Photoirradiation of azulene and guaiazulene-Formation of reactive oxygen species and induction of lipid peroxidation

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 211, Issue 2-3, 2010, Pages 123-128

  Chiang, Hsiu Mei ^a   Yin, Jun Jie ^b   Xia, Qingsu ^c   Zhao, Yuewei ^c   Fu, Peter P ^c   Wen, Kuo Ching ^a   Yu, Hongtao ^d  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^c NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

^d JACKSON STATE UNIVERSITY   (United States)

Author keywords

Azulene; Guaiazulene; Lipid peroxidation; Photoirradiation; Reactive oxygen species; UVA light

Indexed keywords

EID: 77952011136     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.02.007     Document Type: Article

References (37)

1. Andersen F.A., Teufel D.R. Final report on the safety assessment of azulene. Inter. J. Toxicol. 1999, 18:27-32.
2. Guarrera M., Turbino L., Rebora A. The anti-inflammatory activity of azulene. J. Eur. Acad. Dermatol. Venereol. 2001, 15:486-487.
3. Wang L., Yan J., Fu P.P., Parekh K.A., Yu H. Photomutagenicity of cosmetic ingredient chemicals azulene and guaiazulene. Mutat. Res. 2003, 530:19-26.
4. Wang L., Yan J., Cohly H., Hwang H.M., Wang S., Fu P.P., Yu H. Photo-acute toxicity and genotoxicity of azulene on human Jurkat T-cells. Mutat. Res. Gen. Toxicol. Environ. Mutagen. 2004, 562:143-150.
5. Anderstam B., Vaca C., Harms-Ringdahl M. Lipid peroxide levels in a murine adenocarcinoma exposed to hyperthermia: the role of glutathione depletion. Radiat. Res. 1992, 132:296-300.
6. Kourounakis A.P., Rekka E.A., Kourounakis P.N. Antioxidant activity of guaiazulene and protection against paracetamol hepatotoxicity in rats. J. Pharm. Pharmacol. 1997, 49:938-942.
7. Yanagisawa T., Kosakai K., Tomiyama T., Yasunami M., Takase K. Study on anti-ulcer agents. II. Synthesis and anti-ulcer activities of 6-isopropylazulene-I-sodium sulphonate derivatives. Chem. Pharm. Bull. 1990, 38:3355-3358.
8. Balato N., Lembo G., Nappa P., Ayala F. Allergic cheilitis to azulene. Contact Derm. 1985, 13:76-82.
9. Fiori J., Gotti R., Valgimigli L., Cavrini V. Guaiazulene in health care products: determination by GC-MS and HPLC-DAD and photostability test. J. Pharm. Biomed. Anal. 2008, 47:710-715.
10. Cherng S.H., Xia Q., Blankenship L.R., Freeman J.P., Wamer W.G., Howard P.C., Fu P.P. Photodecomposition of retinyl palmitate in ethanol by UVA light-formation of photodecomposition products, reactive oxygen species, and lipid peroxides. Chem. Res. Toxicol. 2005, 18:129-138.
11. Arimoto-Kobayashi S., Anma N., Yoshinaga Y., Douki T., Cadet J., Hayatsu H. Oxidative damage and induced mutations in m13mp2 phage DNA exposed to N-nitrosopyrrolidine with UVA radiation. Mutagenesis 2000, 15:473-477.
12. Yu H.B., Jin W., Ho H.L., Chan K.C., Chan C.C., Demokan M.S., Stewart G., Culshaw B., Liao Y.B. Multiplexing of optical fiber gas sensors with a frequency modulated continuous-wave technique. Appl. Opt. 2001, 40:1011-1020.
13. Jeanmougin M., Civatte J. Dosimetry of solar ultraviolet radiation. Daily and monthly changes in Paris. Ann. Dermatol. Venereol. 1987, 114:671-676.
14. Balasaraswathy P., Kumar U., Srinivas C.R., Nair S. UVA and UVB in sunlight, optimal utilization of UV rays in sunlight for phototherapy. Indian J. Dermatol. Venereol. Leprol. 2002, 68:198-201.
15. Tokita M., Morita M. Identification of new geometric isomers of methyl linoleate hydroperoxide and their chromatographic behavior. Biosci. Biotechnol. Biochem. 2000, 64:1044-1056.
16. Ogilby P.R., Foote C.S. Chemistry of singlet oxygen. 42. Effect of solvent, solvent isotopic substitution, and temperature on the lifetime of singlet molecular oxygen. J. Am. Chem. Soc. 1983, 105:3423-3430.
17. Rinalducci S., Pedersen J.Z., Zolla L. Formation of radical from signet oxygen produced during photoinhibition of isolated light-harvesting protein of photosystem II. Biochim. Biophys. Acta 2004, 1608:63-73.
18. Xia Q., Yin J.J., Cherng S.H., Wamer W.G., Boudreau M., Howard P.C., Fu P.P. UVA photodecomposition of retinyl palmitate-formation of singlet oxygen and superoxide, and their role in induction of lipid peroxidation. Toxicol. Lett. 2006, 163:30-43.
19. Lion Y., Delmelle M., Van De Vorst A. New method of detecting singlet oxygen production. Nature 1976, 263:442-443.
20. Lion Y., Grandin E., Van De Vorst A. On the production of nitroxide radicals by singlet oxygen reaction: an ESR study. J. Photochem. Photobiol. 1980, 31:305-309.
21. Zhao H., Joseph J., Zhang H., Karoui H., Kalyanaraman B. Synthesis and biochemical applications of a solid cyclic Nitrone spin trap: a relatively superior trap for detecting superoxide anions and glutathiyl radicals. Free Radic. Biol. Med. 2001, 31:599-606.
22. Yu H. Environmental carcinogenic polycyclic aromatic hydrocarbons: photochemistry and phototoxicity. J. Environ. Sci. Health C: Environ. Carcinog. Ecotoxicol. Rev. 2002, C20:149-183.
23. Yu H., Xia Q., Yan J., Herreno-Saenz D., Wu Y.-S., Tang I.-W., Fu P.P. Photoirradiation of polycyclic aromatic hydrocarbons with UVA light-a pathway leading to the generation of reactive oxygen species, lipid peroxidation, and DNA damage. Int. J. Environ. Res. Public Health 2006, 3:348-354.
24. Selco J.I., Brooks T., Chang M., Trieu M.T., McDonald J.K., McManus S.P. Solution photochemistry of azulene. J. Org. Chem. 1994, 59:429-433.
25. Fiori J., Gotti R., Albini A., Cavrini V. Study on the photostability of guaiazulene by highperformance liquid chromatography/mass spectrometry and gas chromatography/mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22:2698-2706.
26. Kagan J. Organic Photochemistry 1993, Academic Press, San Diego.
27. Kraljic I., El Mohsni S. A new method for the detection of singlet oxygen in aqueous solutions. J. Photochem. Photobiol. 1978, 28:577-581.
28. Foote C.S. Definition of type I and type II photosensitized oxidation. J. Photochem. Photobiol. 1991, 54:659.
29. Chung F.L., Chen H.J.C., Guttenplan J.B., Nishikawa A., Hard G.C. 2,3-Epoxy-4-hydroxynonenal as a potential tumor-initiating agent of lipid peroxidation. Carcinogenesis 1993, 14:2073-2077.
30. Gardner M.J., Pannett B., Winter P.D. A cohort study of workers exposed to formaldehyde in the British chemical industry: an update. Br. J. Ind. Med. 1993, 50:827-834.
31. Chaudhary A.K., Nokubo M., Reddy G.R., Yeola S.N., Morrow J.D., Blair L.A., Marnett L.J. Detection of endogenous malondialdehyde-deoxyguanosine adducts in human liver. Science 1994, 265:1580-1582.
32. Esterbauer H., Zollner H., Schaur R.J. Aldehydes formed by lipid peroxidation: mechanisms of formation, occurrence, and determination. Membrane Lipid Oxidation 1990, 239-268. CRC Press, Boca Raton. C. Vigo-Pelfrey (Ed.).
33. Banni S., Evans R.W., Salgo M.G., Corongui F.P., Lombardi B. Conjugated diene and trans fatty acids in a choline-devoid diet hepatocarcinogenic in the rat. Carcinogenesis 1990, 11:2047-2051.
34. Stadtman E.R., Berlett B.S. Reactive oxygen-mediated protein oxidation in aging and disease. Chem. Res. Toxicol. 1997, 10:485-494.
35. Burkle A. Mechanism of ageing. Eye 2001, 15:371-375.
36. Floyd R.A., West M., Hensley K. Oxidative biochemical markers: clues to understanding aging in long-lived species. Exp. Gerontol. 2001, 36:619-640.
37. Loft S., Poulsen H.E. Cancer risk and oxidative DNA damage in man. J. Mol. Med. 1996, 74:297-312.