Nerolidol biotransformation

Hrdlicka, P.J., A.B. Sorensen, B.R. Poulsen, G.J.G. Ruijter, J. Visser. and J.J.L. Iversen. 2004. Characterization of nerolidol biotransformation based on indirect on-line estimation of biomass concentration and physiological state in bath cultures of Aspergillus niger. Bw dwoL ]., 20 368-376. 

Finally, a Japanese group also studied the biotransformation of Z- and -nerolidol [137,138] with the plant pathogenic fungus Glomerella cingulata. Both Z- and -nerolidol were mainly oxidised at the remote double bond. Z-Nerolidol (162) was transformed into (Z)-3,7,11-trimethyl-l,6-dodecadiene-3,10,11-triol (164) while -nerolidoI (158) was mainly oxidised to ( )-3,7,11-trimethyl-l,6-dodecadiene-3,ll-diol (171) only small amounts of ( )-3,7,11-trimethyl-l,6-dodecadiene-3,10,11-triol (160) were obtained, Fig. (34). 

Hydroxy-frani-nerolidol (472a) is an important precursor in the synthesis of interesting avor of a-sinensal. Hrdlicka et al. (2004) reported the biotransformation of trans- (469) and CM-nerolidol (462) and cis-/trans-mixture of nerolidol using repeated batch culture of A. niger grown in... 

FIGURE 20.136 Biotransformation of c/s nerolidol (462) and cis-geranyl acetone (463) by Glotnerella cingulata. 

FIGURE 20.137 Biotransformation of frans-nerolidol (469) and frans-geranyl acetone (470) by Glomerella... 

FIGURE 20.138 Biotransformation of cis- (462) and fran -nerolidol (469) hy Aspergillus niger. 

Miyazawa, M., H. Nakai, and H. Kameoka, 1995b. Biotransformation of cycUc terpenoids, ( )-cis-nerolidol and nerylacetone, by plant pathogenic fungus, Glomerella cingulata. Phytochemistry. 40 1133-1137. 

FIGURE 15.142 Biotransformation of 9-oxo-rraro-nerolidol (487) hy Aspergillus niger. 

Biotransformation of linalool gave both tetrahydrofurans and tetrahydropyranes, but the biotransformation of trans-nerolidol discussed above produced only tetrahydrofurans. A set of homologous dimethylalkadienes were used as substrates to be epoxidized with the fungus Diplodia gossypina. It turned out that dimethylhexa-2,4-diene 53 could not form any tetrahydrofuran probably because the second double bond could not be attacked (Fig. 8). All the other hydrocarbons like 47 and 50 formed the tetrahydrofuran derivative (49 and 52) and sometimes also the tetrahydropyrane compound, but in much lower yields. 

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