Hydroxylation of 10-deoxoartemisinin by Cunninghamella elegans.
The microbial metabolism of 10-deoxoartemisinin (1), a derivative of the antimalarial drug artemisinin, was investigated. Various strains of fungi were investigated for their ability to transform 1. Of these microorganisms, only Cunninghamella elegans was capable of transforming 1 to 5beta-hydroxy-10-deoxoartemisinin (2), 4alpha-hydroxy-1,10-deoxoartemisinin (3), and 7beta-hydroxy-10-deoxoartemisinin (4). The metabolites 2 and 4 retained an intact peroxide group and are therefore useful scaffolds for synthetic modification in the search for new antimalarial agents.
Parshikov
Igor A
IA
Department of Medicinal Chemistry, University of Mississippi, University, Mississippi 38677-1848, USA.
Muraleedharan
Kannoth M
KM
Miriyala
Bruhaspathy
B
Avery
Mitchell A
MA
Williamson
John S
JS
D000962:Antimalarials / Q000737:chemistry*; D037621:Artemisinins / Q000138:chemical synthesis* / Q000737:chemistry*; D020093:Cunninghamella / Q000378:metabolism*; D006900:Hydroxylation; D015394:Molecular Structure; D009089:Mucor / Q000378:metabolism; D010407:Penicillium / Q000378:metabolism; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000962:Antimalarials; D037621:Artemisinins; D012717:Sesquiterpenes; C063801:deoxoartemisinin