Isolation of β-Cryptoxanthin-epoxides, Precursors of Cryptocapsin and 3′-Deoxycapsanthin, from Red Mamey (Pouteria sapota)

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 26, 2015, Pages 6059-6065

  Turcsi, Erika ^a   Murillo, Enrique ^b   Kurtán, Tibor ^c   Szappanos, Ádám ^c   Illyés, Tünde Zita ^c   Gulyás Fekete, Gergely ^a   Agócs, Attila ^a   Avar, Péter ^a   Deli, József ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

^b University of Panama   (Panama)

^c UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

carotenoids; HPLC ECD analysis; mamey; tropical fruit

Indexed keywords

CIRCULAR DICHROISM SPECTROSCOPY; DICHROISM; FRUITS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PIGMENTS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

CAROTENOIDS; CENTRAL AMERICA; ELECTRONIC CIRCULAR DICHROISM; HPLC-ECD ANALYSIS; MAMEY; NUCLEAR MAGNETIC RESONANCE(NMR); TROPICAL FRUITS; UV-VIS SPECTROSCOPY;

NUCLEAR MAGNETIC RESONANCE;

MAMMEA AMERICANA; POUTERIA SAPOTA;

3'-DEOXYCAPSANTHIN; CAPSAICIN; CAROTENOID; CRYPTOXANTHIN; EPOXIDE; PLANT EXTRACT;

CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; FRUIT; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POUTERIA;

CAPSAICIN; CAROTENOIDS; CIRCULAR DICHROISM; CRYPTOXANTHINS; EPOXY COMPOUNDS; FRUIT; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PLANT EXTRACTS; POUTERIA;

EID: 84936817594     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b01936     Document Type: Article

References (37)

1. Curl, A. L.; Bailey, G. F. The carotenoids of ruby red grapefruit J. Food Sci. 1957, 22, 63-68 10.1111/j.1365-2621.1957.tb16983.x
2. Curl, A. L.; Bailey, G. F. The carotenoids of navel oranges J. Food Sci. 1961, 26, 442-447 10.1111/j.1365-2621.1961.tb00386.x
3. Curl, A. L. The carotenoids of cling peaches J. Food Sci. 1959, 24, 413-421 10.1111/j.1365-2621.1959.tb17292.x
4. Curl, A. L. The carotenoids of Japanese persimmons J. Food Sci. 1960, 25, 670-674 10.1111/j.1365-2621.1960.tb00012.x
5. Curl, A. L. The carotenoids of red bell peppers J. Agric. Food Chem. 1962, 10, 504-509 10.1021/jf60124a020
6. Curl, A. L. The carotenoids of Italiana prunes J. Food Sci. 1963, 28, 623-626 10.1111/j.1365-2621.1963.tb01665.x
7. Purcell, A. E. Carotenoids of goldrush sweetpotato flakes Food Technol. 1962, 16, 99-102
8. Subbarayan, C.; Cama, H. R. Carotenoids in Carica papaya (papaya fruit) Indian J. Chem. 1964, 2, 451-454
9. Yamamoto, H. Y. Comparison of the carotenoids in yellow- and red-fleshed Carica papaya Nature 1964, 20, 1049-1050 10.1038/2011049a0
10. Yokoyama, H.; Vandercook, C. E. Citrus carotenoids I. Comparison of carotenoids in mature-green and yellow lemons J. Food Sci. 1967, 32, 42-48 10.1111/j.1365-2621.1967.tb01954.x
11. Yokoyama, H.; White, M. J. Carotenoids in the flavedo of Marsh seedless grapefruit J. Agric. Food Chem. 1967, 15, 693-696 10.1021/jf60152a041
12. Schaller, D. R.; Von Elbe, J. H. The carotenoids in Montmorency cherries J. Food Sci. 1971, 36, 712-713 10.1111/j.1365-2621.1971.tb15169.x
13. Gross, J.; Gabai, M.; Lifshitz, A. Carotenoids in juice of Shamouti orange J. Food Sci. 1971, 36, 466-473 10.1111/j.1365-2621.1971.tb06390.x
14. 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 10.1016/S0031-9422(00)90007-4
15. Rahman, F. M. M.; Buckle, K. A. Pigment changes in capsicum cultivars during maturation and ripening Int. J. Food Sci. Technol. 1980, 15, 241-249 10.1111/j.1365-2621.1980.tb00937.x
16. Noga, G.; Lenz, F. Separation of citrus carotenoids by reversed-phase high-performance liquid chromatography Chromatographia 1983, 17, 139-142 10.1007/BF02271036
17. Matus, Z.; Deli, J.; Szabolcs, J. Carotenoid composition of yellow pepper during ripening: isolation of β-cryptoxanthin 5,6-epoxide J. Agric. Food Chem. 1991, 39, 1907-1914 10.1021/jf00011a003
18. Godoy, H. T.; Rodriguez-Amaya, D. B.; Connor, A. E.; Britton, G. Confirmation of the structure of papaya β-cryptoxanthin monoepoxide Food Chem. 1990, 36, 281-286 10.1016/0308-8146(90)90067-E
19. Molnár, P.; Deli, J.; Matus, Z.; Tóth, G.; Steck, A.; Pfander, H. Partial synthesis and characterization of the mono- and diepoxides of β-cryptoxanthin Helv. Chim. Acta 1997, 80, 221-229 10.1002/hlca.19970800120
20. Thompson, A. J.; Jackson, A. C.; Parker, R. A.; Morpeth, D. R.; Burbidge, A.; Taylor, I. B. Abscisic acid biosynthesis in tomato: regulation of zeaxanthin epoxidase and 9- cis -epoxy-carotenoid dioxygenase mRNAs by light/dark cycles, water stress and abscisic acid Plant Mol. Biol. 2000, 42, 833-845 10.1023/A:1006448428401
21. Kalala, M.; Cowan, A. K.; Molnár, P.; Tóth, G. (9 Z)-Epoxy-carotenoid cleavage enzyme activity from the Citrus cell-free system for ABA biosynthesis S. Afr. J. Bot. 2001, 67, 376-377
22. Bouvier, F.; Hugueney, P.; d'Harlingue, A.; Kuntz, M.; Camara, B. Xanthophyll biosynthesis in chromoplast: isolation and molecular cloning of an enzyme catalyzing the conversion of 5,6-epoxycarotenoid into ketocarotenoid Plant J. 1994, 6, 45-54 10.1046/j.1365-313X.1994.6010045.x
23. Deli, J.; Matus, Z.; Tóth, G. Carotenoid composition in the fruits of Capsicum annuum cv. Szentesi Kosszarvú during ripening J. Agric. Food Chem. 1996, 44, 711-716 10.1021/jf950354n
24. Deli, J.; Tóth, G. Carotenoid composition of the fruits of Capsicum annuum cv. Bovet 4 during ripening Z. Lebensm. Unters.Forschung A 1997, 205, 388-391 10.1007/s002170050186
25. Deli, J.; Molnár, P.; Matus, Z.; Tóth, G. Carotenoid composition in the fruits of red paprika (Capsicum annuum var. lycopersiciforme rubrum) during ripening; biosynthesis of carotenoids in red paprika J. Agric. Food Chem. 2001, 49, 1517-1523 10.1021/jf000958d
26. Deli, J.; Matus, Z.; Tóth, G. Carotenoid composition in the fruits of Asparagus officinalis J. Agric. Food Chem. 2000, 48, 2793-2796 10.1021/jf991243h
27. Deli, J.; Molnár, P.; Osz, E.; Tóth, G. Analysis of the carotenoids of the fruits of Asparagus falcatus; Isolation of 5,6-diepikarpoxanthin Chromatographia 2000, 51, S183-187 10.1007/BF02492803
28. Deli, J.; Molnár, P.; Matus, Z.; Tóth, G.; Steck, A.; Pfander, H. Isolation and characterization of 3,5,6-trihydroxy-carotenoids from petals of Lilium tigrinum Chromatographia 1998, 48, 27-31 10.1007/BF02467511
29. Murillo, E.; McLean, R.; Britton, G.; Agócs, A.; Nagy, V.; Deli, J. Sapotexanthin, an A-provitamin carotenoid isolated from mamey (Pouteria sapota) J. Nat. Prod. 2011, 74, 283-285 10.1021/np1006982
30. Gulyás-Fekete, G.; Murillo, E.; Kurtán, T.; Papp, T.; Illyés, T. Z.; Drahos, L.; Visy, J.; Agócs, A.; Turcsi, E.; Deli, J. Cryptocapsinepoxide-type carotenoids from red mamey Pouteria sapota J. Nat. Prod. 2013, 76 (4) 607-614 10.1021/np3007827
31. Murillo, E.; Mosquera, Y.; Kurtán, T.; Gulyás-Fekete, G.; Nagy, V.; Deli, J. Isolation and characterization of two novel capsorubin like carotenoids from the red mamey (Pouteria sapota) Helv. Chim. Acta 2012, 95 (6) 983-988 10.1002/hlca.201100493
32. van Breemen, R. B.; Dong, L.; Pajkovic, N. D. Atmospheric pressure chemical ionization tandem mass spectrometry of carotenoids Int. J. Mass Spectrom. 2012, 312, 163-172 10.1016/j.ijms.2011.07.030
33. Englert, G. NMR spectroscopy. In Carotenoids; Britton, G.; Liaaen-Jensen, S.; Pfander, H., Eds.; Birkhauser: Basel, Switzerland, 1995; Vol. 1B, p 147.
34. Buchecker, R.; Noack, K. CD spectroscopy. In Carotenoids; Britton, G.; Liaaen-Jensen, S.; Pfander, H., Eds.; Birkhauser: Basel, Switzerland, 1995; Vol. 1B, p 81.
35. Acemoglu, M.; Eugster, C. H. (5 R,6 S,5′ R,6′ S)-5,6,5′,6′-Diepoxy-β,β-carotene-synthesis, spectroscopical and chiroptical properties, and HPLC-behaviour Helv. Chim. Acta 1984, 67, 184-190 10.1002/hlca.19840670123
36. Eschenmoser, W.; Eugster, C. H. Synthesis and chirality of (5 S,6 R)-5,6-epoxy-5,6-dihydro-β,β-carotene and (5 R,6 R)-5,6-dihydro-β,β-carotene-5,6-diol, a compound with unepected solubility characteristics Helv. Chim. Acta 1978, 61, 822-831 10.1002/hlca.19780610229
37. Maoka, T.; Akimoto, N.; Fujiwara, Y.; Hashimoto, K. Structure of new carotenoids with the 6-oxo-κ end group from the fruits of paprika Capsicum annuum J. Nat. Prod. 2004, 67, 115-117 10.1021/np030400a