Abstract
The use of microorganisms to induce chemical modifications in organic molecules is a very useful tool in organic synthesis, to obtain biologically active substances. The fungus Cephalosporium aphidicola is known by its ability to hydroxylate several skeleton positions of many classes of organic compounds. In this work, the microbial transformation of ent-kaur-16-en-19-ol (1) by C. aphidicola, afforded two hydroxylated compounds, ent-kauran-16b,19-diol (2) and ent-kauran-16b,17,19-triol (3). Their structures were established by 1D and 2D-NMR studies. Both compounds were tested for their action on the growth of radical and shoot of Lactuca sativa.References
J. R. Hanson, An Introduction to Biotransformations in Organic Chemistry, W. H. Freeman/Spectrum and Co. Ltd, New York, 1995.
J. R. Hanson, P. B. Hitchcock J. A. Takahashi, Phytochemistry 40 (1995) 797.
H. S. Vieira, J. A. Takahashi, M. A. D. Boaventura, J. Agric Food Chem. 50 (2002) 3704.
J. A. Takahashi, H. S. Vieira, J. R. Hanson, P. B. Hitchcock, A. B. Oliveira, M. A. D. Boaventura, Quim. Nova 24 (2001) 616.
H. S. Vieira, J. A. Takahashi, M. A. D. Boaventura, Fitoterapia 72 (2001) 854.
G. G. Harrigan, V. S. Bolzani, L. A. A. Gunatilaka, D. G. I. Kingston, Phytochemistry 36 (1994) 109.
A. Morales, P. Pérez, R. Mendoza, R. Compagnone, A. Suarez, F. Arvelo, J. L. Ramírez, I. Galindo-Castro, Cancer Lett. 218 (2005) 109.
Y. Wu, Y. Hung, F. R. Chang, M. Cosentino, H. K. Wang, K.- H. Lee, J. Nat. Products 59 (1996) 635.
H. S. Vieira, J. A. Takahashi, A. B. Oliveira, E. Chiari, M. A. D. Boaventura J. Braz. Chem. Soc. 13 (2002) 151.
R. Batista, J. L. Humberto, E. Chiari, A. B. Oliveira, Bioorg. Med. Chem. 15 (2007) 381.
A. Urzúa, M. C. Rezende, C. Mascayano, L. Vásquez, Molecules 13 (2008) 882.
H. S. Vieira, J. A. Takahashi, L. P. S. Pimenta, M. A. D. Boaventura, Z. Naturforsch. C 60 (2005) 72.
M. A. D. Boaventura, R. G. Pereira, L. B. O. Freitas, L. A. Reis, H. S. Vieira, J. Agric. Food Chem. 56 (2008) 2985.
B. M. Fraga, P. González, M. G. Hernández, S. Suárez, Tetrahedron 61 (2006) 5623.
H. S. Vieira, J. A. Takahashi, M A. D. Boaventura, Appl. Microbiol. Biotechnol. 53 (2000) 601.
B. M. Fraga, P. González, M. G. Hernández, S. Suárez, Tetrahedron, 61 (2006) 5623.
M. A. D. Boaventura, A. B. Oliveira, J. R. Hanson, P. B. Hitchcock, J. A Takahashi, Phytochemistry 40 (1995) 1667.
I. Kiran, T. Akar, A. Gorgulu, C. Kazaz, Biotechnol. Lett. 27 (2005) 1007.
M. A. D. Boaventura, J. R. Hanson, P. B. Hitchcock, J. A. Takahashi, Phytochemistry 37 (1994) 387.
J. R. Hanson, A. Truneh, Phytochemistry 47 (1998) 423.
M. L. G. Oliveira, L. P. Duarte, G. D. F. Silva, S. A. Vieira Filho, V. F. Knupp, F. G. P. Alves, Magn. Reson. Chem. 45 (2007) 895.
M. S. Correa, G. M. S. P. Guilhon, L. M. Conserva, Fitoterapia 69 (1998) 277.
A. Rumbero, F. J. Arriaga-Giner, E. Wollenweber, Z. Naturforsch. C 55 (2000) 318.
T. Satake, R. Murakami, Y. Saiki, C.-M. Chen, Chem. Pharm. Bull. 31 (1983) 3865.
A.-L. Pérez-Castorena, M. Martínez-Vázquez A. R. de Vivar, Phytochemistry 46 (1997) 729.

This work is licensed under a Creative Commons Attribution 4.0 International License.
Copyright (c) 2018 Eclética Química Journal