title: Transformation of artemisinin by Cunninghamella elegans.
abstract: Semi-synthetic derivatives of the anti-malarial drug artemisinin hold great promise in the search for an effective and economical treatment of chloroquine-resistant forms of malaria. Unfortunately, synthetic functionalization of the artemisinin skeleton is often tedious and/or impractical. We seek to utilize 7beta-hydroxyartemisinin, obtained from microbial transformation, as a semi-synthetic precursor for the synthesis of novel 7beta-substituted artemisinin anti-malarial agents. Here we employ liquid cultures of Cunninghamella elegans as a means for the rational and economical bioconversion of artemisinin to 7beta-hydroxyartemisinin in 78.6% yield. In addition, there were three other bioconversion products: 7beta-hydroxy-9alpha-artemisinin (6.0%), 4alpha-hydroxy-1-deoxoartemisinin (5.4%), and 6beta-hydroxyartemisinin (6.5%).
authors.affiliation: Department of Medicinal Chemistry, University of Mississippi, University, MS 38677-1848, USA.
authors.forename: I A
authors.initials: IA
authors.lastname: Parshikov
authors.forename: K M
authors.initials: KM
authors.lastname: Muraleedharan
authors.forename: M A
authors.initials: MA
authors.lastname: Avery
authors.forename: J S
authors.initials: JS
authors.lastname: Williamson
mesh_terms: D000962:Antimalarials / Q000737:chemistry; D037621:Artemisinins / Q000737:chemistry / Q000378:metabolism*; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D017077:Culture Media, Conditioned; D020093:Cunninghamella / Q000254:growth & development / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: C519571:7-hydroxyartemisinin; D000962:Antimalarials; D037621:Artemisinins; D017077:Culture Media, Conditioned; D012717:Sesquiterpenes; C031327:artemisinin