Eucalyptus perriniana

The metabolism of taxol by Eucalyptus perriniana cell suspension cultures has been recently reported to induce hydrolyses of ester bonds at C-13, C-10 and C-2 [222]. At this moment only very few data have been published about the microbial metabolism of taxoid compounds only site specific hydrolyses of acyl side-chains at C-13 or C-10 by extracellular and intracellular esterases of Nocar-dioides albus SC13,911 and N. luteus SC13,912, respectively, have been reported [223]. On the other hand, Hu et al. [224-226] have recently described some fungal biotransformations of related natural taxane diterpenes extracted from Chinese yews or their cell cultures, in order to obtain new active substances or precursors for hemisynthesis. The taxadiene 145, a 14 -acetylated derivative... 

FIGURE 19.67 Biotransformation of (-)-(137b) and (+)-menthol (137b ) by Eucalyptus perriniana suspension cells. (Modi ed from Hamada, H. et al., Glycosylation of monoterpenes by plant suspension cells. Proceedings of 46th TEAC, 2002, pp. 321-322.)... 

FIGURE 20.163 Biotransformation of thymol (580), carvacrol (583), and eugenol (586) by Eucalyptus perriniana cells. 

FIGURE 20.164 Biotransformation of hinokitiol (589) by Eucalyptus perriniana cells. 

Furuya, T., Y. Asada, Y. Matsuura, S. Mizobata, and H. Hamada, 1997. Biotransformation of p thujapiicin by cultured cells of Eucalyptus perriniana. 46 1355-1358. 

Perillyl alcohol (74 ) was glycosylated by Eucalyptus perriniana suspension cells to (-)-perillyl alcohol monoglucoside (376 ) and diglucoside (377 ) (Hamada et al., 2002 Yonemoto et al, 2005) (Figure 14.101). 

FIGURE 14.101 Biotransfonnation of (-)-perillyl alcohol (74 ) by Eucalyptus perriniana suspension cell. (Modified from Hamada, H. etal., 2002. Proc. 46th TEAC, pp. 321-322 Yonemoto, N. et al., 2005. Proc. 49th TEAC, pp. 108-110.)... 

Hinokitiol (589), which is easily obtained from cell suspension cultures of Thujopsis dolabrata and possesses potent antimicrobial activity, was incubated with cultured cells of Eucalyptus perriniana for 7 days to give its monoglucosides (590, 591, 32%) and gentiobiosides (592, 593) (Furuya et al 1997, Hamada et al., 1998) (Figure 15.164). 

Shimoda, K., Y. Kondo, T. Nishida, H. Hamada, N. Nakajima, and H. Hamada, 2006. Biotransformation of thymol, carvacrol, and engenol by cnltured cells of Eucalyptus perriniana. Phytochemistry, 67 2256-2261. 

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