First insights into the mode of action of a "lachrymatory factor synthase" - Implications for the mechanism of lachrymator formation in Petiveria alliacea, Allium cepa and Nectaroscordum species

Phytochemistry

Volumn 72, Issue 16, 2011, Pages 1939-1946

  He, Quan ^a   Kubec, Roman ^b   Jadhav, Abhijit P ^a   Musah, Rabi A ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF SOUTH BOHEMIA   (Czech Republic)

Author keywords

1 Butenesulfenic acid isomerase; 1 Propenesulfenic acid isomerase; Homoisoalliin; Isoalliin; Lachrymatory factor synthase; Onion; Petiveria alliacea; Petiveriin; Phenylmethanesulfenic acid dehydrogenase; Phytolaccaceae; Sulfenic acid; Sulfenic acid dehydrogenase; Sulfenic acid isomerase; Sulfine

Indexed keywords

ISOMERASE; LACHRYMATORY FACTOR SYNTHASE, ALLIUM CEPA; OXIDOREDUCTASE; SULFENIC ACID DERIVATIVE; VEGETABLE PROTEIN;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; KINETICS; LILIACEAE; METABOLISM; PHYTOLACCACEAE; SPECIES DIFFERENCE;

INTRAMOLECULAR OXIDOREDUCTASES; KINETICS; LILIACEAE; OXIDOREDUCTASES; PHYTOLACCACEAE; PLANT PROTEINS; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY; SULFENIC ACIDS;

ALLIUM CEPA; NECTAROSCORDUM; PETIVERIA ALLIACEA; PHYTOLACCACEAE;

EID: 80052929508     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.07.013     Document Type: Article

References (24)

1. E. Block The organosulfur chemistry of the genus Allium - implications for the organic chemistry of sulfur Angew. Chem. Int. Ed. Engl. 31 1992 1135 1178
2. E. Block Garlic and Other Alliums: The Lore and the Science 2010 Royal Society of Chemistry Cambridge, UK
3. E. Block, E.J. Dane, S. Thomas, and R.B. Cody Applications of direct analysis in real time mass spectrometry (DART-MS) in Allium chemistry. 2-Propenesulfenic and 2-propenesulfinic acids, diallyl trisulfane S-oxide, and other reactive sulfur compounds from crushed garlic and other Alliums J. Agric. Food Chem. 58 2010 4617 4625
4. E. Block, J.Z. Gillies, C.W. Gillies, A.A. Bazzi, D. Putman, L.K. Revelle, D. Wang, and X. Zhang Allium chemistry: microwave spectroscopic identification, mechanism of formation, synthesis, and reactions of (E,Z)-propanethial S-oxide, the lachrymatory factor of the onion (Allium cepa) J. Am. Chem. Soc. 118 1996 7492 7501 (Pubitemid 26279804)
5. M.H. Brodnitz, and J.V. Pascale Thiopropanal S-oxide: a lachrymatory factor in onions J. Agric. Food Chem. 19 1971 269 272
6. A.J. Curtis, M.C. Shirk, and R. Fall Allylic or benzylic stabilization is essential for catalysis by bacterial benzyl alcohol dehydrogenases Biochem. Biophys. Res. Commun. 259 1999 220 223 (Pubitemid 29264021)
7. F.A. Davis, and R.L. Billmers Chemistry of sulfenic acids. 6. Structure of simple sulfenic acids generated by flash vacuum pyrolysis J. Org. Chem. 50 1984 2593 2595
8. C.C. Eady, T. Kamoi, M. Kato, N.G. Porter, S. Davis, M. Shaw, A. Kamoi, and S. Imai Silencing onion lachrymatory factor synthase causes a significant change in the sulfur secondary metabolite profile Plant Physiol. 147 2008 2096 2106 (Pubitemid 352844248)
9. K. Goto, M. Holler, and R. Okazaki Synthesis, structure, and reactions of a sulfenic acid bearing a novel bowl-type substituent: the first synthesis of a stable sulfenic acid by direct oxidation of a thiol J. Am. Chem. Soc. 119 1997 1460 1461 (Pubitemid 27122079)
10. He, Q., 2010. The alliinase and lachrymatory factor synthase systems in Petiveria alliacea. Ph.D. Thesis, State University of New York at Albany, Albany, NY, USA.
11. S. Imai, N. Tsuge, M. Tomotake, Y. Nagatome, H. Sawada, T. Nagata, and H. Kumagai An onion enzyme that makes the eyes water Nature 419 2002 685 (Pubitemid 35177945)
12. A. Ishii, K. Komiya, and J. Nakayama Synthesis of a stable sulfenic acid by oxidation of a sterically hindered thiol (thiophenetryptycene-8-thiol) and its characterization J. Am. Chem. Soc. 118 1996 12836 12837 (Pubitemid 27042014)
13. R. Kubec, R.B. Cody, A.J. Dane, R.A. Musah, J. Schraml, A. Vattekkatte, and E. Block Applications of direct analysis in real time-mass spectrometry (DART-MS) in Allium chemistry. (Z)-Butanethial S-oxide and 1-butenyl thiosulfinates and their S-(E)-1-butenylcysteine S-oxide precursor from Allium siculum J. Agric. Food Chem. 58 2010 1121 1128
14. R. Kubec, S. Kim, and R.A. Musah S-Substituted cysteine derivatives and thiosulfinate formation in Petiveria alliacea - part II Phytochemistry 61 2002 675 680 (Pubitemid 35386549)
15. R. Kubec, S. Kim, and R.A. Musah The lachrymatory principle of Petiveria alliacea Phytochemistry 63 2003 37 40 (Pubitemid 36427437)
16. R. Kubec, and R.A. Musah Cysteine sulfoxide derivatives in Petiveria alliacea Phytochemistry 58 2001 981 985 (Pubitemid 33086227)
17. J.E. Lancaster, and H.A. Collin Presence of alliinase in isolated vacuoles and of alkyl cysteine sulfoxides in the cytoplasm of bulbs of onion (Allium cepa) Plant Sci. Lett. 22 1981 169 176
18. R.A. Musah, Q. He, and R. Kubec Discovery and characterization of a novel lachrymatory factor synthase (LFS) in Petiveria alliacea and its influence on alliinase-mediated formation of biologically active organosulfur compounds Plant Physiol. 151 2009 1294 1303
19. R.A. Musah, Q. He, R. Kubec, and A. Jadhav Studies of a novel cysteine sulfoxide lyase from Petiveria alliacea: the first heteromeric alliinase Plant Physiol. 151 2009 1304 1316
20. N. Pelloux-Léon, R. Arnaud, J.L. Ripoll, P. Beslin, and Y. Vallée Thioacrolein S-oxide Tetrahedron Lett. 38 1997 1385 1388 (Pubitemid 27085520)
21. R.E. Penn, E. Block, and L.K. Revelle Flash vacuum pyrolysis studies. 5. Methanesulfenic acid J. Am. Chem. Soc. 100 1978 3622 3623
22. I.J. Pickering, E.Y. Sneeden, R.C. Prince, E. Block, H.H. Harris, G. Hirsch, and G.N. George Localizing the chemical forms of sulfur in vivo using X-ray fluorescence spectroscopic imaging: application to onion (Allium cepa) tissues Biochemistry 48 2009 6846 6853
23. C. Shen, and K.L. Parkin In vitro biogeneration of pure thiosulfinates and propanethial-S-oxide J. Agric. Food Chem. 48 2000 6254 6260 (Pubitemid 32056872)
24. V.A. Soloshonok, X. Tang, and V.J. Hruby Large-scale asymmetric synthesis of novel sterically constrained 2′,6′-dimethyl- and α,2′,6′-trimethyltyrosine and phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine Tetrahedron 57 2001 6375 6382 (Pubitemid 32709656)