Literature DB >> 17157336

Administering cultured Taxus cells with early precursors reveals bifurcations in the taxoid biosynthetic pathway.

Raymond E B Ketchum1, Tohru Horiguchi, Deyou Qiu, Robert M Williams, Rodney B Croteau.   

Abstract

Administering Taxus suspension cells with labeled 5alpha-hydroxytaxadiene and 5alpha,10beta-dihydroxytaxadiene, and the corresponding 5alpha-acetate esters, demonstrated that acetylation at C5 of the monool precursor promotes the formation of 14beta-hydroxy taxoids, such as taxuyunnanine C, at the expense of 13alpha-hydroxy taxoids, including Taxol and its congeners, but that the major bifurcation in taxoid biosynthesis, toward 13alpha- or 14beta-hydroxy taxoids, occurs after 10beta-hydroxylation of the taxane core.

Entities:  

Mesh:

Substances:

Year:  2006        PMID: 17157336      PMCID: PMC1995239          DOI: 10.1016/j.phytochem.2006.10.019

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


  17 in total

1.  Taxus (yews)--a highly toxic plant.

Authors:  L Ogden
Journal:  Vet Hum Toxicol       Date:  1988-12

2.  The kinetics of taxoid accumulation in cell suspension cultures of Taxus following elicitation with methyl jasmonate.

Authors:  R E Ketchum; D M Gibson; R B Croteau; M L Shuler
Journal:  Biotechnol Bioeng       Date:  1999-01-05       Impact factor: 4.530

3.  Taxol biosynthesis: differential transformations of taxadien-5 alpha-ol and its acetate ester by cytochrome P450 hydroxylases from Taxus suspension cells.

Authors:  A L Wheeler; R M Long; R E Ketchum; C D Rithner; R M Williams; R Croteau
Journal:  Arch Biochem Biophys       Date:  2001-06-15       Impact factor: 4.013

4.  Taxus metabolomics: methyl jasmonate preferentially induces production of taxoids oxygenated at C-13 in Taxus x media cell cultures.

Authors:  Raymond E B Ketchum; Christopher D Rithner; Deyou Qiu; You Sun Kim; Robert M Williams; Rodney B Croteau
Journal:  Phytochemistry       Date:  2003-03       Impact factor: 4.072

5.  Taxol biosynthesis: taxane 13 alpha-hydroxylase is a cytochrome P450-dependent monooxygenase.

Authors:  S Jennewein; C D Rithner; R M Williams; R B Croteau
Journal:  Proc Natl Acad Sci U S A       Date:  2001-11-13       Impact factor: 11.205

6.  Molecular cloning of a cytochrome P450 taxane 10 beta-hydroxylase cDNA from Taxus and functional expression in yeast.

Authors:  A Schoendorf; C D Rithner; R M Williams; R B Croteau
Journal:  Proc Natl Acad Sci U S A       Date:  2001-02-13       Impact factor: 11.205

7.  Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in Taxol biosynthesis.

Authors:  Kevin Walker; Shingo Fujisaki; Robert Long; Rodney Croteau
Journal:  Proc Natl Acad Sci U S A       Date:  2002-09-13       Impact factor: 11.205

8.  Taxol and derivatives: a biogenetic hypothesis.

Authors:  F Guéritte-Voegelein; D Guénard; P Potier
Journal:  J Nat Prod       Date:  1987 Jan-Feb       Impact factor: 4.050

9.  Cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene is the committed step of taxol biosynthesis in Pacific yew.

Authors:  A E Koepp; M Hezari; J Zajicek; B S Vogel; R E LaFever; N G Lewis; R Croteau
Journal:  J Biol Chem       Date:  1995-04-14       Impact factor: 5.157

10.  Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis.

Authors:  Stefan Jennewein; Robert M Long; Robert M Williams; Rodney Croteau
Journal:  Chem Biol       Date:  2004-03
View more
  10 in total

Review 1.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

2.  A systematic approach to expound the variations in taxane production under different dissolved oxygen conditions in Taxus chinensis cells.

Authors:  Chunfang Zhao; Guanghao Song; Chunhua Fu; Yanshan Dong; Hang Xu; Hua Zhang; Long Jiang Yu
Journal:  Plant Cell Rep       Date:  2015-11-30       Impact factor: 4.570

3.  Studies on Taxol® Biosynthesis. Preparation and Tritium Labeling of Biosynthetic intermediates by Deoxygenation of a Taxadiene Tetra-acetate Obtained from Japanese Yew.

Authors:  Tohru Horiguchi; Christopher D Rithner; Rodney Croteau; Robert M Williams
Journal:  J Labelled Comp Radiopharm       Date:  2008-08-01       Impact factor: 1.921

4.  Synthesis and In Vitro Evaluation of Taxol oxetane ring D precursors.

Authors:  Rüdiger Kaspera; Jonathan L Cape; Juan A Faraldos; Raymond E B Ketchum; Rodney B Croteau
Journal:  Tetrahedron Lett       Date:  2010-04-14       Impact factor: 2.415

5.  Studies on Taxol Biosynthesis: Preparation of Taxadiene-diol- and triol-Derivatives by Deoxygenation of Taxusin.

Authors:  Hui Li; Tohru Horiguchi; Rodney Croteau; Robert M Williams
Journal:  Tetrahedron       Date:  2008       Impact factor: 2.457

6.  Transcriptional responses and flavor volatiles biosynthesis in methyl jasmonate-treated tea leaves.

Authors:  Jiang Shi; ChengYing Ma; DanDan Qi; HaiPeng Lv; Ting Yang; QunHua Peng; ZongMao Chen; Zhi Lin
Journal:  BMC Plant Biol       Date:  2015-09-30       Impact factor: 4.215

7.  A Novel Hydroxylation Step in the Taxane Biosynthetic Pathway: A New Approach to Paclitaxel Production by Synthetic Biology.

Authors:  Raul Sanchez-Muñoz; Edgar Perez-Mata; Lorena Almagro; Rosa M Cusido; Mercedes Bonfill; Javier Palazon; Elisabeth Moyano
Journal:  Front Bioeng Biotechnol       Date:  2020-05-13

8.  Deep sequencing reveals transcriptome re-programming of Taxus × media cells to the elicitation with methyl jasmonate.

Authors:  Guiling Sun; Yanfang Yang; Fuliang Xie; Jian-Fan Wen; Jianqiang Wu; Iain W Wilson; Qi Tang; Hongwei Liu; Deyou Qiu
Journal:  PLoS One       Date:  2013-04-30       Impact factor: 3.240

9.  Jasmonate-responsive expression of paclitaxel biosynthesis genes in Taxus cuspidata cultured cells is negatively regulated by the bHLH transcription factors TcJAMYC1, TcJAMYC2, and TcJAMYC4.

Authors:  Sangram K Lenka; N Ezekiel Nims; Kham Vongpaseuth; Rosemary A Boshar; Susan C Roberts; Elsbeth L Walker
Journal:  Front Plant Sci       Date:  2015-02-26       Impact factor: 5.753

10.  Comparative metabolomic analysis reveals the variations in taxoids and flavonoids among three Taxus species.

Authors:  Ting Zhou; Xiujun Luo; Chengchao Zhang; Xinyun Xu; Chunna Yu; Zhifang Jiang; Lei Zhang; Huwei Yuan; Bingsong Zheng; Erxu Pi; Chenjia Shen
Journal:  BMC Plant Biol       Date:  2019-11-29       Impact factor: 4.215

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.