Transformation of alpha-pinene using Picea abies suspension culture.
alpha-Pinene, both as the pure enantiomers and as the racemate, was transformed mainly to trans-verbenol by treatment with a Picea abies suspension cell culture. These reactions were followed by a slow transformation of the verbenol to verbenone, which was not transformed further. trans-Pinocarveol, myrtenol, cis-verbenol, and alpha-terpineol were byproducts of intermediate abundance. When subjected to the action of the suspension culture, cis-verbenol was not only transformed to verbenone but also isomerized to trans-verbenol. The transformation of alpha-pinene was fast, and the products were detected within one minute. The absolute configuration of the major products corresponded to that of the starting alpha-pinene enantiomer.
Lindmark-Henriksson
Marica
M
Department of Natural and Environmental Sciences, Chemistry, Mid Sweden University, SE-851 70 Sundsvall, Sweden.
Isaksson
Dan
D
Sjödin
Kristina
K
Högberg
Hans-Erik
HE
Vanek
Tomás
T
Valterová
Irena
I
D000081008:Bicyclic Monoterpenes; D001711:Biotransformation; D002478:Cells, Cultured; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D039821:Monoterpenes / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D028222:Picea / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000378:metabolism; D014867:Water
D000081008:Bicyclic Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; D014867:Water; C052875:verbenone; C009951:verbenol; C005451:alpha-pinene