Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity

Pedras, M. Soledade C.; Chumala, Paulos; Suchý, Mojmı́r

doi:10.1016/s0031-9422(03)00441-2

Cited by 91 publications

(74 citation statements)

References 17 publications

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“…With the exception of T. arvense (Pedras et al, 2003) and Erucastrum gallicum (Pedras and Ahiahonu, 2004), wild crucifer species appear to produce only typecamalexin metabolites (Pedras et al, 2000). Indeed, camalexin (42) is recognized as the best studied phytoalexin.…”

Section: Nitrogen-and Sulphur-containing Compounds Phytoalexinsmentioning

confidence: 99%

Induced plant secondary metabolites for phytopatogenic fungi control: a review

Ribera

Zúñiga

2012

J. Soil Sci. Plant Nutr.

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Pathogenic fungi constitute one of the main infectious agents in plants, causing alterations during developmental stages including post-harvest. Phytopathogenic fungi are controlled by synthetic fungicides; however, the use of these is progressively restricted due to both, the harmful effects of pesticides on the environment and human health and the appearance of highly resistant fungal strains. Therefore, there is a great demand for novel natural fungicides. Higher plants are rich source of bioactive secondary metabolites of wide variety such as tannins, terpenoids, saponins, alkaloids, flavonoids, and other compounds, reported to have in vitro antifungal properties. Thus, secondary metabolites with antifungal activity represent an alternative for achieving a sustainable control of phytopathogenic fungi and to reduce the heavy reliance of synthetic pesticides used to control them. Plant antifungal metabolites may be preformed inhibitors that are present constitutively in healthy plants (phytoanticipins), or they may be synthesized de novo in response to pathogen attack or another stress conditions (phytoalexins). These molecules may be used directly or considered as a precursor for developing better fungicidal molecules. This review presents a selection of antifungal agents induced in plants during fungal attack that can be potentially used for phytopathogenic fungi control in crops.

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Section: Nitrogen-and Sulphur-containing Compounds Phytoalexinsmentioning

confidence: 99%

Induced plant secondary metabolites for phytopatogenic fungi control: a review

Ribera

Zúñiga

2012

J. Soil Sci. Plant Nutr.

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“…For example, they have been identified as phytoalexins in cauliflower (Brassica oleracea var. botrytis) and pennycress (Thlaspi arvense) (Pedras et al 2003;Pedras et al 2006). Isolated indol-3-acetonitrile has been reported to possess higher toxicity to E. carotovora and L. maculans than indol-3-carbinole, the product spontaneously formed from the instable indol-3-yl-methyl isothiocyanate (Mithen and Lewis 1986;Brader et al 2001).…”

Section: Effects Of Different Glucosinolate Hydrolysis Products On Pamentioning

confidence: 99%

Regulation and function of specifier proteins in plants

Burow

Wittstock

2008

Phytochem Rev

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Specifier proteins are responsible for the diversification of biologically active products formed upon myrosinase-catalyzed glucosinolate hydrolysis and are therefore assumed to have an impact on the defensive function of the glucosinolate-myrosinase system. Among glucosinolate hydrolysis products, the generation of epithionitriles and organic thiocyanates requires the presence of epithiospecifier protein (ESP) and thiocyanate-forming protein (TFP), respectively, while myrosinase alone is sufficient for the production of isothiocyanates. Both ESP and TFP also promote the formation of simple nitriles upon myrosinasecatalyzed glucosinolate hydrolysis. Only little is known about the biological effects of epithionitriles and thiocyanates. Moreover, simple nitriles have repeatedly been reported to be less toxic to plant pathogens and herbivorous insects than the correponding isothiocyanates. Thus, it has remained an open question how plants benefit from the presence of specifier proteins. In this review, we survey the biological effects of different types of glucosinolate hydrolysis products on insects and pathogens as well as the current knowlegde on the developmental, organ specific and stimuli-mediated regulation of specifier proteins. Integrating these findings can help us to better understand the ecological functions of plant specifier proteins as well as the co-evolution of glucosinolate-containing plants and their insect herbivores.

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“…The reaction mixture was diluted with H 2 O (2.0 ml), was extracted with Et 2 O (10.0 ml Â 2), the combined organic extract was dried over Na 2 SO 4 O (700 ml) was added drop wise and the mixture was allowed to stir for 15 min at r.t., followed by drop wise addition of bromoacetonitrile (160 ml, 2.70 mmol). 13,14 After being stirred for 20 min, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in water H 2 O (40.0 ml). The resulting mixture was neutralized with HCl (2.0 ml, 1 M) and was extracted with CH 2 Cl 2 (30.0 ml Â 3).…”

Section: Generalmentioning

confidence: 99%

Syntheses of perdeuterated indoles and derivatives as probes for the biosyntheses of crucifer phytoalexins

Pedras

Okinyo

2005

Labelled Comp Radiopharmac

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A simple two‐step preparation of [2H4]indole, a starting material necessary for the synthesis of various crucifer metabolites, starting with readily available 1H NMR solvent [2H5]nitrobenzene (99% deuterated) was developed. [4,5,6,7‐2H4]Indole 99% deuterated at the specified positions was then used to synthesize [4′,5′,6′,7′‐2H4]indolyl‐3‐acetaldoxime, [4′,5′,6′,7′‐2H4]1‐methoxyindolyl‐3‐acetaldoxime, [1″,1″,1″,4′,5′,6′,7′‐2H7]1‐methoxyindolyl‐3‐acetaldoxime, [4′,5′,6′,7′‐2H4]1‐methoxybrassinin, and [3,3,3,4′,5′,6′,7′‐2H7]1‐methoxybrassinin. Copyright © 2005 John Wiley & Sons, Ltd.

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Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity

Cited by 91 publications

References 17 publications

Induced plant secondary metabolites for phytopatogenic fungi control: a review

Induced plant secondary metabolites for phytopatogenic fungi control: a review

Regulation and function of specifier proteins in plants

Syntheses of perdeuterated indoles and derivatives as probes for the biosyntheses of crucifer phytoalexins

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