Structural implications on color, fluorescence, and antiradical activity in betalains.
Betalains are water-soluble pigments with high antiradical capacity which bestow bright colors on flowers and fruits of most plants of the order Caryophyllales. They are classified as betacyanins, exhibiting a violet coloration, and betaxanthins, which exhibit yellow coloration. Traditionally, betalains have been defined as condensation products of betalamic acid with different amines and amino acids, but the implication of the pigment structure for their properties has not been investigated. This paper explores different structural features of the betalains, revealing the clues for the switch from yellow to violet color, and the loss of fluorescence. A relevant series of 15 betalain-related compounds (both natural and novel semisynthetic ones) is obtained and characterized by chromatography, UV-vis spectrophotometry, fluorescence, and electrospray ionization mass spectroscopy. Antiradical properties of individual pure compounds in a broad pH range are studied under the ABTS(*+) radical assay. Relevance of specific bonds is studied, and differences between betaxanthins and betacyanins are used to explore in depth the structure-antiradical activity relationships in betalains.
Gandía-Herrero
Fernando
F
Departamento de Bioquímica y Biología Molecular A, Facultad de Veterinaria, Universidad de Murcia, Espinardo, Murcia, Spain. fgandia@um.es
Escribano
Josefa
J
García-Carmona
Francisco
F
D052160:Benzothiazoles / Q000737:chemistry; D050858:Betalains / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003116:Color; D005453:Fluorescence; D016166:Free Radical Scavengers; D005609:Free Radicals / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry; D013451:Sulfonic Acids / Q000737:chemistry
D052160:Benzothiazoles; D016166:Free Radical Scavengers; D005609:Free Radicals; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D050858:Betalains
J Nat Prod. 2009 Jun;72(6):1142-6
19456119
Plant Physiol. 1999 Apr;119(4):1217-32
10198080
J Mass Spectrom. 2004 Jan;39(1):1-15
14760608
Food Addit Contam. 2006 Nov;23(11):1079-87
17071510
Phytochemistry. 2001 Sep;58(1):159-65
11524126
Free Radic Biol Med. 1999 May;26(9-10):1231-7
10381194
J Agric Food Chem. 2007 Feb 21;55(4):1546-51
17256962
Phytochem Anal. 2006 Jul-Aug;17(4):262-9
16910043
Phytochemistry. 1994 Oct;37(3):761-7
7765689
Planta. 2005 Nov;222(4):586-93
16177911
J Agric Food Chem. 2001 Nov;49(11):5178-85
11714300
Plant Physiol. 2005 May;138(1):421-32
15805475
Anal Bioanal Chem. 2007 Nov;389(5):1611-21
17786409
J Agric Food Chem. 2003 Apr 9;51(8):2288-94
12670172
J Agric Food Chem. 2008 Jul 23;56(14):5758-64
18578538
Phytochemistry. 2003 Feb;62(3):247-69
12620337
Plant J. 2008 Dec;56(6):963-74
18702669
J Agric Food Chem. 2002 Apr 10;50(8):2302-7
11929288
Plant Cell Physiol. 2009 May;50(5):1012-6
19366710
Life Sci. 2006 May 15;78(25):2872-88
16325868
Pharmacol Res. 2003 Feb;47(2):141-8
12543062
Phytochemistry. 2001 Mar;56(5):429-36
11261575
Z Naturforsch C J Biosci. 2002 Jul-Aug;57(7-8):640-4
12240990
J Agric Food Chem. 2002 Nov 6;50(23):6895-901
12405794
Eur J Pharmacol. 2009 Aug 1;615(1-3):223-7
19446548
J Agric Food Chem. 2001 Apr;49(4):1971-8
11308355
J Chromatogr A. 2005 Jun 17;1078(1-2):83-9
16007985
Free Radic Res. 2003 Jun;37(6):689-96
12868496