A novel dihydroxylated derivative of artemisinin from microbial transformation

Fitoterapia

Volumn 120, Issue , 2017, Pages 93-97

  Zhan, Yulian ^a,b   Wu, Yunshan ^c,d   Xu, Fangfang ^c   Bai, Yunpeng ^b   Guan, Yezhi ^e   Williamson, John S ^d   Liu, Bo ^c,d  

^a GUILIN UNIVERSITY OF ELECTRONIC TECHNOLOGY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c GUANGDONG PROVINCIAL HOSPITAL OF CHINESE MEDICINE   (China)

^d UNIVERSITY OF MISSISSIPPI   (United States)

^e GUANGZHOU UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

Antimalarial drugs; Artemisinin; Cunninghamella elegans; Microbial transformation

Indexed keywords

6BETA 7 ALPHA DIHYDROXYARTEMISININ; 7 ALPHA HYDROXYARTEMISININ; 7 BETA HYDROXYARTEMISININ; ANTIMALARIAL AGENT; ARTEMISININ DERIVATIVE; BETA HYDROXYARTEMISININ; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; BACTERIUM TRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CUNNINGHAMELLA ELEGANS; DRUG HYDROXYLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CHEMISTRY; CUNNINGHAMELLA; HYDROXYLATION; METABOLISM; STRUCTURE ACTIVITY RELATION;

ANTIMALARIALS; ARTEMISININS; BIOTRANSFORMATION; CUNNINGHAMELLA; HYDROXYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85020316579     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2017.05.015     Document Type: Article

References (11)

1. Avery, M.A., Alvim-Gaston, M., Woolfrey, J.R., Synthesis and structure-activity relationships of peroxidic antimalarials based on artemisinin. Adv. Med. Chem. 4 (1999), 125–217.
2. Posner, G.H., Parker, M.H., Northrop, J., Elias, J.S., Ploypradith, P., Xie, S., Shapiro, T.A., Orally active, hydrolytically stable, semisynthetic, antimalarial trioxanes in the artemisinin family. J. Med. Chem. 42 (1999), 300–304.
3. Zhan, Y.L., Liu, H., Wu, Y.S., Wei, P.Y., Chen, Z.C., Williamson, J.S., Biotransformation of artemisinin by Aspergillus niger. Appl. Microbiol. Biotechnol. 99 (2015), 3443–3446.
4. Gaur, R., Darokar, M.P., Ajayakumar, P.V., Shukla, R.S., Bhakuni, R.S., In vitro antimalarial studies of novel artemisinin biotransformed products and its derivatives. Phytochemistry 107 (2014), 135–140.
5. Parshikov, I.A., Miriyala, B., Avery, M.A., Williamson, J.S., Hydroxylation of 10-deoxoartemisinin to 15-hydroxy-10-deoxoartemisinin by Aspergillus niger. Biotechnol. Lett. 26 (2004), 607–610.
6. Parshikov, I.A., Muraleedharan, K.M., Avery, M.A., Williamson, J.S., Transformation of artemisinin by Cunninghamella elegans. Appl. Microbiol. Biotechnol. 64 (2004), 782–786.
7. Parshikov, I.A., Miriyala, B., Muraleedharan, K.M., Avery, M.A., Williamson, J.S., Microbial transformation of artemisinin to 5-hydroxyartemisinin by Eurotium amstelodami and Aspergillus niger. J. Ind. Microbiol. Biotechnol. 33 (2006), 349–352.
8. Zhan, J.X., Zhang, Y.X., Guo, H.Z., Han, J., Ning, L.L., Guo, D.A., Microbial metabolism of artemisinin by Mucor polymorphosporus and Aspergillus niger. J. Nat. Prod. 65 (2002), 1693–1695.
9. Goswami, A., Saikia, P.P., Barua, N.C., Bordoloi, M., Yadav, A., Bora, T.C., Gogoi, B.K., Saxena, A.K., Suri, N., Sharma, M., Bio-transformation of artemisinin using soil microbe: direct C-acetoxylation of artemisinin at C-9 by Penicillium simplicissimum. Bioorg. Med. Chem. Lett. 20 (2010), 359–361.
10. Xu, F.F., Liao, K.S., Liu, Y.H., Zhang, Z.B., Guo, D.A., Su, Z.R., Liu, B., Biotransformation of patchoulol by Cunninghamella echinulata var. elegans. Fitoterapia 109 (2016), 201–205.
11. Liu, J.H., Chen, Y.G., Yu, B.Y., Chen, Y.J., A novel ketone derivative of artemisinin biotransformed by Streptomyces griseus ATCC 13273. Bioorg. Med. Chem. Lett. 16 (2006), 1909–1912.