Identification of isolutein (lutein epoxide) as cis-antheraxanthin in orange juice

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 24, 2005, Pages 9369-9373

  Meléndez Martínez, Antonio J ^a   Britton, George ^b   Vicario, Isabel M ^a   Heredia, Francisco J ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Antheraxanthin; C30; Carotenoids; Isolutein; Lutein epoxide; Orange juice

Indexed keywords

ANTHERAXANTIN; FLAVONOID; OROBOL; XANTHOPHYLL;

ARTICLE; BEVERAGE; CHEMISTRY; FRUIT; STEREOISOMERISM; SWEET ORANGE; THIN LAYER CHROMATOGRAPHY;

BEVERAGES; CHROMATOGRAPHY, THIN LAYER; CITRUS SINENSIS; FLAVONOIDS; FRUIT; STEREOISOMERISM; XANTHOPHYLLS;

CITRUS; TARAXACUM OFFICINALE;

EID: 28944442866     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051722i     Document Type: Article

References (41)

1. Meléndez-Martínez, A. J.; Vicario, I. M.; Heredia, F. J. Application of tristimulus colorimetry to estimate the carotenoids content in ultrafrozen orange juices. J. Agric. Food Chem. 2003, 51, 7266-7270.
2. Meléndez-Martínez, A. J.; Britton, G.; Vicario, I. M.; Heredia-Mira, F. J. Color and carotenoid profile of Spanish Valencia late ultrafrozen orange juices. Food Res. Int. 2005, 38, 931-936.
3. Meléndez-Martínez, A. J.; Vicario, I. M.; Heredia, F. J. Instrumental measurement of orange juice colour: A review. J. Sci. Food Agric. 2005, 85, 894-901.
4. Olson, J. A. Carotenoids and human health. Arch. Latinoam. Nutr. 1999, 49, 7-11.
5. Fraser, P. D.; Bramley, P. M. The biosynthesis and nutritional uses of carotenoids. Prog. Lipid Res. 2004, 43, 228-265.
6. Meléndez-Martínez, A. J.; Vicario, I. M.; Heredia, F. J. Importancia nutricional de los pigmentos carotenoides. Arch. Latinoam. Nutr. 2004, 54, 149-154.
7. Rouseff, R.; Raley, L.; Hofsommer, H. J. Application of diode array detection with a C-30 reversed phase column for the separation and identification of saponified orange juice carotenoids. J. Agric. Food Chem. 1996, 44, 2176-2181.
8. Mouly, P. P.; Gaydou, E. M.; Corsetti, J. Determination of the geographical origin of Valencia orange juice using carotenoid liquid chromatographic profiles. J. Chromatogr. A 1999, 844, 149-159.
9. Lee, H. S.; Castle, W. S.; Coates, G. A. High-performance liquid chromatography for the characterization of carotenoids in the new sweet orange (Earlygold) grown in Florida, USA. J. Chromatogr. A 2001, 913, 371-377.
10. Meléndez-Martínez, A. J.; Vicario, I. M.; Heredia, F. J. A routine high-performance liquid chromatography method for carotenoid determination in ultrafrozen orange juices. J. Agric. Food Chem. 2003, 51, 4219-4224.
11. Lee, H. S.; Castle, W. S. Seasonal changes of carotenoid pigments and color in Hamlin, Earlygold, and Budd Blood orange juices. J. Agric. Food Chem. 2001, 49, 877-882.
12. Lee, H. S. Characterization of carotenoids in juice of red navel orange (Cara Cara). J. Agric. Food Chem. 2001, 49, 2563-2568.
13. 30-bonded stationary phase of monohydroxycarotenoids with variable chain length or degree of desaturation and of lycopene isomers synthesized by various carotene desaturases. J. Chromatogr. A 2001, 956, 59-69.
14. 30 column in reversed-phase liquid chromatography. J. Agric. Food Chem. 1996, 44, 3887-3893.
15. 30 stationary phases for the analysis of food by liquid chromatography. J. Chromatogr. A 2000, 880, 189-202.
16. Britton, G. Worked examples of isolation and analysis. Example 1: Higher plants. In Carotenoids. Volume 1A: Isolation and Analysis; Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; Birkhäuser: Basel, Switzerland, 1995; pp 201-214.
17. Britton, G. Carotenoids. In Methods in Plant Biochemistry; Dey, P. M., Harborne, J. B., Eds.; Academic Press: London, United Kingdom, 1991; pp 473-518.
18. Mínguez-Mosquera, M. I. Clorofilas y Carotenoides en Tecnología de los Alimentos; Secretariado de publicaciones de la Universidad de Sevilla: Sevilla, Spain, 1997.
19. Barua, A. B.; Olson, J. A. Xanthophyll epoxides, unlike β-carotene monoepoxides, are not detectibly absorbed by humans. J. Nutr. 2001, 131, 3212-3215.
20. Barua, A. B. Improved normal-phase and reversed phase gradient high-performance liquid chromatography procedures for the analysis of retinoids and carotenoids in human serum, plant and animal tissues. J. Chromatogr. A 2001, 936, 71-82.
21. Britton, G.; Liaaen-Jensen, S.; Pfander, H. Carotenoids. Handbook; Birkhäuser: Basel, Switzerland, 2004.
22. Britton, G.; Liaaen-Jensen, S.; Pfander, H. Carotenoids. Volume 1A: Isolation and Analysis; Birkhäuser: Basel, Switzerland, 1995.
23. Meléndez-Martínez, A. J. Estudio de los carotenoides y del color de zumos de naranja. Ph.D. Thesis, Facultad de Farmacia, Universidad de Sevilla, 2005.
24. Eugster, C. H. Chemical derivatization: Microscale tests for the presence of common functional groups in carotenoids. In Carotenoids. Volume 1A: Isolation and Analysis; Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; Birkhäuser: Basel, Switzerland, 1995; pp 71-80.
25. Britton, G.; Young, A. Methods for isolation and analysis of carotenoids. In Carotenoids in Photosynthesis; Young, A., Britton, G., Eds.; Chapman & Hall: London, United Kingdom, 1993; pp 409-458.
26. Mercadante, A. Z.; Britton, G.; Rodriguez-Amaya, D. B. Carotenoids from yellow passion fruit (Passiflora edulis). J. Agric. Food Chem. 1998, 46, 4102-4106.
27. Meléndez-Martínez, A. J.; Britton, G.; Vicario, I. M.; Heredia, F. J. Identification of zeinoxanthin in orange juices. J. Agric. Food Chem. 2005, 53, 6362-6367.
28. Hart, D. J.; Scott, K. J. Development and evaluation of an HPLC method for the analysis of carotenoids in foods, and the measurement of the carotenoid content of vegetables and fruits commonly consumed in the UK. Food Chem. 1995, 54, 101-111.
29. Mercadante, A. Z.; Rodriguez-Amaya, D. B.; Britton, G. HPLC and mass spectrometric analysis of carotenoids from mango. J. Agric. Food Chem. 1997, 45, 120-123.
30. Strand, A.; Kvernberg, K.; Karlsen, A. M.; Liaaen-Jensen, S. Geometrical EIZ isomers of (6R)- and (6S)-neoxanthin and biological implications. Biochem. Syst. Ecol. 2000, 28, 443-455.
31. Rodriguez-Amaya, D. B. A Guide to Carotenoid Analysis in Foods; ILSI Press: Washington, DC, 2001.
32. Saleh, M. H.; Tan, B. Separation and identification of cis/trans carotenoid isomers. J. Agric. Food Chem. 1991, 39, 1438-1443.
33. Phillip, D.; Molnar, P.; Toth, G.; Young, A. J. Light-induced formation of 13-cis violaxanthin in leaves of Hordeum vulgare. J. Photochem. Photobiol., B 1999, 49, 89-95.
34. Rodriguez-Amaya, D. Changes in carotenoids during processing and storage of foods. Arch. Latinoam. Nutr. 1999, 49, 38-47.
35. Mercadante, A. Z.; Rodriguez-Amaya, D. B. Effects of ripening, cultivar differences, and processing on the carotenoid composition of mango. J. Agric. Food Chem. 1998, 46, 128-130.
36. Meléndez-Martínez, A. J.; Vicario, I. M.; Heredia, F. J. Estabilidad de los pigmentos carotenoides en los alimentos. Arch. Latinoam. Nutr. 2004, 54, 209-215.
37. Liaaen-Jensen, S. Combined approach: Identification and structure elucidation of carotenoids. In Carotenoids. Vol. 1B: Spectroscopy; Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; Birkhäuser: Basel, Switzerland, 1995; pp 343-354.
38. Gross, J.; Gabai, M.; Lifshitz, A. A comparative study of the carotenoid pigments in juice of Shamouti, Valencia and Washington oranges, three varieties of Citrus Sinensis. Phytochemistry 1972, 11, 303-308.
39. Gross, J.; Gabai, M.; Lifshitz, A. Carotenoids in juice of Shamouti orange. J. Food Sci. 1971, 36, 466-473.
40. Mouly, P. P.; Gaydou, E. M.; Lapierre, L.; Corsetti, J. Differentiation of several geographical origins in single-strength Valencia orange juices using quantitative comparison of carotenoid profiles. J. Agric. Food Chem. 1999, 47, 4038-4045.
41. Goodner, K. L.; Rouseff, R. L.; Hofsommer, H. J. Orange, mandarin, and hybrid classification using multivariate statistics based on carotenoid profiles. J. Agric. Food Chem. 2001, 49 (3), 1146-1150.