Navegar

Colección

Datos Estadísticas

Artículo

Quintana, P.G.; Romero, S.M.; Vaamonde, G.; Baldessari, A. "New metabolites of drospirenone obtained in Mucorales fungi culture" (2013) Journal of Molecular Catalysis B: Enzymatic. 97:110-117
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Microbial transformation of 6,7,15,16-dimethylene-3-oxo-17-pregn-4-ene-2, 17-carbo-lactone, the well-known contraceptive drospirenone (1), using fungal cells was carried out. Six fungal strains of different species of Order Mucorales were evaluated in this study, namely Absidia corymbifera BAFC 1072, Absidia corymbifera BAFC 1080, A. coerulea, Mucor plumbeus BAFC 2314, Rhizopus oryzae and Syncephalastrum racemosum. Four products were obtained by hydroxylation at C-11 and C-2 and epimerization at C-17 of drospirenone by A. corymbifera BAFC 1072, A. coerulea and S. racemosum. The structures were elucidated as 6β,7β,15β,16β-dimethylene-11α-hydroxy-3- oxo-l7α-pregn-4-en-21,17-carbolactone (2), 6β,7β,15β, 16β-dimethylene-11α-hydroxy-3-oxo-l7β-pregn-4-en-21, 17-carbolactone (3), 6β,7β,15β,16β-dimethylene-11β- hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (4) and 6β,7β,15β,16β-dimethylene-2β-hydroxy-3-oxo-l7α- pregn-4-en-21,17-carbolactone (5), on the basis of extensive spectral data including 2D NMR spectroscopy and MS. Products 3, 4 and 5 were found to be new compounds. Several biotransformation parameters such as the employment of growing or resting cells, inoculum size, agitation speed, drospirenone concentration, temperature, pH and presence of co-solvent were seen to be important to the optimization of the process. © 2013 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:New metabolites of drospirenone obtained in Mucorales fungi culture
Autor:Quintana, P.G.; Romero, S.M.; Vaamonde, G.; Baldessari, A.
Filiación:Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Universidad de Buenos Aires, Pabellón 2, piso 3, C1428EGA, Buenos Aires, Argentina
Laboratorio de Microbiología de Alimentos, Departamento de Química Orgánica y PROPLAME-PRHIDEB, Universidad de Buenos Aires, Pabellón 2, piso 3, C1428EGA, Buenos Aires, Argentina
Palabras clave:Biotransformation; Drospirenone; Epimerization; Hydroxylation; Mucorales; 2D-NMR spectroscopy; Agitation speed; Biotransformation; Drospirenone; Epimerization; Microbial transformation; Mucorales; Rhizopus oryzae; Nuclear magnetic resonance spectroscopy; Hydroxylation; 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone; 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17beta pregn 4 en 21,17 carbolactone; 6beta,7beta,15beta,16beta dimethylene 11beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone; 6beta,7beta,15beta,16beta dimethylene 2beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone; drospirenone; lactone derivative; solvent; unclassified drug; Absidia; absidia coerulea; agitation; animal cell; article; Candida; Candida aphidicola; cell growth; chemical structure; controlled study; drug determination; drug hydroxylation; drug metabolism; drug transformation; epimerization; fungal cell; fungal strain; fungus; fungus culture; inoculation; metabolite; Mucor; mucor plumbeus; Mucorales; nonhuman; nuclear magnetic resonance spectroscopy; pH; pharmacological parameters; process optimization; Rhizopus oryzae; stereochemistry; syncephalastrum racemosum; temperature; Zygomycetes; Absidia corymbifera; Fungi; Mucor plumbeus; Mucorales; Rhizopus oryzae; Syncephalastrum racemosum
Año:2013
Volumen:97
Página de inicio:110
Página de fin:117
DOI: http://dx.doi.org/10.1016/j.molcatb.2013.08.005
Título revista:Journal of Molecular Catalysis B: Enzymatic
Título revista abreviado:J. Mol. Catal. B Enzym.
ISSN:13811177
CODEN:JMCEF
CAS:drospirenone, 67392-87-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v97_n_p110_Quintana

Referencias:

  • Elger, W., Beier, S., Pollow, K., Garfield, R., Shi, S.Q., Hillisch, A., (2003) Steroids, 68, pp. 891-905
  • Sitruk-Ware, R., (2008) Maturitas, 61, pp. 151-157
  • Bitzer, J., Simon, J.A., (2011) Contraception, 84, pp. 342-356
  • Schindler, A.E., (2013) International Journal of Endocrinology and Metabolism, 11, pp. 41-47
  • Kim, G.K., Del Rosso, J.Q., (2012) Journal of Clinical and Aesthetic Dermatology, 5, pp. 37-50
  • Batukan, C., Muderris, I.I., (2006) Fertility and Sterility, 85, pp. 436-440
  • De Berardis, D., Serrroni, N., Salerno, R.M., Ferro, F.M., (2007) Therapeutics and Clinical Risk Management, 3, pp. 585-590
  • Oelkers, W., (2004) Molecular and Cellular Endocrinology, 217, pp. 255-261
  • Plu-Bureau, G., Maitrot-Mantelet, L., Hugon-Rodin, J., Canonico, M., (2013) Best Practice & Research Clinical Endocrinology & Metabolism, 27, pp. 25-34
  • Morfin, R., Courchay, G., (1994) Journal of Steroid Biochemistry and Molecular Biology, 50, pp. 91-100
  • Simeo, Y., Sinisterra, J.V., (2009) Mini-Reviews in Organic Chemistry, 6, pp. 128-134
  • D'Antona, N., Nicolosi, G., Morrone, R., Kub, D., David Kubâc, O., Kaplan, L., Martinkova, (2010) Tetrahedron: Asymmetry, 21, pp. 695-702
  • Zafar, S., Bibi, M., Yousuf, S., Choudhary, M.I., (2013) Steroids, 78, pp. 418-425
  • Mangone, C.P., Pereyra, E.N., Argimón, S., Moreno, S., Baldessari, A., (2002) Enzyme and Microbial Technology, 30, pp. 596-601
  • Rustoy, E.M., Pereyra, E.N., Moreno, S., Baldessari, A., (2004) Tetrahedron: Asymmetry, 15, pp. 3763-3768
  • Donova, M.D., Ergorova, O.V., (2012) Applied Microbiology and Biotechnology, 94, pp. 1423-1447
  • Peart, P.C., Chen, A.R.M., Reynolds, W.F., Reese, P.B., (2012) Steroids, 77, pp. 85-90
  • Kun, C., Wang-Yu, T., Dong-Zhi, W., Wei, J., (2007) Enzyme and Microbial Technology, 41, pp. 71-79
  • Koshimura, M., Utsukiharab, T., Haraa, A., Mizobuchia, S., Horiuchic, C.A., Kuniyoshia, M., (2010) Journal of Molecular Catalysis B: Enzymatic, 67, pp. 72-77
  • Somal, P., Chopra, C.L., (1985) Applied Microbiology and Biotechnology, 21, pp. 267-269
  • Fernandes, P., Cruz, A., Angelova, B., Pinheiro, H.M., Cabral, J.M.S., (2003) Enzyme and Microbial Technology, 32, pp. 688-705
  • Murray, H.C., Peterson, D.H., U.S. Patent 2 602 769 (1952) Upjohn Co., Kalamazoo. Michigan, USA; Manosroi, J., Saowahkon, S., Manosroi, A., (2007) Enzyme and Microbial Technology, 41, pp. 322-325
  • Bava, A., Nasini, G., Fronza, G., (2012) Journal of Molecular Catalysis B: Enzymatic, 82, pp. 59-63
  • Rustoy, E.M., Cerrutti, P., Galvagno, M.A., Baldessari, A., (2008) Biocatalysis and Biotransformation, 26, pp. 204-209
  • Monsalve, L.N., Cerrutti, P., Galvagno, M.A., Baldessari, A., (2010) Biocatalysis and Biotransformation, 28, pp. 137-143
  • Baldessari, A., Maier, M.S., Gros, E.G., (1995) Tetrahedron Letters, 36, pp. 4349-4352
  • Baldessari, A., Bruttomesso, A.C., Gros, E.G., (1996) Helvetica Chimica Acta, 79, pp. 999-1004
  • Bruttomesso, A.C., Baldessari, A., (2004) J. Mol. Catalysis, B: Enzym, 13, pp. 149-153
  • Bruttomesso, A.C., Tiscornia, A., Baldessari, A., (2004) Biocatalysis and Biotransformation, 22, pp. 147-152
  • Rustoy, E.M., Ruiz Arias, I.E., Baldessari, A., (2005) Arkivoc, XII, pp. 175-180
  • Quintana, P.G., Baldessari, A., (2009) Steroids, 74, pp. 1007-1014
  • Monsalve, L.N., Machado Rada, M.Y., Ghini, A.A., Baldessari, A., (2008) Tetrahedron, 64, pp. 1721-1730
  • Quintana, P., Guillén, M., Marciello, M., Valero, F., Palomo, J.M., Baldessari, A., (2012) European Journal of Organic Chemistry, pp. 4306-4312
  • Nickisch, K., Bittler, D., Casals-Stenzel, J., Laurent, H., Nickolson, R., Nishino, Y., Petzoldt, K., Wiechert, R., (1985) Journal of Medicinal Chemistry, 28, pp. 546-550
  • Holland, H.L., (1999) Steroids, 64, pp. 178-186
  • You, L., (2004) Chemico-Biological Interactions, 147, pp. 233-246
  • Backes, W.L., Kelley, R.W., (2003) Pharmacology & Therapeutics, 98, pp. 221-233
  • Bernhardt, R., (2006) Journal of Biotechnology, 124, pp. 128-145
  • Swizdor, A., Kolek, T., Panek, A., Milecka, N., (2012) Current Organic Chemistry, 16, pp. 2551-2582
  • Zafar, S., Bibi, M., Yousuf, S., Choudary, M.I., (2013) Steroids, pp. 418-425
  • Preisig, C.L., Laakso, J.A., Mocek, U.M., Wang, P.T., Baez, J., Byng, G., (2003) Journal of Natural Products, 66, pp. 350-356
  • Bortolino, O., Medici, A., Poli, S., (1997) Steroids, 62, pp. 564-577
  • Ye, M., Han, J., An, D., Tu, G., Guo, D., (2005) Tetrahedron, 61, pp. 8947-8955
  • Dumasia, M.C., (2003) Rapid Communications in Mass Spectrometry, 17, pp. 320-329
  • Bensasson, C.S., Hanson, J.R., Huerou, Y.L., (1999) Phytochemistry, 52, pp. 883-898
  • Yan, J.L., Lee, S.S., Wang, K.C., (2000) Steroids, 65, pp. 863-870
  • Žnidaršič, P., Komel, R., Pavko, A., (1998) Journal of Biotechnology, 60, pp. 207-216
  • Pitt, J.I., Hocking, A., (1997) Fungi and Food Spoilage, , third ed. Blackie Academic & Professional Cambridge

Citas:

---------- APA ----------
Quintana, P.G., Romero, S.M., Vaamonde, G. & Baldessari, A. (2013) . New metabolites of drospirenone obtained in Mucorales fungi culture. Journal of Molecular Catalysis B: Enzymatic, 97, 110-117.
http://dx.doi.org/10.1016/j.molcatb.2013.08.005
---------- CHICAGO ----------
Quintana, P.G., Romero, S.M., Vaamonde, G., Baldessari, A. "New metabolites of drospirenone obtained in Mucorales fungi culture" . Journal of Molecular Catalysis B: Enzymatic 97 (2013) : 110-117.
http://dx.doi.org/10.1016/j.molcatb.2013.08.005
---------- MLA ----------
Quintana, P.G., Romero, S.M., Vaamonde, G., Baldessari, A. "New metabolites of drospirenone obtained in Mucorales fungi culture" . Journal of Molecular Catalysis B: Enzymatic, vol. 97, 2013, pp. 110-117.
http://dx.doi.org/10.1016/j.molcatb.2013.08.005
---------- VANCOUVER ----------
Quintana, P.G., Romero, S.M., Vaamonde, G., Baldessari, A. New metabolites of drospirenone obtained in Mucorales fungi culture. J. Mol. Catal. B Enzym. 2013;97:110-117.
http://dx.doi.org/10.1016/j.molcatb.2013.08.005