Comparison of bioactive phytochemical content and release of isothiocyanates in selected brassica sprouts

The consumption of brassica sprouts as raw vegetables provides a fair amount of glucosinolates (GLs) and active plant myrosinase, which enables the breakdown of GLs into health-promoting isothiocyanates (ITCs). This study reports the determination of the main constituents related to human health found in edible sprouts of two Brassica oleracea varieties, broccoli and Tuscan black kale, and two Raphanus sativus varieties, Daikon and Sango. Radish sprouts exhibited the highest ability to produce ITCs, with Daikon showing the greatest level of conversion of GLs into bioactive ITCs (96.5%), followed by Sango (90.0%). Tuscan black kale gave a value of 68.5%, whereas broccoli displayed the lowest with 18.7%. ITCs were not the exclusive GL breakdown products in the two B. oleracea varieties, since nitriles were also produced, thus accounting for the lower conversion observed. Measuring the release of plant ITCs is a valuable tool in predicting the potential level of exposure to these bioactive compounds after the consumption of raw brassica sprouts.     

Glucosinolate levels in cotyledons of mustard,Brassica juncea L. and rape,B. napus L. do not determine feeding rates of flea beetle,Phyllotreta cruciferae (Goeze)

Sinigrin (allyl glucosinolate), the major glucosinolate in the cotyledons ofBrassica juncea cv. Cutlass, occurred in the highest concentration and amount at seedling emergence and declined during growth. Glucobrassicin (3-indolylmethyl glucosinolate), the major glucosinolate in the cotyledons ofB. napus cv. Westar, occurred in the lowest concentration and amount at seedling emergence. The amount of glucobrassicin per cotyledon pair increased about fourfold during 14 days of growth, but its concentration remained relatively unchanged because of dilution by increasing cotyledon biomass. These different glucosinolate profiles indicate a different metabolic control and different biological function for sinigrin and glucobrassicin. The flea beetle,Phyllotreta cruciferae Goeze, does not discriminate between cotyledons having sinigrin or glucobrassicin since the two crucifers were fed upon equally in choice tests. Restricting the concentration of sulfur in the nutrient medium accelerated the decline of sinigrin inB. juncea cv. Cutlass but did not alter the feeding rate ofP. cruciferae compared to controls. Sulfur restriction reduced glucobrassicin inB. napus cv. Westar to undetectable levels and somewhat reduced the feeding rate of P.Cruciferae. Nevertheless,P. cruciferae still fed actively on cotyledons ofB. napus cv. Westar depleted of glucosinolates and severely damaged many of them. Since glucosinolate type and concentration had little effect on feeding response, reduction or elimination of foliar glucosinolates alone would not seem a useful strategy for protecting seedlings of these two crucifers from flea beetle damage.     

Variation of glucosinolates in vegetable crops of Brassica rapa L. ssp. pekinensis

Glucosinolates of Chinese cabbage (Brassica rapa L. ssp. pekinensis) from Korea were characterised to determine the total glucosinolate content and the diversity amongst glucosinolates; 24 varieties were analysed. The profiles of 14 glucosinolates identified from the leaves were subjected to principal component analysis (PCA) to evaluate the differences among varieties. The Kori, Sandun and e-Norang varieties separated from the others based on glucosinolate concentration. Genetically modified Chinese cabbage containing the bar gene could not be separated from non-genetically modified varieties. Glucobrassicanapin, 4-methoxyglucobrassicin, gluconapin and glucobrassicin in Chinese cabbage were confirmed as the main glucosinolate compounds. The Kori, Sandun and e-Norang varieties appear to be good candidates for future breeding programmes since they have a high glucosinolate content. The presence of indolic glucosinolates in all varieties should be studied more extensively because they are the precursor of indole-3-carbinol, a potent cancer chemopreventive agent.     

Anti-Nutritional Components, Fibre, Sinapine and Glucosinolate Content, in Australian Canola (Brassica napus L.) Meal

Canola meal is highly regarded as a component of animal feed with a high protein content and a desirable amino acid profile. The presence of some components, in particular glucosinolates, sinapine and fibre, affects the value of the meal and reduces the amount that can be used in animal feed formulations. Glucosinolates in traditional cultivars (rapeseed) had very high amounts and this severely limited the usefulness of the meal. Canola breeding programs have successfully reduced glucosinolate content to trace amounts. However sinapine remains at levels sufficiently high to cause problems, particularly in poultry feed. The relatively high fibre level in canola also reduces the value of the product for animal feed. This study has determined the level of sinapine, glucosinolates and fibre in current cultivars of canola in Australia to illustrate advances made by breeding programs and limitations which still remain to raise the usefulness of a potentially valuable feedstock. Although glucosinolate levels in meal were shown to have been reduced to 11 μmol/g in some cases, sinapine remained at traditional levels of about 12–15 g/kg and neutral detergent fibre levels were about 30–40%. These issues are important priorities for canola breeders.     

Genotypic variation of glucosinolates in broccoli (Brassica oleracea var. italica) florets from China

Five main cultivars from China and 143 parent materials grown in a greenhouse were used to investigate the glucosinolates in broccoli florets. Eight aliphatic glucosinolates, four indole glucosinolates, and one aromatic glucosinolate were identified and quantified using high-performance liquid chromatography (HPLC). The results showed that glucoraphanin, glucobrassicin, 4-methoxyglucobrassicin and neoglucobrassicin were present in all samples. However, the predominant type of glucosinolate was different among pure lines. The anti-cancer glucoraphanin concentration ranged from 0.06 to 24.17 μmol/g in pure lines and from 1.57 to 5.95 μmol/g in commercial cultivars. The progoitrin concentration in commercial cultivars varied from 1.77 to 6.07 μmol/g with a mean value of 3.20 μmol/g. Significant variations were observed in the concentration of individual glucosinolates and in each class of glucosinolates among broccoli populations. Dozens of specific lines with altered glucosinolate profiles, as well as ten good candidates for breeding high-chemoprotective glucosinolate cultivars, were obtained according to the putative glucosinolate pathway in broccoli.     

Se improves indole glucosinolate hydrolysis products content, Se-methylselenocysteine content, antioxidant capacity and potential anti-inflammatory properties of sauerkraut

Selenium (Se) has a well-known role in prevention of chronic diseases associated with oxidative stress and inflammation. The objective was to produce Se-enriched sauerkraut and to study the effect of selenite addition on indole glucosinolate hydrolysis products, vitamin C, Se biotransformation and microbial quality. The antioxidant activity of sauerkraut and its ability to inhibit NO production in LPS-induced macrophages were also examined. White cabbage was naturally fermented with 0.3 mg of Na₂SeO₃/kg fresh cabbage (NFSe) or without Se addition (NF). Total Se content reached up to 1.29 μg/g d.m. (0.11 μg/g f.m.). Selenomethylselenocysteine was the major Se form found in NFSe cabbage. Se addition caused a slight reduction of ascorbigen (6%) and vitamin C (5%) contents in sauerkraut (P ? 0.05); however, lactic acid bacteria increased (3%), and the formations of indole-3-carbinol and indole-3-acetonitrile were markedly enhanced (74% and 13%, respectively). NFSe cabbage extracts showed higher (P ? 0.05) antioxidant activity (163 μmol trolox/g d.m.) and inhibition of NO production in LPS-induced macrophages (IC₅₀ = 44.0 μg/ml) than did NF cabbage extracts. Consequently, Se-enriched sauerkraut can be considered as a health-promoting food.     

The thymol method for glucosinolate determination

This paper details experiments aimed at optimising the conditions for the determination of glucosinolates in rapeseed (Brassica napus L) using the colorimetric thymol procedure. Glucose could not be substituted for sinigrin when preparing a standard curve for glucosinolate determination unless a correction factor was employed. The value of this factor was found to depend on the concentration of sulphuric acid. Although the coloured complexes formed between thymol and either glucose or sinigrin were found to be unstable at 100°C, the sinigrin/ glucose colour ratio remained relatively constant for incubation times from 40 to 60 min. It was found necessary to increase the amount of thymol present to a final value of 0.23% to ensure complete reaction of glucosinolates. The revised method can be employed successfully for the analysis of glucosinolates in both seed and meal.     

Comparison of HPLC and GLC methodologies for determination of glucosinolates using reference material

 The reference material rapeseed of known glucosinolate composition, was analysed by HPLC and GLC and two commercially available glucosinolates (glucotropaeolin and sinigrin) were used as internal standards. The HPLC method enabled determination of 11 different glucosinolates (as desulphoglucosinolates) that occur in the rapeseed. Only seven glucosinolates (as trimethylsilylated desulphoglucosinolates) were separated by GLC. The latter method did not allow the determination of methylsulphinylalkyl glucosinolates (glucoiberin, glucoraphanin and glucoallysin) and did not separate optical isomers of 2-hydroxy-3-butenyl glucosinolate (progoitrin and epi-progoitrin). Statistical evaluation of data (t-test, F-test) revealed no significant differences between the tested methods at the 95% confidence level. The advantages and disadvantages of both widely used chromatographic methods are discussed. Received: 26 May 1997 / Revised version: 11 July 1997     

A new antimicrobial glucosinolate autolysis product, 4-isothiocyanatobutanoic acid,from the diffuse wallflower (Erysimum diffusum): Methyl 4-isothiocyanatobutanoate,a long unrecognized artifact of the isolation procedure?

A GC–MS analysis of Erysimum diffusum Ehrh. (Brassicaceae) glucosinolate autolysis products led to the identification of a new mustard oil constituent – 4-isothiocyanatobutanoic acid. The identity of the new glucosinolate breakdown product was confirmed by means of co-injection of the synthetic compound in the GC with the root autolysate and derivatization reaction to the well known methyl ester. Methyl ester of this acid was long believed to be a genuine glucosinolate hydrolysis product but we now provide evidence that it could be an artifact of the isolation procedure. 4-Isothiocyanatobutanoic acid was assayed for antimicrobial activity and demonstrated significant inhibitory (10–220 μg/ml) and microbicidal (10–1175 μg/ml) activity against important human pathogens.     

加压条件下油菜籽中硫苷非酶降解性质的研究

研究总结了加压条件下油菜籽中硫苷非酶降解性质，筛选出促进硫苷非酶降解反应的化学试剂，采用响应曲面法分析，优化硫降解条件，成功地使硫苷非酶降解率在１５～２５ｍｉｎ内达到９０％以上，且避免了大量腈类化合物的生成。