Literature DB >> 9862490

The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates.

S Bak1, H L Nielsen, B A Halkier.   

Abstract

A cDNA encoding CYP79B1 has been isolated from Sinapis alba. CYP79B1 from S. alba shows 54% sequence identity and 73% similarity to sorghum CYP79A1 and 95% sequence identity to the Arabidopsis T42902, assigned CYP79B2. The high identity and similarity to sorghum CYP79A1, which catalyses the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of the cyanogenic glucoside dhurrin, suggests that CYP79B1 similarly catalyses the conversion of amino acid(s) to aldoxime(s) in the biosynthesis of glucosinolates. Within the highly conserved 'PERF' and the heme-binding region of A-type cytochromes, the CYP79 family has unique substitutions that define the family-specific consensus sequences of FXP(E/D)RH and SFSTG(K/R)RGC(A/I)A, respectively. Sequence analysis of PCR products generated with CYP79B subfamily-specific primers identified CYP79B homologues in Tropaeolum majus, Carica papaya, Arabidopsis, Brassica napus and S. alba. The five glucosinolate-producing plants identified a CYP79B amino acid consensus sequence KPERHLNECSEVTLTENDLRFISFSTGKRGC. The unique substitutions in the 'PERF' and the heme-binding domain and the high sequence identity and similarity of CYP79B1, CYP79B2 and CYP79A1, together with the isolation of CYP79B homologues in the distantly related Tropaeolaceae, Caricaceae and Brassicaceae within the Capparales order, show that the initial part of the biosynthetic pathway of glucosinolates and cyanogenic glucosides is catalysed by evolutionarily conserved cytochromes P450. This confirms that the appearance of glucosinolates in Capparales is based on a cyanogen 'predisposition'. Identification of CYP79 homologues in glucosinolate-producing plants provides an important tool for tissue-specific regulation of the level of glucosinolates to improve nutritional value and pest resistance.

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Year:  1998        PMID: 9862490     DOI: 10.1023/a:1006064202774

Source DB:  PubMed          Journal:  Plant Mol Biol        ISSN: 0167-4412            Impact factor:   4.076


  18 in total

1.  The biosynthesis of cyanogenic glucosides in seedlings of cassava (Manihot esculenta Crantz).

Authors:  B Koch; V S Nielsen; B A Halkier; C E Olsen; B L Møller
Journal:  Arch Biochem Biophys       Date:  1992-01       Impact factor: 4.013

2.  Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin.

Authors:  S Bak; R A Kahn; H L Nielsen; B L Moller; B A Halkier
Journal:  Plant Mol Biol       Date:  1998-02       Impact factor: 4.076

3.  Structure and function of cytochromes P450: a comparative analysis of three crystal structures.

Authors:  C A Hasemann; R G Kurumbail; S S Boddupalli; J A Peterson; J Deisenhofer
Journal:  Structure       Date:  1995-01-15       Impact factor: 5.006

4.  Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum.

Authors:  R A Kahn; S Bak; I Svendsen; B A Halkier; B L Møller
Journal:  Plant Physiol       Date:  1997-12       Impact factor: 8.340

5.  Cytochrome P-450TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.

Authors:  O Sibbesen; B Koch; B A Halkier; B L Møller
Journal:  J Biol Chem       Date:  1995-02-24       Impact factor: 5.157

6.  Isolation of a Microsomal Enzyme System Involved in Glucosinolate Biosynthesis from Seedlings of Tropaeolum majus L.

Authors:  L. Du; B. A. Halkier
Journal:  Plant Physiol       Date:  1996-07       Impact factor: 8.340

Review 7.  Characterization of cytochrome P450TYR, a multifunctional haem-thiolate N-hydroxylase involved in the biosynthesis of the cyanogenic glucoside dhurrin.

Authors:  B A Halkier; O Sibbesen; B Koch; B L Møller
Journal:  Drug Metabol Drug Interact       Date:  1995

8.  Purification and characterization of recombinant cytochrome P450TYR expressed at high levels in Escherichia coli.

Authors:  B A Halkier; H L Nielsen; B Koch; B L Møller
Journal:  Arch Biochem Biophys       Date:  1995-10-01       Impact factor: 4.013

9.  The primary sequence of cytochrome P450tyr, the multifunctional N-hydroxylase catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.

Authors:  B M Koch; O Sibbesen; B A Halkier; I Svendsen; B L Møller
Journal:  Arch Biochem Biophys       Date:  1995-10-20       Impact factor: 4.013

10.  Involvement of cytochrome P450 in oxime production in glucosinolate biosynthesis as demonstrated by an in vitro microsomal enzyme system isolated from jasmonic acid-induced seedlings of Sinapis alba L.

Authors:  L Du; J Lykkesfeldt; C E Olsen; B A Halkier
Journal:  Proc Natl Acad Sci U S A       Date:  1995-12-19       Impact factor: 11.205

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  35 in total

Review 1.  Fungal resistance to plant antibiotics as a mechanism of pathogenesis.

Authors:  J P Morrissey; A E Osbourn
Journal:  Microbiol Mol Biol Rev       Date:  1999-09       Impact factor: 11.056

Review 2.  Myrosinase: gene family evolution and herbivore defense in Brassicaceae.

Authors:  L Rask; E Andréasson; B Ekbom; S Eriksson; B Pontoppidan; J Meijer
Journal:  Plant Mol Biol       Date:  2000-01       Impact factor: 4.076

3.  Control of axillary bud initiation and shoot architecture in Arabidopsis through the SUPERSHOOT gene.

Authors:  T Tantikanjana; J W Yong; D S Letham; M Griffith; M Hussain; K Ljung; G Sandberg; V Sundaresan
Journal:  Genes Dev       Date:  2001-06-15       Impact factor: 11.361

4.  Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3.

Authors:  Yunde Zhao; Anna K Hull; Neeru R Gupta; Kendrick A Goss; José Alonso; Joseph R Ecker; Jennifer Normanly; Joanne Chory; John L Celenza
Journal:  Genes Dev       Date:  2002-12-01       Impact factor: 11.361

5.  Identification of a new glucosinolate-rich cell type in Arabidopsis flower stalk.

Authors:  O A Koroleva; A Davies; R Deeken; M R Thorpe; A D Tomos; R Hedrich
Journal:  Plant Physiol       Date:  2000-10       Impact factor: 8.340

Review 6.  Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

Authors:  Abraham J Waldman; Tai L Ng; Peng Wang; Emily P Balskus
Journal:  Chem Rev       Date:  2017-04-04       Impact factor: 60.622

7.  Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis.

Authors:  Majse Nafisi; Sameer Goregaoker; Christopher J Botanga; Erich Glawischnig; Carl E Olsen; Barbara A Halkier; Jane Glazebrook
Journal:  Plant Cell       Date:  2007-06-15       Impact factor: 11.277

8.  Characterization of salicylic acid-induced genes in Chinese cabbage.

Authors:  Y-S Park; H-J Min; S-H Ryang; K-J Oh; J-S Cha; H Y Kim; T-J Cho
Journal:  Plant Cell Rep       Date:  2003-04-26       Impact factor: 4.570

9.  The gene controlling the indole glucosinolate modifier1 quantitative trait locus alters indole glucosinolate structures and aphid resistance in Arabidopsis.

Authors:  Marina Pfalz; Heiko Vogel; Juergen Kroymann
Journal:  Plant Cell       Date:  2009-03-17       Impact factor: 11.277

Review 10.  Auxin biosynthesis and storage forms.

Authors:  David A Korasick; Tara A Enders; Lucia C Strader
Journal:  J Exp Bot       Date:  2013-04-11       Impact factor: 6.992

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