Five 14α-hydroxylated derivatives of androstane and pregnane steroids were obtained using mycelium of the mold fungus Curvularia lunata (VKPM F-981). The conditions for microbiological transformation of androst-4-en-3,17-dione that enabled its 14α-hydroxy analog to be obtained in yields up to 60% with substrate loading 6 g/L were determined. The 21-acetoxy analog of proligestone was synthesized from 14α-hydroxycortexolone that was formed simultaneously with hydrocortisone during hydroxylation of cortexolone by C. lunata. The resulting 14α- and 14α,21-hydroxysteroids could be used as precursors for the synthesis of new drugs.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
S. B. Mahato, S. Garai, Steroids, 62, 332–345 (1997).
A. Shafiq, K. Henderson, G. Dumsday,M. Zachariou, Australas. Biotechnol., 11(2), 26–28 (2001).
V. Parez, D. Sulton, J. Reprod. Fertil., Suppl., 47, 544–545 (1993).
M. Kutzler, A. Wood, Theriogenology, 66, 514–525 (2006).
M. Yoshihama, K. Tamura, N. Miata, et al., “Novel androst-4-ene-3-dione derivatives and process for their preparation,” Eur. Pat. Appl. 88901462, Publ. No. 0300062, Feb. 5, 1988.
P. M. Smid, W. J. Van Zoest, P. G. Weber, A. F. Marx, “14α,17α-Dihydroxy-17-substituted steriods,” U. S. Pat. No. 5,093,502, Mar. 3, 1992.
S. Hu, G. Genain, R. Azerad, Steroids, 60, 337–352 (1995).
W. Charney, H. H. Herzog, Microbial Transformation of Steroids, Academic Press, New York, London (1967).
O. Schaaf, K. Dettner, J. Steroid Biochem. Mol. Biol., 67, 451–465 (1998).
A. Capek, O. Hanc, M. Tadra, Microbial Transformation of Steroids, Akademia Publishing House of the Czechoslovak Acad. Sci., Prague (1966).
A. A. Akhrem, Yu. A. Titov, Steroids and Microorganisms [in Russian], Nauka, Moscow (1970).
L. L. Smith, Terpenoids and Steroids, Vol. 4, K. H. Overton, Academic Press, New York (1975), pp. 394–530.
V. V. Kollerov, A. A. Shutov, V. V. Fokina, et al., J. Mol. Catal. B: Enzym., 55, 61–68 (2008).
V. V. Kollerov, A. A. Shutov, V. V. Fokina, et al., Prikl. Biokhim. Mikrobiol., 46(2), 212–220 (2010).
V. A. Andryushina, A. V. Druzhinina, V. V. Yaderets, et al., Prikl. Biokhim. Mikrobiol., 47, No. 1, 50–57 (2011).
V. A. Andryushina, N. V. Rodina, T. S. Stytsenko, et al., Prikl. Biokhim. Mikrobiol., 47(1), 297–301 (2011).
V. A. Andrjushina, T. S. Savinova, K. G. Skrjabin, “Method of preparing corticosteroids,” RU Pat. No. 2,156,256, Sept. 20, 2000; Byull. Izobret., No. 26 (2000).
G. S. Grinenko, V. A. Andryushina, V. V. Korkhov, et al., “Contraceptive method and remedy for animals,” RU Pat. No. 2,048,149, Nov. 20, 1995; Byull. Izobret., No. 32 (1995).
S. B. Chincholkar, R. S. Laxman, R. D. Wakharkar, World J. Microbiol. Biotechnol., 11, 357–358 (1995).
H. L. Holland, S. Poddar, B. Tripet, J. Ind. Microbiol., 10, 195–197 (1992).
S. B. Mahato, S. Banerjee, S. Podder, Phytochemistry, 28, 7–40 (1989).
M. L. Choudhary, S. Sultan, M. T. H. Khan, et al., Nat. Prod. Res., 18(6), 519–535 (2004).
V. V. Yaderets, V. A. Andryushina, N. E. Voishvillo, et al., Khim.-farm. Zh., 43(1), 37–40 (2009).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 47, No. 2, pp. 35 – 40, February, 2013.
Rights and permissions
About this article
Cite this article
Andryushina, V.A., Voishvillo, N.E., Druzhinina, A.V. et al. 14α-Hydroxylation of steroids by mycelium of the mold fungus Curvularia lunata (VKPM F-981) to produce precursors for synthesizing new steroidal drugs. Pharm Chem J 47, 103–108 (2013). https://doi.org/10.1007/s11094-013-0905-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-013-0905-6