Photosensitized E/Z isomerization of (all-E)-lycopene aiming at practical applications

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 47, 2014, Pages 11353-11356

  Honda, Masaki ^a   Igami, Haruyuki ^a   Kawana, Takahiro ^a   Hayashi, Kento ^b   Takehara, Munenori ^b   Inoue, Yoshinori ^b   Kitamura, Chitoshi ^b  

^a KAGOME CO   (Japan)

^b UNIVERSITY OF SHIGA PREFECTURE   (Japan)

Author keywords

Erythrosine; Lycopene; Photoisomerization; Rose bengal; Sensitizer

Indexed keywords

ACETONE; IRRADIATION; PHOTOISOMERIZATION; PLANTS (BOTANY);

ERYTHROSINE; INFRARED LIGHT; LIGHT IRRADIATIONS; LYCOPENES; ROSE BENGAL; SENSITIZER; THERMODYNAMICALLY STABLE; TOMATO PASTE;

ISOMERS;

ANTIOXIDANT; CAROTENOID; LYCOPENE; PHOTOSENSITIZING AGENT;

CHEMISTRY; FOOD HANDLING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; PROCEDURES; TOMATO;

ANTIOXIDANTS; CAROTENOIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FOOD HANDLING; ISOMERISM; LYCOPERSICON ESCULENTUM; PHOTOSENSITIZING AGENTS;

EID: 84913528787     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf504502t     Document Type: Article

References (19)

1. Holden, J. M.; Eldridge, A. L.; Beecher, G. R.; Buzzard, I. M.; Bhagwat, S.; Davis, C. S.; Douglass, L. W.; Gebhardt, S.; Haytowitz, D.; Schakel, S. Carotenoid content of U.S. foods: an update of the database. J. Food Compos. Anal. 1999, 12, 169-196.
2. Khoo, H.-E.; Prasad, K. N.; Kong, K.-W.; Jiang, Y.; Ismail, A. Carotenoids and their isomers: color pigments in fruits and vegetables. Molecules 2011, 16, 1710-1738.
3. Schieber, A.; Carle, R. Occurrence of carotenoid cis-isomers in food: technological, analytical, and nutritional implications. Trends Food Sci. Technol. 2005, 16, 416-422.
4. Stahl, W.; Schwarz, W.; Sundquist, A. R.; Sies, H. cis-trans isomers of lycopene and β-carotene in human serum and tissues. Arch. Biochem. Biophys. 1992, 294, 173-177.
5. Boileau, A. C.; Merchen, N. R.; Wasson, K.; Atkinson, C. A.; Erdman, J. W., Jr. cis-Lycopene is more bioavailable than translycopene in vitro and in vivo in lymph-cannulated ferrets. J. Nutr. 1999, 129, 1176-1181.
6. Richelle, M.; Sanchez, B.; Tavazzi, I.; Lambelet, P.; Bortlik, K.; Williamson, G. Lycopene isomerisation takes place within enterocytes during absorption in human subjects. Br. J. Nutr. 2010, 103, 1800-1807.
7. Richelle, M.; Lambelet, P.; Rytz, A.; Tavazzi, I.; Mermoud, A.-F.; Juhel, C.; Borel, P.; Bortlik, K. The proportion of lycopene isomers in human plasma is modulated by lycopene isomer profile in the meal but not by lycopene preparation. Br. J. Nutr. 2012, 107, 1482-1488.
8. Failla, M. L.; Chitchumroonchokchai, C.; Ishida, B. K. In vitro micellarization and intestinal cell uptake of cis isomers of lycopene exceed those of all-trans lycopene. J. Nutr. 2008, 138, 482-486.
9. Unlu, N. Z.; Bohn, T.; Francis, D. M.; Nagaraja, H. N.; Clinton, S. K.; Schwartz, S. J. Lycopene from heat-induced cis-isomer-rich tomato sauce is more bioavailable than from all-trans-rich tomato sauce in human subjects. Br. J. Nutr. 2007, 98, 140-146.
10. Müller, L.; Goupy, P.; Fröhlich, K.; Dangles, O.; Caris-Veyrat, C.; Böhm, V. Comparative study on antioxidant activity of lycopene (Z)-isomers in different assays. J. Agric. Food Chem. 2011, 59, 4504-4511.
11. Honda, M.; Takahashi, N.; Kuwa, T.; Takehara, M.; Inoue, Y.; Kumagai, T. Spectral characterization of Z-isomers of lycopene formed during heat treatment and solvent effects on the E/Z isomerization process. Food Chem. 2015, 171, 323-329.
12. Takehara, M.; Nishimura, M.; Kuwa, T.; Inoue, Y.; Kitamura, C.; Kumagai, T.; Honda, M. Characterization and thermal isomerization of (all-E)-lycopene. J. Agric. Food Chem. 2014, 62, 264-269.
13. Jensen, N. H.; Nielsen, A. B.; Wilbrandt, R. Chlorophyll a sensitized trans-cis photoisomerization of all-trans-β-carotene. J. Am. Chem. Soc. 1982, 104, 6117-6119.
14. 1 state. J. Phys. Chem. 1991, 95, 7171-7180.
15. Stahl, W.; Sundquist, A. R.; Hanusch, M.; Schwarz, W.; Sies, H. Separation of β-carotene and lycopene geometrical isomers in biological samples. Clin. Chem. 1993, 39, 810-814.
16. Lee, M. T.; Chen, B. H. Stability of lycopene during heating and illumination in a model system. Food Chem. 2002, 78, 425-431.
17. Ideses, R.; Shani, A. Study of the radical mechanism of iodinecatalyzed isomerization of conjugated diene systems. J. Am. Oil Chem. Soc. 1989, 66, 948-952.
18. Guo, W.-H.; Tu, C.-Y.; Hu, C.-H. cis-trans isomerizations of β-carotene and lycopene: a theoretical study. J. Phys. Chem. B 2008, 112, 12158-12167.
19. DeRosa, M. C.; Crutchley, R. J. Photosensitized singlet oxygen and its applications. Coord. Chem. Rev. 2002, 233-234, 351-371.