Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract.
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.
Ichikawa
Makoto
M
Healthcare Research Institute, Wakunaga Pharmaceutical Co., Ltd., 1624, Shimokotachi, Koda-cho, Takata-gun, Hiroshima, 739-1195, Japan.
Ryu
Kenjiro
K
Yoshida
Jiro
J
Ide
Nagatoshi
N
Yoshida
Susumu
S
Sasaoka
Takashi
T
Sumi
Shin-Ichiro
S
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D002243:Carbolines / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D016166:Free Radical Scavengers / Q000494:pharmacology; D005737:Garlic / Q000737:chemistry*; D006861:Hydrogen Peroxide; D015227:Lipid Peroxidation / Q000187:drug effects; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D009573:Nitrites / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry*; D013237:Stereoisomerism; D013997:Time Factors
D000975:Antioxidants; D002243:Carbolines; D016166:Free Radical Scavengers; D009573:Nitrites; D010936:Plant Extracts; C009804:tryptoline; D006861:Hydrogen Peroxide