Antimicrobial Activity of Chemical Substances Derived from S-Alk(en)yl-L-Cysteine Sulfoxide (Alliin) in Garlic, Allium sativum L. |
Choi, Mi-Kyung
(Department of Food Science, Sejong University)
Chae, Kyung-Yeon (Department of Food Science, Sejong University) Lee, Joo-Young (Department of Food Science, Sejong University) Kyung, Kyu-Hang (Department of Food Science, Sejong University) |
1 | Kyung KH, Fleming HP. S-Methyl-L-cysteine sulfoxide as the precursor of methyl methanethiosulfinate, the principal antibacterial compound in cabbage. J. Food Sci. 59: 350-355. (1994) DOI ScienceOn |
2 | Delaquis PJ, Mazza G. Antimicrobial properties of isothiocyanates in food preservation. Food Technol.-Chicago 49: 73-84 (1995) |
3 | Rundqvist C. Pharmacological investigation of Allium bulbs. Pharmaceutiskt Notisblad. 18: 323-333 (1909) |
4 | Caragay AB. Cancer-preventive foods and ingredients. Food Technol.-Chicago 46: 65-68 (1992) |
5 | Alberto-Puleo M. Physiological effects of cabbage with reference to its potential as a dietary cancer-inhibitor and its use in ancient medicine. J. Ethnopharmacol. 9: 261-272 (1983) DOI ScienceOn |
6 | Wills ED. Enzyme inhibition by allicin, the active principle of garlic. Biochem. J. 63: 514-520 (1956) DOI |
7 | Ghannoum MA. Studies of the antimicrobial mode of action of Allium sativum (garlic). J. Gen. Microbiol. 134: 2917-2924 (1988) |
8 | Feldberg RS, Chang SC, Kotik AN, Nadler M, Neuwirth Z, Sundstrom DC, Thompson NH. In vitro mechanism of inhibition of bacterial cell growth by allicin. Antimicrob. Agents Ch. 32: 1763-1768 (1988) DOI ScienceOn |
9 | Mantis AJ, Karaioannoglou PG, Spanos GP, Panetos AG The effect of garlic extract on food poisoning bacteria in culture media. I. Staphylococcus aureus. Lebensm. - Wiss. Technol. 11: 26-28 (1978) |
10 | DeWit JC, Notermans S, Gorin N, Kampelmacher EH. Effects of garlic oil or onion oil on toxin production by Clostridium botulinum in meat slurry. J. Food Protect. 42: 222-224 (1979) DOI |
11 | Moore GS, Atkins RD. The fungicidal and fungistatic effects of aqueous garlic extract on medically important yeast-like fungi. Mycologia 69: 341-348 (1977) DOI |
12 | Kyung KH, Kim MH, Park MS, Kim YS. Alliinase-independent inhibition of Staphylococus aureus B33 by heated garlic. J. Food Sci. 67: 780-785 (2002) DOI ScienceOn |
13 | Freeman GG, Whenham RJ. The use of synthetic (+/-)-S-I-propyl-Lcysteine sulphoxide and of alliinase preparations in studies of flavour changes resulting from processing of onion (Allium cepa L.). J. Sci. Food Agr. 26: 1333-1346 (1975) DOI |
14 | Fujiwara M, Yoshimura M, Tsuno S, Murakami F. 'Allithiamine,' a newly found derivative of vitamin BI. IV. On the allicin homologues in the vegetables. J. Biochem. -Tokyo 45: 141-149 (1958) DOI |
15 | Horhammer L, Wagner H, Seitz M, Vejdelek ZJ. Onion flavors and their analysis by gas chromatography-mass spectrometry. Pharmazie 23: 462-466 (1968) |
16 | Nomura J, Nishizuka Y, Hayaishi O. S-Alkylcysteinase: Enzymatic cleavage of s-methyl-L-cysteine and its sulfoxide. J. Biol. Chem. 238: 1441-1446 (1963) |
17 | Cavallito CJ, Buck JS, Suter CM. Allicin, the antibacterial principles of Allium sativim. II. Determination of the chemical structure. J. Am. Chem. Soc. 66: 1952-1954 (1944) DOI |
18 | Yoshida S, Kasuga S, Hayashi N, Ushiroguchi T, Matsuura H, Nakagawa S. Antifungal activity of ajoene derived from garlic. Appl. Environ. Microbiol. 53: 615-617 (1987) |
19 | Lee S, Woo YH, Kyung KH. Allyl alcohol found in heated garlic is a potent selective inhibitor for yeasts but not for bacteria. J. Microbiol. Biotechn. 16: 1236-1239 (2006) 과학기술학회마을 |
20 | Youngleson JS, Santangelo JD, Jones DT, Woods DR. Cloning and expression of a Clostridium acetobutylicum alchohol dehyadrogease gene in Escherichia coli. Appl. Environ. Microbiol. 54: 676-682 (1988) |
21 | Choi JH, Kyung KH. Allyl alcohol is the sole antiyeast compound in heated garlic extract. J. Food Sci. 70: M305-M309 (2005) DOI |
22 | Dickinson F, Dalziel K. The specifications and configurations of ternary complexes of yeast and liver alcohol dehydrogenases. Biochem. J., 104: 165-172 (1967) DOI |
23 | Cavallito CJ, Bailey JH. Allicin, the antibacterial principle of Allium sativum. I: Isolation, physical properties and antimicrobial action. J. Am. Chem. Soc. 66: 1950-1951 (1944) DOI |
24 | Bradshaw JE, Borzucki R. Digestability, S-methyl-L-cysteine sulfoxide content and thiocyante ion content of cabbage of stockfeeding. J. Sci. Food Agr. 33: 1-5 (1982) DOI |
25 | Kim JW, Kyung KH. Antiyeast activity of heated garlic in the absence of alliinase enzyme action. J. Food Sci. 68: 1766-1770 (2003) DOI ScienceOn |
26 | Naganawa R, Iwata N, Ishikawa K, Fukyda H, Fujino T, Suzuki A. Inhibition of microbial growth by ajoene, a sulfur-containg compound derived from garlic. Appl. Environ. Microbiol. 62: 4238-4242 (1996) |
27 | Al-Delaimy KS, Barakat MMF. Antimicrobial and preservative activity of garlic on fresh ground camel meat. 1. Effect of fresh ground garlic segments. J. Sci. Food Agr. 22: 96-98 (1971) DOI |
28 | Lawson LD, Wang ZJ, Hughes BG. Identification and HPLC analysis of sulfides and dialk(en)yl thiosulfinates in commercial garlic products. Planta Med. 57: 363-370 (1991) DOI ScienceOn |
29 | Marks HS, Hilson JA, Leichtweis HC, Stoewsand GS. S-Methylcysteine sulfoxide in Brassica vegetables and formation of methyl methanethiosulfinate from Brussels sprout. J. Agr. Food Chem. 40: 2098-2101 (1992) DOI |
30 | Kunelius HT, Sanderson JB, Narashimhalu PR. Effect of seeding date on yields and quality of green forage crops. Can. J. Plant Sci. 67: 1045-1050 (1987) DOI |
31 | Murakami F. Studies on the nutritional value of Allium Plants (XXXVI) Decomposition of alliin homologues by microorganism and formation of substance with thiamine masking activity. Vitamins (Tokyo) 20: 126 (1960) |
32 | Stoll A, Seebeck E. Synthesis of natural alliin and its three optically active isomers. 5. Communication about Allium-substance. Helv. Chim. Acta 34: 481-487 (1951) DOI |
33 | Kyung KH, Fleming HP. Antibacterial activity of cabbage juice against lactic acid bacteria. J. Food Sci. 59: 125-129 (1994) DOI ScienceOn |
34 | Synge RLM, Wood JC. (+)-S-Methyl-L-cysteine s-oxide in cabbage. Biochem. J. 64: 252-259 (1956) DOI |
35 | Dababneh FA, Al-Delaimy KS. Inhibition of Staphylococcus aureus by garlic extract. Lebensm. -Wiss. Technol. 17: 29-31 (1984) |
36 | Conner DE, Beuchat LR. Effects of essential oils from plants on growth of food spoilage yeasts J. Food Sci. 49: 429-434 (1984) DOI |
37 | Hamamoto A, Mazelis M. The C-S lyases of higher plants; Isolation and properties of homogeneous cystine lyase from broccoli. Plant Physiol. 80: 702-706 (1986) DOI ScienceOn |
38 | Kim JW, Kim YS, Kyung KH. Inhibitory activity of essential oils of garlic and onion against bacteria and yeasts. J. Food Protect. 67: 499-504 (2004) DOI |
39 | Block E, Naganathan S, Putman D, Zhao S-H. Allium chemistry: HPLC analysis of thiosulfinates from onion, garlic, wild garlic (Ram sons), leek, scallion, shallot, elephant (great-headed) garlic chive, and Chinese chive. J. Agr. Food Chem. 40: 2418-2430 (1992) DOI |
40 | Focke M, Feld A, Lichtenthaler HK. Allicin, a naturally occurring antibiotic from garlic, specifically inhibits acetyl-CoA synthetase. FEBS 261: 106-108 (1990) DOI ScienceOn |
41 | Block E. Flavor artifacts. J. Agr. Food Chem. 41: 692 (1993) |
42 | Brown HD, Matzuk AR, Becker HJ, Conbere JP, Constantin JM, Solotorovsky M, Winsten S, Ironson E, Quastel JH. The antituberculosis activity of some ethylmercapto compounds. J. Am. Chem. Soc. 76: 3860 (1954) |
43 | 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. 13: 235-239 (2004) |
44 | Ingersoll RL, Volirath RE, Scott B, Lindegren CC. Bactericidal activity of crotonaldehyde. Food Res. 3: 389-392 (1938) DOI |
45 | Stoll A, Seebeck E. Chemical investigation of alliin, the specific principle of garlic. Adv. Enzymol. 11: 377-400 (1951) |
46 | Block E, Ahmed S, Jain MK, Creely RW, Apitz-Castro R, Cruz MR. (E,Z)-Ajoene: A potent antithrombotic agent from garlic. J. Am. Chem. Soc. 106: 8295-8296 (1984) DOI ScienceOn |
47 | Morris CJ, Thompson JF. The identification of (+)S-methyl-L-cysteine sulfoxide in plants. J. Am. Chem. Soc. 78: 1605-1608 (1956) DOI |
48 | Marks HS. Isolation, identification, and genotoxic inhibitory efficacy of naturally occurring organosulfur compounds present in Brassica vegetables. PhD thesis, Cornell University Ithaca NY USA (1992) |
49 | Al-Delaimy KS, Ali SH. Antibacterial action of vegetable extracts on the growth of pathogenic bacteria. J. Sci. Food Agr. 21: 110-112 (1970) DOI |
50 | Adetumbi M, Javor GT, Lau BHS. Allium sativum (garlic) inhibits lipid synthesis in Candida albicans. Antimicrob. Agents Ch. 30: 499-501 (1986) DOI ScienceOn |
51 | Le Dinh H, Kyung KH. Inhibition of yeast film formation in fermented vegetables by materials derived from garlic using cucumber pickle fermentation as model system. Food Sci. Biotechnol. 15: 469-473 (2006) 과학기술학회마을 |
52 | Johnson MG, Vaughn RH. Death of Salmonella typhimurium and Escherichia coli in the presence of freshly reconstituted dehydrated garlic and onion. Appl. Microbiol. 17: 903-905 (1969) |
53 | Yu T-H, Wu C-M. Stability of allicin in garlic juice. J. Food Sci. 54: 977-981 (1989) DOI |
54 | Lawson LD. The composition and chemistry of garlic cloves and processed garlic. pp. 37-107. In: Garlic, The Science and Therapeutic Applications of Allium sativum L. and Related Species. 2nd ed. Koch HP, Lawson LD (eds). Williams & Wilkins, Baltimore, MD, USA (1996) |
55 | O'Gara EA, Hill DJ, Maslin DJ. Activities of garlic oil, garlic powder, and their diallyl constituents against Helicobacter pylori. Appl. Environ. Microbiol. 66: 2269-2273 (2000) DOI |
56 | Singh KV, Shukula NP. Activity of multiple resistant bacteria of garlic (Allium sativum) extract. Fitoterapia 15: 313-315 (1984) |
57 | Moon B-Y, Lee E-J, Park J-H. Characteristics of antibiotic resistance of foodborne pathogens adapted to garlic, Allium sativum L. Food Sci. Biotechnol. 15: 511-515 (2006) 과학기술학회마을 |
58 | Lawson LD. Garlic: A review of its medicinal effects and indicated active compounds. pp. 176-209. In: Phytomedicines of Europe: Their Chemistry & Biological Activity. Lawson LD, Bauer R (eds). ACS Symposium Series 691, American Chemical Society, Washington, DC, USA (1998) |
59 | Ross ZM, O'Gara EA, Hill DJ, Sieighttholme HV, Maslin DJ. Antimicrobial properties of garlic oil against human enteric bacteria: Evaluation of methodologies and comparisons with garlic oil sulfides and garlic powder. Appl. Environ. Microbiol. 67: 475-480 (2001) DOI ScienceOn |
60 | Karaioannoglou PG, Mantis AJ, Panetos AG The effects of garlic extract on lactic acid bacteria (Lactobacillus plantarum) in culture media. Lebensm. - Wiss. Technol. 10: 148-150 (1977) |
61 | Augusti KT, Mathew PT. Lipid lowering effect of allicin (diallyl disulphide-oxide) on long term feeding to normal rats. Experientia 30: 468-470 (1974) DOI ScienceOn |
62 | Walton L, Herbold M, Lindegren CC. Bactericidal effects of vapors from crushed garlic. Food Res. 1: 163-169 (1936) DOI |
63 | Saleem ZM, Al-Delaimy KS. Inhibition of Bacillus cereus by garlic extracts. J. Food Protect. 45: 1007-1009 (1982) DOI |
64 | Mae T, Ohira K, Fujiwara A. Fate of (+)S-methyl-L-cysteine sulfoxide in Chinese cabbage, Brassica pekinesis RUPR. Plant Cell Physiol. 12: 1-11 (1971) DOI |
65 | Small LD, Bailey JH, Cavallito CJ. Comparison of some properties of thiosulfonates and thiosulfinates. J. Am. Chem. Soc. 71: 3565-3566 (1949) DOI |
66 | Rando RR. Allyl alcohol-induced irreversible inhibition of yeast alcohol dehydrogenase. Biochem. Pharmacol. 23: 2328-2331 (1974) DOI ScienceOn |
67 | Lorowitz W, Clark D. Escherichia coli mutants with a temperaturesensitive alcohol dehydrogenase. J. Bacteriol. 152: 935-938 (1982) |
68 | Stoll A, Seebeck E. About alliin, the genuine mother substance of garlic. 1. Communication about Alliium sunstance. Helv. Chim. Acta 31: 189-210 (1948) DOI |
69 | Small LD, Bailey JH, Cavallito CJ. Alkyl thiosulfinates. J. Am. Chem. Soc. 69: 1710-1713 (1947) DOI |
70 | Srivastava KC, Perera AD, Saridakis HO. Bacteriostatic effects of garlic sap on Gram negative pathogenic bacteria: An in vitro study. Lebensm. -Wiss. Technol. 15: 74-76 (1982) |
71 | Rees LP, Minney SF, Plummer NT, Slator JH, Skyrme DA. A quantitative assessment of the antimicrobial activity of garlic (Allium sativum). World J. Microb. Biot. 9: 303-307 (1993) DOI ScienceOn |
72 | Mantis AJ, Koidis PA, Karaioannoglou PG, Panetos AG. Effect of garlic extract on food poisoning bacteria. Lebensm. - Wiss. Technol. 12: 230-232 (1979) |
73 | Ziegler SJ, Stitcher O. HPLC of S-alk(en)yl-L-cysteine derivatives in garlic including quantitative determination of (+)S-allyl-L-cysteine sulfoxide (alliin). Planta Med. 55: 372-377 (1989) DOI ScienceOn |
74 | Smith RH. Kale Poisoning: The Brassica anaemia factor. Vet. Rec. 107: 12-15 (1980) DOI ScienceOn |
75 | Kubelik J. Antimicrobial properties of garlic. Pharmazie 25: 266-269 (1970) |
76 | Sherman JM, Hodge HM. The bactericidal properties of certain plant juices. J. Bacteriol. 31: 96 (1936) |
77 | Barone FE, Tansey MR. Isolation, purification, identification, synthesis, and kinetics of activity of the anticandidal component of Allium sativum, and a hypothesis for its mode of action. Mycologia 69: 793-825 (1977) DOI |
78 | Tansey MR. Appleton JA. Inhibition of fungal growth by garlic extract. Mycologia 67: 409-413 (1975) DOI |
79 | Pentz R, Siegers CP. Garlic preparations: Methods for quantitative and qualitative assessment of their ingredients. pp. 109-134. In: Garlic, The Science and Therapeutic Applicatiollof Allium sativum L. and Related Species. 2nd ed. Koch HP, Lawson LD (eds). Williams & Wilkins, Baltimore, MD, USA (1996) |
80 | Virtanen AI. Studies on organosulfur compounds and other labile substances in plants. Phytochemistry 4: 207-228 (1965) DOI ScienceOn |
81 | Lubeck VL. Method of stabilization of antibiotic effective ingredient of Allium sativum. Deutsch. Pat. 943250 (1956) |
82 | Virtanen AI. Some organic sulfur compounds in vegetables and fodder plants and their significance in human nutrition. Angew. Chem. Int. Edit. 6: 299-306 (1962) |
83 | Zsolnai VT. The antimicrobial action of thiocyanates and isothiocyanates. Int. Mitteilung, Arzneim. Forsch., 16: 870-876 (1966) |
84 | Brodnitz MH, Pascale JV, von Derslice L. Flavor components of garlic extract. J. Agr. Food Chem. 19: 273-275 (1971) DOI |