Nonvolatile S-Alk(en)ylthio-l-cysteine derivatives in fresh onion (Allium cepa L. cultivar)

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 17, 2011, Pages 9457-9465

  Starkenmann, Christian ^a   Niclass, Yvan ^a   Troccaz, Myriam ^a  

^a Analysis and Perception Department   (Switzerland)

Author keywords

alk(en)ylthio L cysteine; Allium cepa L.; apotryptophanase; Fusobacterium nucleatum

Indexed keywords

ALK(EN)YLTHIO-L-CYSTEINE; ALLIUM CEPA; APOTRYPTOPHANASE; DIFFERENT PRECURSORS; FUSOBACTERIUM NUCLEATUM; ISOALLIIN; L-ALANINE; L-CYSTEINE; NON-VOLATILE; PLANT ENZYMES; PROPANOIC ACID; VOLATILE SULFUR COMPOUNDS;

CHLORINE COMPOUNDS; ENZYMES; FLAVOR COMPOUNDS; SATURATED FATTY ACIDS; SULFUR; SULFUR COMPOUNDS;

AMINO ACIDS;

ALLIIN; ALLIIN LYASE; CYSTEINE; DISULFIDE; DRUG DERIVATIVE; LYASE; SULFUR DERIVATIVE; VOLATILE ORGANIC COMPOUND;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FUSOBACTERIUM NUCLEATUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; MICROBIOLOGY; MOUTH; ODOR; ONION; PLANT ROOT;

CARBON-SULFUR LYASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTEINE; DISULFIDES; FUSOBACTERIUM NUCLEATUM; MOUTH; ODORS; ONIONS; PLANT ROOTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFUR COMPOUNDS; VOLATILE ORGANIC COMPOUNDS;

ALLIUM CEPA; FUSOBACTERIUM NUCLEATUM;

EID: 80052601614     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf202082f     Document Type: Article

References (40)

1. Block, E. Garlic and Other Alliums. The Lore and the Science; Royal Society of Chemistry: Cambridge, U.K., 2010.
2. Kuettner, E. B.; Hilgenfeld, R.; Weiss, M. S. The active principle of garlic at atomic resolution J. Biol. Chem. 2002, 277, 46402-46407 (Pubitemid 35417634)
3. Cavallito, J.; Buck, J. S.; Suter, C. M. Allicin, the antibacterial principle of Allium sativum. II. Determination of the chemical structure J. Am. Chem. Soc. 1944, 66, 1952-1954
4. Dini, I.; Tenore, G. C.; Dini, A. Chemical composition, nutritional value and antioxidant properties of Allium cepa L. var. tropeana (red onion) seeds Food Chem. 2008, 107, 613-621 (Pubitemid 350116362)
5. Zhang, G.; Li, B.; Lee, C.-H.; Parkin, K. L. Cysteine and glutathione mixed-disulfide conjugates of thiosulfinates: chemical synthesis and biological activities J. Agric. Food Chem. 2010, 58, 1564-1571
6. Block, E.; Naganathan, S.; Putman, D.; Zhao, S. H. Allium chemistry: HPLC analysis of thiosulfinates from onion, garlic, wild garlic (ramsoms), leek, scallion, shallot, elephant (great-headed) garlic, chive, and Chinese chive. Uniquely high allyl to methyl ratios in some garlic samples J. Agric. Food Chem. 1992, 40, 2418-2430
7. Starkenmann, C.; Le Calvé, B.; Niclass, Y.; Cayeux, I.; Beccucci, S.; Troccaz, M. Olfactory perception of cysteine- S -conjugates from fruits and vegetables J. Agric. Food Chem. 2008, 56, 9575-9580
8. Lüntzel, C. S.; Widder, S.; Vössing, T.; Pickenhagen, W. Enantioselective syntheses and sensory properties of the 3-mercapto-2- methylpentanols J. Agric. Food Chem. 2000, 48, 424-427 (Pubitemid 30120377)
9. Starkenmann, C.; Niclass, Y.; Cayeux, I. Occurrence of l -γ-glutamyl- S -(1-hydroxy-2-methyl-3-pentanyl)- l -cysteine and S -(1-ethyl-3-hydroxy-2-methylpropyl)- l -cysteine in fresh and processed Allium caepa L. cultivar. Flavour Fragrance J. 2010, 26, DOI: 10.1002/ffj.2048.
10. Takeshita, T.; Suzuki, N.; Nakano, Y.; Shimazaki, Y.; Yoneda, M.; Hirofuji, T.; Yamashita, Y. Relationship between oral malodor and the global composition of indigenous bacterial population in saliva Appl. Environ. Microbiol. 2010, 76, 2806-2814
11. Donaldson, A. C.; McKenzie, D.; Riggio, M. P.; Hodge, P. J.; Rolph, H.; Flanagan, A.; Bagg, J. Microbiological culture analysis of the tongue anaerobic microflora in subjects with and without halitosis Oral Dis. 2005, 11 (Suppl. S1) 61-63 (Pubitemid 44944437)
12. Kazor, C. E.; Mitchell, P. M.; Lee, A. M.; Stokes, L. N.; Loesche, W. J.; Dewhirst, E.; Paster, B. J. Diversity of bacterial populations on the tongue dorsa of patients with halitosis and healthy patients J. Clin. Microbiol. 2003, 41, 558-563 (Pubitemid 36184161)
13. Senpuku, H.; Tada, A.; Yamaga, T.; Hanada, N.; Miyazaki, H. Relationship between volatile sulphide compounds concentration and oral bacteria species detection in the elderly Int. Dent. J. 2004, 54, 149-153 (Pubitemid 39194124)
14. Loesche, W. J.; Kazor, C. Microbiology and treatment of halitosis Periodontology 2002, 28, 256-279
15. Rietman, B. H.; Peters, R. F. R; Tesser, G. I. A facile method for the preparation of S -(alkylsulfenyl)cysteines Synth. Commun. 1994, 24, 1323-1332
16. Block, E.; Thiruvazhi, M. Allium chemistry: synthesis of alk(en)yl 3,4,-dimethyl-2-thienyl disulfides, components of distilled oils and extracts of Allium species J. Agric. Food Chem. 1993, 41, 2235-2237
17. Stoll, A.; Seebeck, E. Über Alliin, die genuine Muttersubstanz des Knoblauchöls. 1. Mitteilung über Allium-Substanzen Helv. Chim. Acta 1948, 31, 189-210
18. Stoll, A.; Seebeck, E. Die Synthese des natürlichen Alliins und seiner drei optisch aktiven Isomeren. 5. Mitteilung über Allium-Substanzen Helv. Chim. Acta 1951, 34, 481-487
19. Lessene, G. L.; Baell, J. Preparation of amino acid derivatives as α-helical mimetics. U.S. Pat. Appl. Publ. 20080153802, June 26, 2008.
20. Tsuge, K.; Kataoka, M.; Seto, Y. Determination of S -methyl-, S -propyl-, and S -propenyl- l -cysteine sulfoxides by gas chromatography-mass spectrometry after tert -butyldimethylsilylation J. Agric. Food Chem. 2002, 50, 4445-4451 (Pubitemid 34823963)
21. Nishimura, H.; Mizuguchi, A.; Hizutani, J. Stereoselective synthesis of S-(trans -prop-1-enyl)-cysteine sulphoxide Tetrahedron Lett. 1975, 16, 3201-3202
22. Stoll, A; Seebeck, E. Über die Spezifitt und die Synthese mehrerer dem Alliin verwandter Verbindungen. 3. Mitteilung über Allium-Substanzen Helv. Chim. Acta 1949, 32, 866-876
23. Sharma, K.; Laurens, J. B.; Pilcher, L. A. Stereoselective synthesis of the urinary metabolite N -acetyl- S -(3,4-dihydroxybutyl)cysteine Synth. Commun. 2009, 39, 1415-1424
24. 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 (Pubitemid 30019232)
25. Rabinkov, A.; Miron, T.; Mirelman, D.; Wilchek, M.; Glozman, S.; Yavin, E.; Weiner, L. S -Allylmercaptoglutathione: the reaction product of allicin with glutathione possesses SH-modifying and antioxidant properties Biochim. Biophys. Acta 2000, 1499, 144-153
26. Lawson, L. D.; Wang, Z. J. Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability J. Agric. Food Chem. 2005, 53, 1974-1983 (Pubitemid 40395761)
27. Fritsch, R. M.; Keusgen, M. Occurrence and taxonomic significance of cysteine sulfoxides in the genus Allium L. (Alliaceae) Phytochemistry 2006, 67, 1127-1135 (Pubitemid 43818031)
28. 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
29. Riggio, M. P.; Lennon, A.; Rolph, H. J.; Hodge, P. J.; Donaldson, A.; Maxwell, A. J.; Bagg, J. Molecular identification of bacteria on the tongue dorsum of subjects with and without halitosis Oral Dis. 2008, 14, 251-258 (Pubitemid 351379709)
30. Tonzetich, J.; Richter, V. J. Evaluation of volatile odoriferous components of saliva Arch. Oral Biol. 1964, 9, 39-45
31. Washio, J.; Sato, T.; Koseki, T.; Takahashi, N. Hydrogen sulfide-producing bacteria in tongue biofilm and their relationship with oral malodour J. Med. Microbiol. 2005, 54, 889-895 (Pubitemid 41216288)
32. Kleinberg, I.; Westbay, G. Oral malodor Oral Biol. Med. 1990, 1, 247-259 (Pubitemid 20361897)
33. Almstahl, A.; Wikstrom, M. Oral microflora in subjects with reduced salivary secretion J. Dent. Res. 1999, 78, 1410-1416 (Pubitemid 32511511)
34. Tominaga, T.; Peyrot des Gachons, C.; Dubourdieu, D. A new type of flavor precursors in Vitis vinifera L. cv. Sauvignon Blanc: S -cysteine conjugates J. Agric. Food Chem. 1998, 46, 5215-5219 (Pubitemid 128488285)
35. Lancaster, J. E.; Shaw, M. L.; Pither Joyce, M. D.; McCallum, J. A.; McManus, M. T. Plant Physiol. 2000, 122, 1269-1279
36. Cooper, A. J. L.; Pinto, J. T. Aminotransferase, l -amino acid oxidase and β-lyase reactions involving l -cysteine S -conjugates found in allium extracts: relevance to biological activity? Biochem. Pharmacol. 2005, 69, 209-220 (Pubitemid 41556567)
37. Pinto, J. T.; Krasnikov, B. F.; Cooper, A. J. L. Redox-sensitive proteins are potential targets of garlic-derived mercaptocysteine derivatives J. Nutr. 2006, 136, 835S-841S (Pubitemid 43363788)
38. Han, J.; Lawson, L.; Han, G. A.; Han, P. A spectrophotometric method for quantitative determination of allicin and total garlic thiosulfinates Anal. Biochem. 1995, 225, 157-160
39. Cooper, A. J. L.; Pinto, J. T. Cysteine S -conjugate β-lyases Amino Acids 2006, 30, 1-15
40. Cooper, A. J. L. Mechanisms of cysteine- S -conjugate β-lyases. In Advances in Enzymology and Related Areas of Molecular Biology: Amino Acid Metabolism, Part A; Purich, D. L., Ed.; Wiley: Hoboken, NJ, 1998; Vol. 72, pp 199-238.