Aromadendrane transformations by Curvularia lunata ATCC 12017.
The naturally occurring sesquiterpene squamulosone (1), isolated from Hyptis verticillata (Labiatae), was synthetically reduced to five analogues that were identified as (1S,10S)-9alpha-hydroxy-allo-aromadendrane (2), (1R,10R)-9beta-hydroxyaromadendrane (3), (1S,10S)-allo-aromadendran-9-one (4), (1R,10R)-aromadendran-9-one (5) and aromadendra-1,9-diene (6). Each congener was incubated with the fungus Curvularia lunata ATCC 12017 in two different growth media. All the substrates except the deoxy compound 6 underwent a simple redox reaction. Ketone 5 additionally experienced remote hydroxylation while analogue 6, possessing a conjugated diene system, was most extensively metabolised. The substrates and products presented here, but one, are all novel.
Collins
Dwight O
DO
Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica.
Reynolds
William F
WF
Reese
Paul B
PB
D003470:Culture Media; D005658:Fungi / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000737:chemistry* / Q000378:metabolism*
D003470:Culture Media; D012717:Sesquiterpenes; C436754:squamulosone