Microbial transformation of pyrethrosin.
Microbial transformation of the germacranolide pyrethrosin (1) using Rhizopus nigricans NRRL 1477 has resulted in the isolation of 6 alpha-acetoxy-1 beta,4 alpha-dihydroxy-5,7 alpha H,8 beta H-eudesm-11 beta,13-dihydro-8,12-olide (5), a new eudesmanolide-type metabolite, in addition to the previously reported eudesmanolides: 2, 3, 4, and 6. The structure elucidation of these metabolites was based primarily on 1D and 2D NMR analyses. The isolated metabolites exhibited cytotoxic, antifungal, and antiprotozoal activities.
Galal
A M
AM
National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Mississippi 38677, USA. amgalalv@yahoo.com
D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001711:Biotransformation; D002176:Candida albicans / Q000187:drug effects; D002294:Carcinoma, Squamous Cell; D003455:Cryptococcus neoformans / Q000187:drug effects; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008545:Melanoma; D015394:Molecular Structure; D010051:Ovarian Neoplasms; D010963:Plasmodium falciparum / Q000187:drug effects; D011722:Pyrethrins / Q000737:chemistry / Q000378:metabolism*; D012233:Rhizopus / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism* / Q000494:pharmacology; D045787:Sesquiterpenes, Eudesmane; D014407:Tumor Cells, Cultured / Q000187:drug effects
C436783:6alpha-acetoxy-1beta,4alpha-dihydroxy-5,7alpha H,8 beta H-eudesm-11beta,13-dihydro-8,12-olide; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000962:Antimalarials; D000972:Antineoplastic Agents, Phytogenic; D011722:Pyrethrins; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; C003255:pyrethrosin