Glucocheirolin

Glucosinolate Profiling of Calepina irregularis.[Pubmed:30807036]

Nat Prod Commun. 2016 Sep;11(9):1329-1332.

Three different types of extracts of volatile isolates from aerial parts of Calepina irregularis (Asso) Thell. were investigated to uncover glucosinolates using indirect methods consisting of either non-enzymatic (thermal degradation) or enzymatic (with exogenous and endogenous myrosinase) hydrolysis, followed by GC-FID/MS analysis of the volatile isolates. The identification of volatile glucosinolate degradation products isolated from C. irregularis indirectly revealed the presence of seven glucosinolates, namely glucoiberverin, glucoiberin, Glucocheirolin, glucolepidiin, sinigrin, glucoerucin and glucotropacolin. Quantitatively the most important compound in the distillate (sample obtained by thermal degradation) was 3-(methylthio)propyl isothiocyanate (95 61/), the degradation product of glucoiberverin, which constituted almost the entire sample. Tw6 isothiocyanates, 3-(methylthio)propyl isothiocyanate (57.8%) and 3 (methylsulfinyl)propyl isothiocyanate (16.7%), originating from degradation of glucoiberverin and glucoiberin, respectively, were the most abundant compounds identified in the hydrolysate (sample obtained by exogenous myrosinase hydrolysis). Some isothiocyanates, 3-(methylthio)propyl isothiocyanate and 3-(methylsulfinyl)propyl isothiocyanate, were present in almost the same percentages (41.0% and 40.0%, respectively), in the autolysate (endogenous myrosinase hydrolysis).

A liquid chromatography-mass spectrometry approach to study "glucosinoloma" in broccoli sprouts.[Pubmed:22972788]

J Mass Spectrom. 2012 Sep;47(9):1198-206.

Glucosinolates are an important class of secondary plant metabolites, possessing health-promoting properties. Young broccoli plants are a very good source of glucosinolates with concentrations several times greater than in mature plants. The aim of our study was to develop a liquid chromatography-mass spectrometry and liquid chromatography/tandem mass spectrometry qualitative and quantitative method for the measure of glucosinolates in broccoli sprouts. The described method provides high sensitivity and specificity, allowing a rapid and simultaneous determination of 14 glucosinolates. The proposed method has been validated for eight glucosinolates: glucobrassicin, glucoraphanin, glucoiberin, glucoerucin, progoitrin, gluconapin, sinigrin and Glucocheirolin. The linear range was 1-150 microg ml(-1), the intra-day and inter-day precision values are within 6% and 8% at the lower limit of quantification, while the overall recovery of the eight glucosinolates was 99 +/- 9%. This validated method was used successfully for analysis of glucosinolates content of broccoli sprouts grown in different conditions.

Determination of glucosinolates in traditional Chinese herbs by high-performance liquid chromatography and electrospray ionization mass spectrometry.[Pubmed:17086388]

Anal Bioanal Chem. 2006 Dec;386(7-8):2225-32.

A reversed-phase HPLC method has been developed for determination of twelve intact glucosinolates--glucoiberin, Glucocheirolin, progoitrin, sinigrin, epiprogoitrin, glucoraphenin, sinalbin, gluconapin, glucosibarin, glucotropaeolin, glucoerucin, and gluconasturtiin--in ten traditional Chinese plants. The samples were extracted with methanol and the extracts were cleaned on an activated Florisil column. A mobile phase gradient prepared from methanol and 30 mmol L(-1) ammonium acetate at pH 5.0 enabled baseline separation of the glucosinolates. Glucosinolate detection was confirmed by quadrupole time-of-flight tandem mass spectrometric analysis in negative-ionization mode. Detection limits ranged from 0.06 to 0.36 microg g(-1) when 5 g of dried plant was analyzed. Recoveries of the glucosinolates were better than 85% and precision (relative standard derivation, n = 3) ranged from 5.3 to 14.6%. Analysis of the glucosinolates provided scientific evidence enabling differentiation of three pairs of easily confused plants.

Production of glucosinolate hydrolysis products in Farsetia aegyptia suspension cultures following elicitation.[Pubmed:15885925]

Fitoterapia. 2005 Jun;76(3-4):288-95.

Levels of glucosinolates in Farsetia aegyptia var. ovalis suspension cultures were monitored after treatment with yeast extract, chitosan, methyl jasmonate, ampicillin, and Phytophthora infestans autoclaved mycelia as elicitors. Glucosinolates were identified, and an estimation of their levels obtained from their hydrolysis products. Yeast extract improved glucotropaeolin (benzyl-glucosinolate) and Glucocheirolin [3-(methylsulfonyl)propyl-glucosinolate] accumulation, and production of sec-butyl, isobutylglucosinolate and gluconasturtiin (2-phenylethyl-glucosinolate) was only detected in yeast elicited cultures. Increases were shown in glucotropaeolin levels in cultures elicited using methyljasmonate, and chitosan and methyljasmonate in combination.

In vitro antiproliferative activity of isothiocyanates and nitriles generated by myrosinase-mediated hydrolysis of glucosinolates from seeds of cruciferous vegetables.[Pubmed:10956152]

J Agric Food Chem. 2000 Aug;48(8):3572-5.

A comparison of the effect of isothiocyanates and nitriles derived from some glucosinolates, namely, epi-progoitrin, sinalbin, glucotropaeolin, Glucocheirolin, and glucoraphenin, on human erythroleukemic in vitro cultured cells was studied. Many studies have in fact evidenced that a consumption of vegetable containing glucosinolates could reduce the development of colorectal cancer. In the experimental conditions used, the production of isothiocyanates and nitriles from glucosinolates is almost quantitative as confirmed by HPLC or GC-MS analysis. The obtained results demonstrated that in general nitriles are considerably less potent than the corresponding isothiocyanates in inhibiting cancer cell growth. Particularly, the isothiocyanates inhibitory activity on K562 cells growth is higher in the case of products derived from epi-progoitrin, glucotropaeolin, glucoraphenin, and Glucocheirolin; while for nitriles the higher activity in inhibiting K562 cells growth is showed by sinalbin-derived product. Considering the antiproliferative activity found for isothiocyanates and nitriles, further studies will be aimed to the possible application of glucosinolate-derived products as chemopreventive cancer agents for the reduction of colorectal cancer.

Myrosinase-generated isothiocyanate from glucosinolates: isolation, characterization and in vitro antiproliferative studies.[Pubmed:9354235]

Bioorg Med Chem. 1997 Sep;5(9):1799-806.

Epidemiological and pharmacological studies have shown that colorectal cancer development could be reduced by consuming vegetables that contain glucosinolates. In view of this the effect of some glucosinolates and their isothiocyanate (ITC)-derived products on in vitro cell growth was studied. We report the isolation and characterization of ITCs derived from glucosinolates by using HPLC, GC-MS, and NMR techniques. The in vitro activity of ITCs on human erythroleukemic K562 cells has been investigated by using two alternative approaches: the in situ and pre-mix methods. No differences in antiproliferative activity were found comparing the effect of ITCs produced either of these methods. In the experimental conditions used, the production of ITCs from glucosinolates is almost quantitative as confirmed by HPLC or GC-MS analysis. The ITCs' inhibitory activity on K562 cells growth is particularly evident in the cases of ITCs derived from sinigrin, progoitrin, epi-progoitrin, glucotropaeolin and Glucocheirolin. Finally, the antiproliferative activity of the ITCs obtained from glucoraphenin, taken as an example, was determined on other tumor cell lines with a different origin and hystotype. Considering the antiproliferative activity found for ITCs these compounds could be considered potentially responsible for the reduction of colorectal cancer associated with diets rich in cruciferous vegetables. Further studies will be aimed at the possible application of glucosinolate-derived products as chemopreventive cancer agents.

Effects of plant nutrition on the balance of insect relevant cardenolides and glucosinolates in Erysimum cheiranthoides.[Pubmed:28306812]

Oecologia. 1995 Apr;102(1):95-101.

The possible effects of environmental stress on plant chemistry that are important to herbivorous insects were examined by growing a wild crucifer, Erysimum cheiranthoides, under different nutrient regimes. Oviposition by the cabbage butterfly, Pieris rapae, is thought to be affected by the balance of glucosinolates (stimulants) and cardenolides (deterrents) at the surface of leaves. E. cheiranthoides seedlings were provided with three levels of nitrogen and two levels of sulfur for a period of 15 days before analysis of semiochemicals in whole leaf tissue and at the surface of the foliage. The ratio of cardenolides to glucosinolates in the plants at elevated C/N ratios followed the carbon/nutrient balance hypothesis. However, a high nitrogen supply enhanced biomass production to the extent that concentrations of secondary compounds were unchanged or reduced. The concentration of glucosinolates (glucoiberin and Glucocheirolin) at the surface was positively related to whole tissue levels. However, cardenolide (erysimoside and erychroside) concentrations, which were highest in leaf tissue of nitrogen-deficient plants, had the lowest surface levels on foliage of these plants. Possible reasons for differential expression of cardenolides and glucosinolates in a plant as a result of nutrient deficiency are discussed.

A chemical basis for differential acceptance ofErysimum cheiranthoides by twoPieris species.[Pubmed:24248868]

J Chem Ecol. 1993 Feb;19(2):195-210.

Wormseed mustard,Erysimum cheiranthoides, is unacceptable as a host for the cabbage butterfly,Pieris rapae. However, it is preferred for oviposition byPieris napi oleracea in the greenhouse. Isolation and identification of the oviposition stimulants toP. napi oleracea were accomplished by C18 open-column chromatography, TLC, ion-exchange chromatography, HPLC, UV, and NMR spectroscopy. Glucoiberin and Glucocheirolin were identified as the most active stimulants. The extracted glucoiberin was as stimulatory as Glucocheirolin, although its concentration in theErysimum plants was about 10 times lower than that of Glucocheirolin. These glucosinolates were only weak stimulants toP. rapae. Furthermore,P. rapae was strongly deterred by the cardenolides, erysimoside and erychroside, fromE. cheiranthoides, andP. napi oleracea was less sensitive to these compounds. No other deterrent toP. napi oleracea was detected in this plant species. The results explain the differential acceptance ofE. cheiranthoides by these twoPieris species.

Hydrolysis of a naturally occurring beta-glucoside by a broad-specificity beta-glucosidase from liver.[Pubmed:3099756]

Biochem J. 1986 Jul 15;237(2):469-76.

We have isolated from guinea-pig liver a broad-specificity beta-glucosidase of unknown function that utilizes as its substrate non-physiological aryl glycosides (e.g. 4-methylumbelliferyl beta-D-glucopyranoside, p-nitrophenyl beta-D-glucopyranoside). The present paper documents that this enzyme can be inhibited by various naturally occurring glycosides, including L-picein, dhurrin and Glucocheirolin. In addition, L-picein, which acts as a competitive inhibitor of the broad-specificity beta-glucosidase (Ki 0.65 mM), is also a substrate for this enzyme (Km 0.63 mM; Vmax. 277,000 units/mg). Heat-denaturation, kinetic competition studies, chromatographic properties and pH optima all argue strongly that the broad-specificity beta-glucosidase is responsible for the hydrolysis of both the non-physiological aryl glycosides and L-picein. This paper demonstrates that beta-glucosidase can catalyse the hydrolysis of a natural glycoside, and may provide a key to understanding the function of this enigmatic enzyme. A possible role in the metabolism of xenobiotic compounds is discussed.