Biotransformation of artemisinin mediated through fungal strains for obtaining derivatives with novel activities

Scientia Pharmaceutica

Volumn 77, Issue 1, 2009, Pages 87-95

  Srivastava, Suchita ^a   Luqman, Suaib ^a   Fatima, Atiya ^a   Darokar, Mahendra P ^a   Negi, Arvind S ^a   Kumar, J K ^a   Shanker, K ^a   Chanotiya, Chandan S ^a   Tandon, Sudeep ^a   Khanuja, Suman P S ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

Author keywords

Antibacterial; Artemisinin; Aspergillus flavus; Biotransformation; Deoxyartemisinin

Indexed keywords

ARTEMISININ; ARTEMISININ DERIVATIVE; DEOXYARTEMISININ; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS NIGER; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; FUNGAL STRAIN; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PICHIA PASTORIS; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STREPTOCOCCUS MUTANS; STRUCTURE ACTIVITY RELATION;

EID: 63149121134     PISSN: 00368709     EISSN: 22180532     Source Type: Journal    
DOI: 10.3797/scipharm.0803-15     Document Type: Article

References (37)

1. Klayman DL. Qinghaosu (artemisinin): an antimalarial drug from China. Science. 1985; 228: 1049-1055. doi:10.1126/science.3887571
2. Liu C, Zhao Y, Wang Y. Artemisinin: current state and perspectives for biotechnological production of an antimalarial drug. Appl Microbiol Biotechnol. 2006; 72: 11-20. doi:10.1007/s00253-006-0452-0
3. Lin AJ, Klayman DL, Hoch JM, Silverton JV, George CF. Thermal Rearrangement and Decomposition Products of Artemisinin (Qinghaosu). J Org Chem. 1985; 50: 4504-4508. doi:10.1021/jo00223a017
4. Lee IS, El-Sohly HN, Croom EM, Hufford CD. Microbial metabolism studies of the antimalarial sesquiterpene artemisinin. J Nat Prod 1989; 52: 337-341. doi:10.1021/np50062a020
5. Webster HK, Lehnert EK. Chemistry of artemisinin: an overview. Trans R Soc Trop Med Hyg. 1994; 88: 27-S29. doi:10.1016/0035-9203(94)90467-7
6. Meshnick SR, Taylor TE, Kamchonwongpaisan S. Artemisinin and the antimalarial endoperoxides: From herbal remedy to targeted chemotherapy. Microbiol Rev. 1996; 60: 301-315. PMid:8801435
7. Hufford CD, Khalifa SI, Orabi KY, Wiggers FT. 1 α-Hydroxyarteether, a new microbial transformation product. J Nat Prod. 1995; 58: 751-755. doi:10.1021/np50119a016
8. Orabia KA, Galala AM, Abdel-Rahim S Ibrahima, Farouk S El-Feralya, Sherief I Khalifab, Hala N El-Sohlyc. Microbial metabolism of artemisitene. Phytochemistry. 1999; 51: 257-261. doi:10.1016/S0031-9422(98)00770-5
9. Sy L, Hui S, Cheung K, Brown, GD. A rearranged hydroperoxide from the reduction of artemisinin. Tetrahedron. 1997; 53: 7493-7500. doi:10.1016/S0040- 4020(97)00444-4
10. El-Feraly FS, Al-Meshal IA, Al-Yahya MA, Hifnawy MS. On the possible role of qinghaoacid in the biosynthesis of artemisinin. Phytochemistry. 1986; 25: 2777-2778. doi:10.1016/S0031-9422(00)83739-5
11. Begue JP, Bonnet DD. The future of antimalarials: artemisinins and synthetic endoperoxides. Drugs Future. 2005; 30: 509-518. doi:10.1358/dof.2005. 030.05.901987
12. Avery MA, Alvim-Gaston M, Woolfrey JR. Synthesis and structure-activity relationships of peroxidic antimalarials based on artemisinin. Adv Med Chem. 1999; 4: 125-217. doi:10.1016/S1067-5698(99)80005-4
13. Parshikov IA, Miriyala B, Muraleedharan KM, Illendula A, Avery MA, Williamson JS. Biocatalysis of the Antimalarial Artemisinin by Mucor ramannianus strains. Pharm Biol. 2005; 43: 579-582. doi:10.1080/ 13880200500301597
14. Parshikov IA, Muraleedharan KM, Miriyala B, Avery MA, Williamson JS. Microbial transformation of artemisinin to 5-hydroxyartemisinin by Eurotium amstelodami and Aspergillus niger. J Ind Microbiol Biotechnol. 2006; 33: 349-352. doi:10.1007/s10295-005-0071-2
15. Zhan J, Guo H, Dai J, Zhang Y, Guo D. Microbial transformation of artemisinin by Cunninghamella echinulata and Aspergillus niger. Tetrahedron Lett. 2002; 43: 4519-452. doi:10.1016/S0040-4039(02)00812-2
16. Zhan J, Zhang Y, Guo H, Han J, Ning L, Guo D. Microbial metabolism of artemisinin by Mucor polymophosporus and Aspergillus niger. J Nat Prod 2002; 65: 1693-1695. doi:10.1021/np020113r
17. Parshikov IA, Muraleedharan KM, Avery MA, Williamson JS. Transformation of artemisinin by Cunninghamella elegans. Appl Microbiol Biotechnol. 2004; 64: 782-786. doi:10.1007/s00253-003-1524-z
18. Parshikov IA, Muraleedharan KM, Miriyala B, Avery MA, Williamson JS. Hydoxylation of Deoxoartemisinin by Cunninghamella elegans. J Nat Prod 2004; 67: 1595-1597. doi:10.1021/np040089c
19. Parshikov IA, Muraleedharan K M, Miriyala B, Avery MA, Williamson JS. Hydroxylation of 10-deoxoartemisinin to 15-hydroxy-10-deoxoartemisinin by Aspergillus niger. Biotechnol Lett. 2004; 26: 607-610. doi:10.1023/B:BILE.0000021965.55420.e9
20. Liu JH, Chen YG, Yu BY, Chen YJ. A novel ketone derivative of artemisinin biotransformed by Streptomyces griseus ATCC 13273. Bioorg Med Chem Lett. 2006; 16: 1909-1912. doi:10.1016/j.bmcl.2005.12.076
21. Venisetty RK, Ciddi V. Application of microbial biotransformation for the new drug discovery using natural drugs as substrates. Curr Pharm Biotechnol. 2003; 4: 153-67. doi:10.2174/1389201033489847
22. García-Granados A, Liñán E, Martínez A, Onorato ME, Parra A, AriasJM. Synthesis of enantio-manoyl oxides: modifiers of the activity of adenylatecyclase enzyme. Phytochemistry. 1995; 38: 287-93. doi:10.1016/0031-9422(94)00549-9
23. Hikino H, Tokuoka Y, Hikino Y, Takemoto T. Microbial transformation of α-kessyl alcohol to kessyl glycol and kessane-2β,7-diol. Tetrahedron. 1968; 24: 3147-3152. doi:10.1016/S0040-4020(01)98721-6
24. Hikino H, Aota K, Tokuoka Y, Takemoto T. Biochemical synthesis. II. Microbial transformation of cyperotundone to eugenol and isopatchoul-4-en-3-on- 8-alpha-ol. Chem Pharm Bull. 1968; 16: 1088-1090. PMid:5710071
25. Clark AM, Hufford CD. Microbial transformations of the sesquiterpene lactone costunolide J Chem Soc Perkin Trans. 1979; 1: 3022. doi:10.1039/ P19790003022
26. Elmarakby SA, Clark AM, Baker JK, Hufford CD. Microbial metabolism of bornaprine, 3-(diethylamino)propyl 2-phenylbicyclo[2.2.1]heptane-2-carboxylate. J Pharm Sci. 1986; 75: 614-618. doi:10.1002/jps.2600750620
27. Hufford CD, Lee IS, El-Sohly HN, Chi HT, Baker JK. Structure elucidation and thermospray high-performance liquid chromatography/mass spectroscopy (HPLC/MS) of the microbial and mammalian metabolites of the antimalarial arteether. Pharm Res. 1990; 7: 923-927. doi:10.1023/A:1015993722846
28. Lee IS, Hufford CD. Metabolism of antimalarial sesquiterpene lactones. Pharmacol Ther. 1990; 48: 345-355. doi:10.1016/0163-7258(90)90053-5
29. Ziffer H, Hu Y, Pu Y. Beauveria sulfurescens mediated oxidation of dihydroartemisinin derivatives. NATO ASI Ser C Math Phys Sci. 1992; 381: 361-373.
30. Abourashed EA, Hufford CD. Microbial transformation of artemether. J Nat Prod. 1996; 59: 251-253. doi:10.1021/np960060b
31. Grogan GJ, Holland HL. The biocatalytic reactions of Beauveria spp. J Mol Catal B. 2000; 9: 1-32. doi:10.1023/A:1015516929682
32. Fiaux de Medeiros S, Avery MA, Avery B, Leite SGF, Freitas ACC, Williamson JS. Biotransformation of 10-deoxoartemisinin to its 7p-hydroxy derivative by Mucor ramannianus. Biotechnol Lett. 2002; 24: 937-941. doi:10.1016/0002-9343(65)90096-3
33. Petersdorf RG, Sherris JC. Methods and significance of in vitro testing of bacterial sensitivity to drugs. Am J Med. 1965; 39: 766-779. doi:10.1016/0002-9343(65)90096-3
34. th Edn. The American Society of Microbiology Press: Washington DC, 1999: 1526-1543.
35. Bouwmeester HJ, Wallaart TE, Janssen MHA, Loo BV, Jansen BJM, Posthumus MA, Schmidt CO, Kraker JD, Konig WA, Franssen MCR. Amorpha 4, 11-diene synthase catalyses the first probable step in artemisinin biosynthesis. Phytochemistry. 1999; 52: 843-854. doi:10.1016/S0031-9422(99)00206-X
36. Wallaart TE, van Uden W, Lubberink HG, Woerdenbag HJ, Pras N, Quax WJ. Isolation & identification of dihydroartemisincic acid from Artemisia annua & its possible role in the biosynthesis of artemisinin. J Nat Prod. 1999; 62: 430-433. doi:10.1021/np980370p
37. Bertea CM, Freije JR, Vander Woude H, Verstappen FWA, Perk L, Marquez V. De Kraker JW, Posthumus MA, Jansen BJM, de Groot A Franssen MCR, Bouweester HJ. Identification of intermediates & enzymes involved in the early steps of artemisinin biosynthesis in A annua. Planta Med. 2005; 71: 40-47. doi:10.1055/s-2005-837749