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Thermal Generation and Antimicrobial Activity of Unusual Heterocyclic Sulfur Compounds in Garlic  

Chung, In-Shick (Department of Food Science, Sejong University)
Chae, Kyung-Yun (Tourism and Food Service Business Department, Osan College)
Kyung, Kyu-Hang (Department of Food Science, Sejong University)
Publication Information
Food Science and Biotechnology / v.17, no.5, 2008 , pp. 1032-1037 More about this Journal
Abstract
Lowly volatile heterocyclic sulfur compounds generated in autoclaved garlic extract were isolated and identified, and their antimicrobial activity was determined. Two kinds of unusual volatile sulfur compounds were separated from heated garlic by preparative recycling high performance liquid chromatography (HPLC), and identified by gas chromatography (GC)-mass spectrometry (MS) and $^1H$-nuclear magnetic resonance (NMR). They had heterocyclic structures with 4 to 5 sulfur atoms in the molecules. 4-Methyl-1,2,3-trithiolane (MTTT) is highly volatile and was not able to be concentrated, and was identified by GCMS only. MTTT and 6-methyl-1,2,3,4,5-pentathiepane (MPTP) are lowly volatile and were obtained in pure states to be positively identified for the first time. All 3 heterocyclic sulfur compounds began to appear by the time when the early-formed diallyl sulfides started to disappear. The minimum inhibitory concentration range of MTTT and MPTP was determined to be between 1 and 6 ppm against all yeasts tested. MTTT and MPTP were lowly volatile and sparingly soluble in water.
Keywords
garlic; heterocyclic; volatile sulfur compound; antimicrobial activity;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 2
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1 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
2 Brodnitz MH, Pascale JV, Derslice LV. Flavor components of garlic extract. J. Agr. Food Chem. 19: 273-275 (1971)   DOI
3 Yu T-H, Wu C-M, Rosen RT, Hartman TG, Ho C-T. Volatile compounds generated from thermal degradation of alliin and deoxyalliin in an aqueous solution. J. Agr. Food Chem. 42: 146-153 (1994)   DOI   ScienceOn
4 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
5 Le Dinh H, Kyung KH. Inhibition of yeast film formation in fermented vegetables by materials derived from garlic using cucumber pickle fermentation as a model system. Food Sci. Biotechnol. 15: 469-473 (2006)   과학기술학회마을
6 Kyung KH, Kim MH, Park MS, Kim YS. Alliinase-independent inhibition of Staphylococcus aureus B33 by heated garlic. J. Food Sci. 67: 780-785 (2002)   DOI   ScienceOn
7 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
8 Steven FS, Griffin MM, Smith RH. Disulfide exchange reactions in the control of enzymic activity. Eur. J. Biochem. 119: 75-78 (1981)   DOI   ScienceOn
9 Yu T-H, Wu C-M, Ho C-T. Volatile compounds of deep-oil fried, microwave heated, and oven-baked garlic slice. J. Agr. Food Chem. 41: 800-805 (1993)   DOI   ScienceOn
10 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
11 Pentz R, Siegers CP. Garlic preparations: Methods for quantitative and qualitative assessment of their ingredient. pp. 109-134. In: Garlic, the Science and Therapeutic Application of Allium sativum L. and Related Species. 2nd ed. Koch HP, Lawson LD (eds). Williams & Wilkins, Baltimore, MD, USA (1996)
12 Block E, Iyer R, Grisoni S, Saha C, Belman S, Lossing FP. Lipoxygenase inhibitor from the essential oil of garlic: Markovnikov addition of the allyldithioradical to olefins. J. Am. Chem. Soc. 110: 7813-7827 (1988)   DOI   ScienceOn
13 Block E, Ahmed S, Jain MK, Creely RW, Aptiz-Castro R, Cruz MR. (E,Z)-Ajoene: A potent antithrombotic agent from garlic. J. Am. Chem. Soc. 106: 8295-8296 (1984)   DOI   ScienceOn
14 Yu T-H, Wu C-M, Liou Y-C. Volatile compounds from garlic. J. Agr. Food Chem. 37: 725-730 (1989)   DOI
15 Choi MK, Chae KY, Lee JY, Kyung KH. Antimicrobial activity of chemical substances derived from S-alk(en)yl-L-cysteine sulfoxide (alliin) in garlic, Allium sativum L. Food Sci Biotechnol. 16: 1-7 (2007)   과학기술학회마을
16 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
17 Kubec R, Velisec J, Kubelka V. Sulfur-containing volatiles arising by thermal degradation of alliin and deoxyalliin. J. Agr. Food Chem. 45: 3580-3585 (1997)   DOI   ScienceOn
18 O'Gara EA, Hill DJ, Maslin DJ. Activities of garlic oil, garlic powder, and their diallyl constituents against Helicobacter pylori. Appl. Environ. Microb. 66: 2269-2273 (2000)   DOI   ScienceOn
19 Small LD, Bailey JH, Cavallito CJ. Alkyl thiosulfinates. J. Am. Chem. Soc. 69: 1710-1713 (1947)   DOI
20 Ross ZM, O'Gara EA, Hill DJ, Sleighttholme 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. Microb. 67: 475-480 (2001)   DOI   ScienceOn
21 Smith RH. Kale poisoning: The Brassica anaemia factor. Vet. Rec. 107: 12-15 (1980)   DOI   ScienceOn
22 Cavallito CJ, Buck JS, Suter CM. Allicin, the antibacterial principles of Allium sativum. II: Determination of the chemical structure. J. Am. Chem. Soc. 66: 1952-1954 (1944)   DOI
23 Small LD, Bailey JH, Cavallito CJ. Comparison of some properties of thiosulfonates and thiosulfinates. J. Am. Chem. Soc. 71: 3565-3566 (1949)   DOI
24 Choi JH, Kyung KH. Allyl alcohol is the sole antiyeast compound in heated garlic extract. J. Food Sci. 70: M305-M309 (2005)   DOI
25 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)
26 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