title: Differential patterns of dehydroabietic acid biotransformation by Nicotiana tabacum and Catharanthus roseus cells.
abstract: The aim of this study was to use whole cell catalysts as tools for modification of selected resin acids in order to obtain value-added functional derivatives. The enzymatic bioconversion capacities of two plant species were tested towards dehydroabietic acid. Dehydroabietic acid (DHA) is an abundant resin acid in conifers, representing a natural wood protectant. It is also one of the constituents found in by-products of the kraft chemical pulping industry. DHA was fed to tobacco (Nicotiana tabacum) and Madagascar periwinkle (Catharanthus roseus) plant cell and tissue cultures and bioconversion product formation was monitored using NMR analysis. Both plant species took up DHA from culture medium, and various types of typical detoxification processes occurred in both cultures. In addition, diverse responses to DHA treatment were observed, including differences in uptake kinetics, chemical modification of added substrate and changes in overall metabolism of the cells. Interestingly, Catharanthus roseus, a host species for pharmaceutically valuable terpenoid indole alkaloids, exhibited a very different bioconversion pattern for exogenously applied DHA than tobacco, which does not possess a terpenoid indole pathway. In tobacco, DHA is readily glycosylated in the carbonyl group, whereas in periwinkle it is proposed that a cytochrome P450-catalyzed enzymatic detoxification reaction takes place before the formation of glycosylated product.
authors.affiliation: VTT Technical Research Centre of Finland, 02044-VTT, Finland. suvi.hakkinen@vtt.fi
authors.forename: Suvi T
authors.initials: ST
authors.lastname: Häkkinen
authors.forename: Petri
authors.initials: P
authors.lastname: Lackman
authors.forename: Heli
authors.initials: H
authors.lastname: Nygrén
authors.forename: Kirsi-Marja
authors.initials: KM
authors.lastname: Oksman-Caldentey
authors.forename: Hannu
authors.initials: H
authors.lastname: Maaheimo
authors.forename: Heiko
authors.initials: H
authors.lastname: Rischer
mesh_terms: D045784:Abietanes / Q000737:chemistry / Q000378:metabolism*; D019149:Bioreactors; D001711:Biotransformation; D002384:Catalysis; D030008:Catharanthus / Q000378:metabolism*; D003470:Culture Media; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D006031:Glycosylation; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D046948:Secologanin Tryptamine Alkaloids / Q000378:metabolism; D013045:Species Specificity; D014026:Nicotiana / Q000378:metabolism*
chemical_list: D045784:Abietanes; D003470:Culture Media; D046948:Secologanin Tryptamine Alkaloids; C013913:dehydroabietic acid; D003577:Cytochrome P-450 Enzyme System