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Microbial Transformation of Sesquiterpenes, (−)‐ Ambrox ® and (+)‐Sclareolide
Author(s) -
Choudhary M. Iqbal,
Musharraf Syed Ghulam,
Sami Amtul
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490238
Subject(s) - chemistry , triol , diol , sesquiterpene , stereochemistry , hydroxylation , fermentation , biotransformation , bond cleavage , organic chemistry , enzyme , catalysis
The microbial transformation of (−)‐ Ambrox ® ( 1 ), a perfumery sesquiterpene, by a number of fungi, by means of standard two‐stage‐fermentation technique, afforded ambrox‐1 α ‐ol ( 2 ), ambrox‐1 α ,11 α ‐diol ( 3 ), ambrox‐1 α ,6 α ‐diol ( 4 ), ambrox‐1 α ,6 α ,11 α ‐triol ( 5 ), ambrox‐3‐one ( 6 ), ambrox‐3 β ‐ol ( 7 ), ambrox‐3 β ,6 β ‐diol ( 8 ), 13,14,15,16‐tetranorlabdane‐3,8,12‐triol ( 9 ), and sclareolide ( 10 ) ( Schemes 1 and 2 ). Further incubation of compound 10 with Cunninghamella elegans afforded 3‐oxosclareolide ( 11 ), 3 β ‐hydroxysclareolide ( 12 ), 2 α ‐hydroxysclareolide ( 13 ), 2 α ,3 β ‐dihydroxysclareolide ( 14 ), 1 α ,3 β ‐dihydroxysclareolide ( 15 ), and 3 β ‐hydroxy‐8‐episclareolide ( 16 ) ( Scheme 3 ). Metabolites 2 – 5, 12, 13 , and 16 were found to be new compounds. The major transformations include a reaction path involving hydroxylation, ether‐bond cleavage and inversion of configuration. Metabolites 11 – 16 of sclareolide showed significant phytotoxicity ( Table 1 ). The structures of the metabolites were characterized on the basis of spectroscopic techniques.