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Glucosinolate composition and anti-cancer potential of daikon and radish sprouts
Abstract
Daikon and radish sprouts contain high levels of glucoraphenin, a glucosinolate which hydrolyses to form sulphoraphene. Sulphoraphene, like sulphoraphane from broccoli, is a potent inducer of phase 2 detoxification enzymes and consequently has potential anti-cancer action. Unlike broccoli however, daikon and radish do not possess epithiospecifier protein, a protein that inhibits conversion of glucosinolates to isothiocyanates, and consequently they may represent more suitable sources of phyto-chemicals with anti-cancer potential. Concentrations of glucoraphenin were highest in the seed, declining exponentially with sprout development. The rate of decline was observed to vary considerably between varieties of daikon and radish, with some varieties maintaining significantly high levels of glucoraphenin. Varieties maintaining a high level of glucoraphenin included 'Cherry Belle' and 'French Breakfast'.
... The large amount of glucoraphanin contained in the three broccoli cultivars studied in the present work should be highlighted since glucoraphanin is the precursor of sulfurophane that has been recognised as the major inducer of anticarcinogenic protective enzymes in broccoli (Fenwick et al., 1983). On the other hand, glucoraphenin was found to be the dominant GLS in the two radish cultivars studied here, in accordance with results reported by Zielinski, Piskula, Michalska, and Kozlowska (2007), Ciska et al. (2008) andO'Hare, Wong, andForce (2008). Radish seeds cv. ...
... The large amount of glucoraphanin contained in the three broccoli cultivars studied in the present work should be highlighted since glucoraphanin is the precursor of sulfurophane that has been recognised as the major inducer of anticarcinogenic protective enzymes in broccoli (Fenwick et al., 1983). On the other hand, glucoraphenin was found to be the dominant GLS in the two radish cultivars studied here, in accordance with results reported by Zielinski, Piskula, Michalska, and Kozlowska (2007), Ciska et al. (2008) andO'Hare, Wong, andForce (2008). Radish seeds cv. ...
... Radish seeds cv. Rebel presented a high amount of glucoraphenin that has an additional effect on health promotion, since the production of its known ITC sulforaphene has been particularly potent in the ability to induce the phase II enzyme quinone reductase (Lee & Lee, 2006;O'Hare et al., 2008;Posner et al., 1994). ...
Optimisation of the germination process of different cultivars of broccoli (Brassica oleracea var. italica cv. Lucky, cv. Tiburon and cv. Belstar) and radish (Raphanus sativus cv. Rebel and cv. Bolide) seeds in relation to the content of glucosinolates (GLS), vitamin C and total antioxidant capacity was carried out in order to maximise the health-promoting properties of Brassica sprouts. The content of total and individual GLS varied between species, among cultivars, and germination time. Glucoraphanin in broccoli and glucoraphenin in radish were the predominant GLS in raw seeds (61–77 and 63–129 μmol/g DM, respectively) and, although their content decreased during germination, they were maintained in rather large proportions in sprouts. Vitamin C was not detected in raw seeds and its content increased sharply in broccoli and radish sprouts (162–350 and 84–113 mg/100 g DM, respectively). Raw brassica seeds are an excellent source of antioxidant capacity (64–90 and 103–162 μmol Trolox/g DM in broccoli and radish, respectively) and germination led to a sharp increase. Germination of broccoli cv. Belstar and radish cv. Rebel for 4 days provided the largest glucoraphanin and glucoraphenin content, respectively, and also brought about large amounts of vitamin C and antioxidant capacity.
... makes them good candidates for landscape design [6]. Cardamine flexuosa has been shown to exhibit anticancer properties due to their high content of glucosinolates which hydrolyze to form bioactive products such as isothiocyanates [7]. ...
... Brassica rapa chinensis L locally known as Petchay and also known as Pak choi is a popular vegetable in the Philippines. It belongs to the family Brassicaceae which exhibit anti-cancer properties due to their high content of glucosinolates which hydrolyze to form the bioactive isothiocyanates 1,2 . An earlier study on Pak choi (Brassica campestris L. ssp chinensis var. ...
Brassica rapa chinensis L. and Brassica rapa var. parachinensis (Baily) Hanelt were studied for their chemical constituents. The dichloromethane extracts of the leaves of Brassica chinensis L. afforded β-sitosteryl-3β-glucopyranoside-6-O-fatty acid esters (1), β-sitosterol (2), chlorophyll a (3) and phytyl fatty acid esters (4), while the leaves of Brassica rapa var. parachinensis (Baily) Hanelt yielded 4, monogalactosyl diacylglycerol (5) and lutein (6). The structures of 1-6 were identified by comparison of their NMR data with those reported in the literature.Brassica rapa chinensis L. and Brassica rapa var. parachinensis (Baily) Hanelt were studied for their chemical constituents. The dichloromethane extracts of the leaves of Brassica chinensis L. afforded β-sitosteryl-3β-glucopyranoside-6-O-fatty acid esters (1), β-sitosterol (2), chlorophyll a (3) and phytyl fatty acid esters (4), while the leaves of Brassica rapa var. parachinensis (Baily) Hanelt yielded 4, monogalactosyl diacylglycerol (5) and lutein (6). The structures of 1-6 were identified by comparison of their NMR data with those reported in the literature.
... Both total level and profile of glucosinolates and their hydrolysis products, vary between Brassica species and cultivars (Cartea et al., 2008; Castro et al., 2004; Charron et al., 2005; Fahey et al., 2001; Mithen, 2000; Nakamura et al., 2008; O'Hare et al., 2008; Velasco et al., 2008). Meyer and Adam (2008) found glucoraphanin, glucobrassicin and neo-glucobrassicin to be the predominant glucosinolates in broccoli. ...
As compared to mature vegetables, radish and mustard sprouts have superior nutritional and phytochemical profiles. Depending on the cultivar, species, environmental factors, and germination time, radish and mustard seeds of various kinds had a 2–10 times increase in phytochemical profiles. Mustard and radish both contain a variety of healing and health-promoting substances. The three main bioactive components are glucosinolates, sulforaphane, and isothiocyanates. The glucosinolates are bioactive compounds that are hydrolyzed into a number of biologically active products i.e., indoles and isothiocyanates, in the presence of the enzyme myrosinase by the action of the gut microflora upon human ingestion. Bioactive compounds present in these possess significant biological activities due to their anti-inflammatory, anticancer, and antioxidant properties. Additionally, sulforaphane, which is generated from the anti-cancer compound glucoraphenin and found in radish sprouts, has recently been discovered and investigated. These sprouts also include other modest yet significant phytochemicals, the majority of which are phenolic compounds, or hydroxycinnamic acid derivatives (sinapic acids or chlorogenic acids). However, their utilization is still confined to its freshly cut salads. There is still a wide area that remains unexploited for their utilization in value-added products. Considering the importance of radish and mustard sprouts, this chapter widely explores the potential health benefits allied with their consumption, their processing conditions, nutritional profile, and their microbiological safety. Mustard and radish sprouts are safe foods from the perspective of their microbiological and phytochemical content. Additionally, this study, makes a scientific contribution to the field of food safety of significant interest for sprout consumers and producers.
Brassicaceae is one of the few plant families with the ability to incorporate the essential trace element selenium (Se) into organic compounds, and the vegetables are claimed to have a number of human health benefits based on both Se and glucosinolate content. We investigated the effect of Se addition on the nutrient composition of broccoli, purple radish and green radish sprouts and develop an efficient growing method for producing high concentration Se radish sprouts that does not impact the glucosinolate content and has little seleniferous waste.
The concentration of Se in sprouts increased exponentially with time in the presence of high Se supply (9.2 μmol Se g⁻¹ seed). At lower rates of Se supply (≤2.5 μg Se g⁻¹ seed) sprouts containing a target Se concentration were produced according to the linear relationship y = 0.91x, where y is the target Se concentration in μg Se g⁻¹ FW, and x is the concentration of sodium selenate in water added at 8.3 mL of water g⁻¹ dry seed. Glucosinolate profiles differed between broccoli and radish but the total glucosinolate concentration of the sprouts was unaffected by Se addition. Radish was more suitable than broccoli for producing sprouts high in both glucosinolates and Se.
Flavin monooxygenase (FMO) is one of the most important enzymes involved in glucosinolate biosynthesis. In this study, the full length of FMO gene (RsFMOgs-ox1) encoding a putative FMO protein composed of 450 amino acids was successfully cloned using the RACE-PCR method. The amino acid sequence of RsFMOgs-ox1 has high similarities of 92% and 83% with BrFMOgs-ox1 and AtFMOgs-ox1,2,3, respectively, and the gene structure of FMOgs-ox1 is similar to its plant homologues. Quantitative (qPCR) analysis revealed that RsFMOgs-ox1 was highly expressed during early seedling development. In mature radish, the highest expression was observed in the leaves, while the lowest transcript was evident in the root. The expression of RsFMOgs-ox1 was also regulated by wounding, notably 1 day after treatment. Subcellular localization in Arabidopsis showed that RsFMOgs-ox1 was localized in the cytoplasm and nuclei. This study allows us to understand something about RsFMOgs-ox1 function in glucosinolate biosynthesis.
Red radish seeds were irradiated at doses up to 8 kGy using electron beam (e-beam) and gamma ray (γ-ray). The seed viability and functional properties (carotenoid, chlorophyll, ascorbic acid, and total phenol) of sprouts grown from these irradiated seeds were evaluated. High germination percentage (≥97%) was observed in seeds irradiated at ≤5 kGy, but the yield ratio and sprout length significantly decreased with increased irradiation dose. Irradiation at ≥6 kGy resulted in curling of the sprout roots. Sprouting enhanced the functional properties of red radish seeds as indicated by the increased carotenoid, chlorophyll, ascorbic acid, and total phenol contents during germination. However, radiation treatment hampered the growth of seeds resulting in underdeveloped sprouts with decreased carotenoid, chlorophyll, ascorbic acid, and total phenol contents. In general, e-beam and γ-ray irradiation of red radish seeds showed similar effects on the seed viability and functional properties of sprouts. Postharvest storage reduced the functional quality of sprouts.
Chemical investigation of the whole plant of Cardamine flexuosa led to the isolation of β-sitosterol (1), stigmasterol (2), lutein (3), unsaturated triglycerides (4) and the essential fatty acids, linoleic acid (5) and linolenic acid (6). The structures of 1-6 were identified by comparison of their 1H NMR data with those reported in the literature.
The antibacterial effects of seed decontamination during presoaking before sprouting as an intervention step for eliminating foodborne pathogens on red radish seeds were evaluated. The effect of seed decontamination on seed germination rate was also evaluated. Red radish seeds were inoculated (at a level of 3 to 4 log CFU/g) with Listeria monocytogenes ATCC 19111 and decontaminated with 20,000 ppm calcium hypochlorite, 50 and 100 ppm chlorinated water, acidic electrolyzed water, low-alkaline electrolyzed water, and ozonated water for 6 hours. The control seeds were immersed in distilled water. The germination rate was measured on each treatment for 48 hours. Treatments with 20,000 ppm calcium hypochlorite, acidic and low-alkaline electrolyzed water were more effective than treatments with chlorinated water and ozonated water. Immersion in 20,000 ppm calcium hypochlorite resulted in the largest microbial reduction (more than 3 logs). Treatments with acidic and low-alkaline electrolyzed water reduced APC by 3 logs and L. monocytogenes counts by 2 logs. After sprouting, APC and L. monocytogenes counts on seeds treated with 20,000 ppm calcium hypochlorite, acidic and low-alkaline electrolyzed water were significantly lower than the control. The germination rate ranged from 93.5% to 97.7% except for 20,000 ppm calcium hypochlorite (from 82.3% to 84.8%) after 48 hours. Although the treatments tested in this study will not eliminate L. monocytogenes on inoculated red radish seeds, the results show that rapid growth of surviving cells during sprouting could be prevented if red radish seeds are given a presoak treatment used in combination with a disinfectant treatment of irrigation water.
Sulforaphene, an isothiocyanate, converted from glucoraphenin in radish, and plays an important role as plant defensive compounds and cancer-preventing agents for humans. In this study, the optimized HPLC method was used to detect the sulforaphene content of fleshy roots among 93 accessions of radish germplasm, and the distribution of sulforaphene content in different origins and different types of radish germplasm was analyzed. The results indicated that the content of sulforaphene among the gemplasm was significantly different. The content of sulforaphene ranged from 34.445 mg/kgDW to 1446.9 mg/kgDW. The highest content is almost 42 times more than the lowest one. The average content of the red skin white flesh and green skin green flesh radish germplasm was high. The average sulforaphene content of the radish germplasm in the eastern China was higher than those in other regions. Two radish germplasm of high sulforaphene content were screened out, which are good materials for further studies.
The dichloromethane extracts of the leaves of Brassica oleracea var capitata f. rubra L (red cabbage) and Brassica oleracea L (green/white cabbage) and the stem of Brassica oleracea L var. italic (broccoli) afforded β-sitosterol (1) and unsaturated triglycerides (2). The red cabbage also afforded stigmasterol (3), while the green/white cabbage and broccoli stem also yielded the essential fatty acid, linoleic acid (4). Brassica juncea (mustard) leaves and Raphanus sativus (radish) roots afforded 1, and the essential fatty acids 4 and α-linolenic acid (6). Mustard leaves also yielded trilinolenin (5), lutein (7) and β-carotene (8), while radish roots also afforded 2. These compounds were reported to exhibit anticancer properties.
The activity of a methanol extract of radish sprouts for the induction of nicotinamide adenine dinucleotide (phosphate) NAD(P)H/quinone reductase (QR), which plays critical roles in protection against chemical carcinogens and other toxic xenobiotics, was examined in murine Hepa1c1c7 cells. The methanol extract induced QR activity in a dose-dependent manner in the concentration range of 0.2 to 1.6 mg/mL with a maximum of a 3.5-fold increase in induction. The induction of QR by the extract was regulated at the transcriptional level. Using a Western blotting analysis and Ah-receptor-defective mutant of Hepa1c1c7 cells (BPrc1 cells), the extracts at a concentration of 0.8 mg/mL or lower was found to be a monofunctional inducer and caused no elevation in cytochrome P-450 level that may activate carcinogens. The dichloromethane (CH2Cl2) fraction of the extract showed the highest induction potency while the other fractions were less potent. These results indicate that radish sprouts can be regarded as a safe and promising new dietary source for decreasing the risk of developing cancer.
Allylglucosinolate is converted to 1-cyano-2,3-epithiopropane by interaction of the thioglucoside glucohydrolase and epithiospecifier protein from several genera: Brassica, Crambe, Armoracia and Sinapis. The interactions occur across genetic lines, indicating non-specific requirements for epithiospecifier protein and thioglucoside glucohydrolase.
Ion-pair and hydrophilic interaction chromatographies are considered to be complementary methods of choice for analyzing intact glucosinolates from broccoli. Ion-pair chromatography resolves non-polar glucosinolates, such as those containing indole moieties, while hydrophilic interaction chromatography is superior for separating polar glucosinolates, such as glucoraphanin and glucoiberin. Reversed-phase separations using hydrophilic endcapped C18-bonded silica and a 50 mM ammonium acetate-methanol gradient mobile phase resolve both polar and non-polar glucosinolates negating the need for switching columns.