Determination of seven organosulfur compounds in garlic by high-performance liquid chromatography

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 5, 2006, Pages 1535-1540

  Ichikawa, Makoto ^a   Ide, Nagatoshi ^a   Yoshida, Jiro ^b   Yamaguchi, Hiroyuki ^a   Ono, Kazuhisa ^b  

^a WAKUNAGA PHARMACEUTICAL CO LTD   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Allium sativum; Garlic; HPLC; Organosulfur compounds; Validation

Indexed keywords

ALLIIN; CYSTEINE; DRUG DERIVATIVE; SOLVENT; SULFUR DERIVATIVE;

ARTICLE; CHEMISTRY; GARLIC; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; REPRODUCIBILITY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTEINE; GARLIC; REPRODUCIBILITY OF RESULTS; SOLVENTS; SULFUR COMPOUNDS;

ALLIUM SATIVUM;

EID: 33645459926     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051742k     Document Type: Article

References (30)

1. Rahman, K. Garlic and aging: new insights into an old remedy. Ageing Res. Rev. 2003, 2, 39-56.
2. Lawson, L. D. Bioactive organosulfur compounds of garlic and garlic products. Role in reducing blood lipids. In Human Medical Agents from Plants; ACS Symposium Series 534; Kinghorn, A. D., Balandrin, M. F., Eds.; American Chemical Society: Washington, DC, 1993; pp 306-330.
3. Agarwal, K. C. Therapeutic actions of garlic constituents. Med. Res. Rev. 1996, 16, 111-124.
4. Yanagita, Y.; Han, S. Y.; Wang, Y. M.; Tsuruta, Y.; Anno, T. Cycloalliin, a cyclic sulfur imino acid, reduces serum triglycerol in rats. Nutrition 2003, 19, 140-143.
5. Sendl, A.; Elbl, G.; Steinke, B.; Redl, K.; Breu, W.; Wagner, H. Comparative pharmacological investigations of Allium ursinum and Allium sativum. Planta Med. 1992, 58, 1-7.
6. Yeh, Y. Y.; Liu, L. Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies. J. Nutr. 2001, 131, 989S-993S.
7. Block, E. The organosulfur chemistry of the genus Allium - implications for the organic chemistry of sulfur. Angew Chem., Int. Ed. Engl. 1992, 31, 1135-1178.
8. Lancaster, J. E.; Shaw, M. L. γ-Glutamyl peptides in the biosynthesis of S-alk(en)yl-L-cysteine sulphoxides (flavour precursors) in Allium. Phytochemistry 1989, 28, 455-460.
9. Lawson, L. D. 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, H. P., Lawson, L. D., Eds.; Williams & Wilkins: Baltimore, MD, 1996; pp 37-107.
10. Ueda, Y.; Kawajiri, H.; Miyamura, N.; Miyajima, R. Content of some sulfur-containing compounds and free amino acids in various strains of garlic. Nippon Shokuhin Kogyo Gakkaishi 1991, 38, 429-434.
11. Matsuura, H.; Inagaki, M.; Maeshige, K.; Ide, N.; Kajimura, Y.; Itakura, Y. Changes in contents of γ-glutamyl peptides and fructan during growth of Allium sativum. Planta Med. 1996, 62, 70-71.
12. Lawson, L. D.; Wang, Z. 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.
13. United States Pharmacopeial Convention. Garlic. In United States Pharmacopoeia 27; United States Pharmacopeial Convention, Inc.: Rockville, MD, 2004; pp 1997-1999.
14. 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.
15. Eckner, M. M.; Sticher, O.; Meier, B. Reversed-phase high-performance liquid chromatography of 5-alk(en)yl-L-cysteine derivatives in Allium sativum including the determination of (+)-S-allyl-L-cysteine sulphoxide, γ-L-glutamyl-S-allyl-L-cysteine and γ-L-glutamyl-S-(trans-1- propenyl)-L-cysteine. J. Chromatogr. 1992, 625, 183-190.
16. Imai, J.; Ide, N.; Nagae, S.; Moriguchi, T.; Mastuura, H.; Itakura, Y. Antioxidant and radical scavenging effects of aged garlic extract and its constituents. Planta Med. 1994, 60, 417-420.
17. Krest, I.; Glodek, J.; Keusgen, M. Cysteine sulfoxides and alliinase activity of some Allium species. J. Agric. Food Chem. 2000, 48, 3753-3760.
18. Yoo, K. S.; Pike, L. M. Determination of flavor precursor compound S-alk(en)yl-L-cysteine sulfoxides by an HPLC method and their distribution in Allium species. Sci. Hortic. 1998, 72, 1-10.
19. Thomas, D. J.; Parkin, K. L. Quantification of alk(en)yl-L-cysteine sulfoxides and related amino acids in Alliums by high-performance liquid chromatography. J. Agric. Food Chem. 1994, 42, 1632-1638.
20. Ueda, Y.; Sakaguchi, M.; Hirayama, K.; Miyajima, R.; Kimizuka, A. Characteristic flavor constituents in water extract of garlic. Agric. Biol. Chem. 1990, 54, 163-169.
21. Arnault, I.; Christides, J. P.; Mandon, N.; Haffner, T.; Kahane, R.; Auger, J. High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipeptide precursors in garlic products using multiple mass spectrometry and UV detection. J. Chromatogr. A 2003, 991, 69-75.
22. Lawson, L. D.; Gardner, C. D. Composition, stability, and bioavailability of garlic products used in a clinical trial. J. Agric. Food Chem. 2005, 53, 6254-6261.
23. Arnault, I.; Haffner, T.; Siess, M. H.; Vollmar, A.; Kahane, R.; Auger, J. Analytical method for appreciation of garlic therapeutic potential and for validation of a new formulation. J. Pharm. Biomed. Anal. 2005, 37, 963-970.
24. Kubec, R.; Svobodova, M.; Velisek, J. Gas chromatographic determination of S-alk(en)ylcysteine sulfoxides. J. Chromatogr. A 1999, 862, 85-94.
25. Lancaster, J. E.; Kelly, K. E. Quantitative analysis of the S-alk(en)yl-L-cysteine sulphoxides in onion (Allium cepa L.). J. Sci. Food Agric. 1983, 34, 1229-1235.
26. Keusgen, M.; Junger, M.; Krest, I.; Schoning, M. Development of a biosensor specific for cysteine sulfoxides. J. Biosens. Bioelectron. 2003, 18, 805-812.
27. Synge, R. L. M.; Wood, J. C. (+)-(S-Methyl-L-cysteine S-oxide) in cabbage. Biochem. J. 1956, 64, 252-259.
28. Sakai, K.; Yoneda, N. Convenient synthesis of 1,4-thiazane-3-carboxylic acid derivatives. Chem. Pharm. Bull. 1981, 29, 1554-1560.
29. Shen, C.; Parkin, K. L. In vitro biogeneration of pure thiosulfinates and propanethial-S-oxide. J. Agric. Food Chem. 2000, 48, 6254-6260.
30. Lawson, L. D.; Hughes, B. G. Characterization of the formation of allicin and other thiosulfinates from garlic. Planta Med. 1992, 58, 345-350.