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Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract.
Biofactors. 2002; 16(3-4):57-72.B

Abstract

1,2,3,4-Tetrahydro-beta-carboline derivatives (THbetaCs) are formed through Pictet-Spengler chemical condensation between tryptophan and aldehydes during food production, storage and processing. In the present study, in order to identify the antioxidants in aged garlic extract (AGE), we fractionated it and identified four THbetaCs; 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acids (MTCC) and 1-methyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid (MTCdiC) in both diastereoisomers using liquid chromatography mass spectrometry (LC-MS). Interestingly, these compounds were not detected in raw garlic, but the contents increased during the natural aging process of garlic. In in vitro assay systems, all of these compounds have shown strong hydrogen peroxide scavenging activities. (1S, 3S)-MTCdiC was found to be stronger than the common antioxidant, ascorbic acid. MTCC and MTCdiC inhibited AAPH-induced lipid peroxidation. Both MTCdiCs also inhibited LPS-induced nitrite production from murine macrophages at 10-100 microM. Our data suggest that these compounds are potent antioxidants in AGE, and thus may be useful for prevention of disorders associated with oxidative stress.

Authors+Show Affiliations

Healthcare Research Institute, Wakunaga Pharmaceutical Co., Ltd., 1624, Shimokotachi, Koda-cho, Takata-gun, Hiroshima, 739-1195, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

14530594

Citation

Ichikawa, Makoto, et al. "Antioxidant Effects of Tetrahydro-beta-carboline Derivatives Identified in Aged Garlic Extract." BioFactors (Oxford, England), vol. 16, no. 3-4, 2002, pp. 57-72.
Ichikawa M, Ryu K, Yoshida J, et al. Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract. Biofactors. 2002;16(3-4):57-72.
Ichikawa, M., Ryu, K., Yoshida, J., Ide, N., Yoshida, S., Sasaoka, T., & Sumi, S. (2002). Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract. BioFactors (Oxford, England), 16(3-4), 57-72.
Ichikawa M, et al. Antioxidant Effects of Tetrahydro-beta-carboline Derivatives Identified in Aged Garlic Extract. Biofactors. 2002;16(3-4):57-72. PubMed PMID: 14530594.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract. AU - Ichikawa,Makoto, AU - Ryu,Kenjiro, AU - Yoshida,Jiro, AU - Ide,Nagatoshi, AU - Yoshida,Susumu, AU - Sasaoka,Takashi, AU - Sumi,Shin-Ichiro, PY - 2003/10/8/pubmed PY - 2004/4/21/medline PY - 2003/10/8/entrez SP - 57 EP - 72 JF - BioFactors (Oxford, England) JO - Biofactors VL - 16 IS - 3-4 N2 - 1,2,3,4-Tetrahydro-beta-carboline derivatives (THbetaCs) are formed through Pictet-Spengler chemical condensation between tryptophan and aldehydes during food production, storage and processing. In the present study, in order to identify the antioxidants in aged garlic extract (AGE), we fractionated it and identified four THbetaCs; 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acids (MTCC) and 1-methyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid (MTCdiC) in both diastereoisomers using liquid chromatography mass spectrometry (LC-MS). Interestingly, these compounds were not detected in raw garlic, but the contents increased during the natural aging process of garlic. In in vitro assay systems, all of these compounds have shown strong hydrogen peroxide scavenging activities. (1S, 3S)-MTCdiC was found to be stronger than the common antioxidant, ascorbic acid. MTCC and MTCdiC inhibited AAPH-induced lipid peroxidation. Both MTCdiCs also inhibited LPS-induced nitrite production from murine macrophages at 10-100 microM. Our data suggest that these compounds are potent antioxidants in AGE, and thus may be useful for prevention of disorders associated with oxidative stress. SN - 0951-6433 UR - https://www.unboundmedicine.com/medline/citation/14530594/Antioxidant_effects_of_tetrahydro_beta_carboline_derivatives_identified_in_aged_garlic_extract_ L2 - https://content.iospress.com/openurl?genre=article&issn=0951-6433&volume=16&issue=3-4&spage=57 DB - PRIME DP - Unbound Medicine ER -