Asymmetric reduction of acetophenone into R-(+)-1-phenylethanol by endophytic fungus Neofusicoccum parvum BYEF07 isolated from Illicium verum.

Seventy-nine strains of endophytic fungi isolated from the healthy leaves, twigs and fruits of Illicium verum were screened for the asymmetric reduction activities to acetophenone. Strain BYEF07, which showed relatively high reduction activities, has been classified as Neofusicoccum parvum, and the main product was confirmed to be (R)-(+)-1-phenylethanol by GC-MS and chiral HPLC methods. The bio-reduction conditions of acetophenone by cells of N. parvum BYEF07 were investigated in detail. Under the conditions of 1.8 g/L of acetophenone, 100 g/L of microorganism cells and 10 g/L of glucose in 40 mL Na2HPO4 KH2PO4 buffer solution at pH7.5, 30 °C and 150 rpm, after 48 h reaction, the production yield of 1-phenylethanol and enantiomeric excess value of (R)-(+)-1-phenylethanol were 78% and 96%, respectively.

Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens.

A variety of volatile phenylpropenes, C6-C3 compounds are widely distributed in the plant kingdom, whereas prenylated phenylpropenes are limited to a few plant species. In this study, we analysed the volatile profiles from Illicium anisatum leaves and identified two O-prenylated phenylpropenes, 4-allyl-2-methoxy-1-[(3-methylbut-2-en-1-yl)oxy]benzene [O-dimethylallyleugenol (9)] and 5-allyl-1,3-dimethoxy-2-(3-methylbut-2-en-1-yl)oxy]benzene [O-dimethylallyl-6-methoxyeugenol (11)] as major constituents. The structure-activity relationship of a series of eugenol derivatives showed that specific phenylpropenes, including eugenol (1), isoeugenol (2) and 6-methoxyeugenol (6), with a phenolic hydroxy group had antifungal activity for a fungal pathogen, whereas guaiacol, a simple phenolic compound, and allylbenzene had no such activity. The eugenol derivatives that exhibited antifungal activity, in turn, had no significant toxicant property for mite oviposition. Interestingly, O-dimethylallyleugenol (9) in which the phenolic oxygen was masked with a dimethylallyl group exhibited a specific, potent oviposition deterrent activity for mites. The sharp contrast in structural requirements of phenylpropenes suggested distinct mechanisms underlying the two biological activities and the importance of a phenolic hydroxy group and its dimethylallylation for the structure-based design of new functional properties of phenylpropenes.