Novel microbial transformations of sclareolide.
Fungal catalysis of sclareolide (1) using Mucor plumbeus (ATCC 4740), Cunninghamella blakesleeana (ATCC 9245), Cunninghamella echinulata (ATCC 9244), Curvularia lunata (ATCC 12017) and Aspergillus niger (ATCC 1004), was performed. Cunninghamella blakesleeana (ATCC 9245) metabolized compound 1 to afford O(6)-sclareolide (2), 3beta,6alpha-dihydroxysclareolide (3), 9-hydroxysclareolide (4), along with three known metabolites, 1beta,3beta-dihydroxysclareolide (5), 3-oxosclareolide (6) and 3beta-hydroxysclareolide (7). Biotransformation experiments of compound 1 with Cunninghamella echinulata (ATCC 9244) also yielded two new compounds, 5-hydroxysclareolide (8), and 7beta-hydroxysclareolide (9) along with two known compounds 5 and 7. Spectroscopic methods were used to establish the structures of compounds 2-9. Compounds 2-9 exhibited modest acetylcholinesterase inhibitory activity.
Ata
Athar
A
Department of Chemistry, The University of Winnipeg, Winnipeg, MB Canada R3B 2E9. a.ata@uwinnipeg.ca
Conci
Leigha J
LJ
Betteridge
Jordan
J
Orhan
Ilkay
I
Sener
Bilge
B
D000110:Acetylcholinesterase / Q000187:drug effects; D001711:Biotransformation; D002800:Cholinesterase Inhibitors / Q000494:pharmacology; D004224:Diterpenes / Q000378:metabolism* / Q000494:pharmacology; D005658:Fungi / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet
D002800:Cholinesterase Inhibitors; D004224:Diterpenes; C109395:sclareolide; D000110:Acetylcholinesterase