Artículos de revistas
Odor-active Alcohols From The Fungal Transformation Of α-farnesene
Registro en:
Journal Of Agricultural And Food Chemistry. , v. 54, n. 24, p. 9079 - 9084, 2006.
218561
10.1021/jf062089j
2-s2.0-33845673350
Autor
Krings U.
Hardebusch B.
Albert D.
Berger R.G.
Marostica Jr. M.
Pastore G.M.
Institución
Resumen
Submerged microbial cultures were screened for their potential to oxifunctionalize α-farnesene. The major oxidation product in all transforming cultures, 3,7,11-trimethyldodeca-1,3(E),5(E)10-tetraen-7-ol, showed a pleasant citrus-like odor and peak concentrations of 170 mg L -1. An Aspergillus niger isolate from mango generated another two terpene alcohols identified as diastereomeric menth-1-en-3-[2-methyl-1,3-butadienyl]-8-ol, a new natural compound with an apricot-like odor. The regiospecifity of the oxygen attack with concurrent lack of stereoselectivity suggested that the initial step of the bioconversion resembled the chemical autoxidation starting with the generation of an intermediate resonance-stabilized carbon-centered radical or carbocation. © 2006 American Chemical Society. 54 24 9079 9084 Breitmaier, E., (2005) Terpene Aromen, Düfte, Pharmaka, Pheromone, , Wiley-VCH: Weinheim, Germany Schrader, J., Berger, R.G., Biotechnological production of terpenoid flavor and fragrance compounds (2001) Biotechnology, 10, pp. 374-422. , Rehm, H. J., Ed. Wiley-VCH: Weinheim, Germany, Special Processes Demyttenaere, J.C.R., Biotransformation of terpenoids by microorganisms (2001) Studies in Natural Product Chemistry, 25 (PART F), pp. 125-178. , Attaur-Rahman, H. E. J., Ed. Elsevier Science Ltd.: New York Kaspera, R., Krings, U., Nanzad, T., Berger, R.G., Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum (2005) Appl. Microbiol. Biotechnol., 67, pp. 477-483 Abraham, W.-R., Arfmann, H.-A., Giersch, W., Microbial hydroxylation of precursors of sinensal (1992) Z. Naturforsch., 47 C, pp. 851-858 Ohloff, G., (1994) Scent and Fragrances, , Springer-Verlag: Berlin Rowan, D.D., Hunt, M.B., Fielder, S., Norris, J., Sherburn, M.S., Conjugated triene oxidation products of α-farnesene induce symptoms of superficial scald on stored apples (2001) J. Agric. Food Chem., 49, pp. 2780-2787 Whitaker, B.D., Saftner, R.A., Temperature-dependant autoxidation of conjugated trienols from apple peel yields 6-methyl-5-hepten-2-one, a volatile implicated in induction of scald (2000) J. Agric. Food Chem., 48, pp. 2040-2043 Fielder, S., Rowan, D.D., Sherburn, M.S., Synthesis of sesquiterpene polyene hydroperoxides by regio- and stereoselective transposition reactions (1998) Tetrahedron, 54, pp. 12907-12922 Henry, T., Iwen, P.C., Hinrichs, S.H., Identification of Aspergillus species using internal transcribed spacer regions 1 and 2 (2000) J. Clin. Microbiol., 38, pp. 1510-1515 Onken, J., Berger, R.G., Effects of R-(+)-limonene on submerged cultures of the terpene transforming basidiomycete Pleurotus sapidus (1999) J. Biotechnol., 69, pp. 163-168 Brimble, M.A., Rowan, D.D., Spicer, J.A., Synthesis of conjugated trienes and related oxidation products of α-farnesene (1994) Aust. J. Chem., 47, pp. 1979-1988 Fielder, S., Rowan, D.D., Sherburn, M.S., Synthesis of α-farnesene hydroperoxides (1996) Synlett, pp. 349-350 Rowan, D.D., Allen, J.M., Fielder, S., Spicer, J.A., Brimble, M.A., Identification of conjugated triene oxidation products of α-farnesene in apple skin (1995) J. Agric. Food Chem., 43, pp. 2040-2045 Spicer, J.A., Brimble, M.A., Rowan, D.D., Oxidation of α-farnesene (1993) Aust. J. Chem., 46, pp. 1929-1939 Whitaker, B.D., Solomos, T., Harrison, D.J., Quantification of α-farnesene and its conjugated trienol oxidation products from apple peel by C 18-HPLC with UV detection (1997) J. Agric. Food Chem., 45, pp. 760-765 Grosch, W., Detection of potent odorants in foods by aroma extract dilution analysis (1993) Trends Food Sci. Technol., 4, pp. 513-518 Anet, E.F.L.J., Autoxidation of α-farnesene (1969) Aust. J. Chem., 22, pp. 2403-2410 Cavill, G.W.K., Coggiola, I.M., Photosensitized oxygenation of α-farnesene (1971) Aust. J. Chem., 24, pp. 135-142 Rueda, A., Zubía, E., Ortega, M.J., Salvá, J., New acyclic sesquiterpenes from the Caribbean gorgonian Plexaurella grisea (2001) J. Nat. Prod., 64, pp. 401-405 Bohlmann, F., Grenz, M., Über neue Inhaltsstoffe aus Vertretern der Eupatorium-Gruppe (1977) Chem. Ber., 110, pp. 1321-1329 Weyerstahl, P., Christiansen, C., Marshall, H., Isolation and synthesis of isohumbertiol, the first naturally occurring sesquiterpene alcohol with a humbertian skeleton (1992) Liebigs Ann. Chem., pp. 1325-1328 Kaspera, R., Krings, U., Pescheck, M., Sell, D., Schrader, J., Berger, R.G., Regio- and stereoselective fungal oxyfunctionalisation of limonenes (2005) Z. Naturforsch., 60 C, pp. 45-466 Kapich, A.N., Steffen, K.T., Hofrichter, M., Hatakka, A., Involvement of lipid peroxidation of a non-phenolic lignin model compound by manganese peroxidase of the litter-decomposing fungus Stropharia coronilla (2005) Biochem. Biophys. Res. Commun., 330, pp. 371-377