Decreased Stability of Bisphenol A by Photosensitization

감광제 광산화에 의한 Bisphenol A 안정성 감소

  • Received : 2009.11.04
  • Accepted : 2009.12.19
  • Published : 2010.06.30

Abstract

Bisphenol A (BPA) is an endocrine disruptor frequently used in food containers, including epoxy resin and polycarbonates. BPA concentrations were monitored by high performance liquid chromatography (HPLC) under photosensitization of riboflavin (RF), methylene blue (MB), rose bengal (RB), or titanium dioxide ($TiO_2$) and the involvement of singlet oxygen was determined using sodium azide ($NaN_3$). The stability of BPA decreased significantly in the order of RF, RB, and MB photosensitization (p<0.05), while the concentration of BPA in samples with $TiO_2$ was not significantly different from that of control samples without photosensitizers under light (p>0.05). The stability of BPA decreased in an MB concentration-dependent manner and increased as the concentration of added $NaN_3$ increased, implying that singlet oxygen was involved in the photodegradation of BPA during MB photosensitization. The results of this study may help control the BPA content in foods or the environments using photosensitized oxidation and visible light irradiation.

Keywords

bisphenol A;photosensitization;singlet oxygen;methylene blue

References

  1. Ballesteros-Gomez A, Rubio S, Perez-Bendito D. Analytical methods for the determination of bisphenol A in food. J. Chromatogr. A 1216: 449-469 (2009) https://doi.org/10.1016/j.chroma.2008.06.037
  2. Vandenberg LN, Hauser R, Marcus M, Olea N, Welshons WV. Human exposure to bisphenol A (BPA). Reprod. Toxicol. 24: 139-177 (2007) https://doi.org/10.1016/j.reprotox.2007.07.010
  3. Bergeron RM, Thompson TB, Leonard LS, Pluta L, Gaido KW. Estrogenicity of bisphenol A in a human endometrial carcinoma cell line. Mol. Cell. Endocrinol. 150: 179-187(1999) https://doi.org/10.1016/S0303-7207(98)00202-0
  4. Kaneko M, Okada R, Yamamoto K, Nakamura M, Mosconi G, Polzonetti-Magni AM, Kikuyama S. Bisphenol A acts differently from and independently of thyroid hormone in suppressing thyrotropin release from the bullfrog pituitary. Gen. Comp. Endocr. 155: 574-580 (2008) https://doi.org/10.1016/j.ygcen.2007.09.009
  5. Keri RA, Ho SM, Hunt PA, Knudsen KE, Soto AM, Prins GS. An evaluation of evidence for the carcinogenic activity of bisphenol A. Reprod. Toxicol. 24: 240-252 (2007) https://doi.org/10.1016/j.reprotox.2007.06.008
  6. Lin Y, Shi Y, Jiang M, Jin Y, Peng Y, Lu B, Dai K. Removal of phenolic estrogen pollutants from different sources of water using molecularly imprinted polymeric microspheres. Environ. Pollut. 153: 483-491 (2008) https://doi.org/10.1016/j.envpol.2007.08.001
  7. Ioan I, Wilson S, Lundanes E, Neculai A. Comparison of Fenton and sono-Fenton bisphenol A degradation. J. Hazard. Mater. 142: 559-563 (2007) https://doi.org/10.1016/j.jhazmat.2006.08.015
  8. Zhan M, Yang X, Xian Q, Kong L. Photosensitized degradation of bisphenol A involving reactive oxygen species in the presence of humic substances. Chemosphere 63: 378-386 (2006) https://doi.org/10.1016/j.chemosphere.2005.08.046
  9. Xie YB, Li XZ. Degradation of bisphenol A in aqueous solution by $H_{2}O_{2}$-assisted photoelectrocatalytic oxidation. J. Hazard. Mater. 138: 526-533 (2006) https://doi.org/10.1016/j.jhazmat.2006.05.074
  10. Katsumata H, Kawabe S, Kaneco S, Suzuki T, Ohta K. Degradation of bisphenol A in water by the photo-Fenton reaction. J. Photoch. Photobio. A 162: 297-305 (2004) https://doi.org/10.1016/S1010-6030(03)00374-5
  11. Ha DO, Jeong MK, Park CU, Park MH, Chang PS, Lee JH. Effect of riboflavin photosensitization on the degradation of bisphenol A (BPA) in model and real-food systems. J. Food Sci. 74: 380-384 (2009) https://doi.org/10.1111/j.1750-3841.2009.01172.x
  12. Foote CS, Denny RW. Chemistry of singlet oxygen quenching by $\beta$-carotene. J. Am. Chem. Soc. 90: 6232-6238 (1968) https://doi.org/10.1021/ja01024a060
  13. Boff JM, Min DB. Chemistry and reaction of singlet oxygen in foods. Compr. Rev. Food Sci. F. 1: 58-72. (2002) https://doi.org/10.1111/j.1541-4337.2002.tb00007.x
  14. King JM, Min DB. Riboflavin photosensitized singlet oxygen oxidation of vitamin D. J. Food Sci. 63: 31-34 (1998) https://doi.org/10.1111/j.1365-2621.1998.tb15669.x
  15. Skibsted LH. Light-induced changes in dairy products. Bull. Int. Dairy Fed. 346: 4-9 (2000)
  16. Diaz M, Luiz M, Alegretti P, Furlong J, Amat-Guerri F, Massad W, Criado S, Garci NA. Visible-light-mediated photodegradation of 17$\beta$-estradiol: Kinetics, mechanism and photoproducts. J. Photoch. Photobio. A 202: 221-227 (2009) https://doi.org/10.1016/j.jphotochem.2008.12.008
  17. Fischer BB, Krieger-Liszkay A, Eggen RIL. Oxidative stress induced by the photosensitizers neutral red (type I) or rose bengal (type II) in the light causes different molecular responses in Chlamydomonas reinhardtii. Plant Sci. 168: 747-759 (2005) https://doi.org/10.1016/j.plantsci.2004.10.008
  18. Kim JI, Lee JH, Choi DS, Won BM, Jung MY, Park JY. Kinetic study of the quenching reaction of singlet oxygen by common synthetic antioxidants (tert-butylhydroxyanisol, tert-di-butylhydroxytoluene, and tert-butylhydroquinone) as compared with $\alpha$-tocopherol. J. Food Sci. 74: 362-369 (2009)
  19. Lee JM, Chang PS, Lee JH. Effects of photosensitisation and autoxidation on the changes of volatile compounds and headspace oxygen in elaidic trans fatty acid and oleic cis fatty acid. Food Chem. 119: 88-94 (2010) https://doi.org/10.1016/j.foodchem.2009.05.077
  20. Oh YS, Jang ES, Bock JY, Yoon SH, Jung MY. Singlet oxygen quenching activities of various fruit and vegetable juices and protective effects of apple and pear juices against hematolysis and protein oxidation induced by methylene blue photosensitization. J. Food Sci. 71: 260-268 (2006) https://doi.org/10.1111/j.1750-3841.2006.00014.x
  21. Chang HS, Kim JE, Chung DJ, Lee JS, Choi CB, Kim HY. The antibacterial effect of photo-catalytic titanium dioxide on canine skin. Korean J. Vet. Res. 46: 279-284 (2006)
  22. Kim HY, Yang WH. Development of wastewater treatment system by energy-saving photocatalyst using combination of solar light, UV lamp and $TiO_{2}$. Kor. J. Env. Health 29: 51-61 (2003)
  23. Barbieri Y, Massad WA, Diaz DJ, Sanz J, Amat-Guerri F, García NA. Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin:Kinetics, mechanism, and photoproducts. Chemosphere 73: 564-571 (2008) https://doi.org/10.1016/j.chemosphere.2008.06.013
  24. Lee JH, Min DB. Changes of headspace volatiles in milk with riboflavin photosensitization. J. Food Sci. 74: C563-568 (2009) https://doi.org/10.1111/j.1750-3841.2009.01295.x
  25. Yang SO, Lee SW, Chung J, Lee JH. Stability of isoflavone daidzein and genistein in riboflavin, chlorophyll b, or methylene blue photosensitization. J. Food Sci. 73: 100-105 (2008)
  26. Lee SW, Chang PS, Lee JH. Effects of riboflavin photosensitization on the changes of isoflavones in soymilk. J. Food Sci. 73: 551-555 (2008) https://doi.org/10.1111/j.1750-3841.2008.00881.x
  27. Yang SO, Lee JM, Lee JC, Lee JH. Effects of riboflavin-photosensitization on the formation of volatiles in linoleic acid model systems with sodium azide or $D_{2}O$. Food Chem. 105: 1375-1381 (2007) https://doi.org/10.1016/j.foodchem.2007.05.002
  28. DeRosa MC, Crutchley RJ. Photosensitized singlet oxygen and its applications. Coordin. Chem. Rev. 233-234: 351-371 (2002) https://doi.org/10.1016/S0010-8545(02)00034-6
  29. Imai S, Shiraishi A, Gamo K, Watanabe I, Okuhata H, Miyasaka H, Ikeda K, Bamba T, Hirata K. Removal of phenolic endocrine disruptors by Portulaca oleracea. J. Biosci. Bioeng. 103: 420-426 (2007) https://doi.org/10.1263/jbb.103.420