Abstract
Thirty-three isolates belonging to six species of the genusTrichoderma were tested for the ability to hydroxylate progesterone to 11α-, 11β-, 11α,17α- and 6β,17α-derivatives, and epicortisol.T. aureoviride, T. harzianum, T. polysporum andT. pseudokoningii produced 11α-hydroxyprogesterone.T. harzianum andT. hamatum can form only the 11β-isomer.T. koningii andT. hamatum produced 11α-,11β-, 11α,17α- and 6β,11α-hydroxy derivatives. 11α, 11β, 6β,11α- and 11α,17α-hydroxyprogesterones and epicortisol are produced byT. aureoviride andT. pseudokoningii. Cortisol was produced only when the medium was fortified by 10 g/L peptone. This is the first record of conversion of progesterone to mono-, di- and trihydroxyprogesterones by theseTrichoderma species.
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References
Abdel-Galil M.S.: Biological transformations of progesterone by dematicaceous hyphomycetes.MSc Thesis. Botany Department, Faculty of Science, Assiut University, Assiut (Egypt) 1995.
Atta F.M., El-Kady I.A.: Transformation of progesterone byCochliobolus spicifer.Bull.Fac.Sci.Assiut Univ. 23, 83–91 (1994).
Brannon D.R., Mortin J., Oehlscloger A.C., Durham N.N., Zalkow L.H.: Chemical and microbial transformation of some steroids and terpenes.J.Org.Chem. 30, 760–762 (1965).
CIBA Ltd.: Polyoxygenated steroids.Brit.Pat. 816 922 (1959).
Colingsworth D.R., Brunner M.P., Haines W.J.: A partial microbiological synthesis of adrenal cortex hormones.J.Amer.Chem.Soc. 74, 2381–2382 (1952).
Colingsworth D.R., Karnemaate S.N., Hanson F.R., Brunner M.P., Mann K.M., Haines W.J.: A partial microbiological synthesis of hydrocortisone.J.Biol.Chem. 203, 807 (1953).
El-Kady I.A., Metwali M.R.: 17α-Hydroxylation ofCunninghamella echinulata on a laboratory fermentor scale.Pakistan J.Biochem. 16, 7–11 (1983).
El-Kady I.A., Metwali M.R.: 17α-Hydroxylation of progesterone byCunninghamella echinulata on a laboratory fermentor scale.Qatar Univ.Sci.Bull. 5, 145–152 (1985).
El-Refai H.A.: Microbial side-chain degradation of progesterone.MSc Thesis. Microbiology Department, Faculty of Pharmacy, Cairo 1995.
El-Refai H.A., Sallam L.A.R., El-Kady I.A.: Microbiological transformations of progesterone.J.Gen.Appl.Microbiol. 15, 301–307 (1969).
El-Refai H.A., Sallam L.A.R., El-Kady I.A.: Studies on the mechanism of progesterone transformation withRhizopus nigricans REF 129.J.Gen.Appl.Microbiol. 16, 137–144 (1970).
Eman Mostafa M.: Progesterone transformation as a diagnostic feature in the classification of theAspergillus niger group.Lett.Appl.Microbiol. 20, 243–246 (1995).
Eman Mostafa M., Zohri A.A.: Progesterone side-chain degradation by species ofAspergillus flavus group.Folia Microbiol. 45, 243–247 (2000).
Ghanem K.M.: Physiological studies on steroid-transforming microorganisms.PhD. Thesis. Faculty of Science, University of Alexandria, Alexandria (Egypt) 1982.
Hasegawa T., Takahashi K., Sakano I., Nishikawa M., Norita K., Noguchi S.: Oxidation of steroids.Jap.Pat. 424 (1959a).
Hasegawa T., Takahashi K., Itano I., Nishikawa M., Hagiwara H., Noguchi S.: Oxidation of steroids.Jap.Pat. 529 (1959b).
Hölker U., Dohse J., Höfer M.: Extracellular laccases in ascomycetesTrichoderma atroviride andTrichoderma harzianum.Folia Microbiol. 47, 423–428 (2002).
Ismail M.A., Zohri A.A.: Confirmation of the relationships ofAspergillus egyptiacus andEmericella nidulans using progesterone transformation.Lett.Appl.Microbiol. 18, 130–131 (1994).
Khallil A.M., Eman Mostafa M.: Microbiological transformation of progesterone by some zoosporic fungi.J.Basic Microbiol. 36, 255–259 (1996).
Kubicek C.P., Harman G.E.:Trichoderma and Gliocladium. 1. Basic Biology, Taxonomy and Genetics, p. 3. Taylor & Francis, London 1998.
Laskin A.I., Guiducci M.A., Fried J.: Synthesis of steroids withKabatiella phoradendri, US Pat. 2 977 286 (1961).
Lima L.H.C., de Marco J.L., Ulhoa C.J., Felix C.R.: Synthesis of aTrichoderma chitinase which affects theSclerotium rolfsii andRhizoctonia soloni cell walls.Folia Microbiol. 44, 45–49 (1999).
Mahato S.B., Garai S.: Advances in microbial steroid biotransformation.Steroids 62, 332–342 (1997).
McAleer W.J., Dulaney E.L.: Transformation of progesterone to 17α-hydroxyprogesterone byTrichoderma viride.Arch.Biochem.Biophys. 62, 111–112 (1956).
Meystre C., Vischer E., Wettstein A.: Mikrobiologische Hydroxylierung von Steroiden in der 17α- und 21-Stellung.Helv.Chim.Acta 37, 1548–1553 (1954).
Murray H.C., Peterson D.H.: Oxygenation of steroids byMucorales fungi.US Pat. 2 602 769 (1952).
Okada M., Yamada A., Ishidate M.: Microbiological transformation of dehydroepiandrosterone, progesterone, deoxycorticosterone and testosterone byGiberella saubinetti.Yakugaku Zasshi 85, 816–822 (1965).
Peterson D.H., Eppstein S.H., Meister P.D., Magerlein B.J., Murray H.C., Leigh H.M., Weintraub A., Reineke L.M.: The 11-epimer of compound F and other new oxygenated derivatives of compound S. A new route to cortisone.J.Am.Chem.Soc. 75, 412 (1953).
Prescott S.C., Dunn C.G.:Industrial Microbiology, 3rd ed., pp. 723–761. McGraw Hill, New York-Toronto-London & Kogakusha, Tokyo 1959.
Sallam L.A.R.: A contribution to the utilization of steroid sapogenins.PhD Thesis. Faculty of Science, Cairo University 1966.
Sallam L.A.R., El-Refai A.H., El-Kady I.A.: Thin-layer chromatography of some C-18, C-19 and C-21 steroids.J.Gen.Appl.Microbiol. 15, 309–315 (1969).
Samuels G.J.:Trichoderma: a review of biology and systematics of the genus.Mycol.Res. 100, 923–935 (1996).
Smith D., Onions A.H.:The Preservation and Maintenance of Living Fungi. CAB International Mycological Institute, London 1983.
Tsuda K., Asai T., Tizuka H., Tanaka T., Nakamura M., Okazaki H., Shirasaka M., Naito A.: Prednisolone,US Pat. 29 383 925 (1961).
Tůmova E., Šiblikova Z.O., Hanč O.: Biochemical oxidation of pregnene steroids. (In Czech)Českoslov.Farm. 4, 65 (1955).
Weisz E., Wix G., Bodanszky M.: Die Bildung von 11-Epicorticosterone auf mikrobiologischen Wege.Naturwissenschaften 43, 39 (1956).
Witkowska D., Maj A.: Production of lytic enzymes byTrichoderma spp. and their effect on the growth of phytopathogenic fungi.Folia Microbiol. 47, 279–282 (2002).
Wix G., Natonek M., Kovacs M.:Acta Microbiol.Acad.Sci.Hung. 6, 197 (1959);cited in Peterson D.H., p. 708 in C. Rainbow, A.H. Rose (Eds):Biochemistry of Industrial Microorganisms. Academic Press, London-New York 1963.
Zaffaroni A., Rubin B.A.: 21-Hydroxylation of cyclopentanophenanthrene derivatives byAspergillus niger. US Pat. 2 812 285 (1957).
Zaffaroni A., Campillo C.C., Cordova F., Rosenkranz G.: Steroids — LXVI Microbiological hydroxylation of steroids in position 21.Experientia 11, 219 (1955).
Zohri A.A.: Progesterone transformation as a biochemical aid in classification of the genusEmericella.Folia Microbiol. 45, 391–396 (2000).
Zohri A.A., Abdel-Galil M.S.M.: Progesterone transformations by three species ofHumicola.Folia Microbiol. 44, 277–282 (1999).
Zohri A.A., Eman Mostafa M.: Biotransformation of steroids by some thermophilic and thermotolerant fungi grown on yeast-starch and molasses media.Bull.Fac.Sci.Assiut Univ. 29 (2-D), 425–431 (2000).
Zohri A.A., Hashem M.: Toxicological, morphological, physiological features and genomic DNA as taxonomic criteria ofTrichoderma species in Egypt.Bull.Fac.Sci.Assint Univ. 32 (1-D), 183–210 (2003).
Zohri A.A., Ismail M.A.: Based on biochemical and physiological behavior, where isAspergillus egyptiacus better placed?Folia Microbiol. 39, 415–419 (1994).
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El-Kadi, I.A., Eman Mostafa, M. Hydroxylation of progesterone by someTrichoderma species. Folia Microbiol 49, 285–290 (2004). https://doi.org/10.1007/BF02931044
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DOI: https://doi.org/10.1007/BF02931044