Biotransformation of C13-norisoprenoids and monoterpenes by a cell suspension culture of cv. Gamay (Vitis vinifera)

Plant Cell, Tissue and Organ Culture

Volumn 97, Issue 2, 2009, Pages 203-213

  Mathieu, Sandrine ^a   Wirth, Jérémie ^b   Sauvage, François Xavier ^b   Lepoutre, Jean Paul ^b   Baumes, Raymond ^b   Gunata, Ziya ^a  

^a UMR QUALISUD   (France)

^b SPO   (France)

Author keywords

Ionone; C13 norisoprenoids; Grape cell culture; Monoterpenes; Vitis vinifera

Indexed keywords

C13-NORISOPRENOIDS; CELL SUSPENSION CULTURES; CYCLOHEXANE RINGS; GLYCOSYLATED; GRAPE CELL CULTURE; MONOTERPENES; SIDE CHAINS; VITIS VINIFERA;

CELL CULTURE;

VITACEAE; VITIS VINIFERA;

EID: 63949086627     PISSN: 01676857     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11240-009-9516-z     Document Type: Article

References (56)

1. AJ Aasen B Kimland SO Almquist CR Enzell 1972 New tobacco constituents-the structures of five isomeric megastigmatrienones Acta Chem Scand 26 2573 2576 10.3891/acta.chem.scand.26-2573
2. Abbott NA, Coombe BG, Sefton MA, Williams PJ (1990) Composition of Shiraz grapes in relation to the quality of table wines. In: Ribéreau-Gayon P, Lonvaud A (eds) Actualités oenologiques 1989. Paris, Dunod, pp 94-99
3. A Aharoni AP Giri S Deuerlein F Griepink W Jan de Kogel FWA Verstappen HA Verhoeven MA Jongsma W Schwab HJ Bouwmeester 2003 Terpenoid metabolism in wild-type and transgenic arabidopsis plants Plant Cell 15 2866 2884 10.1105/tpc.016253
4. C Ambid M Moisseeff J Fallot 1982 Biogenesis of monoterpenes. Bioconversion of citral by a cell suspension culture of Muscat grapes Plant Cell Rep 1 91 93 10.1007/BF00272360
5. C Ambid M Moisseeff J Fallot 1983 Interconversion des aldéhydes et des alcohols monoterpéniques par des cellules de raisin Muscat cultivées in vitro Physiol Veg 21 87 92
6. Banthorpe DV, Charlood BV (1980) The terpenoids. In: Bell EA, Charlwood BV (eds) Encyclopedia of plant physiology. Secondary plant products. Springer-Verlag, Berlin, pp 185-220
7. RL Baumes CC Aubert Z Gunata W De Moor CL Bayonove C Tapiero 1994 Structures of two glucosidic C13-norisoprenoids precursors of wine flavor J Ess Oil Res 6 587 599
8. RG Berger Z Akkan F Drawert 1990 Catabolism of geraniol by cell suspension cultures of Citrus lemon Biochim Biophys Acta 1055 234 239 10.1016/0167-4889(90)90038-F
9. G Bock I Benda P Scheier 1986 Metabolism of linalool by Botrytis cinerea. Biotransformation J Food Sci 51 659 662 10.1111/j.1365-2621.1986.tb13904.x
10. G Bock I Benda P Scheier 1988 Microbial transformation of geraniol and nerol by Botrytis cinerea Appl Microbiol Biotechnol 27 351 357 10.1007/BF00251767
11. F Bouvier C Suire J Mutterer B Camara 2003 Oxidative remodeling of chromoplast carotenoids: identification of the carotenoid dioxygenase CsCCD and CsZCD genes involved in crocus secondary metabolites biogenesis Plant Cell 15 47 62 10.1105/tpc.006536
12. B Bravdo R Shoseyov R Ikan A Altman 1990 Monoterpene glycoside biosynthesis in detached grape berries grown in vitro Physiol Plant 78 93 99 10.1111/j.1399-3054.1990.tb08720.x
13. P Brunnerie J Benda G Bock P Schreier 1987 Bioconversion of citronellol by Botrytis cinerea Appl Microbiol Biotechnol 27 6 10 10.1007/BF00257245
14. OA Colom S Popich A Bardon 2007 Bioactive constituents from Rollinia emarginata (Annonaceae) Nat Prod Res 21 254 259
15. F Cormier C Ambid 1987 Extractive bioconversion of geraniol by Vitis vinifera cell suspension employing a two-phase system Plant Cell Rep 6 427 430
16. JC Demyttenaere HM Willemn 1998 Biotransformation of linalool to furanoid and pyranoid linalool oxides by Aspergillus niger Phytochem 47 1029 1036 10.1016/S0031-9422(97)00688-2
17. T Fester W Maier D Strack 1999 Accumulation of secondary compounds in barley and wheat roots in response to inoculation with an arbuscural mycorrhizal fungus and coinoculation with rhizosphere bacteria Mycorrhiza 8 241 246 10.1007/s005720050240
18. OL Gamborg DE Eveleigh 1968 Cultures methods and detection of glycanases in suspension cultures of wheat and barley Can J Biochem 46 417 421
19. J Guardiola JL Iborra L Rodenas M Canovas 1996 Biotransformation from geraniol to nerol by immobilized grapevine cells (Vitis vinifera) Appl Biochem Biotechnol 56 169 180 10.1007/BF02786947
20. Gunata Z, Dugelay I, Sapis JC, Baumes RL, Bayonove C (1993) Role of enzymes in the use of flavor potential from grape glycosides in winemaking. In: Schreier P, Winterhalter P (eds) Progress in flavor precursor studies. Allured, Wheaton, pp 219-234
21. S Hasegawa SM Poling VP Maier RD Bennett 1984 Metabolism of abscisic acid: bacterial conversion to dehydrovomifoliol and vomifoliol dehydrogenase activity Phytochem 23 2769 2771 10.1016/0031-9422(84)83012-5
22. M Ibdah Y Azulay V Portnoy B Wasserman E Bar A Meir Y Burger J Hirschberg AA Schaffer N Katzir Y Tadmor E Lewinsohn 2006 Functional characterization of CmCCD1, a carotenoid cleavage dioxygenase from melon Phytochem 67 1579 1589 10.1016/j.phytochem.2006.02.009
23. F Karp CA Mihaliak JL Harris R Croteau 1990 Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves Arch Biochem Biophys 276 219 226 10.1016/0003-9861(90)90029-X
24. M Kato H Matsumoto Y Ikoma H Okuda M Yano 2006 The role of carotenoid cleavage dioxygenases in the regulation of carotenoid profiles during maturation in citrus fruit J Exp Bot 57 2153 2164 10.1093/jxb/erj172
25. H Kato-Noguchi 1992 An endogenous growth inhibitor, 3-hydroxy-ß- ionone. I. Its role in light-induced growth inhibition of hypocotyls of Phaseolus vulgaris Physiol Plant 86 583 586 10.1111/j.1399-3054.1992.tb02173.x
26. V Krasnobajew D Helmlinger 1982 Fermentation of fragrances: biotransformation of β-ionone by Lasodiplodia theobromae Helv Chim Acta 65 1590 1601 10.1002/hlca.19820650532
27. Larroche C, Grivel F, Creuly C, Gros JB (1995) Bioflavour 95. In: Etiévant P, Schreier P (eds) INRA, Paris, pp 309-314
28. HK Lichtenthaler M Rohmer J Schwender 1997 Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants Physiol Plant 101 643 652 10.1111/j.1399-3054.1997.tb01049.x
29. Little DB, Croteau RB (1999) Biochemistry of essential oil terpenes. A thirty year overview. In: Teranishi R (ed) Flavor chemistry: 30 years of progress. Kluwer Academic/Plenum Publishers, New York, pp 238-253
30. F Luan D Hampel M Mosandl M Wüst 2004 Enantioselective analysis of free and glycosidically bound monoterpene polyols in Vitis vinifera L. cvs. Morio Muscat and Muscat Ottonel J Agric Food Chem 52 2036 2041 10.1021/jf030701q
31. F Luan A Mosandl A Münch M Wüst 2005 Metabolism of geraniol in grape berry mesocarp of Vitis vinifera L. cv. Scheurebe: demonstration of stereoseletive reduction, E/Z-isomerisation oxidation and glycosylation Phytochem 66 295 303 10.1016/j.phytochem.2004.12.017
32. J Marais 1983 Terpenes in the aroma of grapes and wines: a review S Afr J Enol Vitic 4 49 58
33. 13- norisoprenoid accumulation J Exp Bot 56 2721 2731 10.1093/jxb/eri265
34. G Morel 1970 Le problème de la transformation tumorale chez les végétaux Physiol Veg 8 189 191
35. T Murashige F Skoog 1962 A revised medium for rapid growth and bioassays with tobacco tissue cultures Physiol Plant 15 473 497 10.1111/j.1399-3054.1962. tb08052.x
36. Paissarnrat S, Ambid C (1985) Topics in Flavour Research. In: Berger RG, Nitz S, Schreier P (eds) Proceedings of the International Conference Marzling-Hangenham H Eichhorn, Freising-Weihenstephan D-8051, pp 321-333
37. SH Park SU Kim 1998 Modified monoterpenes from biotransformation of (-)isopiperitinone by suspension cell culture of Mentha piperita J Nat Prod 61 354 357 10.1021/np970388k
38. Rapp A, Mandery H (1988) Analysis-biochemistry-biotechnology. In: Schreier P (ed) Bioflavor 87. Berlin, W. de Gruyter, pp 445-454
39. N Sakui M Kuroyanagi Y Ishitobi M Sato A Keno 1992 Biotransformation of sesquiterpenes by cells of Curcuma zedoaria Phytochem 31 143 147
40. Sarry JE (2001) Etude biochimique et moléculaire de β-d-glucoside hydrolases de la baie de raisin (Vitis vinefera L.). PhD. Thesis. University Montpellier II, Montpellier, France
41. SH Schwartz X Qin JA Zeevart 2001 Characterization of a novel carotenoid cleavage dioxygenase from plants J Biol Chem 276 25208 25211 10.1074/jbc.M102146200
42. SH Schwartz X Qin MC Loewen 2004 The biochemical characterization of two carotenoid cleavage enzymes from Arabidopsis indicates that a carotenoid-derived compound inhibits lateral branching J Biol Chem 279 46940 46945 10.1074/jbc.M409004200
43. MA Sefton GK Skouroumounis RA Massy-Westropp PJ Williams 1989 Norisoprenoids in Vitis vinifera white wine grapes and the identification of a precursor of damascenone in these fruits Aust J Chem 42 2071 2084
44. KB Shure TE Acree 1994 Production of β-damascenone precursors in cell culture of Vitis vinifera labrusca cv. Concord grapes Plant Cell Rep 13 477 480 10.1007/BF00231971
45. AJ Simkin SH Schwartz M Auldridge MG Taylor HJ Klee 2004 The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles β-ionone, pseudoionone, and geranylacetone Plant J 40 882 892 10.1111/j.1365-313X.2004.02263.x
46. AJ Simkin BA Underwood M Auldridge HM Loucas K Shibuya E Schmelz DG Clark HJ Klee 2004 Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of β-ionone, a fragance volatile of petunia flowers Plant Physiol 136 3504 3514 10.1104/pp.104.049718
47. AJ Simkin H Moreau M Kuntz G Pagny C Lin S Tanksley J McCarthy 2008 An investigation of carotenoid biosynthesis in Coffea canephora and Coffea arabica J Plant Physiol 165 1087 1106 10.1016/j.jplph.2007.06.016
48. GK Skouroumounis RA Massy-Westropp MA Sefton PJ Williams 1992 Precursors of damascenone in fruit juices Tetrahedron Lett 33 3533 3536 10.1016/S0040-4039(00)92682-0
49. CR Strauss B Wilson PJ Williams 1987 3-oxo-α-ionol, vomifoliol and roseoside in Vitis vinifera fruit Phytochem 26 1995 1997 10.1016/S0031-9422(00) 81745-8
50. T Suga T Hirata 1990 Biotransformation of exogenous substrates by plant cell cultures Phytochem 29 2393 2406 10.1016/0031-9422(90)85155-9
51. Y Tang T Suga 1994 Biotransformation of α- and β-ionones by immobilized cells of Nicotiana tabacum Phytochem 37 737 740 10.1016/S0031- 9422(00)90349-2
52. Williams PJ, Sefton MA, Wilson B (1989) Non-volatile conjugates of secondary metabolites as precursors of varietal grape flavor components. In: Teranishi R, Buttery RG, Shahidi F (eds) Flavor chemistry trends and development. American Chemical Society, Washington, DC, pp 35-48
53. Winterhalter P, Rouseff R (2002) Carotenoid-derived aroma compounds: an introduction. In: Winterhalter P, Rouseff RL (eds) Carotenoid derived aroma compounds. American Chemical Society, Washington, DC, pp 1-19
54. 13-norisoprenoid glycosides in plant tissues: an overview on their occurence, composition and role as flavour precursors Flavour Frag J 9 281 287 10.1002/ffj.2730090602
55. Winterhalter P, Knapp H, Straubinger M, Fornari S, Watanabe N (1998) Application of countercurrent chromatography to the analysis of aroma precursors in rose flowers. In: Mussinan CJ, Morello MJ (eds) Challenges in isolation and characterization of flavour compounds. American Chemical Society, Washington, DC, pp 181-192
56. J Wirth W Guo RL Baumes Z Gunata 2001 Volatile compounds released by enzymatic hydrolysis of glycoconjugates of leaves and grape berries from Vitis vinifera Muscat of Alexandria and Shiraz cultivars J Agric Food Chem 49 2917 2923 10.1021/jf001398l