Literature DB >> 21518766

The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase (PaLAS) are epimers of a thermally unstable diterpenol.

Christopher I Keeling1, Lina L Madilao, Philipp Zerbe, Harpreet K Dullat, Jörg Bohlmann.   

Abstract

The levopimaradiene/abietadiene synthase from Norway spruce (Picea abies; PaLAS) has previously been reported to produce a mixture of four diterpene hydrocarbons when incubated with geranylgeranyl diphosphate as the substrate: levopimaradiene, abietadiene, neoabietadiene, and palustradiene. However, variability in the assay products observed by GC-MS of this and orthologous conifer diterpene synthases over the past 15 years suggested that these diterpenes may not be the initial enzyme assay products but are rather the products of dehydration of an unstable alcohol. We have identified epimers of the thermally unstable allylic tertiary alcohol 13-hydroxy-8(14)-abietene as the products of PaLAS. The identification of these compounds, not previously described in conifers, as the initial products of PaLAS has considerable implications for our understanding of the complexity of the biosynthetic pathway of the structurally diverse diterpene resin acids of conifer defense.

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Year:  2011        PMID: 21518766      PMCID: PMC3122176          DOI: 10.1074/jbc.M111.245951

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  35 in total

1.  DaliLite workbench for protein structure comparison.

Authors:  L Holm; J Park
Journal:  Bioinformatics       Date:  2000-06       Impact factor: 6.937

2.  Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement.

Authors:  Reuben J Peters; Rodney B Croteau
Journal:  Proc Natl Acad Sci U S A       Date:  2002-01-22       Impact factor: 11.205

3.  Abietadiene synthase catalysis: conserved residues involved in protonation-initiated cyclization of geranylgeranyl diphosphate to (+)-copalyl diphosphate.

Authors:  Reuben J Peters; Rodney B Croteau
Journal:  Biochemistry       Date:  2002-02-12       Impact factor: 3.162

4.  Diterpenoids from Pinus massoniana resin and their cytotoxicity against A431 and A549 cells.

Authors:  Nian-Yun Yang; Li Liu; Wei-Wei Tao; Jin-Ao Duan; Li-Juan Tian
Journal:  Phytochemistry       Date:  2010-07-02       Impact factor: 4.072

5.  Identification of the single amino acid involved in quenching the ent-kauranyl cation by a water molecule in ent-kaurene synthase of Physcomitrella patens.

Authors:  Hiroshi Kawaide; Ken-ichiro Hayashi; Ryo Kawanabe; Yuka Sakigi; Akihiko Matsuo; Masahiro Natsume; Hiroshi Nozaki
Journal:  FEBS J       Date:  2010-12-01       Impact factor: 5.542

6.  Abietadiene synthase from grand fir (Abies grandis): characterization and mechanism of action of the "pseudomature" recombinant enzyme.

Authors:  R J Peters; J E Flory; R Jetter; M M Ravn; H J Lee; R M Coates; R B Croteau
Journal:  Biochemistry       Date:  2000-12-19       Impact factor: 3.162

7.  The variability of sesquiterpenes emitted from two Zea mays cultivars is controlled by allelic variation of two terpene synthase genes encoding stereoselective multiple product enzymes.

Authors:  Tobias G Köllner; Christiane Schnee; Jonathan Gershenzon; Jörg Degenhardt
Journal:  Plant Cell       Date:  2004-04-09       Impact factor: 11.277

8.  CPHmodels-3.0--remote homology modeling using structure-guided sequence profiles.

Authors:  Morten Nielsen; Claus Lundegaard; Ole Lund; Thomas Nordahl Petersen
Journal:  Nucleic Acids Res       Date:  2010-06-11       Impact factor: 16.971

9.  Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis.

Authors:  Mustafa Köksal; Yinghua Jin; Robert M Coates; Rodney Croteau; David W Christianson
Journal:  Nature       Date:  2010-12-15       Impact factor: 49.962

10.  Transcriptome mining, functional characterization, and phylogeny of a large terpene synthase gene family in spruce (Picea spp.).

Authors:  Christopher I Keeling; Sabrina Weisshaar; Steven G Ralph; Sharon Jancsik; Britta Hamberger; Harpreet K Dullat; Jörg Bohlmann
Journal:  BMC Plant Biol       Date:  2011-03-07       Impact factor: 4.215

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  22 in total

Review 1.  Insights into conifer giga-genomes.

Authors:  Amanda R De La Torre; Inanc Birol; Jean Bousquet; Pär K Ingvarsson; Stefan Jansson; Steven J M Jones; Christopher I Keeling; John MacKay; Ove Nilsson; Kermit Ritland; Nathaniel Street; Alvin Yanchuk; Philipp Zerbe; Jörg Bohlmann
Journal:  Plant Physiol       Date:  2014-10-27       Impact factor: 8.340

Review 2.  Plant P450s as versatile drivers for evolution of species-specific chemical diversity.

Authors:  Björn Hamberger; Søren Bak
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2013-01-06       Impact factor: 6.237

3.  A single residue change leads to a hydroxylated product from the class II diterpene cyclization catalyzed by abietadiene synthase.

Authors:  Jared Criswell; Kevin Potter; Freya Shephard; Michael H Beale; Reuben J Peters
Journal:  Org Lett       Date:  2012-11-20       Impact factor: 6.005

4.  Picking sides: distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis.

Authors:  Yisheng Wu; Qiang Wang; Matthew L Hillwig; Reuben J Peters
Journal:  Biochem J       Date:  2013-09-01       Impact factor: 3.857

Review 5.  Terpenoid synthase structures: a so far incomplete view of complex catalysis.

Authors:  Yang Gao; Richard B Honzatko; Reuben J Peters
Journal:  Nat Prod Rep       Date:  2012-08-21       Impact factor: 13.423

6.  Gene discovery of modular diterpene metabolism in nonmodel systems.

Authors:  Philipp Zerbe; Björn Hamberger; Macaire M S Yuen; Angela Chiang; Harpreet K Sandhu; Lina L Madilao; Anh Nguyen; Britta Hamberger; Søren Spanner Bach; Jörg Bohlmann
Journal:  Plant Physiol       Date:  2013-04-23       Impact factor: 8.340

7.  Evolution of conifer diterpene synthases: diterpene resin acid biosynthesis in lodgepole pine and jack pine involves monofunctional and bifunctional diterpene synthases.

Authors:  Dawn E Hall; Philipp Zerbe; Sharon Jancsik; Alfonso Lara Quesada; Harpreet Dullat; Lina L Madilao; Macaire Yuen; Jörg Bohlmann
Journal:  Plant Physiol       Date:  2012-12-12       Impact factor: 8.340

8.  Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals.

Authors:  Ke Zhou; Meimei Xu; Mollie Tiernan; Qian Xie; Tomonobu Toyomasu; Chizu Sugawara; Madoka Oku; Masami Usui; Wataru Mitsuhashi; Makiko Chono; Peter M Chandler; Reuben J Peters
Journal:  Phytochemistry       Date:  2012-09-22       Impact factor: 4.072

9.  Biosynthetic Origin of the Ether Ring in Platensimycin.

Authors:  Jeffrey D Rudolf; Liao-Bin Dong; Karina Manoogian; Ben Shen
Journal:  J Am Chem Soc       Date:  2016-12-14       Impact factor: 15.419

10.  Modularity of Conifer Diterpene Resin Acid Biosynthesis: P450 Enzymes of Different CYP720B Clades Use Alternative Substrates and Converge on the Same Products.

Authors:  Katrin Geisler; Niels Berg Jensen; Macaire M S Yuen; Lina Madilao; Jörg Bohlmann
Journal:  Plant Physiol       Date:  2016-03-02       Impact factor: 8.340

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