Tags

Type your tag names separated by a space and hit enter

L-tryptophan reacts with naturally occurring and food-occurring phenolic aldehydes to give phenolic tetrahydro-beta-carboline alkaloids: activity as antioxidants and free radical scavengers.
J Agric Food Chem. 2003 Apr 09; 51(8):2168-73.JA

Abstract

The reaction between the essential amino acid l-tryptophan and flavoring or naturally occurring phenyl and phenolic aldehydes was studied, and the alkaloidal reaction products were characterized by NMR and HPLC-MS. Benzaldehyde, vanillin, syringaldehyde, salicylaldehyde, and anisaldehyde condensed with l-tryptophan in aqueous-acidic media affording the corresponding phenolic tetrahydro-beta-carboline-3-carboxylic acid as two diastereoisomers, 1S,3S-cis and 1R,3S-trans. With the exception of benzaldehyde, the rest of the aldehydes needed heating conditions (70 degrees C) to significantly form tetrahydro-beta-carbolines over time with the cyclization highly favored at low pH. This suggests a likely formation of these compounds under conditions that may occur in foods, food processing, or cooking. The new phenolic tetrahydro-beta-carboline alkaloids were assayed, for the first time, for their activity as free radical scavengers and antioxidants and showed good antioxidant properties with Trolox equivalent antioxidant capacity (TEAC) values much higher than those of ascorbic acid and the water soluble vitamin E analogue, Trolox, in the 2,2'-azinobis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) assay.

Authors+Show Affiliations

Instituto de Fermentaciones Industriales, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. therraiz@ifi.csic.esNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

12670151

Citation

Herraiz, Tomas, et al. "L-tryptophan Reacts With Naturally Occurring and Food-occurring Phenolic Aldehydes to Give Phenolic Tetrahydro-beta-carboline Alkaloids: Activity as Antioxidants and Free Radical Scavengers." Journal of Agricultural and Food Chemistry, vol. 51, no. 8, 2003, pp. 2168-73.
Herraiz T, Galisteo J, Chamorro C. L-tryptophan reacts with naturally occurring and food-occurring phenolic aldehydes to give phenolic tetrahydro-beta-carboline alkaloids: activity as antioxidants and free radical scavengers. J Agric Food Chem. 2003;51(8):2168-73.
Herraiz, T., Galisteo, J., & Chamorro, C. (2003). L-tryptophan reacts with naturally occurring and food-occurring phenolic aldehydes to give phenolic tetrahydro-beta-carboline alkaloids: activity as antioxidants and free radical scavengers. Journal of Agricultural and Food Chemistry, 51(8), 2168-73.
Herraiz T, Galisteo J, Chamorro C. L-tryptophan Reacts With Naturally Occurring and Food-occurring Phenolic Aldehydes to Give Phenolic Tetrahydro-beta-carboline Alkaloids: Activity as Antioxidants and Free Radical Scavengers. J Agric Food Chem. 2003 Apr 9;51(8):2168-73. PubMed PMID: 12670151.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - L-tryptophan reacts with naturally occurring and food-occurring phenolic aldehydes to give phenolic tetrahydro-beta-carboline alkaloids: activity as antioxidants and free radical scavengers. AU - Herraiz,Tomas, AU - Galisteo,Juan, AU - Chamorro,Cristina, PY - 2003/4/3/pubmed PY - 2003/5/3/medline PY - 2003/4/3/entrez SP - 2168 EP - 73 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 51 IS - 8 N2 - The reaction between the essential amino acid l-tryptophan and flavoring or naturally occurring phenyl and phenolic aldehydes was studied, and the alkaloidal reaction products were characterized by NMR and HPLC-MS. Benzaldehyde, vanillin, syringaldehyde, salicylaldehyde, and anisaldehyde condensed with l-tryptophan in aqueous-acidic media affording the corresponding phenolic tetrahydro-beta-carboline-3-carboxylic acid as two diastereoisomers, 1S,3S-cis and 1R,3S-trans. With the exception of benzaldehyde, the rest of the aldehydes needed heating conditions (70 degrees C) to significantly form tetrahydro-beta-carbolines over time with the cyclization highly favored at low pH. This suggests a likely formation of these compounds under conditions that may occur in foods, food processing, or cooking. The new phenolic tetrahydro-beta-carboline alkaloids were assayed, for the first time, for their activity as free radical scavengers and antioxidants and showed good antioxidant properties with Trolox equivalent antioxidant capacity (TEAC) values much higher than those of ascorbic acid and the water soluble vitamin E analogue, Trolox, in the 2,2'-azinobis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) assay. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/12670151/L_tryptophan_reacts_with_naturally_occurring_and_food_occurring_phenolic_aldehydes_to_give_phenolic_tetrahydro_beta_carboline_alkaloids:_activity_as_antioxidants_and_free_radical_scavengers_ L2 - https://doi.org/10.1021/jf0210066 DB - PRIME DP - Unbound Medicine ER -