Tetrahydro-beta-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers.
Tetrahydro-beta-carbolines are biologically active alkaloids that occur and accumulate in mammalian tissues, fluids, and brain, but their ultimate origin or biological role is still uncertain. Four tetrahydro-beta-carboline alkaloids: 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, 1-methyl-1,2,3,4-tetrahydro-beta-carboline, and 6-hydroxy-1-methyl-1,2,3,4-tetrahydro-beta-carboline, are found as naturally occurring substances in some fruit and fruit juices. These compounds occur in the microg/g level in those products, and a characteristic and distinct profile appears to exist depending on the type of fruit and juice involved. Thus, 1-methyl-1,2,3,4-tetrahydro-beta-carboline may appear in tomato, tomato juice, and kiwi; 6-hydroxy-1-methyl-1,2,3,4-tetrahydro-beta-carboline in bananas, pineapple, tomato, and their corresponding juices; and 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid in oranges and grapefruits, although it also occurred in most juices. Fruit-occurring tetrahydro-beta-carboline alkaloids acted as antioxidants and free radical scavengers in the ABTS assay when compared with ascorbic acid and Trolox. This suggests that tetrahydro-beta-carboline alkaloids might act as antioxidants when absorbed and accumulated in the body, contributing to the antioxidant effect of fruit products containing these compounds.
Herraiz
Tomas
T
Spanish Council for Scientific Research, Instituto de Fermentaciones Industriales, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain. therraiz@ifi.csic.es
Galisteo
Juan
J
D029042:Actinidia / Q000737:chemistry; D000470:Alkaloids / Q000032:analysis* / Q000737:chemistry; D031230:Ananas / Q000737:chemistry; D000975:Antioxidants / Q000032:analysis* / Q000737:chemistry; D052160:Benzothiazoles; D001628:Beverages / Q000032:analysis*; D002243:Carbolines / Q000032:analysis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002957:Citrus / Q000737:chemistry; D016166:Free Radical Scavengers / Q000032:analysis* / Q000737:chemistry; D005638:Fruit / Q000737:chemistry*; D018551:Solanum lycopersicum / Q000737:chemistry; D013058:Mass Spectrometry; D028521:Musa / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013451:Sulfonic Acids / Q000737:chemistry
D000470:Alkaloids; D000975:Antioxidants; D052160:Benzothiazoles; D002243:Carbolines; D016166:Free Radical Scavengers; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C009804:tryptoline