Identification of the major glucosinolate (4-mercaptobutyl glucosinolate) in leaves of Eruca sativa L. (salad rocket)

Populations of Eruca sativa (Brassicaceae) from desert and Mediterranean (Med) habitats in Israel differ in their defense against larvae of the generalist Spodoptera littoralis but not the specialist Pieris brassicae. Larvae of the generalist insect feeding on plants of the Med population gained significantly less weight than those feeding on the desert plants, and exogenous application of methyl jasmonate (MJ) on leaves of the Med plants significantly reduced the level of damage created by the generalist larvae. However, MJ treatment significantly induced resistance in plants of the desert population, whereas the generalist larvae caused similar damage to MJ‐induced and noninduced plants. Analyses of glucosinolates and expression of genes in their synthesis pathway indicated that defense in plants of the Med population against the generalist insect is governed by the accumulation of glucosinolates. In plants of the desert population, trypsin proteinase inhibitor activity was highly induced in response to herbivory by S. littoralis. Analysis of genes in the defense‐regulating signaling pathways suggested that in response to herbivory, differences between populations in the induced levels of jasmonic acid, ethylene, and salicylic acid mediate the differential defenses against the insect. In addition, expression analysis of myrosinase‐associated protein NSP2 suggested that in plants of the desert population, glucosinolates breakdown products were primarily directed to nitrile production. We suggest that proteinase inhibitors provide an effective defense in the desert plants, in which glucosinolate production is directed to the less toxic nitriles. The ecological role of nitrile production in preventing infestation by specialists is discussed.

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“…A dimeric form of glucosativin (Bennett et al. 2002) was also identified (Tables S4 and S5, Supporting Information).…”

Section: Resultsmentioning

confidence: 96%

Intraspecific variation in defense against a generalist lepidopteran herbivore in populations of Eruca sativa (Mill.)

Ogran

Landau

Hanin

et al. 2016

Ecology and Evolution

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“…4,5 Research results vary as to which glucosinolates predominate in rocket; in one study it was 4-methylthiobutylglucosinolate (glucoerucin), 6 while in another it was a new glucosinolate, 4-mercaptobutyl glucosinolate (glucosativin). 7 The volatiles of rocket leaves, obtained by different isolation methods, were researched. Miyazawa et al reported that the main volatile, after simultaneous hydrodistillation-extraction in a LikensNickerson-type apparatus, was erucin (ca.…”

Section: Introductionmentioning

confidence: 99%

“…9 Bennett et al reported that volatiles, after autolysis of fresh tissues (both seedlings and leaves) and extraction by CH 2 Cl 2 , contained 4-methylsulphinylbutyl ITC (leaf extract), 4-methylthiobutyl ITC (seedling and leaf extracts) and mercaptobutyl ITC (seedling and leaf extracts). 7 Also, bis (4-isothiocyanatobutyl)disulphide, a unique volatile compound, was reported among rocket volatiles. 7 4-Methylthiobutyl isothiocyanate (erucin), according to an Italian study, not only showed indirect antioxidant activity (in inducing phase 2 enzymes such as sulphoraphane) but additionally had direct antioxidant activity, decomposing hydroperoxides and hydrogen peroxide (which are often the catalysts that trigger the cancer cascade).…”

Section: Introductionmentioning

confidence: 99%

“…7 Also, bis (4-isothiocyanatobutyl)disulphide, a unique volatile compound, was reported among rocket volatiles. 7 4-Methylthiobutyl isothiocyanate (erucin), according to an Italian study, not only showed indirect antioxidant activity (in inducing phase 2 enzymes such as sulphoraphane) but additionally had direct antioxidant activity, decomposing hydroperoxides and hydrogen peroxide (which are often the catalysts that trigger the cancer cascade). Moreover, the by-product of this radical scavenging activity was sulphoraphane itself, the most potent phase 2 enzyme inducer in the isothiocyanate family.…”

Section: Introductionmentioning

confidence: 99%

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Free and bound volatiles of rocket (Eruca sativa Mill.)

Blažević

Mastelić

2008

Flavour & Fragrance J

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Volatile fractions of rocket (Eruca sativa Mill.) ½owers and leaves with green beans were isolated by hydrodistillation in a Clevenger apparatus from fresh plant material prior to and after autolysis and from dried plant material. All isolates of volatile compounds were analysed by gas chromatography/gas chromatography-mass spectrometry (GC/GC-MS). Sulphur and/or nitrogen compounds, fatty acids and esters, aliphatic alcohols and carbonyl compounds and some other compounds in smaller percentages were identi¼ed. The main sulphur and/or nitrogen components were glucoerucin degradation volatiles: 4-methylthiobutyl isothiocyanate (9.0 -81.7%) and 5-methylthiopentanenitrile (2.4 -17.7%). Also, fatty acids and esters were identi¼ed as major components, such as: decanoic acid (1.2-32.8%), hexadecanoic acid (2.7-22.3%), dodecanoic acid (0.6-8.7%), (E,E)-9,12-octadecadienoic acid (6.5%), tetradecanoic acid (1.5-6.4%), methyl linolenate (

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“…Virtually all other members of the Brassicaceae contain glucosinolates as secondary metabolites that act as part of plant defense mechanisms. Glucosinolates and their hydrolysis products (isothiocyanates, thiocyanates, nitriles and sulphates) have also been implicated in giving rocket its characteristic pungent aromas and flavours (Bennett et al 2002) and volatiles (such as isothiocyanates and indoles).…”

Section: Gc-ms Analysis Of Essential Oilmentioning

confidence: 99%

Chemical composition and biological activities ofEruca vesicariasubsp. longirostrisessential oils

Hichri

Mosbah

Majouli

et al. 2016

Pharmaceutical Biology

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Context To date, there are no reports to validate the Tunisian traditional and folklore claims of Eruca vesicaria (L) Cav. subsp. longirostris (Brassicaceae) for the treatment of disease. Objective Investigation of the chemical composition antimicrobial and antioxidant activity of essential oils from Eruca longirostris leaves, stems, roots and fruits. Materials and methods The essential oils of E. longirostris from leaves, stems, roots and fruits were obtained after 4 h of hydrodistillation. Chemical compositions were determined using a combination of GC/FID and GC/MS. The in vitro antimicrobial activity of the volatile constituents of E. longirostris was performed in sterile 96-well microplates against three Gram-positive, four Gram-negative bacteria and one strain as yeast. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration values were reported. Furthermore, the antioxidant activity was evaluated by DPPH and ABTS assays. Results The main compound for fruits, stems and roots was the erucin (96.6%, 85.3% and 83.7%, respectively), while b-elemene (35.7%), hexahydrofarnesylacetone (23.9%), (E)-b-damascone (15.4%), erucin (10.6%) and a-longipinene (9.6%) constituted the major compounds in the essential oil of the leaves. The experimental results showed that in all tests, essential oil of fruits showed the better antioxidant activity than the others. On the other hand, the oils of stems, fruits and roots showed significant antimicrobial activity with MIC values ranging from 0.125 to 0.31 mg/mL against Candida species, Gram-positive and Gram-negative bacteria, mainly Salmonella enterica. Conclusions The present results indicate that essential oils of E. longirostris can be used as a source of erucin. ARTICLE HISTORY

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Identification of the major glucosinolate (4-mercaptobutyl glucosinolate) in leaves of Eruca sativa L. (salad rocket)

Cited by 110 publications

References 13 publications

Intraspecific variation in defense against a generalist lepidopteran herbivore in populations of Eruca sativa (Mill.)

Intraspecific variation in defense against a generalist lepidopteran herbivore in populations of Eruca sativa (Mill.)

Free and bound volatiles of rocket (Eruca sativa Mill.)

Chemical composition and biological activities ofEruca vesicariasubsp. longirostrisessential oils

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