FIGURE 14.148 Biotransformation of (+)-a-pinene (4) by Pseudomonas fluorescens NCIMB 11671. (Modified from Best, D.J. et al., 1987. Biotransform., 1: 147-159.)
borneol (36). A probable pathway has been proposed for the terminal oxidation of ß-isopropylpimelic acid (248) in the PL strain and PIN 18 (Shukala and Bhattacharyya, 1968).
Pseudomonas PX 1 biotransformed (+)-a-pinene (4) to give (+)-cis-thujone (29) and (+)-trans-carveol (81a) as major compounds. Compounds 81a, 171, 173, and 178 have been identified as fermentation products (Gibbon and Pirt, 1971; Gibbon et al., 1972) (Figure 14.150).
Aspergillus niger TBUYN-2 biotransformed (-)-a-pinene (4') to give (-)-a-terpineol (34') and (-)-trans-sobrerol (43a') (Noma et al., 2001). The mosquitocidal (+)-(1R,2S,4R)-1-p-menthane-2,8-diol (50a') was also obtained as a crystal in the biotransformation of (-)- a-pinene (4') by Aspergillus niger TBUYN-2 (Noma et al., 2001; Noma, 2007) (Figure 14.151).
(1R)-(+)-a-Pinene (4) and its enantiomer (4') were fed to Spodptera litura to give the corresponding (+)- and (-)-verbenones (24 and 24') and (+)- and (-)-myrtenols (5 and 5') (Miyazawa et al., 1996c) (Figure 14.152).
(-)-a-Pinene (4') was treated in human liver microsomes CYP 2B6 to afford (-)-trans-verbenol (23') and (-)-myrtenol (5') (Sugie and Miyazawa, 2003) (Figure 14.153).
In rabbit, (+)-a-pinene (4) was metabolized to (-)-trans-verbenols (23) as the main metabolites together with myrtenol (5) and myrtenic acid (7). The purities of (-)-verbenol (23) from (-)- (4'), (+)- (4), and (+/-)-a-pinene (4 and 4') was 99%, 67%, and 68%, respectively. This means that the biotransformation of (-)-4' in rabbit is remarkably efficient in the preparation of (-)-trans-verbenol (23a) (Ishida et al., 1981b) (Figure 14.154).
(-)-a-Pinene (4') was biotransformed by the plant pathogenic fungus Botrytis cinerea to afford 3a-hydroxy-(-)-ß -pinene (2a', 10%), 8-hydroxy-(-)-a-pinene (434', 12%), 4ß -hydroxy-(-)-pinene-6-one (468', 16%), and (-)-verbenone (24') (Farooq et al., 2002) (Figure 14.155).
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