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Hydrolysis of glucosinolates and degradation of the unstable aglycone to isothiocyanates, nitriles and athiocyanates.
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f11-ijms-10-03371: Hydrolysis of glucosinolates and degradation of the unstable aglycone to isothiocyanates, nitriles and athiocyanates.

Mentions: Glucosinolates are sulphur-containing glucosides widespread in members of the family Cruciferae, including the genus Brassica, of relevant agronomic interest, and the weed Arabidopsis, a model plant in molecular genetic and biology. They represent a large chemical family including over 120 different compounds with known defensive properties against herbivores [44,45]. Glucosinolates can be subdivided into three major classes, depending on their side chain, which may be derived from aliphatic (methionine), indolyl (tryptophan) or aralkyl (phenylalanine) ╬▒-amino acids. Within individual plants, their distribution is tissue specific, as in oilseed rape, where aliphatic glucosinolates abound in leaves, whereas indolyl and phenylethyl glucosinolates predominate in roots and stems. Like cyanogenic glycosides, these compounds are also activated in response to tissue damage by the action of myrosinase (thioglucoside glucohydrolase or simply thioglucosidase), an enzyme that, in healthy plants, is separated from its glucosinolate substrates by subcellular compartmentalization (Scheme 6). The unstable aglycone thus generated may then form various products, including nitriles, thiocyanates and volatile isothiocyanates, being the latter the major and the most fungitoxic glucosinolate breakdown products (Scheme 6) [39,46,47]. Therefore, high levels of glucosinolates have also been associated with plant (Brassica) resistance to pathogens, such as the blackleg fungus Leptosphaeria maculans and the oomycete Peronospora parasitica, causal agents of stem canker and downy mildew, respectively [48,49]. Inhibition of ascospores of Mycosphaerella brassicae has been early reported, in both cabbage and cauliflower leaves [50] Interestingly, indolyl glucosinolates may be used as precursors for the biosynthesis of auxin, a indole/tryptophan derivative, by fungi that cause hyperplasic and hypertrophic tissue growth, such as the root gall fungus Plasmodiophora brassicae [37].

Chemical Diversity and Defence Metabolism: How Plants Cope with Pathogens and Ozone Pollution

Iriti M, Faoro F - Int J Mol Sci (2009)

Bottom Line: In plants, antibiotic compounds can be both preformed (phytoanticipins) and inducible (phytoalexins), the former including saponins, cyanogenic glycosides and glucosinolates.In some cases, the plant defence responses against pathogens and environmental pollutants may overlap, leading to the unspecific synthesis of similar molecules, such as phenylpropanoids.Finally, the synthesis of ethylene and polyamines can be regulated by ozone at level of S-adenosylmethionine (SAM), the biosynthetic precursor of both classes of hormones, which can, therefore, mutually inhibit their own biosynthesis with consequence on plant phenotype.

Affiliation: Università degli Studi di Milano, Dipartimento di Produzione Vegetale, Milano, Italy. marcello.iriti@unimi.it <marcello.iriti@unimi.it>

ABSTRACT
Chemical defences represent a main trait of the plant innate immune system. Besides regulating the relationship between plants and their ecosystems, phytochemicals are involved both in resistance against pathogens and in tolerance towards abiotic stresses, such as atmospheric pollution. Plant defence metabolites arise from the main secondary metabolic routes, the phenylpropanoid, the isoprenoid and the alkaloid pathways. In plants, antibiotic compounds can be both preformed (phytoanticipins) and inducible (phytoalexins), the former including saponins, cyanogenic glycosides and glucosinolates. Chronic exposure to tropospheric ozone (O(3)) stimulates the carbon fluxes from the primary to the secondary metabolic pathways to a great extent, inducing a shift of the available resources in favour of the synthesis of secondary products. In some cases, the plant defence responses against pathogens and environmental pollutants may overlap, leading to the unspecific synthesis of similar molecules, such as phenylpropanoids. Exposure to ozone can also modify the pattern of biogenic volatile organic compounds (BVOC), emitted from plant in response to herbivore feeding, thus altering the tritrophic interaction among plant, phytophagy and their natural enemies. Finally, the synthesis of ethylene and polyamines can be regulated by ozone at level of S-adenosylmethionine (SAM), the biosynthetic precursor of both classes of hormones, which can, therefore, mutually inhibit their own biosynthesis with consequence on plant phenotype.

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