Investigation of the importance of the C-2 and C-13 oxygen functions in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145

Phytochemistry

Volumn 65, Issue 15, 2004, Pages 2211-2217

  Martin, Glenroy D A ^a   Reynolds, William F ^b   Reese, Paul B ^a  

^a UNIVERSITY OF THE WEST INDIES   (Jamaica)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Biotransformation; Diterpene; Hydroxylation; Rhizopus arrhizus; Rhizopus oryzae ATCC 11145; Scrophulariaceae; Stemodane; Stemodia maritima

Indexed keywords

13 HYDROXYSTEMODAN 2 ONE; 2ALPHA,13 DIHYDROXYSTEMODANE; 2ALPHA,7BETA,13 TRIHYDROXYSTEMODANE; 2BETA,13 DIHYDROXYSTEMODANE; 2BETA,7,13 TRIHYDROXYSTEMODANE; 6ALPHA,13 DIHYDROXYSTEMODAN 2 ONE; 7BETA,13 DIHYDROXYSTEMODAN 2 ONE; OXYGEN; STEMODIN; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; HYDROXYLATION; RHIZOPUS ORYZAE;

BIOTRANSFORMATION; CATALYSIS; DITERPENES; HYDROXYLATION; MOLECULAR STRUCTURE; OXYGEN; RHIZOPUS; STEREOISOMERISM;

RHIZOPUS; RHIZOPUS ORYZAE; SCROPHULARIACEAE; STEMODIA; STEMODIA MARITIMA;

EID: 4344714020     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2004.05.016     Document Type: Article

References (27)

1. Abalain C., Buisson D., Azerad R. Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones. Tetrahedron: Asymmetry. 7:1996;2983-2996
2. Arséniyadis S., Ouazzani J., Rodriguez R., Rumbero A., Ourisson G. Biohydroxylations of hydrindenone derivatives. Tetrahedron Lett. 32:1991;3573-3576
3. Auret B.J., Boyd D.R., Henbest H.B., Watson C.G. Species-strain dependence of stereoselectivity in microbial oxidation of thioethers. Phytochemistry. 13:1974;65-68
4. Badria F.A., Hufford C.D. Microbial transformations of stemodin, a Stemodia diterpene. Phytochemistry. 30:1991;2265-2268
5. Buchanan G.O., Reese P.B. Biotransformation of diterpene and diterpene derivatives by Beauveria bassiana ATCC 7159. Phytochemistry. 56:2001;141-151
6. Cabon O., Larchevêque M., Buisson D., Azerad R. Microbial reduction of 2-chloro-3-aryl-3-oxopropionic acid esters. Tetrahedron Lett. 33:1992;7337-7340
7. Chen A.R.M., Reese P.B. Biotransformation of terpenes from Stemodia maritima by Aspergillus niger ATCC 9142. Phytochemistry. 59:2002;57-62
8. De Oliveira B.H., Dos Santos M.C., Leal P.C. Biotransformation of the diterpenoid, isosteviol, by Aspergillus niger, Penicillium chrysogenum and Rhizopus arrhizus. Phytochemistry. 51:1999;737-741
9. El Sayed K.A., Hamann M.T., Waddling C.A., Jensen C., Lee S.K., Dunstan C.A., Pezzuto J.M. Structurally novel bioconversion products of the marine natural product sarcophine effectively inhibit JB6 cell transformation. J. Org. Chem. 63:1998;7449-7455
10. Feiters M.C., Rowan A.E., Nolte R.J.M. From simple to supramolecular cytochrome P450 mimics. Chem. Rev. Soc. 29:2000;375-384
11. Hanson J.R., Reese P.B., Takahashi J.A., Wilson M.R. Biotransformation of some stemodane diterpenoids by Cephalosporium aphidicola. Phytochemistry. 36:1994;1391-1393
12. Holland H.L. The mechanism of the microbial hydroxylation of steroids. Chem. Soc. Rev. 11:1982;371-395
13. 4 -3-ketosteroids by the fungus Rhizopus arrhizus Acc. Chem. Res. 17:1984;398-402
14. 1. Can. J. Chem. 68:1990;282-293
15. Holland H.L., Brown F.M., Rao J.A., Chenchaiah P.C. Synthetic approaches to the prostaglandins using microbial biotransformation. Dev. Ind. Microbiol. 29:1988;191-195
16. Holland H.L., Lakshmaiah G., Ruddock P.L. Microbial hydroxylation of acetylaminosteroids. Steroids. 63:1998;484-495
17. Huang-Minlon Reduction of steroid ketones and other carbonyl compounds by modified Wolff Kishner method. J. Am. Chem. Soc. 71:1949;3301-3303
18. Hufford C.D., Badria F.A., Abou-Karam M., Shier W.T., Rogers R.D. Preparation, characterization, and antiviral activity of microbial metabolites of stemodin. J. Nat. Prod. 54:1991;1543-1552
19. Hufford C.D., Capiton G.A., Clark A.M., Baker J.K. Metabolism of impramine by microorganisms. J. Pharm. Sci. 70:1981;151-155
20. Hufford C.D., Oguntimein B.O., Muhammad I. New stemodane diterpenes from Stemodia maritima. J. Nat. Prod. 55:1992;48-52
21. Lupi A., Patamia M., Grgurina I., Bettolo R.M., Leo O.D., Gioia P., Antonaroli S. Biogenetic-type total synthesis of (±)-2-deoxystemodinone. Helv. Chim. Acta. 67:1984;2261-2263
22. Manchand P.S., White J.D., Wright H., Clardy J. Structures of stemodin and stemodinone. J. Am. Chem. Soc. 93:1973;2705-2706
23. Martin G.D.A., Reynolds W.F., Reese P.B. Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145. Phytochemistry. 65:2004;701-710
24. Moore-Landecker E. Fundamentals of the Fungi. 1982;Prentice-Hall, Englewood Cliffs, NJ. p. 84
25. Orabi K.Y., Li E., Clark A.M., Hufford C.D. Microbial transformation of sampangine. J. Nat. Prod. 62:1999;988-992
26. Ouazzani J., Arséniyadis S., Alvarez-Manzaneda R., Rumbero A., Ourisson G. Microbial hydroxylations of further octalin derivatives. Tetrahedron Lett. 32:1991;1983-1986
27. Peterson D.H., Murray H.C., Eppstein S.H., Reineke L.M., Weintraub A., Meister P.D., Leigh H.M. Microbiological transformation of steroids. I. Introduction of oxygen at carbon-11 of progesterone. J. Am. Chem. Soc. 74:1952;5933-5936