Thermal Degradation of Major Gomphrenin Pigments in the Fruit Juice of Basella alba L. (Malabar Spinach)

Journal of Agricultural and Food Chemistry

Volumn 65, Issue 34, 2017, Pages 7500-7508

  Kumorkiewicz, Agnieszka ^a   Wybraniec, Sławomir ^a  

^a CRACOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Basella alba; betacyanins; betalains; betanidin; decarboxylated and dehydrogenated gomphrenins; Malabar spinach; plant pigments

Indexed keywords

CARBOXYLATION; FRUIT JUICES; MASS SPECTROMETRY;

BASELLA ALBA; BETACYANINS; BETALAINS; BETANIDIN; DECARBOXYLATED AND DEHYDROGENATED GOMPHRENINS; MALABAR SPINACH; PLANT PIGMENTS;

FRUITS;

BETALAIN; GOMPHRENIN I; PIGMENT; PLANT EXTRACT;

ANALYSIS; ANGIOSPERM; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FRUIT AND VEGETABLE JUICE; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ANGIOSPERMS; BETALAINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUIT AND VEGETABLE JUICES; HOT TEMPERATURE; PIGMENTS, BIOLOGICAL; PLANT EXTRACTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 85028552385     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.7b02357     Document Type: Article

References (36)

1. Adhikari, R.; Kumar, N. H. N.; Shruthi, S. D. A Review on medicinal importance of Basella alba L Int. J. Pharm. Sci. Drug Res. 2012, 4, 110-114
2. Kumar, S. S.; Manoj, P.; Giridhar, P. Nutrition facts and functional attributes of foliage of Basella spp LWT-Food Sci. Technol. 2015, 64, 468-474 10.1016/j.lwt.2015.05.017
3. Kumar, S. S.; Manoj, P.; Giridhar, P.; Shrivastava, R.; Bharadwaj, M. Fruit extracts of Basella rubra that are rich in bioactives and betalains exhibit antioxidant activity and cytotoxicity against human cervical carcinoma cells J. Funct. Foods 2015, 15, 509-515 10.1016/j.jff.2015.03.052
4. Kumar, S. S.; Manoj, P.; Giridhar, P. A method for red-violet pigments extraction from fruits of Malabar spinach (Basella rubra) with enhanced antioxidant potential under fermentation J. Food Sci. Technol. 2015, 52, 3037-3043 10.1007/s13197-014-1335-5
5. Kumar, S. S.; Manoj, P.; Shetty, N. P.; Prakash, M.; Giridhar, P. Characterization of major betalain pigments-gomphrenin, betanin and isobetanin from Basella rubra L. fruit and evaluation of efficacy as a natural colourant in product (ice cream) development J. Food Sci. Technol. 2015, 52, 4994-5002 10.1007/s13197-014-1527-z
6. Khan, M. I.; Giridhar, P. Plant betalains: Chemistry and biochemistry Phytochemistry 2015, 117, 267-295 10.1016/j.phytochem.2015.06.008
7. Azeredo, H. M. C. Betalains: properties, sources, applications, and stability-a review Int. J. Food Sci. Technol. 2009, 44, 2365-2376 10.1111/j.1365-2621.2007.01668.x
8. Wybraniec, S.; Starzak, K.; Pietrzkowski, Z. Chlorination of betacyanins in several hypochlorous acid systems J. Agric. Food Chem. 2016, 64, 2865-2874 10.1021/acs.jafc.5b06020
9. Tesoriere, L.; Butera, D.; Allegra, M.; Fazzari, M.; Livrea, M. A. Distribution of betalain pigments in red blood cells after consumption of cactus pear fruits and increased resistance of the cells to ex vivo induced oxidative hemolysis in humans J. Agric. Food Chem. 2005, 53, 1266-1270 10.1021/jf048134+
10. Kapadia, G. J.; Azuine, M. A.; Sridhar, R.; Okuda, Y.; Tsuruta, A.; Ichiishi, E.; Mukainake, T.; Takasaki, M.; Konoshima, T.; Nishino, H.; Tokuda, H. Chemoprevention of DMBA-induced UV-B promoted, NOR-1-induced TPA promoted skin carcinogenesis, and DEN-induced phenobarbital promoted liver tumors in mice by extract of beetroot Pharmacol. Res. 2003, 47, 141-148 10.1016/S1043-6618(02)00285-2
11. Kanner, J.; Harel, S.; Granit, R. Betalains-A new class of dietary cationized antioxidants J. Agric. Food Chem. 2001, 49, 5178-5185 10.1021/jf010456f
12. Escribano, J.; Pedreño, M. A.; García-Carmona, F.; Muñoz, R. Characterization of the antiradical activity of betalains from Beta vulgaris L. roots Phytochem. Anal. 1998, 9, 124-127 10.1002/(SICI)1099-1565(199805/06)9:3<124::AID-PCA401>3.0.CO;2-0
13. Butera, D.; Tesoriere, L.; Di Gaudio, F.; Bongiorno, A.; Allegra, M.; Pintaudi, A. M.; Kohen, R.; Livrea, M. A. Antioxidant activities of Sicilian prickly pear (Opuntia ficus- indica) fruit extracts and reducing properties of its betalains: betanin and indicaxanthin J. Agric. Food Chem. 2002, 50, 6895-6901 10.1021/jf025696p
14. Cai, Y.; Sun, M.; Corke, H. Antioxidant activity of betalains from plants of the Amaranthaceae J. Agric. Food Chem. 2003, 51, 2288-2294 10.1021/jf030045u
15. Gandía-Herrero, F.; Escribano, J.; García-Carmona, F. Structural implications on color, fluorescence, and antiradical activity in betalains Planta 2010, 232, 449-460 10.1007/s00425-010-1191-0
16. Wybraniec, S.; Stalica, P.; Spórna, A.; Mizrahi, Y. Profiles of betacyanins in epidermal layers of grafted and light-stressed cacti studied by LC-DAD-ESI-MS/MS J. Agric. Food Chem. 2010, 58, 5347-5354 10.1021/jf100065w
17. Gandía-Herrero, F.; Escribano, J.; García-Carmona, F. The role of phenolic hydroxy groups in the free radical scavenging activity of betalains J. Nat. Prod. 2009, 72, 1142-1146 10.1021/np900131r
18. Tesoriere, L.; Butera, D.; D'Arpa, D.; Di Gaudio, F.; Allegra, M.; Gentile, C.; Livrea, M. A. Increased resistance to oxidation of betalain enriched human low density lipoproteins Free Radical Res. 2003, 37, 689-696 10.1080/1071576031000097490
19. Wybraniec, S.; Michałowski, T. New pathways of betanidin and betanin enzymatic oxidation studied by LC-DAD-ESI-MS/MS J. Agric. Food Chem. 2011, 59, 9612-9622 10.1021/jf2020107
20. Wybraniec, S.; Starzak, K.; Skopinska, A.; Nemzer, B.; Pietrzkowski, Z.; Michalowski, T. Studies on nonenzymatic oxidation mechanisms in neobetanin, betanin, and decarboxylated betanins J. Agric. Food Chem. 2013, 61, 6465-6476 10.1021/jf400818s
21. Wybraniec, S.; Stalica, P.; Spórna, A.; Nemzer, B.; Pietrzkowski, Z.; Michałowski, T. Antioxidant activity of betanidin: electrochemical study in aqueous media J. Agric. Food Chem. 2011, 59, 12163-12170 10.1021/jf2024769
22. Wybraniec, S. Formation of decarboxylated betacyanins in heated purified betacyanin fractions from red beet root (Beta vulgaris L.) monitored by LC-MS/MS J. Agric. Food Chem. 2005, 53, 3483-3487 10.1021/jf048088d
23. Wybraniec, S.; Mizrahi, Y. Generation of decarboxylated and dehydrogenated betacyanins in thermally treated purified fruit extract from purple pitaya (Hylocereus polyrhizus) monitored by LC-MS/MS J. Agric. Food Chem. 2005, 53, 6704-6712 10.1021/jf050700t
24. Herbach, K. M.; Stintzing, F. C.; Carle, R. Impact of thermal treatment on color and pigment pattern of red beet (Beta vulgaris L.) preparations J. Food Sci. 2004, 69, 491-498 10.1111/j.1365-2621.2004.tb10994.x
25. Herbach, K. M.; Stintzing, F. C.; Carle, R. Betalain stability and degradation-structural and chromatic aspects J. Food Sci. 2006, 71, R41-R50 10.1111/j.1750-3841.2006.00022.x
26. 13C NMR spectroscopic structural elucidation of new decarboxylated betacyanins Tetrahedron Lett. 2006, 47, 1725-1728 10.1016/j.tetlet.2006.01.046
27. Spórna-Kucab, A.; Ignatova, S.; Garrard, I.; Wybraniec, S. Versatile solvent systems for the separation of betalains from processed Beta vulgaris L. juice using counter-current chromatography J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2013, 941, 54-61 10.1016/j.jchromb.2013.10.001
28. Glassgen, W. E.; Metzger, J. W.; Heuer, S.; Strack, D. Betacyanins from fruits of Basella rubra Phytochemistry 1993, 33, 1525-1527 10.1016/0031-9422(93)85126-C
29. Kobayashi, N.; Schmidt, J.; Wray, V.; Schliemann, W. Formation and occurrence of dopamine-derived betacyanins Phytochemistry 2001, 56, 429-436 10.1016/S0031-9422(00)00383-6
30. Piattelli, M.; Impellizzeri, G. 2-Descarboxybetanidin, a minor betacyanin from Carpobrotus acinaciformis Phytochemistry 1970, 9, 2553-2556 10.1016/S0031-9422(00)85776-3
31. Dunkelblum, E.; Miller, H. E.; Dreiding, A. S. On the mechanism of decarboxylation of betanidine. A contribution to the interpretation of the biosynthesis of betalaines Helv. Chim. Acta 1972, 55, 642-648 10.1002/hlca.19720550239
32. Wybraniec, S. A method for identification of diastereomers of 2-decarboxy-betacyanins and 2,17-bidecarboxy-betacyanins in reversed phase HPLC Anal. Bioanal. Chem. 2007, 389, 1611-1621 10.1007/s00216-007-1550-2
33. Nemzer, B.; Pietrzkowski, Z.; Spórna, A.; Stalica, P.; Thresher, W.; Michałowski, T.; Wybraniec, S. Betalainic and nutritional profiles of pigment-enriched red beet root (Beta vulgaris L.) dried extracts Food Chem. 2011, 127, 42-53 10.1016/j.foodchem.2010.12.081
34. Gandía-Herrero, F.; Escribano, J.; García-Carmona, F. Characterization of the activity of tyrosinase on betanidin J. Agric. Food Chem. 2007, 55, 1546-1551 10.1021/jf062858z
35. Heuer, S.; Wray, V.; Metzger, J. W.; Strack, D. Betacyanins from flowers of Gomphrena globosa Phytochemistry 1992, 31, 1801-1807 10.1016/0031-9422(92)83151-N
36. Wybraniec, S.; Jerz, G.; Gebers, N.; Winterhalter, P. Ion-pair high speed countercurrent chromatography fractionation of a high-molecular weight variation of acyl-oligosaccharide linked betacyanins from purple bracts of Bougainvillea glabra J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2010, 878, 538-550 10.1016/j.jchromb.2009.12.029