TY - JOUR

T1 - Oxyfunctionalization of ɑ- and β-Pinene by Selected Basidiomycetes

AU - Busmann, Dagmar

AU - Berger, Ralf Günter

N1 - Funding information: This work was supported in part by the DFG (Deutsche Forschungsgemeinschaft) via the Graduiertenkolleg “Naturstofftransformation”.

PY - 1994/10

Y1 - 1994/10

N2 - Several strains of basidiomycetes were examined for their ability to transform ɑ- and (ß-pinene in agitated submerged, cultures. Four major metabolites of ß-pinene (verbenol, verbenone, myrtenol, and trans-pinocarveol) and three main metabolites of (ß-pinene (1,4-cineol, myrtenol, and trans-pinocarveol) were isolated from the fermentation, broth. The metabolic pathways included allylic oxidation, oxidative cleavage and further regioselective, oxidation. Ganoderma applanatum was found to carry out the stereoselective allylic hydroxylation of ß-pinene to verbenol, and of (ß-pinene to trans-pinocarveol in trans position to the C-C, bridge. The optimal conditions of the bioreaction were established with respect to substrate concentration, incubation time and conversion, time. Due to growth inhibition caused by elevated substrate concentration, the bioconversion of (ß-pinene required pre-grown, cultures. Generally, mycelial pellet cultures were supplemented with the terpene substrate when a residual glucose content of 50% was, reached. Depending on strain this point was reached after about 48 h. An incubation period of two to three days gave best, yields. The transient accumulation of oxygenated products apparently reflected different reaction velocities of the successive catabolic, steps.

AB - Several strains of basidiomycetes were examined for their ability to transform ɑ- and (ß-pinene in agitated submerged, cultures. Four major metabolites of ß-pinene (verbenol, verbenone, myrtenol, and trans-pinocarveol) and three main metabolites of (ß-pinene (1,4-cineol, myrtenol, and trans-pinocarveol) were isolated from the fermentation, broth. The metabolic pathways included allylic oxidation, oxidative cleavage and further regioselective, oxidation. Ganoderma applanatum was found to carry out the stereoselective allylic hydroxylation of ß-pinene to verbenol, and of (ß-pinene to trans-pinocarveol in trans position to the C-C, bridge. The optimal conditions of the bioreaction were established with respect to substrate concentration, incubation time and conversion, time. Due to growth inhibition caused by elevated substrate concentration, the bioconversion of (ß-pinene required pre-grown, cultures. Generally, mycelial pellet cultures were supplemented with the terpene substrate when a residual glucose content of 50% was, reached. Depending on strain this point was reached after about 48 h. An incubation period of two to three days gave best, yields. The transient accumulation of oxygenated products apparently reflected different reaction velocities of the successive catabolic, steps.

KW - Basidiomycetes

KW - Bioconversion

KW - Cineol

KW - Pinene

KW - Transformation

UR - http://www.scopus.com/inward/record.url?scp=0028152168&partnerID=8YFLogxK

U2 - 10.1515/znc-1994-9-1003

DO - 10.1515/znc-1994-9-1003

M3 - Article

AN - SCOPUS:0028152168

VL - 49

SP - 545

EP - 552

JO - Zeitschrift fur Naturforschung - Section C Journal of Biosciences

JF - Zeitschrift fur Naturforschung - Section C Journal of Biosciences

SN - 0939-5075

IS - 9-10

ER -