydroperoxides in rat skin. Free Radic Biol Med 1999; 27: 110-118. (Pubitemid 29353091)
23. Kligman LH. The hairless mouse model for photoaging. Clin Dermatol 1996; 14: 183-195.
24. Minami Y, Yokoi S, Setoyama M, and et al. Combination of TLC blotting and gas chromatography-mass spectrometry for analysis of peroxidized cholesterol. Lipids 2007; 42: 1055-1063. (Pubitemid 350127319)
25. Brinkhorst J, Nara SJ, Pratt DA. Hock cleavage of cholesterol 5α- hydroperoxide: an ozone-free pathway to the cholesterol ozonolysis products identified in arterial plaque and brain tissue. J Am Chem Soc 2008; 130: 12224-12225.
26. Zhang Q, Powers ET, Nieva J, and et al. Metabolite-initiated protein misfolding may trigger Alzheimer's disease. Proc Natl Acad Sci USA 2004; 101: 4752-4757.
27. Takuchi C, Galvé R, Nieva J, and et al. Proatherogenic effects of the cholesterol ozonolysis products, atheronal-A and atheronal-B. Biochemistry 2006; 45: 7162-7170.
28. Usui K, Hulleman JD, Paulsson JF, Siegel SJ, Powers ET, Kelly JW. Site-specific modification of Alzheimer's peptides by cholesterol oxidation products enhances aggregation energetics and neurotoxicity. Proc Natl Acad Sci USA 2009; 106: 18563-18568.
29. Oku H, Shudo J, Mimura K, Haratake A, Nagata J, Chinen I. 1-O-Alkyl-2,3-diacylglycerols in the skin surface lipids of the hairless mouse. Lipids 1995; 30: 169-172.
30. Oku H, Shudo J, Mimura K, Haratake A, Nagata J, Chinen I. Age-related changes in branched-chain fatty acid concentration of the skin surface lipid from hairless mouse. Comp Biochem Physiol B Biochem Mol Biol 1996; 114: 103-106.
31. Bando N, Hayashi H, Wakamatsu S, and et al. Participation of singlet oxygen in ultraviolet-A-induced lipid peroxidation in mouse skin and its inhibition by dietary β-carotene:an ex vivo study. Free Radic Biol Med 2004; 37: 1854-1863.
32. Minami Y, Yokoyama K, Bando N, Kawai Y, Terao J. Occurrence of singlet oxygen oxygenation of oleic acid and linoleic acid in the skin of live mice. Free Radic Res 2008; 42: 197-204.
33. Maharshak N, Shapiro J, Trau H. Carotenoderma-a review of the current literature. Int J Dermatol 2003; 42: 178-181.
34. Stahl W, Heinrich U, Jungmann H, and et al. Increased dermal carotenoid levels assessed by noninvasive reflection spectrophotometry correlate with serum levels in women ingesting Betatene. J Nutr 1998; 128: 903-907.
35. Nagao A. Absorption and function of dietary carotenoids. Forum Nutr 2009; 61: 55-63.
36. Nagao A. Oxidative conversion of carotenoids to retinoids and other products. J Nutr 2004; 134: 237S-240S.
37. von Lintig J, Hessel S, Isken A, and et al. Towards a better understanding of carotenoid metabolism in animals. Biochim Biophys Acta 2005; 1740: 122-131.
38. Sies H, Stahl W. Carotenoids and UV protection. Photochem Photobiol Sci 2004; 3: 749-752.
39. Stahl W, Heinrich U, Jungmann H, Sies H, Tronnier H. Carotenoids and carotenoids plus vitamin E protect against ultraviolet light-induced erythema in humans. Am J Clin Nutr 2000; 71: 795-798.
40. Heinrich U, Gärtner C, Wiebusch M, and et al. Supplementation with β-carotene or a similar amount of mixed carotenoids protects humans from UV-induced erythema. J Nutr 2003; 133: 98-101.
41. Stahl W, Heinrich U, Wiseman S, Eichler O, Sies H, Tronnier H. Dietary tomato protects against ultraviolet light-induced erythema in humans. J Nutr 2001; 131: 1449-1451.
42. Bissett DL, Hannon DP, Orr TV. An animal model of solar-aged skin: histological, physical, and visible changes in UV-irradiated hairless mouse skin. Photochem Photobiol 1987; 46: 367-378.
43. Rittié L, Fischer GJ. UV-light-induced signal cascades and skin aging. Ageing Res Rev 2002; 1: 705-720.
44. Kawaguchi Y, Tanaka H, Okada T, and et al. The effects of ultraviolet A and reactive oxygen species on the mRNA expression of 72-kDa type IV collagenase and its tissue inhibitor in cultured human dermal fibroblasts. Arch Dermatol Res 1996; 288: 39-44.
45. Ziegler ME, Chi Y, Schmit T, Varani J. Role of ERK and JNK pathways in regulating cell motility and matrix metalloproteinase 9 production in growth factor-stimulated human epidermal keratinocytes. J Cell Physiol 1999; 180: 271-284.
46. Inomata S, Matsunaga Y, Amano S, and et al. Possible involvement of gelatinases in basement membrane damage and wrinkle formation in chronically ultraviolet B-exposed hairless mouse. J Invest Dermatol 2003; 120: 128-134.
47. Minami , Y , Kawabata K, Kubo Y, and et al. Peroxidized cholesterol-induced matrix metalloproteinase-9 activation and its suppression by dietary β-carotene in photoaging of hairless mouse skin. J Nutr Biochem 2009; 20: 389-398.
48. 2) increases the steady-state mRNA levels of collagenase/MMP-1 in human dermal fibroblasts. Free Radic Biol Med 1997; 22: 515-524.
49. Akiba S, Kumazawa S, Yamaguchi H, and et al. Acceleration of matrix metalloproteinase-1 production and activation of platelet-derived growth factor receptor beta in human coronary smooth muscle cells by oxidizied LDL and 4-hydroxynonenal. Biochim Biophys Acta 2006; 1763: 797-804.
50. Girotti AW. Translocation as a means of disseminating lipid hydroperoxide-induced oxidative damage and effector action. Free Radic Biol Med 2008; 44: 956-968.
51. Geiger PG, Korytowski W, Girotti AW. Photodynamically generated 3-beta-hydroxy-5 alpha-cholestet-6-ene-5-hydroperoxide: toxic reactivity in membranes and susceptibility to enzymatic detoxification. Photochem Photobiol 1995; 62: 580-587.
52. Stratton SP, Schaefer WH, Liebler DC. Isolation and identification of singlet oxygen products of beta-carotene. Chem Res Toxicol 1993; 6: 542-547.
53. Yamauchi R, Tsuchihashi K, Kato K. Oxidation products of β-carotene during the peroxidation of methyl linoleate in the bulk phase. Biosci Biotechnol Biochem 1998; 62: 1301-1306. (Pubitemid 128473368)
54. Sakai S, Sugawara T, Matsubara K, Hirata T. Inhibitory effect of carotenoids on the degranulation of mast cells via suppression of antigen-induced aggregation of high affinity IgE receptors. J Biol Chem 2009; 284: 28172-28179.