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Tetrahydro-beta-carboline derivatives in aged garlic extract show antioxidant properties.
J Nutr. 2006 03; 136(3 Suppl):726S-731S.JN

Abstract

This study used the hydroden peroxide scavenging assay to investigate antioxidant chemical constituents derived and separated from aged garlic extract, a unique garlic extract produced by soaking sliced garlic in an aqueous ethanol solution for >10 mo. Four types of 1, 2, 3, 4-tetrahydro-beta-carboline derivatives (THbetaCs); 1-methyl-1, 2, 3, 4-tetrahydro-beta-carboline-3-carboxylic acid, and 1-methyl-1, 2, 3, 4-tetrahydro-beta-carboline-1, 3-dicarboxylic acid (MTCdiC), from both diastereoisomers, were isolated and identified by use of liquid chromatography-mass spectrometry. All these compounds indicate strong hydrogen peroxide scavenging activities and inhibit 2, 2'-azobis(2-amidinopropane) hydrochloride-induced lipid peroxidation. Particularly, (1S, 3S)-MTCdiC had the most potent hydrogen peroxide scavenging activity, more than ascorbic acid. The (1R, 3S)- and (1S, 3S)-MTCdiC at 50-100 micromol/L and 10-100 micromol/L inhibited LPS-induced nitrite production. Interestingly, THbetaCs were not detected in raw garlic and other processed garlic preparations, but they were generated and increased during the natural aging garlic extraction process. These data suggest that THbetaCs, which are formed during the natural aging process, are potent antioxidants in aged garlic extract and thus may be useful for the prevention of diseases associated with oxidative damage.

Authors+Show Affiliations

Healthcare Research Institute, Wakunaga Pharmaceutical Co. Ltd., and Department of Molecular Biotechnology, Graduate School of Advanced Sciences of Matter, Hiroshima University, Hiroshima 739-8530, Japan. ichikawa_m@wakunaga.co.jpNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16484551

Citation

Ichikawa, Makoto, et al. "Tetrahydro-beta-carboline Derivatives in Aged Garlic Extract Show Antioxidant Properties." The Journal of Nutrition, vol. 136, no. 3 Suppl, 2006, 726S-731S.
Ichikawa M, Yoshida J, Ide N, et al. Tetrahydro-beta-carboline derivatives in aged garlic extract show antioxidant properties. J Nutr. 2006;136(3 Suppl):726S-731S.
Ichikawa, M., Yoshida, J., Ide, N., Sasaoka, T., Yamaguchi, H., & Ono, K. (2006). Tetrahydro-beta-carboline derivatives in aged garlic extract show antioxidant properties. The Journal of Nutrition, 136(3 Suppl), 726S-731S. https://doi.org/10.1093/jn/136.3.726S
Ichikawa M, et al. Tetrahydro-beta-carboline Derivatives in Aged Garlic Extract Show Antioxidant Properties. J Nutr. 2006;136(3 Suppl):726S-731S. PubMed PMID: 16484551.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tetrahydro-beta-carboline derivatives in aged garlic extract show antioxidant properties. AU - Ichikawa,Makoto, AU - Yoshida,Jiro, AU - Ide,Nagatoshi, AU - Sasaoka,Takashi, AU - Yamaguchi,Hiroyuki, AU - Ono,Kazuhisa, PY - 2006/2/18/pubmed PY - 2006/5/4/medline PY - 2006/2/18/entrez SP - 726S EP - 731S JF - The Journal of nutrition JO - J Nutr VL - 136 IS - 3 Suppl N2 - This study used the hydroden peroxide scavenging assay to investigate antioxidant chemical constituents derived and separated from aged garlic extract, a unique garlic extract produced by soaking sliced garlic in an aqueous ethanol solution for >10 mo. Four types of 1, 2, 3, 4-tetrahydro-beta-carboline derivatives (THbetaCs); 1-methyl-1, 2, 3, 4-tetrahydro-beta-carboline-3-carboxylic acid, and 1-methyl-1, 2, 3, 4-tetrahydro-beta-carboline-1, 3-dicarboxylic acid (MTCdiC), from both diastereoisomers, were isolated and identified by use of liquid chromatography-mass spectrometry. All these compounds indicate strong hydrogen peroxide scavenging activities and inhibit 2, 2'-azobis(2-amidinopropane) hydrochloride-induced lipid peroxidation. Particularly, (1S, 3S)-MTCdiC had the most potent hydrogen peroxide scavenging activity, more than ascorbic acid. The (1R, 3S)- and (1S, 3S)-MTCdiC at 50-100 micromol/L and 10-100 micromol/L inhibited LPS-induced nitrite production. Interestingly, THbetaCs were not detected in raw garlic and other processed garlic preparations, but they were generated and increased during the natural aging garlic extraction process. These data suggest that THbetaCs, which are formed during the natural aging process, are potent antioxidants in aged garlic extract and thus may be useful for the prevention of diseases associated with oxidative damage. SN - 0022-3166 UR - https://www.unboundmedicine.com/medline/citation/16484551/Tetrahydro_beta_carboline_derivatives_in_aged_garlic_extract_show_antioxidant_properties_ L2 - https://academic.oup.com/jn/article-lookup/doi/10.1093/jn/136.3.726S DB - PRIME DP - Unbound Medicine ER -