Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Novel Microbial Transformations of Sclareolide
Athar AtaLeigha J. ConciJordan BetteridgeIlkay OrhanBilge Sener
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2007 Volume 55 Issue 1 Pages 118-123

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Abstract

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 O6-sclareolide (2), 3β,6α-dihydroxysclareolide (3), 9-hydroxysclareolide (4), along with three known metabolites, 1β,3β-dihydroxysclareolide (5), 3-oxosclareolide (6) and 3β-hydroxysclareolide (7). Biotransformation experiments of compound 1 with Cunninghamella echinulata (ATCC 9244) also yielded two new compounds, 5-hydroxysclareolide (8), and 7β-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.

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© 2007 The Pharmaceutical Society of Japan
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