Transformation of artemisinin by Cunninghamella elegans

Applied Microbiology and Biotechnology

Volumn 64, Issue 6, 2004, Pages 782-786

  Parshikov, I A ^a   Muraleedharan, K M ^a   Avery, M A ^a   Williamson, J S ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEMISININ; ARTEMISININ DERIVATIVE; CHLOROQUINE; LACTONE; SESQUITERPENE;

DRUG DEVELOPMENT; MALARIA;

ANTIMALARIAL ACTIVITY; ARTICLE; BIOTRANSFORMATION; CUNNINGHAMELLA; DRUG STRUCTURE; ECONOMIC ASPECT; FUNGUS CULTURE; METHODOLOGY; MICROORGANISM; MOLECULE; NONHUMAN;

ANTIMALARIALS; ARTEMISININS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CULTURE MEDIA, CONDITIONED; CUNNINGHAMELLA; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SESQUITERPENES;

CUNNINGHAMELLA; CUNNINGHAMELLA ELEGANS;

EID: 3142770578     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-003-1524-z     Document Type: Article

References (21)

1. Abourashed EA, Hufford CD (1996) Microbial transformation of artemether. J Nat Prod 59:251-253
2. Abourashed EA, Clark AM, Hufford CD (1999) Microbial models of mammalian metabolism of xenobiotics: an updated review. Curr Med Chem 6:359-374
3. Avery MA, Alvim-Gaston M, Woolfrey JR (1999) Synthesis and structure-activity relationships of peroxidic antimalarials based on artemisinin. Adv Med Chem 4:125-217
4. Azerad R (1999) Microbial models for drug metabolism. Adv Biochem Eng Biotechnol 63:169-218
5. 13C-NMR assignments of Artemisinin. (Qinghaosu). J Nat Prod 51:1273-1276
6. Ekthawatchai S, Kamchonwongpaisan S, Konsaeree P, Tarnchompoo B, Thebtaranonth Y, Yuthavong Y (2001) C-16 Artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene. J Med Chem 44:4688-4695
7. Fiaux de Medeiros S, Avery MA, Avery B, Leite SGF, Freitas ACC, Williamson JS (2002) Biotransformation of 10-deoxoartemisinin to its 7β-hydroxy derivative by Mucor ramannianus. Biotechnol Lett 24:937-941
8. Grogan GJ, Holland HL (2000) The biocatalytic reactions of Beauveria spp. J Mol Catal B 9:1-32
9. Hu Y, Ziffer H, Li G, Yen HJC (1992) Microbial oxidation of the antimalarial drug arteether. Bioorg Chem 20:148-154
10. Hufford CD, Lee IS, El-Sohly HN, Chi HT, Baker JK (1990) Structure elucidation and thermospray high-performance liquid chromatography/mass spectroscopy (HPLC/MS) of the microbial and mammalian metabolites of the antimalarial arteether. Pharm Res 7:923-927
11. Hufford CD, Khalifa SI, Orabi KY, Wiggers FT (1995) 1α- Hydroxyarteether, a new microbial transformation product. J Nat Prod 58:751-755
12. Lee IS, Hufford CD (1990) Metabolism of antimalarial sesquiterpene lactones. Pharmacol Ther 48:345-355
13. Lee IS, El-Sohly HN, Croom EM, Hufford CD (1989) Microbial metabolism studies of the antimalarial sesquiterpene artemisinin. J Nat Prod 52:337-341
14. Mattelli A, Volonterio A, Gulletta M, Galimberti L, Maroccolo S, Gaiera G, Giani G, Rossi M, Dorigoni M, Bellina L, Orlando G, Bisoffi Z, Castelli F (2001) Malaria in illegal immigrants, Italy. Emerg Infect Dis 7:1055-1058
15. Orabi KY, Galay AM, Ibrahim ARS, El-Feraly FS, Khalifa SI, El-Sohly HN (1999) Microbial metabolism of artemisitene. Phytochemistry 51:257-261
16. Parshikov IA, Terent'ev PB, Modyanova LV (1994) Microbiological transformation in a series of nitrogen-containing heterocycles. Chem Heterocycl Compd 30:1308-1330
17. Posner GH, Parker MH, Northrop J, Elias JS, Ploypradith P, Xie S, Shapiro TA (1999) Orally active, hydrolytically stable, semi-synthetic, antimalarial trioxanes in the artemisinin family. J Med Chem 42:300-304
18. Sutherland JB, Evans FE, Freeman PF, Williams AJ, Deck J, Cerniglia CE (1994) Identifications of metabolites produced by Cunninghamella elegans. Mycology 86:117-120
19. Zhan J, Guo H, Dai J, Zhang Y, Guo D (2002a) Microbial transformation of artemisinin by Cunninghamella echinulata and Aspergillus niger. Tetrahedron Lett 43:4519-4521
20. Zhan J, Zhang Y, Guo H, Han J, Ning L, Guo D (2002b) Microbial metabolism of artemisinin by Mucor polymophosporus and Aspergillus niger. J Nat Prod 65:1693-1695
21. Ziffer H, Hu Y, Pu Y (1992) Beauveria sulfurescens mediated oxidation of dihydroartemisinin derivatives. NATO ASI Ser C Math Phys Sci 381:361-373