[en] Lipids are an important source of aroma compounds. In foods, lipids are degraded or modified by enzymatic activities that are originally present in the raw materials or that develop later due to the growth of microorganisms. Mimicking these natural pathways, some processes have been developed to produce aroma compounds in bioreactors. In this review we describe the production of aroma compounds from different families: lactones, green notes and ionones. We focus on points that are specific to these reactions in heterogeneous media: physicochemical forces involved in the interactions between the substrate, product and biocatalyst, transfers between the phases and, as the degradation of lipids often requires an oxidation step, on the problems of oxygenation of the reactors.
Disciplines :
Biotechnology
Author, co-author :
Aguedo, Mario ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Ly, M. H.; Lab. de Microbiologie UMR UB/INRA, Ecl. Natl. Sup. de Biol. Appl. A. N., Esplanade Erasme, F-21000 Dijon, France
Belo, I.; Ctro. de Engenheria Biológica, Universidade do Minho, Campus de Gualtar, P-4710-057 Braga, Portugal
Teixeira, J. A.; Ctro. de Engenheria Biológica, Universidade do Minho, Campus de Gualtar, P-4710-057 Braga, Portugal
Belin, J.-M.; Lab. de Microbiologie UMR UB/INRA, Ecl. Natl. Sup. de Biol. Appl. A. N., Esplanade Erasme, F-21000 Dijon, France
Waché, Y.; Lab. de Microbiologie UMR UB/INRA, Ecl. Natl. Sup. de Biol. Appl. A. N., Esplanade Erasme, F-21000 Dijon, France
Language :
English
Title :
The use of enzymes and microorganisms for the production of aroma compounds from lipids
A. Pandey, S. Benjamin, C. Soccol, P. Nigam, N. Krieger, V. Soccol, Biotechnol. Appl. Biochem. 29 (1999) 119-131.
U. Bornscheuer, Curr. Opin. Biotechnol. 13 (2002) 543-547.
K. Jaeger, T. Eggert, Curr. Opin. Biotechnol. 13 (2002) 390-397.
A. Mortensen, L. H. Skibsted, J. Agric. Food Chem. 48 (2000) 279-286.
P. Wintherhalter, R. Rouseff: Carotenoid-Derived Aroma Compounds: An Introduction. In: Carotenoid-Derived Aroma Compounds, P. Wintherhalter, R. Rouseff (Eds.), ACS, Washington DC (2001) pp. 1-17.
R. C. Mordi, J. C. Walton, G. W. Burton, L. Hughes, K. U. Ingold, D. A. Lindsay, Tetrahedron Lett. 32 (1991) 4203-4206.
T. A. Kennedy, D. C. Liebler, J. Biol. Chem. 267 (1992) 4658-4663.
J. Crouzet, P. Kanasawud, M. Sakho: Thermal Generation of Carotenoid-Derived Compounds. In: Carotenoid-Derived Aroma Compounds, P. Winterhalter, R. Rouseff (Eds.), ACS, Washington DC (2001) pp. 115-129.
P. Bonnie Ty, Y. M. Choo, J. Oil Palm Res. 2 (1999) 62-78.
H. Zorn, D. E. Breithaupt, M. Takenberg, W. Schwack, R. G. Berger, Enzyme Microb. Technol. 32 (2003) 623-628.
Y. Waché, A. Bosser-De Ratuld, J.-M. Belin: Production of Aroma Compounds by Enzymatic Cooxidation of Carotenoids. In: Carotenoid-Derived Aroma Compounds, P. Winterhalter, R. Rouseff (Eds.), ACS, Washington DC (2001) pp. 102-113.
A. Bosser, J.-M. Belin, Biotechnol. Progr. 10 (1994) 129-133.
F. Ropert, Ph.D. Thesis, Université de Bourgogne (1996).
M. Benboubetra, A. Baghiani, D. Atmani, R. Harrison, J. Dairy Sci. 87 (2004) 1580-1584.
P. Kuppusamy, J. L. Zweier, J. Biol. Chem. 264 (1989) 9880-9884.
A. Bosser, E. Paplorey, J.-M. Belin, Biotechnol. Progr. 11 (1995) 689-692.
Y. Waché, A. Bosser-De Ratuld, H. M. Ly, J.-M. Belin, J. Mol. Catal. B-Enzym. 19 (Special Issue) (2002) 197-201.
A. Ben Aziz, A. Grossman, M. Avron, Phytochemistry, 10 (1971) 1445-1452.
A. M. Klibanov, Trends Biotechnol. 15 (1997) 97-101.
M. Tuena de Gomez-Puyou, A. Gomez-Puyou, Crit. Rev. Biochem. Mol. Biol. 33 (1998) 53-89.
J. T. Chernys, J. A. D. Zeevaart, Plant Physiol. 124 (2000) 343-353.
C. Kiefer, S. Hessel, J. M. Lampert, K. Vogt, M. O. Lederer, D. E. Breithaupt, J. von Lintig, J. Biol. Chem. 276 (2001) 14110-14116.
C. Schmidt-Dannert, Curr. Opin. Biotechnol. 11 (2000) 255-261.
M. A. Nordermeer, W. Van Der Goot, A. J. Van Kooij, J. W. Veldsink, G. A. Veldink, J. F. G. Vliengenthart, J. Agric. Food Chem. 50 (2002) 4270-4274.
E. Blée, Trends Plant Sci. 7 (2002) 315-321.
J.-M. Belin, B. Dumont, F. Ropert, Method for the enzymatic preparation of aromas, particularly ionones and C6 to C10 aldehydes. WO Patent 9408028 (1994).
P. Brunerie, Y. Koziet, Process for producing natural cis-3-hexenol from unsaturated fatty acids. US Patent 5620879 (1997).
B. Rehbock, D. Gansser, R. G. Berger, Food Chem. 63 (1998) 161-165.
S. J. Garger, R. B. Holtz, M. J. McCulloch, H. F. Phillips, R. K. Teague, Method for providing green note compounds. WO patent 9526413 (2001).
I. L. Gatfield: Biotechnological Production of Natural Flavor Materials. In: Flavor Chemistry, Thirty Years of Progress, R. Teranishi, E. L. Wick, I. Hornstein (Eds.), Kluwer Academic, Plenum Publishers, New York (1999) pp. 211-227.
A.-M. Almosnino, J.-M. Belin, Biotechnol. Lett. 13 (1991) 893-898.
G. Bourel, J.-M. Nicaud, B. Nthangeni, P. Santiago-Gomez, J.-M. Belin, F. Husson, Enzyme Microb. Technol. 35 (2004) 293-299.
K. Matsui, T. Shibutani, T. Hase, T. Kajiwara, FEBS Lett. 394 (1996) 21-24.
K. Matsui, C. Miyahara, J. Wilkinson, B. Hiatt, V. Knauf, T. Kajiwara, Biosci. Biotechnol. Biochem. 64 (2000) 1189-1196.
K. Matsui, J. Wilkinson, B. Hiatt, V. Knauf, T. Kajiwara, Plant Cell Physiol. 40 (1999) 477-481.
N. Tijet, C. Schneider, B. L. Muller, A. R. Brash, Arch. Biochem. Biophys. 386 (2001) 281-299.
N. Tijet, U. Waspi, D. J. Gaskin, P. Hunziker, B. L. Muller, E. N. Vulfson, A. Slusarenko, A. R. Brash, I. M. Whitehead, Lipids, 35 (2000) 709-720.
I. Feusner, E. Berndt, Preparation of C9 aldehydes, alcohols and their esters, for use as aroma and flavoring agents, from unsaturated fatty acids, comprises modifying specific activities in e.g. plants. WO patent 0194606 (2001).
A. Häusler, N. Silke, K. Lerch, A. Muheim, Hydroperoxide lyases. US patent 6238898 (2001).
A. J. Slusarenko, I. M. Whitehead, D. J. H. Gaskin, N. Tijet, A. R. Brash, Guava (Psidium guajava) 13-hydroperoxide lyase and uses thereof. WO patent 9958648 (2001).
I. M. Whitehead, A.Brash, N. Tijet, Muskmelon (Cucumis melo) hydroperoxide lyase and uses thereof. WO patent 0173075 (2001).
S. Gleddie, D. Hegedus, U. Schafer, D. Brown, N. Bate, Hydrogen peroxide lyase regulatory region. WO patent 0250291 (2002).
Z. Huang, L. Dostal, J. P. Rosazza, J. Biol. Chem. 268 (1993) 23954-23958.
M. Gasson, M. J. C. Rhodes, A. Narbad, N. J. Walton, Production of vanillin. WO patent 9735997 (2001).
S. Okui, M. Uchiyama, M. Mizugaki, J. Biochem. 53 (1963) 265-270.
S. Okui, M. Uchiyama, M. Mizugaki, J. Biochem. 54 (1963) 536-540.
C. Ambid, S. Carle, G. De Billerbeck, Method for producing and extracting aromatic compounds. WO patent 9954432 (1999).
P. Cabella, P. Guarda, M. Barbeni, C. Fuganti, G. Allegrone, R. Cardillo, Process for the microbiological production of gamma- and delta-lactones. EP patent 0412880 (1991).
M. Farbood, G. Harris, L. E. Kizer, L. B. McLean, J. Morris, Process for preparing saturated lactones, products produced there-from and organoleptic uses of said products. EP patent 0952226 (1999).
M. Farbood, B. Willis, Optically active gamma-hydroxy decanoic acid preparation by cultivating microorganism to hydrolyse castor oil and subjecting to β-oxidation. US patent 4560656 (1985).
I. Gatfield, Gamma-decalactone preparation with high stereo-specificity. DE patent 4401388 (1995).
J. Meyer, Gamma-decalactone microbial production from alkyl ricinoleate - by hydrolysis, beta-oxidation, and chemical cyclisation of 4-hydroxydecanoic acid produced for flavoring and perfume. DE patent 4126997 (1993).
J.-M. Nicaud, J.-M. Belin, Y. Pagot, A. Endrizzi-Joran, Bioconversion of substrate with microbe auxotrophic for compound in medium deficient in this compound. FR patent 2734843 (1996).
G. V. Page, R. G. Eilerman, Process for the preparation of gamma and delta lactones. WO patent 8912104 (1989).
J. Rabenhorst, I. Gatfield, Process for the production of gamma-decalactone. WO patent 0024920 (2000).
H.-E. Spinnler, L. Dufossé, I. Souchon, A. Latrasse, C. Piffaut-Juffard, A. Voilley, P. Delest, Production of gamma-decalactone by bioconversion. FR patent 2705971 (1994).
J. Schrader, M. Etschmann, D. Sell, J.-M. Hilmer, J. Rabenhorst, Biotechnol. Lett. 26 (2004) 463-472.
G. Fantin, M. Fogagnolo, A. Guerrini, A. Medici, P. Pedrini, S. Fontana, Tetrahedron: Asymmetry, 12 (2001) 2709-2713.
H. E. Spinnler, C. Ginies, J. A. Khan, E. N. Vulfson, Proc. Natl. Acad. Sci. USA, 93 (1996) 3373-3376.
C. Blin-Perrin, D. Molle, L. Dufossé, J.-L. Le-Quéré, C. Viel, G. Mauvais, G. Féron, FEMS Microbiol. Lett. 188 (2000) 69-74.
A. Gurvitz, A. M. Mursula, A. I. Yagi, A. Hartig, H. Ruis, H. Rottensteiner, J. K. Hiltunen, J. Biol. Chem. 274 (1999) 24514-24521.
I. L. Gatfield, M. Güntert, H. Sommer, P. Werkhoff, Chem. Mikrobiol. Technol. Lebensm. 15 (1993) 165-170.
G. Iacazio, D. Martini, B. Faure, M. H. N'Guyen, FEMS Microbiol. Lett. 209 (2002) 55-60.
P. Fickers, P.-H. Benetti, Y. Waché, A. Marti, S. Mauersberger, M. Smit, J.-M. Nicaud, FEMS Yeast Res. (in press).
Y. Waché, M. Aguedo, J.-M. Nicaud, J.-M. Belin, Appl. Microbiol. Biotechnol. 61 (2003) 393-404.
E. H. Hettema, H. F. Tabak, Biochim. Biophys. Acta, 1486 (2000) 18-27.
Y. Waché, M. Aguedo, A. Choquet, I. Gatfield, J.-M. Nicaud, J.-M. Belin, Appl. Environ. Microbiol. 67 (2001) 5700-5704.
Y. Waché, M. Aguedo, M.-T. LeDall, J.-M. Nicaud, J.-M. Belin, J. Mol. Catal. B-Enzym. 19 (Special Issue)(2002) 347-351.
A. Groguenin, Y. Waché, E. Escamilla Garcia, M. Aguedo, F. Husson, M.-T. LeDall, J.-M. Nicaud, J.-M. Belin, J. Mol. Catal. B-Enzym. 28 (2004) 75-79.
M. Aguedo, Ph.D. Thesis, Université de Bourgogne (2002).
M. Aguedo, Y. Waché, F. Coste, F. Husson, J.-M. Belin, J. Mol. Catal. B-Enzym. 29 (2004) 31-36.
M. Aguedo, Y. Waché, V. Mazoyer, A. Sequeira-Le Grand, J.-M. Belin, J. Agric. Food Chem. 51 (2003) 3007-3011.
V. Ravaine, J. Bibette, N. Henry, J. Colloid Interface Sci. 255 (2002) 270-273.
Y. F. Dufrêne, C. J.-P. Boonaert, P. G. Rouxhet, Colloids Surf. B-Biointerfaces, 7 (1996) 113-128.
L. Dufossé, I. Souchon, G. Feron, A. Latrasse, H. E. Spinnler, Biotechnol. Progr. 15 (1999) 135-139.
M. Aguedo, L. Beney, Y. Waché, J.-M. Belin, J. Appl. Microbiol. 94 (2003) 1-8.
M. Aguedo, L. Beney, Y. Waché, J.-M. Belin, Int. J. Food Microbiol. 80 (2002) 211-215.
M. Aguedo, L. Beney, Y. Waché, J.-M. Belin, P. Gervais, Biotechnol. Lett. 24 (2002) 1975-1979.
G. Feron, Y. Waché: Microbial Biotechnology of Food Flavour Production. In: Food Biotechnology, 2nd ed., Marcel Dekker, New York (in press).
J. Schrader, M. M. W. Etschmann, D. Sell, J.-M. Hilmer, J. Rabenhorst, Biotechnol. Lett. 26 (2004) 463-472.
A. H. G. Cents, D. W. F. Brilman, G. F. Versteeg, Chem. Eng. Sci. 56 (2001) 1075-1083.
G. Feron, W. XiaoDong, C. Viel, C. Blin-Perrin, G. Mauvais, R. Cachon, C. Diviès: Influence of a Reducing Environment on the Bioconversion of Fatty Acids to Gamma-Decalactone with Sporidiobolus ruinenii: Cellular and Enzymatic Approaches. In: Flavour Research at the Dawn of the Twenty-First Century - 10th Weurman Flavour Research Symposium, J. L. Le Quere, P. X. Etievant (Eds.), Editions Tec & Doc, Paris (2002).
D. R. Nielsen, A. J. Daugulis, P. J. McLellan, Biotechnol. Bioeng. 83 (2003) 736-742.
E. Dumont, H. Delmas, Chem. Eng. Process. 42 (2003) 419-438.
K. C. Lowe, J. Fluor. Chem. 118 (2002) 19-26.
R. Leung, D. Poncelet, R. J. Neufeld, J. Chem. Technol. Biotechnol. 68 (1997) 37-46.
I. Belo, R. Pinheiro, M. Mota, Biotechnol. Progr. 19 (2003) 665-671.
R. Pinheiro, I. Belo, M. Mota, Appl. Microbiol. Biotechnol. 53 (2002) 842-847.
