The functional divergence of short-chain dehydrogenases involved in tropinone reduction.
@article{Brock2008TheFD, title={The functional divergence of short-chain dehydrogenases involved in tropinone reduction.}, author={Andrea Brock and Wolfgang Brandt and Birgit Dr{\"a}ger}, journal={The Plant journal : for cell and molecular biology}, year={2008}, volume={54 3}, pages={ 388-401 } }
Tropane alkaloids typically occur in the Solanaceae and are also found in Cochlearia officinalis, a member of the Brassicaceae. Tropinone reductases are key enzymes of tropane alkaloid metabolism. Two different tropinone reductases form one stereoisomeric product each, either tropine for esterified alkaloids or pseudotropine that is converted to calystegines. A cDNA sequence with similarity to known tropinone reductases (TR) was cloned from C. officinalis. The protein was expressed in…
Figures and Tables from this paper
25 Citations
Molecular cloning and catalytic characterization of a recombinant tropine biosynthetic tropinone reductase from Withania coagulans leaf.
- Biology, ChemistryGene
- 2013
Tropine Forming Tropinone Reductase Gene from Withania somnifera (Ashwagandha): Biochemical Characteristics of the Recombinant Enzyme and Novel Physiological Overtones of Tissue-Wide Gene Expression Patterns
- Biology, ChemistryPloS one
- 2013
The data suggest that, in W. somnifera, aerial tissues as well possess tropane alkaloid biosynthetic competence, a conceptual novelty in the backdrop of classical view that these tissues acquire the alkaloids through transportation from roots rather than synthesis.
Substrate flexibility and reaction specificity of tropinone reductase-like short-chain dehydrogenases.
- Biology, ChemistryBioorganic chemistry
- 2014
Enhancing Tropane Alkaloid Production Based on the Functional Identification of Tropine-Forming Reductase in Scopolia lurida, a Tibetan Medicinal Plant
- Biology, ChemistryFront. Plant Sci.
- 2017
The isolation and characterization of a putative short chain dehydrogenase (SDR) gene, SlTRI, provides a candidate gene for enhancing tropane alkaloid biosynthesis in S. lurida via metabolic engineering and provides a better understanding of tropan alkaloids biosynthesis.
Functional characterization of a novel tropinone reductase-like gene in Dendrobium nobile Lindl.
- BiologyJournal of plant physiology
- 2013
Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids.
- Biology, ChemistryPhytochemistry
- 2016
Molecular cloning and characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloid production in AaTRI‐transformed hairy roots
- BiologyBiotechnology and applied biochemistry
- 2009
Cl cloning and characterization of two fulllength cDNAs encoding TRI and TRII from the solanaceous plant Anisodus acutangulus by rapid amplification of cDNA ends show that AaTRI is a promising target for genetic engineering to increase tropane alkaloid in A. acUTangulus.
Molecular cloning and characterization of a tropinone reductase from Dendrobium nobile Lindl
- BiologyMolecular Biology Reports
- 2012
Catalytic activity assay with recombinant protein demonstrated that DnTR1 was able to reduce tropinone, 3-quinuclidinone hydrochloride, and 4-methylcyclohexanone using NADPH as coenzyme, indicating that DNTR1 regulation may be involved in a jasmonate-dependent pathway.
Identification of a Noroxomaritidine Reductase with Amaryllidaceae Alkaloid Biosynthesis Related Activities*
- Chemistry, BiologyThe Journal of Biological Chemistry
- 2016
A short chain alcohol dehydrogenase/reductase that co-expresses with the previously discovered norbelladine 4′-O-methyltransferase is cloned and expressed in Escherichia coli and indicates that it functions as a noroxomaritidine reductase that forms oxomarItinamine from norxomar itidine through a carbon-carbon double bond reduction.
References
SHOWING 1-10 OF 65 REFERENCES
Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.
- Biology, ChemistryPhytochemistry
- 2006
Two Tropinone Reductases with Distinct Stereospecificities from Cultured Roots of Hyoscyamus niger.
- Chemistry, BiologyPlant physiology
- 1992
Two stereospecifically distinct NADPH-dependent oxidoreductases, TR-I and TR-II, which reduce tropinone to 3alpha-hydroxytropane (tropine) and 3beta-Hydroxytropine (psi-tropine), were detected mainly in the root of tropane alkaloid-producing plants but not in nonproducing cultured root.
Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor.
- Biology, ChemistryProceedings of the National Academy of Sciences of the United States of America
- 1993
How the two TRs may have evolved to catalyze the opposite stereospecific reductions is discussed, with significant similarities with enzymes in the short-chain, nonmetal dehydrogenase family.
The reduction of tropinone in Datura stramonium root cultures by two specific reductases.
- Biology, ChemistryPhytochemistry
- 1994
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.)
- Biology, ChemistryPlant Molecular Biology
- 2004
The distribution of the TRII transcript in comparison with the calystegine concentrations in the tissues suggests transport of calyStegines or their precursors between potato organs.
Crystal structures of two tropinone reductases: different reaction stereospecificities in the same protein fold.
- Chemistry, BiologyProceedings of the National Academy of Sciences of the United States of America
- 1998
The results obtained herein raise the possibility that in certain cases different stereospecificities can be acquired in enzymes by changing a few amino acid residues within substrate binding sites.
Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts
- BiologyPlanta
- 2006
Two cDNAs coding for TRs were isolated from potato (Solanum tuberosum L.) tuber sprouts and expressed in E. coli, showing kinetic properties typical for tropine-forming tropinone reductases (TRI) involved in hyoscyamine formation and the pseudotropine-forms tropin one reductase was detected in potato roots, stolons, and tuber sprout.
Crystal structure of vestitone reductase from alfalfa (Medicago sativa L.).
- Chemistry, BiologyJournal of molecular biology
- 2007
Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis.
- Chemistry, BiologyThe Plant journal : for cell and molecular biology
- 2006
One of these cDNAs, exhibiting an expression pattern very similar to previously isolated c DNAs coding for enzymes in benzylisoquinoline biosynthesis, showed the highest amino acid identity to reductases in menthol biosynthesis and was identified as salutaridine reductase (SalR).
Insight into the molecular evolution of two tropinone reductases.
- Biology, ChemistryBioscience, biotechnology, and biochemistry
- 1999
This work has shown that highly homologous proteins with variable substrate-binding residues have also been found in tropane alkaloid non-producing species, demonstrating a simple evolutionary process that plants have taken to acquire a new secondary metabolic pathway.