TOBACCO CHEMISTRY .81. BIOTRANSFORMATIONS OF (Z)-ABIENOL USING PLANT-CELL CULTURES OF NICOTIANA-SILVESTRIS

The transformations of (Z)-abienol (1) effected by cell cultures and c ell-free extracts of Nicotiana silvestris and by horseradish peroxidas e have been examined. Although this compound retarded the growth of th e cell cultures in low doses and exhibited a toxic effect in high dose s, a fairly rapid conversion was observed when low to moderate doses o f cells cultivated under light were used. Of the many transformation p roducts encountered twelve were identified. The major ones of these we re (12R,13S)- and (12R,13R)-8, 12-epoxy-14-labden-13-ols (2, 5), (11E) 14,1 5-bisnor-8-hydroxy-11-labden-13-one (11), 12-norambreinolide (10) , 12,15-epoxy-12,14-labdadien-8-ol (12) and 8-drimanol (13), and the m inor (12R,13R)-, (12S,13R)-, (12S,13S)- and (12R,13S)-8,13-epoxy-14-la bden-12-ols (6-9) and (12S, 13S)- and (12S,13R)-8, 12-epoxy-14-labden- 13-ols (3, 4). Horseradish peroxidase also transformed (Z)-abienol int o these products.