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Volumn 53, Issue 6, 2005, Pages 1974-1983

Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: Use in measuring allicin bioavailability

Author keywords

Acetone; Ajoene; Allicin; Allyl methyl sulfide; Bioavailability; Diallyl disulfide; Diallyl sulfide; Diallyl trisulfide; Garlic; Metabolism; Serum lipids

Indexed keywords

ACETONE; AJOENE; ALLICIN; ALLYL COMPOUND; ALLYL METHYL SULFIDE; CYSTEINE DERIVATIVE; DIALLYL DISULFIDE; DIALLYL TRISULFIDE; GARLIC EXTRACT; S ALLYLMERCAPTOCYSTEINE; UNCLASSIFIED DRUG;

EID: 15444365720     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf048323s     Document Type: Article
Times cited : (129)

References (44)
  • 3
    • 0034687099 scopus 로고    scopus 로고
    • Garlic for treating hypercholesterolemia: A meta-analysis of randomized clinical trials
    • Stevinson, C.; Pittler, M. H.; Ernst, E. Garlic for treating hypercholesterolemia: A meta-analysis of randomized clinical trials. Am. Intern. Med. 2000, 133, 420-429.
    • (2000) Am. Intern. Med. , vol.133 , pp. 420-429
    • Stevinson, C.1    Pittler, M.H.2    Ernst, E.3
  • 4
    • 0034843579 scopus 로고    scopus 로고
    • Low allicin release from garlic supplements: A major problem due to the sensitivities of alliinase activity
    • Lawson, L. D.; Wang, Z. J. Low allicin release from garlic supplements: A major problem due to the sensitivities of alliinase activity. J. Agric. Food Chem. 2001, 49, 2592-2599.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 2592-2599
    • Lawson, L.D.1    Wang, Z.J.2
  • 5
    • 0035102170 scopus 로고    scopus 로고
    • Allicin release under simulated gastrointestinal conditions from garlic powder tablets employed in clinical trials on serum cholesterol
    • Lawson, L. D.; Wang, Z. J.; Papadimitriou, D. Allicin release under simulated gastrointestinal conditions from garlic powder tablets employed in clinical trials on serum cholesterol. Planta Med. 2001, 67, 13-18.
    • (2001) Planta Med. , vol.67 , pp. 13-18
    • Lawson, L.D.1    Wang, Z.J.2    Papadimitriou, D.3
  • 6
    • 33947445717 scopus 로고
    • Allicin, the antibacterial principle of Allium sativum. 1. Isolation, physical properties, and antibacterial action
    • Cavallito, C. J.; Bailey, J. H. Allicin, the antibacterial principle of Allium sativum. 1. Isolation, physical properties, and antibacterial action. J. Am. Chem. Soc. 1944, 66, 1950-1951.
    • (1944) J. Am. Chem. Soc. , vol.66 , pp. 1950-1951
    • Cavallito, C.J.1    Bailey, J.H.2
  • 7
    • 74049134817 scopus 로고
    • Chemical investigations on alliin, the specific principle of garlic
    • Stoll, A.; Seebeck, E. Chemical investigations on alliin, the specific principle of garlic. Adv. Enzymol. 1951, 11, 377-400.
    • (1951) Adv. Enzymol. , vol.11 , pp. 377-400
    • Stoll, A.1    Seebeck, E.2
  • 8
    • 0026656973 scopus 로고
    • Characterization of the formation of allicin and other thiosulfinates from garlic
    • Lawson, L. D.; Hughes, B. G. Characterization of the formation of allicin and other thiosulfinates from garlic. Planta Med. 1992, 58, 345-350.
    • (1992) Planta Med. , vol.58 , pp. 345-350
    • Lawson, L.D.1    Hughes, B.G.2
  • 9
    • 0026578442 scopus 로고
    • Inhibition of whole blood platelet aggregation by compounds in garlic clove extracts and commercial garlic products
    • Lawson, L. D.; Ransom, D. K.; Hughes, B. G. Inhibition of whole blood platelet aggregation by compounds in garlic clove extracts and commercial garlic products. Thromb. Res. 1992, 65, 141-156.
    • (1992) Thromb. Res. , vol.65 , pp. 141-156
    • Lawson, L.D.1    Ransom, D.K.2    Hughes, B.G.3
  • 10
    • 0346786772 scopus 로고    scopus 로고
    • Garlic: A review of its medicinal effects and indicated active compounds
    • Lawson, L. D., Bauer, R., Eds.; ACS Symposium Series 691; American Chemical Society: Washington, DC
    • Lawson, L. D. Garlic: A review of its medicinal effects and indicated active compounds. In Phytomedicines of Europe: Chemistry and Biological Activity; Lawson, L. D., Bauer, R., Eds.; ACS Symposium Series 691; American Chemical Society: Washington, DC, 1998; pp 176-209.
    • (1998) Phytomedicines of Europe: Chemistry and Biological Activity , pp. 176-209
    • Lawson, L.D.1
  • 11
    • 0027762678 scopus 로고
    • Pre-hepatic fate of the organosulfur compounds derived from garlic (Allium sativum)
    • Lawson, L. D.; Wang, Z. J. Pre-hepatic fate of the organosulfur compounds derived from garlic (Allium sativum). Planta Med. 1993, 59, A688.
    • (1993) Planta Med. , vol.59
    • Lawson, L.D.1    Wang, Z.J.2
  • 12
    • 84985204580 scopus 로고
    • Odor components of human breath after the ingestion of grated raw garlic
    • Minami, T.; Boku, T.; Inada, K.; Morita, M.; Okazaki, Y. Odor components of human breath after the ingestion of grated raw garlic. J. Food Sci. 1989, 54, 763-765.
    • (1989) J. Food Sci. , vol.54 , pp. 763-765
    • Minami, T.1    Boku, T.2    Inada, K.3    Morita, M.4    Okazaki, Y.5
  • 13
    • 0001244535 scopus 로고
    • Allium chemistry: Identification of natural abundance of organoselenium compounds in human breath after ingestion of garlic using gas chromatography with atomic emission detection
    • Cai, X. J.; Block, E.; Uden, P. C.; Quimby, B. D.; Sullivan, J. J. Allium chemistry: Identification of natural abundance of organoselenium compounds in human breath after ingestion of garlic using gas chromatography with atomic emission detection. J. Agric. Food Chem. 1995, 43, 1751-1753.
    • (1995) J. Agric. Food Chem. , vol.43 , pp. 1751-1753
    • Cai, X.J.1    Block, E.2    Uden, P.C.3    Quimby, B.D.4    Sullivan, J.J.5
  • 14
    • 0032942877 scopus 로고    scopus 로고
    • Differentiation of mouth versus gut as site of origin of odoriferous breath gases after garlic ingestion
    • Suarez, F.; Springfield, J.; Furne, J.; Levitt, M. Differentiation of mouth versus gut as site of origin of odoriferous breath gases after garlic ingestion. Am. J. Physiol. 1999, 276, G425-G430.
    • (1999) Am. J. Physiol. , vol.276
    • Suarez, F.1    Springfield, J.2    Furne, J.3    Levitt, M.4
  • 15
    • 0001173769 scopus 로고    scopus 로고
    • Analysis of compounds in human breath after ingestion of garlic using proton-transfer-reaction mass spectrometry
    • Taucher, J.; Hansel, A.; Jordan, A.; Lindinger, W. Analysis of compounds in human breath after ingestion of garlic using proton-transfer-reaction mass spectrometry. J. Agric. Food Chem. 1996, 44, 3778-3782.
    • (1996) J. Agric. Food Chem. , vol.44 , pp. 3778-3782
    • Taucher, J.1    Hansel, A.2    Jordan, A.3    Lindinger, W.4
  • 16
    • 33947443111 scopus 로고
    • Allicin, the antibacterial principle of Allium sativum. 2. Determination of the chemical structure
    • Cavallito, C. J.; Buck, J. S.; Suter, C. M. Allicin, the antibacterial principle of Allium sativum. 2. Determination of the chemical structure. J. Am. Chem. Soc. 1944, 66, 1952-1954.
    • (1944) J. Am. Chem. Soc. , vol.66 , pp. 1952-1954
    • Cavallito, C.J.1    Buck, J.S.2    Suter, C.M.3
  • 17
    • 0031051985 scopus 로고    scopus 로고
    • TLC analysis of Allium sativum constituents
    • Keusgen, M. TLC analysis of Allium sativum constituents. Plant Med. 1997, 63, 93-94.
    • (1997) Plant Med. , vol.63 , pp. 93-94
    • Keusgen, M.1
  • 18
    • 0022896896 scopus 로고
    • The chemistry of alkyl thiosulfinate esters. 9. Antithrombotic organosulfur compounds from garlic: Structural, mechanistic, and synthetic studies
    • Block, E.; Ahmad, S.; Catalfamo, J. L.; Jain, M. K.; Apitz-Castro, R. The chemistry of alkyl thiosulfinate esters. 9. Antithrombotic organosulfur compounds from garlic: Structural, mechanistic, and synthetic studies. J. Am. Chem. Soc. 1986, 108, 7045-7055.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7045-7055
    • Block, E.1    Ahmad, S.2    Catalfamo, J.L.3    Jain, M.K.4    Apitz-Castro, R.5
  • 19
    • 0025788904 scopus 로고
    • Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products
    • Lawson, L. D.; Wang, Z. J.; Hughes, B. G. Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products. Planta Med. 1991, 57, 363-370.
    • (1991) Planta Med. , vol.57 , pp. 363-370
    • Lawson, L.D.1    Wang, Z.J.2    Hughes, B.G.3
  • 20
    • 0025762905 scopus 로고
    • HPLC analysis of allicin and other thiosulfinates in garlic clove homogenates
    • Lawson, L. D.; Wood, S. G.; Hughes, B. G. HPLC analysis of allicin and other thiosulfinates in garlic clove homogenates. Planta Med. 1991, 57, 263-270.
    • (1991) Planta Med. , vol.57 , pp. 263-270
    • Lawson, L.D.1    Wood, S.G.2    Hughes, B.G.3
  • 21
    • 0000670507 scopus 로고
    • HPLC of S-alk(en)yl-L-cysteine derivatives in garlic including quantitative determination of (+)-S-allyl-L-cysteine sulfoxide (alliin)
    • Ziegler, S. J.; Sticher, O. HPLC of S-alk(en)yl-L-cysteine derivatives in garlic including quantitative determination of (+)-S-allyl-L-cysteine sulfoxide (alliin). Planta Med. 1989, 55, 372-378.
    • (1989) Planta Med. , vol.55 , pp. 372-378
    • Ziegler, S.J.1    Sticher, O.2
  • 22
    • 0026066818 scopus 로고
    • γ-Glutamyl-S-alkylcysteines in garlic and other Allium SPP: Precursors of age-dependent trans-1-propenyl thiosulfinates
    • Lawson, L. D.; Wang, Z. Y. J.; Hughes, B. G. γ-Glutamyl-S- alkylcysteines in garlic and other Allium SPP: Precursors of age-dependent trans-1-propenyl thiosulfinates. J. Nat. Prod. 1991, 54, 436-444.
    • (1991) J. Nat. Prod. , vol.54 , pp. 436-444
    • Lawson, L.D.1    Wang, Z.Y.J.2    Hughes, B.G.3
  • 23
    • 0029883514 scopus 로고    scopus 로고
    • Investigation of organic vapor losses to condensed water vapor in Tedlar(TM) bags used for exhaled-breath sampling
    • Groves, W. A.; Zellers, E. T. Investigation of organic vapor losses to condensed water vapor in Tedlar(TM) bags used for exhaled-breath sampling. Am. Indust. Hygiene Assoc. J. 1996, 57, 257-263.
    • (1996) Am. Indust. Hygiene Assoc. J. , vol.57 , pp. 257-263
    • Groves, W.A.1    Zellers, E.T.2
  • 24
    • 0038098818 scopus 로고    scopus 로고
    • Selected ion flow tube - Mass spectrometry: Detection and real-time monitoring of flavours released by food products
    • Spanel, P.; Smith, D. Selected ion flow tube - mass spectrometry: Detection and real-time monitoring of flavours released by food products. Rapid Commun. Mass Spectrom. 1999, 13, 585-596.
    • (1999) Rapid Commun. Mass Spectrom. , vol.13 , pp. 585-596
    • Spanel, P.1    Smith, D.2
  • 25
    • 84867760227 scopus 로고    scopus 로고
    • Economic Research Service, U.S. Department Agriculture: Washington, DC, VGS-284
    • Lucier, G.; Plummer, C. Vegetables and Specialties Outlook Yearbook, Economic Research Service, U.S. Department Agriculture: Washington, DC, 2001; VGS-284, p 24.
    • (2001) Vegetables and Specialties Outlook Yearbook , pp. 24
    • Lucier, G.1    Plummer, C.2
  • 26
    • 15444379183 scopus 로고    scopus 로고
    • Garlic delayed-release tablets
    • United States Pharmacopeial Convention, Inc.: Rockville, MD
    • United States Pharmacopeial Convention. Garlic delayed-release tablets. In United States Pharmacopeia 26; United States Pharmacopeial Convention, Inc.: Rockville, MD, 2003; pp 2752-2754.
    • (2003) United States Pharmacopeia 26 , pp. 2752-2754
  • 27
    • 0025310688 scopus 로고
    • Products of allicin transformation: Ajoenes and dithiins, characterization and their determination by HPLC
    • Iberl, B.; Winkler, G.; Knobloch, K. Products of allicin transformation: Ajoenes and dithiins, characterization and their determination by HPLC. Planta Med. 1990, 56, 202-211.
    • (1990) Planta Med. , vol.56 , pp. 202-211
    • Iberl, B.1    Winkler, G.2    Knobloch, K.3
  • 29
    • 0030992920 scopus 로고    scopus 로고
    • Metabolism of the chemoprotective agent diallyl sulfide to glutathione conjugates in rats
    • Jin, L.; Baillie, T. A. Metabolism of the chemoprotective agent diallyl sulfide to glutathione conjugates in rats. Chem. Res. Toxicol. 1997, 10, 318-327.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 318-327
    • Jin, L.1    Baillie, T.A.2
  • 30
    • 0037403325 scopus 로고    scopus 로고
    • Comparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: Redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivo
    • Munday, R.; Munday, J. S.; Munday, C. M. Comparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: Redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivo. Free Radical Biol. Med. 2003, 34, 1200-1211.
    • (2003) Free Radical Biol. Med. , vol.34 , pp. 1200-1211
    • Munday, R.1    Munday, J.S.2    Munday, C.M.3
  • 31
    • 33751157708 scopus 로고
    • Comparative toxicity of prop(en)yl disulfides derived from Alliaceae: Possible involvement of 1-propenyl disulfides in onion-induced hemolytic anemia
    • Munday, R.; Manns, E. Comparative toxicity of prop(en)yl disulfides derived from Alliaceae: Possible involvement of 1-propenyl disulfides in onion-induced hemolytic anemia. J. Agric. Food Chem. 1994, 42, 959-962.
    • (1994) J. Agric. Food Chem. , vol.42 , pp. 959-962
    • Munday, R.1    Manns, E.2
  • 32
    • 0033973286 scopus 로고    scopus 로고
    • The mode of action of allicin: Its ready permeability through phospholipid membranes may contribute to its biological activity
    • Miron, T.; Rabinkov, A.; Mirelman, D.; Wilchek, M.; Weiner, L. The mode of action of allicin: Its ready permeability through phospholipid membranes may contribute to its biological activity. Biochim. Biophys. Acta 2000, 1463, 20-30.
    • (2000) Biochim. Biophys. Acta , vol.1463 , pp. 20-30
    • Miron, T.1    Rabinkov, A.2    Mirelman, D.3    Wilchek, M.4    Weiner, L.5
  • 33
    • 0034639280 scopus 로고    scopus 로고
    • S-Allylmercaptoglutathione: The reaction product of allicin with glutathione possess SH-modifying and antioxidant properties
    • Rabinkov, A.; Miron, T.; Mirelman, D.; Wilchek, M.; Glozman, S.; Yavin, E.; Weiner, L. S-Allylmercaptoglutathione: The reaction product of allicin with glutathione possess SH-modifying and antioxidant properties. Biochim. Biophys. Acta 2000, 1499, 144-153.
    • (2000) Biochim. Biophys. Acta , vol.1499 , pp. 144-153
    • Rabinkov, A.1    Miron, T.2    Mirelman, D.3    Wilchek, M.4    Glozman, S.5    Yavin, E.6    Weiner, L.7
  • 34
    • 1642498338 scopus 로고    scopus 로고
    • Hepatic metabolism of diallyl disulphide in rat and man
    • Germain, E.; Chevalier, J.; Siess, M.-H.; Teyssier, C. Hepatic metabolism of diallyl disulphide in rat and man. Xenobiotica 2003, 33, 1185-1199.
    • (2003) Xenobiotica , vol.33 , pp. 1185-1199
    • Germain, E.1    Chevalier, J.2    Siess, M.-H.3    Teyssier, C.4
  • 35
    • 12244278997 scopus 로고    scopus 로고
    • In vivo metabolism of diallyl disulphide in the rat: Identification of two new metabolites
    • Germain, E.; Auger, J.; Ginies, C.; Siess, M.-H.; Teyssier, C. In vivo metabolism of diallyl disulphide in the rat: identification of two new metabolites. Xenobiotica 2002, 32, 1127-1138.
    • (2002) Xenobiotica , vol.32 , pp. 1127-1138
    • Germain, E.1    Auger, J.2    Ginies, C.3    Siess, M.-H.4    Teyssier, C.5
  • 36
    • 0028343378 scopus 로고
    • Untersuchungen zur Pharmakokinetik der mit 35S markierten Knoblauchinhaltsstoffe Alliin, Allicin, und Vinyldithiine
    • Lachmann, G.; Lorenz, D.; Radeck, W.; Steiper, M. Untersuchungen zur Pharmakokinetik der mit 35S markierten Knoblauchinhaltsstoffe Alliin, Allicin, und Vinyldithiine. Arzneim. Forsch. 1994, 44, 734-743.
    • (1994) Arzneim. Forsch. , vol.44 , pp. 734-743
    • Lachmann, G.1    Lorenz, D.2    Radeck, W.3    Steiper, M.4
  • 37
    • 15444375184 scopus 로고
    • Serum concentration, tissue distribution, and bioavailability of allicin in rabbits by GC-analysis
    • Wang, Z.; Hong, X.; Qian, W.; Hu, C.; Wang, Y. Serum concentration, tissue distribution, and bioavailability of allicin in rabbits by GC-analysis. Zhongcaoyao 1988, 19, 540-541, 559.
    • (1988) Zhongcaoyao , vol.19 , pp. 540-541
    • Wang, Z.1    Hong, X.2    Qian, W.3    Hu, C.4    Wang, Y.5
  • 38
    • 0016809268 scopus 로고
    • Aceton in der Atemluft und Ketone im Venenblut bei vollstaendigem Fastem normal- Und uebergewichter Personen
    • Goeschke, H.; Lauffenburger, T. Aceton in der Atemluft und Ketone im Venenblut bei vollstaendigem Fastem normal- und uebergewichter Personen. Res. Exp. Med. 1975, 165, 233-244.
    • (1975) Res. Exp. Med. , vol.165 , pp. 233-244
    • Goeschke, H.1    Lauffenburger, T.2
  • 40
    • 0032957279 scopus 로고    scopus 로고
    • Allyl-containing Sulfides in garlic increase uncoupling protein content in brown adipose tissue, and noradrenaline and adrenaline secretion in rats
    • Oi, Y.; Kawada, T.; Shishido, C.; Wada, K.; Kominato, Y.; Nishimura, S.; Ariga, T.; Iwai, K. Allyl-containing Sulfides in garlic increase uncoupling protein content in brown adipose tissue, and noradrenaline and adrenaline secretion in rats. J. Nutr. 1999, 129, 336-342.
    • (1999) J. Nutr. , vol.129 , pp. 336-342
    • Oi, Y.1    Kawada, T.2    Shishido, C.3    Wada, K.4    Kominato, Y.5    Nishimura, S.6    Ariga, T.7    Iwai, K.8
  • 41
    • 0027944506 scopus 로고
    • Relationship between cytochrome P450 2E1 and acetone catabolism in rats as studied with diallyl sulfide as an inhibitor
    • Chen, L.; Lee, M.; Hong, J. Y.; Huang, W.; Wang, E.; Yang, C. S. Relationship between cytochrome P450 2E1 and acetone catabolism in rats as studied with diallyl sulfide as an inhibitor. Biochem. Pharmacol. 1994, 48, 2199-2205.
    • (1994) Biochem. Pharmacol. , vol.48 , pp. 2199-2205
    • Chen, L.1    Lee, M.2    Hong, J.Y.3    Huang, W.4    Wang, E.5    Yang, C.S.6
  • 42
    • 0001658031 scopus 로고
    • Studies on the nutritional value of Allium plants. 36. Decomposition of alliin homologues by microorganism and formation of substance with thiamine masking activity
    • Murakami, F. Studies on the nutritional value of Allium plants. 36. Decomposition of alliin homologues by microorganism and formation of substance with thiamine masking activity. Bitamin 1960, 20, 126-131.
    • (1960) Bitamin , vol.20 , pp. 126-131
    • Murakami, F.1
  • 43
    • 15444381051 scopus 로고    scopus 로고
    • Transformation of alliin and alliin homologues by C-S-lyases from enterobacteriaceae
    • Knobloch, K. Transformation of alliin and alliin homologues by C-S-lyases from enterobacteriaceae. Phytomedicine 2000, 7 (supplement 2), 50.
    • (2000) Phytomedicine , vol.7 , Issue.2 SUPPL. , pp. 50
    • Knobloch, K.1
  • 44
    • 3142642261 scopus 로고
    • Allithiamine, a newly found derivative of vitamin B1, III. On the allicin homologues in the plants of the Allium species
    • Fujiwara, M.; Yoshimura, M.; Tsuno, S. Allithiamine, a newly found derivative of vitamin B1, III. On the allicin homologues in the plants of the Allium species. J. Biochem. 1955, 42, 591-601.
    • (1955) J. Biochem. , vol.42 , pp. 591-601
    • Fujiwara, M.1    Yoshimura, M.2    Tsuno, S.3


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