3-(Allyltrisulfanyl)-2-aminopropanoic acid, a novel nonvolatile water-soluble antimicrobial sulfur compound in heated garlic

Journal of Medicinal Food

Volumn 13, Issue 5, 2010, Pages 1247-1253

  Kang, Seung Sik ^a   Lim, Dong Ryul ^a   Kyung, Kyu Hang ^a  

^a Sejong University   (South Korea)

Author keywords

allicin; alliin; antimicrobial compound; heated garlic

Indexed keywords

3 (ALLYLTRISULFANYL) 2 AMINOPROPANOIC ACID; ALLICIN; ALLIIN; ANTIINFECTIVE AGENT; CYSTEINE; GARLIC EXTRACT; PROPIONIC ACID DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; FOURIER TRANSFORM MASS SPECTROMETRY; GARLIC; HEATING; INFRARED SPECTROSCOPY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL;

ANTI-INFECTIVE AGENTS; BACTERIA; BETA-ALANINE; GARLIC; HOT TEMPERATURE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SULFHYDRYL COMPOUNDS; VOLATILIZATION; WATER; YEASTS;

ALLIUM SATIVUM;

EID: 77956563642     PISSN: 1096620X     EISSN: None     Source Type: Journal    
DOI: 10.1089/jmf.2010.1059     Document Type: Article

References (26)

1. Stoll A, Seebeck E: Chemical investigation of alliin, the specific principle of garlic. Adv Enzymol 1951;11:377-400.
2. Lawson LD: The composition and chemistry of garlic cloves and processed garlic. In: Garlic. The Science and Therapeutic Application of Allium sativum L. and Related Species (Koch HP, Lawson LD, eds.). Williams & Wilkins, Baltimore, 1996, pp. 37-107.
3. Kyung KH, Kim MH, Park MS, Kim YS: Alliinase-independent inhibition of Staphylococcus aureus B33 by heated garlic. J Food Sci 2002;67:780-785.
4. Choi JH, Kyung KH: Allyl alcohol is the sole antiyeast compound in heated garlic extract. J Food Sci 2005;70:305-309.
5. Kim EH, Chung IS, Kyung KH: Antimicrobial activity of garlic extract heated under different conditions, time of heating and pH. Food Sci Biotechnol 2009;18:771-775.
6. Kim JW, Huh JE, Kyung SH, Kyung KH: Antimicrobial activity of alk(en)yl sulfides found in essential oils of garlic and onion. Food Sci Biotechnol 2004;13:235-239.
7. Chung I, Chae KY, Kyung KH: Thermal generation and antimicrobial activity of unusual heterocyclic sulfur compounds in garlic. Food Sci Biotechnol 2008;17:1032-1037.
8. Ferary S, Thibot E, Auger J: Direct analysis of odors emitted by freshly cut Allium using combined high-performance liquid chromatography and mass spectrometry. Rapid Commun Mass Spectrom 1996;10:1327-1332.
9. Sundaresan S, Subramanian P: Prevention of N-nitroso-diethylamine-induced hepatocarcinogenesis by S-allylcysteine. Mol Cell Biochem 2008;310:209-214.
10. Howard EW, Ling M-T, Chua CW, Cheung HW, Wang X, Wong YC: Garlic-derived S-allylmercaptocysteine is a novel in vivo antimetastatic agent for androgen-independent prostate cancer. Clin Cancer Res 2007;13:1847-1856.
11. Shirin H, Pinto JT, Kawabata Y, Soh J-W, Delohery T, Moss SF, Murty V, Rivlin RS, Holt PR, Weinstein IB: Antiproliferative effects of S-allylmercaptocysteine on colon cancer cells when tested alone or in combination with sulindac sulfide. Cancer Res 2001;61:725-731.
12. Nakagawa S, Kasuga S, Matsuura H: Prevention of liver damage by aged garlic extract and its components in mice. Phytother Res 1989;3:50-53.
13. Pinto JT, Rivlin RS: Antiproliferative effects of Allium derivatives from garlic. J Nutr 2001;131(3S):1058S-1060S.
14. Chu Q, Lee DTW, Tsao SW, Wang X, Wong YC: S-Allylcys-teine, a water-soluble garlic derivative, suppresses the growth of a human androgen-independent prostate cancer xerograft, CWR22R, under in vivo conditions. BJU Int 2006;99:925-932.
15. Pinto JT, Qiao C, Xing J, Rivlin RS, Protomacastro ML, Weissler ML, Tao Y, Thaler H, Heston WDW: Effects of garlic thioallyl derivatives on growth, glutathione concentration, and polyamine formation of human prostate carcinoma cells in culture. Am J Clin Nutr 1997;66:398-405.
16. 2-terminal kinase 1 activation. Cancer Res 2003;63: 6825-6837.
17. Pedraza-Chaverrí J, Barrera D, Maldonado PD, Chirino YI, Macías-Ruvalcaba N, Medina-Campos ON, Castro L, Salcedo MI, Hernández-Pando R: S-Allylmercaptocysteine scavenges hy-droxyl radical and singlet oxygen in vitro and attenuates genta-micin-induced oxidative and nitrosative stress and renal damage in vivo. BMC Clin Pharmacol 2004;4:5.
18. Medina-Campos ON, Barrera D, Segoviano-Murillo S, Rocha D, Maldonado PD, Mendoza-Patino N, Pedraza-Chaverri J: S-Allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK1 cells of potassium dichromate-induced toxicity. Food Chem Toxicol 2007;45:2030-2039.
19. Pérez-Sereriano F, Salvatierra-Sánchez R, Rodríguez-Pérez M, Cuevas-Martínez EY, Guevara J, Limón D, Maldonado PD, Medina-Campos ON, Pedraza-Chaverrí J, Santamaría A: S-Allylcysteine prevents amyloid-b peptide-induced oxidative stress in rat hippocampus and ameliorates learning deficits. Eur J Pharmacol 2004;489:197-202.
20. Hatono S, Jimenez A, Wargovich M: Chemopreventive effect of S-allylcysteine and its relationship to the detoxification enzyme glutathione S-transferase. Carcinogenesis 1996;17: 1041-1044.
21. Cavallito CJ, Buck JS, Suter CM: Allicin, the antibacterial principle of Allium sativum. II. Determination of the chemical structure. J Am Chem Soc 1944;66:1952-1954.
22. Small LD, Bailey JH, Cavallito CJ: Alkyl thiosulfinates. J Am Chem Soc 1947;69:1710-1713.
23. Cavallito CJ, Bailey JH: Allicin, the antibacterial principle of Allium sativum. I. Isolation, physical properties and antimicrobial action. J Am Chem Soc 1944;66:1950-1951.
24. Kyung KH, Fleming HP: S-Methyl-l-cysteine sulfoxide as the precursor of methyl methanethiosulfinate, the principal antibacterial compound in cabbage. J Food Sci 1994;59:350-355.
25. Hageman GJ, van Herwinen MH, Schilderman PA, Rhijnsburger EH, Moonen EJ, Kleinjans JC: Reducing effects of garlic constituents on DNA adduct formation in human lymphocytes in vitro. Nutr Cancer 1997;27:177-185.
26. Petesch BL, Sumiyoshi H: Recent advances on the nutritional benefits accompanying the use of garlic as a supplement. Trends Food Sci Technol 1999;9:415-418.