135531-86-1,MFCD18451889
Catalog No.:AA00A4TV

135531-86-1 | camalexin

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1mg
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in stock  
$20.00   $14.00
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5mg
98%
in stock  
$48.00   $34.00
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10mg
98%
in stock  
$72.00   $50.00
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25mg
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50mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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Technical Information
Catalog Number:
AA00A4TV
Chemical Name:
camalexin
CAS Number:
135531-86-1
Molecular Formula:
C11H8N2S
Molecular Weight:
200.2596
MDL Number:
MFCD18451889
SMILES:
c1csc(n1)c1c[nH]c2c1cccc2
Properties
Computed Properties
 
Complexity:
210  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
1  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
2.7  

Downstream Synthesis Route

[1]Ayer,WilliamA.;Craw,PeterA.;Ma,Yu-Ting;Miao,Shichang[Tetrahedron,1992,vol.48,#14,p.2919-2924]

[1]Tetrahedron,1992,vol.48,p.2919-2924

[1]Fuerstner,Alois;Ernst,Andreas[Tetrahedron,1995,vol.51,#3,p.773-786]

[1]Sakamoto,Takao;Kondo,Yoshinori;Takazawa,Nobuo;Yamanaka,Hiroshi[JournaloftheChemicalSociety.PerkintransactionsI,1996,#16,p.1927-1934]

135531-86-1    161988-57-4   
3-hydroxy-3-(2'-thiazolyl)-2-oxindole 

[1]Pedras,M.SoledadeC.;Khan,AbdulQ.[Phytochemistry,2000,vol.53,#1,p.59-69]

Literature

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Title: Expression of ROS-responsive genes and transcription factors after metabolic formation of H(2)O(2) in chloroplasts.

Journal: Frontiers in plant science 20120101

Title: Quantification of camalexin, a phytoalexin from Arabidopsis thaliana: a comparison of five analytical methods.

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Title: Glutathione deficiency of the Arabidopsis mutant pad2-1 affects oxidative stress-related events, defense gene expression, and the hypersensitive response.

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Title: Crosstalk between abiotic ultraviolet-B stress and biotic (flg22) stress signalling in Arabidopsis prevents flavonol accumulation in favor of pathogen defence compound production.

Journal: Plant, cell & environment 20111101

Title: Conservation and clade-specific diversification of pathogen-inducible tryptophan and indole glucosinolate metabolism in Arabidopsis thaliana relatives.

Journal: The New phytologist 20111101

Title: Trichoderma-induced plant immunity likely involves both hormonal- and camalexin-dependent mechanisms in Arabidopsis thaliana and confers resistance against necrotrophic fungi Botrytis cinerea.

Journal: Plant signaling & behavior 20111001

Title: Transcript profiling of chitosan-treated Arabidopsis seedlings.

Journal: Journal of plant research 20110901

Title: The Arabidopsis phi class glutathione transferase AtGSTF2: binding and regulation by biologically active heterocyclic ligands.

Journal: The Biochemical journal 20110815

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Journal: PLoS pathogens 20110801

Title: Genomic analysis of the necrotrophic fungal pathogens Sclerotinia sclerotiorum and Botrytis cinerea.

Journal: PLoS genetics 20110801

Title: Role of camalexin, indole glucosinolates, and side chain modification of glucosinolate-derived isothiocyanates in defense of Arabidopsis against Sclerotinia sclerotiorum.

Journal: The Plant journal : for cell and molecular biology 20110701

Title: Camalexin induces apoptosis in T-leukemia Jurkat cells by increased concentration of reactive oxygen species and activation of caspase-8 and caspase-9.

Journal: Journal of natural medicines 20110701

Title: The microRNA miR393 re-directs secondary metabolite biosynthesis away from camalexin and towards glucosinolates.

Journal: The Plant journal : for cell and molecular biology 20110701

Title: Multiple roles of WIN3 in regulating disease resistance, cell death, and flowering time in Arabidopsis.

Journal: Plant physiology 20110701

Title: A permeable cuticle is associated with the release of reactive oxygen species and induction of innate immunity.

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Journal: Molecules and cells 20110630

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Title: Intronic T-DNA insertion renders Arabidopsis opr3 a conditional jasmonic acid-producing mutant.

Journal: Plant physiology 20110601

Title: Cytosolic γ-glutamyl peptidases process glutathione conjugates in the biosynthesis of glucosinolates and camalexin in Arabidopsis.

Journal: The Plant cell 20110601

Title: Phosphorylation of a WRKY transcription factor by two pathogen-responsive MAPKs drives phytoalexin biosynthesis in Arabidopsis.

Journal: The Plant cell 20110401

Title: Impact of the unfolded protein response on the pathogenicity of the necrotrophic fungus Alternaria brassicicola.

Journal: Molecular microbiology 20110301

Title: Phosphorylation of the Nicotiana benthamiana WRKY8 transcription factor by MAPK functions in the defense response.

Journal: The Plant cell 20110301

Title: Detoxification of cruciferous phytoalexins in Botrytis cinerea: spontaneous dimerization of a camalexin metabolite.

Journal: Phytochemistry 20110201

Title: Cell wall integrity and high osmolarity glycerol pathways are required for adaptation of Alternaria brassicicola to cell wall stress caused by brassicaceous indolic phytoalexins.

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Journal: Plant physiology 20110101

Title: Redirection of tryptophan metabolism in tobacco by ectopic expression of an Arabidopsis indolic glucosinolate biosynthetic gene.

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Title: Glutathione-indole-3-acetonitrile is required for camalexin biosynthesis in Arabidopsis thaliana.

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Title: Prunus domestica pathogenesis-related protein-5 activates the defense response pathway and enhances the resistance to fungal infection.

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Title: Imbalanced lignin biosynthesis promotes the sexual reproduction of homothallic oomycete pathogens.

Journal: PLoS pathogens 20090101

Title: Inducible expression of a Nep1-like protein serves as a model trigger system of camalexin biosynthesis.

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Title: Complex genetics control natural variation in Arabidopsis thaliana resistance to Botrytis cinerea.

Journal: Genetics 20081201

Title: The chromatin remodeler SPLAYED regulates specific stress signaling pathways.

Journal: PLoS pathogens 20081201

Title: Downstream targets of WRKY33.

Journal: Plant signaling & behavior 20081101

Title: Activation of MAPK kinase 9 induces ethylene and camalexin biosynthesis and enhances sensitivity to salt stress in Arabidopsis.

Journal: The Journal of biological chemistry 20081003

Title: The glutathione-deficient mutant pad2-1 accumulates lower amounts of glucosinolates and is more susceptible to the insect herbivore Spodoptera littoralis.

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Title: Wounding of Arabidopsis leaves causes a powerful but transient protection against Botrytis infection.

Journal: The Plant journal : for cell and molecular biology 20080801

Title: Direct fungicidal activities of C6-aldehydes are important constituents for defense responses in Arabidopsis against Botrytis cinerea.

Journal: Phytochemistry 20080801

Title: Glycerol-3-phosphate levels are associated with basal resistance to the hemibiotrophic fungus Colletotrichum higginsianum in Arabidopsis.

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Journal: The Journal of organic chemistry 20080718

Title: Brassinin oxidase, a fungal detoxifying enzyme to overcome a plant defense -- purification, characterization and inhibition.

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Journal: Planta 20080601

Title: A diffusible signal from germinating Orobanche ramosa elicits early defense responses in suspension-cultured Arabidopsis thaliana.

Journal: Plant signaling & behavior 20080301

Title: Phytoalexins and phytoanticipins from the wild crucifers Thellungiella halophila and Arabidopsis thaliana: rapalexin A, wasalexins and camalexin.

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Journal: BMC genomics 20080101

Title: A role for gene duplication and natural variation of gene expression in the evolution of metabolism.

Journal: PloS one 20080101

Title: Distinct roles of jasmonates and aldehydes in plant-defense responses.

Journal: PloS one 20080101

Title: Comparative transcriptome analysis of Arabidopsis thaliana infested by diamond back moth (Plutella xylostella) larvae reveals signatures of stress response, secondary metabolism, and signalling.

Journal: BMC genomics 20080101

Title: An extensive (co-)expression analysis tool for the cytochrome P450 superfamily in Arabidopsis thaliana.

Journal: BMC plant biology 20080101

Title: Roles of Arabidopsis WRKY3 and WRKY4 transcription factors in plant responses to pathogens.

Journal: BMC plant biology 20080101

Title: In silico comparison of transcript abundances during Arabidopsis thaliana and Glycine max resistance to Fusarium virguliforme.

Journal: BMC genomics 20080101

Title: Antioxidant status, peroxidase activity, and PR protein transcript levels in ascorbate-deficient Arabidopsis thaliana vtc mutants.

Journal: Journal of experimental botany 20080101

Title: Arabidopsis eIF2alpha kinase GCN2 is essential for growth in stress conditions and is activated by wounding.

Journal: BMC plant biology 20080101

Title: A rapid biosensor-based method for quantification of free and glucose-conjugated salicylic acid.

Journal: Plant methods 20080101

Title: Bacteria-derived peptidoglycans constitute pathogen-associated molecular patterns triggering innate immunity in Arabidopsis.

Journal: The Journal of biological chemistry 20071102

Title: Bacterial non-host resistance: interactions of Arabidopsis with non-adapted Pseudomonas syringae strains.

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Title: Identification of loci controlling non-host disease resistance in Arabidopsis against the leaf rust pathogen Puccinia triticina.

Journal: Molecular plant pathology 20071101

Title: Design, synthesis, and evaluation of potential inhibitors of brassinin glucosyltransferase, a phytoalexin detoxifying enzyme from Sclerotinia sclerotiorum.

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Title: Detoxification of the phytoalexin brassinin by isolates of Leptosphaeria maculans pathogenic on brown mustard involves an inducible hydrolase.

Journal: Phytochemistry 20070601

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

Journal: The Plant cell 20070601

Title: Regulatory variability of camalexin biosynthesis.

Journal: Journal of plant physiology 20070501

Title: Pathogen-associated molecular pattern recognition rather than development of tissue necrosis contributes to bacterial induction of systemic acquired resistance in Arabidopsis.

Journal: The Plant journal : for cell and molecular biology 20070501

Title: ABA is required for Leptosphaeria maculans resistance via ABI1- and ABI4-dependent signaling.

Journal: Molecular plant-microbe interactions : MPMI 20070401

Title: Transcriptional responses to exposure to the brassicaceous defence metabolites camalexin and allyl-isothiocyanate in the necrotrophic fungus Alternaria brassicicola.

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Title: Identification of PAD2 as a gamma-glutamylcysteine synthetase highlights the importance of glutathione in disease resistance of Arabidopsis.

Journal: The Plant journal : for cell and molecular biology 20070101

Title: Expression of a nitric oxide degrading enzyme induces a senescence programme in Arabidopsis.

Journal: Plant, cell & environment 20070101

Title: Erwinia carotovora elicitors and Botrytis cinerea activate defense responses in Physcomitrella patens.

Journal: BMC plant biology 20070101

Title: Histochemical and genetic analysis of host and non-host interactions of Arabidopsis with three Botrytis species: an important role for cell death control.

Journal: Molecular plant pathology 20070101

Title: The role of cytochrome P450 enzymes in the biosynthesis of camalexin.

Journal: Biochemical Society transactions 20061201

Title: Phytotoxicity and innate immune responses induced by Nep1-like proteins.

Journal: The Plant cell 20061201

Title: Nonenzymatic lipid peroxidation reprograms gene expression and activates defense markers in Arabidopsis tocopherol-deficient mutants.

Journal: The Plant cell 20061201

Title: Metabolic changes in Arabidopsis thaliana expressing the feedback-resistant anthranilate synthase alpha subunit gene OASA1D.

Journal: Phytochemistry 20061101

Title: Yeast increases resistance in Arabidopsis against Pseudomonas syringae and Botrytis cinerea by salicylic acid-dependent as well as -independent mechanisms.

Journal: Molecular plant-microbe interactions : MPMI 20061001

Title: ETR1-, JAR1- and PAD2-dependent signaling pathways are involved in C6-aldehyde-induced defense responses of Arabidopsis.

Journal: Plant science : an international journal of experimental plant biology 20060901

Title: CYP71B15 (PAD3) catalyzes the final step in camalexin biosynthesis.

Journal: Plant physiology 20060801

Title: The Arabidopsis flavin-dependent monooxygenase FMO1 is an essential component of biologically induced systemic acquired resistance.

Journal: Plant physiology 20060801

Title: Analysis of defensive responses activated by volatile allo-ocimene treatment in Arabidopsis thaliana.

Journal: Phytochemistry 20060701

Title: Potent induction of Arabidopsis thaliana flowering by elevated growth temperature.

Journal: PLoS genetics 20060701

Title: WRKY70 modulates the selection of signaling pathways in plant defense.

Journal: The Plant journal : for cell and molecular biology 20060501

Title: Transgressive segregation reveals two Arabidopsis TIR-NB-LRR resistance genes effective against Leptosphaeria maculans, causal agent of blackleg disease.

Journal: The Plant journal : for cell and molecular biology 20060401

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Tags:135531-86-1 Molecular Formula|135531-86-1 MDL|135531-86-1 SMILES|135531-86-1 camalexin
Catalog No.: AA00A4TV
135531-86-1,MFCD18451889
135531-86-1 | camalexin
Pack Size: 1mg
Purity: 98%
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Purity: 98%
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Technical Information
Catalog Number: AA00A4TV
Chemical Name: camalexin
CAS Number: 135531-86-1
Molecular Formula: C11H8N2S
Molecular Weight: 200.2596
MDL Number: MFCD18451889
SMILES: c1csc(n1)c1c[nH]c2c1cccc2
Properties
Complexity: 210  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 14  
Hydrogen Bond Acceptor Count: 2  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 1  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 2.7  
Downstream Synthesis Route
3034-53-5    120-72-9    141-78-6    135531-86-1    141690-88-2 

[1]Ayer,WilliamA.;Craw,PeterA.;Ma,Yu-Ting;Miao,Shichang[Tetrahedron,1992,vol.48,#14,p.2919-2924]

1670-85-5    621-62-5    135531-86-1 

[1]Tetrahedron,1992,vol.48,p.2919-2924

161988-57-4    135531-86-1 

[1]Fuerstner,Alois;Ernst,Andreas[Tetrahedron,1995,vol.51,#3,p.773-786]

154787-38-9    135531-86-1 

[1]Sakamoto,Takao;Kondo,Yoshinori;Takazawa,Nobuo;Yamanaka,Hiroshi[JournaloftheChemicalSociety.PerkintransactionsI,1996,#16,p.1927-1934]

135531-86-1    161988-57-4   
3-hydroxy-3-(2'-thiazolyl)-2-oxindole 

[1]Pedras,M.SoledadeC.;Khan,AbdulQ.[Phytochemistry,2000,vol.53,#1,p.59-69]

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Title: GCN2-dependent phosphorylation of eukaryotic translation initiation factor-2alpha in Arabidopsis.

Journal: Journal of experimental botany20080801

Title: Biosynthetic origin of BE-10988 in Streptomyces sp. BA10988.

Journal: The Journal of organic chemistry20080718

Title: Brassinin oxidase, a fungal detoxifying enzyme to overcome a plant defense -- purification, characterization and inhibition.

Journal: The FEBS journal20080701

Title: Pepper pectin methylesterase inhibitor protein CaPMEI1 is required for antifungal activity, basal disease resistance and abiotic stress tolerance.

Journal: Planta20080601

Title: A diffusible signal from germinating Orobanche ramosa elicits early defense responses in suspension-cultured Arabidopsis thaliana.

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Title: Phytoalexins and phytoanticipins from the wild crucifers Thellungiella halophila and Arabidopsis thaliana: rapalexin A, wasalexins and camalexin.

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Title: MADIBA: a web server toolkit for biological interpretation of Plasmodium and plant gene clusters.

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Title: A role for gene duplication and natural variation of gene expression in the evolution of metabolism.

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Title: Distinct roles of jasmonates and aldehydes in plant-defense responses.

Journal: PloS one20080101

Title: Comparative transcriptome analysis of Arabidopsis thaliana infested by diamond back moth (Plutella xylostella) larvae reveals signatures of stress response, secondary metabolism, and signalling.

Journal: BMC genomics20080101

Title: An extensive (co-)expression analysis tool for the cytochrome P450 superfamily in Arabidopsis thaliana.

Journal: BMC plant biology20080101

Title: Roles of Arabidopsis WRKY3 and WRKY4 transcription factors in plant responses to pathogens.

Journal: BMC plant biology20080101

Title: In silico comparison of transcript abundances during Arabidopsis thaliana and Glycine max resistance to Fusarium virguliforme.

Journal: BMC genomics20080101

Title: Antioxidant status, peroxidase activity, and PR protein transcript levels in ascorbate-deficient Arabidopsis thaliana vtc mutants.

Journal: Journal of experimental botany20080101

Title: Arabidopsis eIF2alpha kinase GCN2 is essential for growth in stress conditions and is activated by wounding.

Journal: BMC plant biology20080101

Title: A rapid biosensor-based method for quantification of free and glucose-conjugated salicylic acid.

Journal: Plant methods20080101

Title: Bacteria-derived peptidoglycans constitute pathogen-associated molecular patterns triggering innate immunity in Arabidopsis.

Journal: The Journal of biological chemistry20071102

Title: Bacterial non-host resistance: interactions of Arabidopsis with non-adapted Pseudomonas syringae strains.

Journal: Physiologia plantarum20071101

Title: Identification of loci controlling non-host disease resistance in Arabidopsis against the leaf rust pathogen Puccinia triticina.

Journal: Molecular plant pathology20071101

Title: Design, synthesis, and evaluation of potential inhibitors of brassinin glucosyltransferase, a phytoalexin detoxifying enzyme from Sclerotinia sclerotiorum.

Journal: Bioorganic & medicinal chemistry20070901

Title: Detoxification of the phytoalexin brassinin by isolates of Leptosphaeria maculans pathogenic on brown mustard involves an inducible hydrolase.

Journal: Phytochemistry20070601

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

Journal: The Plant cell20070601

Title: Regulatory variability of camalexin biosynthesis.

Journal: Journal of plant physiology20070501

Title: Pathogen-associated molecular pattern recognition rather than development of tissue necrosis contributes to bacterial induction of systemic acquired resistance in Arabidopsis.

Journal: The Plant journal : for cell and molecular biology20070501

Title: ABA is required for Leptosphaeria maculans resistance via ABI1- and ABI4-dependent signaling.

Journal: Molecular plant-microbe interactions : MPMI20070401

Title: Transcriptional responses to exposure to the brassicaceous defence metabolites camalexin and allyl-isothiocyanate in the necrotrophic fungus Alternaria brassicicola.

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Title: Identification of PAD2 as a gamma-glutamylcysteine synthetase highlights the importance of glutathione in disease resistance of Arabidopsis.

Journal: The Plant journal : for cell and molecular biology20070101

Title: Expression of a nitric oxide degrading enzyme induces a senescence programme in Arabidopsis.

Journal: Plant, cell & environment20070101

Title: Erwinia carotovora elicitors and Botrytis cinerea activate defense responses in Physcomitrella patens.

Journal: BMC plant biology20070101

Title: Histochemical and genetic analysis of host and non-host interactions of Arabidopsis with three Botrytis species: an important role for cell death control.

Journal: Molecular plant pathology20070101

Title: The role of cytochrome P450 enzymes in the biosynthesis of camalexin.

Journal: Biochemical Society transactions20061201

Title: Phytotoxicity and innate immune responses induced by Nep1-like proteins.

Journal: The Plant cell20061201

Title: Nonenzymatic lipid peroxidation reprograms gene expression and activates defense markers in Arabidopsis tocopherol-deficient mutants.

Journal: The Plant cell20061201

Title: Metabolic changes in Arabidopsis thaliana expressing the feedback-resistant anthranilate synthase alpha subunit gene OASA1D.

Journal: Phytochemistry20061101

Title: Yeast increases resistance in Arabidopsis against Pseudomonas syringae and Botrytis cinerea by salicylic acid-dependent as well as -independent mechanisms.

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Title: ETR1-, JAR1- and PAD2-dependent signaling pathways are involved in C6-aldehyde-induced defense responses of Arabidopsis.

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Journal: Plant physiology20060801

Title: Analysis of defensive responses activated by volatile allo-ocimene treatment in Arabidopsis thaliana.

Journal: Phytochemistry20060701

Title: Potent induction of Arabidopsis thaliana flowering by elevated growth temperature.

Journal: PLoS genetics20060701

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Title: Transgressive segregation reveals two Arabidopsis TIR-NB-LRR resistance genes effective against Leptosphaeria maculans, causal agent of blackleg disease.

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Journal: The Plant journal : for cell and molecular biology20050301

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Journal: The Plant journal : for cell and molecular biology20041101

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Title: Detoxification of the cruciferous phytoalexin brassinin in Sclerotinia sclerotiorum requires an inducible glucosyltransferase.

Journal: Phytochemistry20041001

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Journal: Organic & biomolecular chemistry20040407

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Title: Characterisation of an Arabidopsis-Leptosphaeria maculans pathosystem: resistance partially requires camalexin biosynthesis and is independent of salicylic acid, ethylene and jasmonic acid signalling.

Journal: The Plant journal : for cell and molecular biology20040101

Title: Genetic evidence that expression of NahG modifies defence pathways independent of salicylic acid biosynthesis in the Arabidopsis-Pseudomonas syringae pv. tomato interaction.

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Title: Arabidopsis local resistance to Botrytis cinerea involves salicylic acid and camalexin and requires EDS4 and PAD2, but not SID2, EDS5 or PAD4.

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Title: Infection of Arabidopsis with a necrotrophic pathogen, Botrytis cinerea, elicits various defense responses but does not induce systemic acquired resistance (SAR).

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Title: Characterization of an Arabidopsis-Phytophthora pathosystem: resistance requires a functional PAD2 gene and is independent of salicylic acid, ethylene and jasmonic acid signalling.

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