glucoraphanin and glucobrassicin

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Topics: Brassica; Chromatography, Liquid; Cooking; Glucose; Glucosinolates; Imidoesters; Indoles; Microwaves; Oximes; Sulfoxides; Tandem Mass Spectrometry

Topics: Brassica; Chromatography, High Pressure Liquid; Genotype; Glucosinolates; Imidoesters; Indoles; Oximes; Spectrometry, Mass, Electrospray Ionization; Sulfoxides

Cruciferous foods rich in health-promoting metabolites are of particular interest to consumers as well as being a good source of bioactives-enriched ingredients. Several elicitors have been used to stimulate the biosynthesis and accumulation of secondary metabolites in foods; however, little is known about the response of new hybrid varieties, such as Bimi®, under field-crop production conditions. Therefore, this study was designed to evaluate the effect of salicylic acid (200 μmol L. The results indicate that the combined treatment (SA + MeJA) significantly increased the content of glucosinolates in the inflorescences and that MeJA was the most effective elicitor in leaves. Regarding the aqueous extracts, the greatest amount of glucosinolates was extracted at 30 min - except for the leaves elicited with MeJA, for which 15 min was optimal.. The elicitation in the field enriched leaves in glucobrassicin (GB), 4-methoxyglucobrassicin (MGB), and neoglucobrassicin (NGB) and stems and inflorescences in glucoraphanin, 4-hydroxyglucobrassicin, GB, MGB, and NGB. In this way, this enhanced vegetable material favored the presence of bioactives in the extracts, which is of great interest regarding enriched foods and ingredients with added value obtained from them. © 2019 Society of Chemical Industry.

Topics: Acetates; Brassica; Cyclopentanes; Food Analysis; Glucosinolates; Imidoesters; Indoles; Inflorescence; Oximes; Oxylipins; Plant Leaves; Plant Stems; Salicylic Acid; Sulfoxides

Evolution of important glucosinolates (GLSs), namely, sinigrin, glucoraphanin, glucoerucin and glucobrassicin, in three commonly consumed Brassica vegetables viz. white cabbage, Chinese cabbage and bok choy during their processing into vegetable powder was investigated. Drying was noted to be a major processing step causing significant losses of GLSs. Interestingly, different GLSs and even the same GLSs in different vegetables showed different thermal stabilities during drying. The stability of GLSs in vegetable powder during in vitro gastric digestion was also studied. Glucoraphanin exhibited the highest stability while glucobrassicin was the most vulnerable GLS under in vitro gastric conditions. White cabbage is found to be a promising material for the production of vegetable powder as it contains high contents of GLSs, especially glucoraphanin and glucoerucin, which are important precursors of anticarcinogenic compounds, namely sulforaphane and erucin. These two GLSs were also noted to be stable during in vitro gastric digestion.

Topics: Brassica; Dietary Fiber; Digestion; Food Handling; Glucose; Glucosinolates; Imidoesters; Indoles; Nutritive Value; Oximes; Powders; Sulfoxides; Vegetables

We report the spectrophotometric determination of total polyphenols, flavonoids, glucosinolates and antioxidant activity in seeds, seedlings and leaves of Tuscan black kale. The highest content of phytochemicals was observed in 10 days sprouts and antioxidant activity was maximum in 2, 4 days seedlings. Identification and characterisation of phytochemicals were performed by mass spectrometry (MS), high resolution and tandem MS with electrospray ionisation mode. Low-molecular-weight metabolites were evidenced in seeds while metabolites at high m/z range were detected in cotyledons and leaves. MS spectra evidenced different phenolic compounds (flavonoid caffeoyl glucose, hydroxycinnamic acid sinapine) and glucosinolates (glucoerucin, glucobrassicin and glucoraphanin) in function of developmental stage; galactolipids ω3 and ω6 were observed in leaves. Identification of stages with the highest phytochemicals content encourages the consumption of black kale sprouts and young leaves. Our research can support food and pharmaceutical industries for production of health promoting products from black kale.

Topics: Antioxidants; Brassica; Coumaric Acids; Flavonoids; Glucose; Glucosinolates; Imidoesters; Indoles; Mass Spectrometry; Oximes; Phytochemicals; Plant Leaves; Polyphenols; Secondary Metabolism; Seedlings; Seeds; Sulfoxides

Changes in the concentration of the three most abundant glucosinolates were measured in the leaves of perennial wall rocket [Diplotaxis tenuifolia (L.) DC.], and annual garden rocket (Eruca sativa Mill.). HPLC-MS was used to identify glucoraphanin, 4-hydroxyglucobrassin and glucoerucin from perennial wall rocket, and glucoraphanin, glucobrassicin and 4-methoxyglucobrassicin from annual garden rocket. In separate experiments the responses of glucosinolates to harvest number, seasonal conditions, nitrogen supply and post-harvest storage conditions were measured.. For perennial wall rocket, season influenced the concentration of glucoraphanin, which were highest for the spring [379 µg kg(-1) fresh weight (FW)] and summer (317 µg kg(-1) FW) plantings. The concentration of 4-hydroxyglucobrassin was higher in the leaves of first harvest crops. This response was due to this glucosinolate not being detected in the leaves of second harvest crops. Thus, the parent glucosinolate was altered between the first and second harvests in response to the abiotic stresses caused by harvesting. For annual garden rocket, there was an interaction between the harvest number and season for all glucosinolates measured. However, no clear response was observed between these factors. Higher concentrations of glucobrassicin and 4-methoxyglucobrassicin were measured for first harvest leaves when compared to the second harvest. This was due to the absence of detection of these glucosinolates in the leaves of second harvested plants; consequently higher total glucosinolate concentrations were measured for the first harvest winter (1224 µg kg(-1) FW) and summer (864 µg kg(-1) FW) crops.. The concentrations of individual glucosinolates vary greatly over typical pre- and post-harvest commercial conditions. The absence of 4-hydroxyglucobrassin for perennial wall rocket, and glucobrassicin and 4-methoxyglucobrassicin for annual garden rocket between harvests, illustrates that abiotic stress from harvesting has the capacity to alter the types of glucosinolates in leaves. Concentrations do not generally decline during a typical storage period, indicating that the potential benefits of these compounds are not lost during post-harvest storage.

Topics: Brassicaceae; Chromatography, Liquid; Glucose; Glucosinolates; Humans; Imidoesters; Indoles; Mass Spectrometry; Oximes; Plant Leaves; Sulfoxides

The effect of pulsed electric field (PEF) treatment variables (electric field strength and treatment time) on the glucosinolate content of broccoli flowers and stalks was evaluated. Samples were subjected to electric field strengths from 1 to 4 kV cm(-1) and treatment times from 50 to 1000 µs at 5 Hz.. Data fitted significantly (P < 0.0014) the proposed second-order response functions. The results showed that PEF combined treatment conditions of 4 kV cm(-1) for 525 and 1000 µs were optimal to maximize glucosinolate levels in broccoli flowers (ranging from 187.1 to 212.5%) and stalks (ranging from 110.6 to 203.0%) respectively. The predicted values from the developed quadratic polynomial equation were in close agreement with the actual experimental values, with low average mean deviations (E%) ranging from 0.59 to 8.80%.. The use of PEF processing at moderate conditions could be a suitable method to stimulate production of broccoli with high health-promoting glucosinolate content.

Topics: Anticarcinogenic Agents; Brassica; Electric Stimulation; Food Handling; Food, Preserved; Freeze Drying; Glucosinolates; Glycoside Hydrolases; Imidoesters; Indoles; Inflorescence; Models, Biological; Oximes; Plant Proteins; Plant Stems; Secondary Metabolism; Statistics as Topic; Sulfoxides

We profiled and quantified glucosinolates (GSLs), anthocyanins, free amino acids, and vitamin C metabolites in forty-five lines of green and red cabbages. Analysis of these distinct cabbages revealed the presence of 11 GSLs, 13 anthocyanins, 22 free amino acids, and vitamin C. GSL contents were varied amongst the different lines of cabbage. The total GSL content was mean 10.6 μmol/g DW, and sinigrin was the predominant GSL accounted mean 4.0 μmol/g DW (37.7% of the total) followed by glucoraphanin (1.9) and glucobrassicin (2.4). Amongst the 13 anthocyanins, cyanidin 3-(sinapoyl) diglucoside-5-glucoside levels were the highest. The amounts of total free amino acids in green cabbage lines ranged 365.9 mg/100g fresh weight (FW) to 1089.1mg/100g FW. Vitamin C levels were much higher in red cabbage line (129.9 mg/100g FW). Thus, the amounts of GSLs, anthocyanins, free amino acids, and vitamin C varied widely, and the variations in these compounds between the lines of cabbage were significant.

Topics: Amino Acids; Anthocyanins; Ascorbic Acid; Brassica; Food Analysis; GABA Agents; Glucosinolates; Imidoesters; Indoles; Oximes; Sulfoxides; Vitamins

Methyl jasmonate (MeJA) treatment can significantly increase glucosinolate (GS) concentrations in Brassica vegetables and potentially enhance anticancer bioactivity. Although MeJA treatment may promote ethylene biosynthesis, which can be detrimental to postharvest quality, there are no previous reports of its effect on cauliflower postharvest quality. To address this, cauliflower curds in field plots were sprayed with either 0.1 % Triton X-100 (control) or 500 μM MeJA solutions four days prior to harvest, then stored at 4 °C. Tissue subsamples were collected after 0, 10, 20, and 30 days of postharvest storage and assayed for visual color change, ethylene production, GS concentrations, and extract quinone reductase inductive activity. MeJA treatment increased curd GS concentrations of glucoraphanin, glucobrassicin, and neoglucobrassicin by 1.5, 2.4, and 4.6-fold over controls, respectively. MeJA treated cauliflower showed significantly higher quinone reductase activity, a biomarker for anticancer bioactivity, without reducing visual color and postharvest quality for 10 days at 4 °C storage.

Topics: Acetates; Anticarcinogenic Agents; Brassica; Color; Cyclopentanes; Ethylenes; Food Handling; Food Quality; Glucosinolates; Imidoesters; Indoles; NAD(P)H Dehydrogenase (Quinone); Octoxynol; Oximes; Oxylipins; Plant Extracts; Sulfoxides

Epidemiological and mechanistic studies show health-promoting effects of glucosinolates and their breakdown products. In literature, differences in non-enzymatic glucosinolate degradation rates during food processing between different vegetables are described, which provide the basis for studying the genetic effects of this trait and breeding vegetables with high glucosinolate retention during food processing. Non-enzymatic glucosinolate degradation, induced by heat, was studied in a publicly available Brassica oleracea doubled haploid population. Data were modeled to obtain degradation rate constants that were used as phenotypic traits to perform quantitative trait loci (QTL) mapping. Glucosinolate degradation rate constants were determined for five aliphatic and two indolic glucosinolates. Degradation rates were independent of the initial glucosinolate concentration. Two QTL were identified for the degradation rate of the indolic glucobrassicin and one QTL for the degradation of the aliphatic glucoraphanin, which co-localized with one of the QTL for glucobrassicin. Factors within the plant matrix might influence the degradation of different glucosinolates in different genotypes. In addition to genotypic effects, we demonstrated that growing conditions influenced glucosinolate degradation as well. The study identified QTL for glucosinolate degradation, giving the opportunity to breed vegetables with a high retention of glucosinolates during food processing, although the underlying mechanisms remain unknown.

Topics: Brassica; Breeding; Chromosome Mapping; Food Handling; Genetic Variation; Genotype; Glucosinolates; Haploidy; Imidoesters; Indoles; Models, Theoretical; Oximes; Phenotype; Plant Leaves; Quantitative Trait Loci; Seeds; Sulfoxides; Temperature

Glucosinolates are multi-functional plant secondary metabolites which play a vital role in plant defence and are, as dietary compounds, important to human health and livestock well-being. Knowledge of the tissue-specific regulation of their biosynthesis and accumulation is essential for plant breeding programs. Here, we report that in Arabidopsis thaliana, glucosinolates are accumulated differentially in specific cells of reproductive organs. Using matrix-assisted laser desorption/ionization (MALDI) mass spectrometry imaging (MSI), distribution patterns of three selected compounds, 4-methylsulfinylbutyl (glucoraphanin), indol-3-ylmethyl (glucobrassicin), and 4-benzoyloxybutyl glucosinolates, were mapped in the tissues of whole flower buds, sepals and siliques. The results show that tissue localization patterns of aliphatic glucosinolate glucoraphanin and 4-benzoyloxybutyl glucosinolate were similar, but indole glucosinolate glucobrassicin had different localisation, indicating a possible difference in function. The high resolution images obtained by a complementary approach, cryo-SEM Energy Dispersive X-ray analysis (cryo-SEM-EDX), confirmed increased concentration of sulphur in areas with elevated amounts of glucosinolates, and allowed identifying the cell types implicated in accumulation of glucosinolates. High concentration of sulphur was found in S-cells adjacent to the phloem in pedicels and siliques, indicating the presence of glucosinolates. Moreover, both MALDI MSI and cryo-SEM-EDX analyses indicated accumulation of glucosinolates in cells on the outer surface of the sepals, suggesting that a layer of glucosinolate-accumulating epidermal cells protects the whole of the developing flower, in addition to the S-cells, which protect the phloem. This research demonstrates the high potential of MALDI MSI for understanding the cell-specific compartmentation of plant metabolites and its regulation.

Topics: Arabidopsis; Flowers; Glucosinolates; Imidoesters; Indoles; Microscopy, Electron, Scanning; Oximes; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Sulfoxides; Sulfur

The potential of visible-near-infrared spectroscopy to determine selected individual and total glucosinolates in broccoli has been evaluated. Modified partial least-squares regression was used to develop quantitative models to predict glucosinolate contents. Both the whole spectrum and different spectral regions were separately evaluated to develop the quantitative models; in all cases the best results were obtained using the near-infrared zone between 2000 and 2498 nm. These models have been externally validated for the screening of glucoraphanin, glucobrassicin, 4-methoxyglucobrassicin, neoglucobrassicin, and total glucosinolates contents. In addition, discriminant partial least-squares was used to distinguish between two possible broccoli cultivars and showed a high degree of accuracy. In the case of the qualitative analysis, best results were obtained using the whole spectrum (i.e., 400-2498 nm) with a correct classification rate of 100% in external validation being obtained.

Topics: Brassica; Feasibility Studies; Glucosinolates; Imidoesters; Indoles; Least-Squares Analysis; Oximes; Phytochemicals; Reproducibility of Results; Spectroscopy, Near-Infrared; Sulfoxides

Total aliphatic and indole glucosinolates, phenolic compounds (flavonoids and hydroxycinnamoyl derivatives), and vitamin C contents were evaluated in freshly harvested broccoli (Brassica oleracea L., var. italica, cv. Marathon) inflorescences. These were film-wrapped and stored for 7 days at 1 degrees C to simulate a maximum period of commercial transport and distribution. After cold storage, inflorescences were kept for 3 days at 15 degrees C to simulate a retail sale period. For wrapping, low-density polyethylene (LDPE) of 11 microm thickness was used. Gas composition was about 17% O(2) and 2% CO(2) during cold storage and about 16% O(2) and 3-4% CO(2) during shelf life within packages. The predominant glucosinolates were 4-methylsulfinylbutyl-glucosinolate (glucoraphanin), 3-indolylmethyl-glucosinolate (glucobrassicin), and 1-methoxy-3-indolylmethyl-glucosinolate (neoglucobrassicin). The predominant hydroxycinnamoyl derivatives were identified as 1,2,2'-trisinapoylgentiobiose, 1,2-diferuloylgentiobiose, 1,2'-disinapoyl-2-feruloylgentiobiose, and 3-O-caffeoyl-quinic (neochlorogenic acid). Results showed major losses at the end of both periods, in comparison with broccoli at harvest. Thus, the respective losses, at the end of cold storage and retail periods, were 71-80% of total glucosinolates, 62-59% of total flavonoids, 51-44% of sinapic acid derivatives, and 73-74% caffeoyl-quinic acid derivatives. Slight differences in all compound concentrations between storage and retail sale periods were detected. Distribution and retail periods had minimal effects on vitamin C. Weight loss was monitored at the end of both periods.

Topics: Ascorbic Acid; Brassica; Carbon Dioxide; Cold Temperature; Coumaric Acids; Flavonoids; Food Packaging; Food Preservation; Glucose; Glucosinolates; Health Promotion; Imidoesters; Indoles; Oximes; Oxygen; Phenols; Plant Structures; Sulfoxides; Time Factors; Transportation