Antioxidant effects of tetrahydro-β-carboline derivatives identified in aged garlic extract

BioFactors

Volumn 16, Issue 3-4, 2002, Pages 57-72

  Ichikawa, Makoto ^a   Ryu, Kenjiro ^a   Yoshida, Jiro ^a   Ide, Nagatoshi ^a   Yoshida, Susumu ^a   Sasaoka, Takashi ^a   Sumi, Shin Ichiro ^a  

^a WAKUNAGA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Aged garlic extract; Antioxidant; LC MS; Maillard reaction products; Tetrahydro carboline derivatives

Indexed keywords

1 METHYL 1,2,3,4 TETRAHYDRO BETA CARBOLINE 1,3 DICARBOXYLIC ACID; 1,2,3,4 TETRAHYDRO 1 METHYL BETA CARBOLINE 3 CARBOXYLIC ACID; ANTIOXIDANT; ASCORBIC ACID; GARLIC EXTRACT; HYDROGEN PEROXIDE; LIPOPOLYSACCHARIDE; NITRITE; SCAVENGER; TRYPTOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL FRACTIONATION; COMPARATIVE STUDY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG EFFECT; DRUG IDENTIFICATION; DRUG POTENCY; IN VITRO STUDY; MACROPHAGE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ALLIUM SATIVUM; ANIMALIA; MURINAE;

EID: 0141922866     PISSN: 09516433     EISSN: None     Source Type: Journal    
DOI: 10.1002/biof.5520160302     Document Type: Article

References (39)

1. W.M. Whaley and T.R. Govindachari, The Pictet-Spengler synthesis of tetrahydroisoquinolines and related compounds, Org. React. (N.Y.) 6 (1951), 151-190.
2. H. Tsuchiya, M. Sato and I. Watanabe, Antiplatelet activity of soy sauce as functional seasoning, J Agric Food Chem 47 (1999), 4167-4174.
3. T. Herraiz, Occurrence of tetrahydro-β-carboline-3-carboxylic acids in commercial foodstuffs, J Agric Food Chem 44 (1996), 3057-3065.
4. B. Gutsche and M. Herderich, HPLC-MS/MS profiling of tryptophan-derived alkaloids in food: identification of tetrahydro-β-carboline dicarboxylic acids, J Agric Food Chem 45 (1997), 2458-2462.
5. B. Gutsche and M. Herderich, High-performance liquid chromatography-electrospray ionisation-tandem mass spectrometry for the analysis of 1,2,3,4-tetrahydro-β-carboline derivatives, J Chromatogr A 767 (1997), 101-106.
6. N. Arutselvan, S. Gopalan, V.G. Kulkarni and K. Balakrishna, Antioxidant activity of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, Arzneim-Forsch/Drug Res 49 (1999), 729-731.
7. K. Pari, C.S. Sundari, S. Chandani and D. Balasubramanian, β-Carbolines that accumulate in human tissues may serve a protective role against oxidative stress, J Biol Chem 275 (2000), 2455-2462.
8. D.J. McKenna and G.H.N. Towers, Biochemistry and pharmacology of tryptamines and β-carbolines: A minireview, J Psychoact Drugs 16 (1984), 347-358.
9. H. Rommelspacher, T. May and B. Salewski, Harman (1-methyl-β -carboline) is a natural inhibitor of monoamine oxidase type A in rats, Eur J Pharmacol 252 (1994), 51-59.
10. E. Block, The organosulfur chemistry of the genus Allium- implications for the organic chemistry of sulfur, Angew Chem Int Ed Engl 31 (1992), 1135-1178.
11. J. Imai, N. Ide, S. Nagae, T. Moriguchi, H. Mastuura and Y. Itakura, Antioxidant and radical scavenging effects of aged garlic extract and its constituents, Planta Med 60 (1994), 417-420.
12. N. Ide and B.H.S. Lau, Garlic compounds protect vascular endothelial cells from oxidized low density lipoprotein-induced injury, J Pharm Pharmacol 49 (1997), 908-911.
13. N. Ide and B.H.S. Lau, Aged garlic extract attenuates intracellular oxidative stress, Phytomed 6 (1999), 125-131.
14. H. Amagase and J.A. Milner, Impact of various sources of garlic and their constituents on 7,12-dimethylbenz(a)anthracene binding to mammary cell DNA, Carcinogenesis 14 (1993), 1627-1631.
15. J.L. Efendy, D.L. Simmons, G.R. Campbell and J.H. Campbell, The effect of the aged garlic extract, Kyolic on the development of experimental atherosclerosis, Atherosclerosis 132 (1997), 37-42.
16. K. Rahmann and D. Billington, Dietary supplementation with aged garlic extract inhibits ADP-induced platelet aggregation in humans, J Nutr 130 (2000), 2662-2665.
17. M. Steiner and W. Li, Aged garlic extract, a modulator of cardiovascular risk factors: a dose-finding study on the effects of AGE on platelet functions, J Nutr 131 (2001), 980S-984S.
18. T. Moriguchi, H. Saito and N. Nishiyama, Aged garlic extract prolongs longevity and improves spatial memory deficit in senescence-accelerated mouse, Biol Pharm Bull 19 (1996), 305-307.
19. K. Ryu, N. Ide, H. Matsuura and Y. Itakura, Nα -(1-deoxy-D-fructos-1-yl)-L-arginine, an antioxidant compound identified in aged garlic extract, J Nutr 131 (2001), 972S-976S.
20. J.M. Bobbitt and J.P. Willis, Electrochemistry of natural products. 7. Oxidative decarboxylation of some tetrahydro-β-carboxylic acids, J Org Chem 45 (1980), 1978-1984.
21. G. Okamoto, F. Hayase and H. Kato, Scavenging of active oxygen species by glycated proteins, Biosci Biotech Biochem 56 (1992), 928-931.
22. W.A. Pryor, Comparison of the efficiencies of several natural and synthetic antioxidants in aqueous sodium dodecyl sulphate micelle solutions, J Am Chem Soc 110 (1998), 2224-2229.
23. N. Ide, H. Matsuura and Y. Itakura, Scavenging effect of aged garlic extract and its constituents on active oxygen species, Phytother Res 10 (1996), 340-341.
24. V.M. Dirsch, A.K. Kiemer, H. Wagner and A.M. Vollmar, Effect of allicin and ajoene, two compounds of garlic, on inducible nitric oxide synthase, Atherosclerosis 139 (1998), 333-339.
25. T.R. Bosin, S. Krogh and D. Mais, Identification and quantitation of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in beer, J Agric Food Chem 34 (1986), 843-847.
26. T. Herraiz and C.S. Ough, Chemical and technological factors determining tetrahydro-β-carboline-3-carboxylic acid content in fermented alcoholic bevarages, J Agric Food Chem 41 (1993), 959-964.
27. T. Herraiz, Z. Huang and C.S. Ough, 1,2,3,4-Tetrahydro-β -carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β -carboline-3-carboxylic acid in wine, J Agric Food Chem 41 (1993), 455-459.
28. L.D. Lawson, The composition and chemistry of garlic cloves and processed garlic, in: Garlic- the science and therapeutic application of Allium sativum L. and related species, H.P. Koch and L.D. Lawson, eds, Boltimore: Williams & Wilkins, 2000, pp. 37-107.
29. H. Matsuura, Garlic chemistry, in: Garlic Science, H. Saito, ed., Tokyo: Asakura Publishing Company, 2000, pp. 93-122.
30. A. Wnorowski and V.A. Yaylayan, Influence of pyrolytic aqueous-phase reactions on the mechanism of formation of Maillard products, J Agric Food Chem 48 (2000), 3549-3554.
31. L. Spatz, Introduction, in: Biological consequences of oxidative stress, L. Spatz and A. Bloom, ed., New York: Oxford University Press, 1992, pp. 3-22.
32. P.E. Chabrier, C. Demerle Pallardy and M. Auget, Nitric oxide synthases: targets for therapeutic strategies in neurological diseases, Cell Mol Life Sci 55 (1999), 1029-1035.
33. D.W. Crawford and D.H. Blankenhom, Arterial wall oxygenation, oxyradicals and atherosclerosis, Atherosclerosis 89 91-108.
34. T. Yamasaki, L. Li and B.H.S. Lau, Garlic compounds protect vascular endothelial cells from hydrogen peroxide-induced oxidant injury, Phytother Res 8 (1994), 408-412.
35. C.K. Sen and L. Packer, Antioxidant and redox regulation of gene transcription, FASEB J 10 (1996), 709-720.
36. Z. Geng, Y. Rong and B.H.S. Lau, S-Allylcysteine inhibits activation of nuclear factor kappa B in human T cells, Free Radic. Biol. Med. 23 (1997), 345-350.
37. H. Ischiropoulos, L. Zhu and J.S. Beckman, Peroxinitrite formation from macrophage-derived nitric oxide, Arch Biochem Biophys 298 (1992), 446-451.
38. D.D. Rees, S. Cellek, R.M. Palmer and S. Moncada, Dexamethasone prevents the induction by endotoxin of a nitric oxide synthase and the associated effects on vascular tone: an insight into endotoxin shock, Biochem Biophys Res Commun 173 (1990), 541-547.
39. B.G. Lee, S.H. Kim, O.P. Zee, K.R. Lee, H.y. Lee, J.W. Han and H.W. Lee, Suppression of inducible nitric oxide synthase expression in RAW 264.7 macrophages by two β-carboline alkaloids extracted from Melia azedarach, Eur J Pharmacol 406 (2000), 301-309.