Journal of Biotechnology 107 (2004) 173–184 Transformation of terpenes using a Picea abies suspension culture Marica Lindmark-Henriksson a , Dan Isaksson a , Tomáš Vanˇ ek b , Irena Valterová b,1 , Hans-Erik Högberg a , Kristina Sjödin a,∗ a Department of Natural and Environmental Sciences, Chemistry, Mid Sweden University, SE-851 70 Sundsvall, Sweden b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-166 10 Prague, Czech Republic Received 30 May 2003; received in revised form 10 October 2003; accepted 20 October 2003 Abstract When subjected to a Picea abies suspension cell culture, -pinene, either one of the pure enantiomers or the racemate, was transformed mainly to trans-pinocarveol along with the minor products myrtenol, -terpineol, pinocarvone, myrtenal and cis-pinocarveol. The absolute configuration of the major products corresponded to that of the starting -pinene enantiomer. Some of the primary transformation products, i.e. (1S)-cis- and (1S)-trans-pinocarveol, (1R)-myrtenol and (4S)--terpineol, were also tested as substrates of the P. abies suspension culture. They reacted more slowly than -pinene but, except for (4S)--terpineol, they were all transformed. Thus, (1R)-myrtenol was converted into both (1R)-myrtenal and (1R)-myrtanol, whereas (1S)-trans-pinocarveol was converted into (1S)-pinocarvone. (4R)-Limonene was slowly transformed by the suspension culture into limonene-(1,2)-epoxide as the major product, with carveol, perillyl alcohol and 1,8-cineole as minor products. Autoxidation of terpenes in cell-free nutrient medium was investigated in detail. -Pinene and -pinene were both autoxidized to a certain extent, while limonene remained unaffected. The rate of the autoxidation was more than one order of magnitude slower than that of the biotransformation. Moreover, different products were formed by autoxidation than by biotransformation. © 2003 Elsevier B.V. All rights reserved. Keywords: Biotransformation; Allylic oxidation; Autoxidation; -Pinene; Limonene; Terpene alcohol 1. Introduction -Pinene, -pinene and limonene are the main monoterpenes of Norway spruce, Picea abies (Persson ∗ Corresponding author. Tel.: +46-(0)60-148891; fax: +46-(0)60-148802. E-mail addresses: irena@uochb.cas.cz (I. Valterov´ a), kristina.sjodin@mh.se (K. Sjödin). 1 Co-corresponding author. Tel. +420-220-183298; fax: 420-220-183582. et al., 1996). Norway spruce wood is the raw mate- rial of the thermomechanical pulping (TMP) process, and the steam distillate recovered from this process, the TMP-turpentine, has the same major monoter- pene constituents as the wood (Lindmark et al., 1998). To increase the commercial value of the TMP- turpentine, it would be of interest to be able to convert its major monoterpene hydrocarbon constituents into more valuable compounds, such as oxygenated ones. Using plant cells could be a mild and potentially 0168-1656/$ – see front matter © 2003 Elsevier B.V. All rights reserved. doi:10.1016/j.jbiotec.2003.10.009