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Plants within the Brassicales order generate glucosinolate hydrolysis products that can exert different biological effects on several organisms. Here, we evaluated the physiological effects of one of these compounds, benzyl cyanide (phenylacetonitrile), when exogenously applied on Arabidopsis thaliana. Treatment with benzyl cyanide led to a dose-dependent reduction of primary root length and total biomass. Further morphological changes like elongated hypocotyls, epinastic cotyledons, and increased formation of adventitious roots resembled a severe auxin-overproducer phenotype. The elevated auxin response was confirmed by histochemical staining and gene expression analysis of auxin-responsive genes. Nitriles are converted by specific enzymes, nitrilases (NIT1-3), to their corresponding carboxylic acids. The nitrilase mutants nit1 and nit2 tolerated benzyl cyanide treatments better than the wild type, with nit2 being less resistant than nit1. A NIT2RNAi line suppressing several nitrilases was resistant to all tested benzyl cyanide concentrations. When exposed to phenylacetic acid (PAA) – the corresponding carboxylic acid of benzyl cyanide – wild type and mutant seedlings were, however, equally susceptible and showed a more severe auxin phenotype than upon cyanide treatment. Here, we demonstrate that the auxin-like effects triggered by benzyl cyanide on Arabidopsis are due to its nitrilase-mediated conversion to the natural auxin PAA. Copyright © 2018 Urbancsok, Bones and Kissen. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY).

The present study was designed to determine the effects o fb enzylglucosinolate on endurance capacity in mice. Mice were orally administered either vehicle or benzylglucosinolate (0.015 or 0.03 mg/kg) via stomach intubation for a 6-week period. Benzylglucosinolate-treated mice showed a significantly increased endurance exercise capacity. Benzylglucosinolate significantly decreased blood lactate concentrations and significantly elevated plasma non-esterified fatty acid (NEFA) during exercise. Lastly, benzylglucosinolate treatment significantly decreased fat accumulation. These data suggest that benzylglucosinolate enhanced swimming endurance due to increased fatty acid utilization as an energy source.

Consumption of cruciferous vegetables is associated with reduced risk of developing cancer, a phenomenon attributed to glucosinolates, which are characteristic of these vegetables. We report production of the bioactive benzylglucosinolate in the noncruciferous plant Nicotiana benthamiana through metabolic engineering. The study includes identification of gamma-glutamyl peptidase 1 (GGP1), which substantially increased glucosinolate production by metabolizing an accumulating glutathione conjugate, an activity not previously described for glucosinolate biosynthesis or for proteins containing glutamine amidotransferase domains.

Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-27T11:27:28Z No. of bitstreams: 0Bitstream added on 2014-05-27T14:42:40Z : No. of bitstreams: 1 2-s2.0-84866391006.pdf: 228308 bytes, checksum: e563312c38c9110dbbfc038a95a234c3 (MD5) Made available in DSpace on 2014-05-27T11:27:28Z (GMT). No. of bitstreams: 0 Previous issue date: 2013-01-01 The limited availability of foods that are free of pesticides has led Brazil to search for alternative production methods to meet the desires of consumers. Currently, organic cultivation represents a production system that complies with general expectations of producers and consumers. Organic cultivation is particularly interesting mainly because of its effect on plant secondary metabolite content, which may help plants to naturally combat pests; in humans, these substances can also contribute to the prevention of chronic diseases. We report on the extraction of glucosinolates (both as total glucosinolates and as benzylglucosinolate) with trifluoroacetic acid addition in a 70:30 MeOH:water (v/v). Total glucosinolates, determined by a thioglucosidase coupled assay, were measured in different Brassicaceae species and were similar to values reported in the literature. For broccoli, analyses were carried out separately on inflorescences, leaves and stalks; analyses were also conducted on thermally processed samples to simulate cooking. Furthermore, when the analysis was conducted on conventional and organic products, the highest concentrations of these substances were most often found in organically cultivated Brassicaceae. The benzylglucosinolate concentrations were evaluated on the same samples using HPLC. The concentration of benzylglucosinolate was significantly higher in organically cultivated vegetables, as well. © 2012 Elsevier Ltd. Department of Chemistry and Biochemistry Biosciences Institute Universidade Estadual Paulista, UNESP, Rubião Junior CP 510, 18618-000 Botucatu, São Paulo Department of Food Science Faculty Pharmaceutical Science Universidade de São Paulo, USP, São Paulo Department of Comparative Biomedicine and Food Science University of Padova, Padova Department of Chemistry and Biochemistry Biosciences Institute Universidade Estadual Paulista, UNESP, Rubião Junior CP 510, 18618-000 Botucatu, São Paulo

Benzylglucosinolate degradation products were analysed in extracts of the seedlings of Lepidium sativum (‘curled cress’ and ‘plain cress’). Benzyl thiocyanate was positively identified in extracts of both types of cress, but it could not be detected after the onset of development of the true leaves. The relative percentages of benzylglucosinolate degradation products varied appreciably with age of the seedlings and with the length of time the shredded plant material was allowed to autolyse. Both types of cress behaved similarly on autolysis but differences were observed with seedling age.

The aroma volatiles of raw, fermented and roasted cocoa beans were extracted and concentrated to valid essences using well-established techniques. Analysis by GC and GC/MS showed at least 84 components of which 13 were identified for the first time as cocoa volatiles. In total, ca 5,66 and 65 μg of aroma components were obtained per g of raw, fermented and roasted cocoa beans, respectively. The most abundant groups of volatiles from fermented beans were alcohols ( ca 40%w/w of the total volatiles) and esters ( ca 32%), whilst those from roasted beans were pyrazines ( ca 40%) and aldehydes ( ca 23%). Trimethyl- and tetramethylpyrazine were also detected in fermented beans, and it is suggested that they contribute to the noticeable cocoa/chocolate aroma of fermented unroasted beans. Phenylacetonitrile, benzyl isothiocyanate and benzyl thiocyanate were all identified amongst cocoa volatiles, together showing the presence of precursor benzylglucosinolate in cocoa. Glucosinolate products were detected in roasted beans, and it seems likely that the enzyme thioglucoside glucohydrolase survived the conditions of roasting. Benzyl thiocyanate was detected only in raw beans, showing that the glucosinolate ‘thiocyanate–forming factor’ did not withstand conditions of fermentation

The content of glucosinolates and amines in green parts of Reseda media has been investigated. Benzylglucosinolate, 2-phenethylglucosinolate, and m-hydroxybenzylglucosinolate occur in appreciable amounts accompanied by minor amounts of other glucosinolates, benzylamine and m-hydroxybenzylamine. Isolation and identification of these compounds was made using ion-exchange chromatography, high voltage electrophoresis, GC, MS, and 13C-NMR spectroscopy. The glucosinolates were transformed into corresponding nitriles and isothiocyanates by thioglucoside glucohydrolase-catalysed hydrolysis and to the corresponding carboxylic acids by acid-catalysed hydrolysis. The content of glucosinolates and amines in leaves and inflorescences of R. media has been determined by UV-spectroscopy and GC.

Two unidentified analytical responses in a papaya extract were structurally determined by mass spectrometry to be benzyl isothiocyanate and phenyl acetonitrile. Both these compounds have previously been shown to result from degradation of benzylglucosinokte that occurs naturally in the seeds of the fruit. Characterization by mass spectrometry has now provided a convenient mechanism to detect both these degradation compounds in extracts resulting from routine pesticide residue analysis

In Glucosinolat–haltigen Pflanzen spaltet das Enzym, Glucosinolase, die Glucosinolate gewohnlich zu Isothocyanat, Glucose und Sulfat. Unter einigen Umstanden werden an Stelle des Isothiocyanats organisches Thiocyanat, Nitril oder cyklische Verbindungen gebildet. Gemas unseren Untersuchungen bilden sich Benzylthiocyanat und Phenylacetonitril als naturliche Produkte aus Benzylglucosinolat z.B. in zermahlenen, mit Wasser angeruhrten Samen von Lepidium sativum. Es ist unsere Hypothese, das das Enzym zuerst die Thioglucosid–Bindung spaltet, wonach eine Zwischenstufe entsteht, aus der sich Benzylthiocyanat und vermutlich auch Phenylacetonitril enzymatisch bilden. Das Vorkommen von Benzylisothiocyanat und Benzylamin kann man in Lepidium als Folge einer Artefaktebildung betrachten. Diese beiden Spaltprodukte entstehen chemisch wahrend des Analysenverfahrens. Man kann namlich Benzylisothiocyanat und –amin nicht mehr finden, nachdem die Reaktion ungestort im Pflanzenmaterial stattgefunden hat. Wenn aber die Spaltungsreaktion fruhzeitig abgebrochen wird, konnen Benzylisothiocyanat und –amin unter den Reaktionsprodukten gefunden werden. Wir vermuten, das das Benzylisothiocyanat gewohnlich aus der Zwischenstufe durch Lossen–Umlagerung gebildet wird, aber nur dann, wenn die Bildung von Thiocyanat und/oder Nitril verhindert wird. Das Benzylamin entsteht wahrscheinlich chemisch aus Benzylisothiocyanat.

Two distinct glucosinolases were isolated from mature seeds of yellow mustard by isoelectric focussing. One had an absolute requirements for ascorbic acid, had an isoelectric point of pH 5·55 (20°), and was inhibited by temperatures above 45°. The other glucosinolase did not require ascorbic acid, had an isoelectric point of pH 5·0 (20°), and showed a temperature optimum of about 75°. Both glucosinolases liberated p OH benzyl isothiocyanate, glucose and sulphate from p OH benzylglucosinolate. They had identical K m values and did not differ in response to various pH values.

The sole glucosinolate in the seed-bearing portion of Lepidium bonariense L., collected in Queensland, is shown to be p -methoxybenzylglucosinolate (IV). Seed material of L. hyssopifolium Desv., collected in Queensland, contains solely 3,4,5-trimethoxybenzylglucosinolate (V). A previous report on the presence of benzylglucosinolate in L. hyssopifolium is discussed.

Five species of the family Caricaceae were examined for glucosinolates. Like Carica papaya L., they all contained benzylglucosinolate (I, R = C 6 H 5 CH 2 ) as the sole thioglucoside.

Papaya seeds, which constitute 22% of the waste product from the papaya puree industry in Hawaii, were characterized in a preliminary study to evaluate their possible utilization. Oil was extracted from the seeds, and its fatty acid composition determined. Crude protein and crude fiber contents of the defatted meal were especially high, 40.0% and 48.9%. Benzylisothiocyanate content in the seed oil was 0.56% (w/w), and the benzylglucosinolate content in the seed meal was 1.0 (w/w).

Leaves of four South-American species of the genus Capparis (Capparidaceae) have been examined for their content of glucosinolates. From chromatographic evidence, it appears that C. baducca L., C. hastata Jacq., and C. odoratissima Jacq. contain methylglucosinolate. In C. flexuosa L., benzylglucosinolate is present, the first record of an aromatic glucosinolate in the Capparidaceae.