Barbarea verna as a source of 2-phenylethyl glucosinolate, precursor of cancer chemopreventive phenylethyl isothiocyanate

Barillari, Jessica; Gueyrard, David; Rollin, Patrick; Iori, Renato

doi:10.1016/s0367-326x(01)00320-3

Cited by 44 publications

(21 citation statements)

References 12 publications

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“…Compound 8 (1, 3-diphenethyl urea) was detected in the sprout of land cress ( Barbarea verna ) at the highest concentration, although the extract showed only weak sEH inhibitory potency. The occurrence of compound 8 in land cress is consistent with previous reports that this plant is rich in phenethyl glucosinolate [51,54,55]. Given the high concentration of phenethyl glucosinolate in land cress, this plant may be ideal for further optimization of sEH inhibition.…”

Section: Resultssupporting

confidence: 88%

Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales

et al. 2017

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Recently, dibenzylurea-based potent soluble epoxide hydrolase (sEH) inhibitors were identified in Pentadiplandra brazzeana, a plant in the order Brassicales. In an effort to generalize the concept, we hypothesized that plants that produce benzyl glucosinolates and corresponding isothiocyanates also produce these dibenzylurea derivatives. Our overall aim here was to examine the occurrence of urea derivatives in Brassicales, hoping to find biologically active urea derivatives from plants. First, plants in the order Brassicales were analyzed for the presence of 1, 3-dibenzylurea (compound 1), showing that three additional plants in the order Brassicales produce the urea derivatives. Based on the hypothesis, three dibenzylurea derivatives with sEH inhibitory activity were isolated from maca (Lepidium meyenii) roots. Topical application of one of the identified compounds (compound 3, human sEH IC50 = 222 nM) effectively reduced pain in rat inflammatory pain model, and this compound was bioavailable after oral administration in mice. The biosynthetic pathway of these urea derivatives was investigated using papaya (Carica papaya) seed as a model system. Finally, a small collection of plants from the Brassicales order was grown, collected, extracted and screened for sEH inhibitory activity. Results show that several plants of the Brassicales order could be potential sources of urea-based sEH inhibitors.

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Section: Resultssupporting

confidence: 88%

Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales

et al. 2017

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“…Tzin et al [219] transferred the bacterial E. coli bifunctional PheA (chorismate mutase/prephenate dehydratase) gene in A. thaliana which resulted in increased accumulation of Phe, Phe GSL derivatives, BGSL and 2-phenylethyl GSL, and their two ITCs, phenyacetonitrile and 2-PEITC [88,220]. Similarly, Huang et al [221] reported a 160-fold increased accumulation of free Phe and a 30-fold increase in two phenylethyl GSL in transgenic Arabidopsis plants overexpressing a mutant arogenate dehydratase 2 (adt2-D) gene from Arabidopsis.…”

Section: Engineering Plants With Altered Gslsmentioning

confidence: 99%

Engineering Glucosinolates in Plants: Current Knowledge and Potential Uses

Venkidasamy

Gururani

et al. 2012

Appl Biochem Biotechnol

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Glucosinolates (GSL) and their derivatives are well known for the characteristic roles they play in plant defense as signaling molecules and as bioactive compounds for human health. More than 130 GSLs have been reported so far, and most of them belong to the Brassicaceae family. Several enzymes and transcription factors involved in the GSL biosynthesis have been studied in the model plant, Arabidopsis, and in a few other Brassica crop species. Recent studies in GSL research have defined the regulation, distribution, and degradation of GSL biosynthetic pathways; however, the underlying mechanism behind transportation of GSLs in plants is still largely unknown. This review highlights the recent advances in the metabolic engineering of GSLs in plants and discusses their potential applications.

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“…These intermediates may also react with water resulting in the formation of benzylic alcohols, which still may react with nucleophiles, especially under acid conditions or upon enzymatic sulpho conjugation [26,27]. chromatography, as previously described [10,11]. The extract was loaded on a DEAE-Sephadex A-25 (Pharmacia, Milan, Italy) anion-exchange column (150 Â 26 mm) conditioned with 25 mM acetate buffer (pH 5.6).…”

Section: Laboratory a (Research Centre For Industrialmentioning

confidence: 99%

Identification of glucosinolate congeners able to form DNA adducts and to induce mutations upon activation by myrosinase

Baasanjav-Gerber

Monien

Mewis

et al. 2011

Molecular Nutrition Food Res

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Barbarea verna as a source of 2-phenylethyl glucosinolate, precursor of cancer chemopreventive phenylethyl isothiocyanate

Cited by 44 publications

References 12 publications

Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales

Occurrence of urea-based soluble epoxide hydrolase inhibitors from the plants in the order Brassicales

Engineering Glucosinolates in Plants: Current Knowledge and Potential Uses

Identification of glucosinolate congeners able to form DNA adducts and to induce mutations upon activation by myrosinase

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