Plant Foods for Human Nutrition

, Volume 61, Issue 4, pp 175–178 | Cite as

Increased Level of Tetrahydro-β-Carboline Derivatives in Short-Term Fermented Garlic



In our previous study [1], we found that relatively short-term spontaneous fermentation (40 days at 60–70°C, 85–95% relative humidity) potentiates anti-oxidative properties of garlic, in which scavenging activity against hydrogen peroxide was included. Since tetrahydro-β-carboline derivatives (THβCs) that possess hydrogen peroxide scavenging activity have recently been identified in aged garlic extract, THβCs were quantitatively analyzed with liquid chromatography-mass spectrometry (LC-MS). (1R, 3S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCC) and (1S, 3S)-MTCC were found in the fermented garlic extract whereas only trace levels of MTCCs were detected in the row garlic extract. Therefore, it is suggested that relatively short-term fermentation potentiates scavenging activity of garlic against hydrogen peroxide by forming THβCs, especially MTCCs.

Key words

Garlic Tetrahydro-β-carboline derivatives Hydrogen peroxide scavenging activity 


  1. 1.
    Sato E, Kohno M, Hamano H, Niwano Y (in press) Increased anti-oxidative potency of garlic by spontaneous short-term fermentation. Plant Foods Hum Nutr.Google Scholar
  2. 2.
    Dorant E, Van Den Brandt PA, Goldbohm RA, Hermus RJ, Sturmans F (1993) Garlic and its significance for the prevention of cancer in humans: A critical view. Br J Cancer 67: 424–429.Google Scholar
  3. 3.
    Kleijnen J, Knipschild P, Terriet G (1989) Garlic, onions and cardiovascular risk factors. A review of the evidence from human experiments with emphasis on commercially available preparations. Br J Clin Pharmacol 28: 535–544.Google Scholar
  4. 4.
    Nakagawa S, Kasuga S, Matsuura H (1989) Prevention of liver damage by aged garlic extract. Phytotherapy Res 3: 50–53.CrossRefGoogle Scholar
  5. 5.
    Pal R, Vaiphei K, Sikander A, Singh K, Rana SV (2006) Effect of garlic on isoniazid and rifampicin-induced hepatic injury in rats. World J Gastroenterol 12: 636–639.Google Scholar
  6. 6.
    Moriguchi T, Takashina K, Chu P, Saito H, Nishiyama N (1994) Prolongation of life span and improved learning in the senescence accelerated mouse produced by aged garlic extract. Biol Pharm Bull 17: 1589–1594.Google Scholar
  7. 7.
    Rietz B, Isensee H, Strobach H, Makdessi S, Jacob R (1993) Cardioprotective actions of wild garlic (Allium ursinum) in ischemia and reperfusion. Mol Cell Biochem 119: 143–150.CrossRefGoogle Scholar
  8. 8.
    Numagami Y, Suto S, Ohnishi ST (1996) Attenuation of rat ischemic brain damage by aged garlic extract: a possible protecting mechanism as antioxidants. Neurochemistry Int 29: 135–143.CrossRefGoogle Scholar
  9. 9.
    Ide N, Matsuura H, Itakura Y (1996) Scavenging effect of aged garlic extract and its constituents on active oxygen species. Phytotherapy Res 10: 340–341.CrossRefGoogle Scholar
  10. 10.
    Imai J, Ide N, Nagae T, Moriguchi H, Matsuura H, Itakura Y (1994) Antioxidant and radical scavenging effects of aged garlic extract and its constituents. Planta Med 60: 417–420.Google Scholar
  11. 11.
    Ide N, Lau BHS (1997) Garlic compounds protect vascular endothelial cells from oxidized low density lipoprotein-induced injury. J Pharm Pharmacol 49: 908–911.Google Scholar
  12. 12.
    Ide N, Lau BHS (1999) Aged garlic extract attenuates intracellular oxidative stress. Phytomed 6: 125–131.Google Scholar
  13. 13.
    Ichikawa M, Ryu K, Yoshida J, Ide N, Yoshida S, Sasaoka T, Sumi SI (2002) Antioxidant effects of tetrahydro-β-carboline derivatives identified in aged garlic extract. Biofactors 16: 57–72.Google Scholar
  14. 14.
    Ichikawa M, Yoshida J, Ide N, Sasaoka T, Yamaguchi H, Ono K (2006) Tetrahydro-β-Carboline Derivatives in Aged Garlic Extract Show Antioxidant Properties. J Nutr 136: 726S–731S.Google Scholar
  15. 15.
    Tsuchiya Y, Sato M, Watanabe I (1999) Antiplatelet activity of soy sauce as functional seasoning. J Agric Food Chem 47: 4167–4174.CrossRefGoogle Scholar
  16. 16.
    Bosin TR, Krogh S, Mais D (1986) Identification and quantification of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in beer and wine. J Agric Food Chem 34: 843–847.CrossRefGoogle Scholar
  17. 17.
    Herraiz T, Ough CS (1993) Chemical and technological factors determining tetrahydro-β-carboline-3-carboxylic acid content in fermented alcoholic beverages. J Agric Food Chem 41: 959–964.CrossRefGoogle Scholar
  18. 18.
    Herraiz T, Huang Z, Ough CS (1993) 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in wines. J Agric Food Chem 41: 455–459.CrossRefGoogle Scholar
  19. 19.
    Ozawa Y, Uda Y, Matsuoka H, Abe M, Kawakishi S, Osawa T (1999) Occurrence of stereoiosmers of 1-(2′-pyrrolidinethione-3′-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in fermented radish roots and their different mutagenic properties. Biosci Biotechnol Biochem 63: 216–219.CrossRefGoogle Scholar
  20. 20.
    Herraiz T (2000) Tetrahydro-β-carboline-3-carboxylic acid compounds in fish and meat: possible precursors of co-mutagenic β-carbolines norharman and harman in cooked foods. Food Addit Contam 17: 859–866.CrossRefGoogle Scholar
  21. 21.
    Herraiz T, Papavergou E (2004) Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-β-carbolines in commercial sausages. J Agric Food Chem 52: 2652–2658.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  1. 1.New Industry Creation Hatchery CenterTohoku UniversitySendaiJapan
  2. 2.Research Center for Functional Food MaterialsSunny Health Co., Ltd., Saito Biotechnology IncubatorIbaraki, OsakaJapan

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