Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay.
Indoles are very common in the body and diet and participate in many biochemical processes. A total of twenty-nine indoles and analogs were examined for their properties as antioxidants and radical scavengers against 2,2'-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) ABTS*+ radical cation. With only a few exceptions, indoles reacted nonspecifically and quenched this radical at physiological pH affording ABTS. Indoleamines like tryptamine, serotonin and methoxytryptamine, neurohormones (melatonin), phytohormones (indoleacetic acid and indolepropionic acid), indoleamino acids like L-tryptophan and derivatives (N-acetyltryptophan, L-abrine, tryptophan ethyl ester), indolealcohols (tryptophol and indole-3-carbinol), short peptides containing tryptophan, and tetrahydro-beta-carboline (pyridoindole) alkaloids like the pineal gland compound pinoline, acted as radical scavengers and antioxidants in an ABTS assay-measuring total antioxidant activity. Their trolox equivalent antioxidant capacity (TEAC) values ranged from 0.66 to 3.9 mM, usually higher than that for Trolox and ascorbic acid (1 mM). The highest antioxidant values were determined for melatonin, 5-hydroxytryptophan, trp-trp and 5-methoxytryptamine. Active indole compounds were consumed during the reaction with ABTS*+ and some tetrahydropyrido indoles (e.g. harmaline and 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid ethyl ester) afforded the corresponding fully aromatic beta-carbolines (pyridoindoles), that did not scavenge ABTS*+. Radical scavenger activity of indoles against ABTS*+ was higher at physiological pH than at low pH. These results point out to structural compounds with an indole moiety as a class of radical scavengers and antioxidants. This activity could be of biological significance given the physiological concentrations and body distribution of some indoles.
Herraiz
Tomas
T
Spanish Council for Scientific Research (CSIC), Instituto de Fermentaciones Industriales, Juan de la Cierve 3, 28006, Madrid, Spain. therraiz@ifi.csic.es
Galisteo
Juan
J
D000975:Antioxidants / Q000737:chemistry* / Q000145:classification*; D052160:Benzothiazoles; D002412:Cations; D016166:Free Radical Scavengers / Q000145:classification* / Q000494:pharmacology*; D005609:Free Radicals / Q000037:antagonists & inhibitors / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013451:Sulfonic Acids / Q000037:antagonists & inhibitors* / Q000737:chemistry
D000975:Antioxidants; D052160:Benzothiazoles; D002412:Cations; D016166:Free Radical Scavengers; D005609:Free Radicals; D007211:Indoles; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid