Literature DB >> 33625237

Early and Late Steps of Quinine Biosynthesis.

Francesco Trenti1, Kotaro Yamamoto1, Benke Hong1, Christian Paetz1, Yoko Nakamura1, Sarah E O'Connor1.   

Abstract

The enzymatic basis for quinine 1 biosynthesis was investigated. Transcriptomic data from the producing plant led to the discovery of three enzymes involved in the early and late steps of the pathway. A medium-chain alcohol dehydrogenase (CpDCS) and an esterase (CpDCE) yielded the biosynthetic intermediate dihydrocorynantheal 2 from strictosidine aglycone 3. Additionally, the discovery of an O-methyltransferase specific for 6'-hydroxycinchoninone 4 suggested the final step order to be cinchoninone 16/17 hydroxylation, methylation, and keto-reduction.

Entities:  

Year:  2021        PMID: 33625237      PMCID: PMC7944568          DOI: 10.1021/acs.orglett.1c00206

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  14 in total

1.  A Local-Desymmetrization-Based Divergent Synthesis of Quinine and Quinidine.

Authors:  Jaehoo Lee; David Y-K Chen
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-06       Impact factor: 15.336

2.  Rabe rest in peace: confirmation of the rabe-kindler conversion of D-quinotoxine into quinine: experimental affirmation of the Woodward-Doering formal total synthesis of quinine.

Authors:  Aaron C Smith; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase.

Authors:  G Schröder; E Unterbusch; M Kaltenbach; J Schmidt; D Strack; V De Luca; J Schröder
Journal:  FEBS Lett       Date:  1999-09-17       Impact factor: 4.124

4.  The gene encoding polyneuridine aldehyde esterase of monoterpenoid indole alkaloid biosynthesis in plants is an ortholog of the alpha/betahydrolase super family.

Authors:  E Dogru; H Warzecha; F Seibel; S Haebel; F Lottspeich; J Stöckigt
Journal:  Eur J Biochem       Date:  2000-03

5.  Application of carborundum abrasion for investigating the leaf epidermis: molecular cloning of Catharanthus roseus 16-hydroxytabersonine-16-O-methyltransferase.

Authors:  Dylan Levac; Jun Murata; Won S Kim; Vincenzo De Luca
Journal:  Plant J       Date:  2007-12-05       Impact factor: 6.417

6.  Strictosidine activation in Apocynaceae: towards a "nuclear time bomb"?

Authors:  Grégory Guirimand; Vincent Courdavault; Arnaud Lanoue; Samira Mahroug; Anthony Guihur; Nathalie Blanc; Nathalie Giglioli-Guivarc'h; Benoit St-Pierre; Vincent Burlat
Journal:  BMC Plant Biol       Date:  2010-08-19       Impact factor: 4.215

Review 7.  Quinine, an old anti-malarial drug in a modern world: role in the treatment of malaria.

Authors:  Jane Achan; Ambrose O Talisuna; Annette Erhart; Adoke Yeka; James K Tibenderana; Frederick N Baliraine; Philip J Rosenthal; Umberto D'Alessandro
Journal:  Malar J       Date:  2011-05-24       Impact factor: 2.979

Review 8.  The Fever Tree: from Malaria to Neurological Diseases.

Authors:  Sara Eyal
Journal:  Toxins (Basel)       Date:  2018-11-23       Impact factor: 4.546

9.  Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle.

Authors:  Lorenzo Caputi; Jakob Franke; Scott C Farrow; Khoa Chung; Richard M E Payne; Trinh-Don Nguyen; Thu-Thuy T Dang; Inês Soares Teto Carqueijeiro; Konstantinos Koudounas; Thomas Dugé de Bernonville; Belinda Ameyaw; D Marc Jones; Ivo Jose Curcino Vieira; Vincent Courdavault; Sarah E O'Connor
Journal:  Science       Date:  2018-05-03       Impact factor: 63.714

10.  C-H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity.

Authors:  Daniel H O' Donovan; Paul Aillard; Martin Berger; Aurélien de la Torre; Desislava Petkova; Christian Knittl-Frank; Danny Geerdink; Marcel Kaiser; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-22       Impact factor: 16.823

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  4 in total

1.  Antimalarial Natural Products.

Authors:  David G I Kingston; Maria Belen Cassera
Journal:  Prog Chem Org Nat Prod       Date:  2022

2.  Multifunctional biocatalyst for conjugate reduction and reductive amination.

Authors:  Thomas W Thorpe; James R Marshall; Vanessa Harawa; Rebecca E Ruscoe; Anibal Cuetos; James D Finnigan; Antonio Angelastro; Rachel S Heath; Fabio Parmeggiani; Simon J Charnock; Roger M Howard; Rajesh Kumar; David S B Daniels; Gideon Grogan; Nicholas J Turner
Journal:  Nature       Date:  2022-04-06       Impact factor: 49.962

Review 3.  Biosynthesis and synthetic biology of psychoactive natural products.

Authors:  Cooper S Jamieson; Joshua Misa; Yi Tang; John M Billingsley
Journal:  Chem Soc Rev       Date:  2021-06-21       Impact factor: 60.615

4.  Reconstitution of monoterpene indole alkaloid biosynthesis in genome engineered Nicotiana benthamiana.

Authors:  Quentin M Dudley; Seohyun Jo; Delia Ayled Serna Guerrero; Monika Chhetry; Mark A Smedley; Wendy A Harwood; Nathaniel H Sherden; Sarah E O'Connor; Lorenzo Caputi; Nicola J Patron
Journal:  Commun Biol       Date:  2022-09-10
  4 in total

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