Literature DB >> 20228795

Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy.

Jillian M Hagel1, Peter J Facchini.   

Abstract

Two previously undetected enzymes involved in morphine biosynthesis and unique among plants to opium poppy have been identified as non-heme dioxygenases, in contrast to the functionally analogous cytochrome P450s found in mammals. We used functional genomics to isolate thebaine 6-O-demethylase (T6ODM) and codeine O-demethylase (CODM), the only known 2-oxoglutarate/Fe(II)-dependent dioxygenases that catalyze O-demethylation. Virus-induced gene silencing of T6ODM and CODM in opium poppy efficiently blocked metabolism at thebaine and codeine, respectively.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20228795     DOI： 10.1038/nchembio.317

Source DB:  PubMed          Journal:  Nat Chem Biol        ISSN： 1552-4450            Impact factor:   15.040


  22 in total

1.  Analgesia: morphine-pathway block in top1 poppies.

Authors:  Anthony G Millgate; Barry J Pogson; Iain W Wilson; Toni M Kutchan; Meinhart H Zenk; Wayne L Gerlach; Anthony J Fist; Philip J Larkin
Journal:  Nature       Date:  2004-09-23       Impact factor: 49.962

2.  Oripavine - a new opium alkaloid.

Authors:  B Nielsen; J Röe; E Brochmann-Hanssen
Journal:  Planta Med       Date:  1983-08       Impact factor: 3.352

3.  CYP2D6: a key enzyme in morphine synthesis in animals.

Authors:  Wei Zhu
Journal:  Med Sci Monit       Date:  2008-11

4.  Mammalian cytochrome P450 enzymes catalyze the phenol-coupling step in endogenous morphine biosynthesis.

Authors:  Nadja Grobe; Baichen Zhang; Ursula Fisinger; Toni M Kutchan; Meinhart H Zenk; F Peter Guengerich
Journal:  J Biol Chem       Date:  2009-06-26       Impact factor: 5.157

5.  In vivo formation of codeinone and morphinone from codeine. Isolation and identification from guinea pig bile.

Authors:  T Ishida; M Yano; S Toki
Journal:  Drug Metab Dispos       Date:  1991 Sep-Oct       Impact factor: 3.922

6.  Reductive and oxidative half-reactions of morphinone reductase from Pseudomonas putida M10: a kinetic and thermodynamic analysis.

Authors:  D H Craig; P C Moody; N C Bruce; N S Scrutton
Journal:  Biochemistry       Date:  1998-05-19       Impact factor: 3.162

7.  Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum.

Authors:  B Unterlinner; R Lenz; T M Kutchan
Journal:  Plant J       Date:  1999-06       Impact factor: 6.417

8.  A fluorimetric assay for hydrogen peroxide, suitable for NAD(P)H-dependent superoxide generating redox systems.

Authors:  R Rapoport; I Hanukoglu; D Sklan
Journal:  Anal Biochem       Date:  1994-05-01       Impact factor: 3.365

9.  Quantitative 1H nuclear magnetic resonance metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in opium poppy.

Authors:  Jillian M Hagel; Aalim M Weljie; Hans J Vogel; Peter J Facchini
Journal:  Plant Physiol       Date:  2008-06-11       Impact factor: 8.340

Review 10.  Structural studies on 2-oxoglutarate oxygenases and related double-stranded beta-helix fold proteins.

Authors:  Ian J Clifton; Michael A McDonough; Dominic Ehrismann; Nadia J Kershaw; Nicolas Granatino; Christopher J Schofield
Journal:  J Inorg Biochem       Date:  2006-03-02       Impact factor: 4.155
View more
  66 in total

1.  Tyrosine aminotransferase contributes to benzylisoquinoline alkaloid biosynthesis in opium poppy.

Authors:  Eun-Jeong Lee; Peter J Facchini
Journal:  Plant Physiol       Date:  2011-09-23       Impact factor: 8.340

2.  Biosynthesis: unmasking morphine.

Authors:  Eric J Dimise; Steven D Bruner
Journal:  Nat Chem Biol       Date:  2010-04       Impact factor: 15.040

3.  Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum.

Authors:  Limei Chang; Jillian M Hagel; Peter J Facchini
Journal:  Plant Physiol       Date:  2015-08-21       Impact factor: 8.340

4.  Norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family.

Authors:  Eun-Jeong Lee; Peter Facchini
Journal:  Plant Cell       Date:  2010-10-29       Impact factor: 11.277

5.  Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy.

Authors:  Thu-Thuy T Dang; Peter J Facchini
Journal:  Plant Physiol       Date:  2012-04-25       Impact factor: 8.340

6.  Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy.

Authors:  Jeremy S Morris; Peter J Facchini
Journal:  J Biol Chem       Date:  2016-09-15       Impact factor: 5.157

7.  Cytochrome P450 3A Enzymes Catalyze the O6-Demethylation of Thebaine, a Key Step in Endogenous Mammalian Morphine Biosynthesis.

Authors:  Valerie M Kramlinger; Mónica Alvarado Rojas; Tatsuyuki Kanamori; F Peter Guengerich
Journal:  J Biol Chem       Date:  2015-07-08       Impact factor: 5.157

Review 8.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

Review 9.  Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.

Authors:  F Peter Guengerich; Francis K Yoshimoto
Journal:  Chem Rev       Date:  2018-06-22       Impact factor: 60.622

10.  CYP82Y1 is N-methylcanadine 1-hydroxylase, a key noscapine biosynthetic enzyme in opium poppy.

Authors:  Thu-Thuy T Dang; Peter J Facchini
Journal:  J Biol Chem       Date:  2013-12-09       Impact factor: 5.157
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.