3-slfanylhexanol precursor biogenesis in grapevine cells: The stimulating effect of botrytis cinerea

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 4, 2011, Pages 1344-1351

  Thibon, Cécile ^a   Cluzet, Stéphanie ^a   Mérillon, Jean Michel ^a   Darriet, Philippe ^a   Dubourdieu, Denis ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

(E) 2 hexenal; cysteinylated conjugates; glutathione; glutathionylated conjugates; noble rot; thiol precursor; Vitis vinifera

Indexed keywords

AMINO ACIDS; CELL CULTURE; FRUITS; PEPTIDES; WINE;

(E)-2-HEXENAL; CYSTEINYLATED CONJUGATES; GLUTATHIONES; GLUTATHIONYLATED CONJUGATES; NOBLE ROT; THIOL PRECURSOR; VITIS VINIFERA;

CELLS;

BOTRYOTINIA FUCKELIANA; FUNGI; VITACEAE; VITIS; VITIS VINIFERA;

3 MERCAPTOHEXANOL; 3-MERCAPTOHEXANOL; CYSTEINE; DRUG DERIVATIVE; GLUTATHIONE; HEXANOL; THIOL DERIVATIVE;

ARTICLE; BOTRYTIS; CELL CULTURE; CHEMISTRY; COCULTURE; CYTOLOGY; FRUIT; GRAPE; METABOLISM; MICROBIOLOGY; ODOR; PHYSIOLOGY; PLANT STEM; WINE;

BOTRYTIS; CELLS, CULTURED; COCULTURE TECHNIQUES; CYSTEINE; FRUIT; GLUTATHIONE; HEXANOLS; ODORS; PLANT STEMS; SULFHYDRYL COMPOUNDS; VITIS; WINE;

EID: 79951763140     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf103915y     Document Type: Article

References (33)

1. Bailly, S.; Jerkovic, V.; Marchand-Brynaert, J.; Collin, S. Aroma extraction dilution analysis of sauternes wines. Key role of polyfunctional thiols J. Agric. Food Chem. 2006, 54 (19) 7227-7234 (Pubitemid 44554945)
2. Bailly, S.; Jerkovic, V.; Meuree, A.; Timmermans, A.; Collin, S. Fate of key odorants in sauternes wines through aging J. Agric. Food Chem. 2009, 57 (18) 8557-8563
3. Sarrazin, E.; Shinkaruk, S.; Tominaga, T.; Bennetau, B.; Frerot, E.; Dubourdieu, D. Odorous impact of volatile thiols on the aroma of young botrytized sweet wines: identification and quantification of new sulfanyl alcohols J. Agric. Food Chem. 2007, 55 (4) 1437-44
4. Tominaga, T.; Niclass, N.; Frérot, E.; Dubourdieu, D. Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (var. Sauvignon blanc and Semillon) J. Agric. Food Chem. 2006, 54 (19) 7251-7255 (Pubitemid 44554948)
5. Masneuf-Pomarede, I.; Mansour, C.; Murat, M. L.; Tominaga, T.; Dubourdieu, D. Influence of fermentation temperature on volatile thiols concentrations in Sauvignon blanc wines Int. J. Food Microbiol. 2006, 108 (3) 385-90 (Pubitemid 46137856)
6. Tominaga, T.; Baltenweck-Guyot, R.; Peyrot des Gachons, C.; Dubourdieu, D. Contribution of volatile thiols to the aromas of white wines made from several Vitis vinifera grape varieties Am. J. Enol. Vitic. 2000, 51, 178-181 (Pubitemid 30656749)
7. Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines Flavour Fragrance J. 1998, 13 (3) 159-162 (Pubitemid 28352101)
8. Luisier, J. L.; Buettner, H.; Volker, S.; Rausis, T.; Frey, U. Quantification of cysteine S-conjugate of 3-sulfanylhexan-1-ol in must and wine of petite arvine vine by stable isotope dilution analysis J. Agric. Food Chem. 2008, 56 (9) 2883-2887 (Pubitemid 351746003)
9. Murat, M. L.; Tominaga, T.; Dubourdieu, D. Assessing the aromatic potential of Cabernet Sauvignon and Merlot musts used to produce rose wine by assaying the cysteinylated precursor of 3-mercaptohexan-1-ol J. Agric. Food Chem. 2001, 49 (11) 5412-7 (Pubitemid 33089685)
10. Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Measuring the aromatic potential of Vitis vinifera L. Cv. Sauvignon blanc grapes by assaying S -cysteine conjugates, precursors of the volatile thiols responsible for their varietal aroma J. Agric. Food Chem. 2000, 48 (8) 3387-91
11. Thibon, C.; Shinkaruk, S.; Jourdes, M.; Bennetau, B.; Dubourdieu, D.; Tominaga, T. Aromatic potential of botrytized white wine grapes: Identification and quantification of new cysteine-S-conjugate flavor precursors Anal. Chim. Acta 2010, 660 (1-2) 190-196
12. Thibon, C.; Shinkaruk, S.; Tominaga, T.; Bennetau, B.; Dubourdieu, D. Analysis of the diastereoisomers of the cysteinylated aroma precursor of 3-sulfanylhexanol in Vitis vinifera grape must by gas chromatography coupled with ion trap tandem mass spectrometry J. Chromatogr., A 2008, 1183 (1-2) 150-157
13. Thibon, C.; Dubourdieu, D.; Darriet, P.; Tominaga, T. Impact of noble rot on the aroma precursor of 3-sulfanylhexanol content in Vitis vinifera L. cv Sauvignon blanc and Semillon grape juice Food Chem. 2009, 114 (4) 1359-1364
14. Grant-Preece, P. A.; Pardon, K. H.; Capone, D. L.; Cordente, A. G.; Sefton, M. A.; Jeffery, D. W.; Elsey, G. M. Synthesis of wine thiol conjugates and labeled analogues: Fermentation of the glutathione conjugate of 3-mercaptohexan-1-ol yields the corresponding cysteine conjugate and free thiol J. Agric. Food Chem. 2010, 58 (3) 1383-1389
15. Kobayashi, H.; Takase, H.; Kaneko, K.; Tanzawa, F.; Takata, R.; Suzuki, S.; Konno, K. Analysis of S-3-(hexan-1-ol)-glutathione and S-3-(hexan-1-ol)- l -cysteine in Vitis vinifera L. cv. Koshu for aromatic wines Am. J. Enol. Vitic. 2010, 61 (2) 176-185
16. Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Sulfur aroma precursor present in S -glutathione conjugate form: identification of S -3-(hexan-1-ol)-glutathione in must from Vitis vinifera L. cv. Sauvignon blanc J. Agric. Food Chem. 2002, 50 (14) 4076-9 (Pubitemid 34734316)
17. Roland, A.; Vialaret, J.; Razungles, A.; Rigou, P.; Schneider, R. Evolution of S-cysteinylated and S-glutathionylated thiol precursors during oxidation of Melon B. and Sauvignon blanc musts J. Agric. Food Chem. 2010, 58 (7) 4406-4413
18. Kishimoto, K.; Matsui, K.; Ozawa, R.; Takabayashi, J. Volatile C6-aldehydes and allo-ocimene activate defense genes and induce resistance against Botrytis cinerea in Arabidopsis thaliana Plant Cell Physiol. 2005, 46 (7) 1093-1102 (Pubitemid 41373473)
19. Mueller, M. J. Archetype signals in plants: the phytoprostanes Curr. Opin. Plant Biol. 2004, 7 (4) 441-448 (Pubitemid 38871619)
20. Jakoby, W. B.; Stevens, J.; Duffel, M. W.; Weisiger, R. A. The terminal enzymes of mercapturate formation and the thiomethyl shunt Rev. Biochem. Toxicol. 1984, 6, 97-115
21. Wolf, A. E.; Dietz, K. J.; Schroder, P. Degradation of glutathione S-conjugates by a carboxypeptidase in the plant vacuole FEBS Lett. 1996, 384 (1) 31-34 (Pubitemid 26111926)
22. Podolyan, A.; White, J.; Jordan, B.; Winefield, C. Identification of the lipoxygenase gene family from Vitis vinifera and biochemical characterisation of two 13-lipoxygenases expressed in grape berries of Sauvignon Blanc Funct. Plant Biol. 2010, 37 (8) 767-784
23. Hatanaka, A. The biogeneration of green odour by green leaves Phytochemistry 1993, 34 (5) 1201-1218 (Pubitemid 2019298)
24. Hamilton-Kemp, T. R.; Archbold, D. D.; Collins, R. W.; Yu, K. Emission patterns of wound volatile compounds following injury of ripe strawberry fruit J. Sci. Food Agric. 2003, 83 (4) 283-288 (Pubitemid 36280525)
25. Myung, K.; Hamilton-Kemp, T. R.; Archbold, D. D. Biosynthesis of trans-2-hexenal in response to wounding in strawberry fruit J. Agric. Food Chem. 2006, 54 (4) 1442-1448 (Pubitemid 43374240)
26. Thoma, I.; Loeffler, C.; Sinha, A. K.; Gupta, M.; Krischke, M.; Steffan, B.; Roitsch, T.; Mueller, M. J. Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants Plant J. 2003, 34 (3) 363-375 (Pubitemid 36579860)
27. Kobayashi, H.; Takase, H.; Suzuki, Y.; Tanzawa, F.; Takata, R.; Fujita, K.; Kohno, M.; Mochizuki, M.; Suzuki, S.; Konno, T. Environmental stress enhances biosynthesis of flavor precursors, S-3-hexan-1-ol)-glutathione and S-3-(hexan-1-ol)-L-cysteine, in grapevine through glutathione S-transferase activation J. Exp. Bot. 2010, 10.1093/jxb/erq376
28. Krisa, S.; Vitrac, X.; Decendit, A.; Larronde, F.; Deffieux, G.; Mérillon, J. M. Obtaining Vitis vinifera cell cultures producing higher amounts of malvidin-3-O-b-glucoside Biotechnol. Lett. 1999, 21 (6) 497-500 (Pubitemid 29349155)
29. Belhadj, A.; Saigne, C.; Telef, N.; Cluzet, S.; Bouscaut, J.; Corio-Costet, M. F.; Mérillon, J. M. Methyl jasmonate induces defense responses in grapevine and triggers protection against Erysiphe necator J. Agric. Food Chem. 2006, 54 (24) 9119-9125 (Pubitemid 44953610)
30. Belhadj, A.; Telef, N.; Saigne, C.; Cluzet, S.; Barrieu, F.; Hamdi, S.; Mérillon, J. M. Effect of methyl jasmonate in combination with carbohydrates on gene expression of PR proteins, stilbene and anthocyanin accumulation in grapevine cell cultures Plant Physiol. Biochem. 2008, 46 (4) 493-499
31. Faurie, B.; Cluzet, S.; Mérillon, J. M. Implication of signaling pathways involving calcium, phosphorylation and active oxygen species in methyl jasmonate-induced defense responses in grapevine cell cultures J. Plant Physiol. 2009, 166 (17) 1863-1877
32. Zamboni, A.; Gatto, P.; Cestaro, A.; Pilati, S.; Viola, R.; Mattivi, F.; Moser, C.; Velasco, R. Grapevine cell early activation of specific responses to DIMEB, a resveratrol elicitor BMC Genomics 2009, 10, 363
33. Gagné, S.; Cluzet, S.; Mérillon, J. M.; Gény, L. ABA initiates anthocyanin production in grape cell cultures J. Plant Growth Regul. 2010, 10.1007/s00344-010-9165-9