Differential patterns of dehydroabietic acid biotransformation by Nicotiana tabacum and Catharanthus roseus cells

Suvi T. Häkkinen (Corresponding Author), Petri Lackman, Heli Nygren, Kirsi-Marja Oksman-Caldentey, Hannu Maaheimo, Heiko Rischer

Research output: Contribution to journalArticleScientificpeer-review

10 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)287-294
Number of pages8
JournalJournal of Biotechnology
Volume157
Issue number2
DOIs
Publication statusPublished - 2012
MoE publication typeA1 Journal article-refereed

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Catharanthus
Biotransformation
Tobacco
Acids
Bioconversion
Detoxification
Plant cell culture
Resins
Secologanin Tryptamine Alkaloids
Vinca
Coniferophyta
Chemical Industry
Tissue culture
Terpenes
Chemical modification
Plant Cells
dehydroabietic acid
Alkaloids
Metabolism
Cytochrome P-450 Enzyme System

Keywords

  • Biotransformation
  • Nicotiana tabacum
  • Catharanthus roseus
  • Dehydroabietic acid
  • Cell cultures
  • Hairy roots

Cite this

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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.",
keywords = "Biotransformation, Nicotiana tabacum, Catharanthus roseus, Dehydroabietic acid, Cell cultures, Hairy roots",
author = "H{\"a}kkinen, {Suvi T.} and Petri Lackman and Heli Nygren and Kirsi-Marja Oksman-Caldentey and Hannu Maaheimo and Heiko Rischer",
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language = "English",
volume = "157",
pages = "287--294",
journal = "Journal of Biotechnology",
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}

Differential patterns of dehydroabietic acid biotransformation by Nicotiana tabacum and Catharanthus roseus cells. / Häkkinen, Suvi T. (Corresponding Author); Lackman, Petri; Nygren, Heli; Oksman-Caldentey, Kirsi-Marja; Maaheimo, Hannu; Rischer, Heiko.

In: Journal of Biotechnology, Vol. 157, No. 2, 2012, p. 287-294.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Differential patterns of dehydroabietic acid biotransformation by Nicotiana tabacum and Catharanthus roseus cells

AU - Häkkinen, Suvi T.

AU - Lackman, Petri

AU - Nygren, Heli

AU - Oksman-Caldentey, Kirsi-Marja

AU - Maaheimo, Hannu

AU - Rischer, Heiko

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

KW - Biotransformation

KW - Nicotiana tabacum

KW - Catharanthus roseus

KW - Dehydroabietic acid

KW - Cell cultures

KW - Hairy roots

U2 - 10.1016/j.jbiotec.2011.11.008

DO - 10.1016/j.jbiotec.2011.11.008

M3 - Article

VL - 157

SP - 287

EP - 294

JO - Journal of Biotechnology

JF - Journal of Biotechnology

SN - 0168-1656

IS - 2

ER -