Hirokazu Nankai

Biotransformation of (−)-α-bisabolol by plant pathogenic fungus, Glomerella cingulata

Abstract Microbial transformation of (−)-α-bisabolol by Glomerella cingulata has been investigated. (−)-α-Bisabolol was initially transformed to (1S,3R,4R,7S)-3,4-dihydroxy-α-bisabolol and bisabolol oxide B. (1S,3R,4R,7S)-3,4-Dihydroxy-α-bisabolol was further transformed to (1S,3R,4R,7S,10S)-3,4-dihydroxy-bisabolol oxide B. Bisabolol oxide B was also further transformed to (1S,3R,4R,7S,10S)- and (1S,3S,4R,7S,10S)-3,4-dihydroxy-bisabolol oxide B. The structures of the metabolic products were determined by spectroscopic methods. Metabolic pathways of the biotransformation of (−)-α-bisabolol by G. cingulata are also discussed.

Biotransformation of (+)-Cedrol by plant pathogenic fungus, Glomerella cingulata

Microbial transformation of (+)-cedrol has been investigated by using plant pathogenic fungus, Glomerella cingulata. (+)-Cedrol was hydroxylated at the C-3 position, and transformed mainly to 3α-hydroxycedrol and with a smaller amount of 3β-hydroxycedrol. 3α-Hydroxycedrol was further transformed to 8-cedren-3α-ol by dehydration at the C-8 position. In addition, G. cingulata produced a small amount of 12-hydroxycedrol from (+)-cedrol with stereoselective hydroxylation of the methyl group at the C-12 position. The structures of the metabolic products were determined by their spectroscopic data.

Biotransformations of acyclic terpenoids, (±)-cis-nerolidol and nerylacetone, by plant pathogenic fungus, Glomerella cingulata

Microbial transformations of (±)-cis-nerolidol and nerylacetone were investigated using the plant pathogenic fungus, Glomerella cingulata. Both (±)-cis-nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.

Biotransformation of acyclic terpenoid (2E,6E)-farnesol by plant pathogenic fungus Glomerella cingulata

The microbial transformation of (2E,6E)-farnesol was investigated using the plant pathogenic fungus, Glomerella cingulata. At the first step, oxidation proceeded at the remote double bond to give (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol and (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,10,11-triol. In the second step, (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol was hydroxylated at the C-5 position and to give (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol. In addition, (2E,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol was isomerized to (2Z,6E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol.

Microbial Oxidation of Citronellol by Glomerella Cingulata

Abstract 3,7-dimethyl-l,6,7-octanetriol was obtained on the microbial transformation of citronellol using plant pathogenic fungus, Glomerella cingulata as a biocatalyst.

Biotransformation of (2Z,6Z)-farnesol by the plant pathogenic fungus Glomerella cingulata

Abstract The microbial transformation of (2 Z ,6 Z )-farnesol was investigated using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst. Oxidation of the remote double bond and isomerization of the 2,3-double bond gave (2 Z ,6 Z )-3,7,11-trimethyl-2,6-dodecadiene-1,10,11-triol and (2 E ,6 Z )-3,7,11-trimethyl-2-6-dodecadiene-1,10,11-triol as major metabolites. One of the further degraded compounds, ( Z )-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one, was also obtained.

Enantioselective Cyclization of (\pm)-Lavandulol to (−)-(2S, 4S)-1,5-Epoxy-5-methyl-2-(1-methylethenyl)-4-hexanol by Glomerella cingulata

Abstract Enantiomerically pure (100% e.e.) (−)-(2S,4S)-1,5-epoxy-5-methyl-2-(1-methylethenyl)-4-hexanol that is a new skeleton monoterpenoid was obtained on the microbial transformation of (\pm)-lavandulol using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst.

Microbial Transformation of (±)-Citronellal by Glomerella Cingulata

Abstract Microbial transformation of citronellal by Glomerella cingulata was investigated. Citronellal was reduced to citronellol which was then transformed to 3,7-dimethyl-1,6,7-octanetriol

Biotransformation of (-)-dihydromyrcenyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst.

The microbial transformation of (-)-dihydromyrcenyl acetate was investigated using the plant parasitic fungus Glomerella cingulata. As a result, (-)-dihydromyrcenyl acetate was converted to dihydromyrcenol, 3,7-dihydroxy-3,7-dimethyl-1-octene-7-carboxylate, 3,7-dihydroxy-3,7-dimethyl-1-octene, 3,7-dimethyloctane-1,2, 7-triol-7-carboxylate, and 3,7-dimethyloctane-1,2,7-triol. In addition, microbial transformation of dihydromyrcenol by G. cingulata was carried out. The metabolic pathway of (-)-dihydromyrcenyl acetate is discussed.