Short communication
Free Access

A chicory cytochrome P450 mono‐oxygenase CYP71AV8 for the oxidation of (+)‐valencene

Katarina Cankar

Laboratory of Plant Physiology, Wageningen University and Research Centre, 6708PB Wageningen, The Netherlands

Plant Research International, Wageningen University and Research Centre, 6708PB Wageningen, The Netherlands

Search for more papers by this author
Adèle van Houwelingen

Plant Research International, Wageningen University and Research Centre, 6708PB Wageningen, The Netherlands

Search for more papers by this author
Dirk Bosch

Plant Research International, Wageningen University and Research Centre, 6708PB Wageningen, The Netherlands

Search for more papers by this author
Theo Sonke

Isobionics, Urmonderbaan 22, 6167RD Geleen, The Netherlands

Search for more papers by this author
Harro Bouwmeester

Laboratory of Plant Physiology, Wageningen University and Research Centre, 6708PB Wageningen, The Netherlands

Search for more papers by this author
Jules Beekwilder

Corresponding Author

E-mail address:jules.beekwilder@wur.nl

Laboratory of Plant Physiology, Wageningen University and Research Centre, 6708PB Wageningen, The Netherlands

Plant Research International, Wageningen University and Research Centre, 6708PB Wageningen, The Netherlands

Corresponding author at: Plant Research International, PO Box 619, 6708PD Wageningen, The Netherlands. Fax: +31 317 418094.
Search for more papers by this author
First published: 26 November 2010
Cited by: 41

Abstract

Chicory (Cichorium intybus L.), which is known to have a variety of terpene‐hydroxylating activities, was screened for a P450 mono‐oxygenase to convert (+)‐valencene to (+)‐nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co‐expression of the enzyme with a valencene synthase in yeast, led to formation of trans‐nootkatol, cis‐nootkatol and (+)‐nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra‐1(10),4,11(13)‐trien‐12‐oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha‐4,11‐diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio‐specificity on (+)‐valencene compared to germacrene A and amorpha‐4,11‐diene.

Number of times cited: 41

  • , Cytochrome P450 (cyp), Encyclopedia of Signaling Molecules, 10.1007/978-3-319-67199-4_101615, (1288-1305), (2017).
  • , Synthetic genome engineering forging new frontiers for wine yeast, Critical Reviews in Biotechnology, 10.1080/07388551.2016.1214945, 37, 1, (112-136), (2016).
  • , Improvement of a P450-Based Recombinant Escherichia coli Whole-Cell System for the Production of Oxygenated Sesquiterpene Derivatives , Journal of Agricultural and Food Chemistry, 10.1021/acs.jafc.7b00792, 65, 19, (3891-3899), (2017).
  • , Microbial Production of Isoprenoids, Consequences of Microbial Interactions with Hydrocarbons, Oils, and Lipids: Production of Fuels and Chemicals, 10.1007/978-3-319-31421-1_219-1, (1-24), (2017).
  • , Microbial Production of Isoprenoids, Consequences of Microbial Interactions with Hydrocarbons, Oils, and Lipids: Production of Fuels and Chemicals, 10.1007/978-3-319-31421-1_219-2, (1-24), (2017).
  • , P450s controlling metabolic bifurcations in plant terpene specialized metabolism, Phytochemistry Reviews, (2017).
  • , Two key polymorphisms in a newly discovered allele of theVitis vinifera TPS24gene are responsible for the production of the rotundone precursor α-guaiene, Journal of Experimental Botany, 67, 3, (799), (2016).
  • , Insights into the Sesquiterpenoid Pathway by Metabolic Profiling and De novo Transcriptome Assembly of Stem-Chicory (Cichorium intybus Cultigroup “Catalogna”), Frontiers in Plant Science, 7, (2016).
  • , Sesquiterpene lactone engineering in microbial and plant platforms: parthenolide and artemisinin as case studies, Applied Microbiology and Biotechnology, 100, 3, (1041), (2016).
  • , Cytochrome P450 CYP71BE5 in grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound (−)-rotundone, Journal of Experimental Botany, 67, 3, (787), (2016).
  • , One-Pot Synthesis of (+)-Nootkatone via Dark Singlet Oxygenation of Valencene: The Triple Role of the Amphiphilic Molybdate Catalyst, Catalysts, 6, 12, (184), (2016).
  • , Cytochrome P450 (cyp), Encyclopedia of Signaling Molecules, 10.1007/978-1-4614-6438-9_101615-1, (1-18), (2017).
  • , Capturing of the monoterpene olefin limonene produced in Saccharomyces cerevisiae, Yeast, 32, 1, (159-171), (2014).
  • , Selective Enzymatic Synthesis of the Grapefruit Flavor (+)‐Nootkatone, ChemCatChem, 7, 4, (601-604), (2015).
  • , Over‐expression of ICE2 stabilizes cytochrome P450 reductase in Saccharomyces cerevisiae and Pichia pastoris, Biotechnology Journal, 10, 4, (623-635), (2015).
  • , Cytochrome P450-enzymes involved in the biosynthesis of mono- and sesquiterpenes, Phytochemistry Reviews, 10.1007/s11101-013-9280-x, 14, 1, (7-24), (2013).
  • , Mechanistic Studies on the Autoxidation of α-Guaiene: Structural Diversity of the Sesquiterpenoid Downstream Products, Journal of Natural Products, 78, 1, (131), (2015).
  • , Accumulation of cynaropicrin in globe artichoke and localization of enzymes involved in its biosynthesis, Plant Science, 239, (128), (2015).
  • , Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis), FEBS Letters, 588, 6, (1001-1007), (2014).
  • , Valencene synthase from the heartwood of Nootka cypress (allitropsis nootkatensis) for biotechnological production of valencene, Plant Biotechnology Journal, 12, 2, (174-182), (2013).
  • , Development of bio-based fine chemical production through synthetic bioengineering, Microbial Cell Factories, 10.1186/s12934-014-0173-5, 13, 1, (2014).
  • , Elucidation and in planta reconstitution of the parthenolide biosynthetic pathway, Metabolic Engineering, 23, (145), (2014).
  • , Production of the Pepper Aroma Compound, (−)-Rotundone, by Aerial Oxidation of α-Guaiene, Journal of Agricultural and Food Chemistry, 62, 44, (10809), (2014).
  • , Cytochrome P450s from Cynara cardunculus L. CYP71AV9 and CYP71BL5, catalyze distinct hydroxylations in the sesquiterpene lactone biosynthetic pathway, Plant Science, 10.1016/j.plantsci.2014.03.007, 223, (59-68), (2014).
  • , Production of the sesquiterpenoid (+)-nootkatone by metabolic engineering of Pichia pastoris, Metabolic Engineering, 10.1016/j.ymben.2014.04.001, 24, (18-29), (2014).
  • , Rice cytochrome P450 MAX1 homologs catalyze distinct steps in strigolactone biosynthesis, Nature Chemical Biology, 10, 12, (1028), (2014).
  • , Production of (+)-valencene in the mushroom-forming fungus S. commune, Applied Microbiology and Biotechnology, 98, 11, (5059), (2014).
  • , Comparative functional analysis of CYP71AV1 natural variants reveals an important residue for the successive oxidation of amorpha‐4,11‐diene, FEBS Letters, 587, 3, (278-284), (2012).
  • , Artemisinic acid: A promising molecule potentially suitable for the semi-synthesis of artemisinin, RSC Advances, 10.1039/c3ra40525g, 3, 21, (7622), (2013).
  • , Yeast metabolic engineering – Targeting sterol metabolism and terpenoid formation, Progress in Lipid Research, 10.1016/j.plipres.2013.03.001, 52, 3, (277-293), (2013).
  • , Biosynthesis of Sesquiterpene Lactones in Pyrethrum (Tanacetum cinerariifolium), PLoS ONE, 8, 5, (e65030), (2013).
  • , An Effective Strategy for Exploring Unknown Metabolic Pathways by Genome Mining, Journal of the American Chemical Society, 135, 15, (5885), (2013).
  • , Challenges and pitfalls of P450-dependent (+)-valencene bioconversion by Saccharomyces cerevisiae, Metabolic Engineering, 18, (25), (2013).
  • , CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase, Applied Microbiology and Biotechnology, 10.1007/s00253-011-3727-z, 95, 1, (123-133), (2012).
  • , Natural sesquiterpenoids, Natural Product Reports, 10.1039/c2np20074k, 29, 11, (1334), (2012).
  • , Isopentenyl diphosphate isomerase: A checkpoint to isoprenoid biosynthesis, Biochimie, 10.1016/j.biochi.2012.03.021, 94, 8, (1621-1634), (2012).
  • , A short‐chain dehydrogenase involved in terpene metabolism from Zingiber zerumbet, The FEBS Journal, 278, 16, (2892-2900), (2011).
  • , Industrial biotechnology—the future of green chemistry?, Green Chemistry, 10.1039/c1gc15579b, 13, 11, (3007), (2011).
  • , Reconstitution of the Costunolide Biosynthetic Pathway in Yeast and Nicotiana benthamiana, PLoS ONE, 6, 8, (e23255), (2011).
  • , Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.), Phytochemistry, 72, 14-15, (1739), (2011).
  • , Microbial Cell Factories for the Production of Terpenoid Flavor and Fragrance Compounds, Journal of Agricultural and Food Chemistry, 10.1021/acs.jafc.7b00473, (2017).