FIGURE 15.128 Biotransformation of (+)-cycloisolongifol-5ß-ol (445e) by Cunninghamella elegans.
The fermentation of (-)-b -caryophyllene oxide (453) using Botrytis cinerea and the isolation of the metabolites were carried out by Duran et al. (1999) Kobuson (457w) was obtained with fourteen products (457s-457u, 457x). Diepoxides 457t and 457u could be the precursors of epimeric alcohols 457q and 457y obtained through reductive opening of the C2,C11-epoxide. The major reaction paths are stereoselective epoxidation and introduction of hydroxyl group at C3. Compound 457ae has a caryolane skeleton (Figure 15.134).
When isoprobotryan-9a-ol (458) produced from isocaryophyllene was incubated with Botrytis cinerea, it was hydroxylated at tertiary methyl groups to give three primary alcohols (459-461) (Aleu et al., 2002) (Figure 15.135).
Acyclic sesquiterpenoids, racemic cis-nerolidol (462), and nerylacetone (463) were treated by the plant pathogenic fungus, Glomerella cingulata (Miyazawa et al., 1995a). From the former substrate, a triol (464) was obtained as the major product. The latter was bioconverted to give the two methyl ketones (465, 467) and a triol (468), among which 465 was the predominant. The C10,C11 diols (464, 465) might be formed from both epoxides of the substrates, followed by the hydration although no C10,C11-epoxides were detected (Figure 15.136).
Racemic trans-nerolidol (469) was also treated in the same fungus to afford w-2 hydroxylated product (471) and C10,C11 hydroxylated compounds (472) as seen in racemic ds-nerolidol (462) (Miyazawa et al., 1996a) (Figure 15.137).
12-Hydroxy-trans-nerolidol (472a) is an important precursor in the synthesis of interesting flavor of a-sinensal. Hrdlicka et al. (2004) reported the biotransformation of trans-(469) and ds-nerolidol
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