FIGURE 15.116 Biotransformation of (+)-sclareolide (402) by Aspergillus niger.
430c) of which compounds 425, 427, and 428 are the major metabolites (Aleu et al., 1999) while plant pathogenic fungus Glomerella cingulata converted the same substrate to 5-hydroxy- (426) and 5,8-dihydroxy derivative (429) (Figure 15.122).
In order to confirm the formation of 429 from 426, the latter product was reincubated in the same medium including Glomerella cingulata to afford 429 (Miyazawa et al., 1997b) (Figure 15.123).
Patchouli acetate (431) was also treated in the same medium to give 426 and 429 (Matsui and Miyazawa, 2000). 5-Hydroxy-a-patchoulene (432) was incubated with Glomerella cingulata to afford 1a-hydroxy derivative (426) (Miyazawa et al., 1998a).
(-)-a-Longipinene (433) was treated with Aspergillus niger to afford 12-hydroxylated product (434) (Sakata et al., 2007).
Ginsenol (435), which was obtained from the essential oil of Panax ginseng, was incubated with Botrytis cinerea to afford four secondary alcohols (436-439) and two cyclohexanone derivatives (440) from 437 and 441 from 438 or 439. Some of the oxygenated products were considered as potential antifungal agents to control Botrytis cinerea (Aleu et al., 1999a) (Figures 15.124 and 15.125).
(+)-Isolongifolene-9-one (442), which was isolated from some cedar trees was treated in Glomerella cingulata for 15 days to afford two primary alcohols (443, 444) and a secondary alcohol (445) (Sakata and Miyazawa, 2006) (Figure 15.126).
Choudhary et al. (2005) reported that fermentation of (-)-isolongifolol (445a) with Fusarium lini resulted in the isolation of three metabolites, 10-oxo- (445b), 10a-hydroxy- (445c), and 9a-hydroxyisolngifolol (445d). Then the same substrate was incubated with Aspergillus niger to yield the products 445c and 445d. Both 445c and 445d showed inhibitory activity against butylcholinesterease enzyme in a concentration-dependent manner with IC50 13.6 and 299.5 |mM, respectively (Figure 15.127).
(+)-Cycloisolongifol-5ß-ol (445e) was fermented with Cunninghamella elegans to afford three oxygenated metabolites: 11-oxo- (445f), 3ß-hydroxy- (445g), and 3ß,11a-dihydroxy derivative (445h) (Choudhary et al., 2006a). (Figure 15.128).
A daucane-type sesquiterpene derivative, lancerroldiol p-hydroxybenzoate (446) was hydroge-nated with cultured suspension cells of the liverwort, Marchantia polymorpha to give 3,4-dihydrolancerodiol (447) (Hegazy et al., 2005) (Figure 15.129).
Widdrane sesquiterpene alcohol (448) was incubated with Aspergillus niger to give an oxo and an oxy derivatives (449, 450) (Hayashi et al., 1999) (Figure 15.130).
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