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Renato Iori - One of the best experts on this subject based on the ideXlab platform.
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acylated anthocyanins from sprouts of Raphanus sativus cv sango isolation structure elucidation and antioxidant activity
Food Chemistry, 2015Co-Authors: Riccardo Matera, Renato Iori, Simone Gabbanini, Serena Berretti, Riccardo Amorati, Gina Rosalinda De Nicola, Luca ValgimigliAbstract:Abstract Little is known on structure–activity relationships of antioxidant anthocyanins. Raphanus sativus cv Sango sprouts are among the richest sources (270 mg/100 g fresh weight). We isolated from sprouts’ juice 9 acylated anthocyanins, including 4 new compounds. All comprise a cyanidin core bearing 3–4 glucose units, multiply acylated with malonic and phenolic acids (ferulic and sinapic). All compounds were equally effective in inhibiting the autoxidation of linoleic acid in aqueous micelles, with rate constant for trapping peroxyl radicals kinh = (3.8 ± 0.7) × 104 M–1 s–1 at 37 °C. In acetonitrile solution kinh varied with acylation: (0.9–2.1) × 105 M–1 s–1 at 30 °C. Each molecule trapped a number n of peroxyl radicals ranging from 4 to 7. Anthocyanins bearing sinapic acid were more effective than those bearing the ferulic moiety. Under identical settings, deacylated cyanin, ferulic and sinapic acids had kinh of 0.4 × 105, 0.3 × 105 and 1.6 × 105 M–1 s–1 respectively, with n ranging 2–3. Results show the major role of acylation on antioxidant performance.
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kaiware daikon Raphanus sativus l extract a naturally multipotent chemopreventive agent
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Jessica Barillari, Renato Iori, Alessio Papi, Marina Orlandi, G Bartolini, Simone Gabbanini, Gian Franco Pedulli, Luca ValgimigliAbstract:Brassica vegetables are attracting major attention as healthy foods because of their content of glucosinolates (GLs) that release the corresponding isothiocyanates (ITCs) upon myrosinase hydrolysis. A number of studies have so far documented the chemopreventive properties of some ITCs. On the other hand, single nutrients detached from the food itself risk being somewhat “reductive”, since plants contain several classes of compounds endowed with a polyhedral mechanism of action. Our recent finding that 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) and 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC), released by the GLs purified from Japanese (Kaiware) Daikon (Raphanus sativus L.) seeds and sprouts, had selective cytotoxic/apoptotic activity on three human colon carcinoma cell lines prompted further research on the potential chemopreventive role of a standardized Kaiware Daikon extract (KDE), containing 10.5% w/w GRH and 3.8% w/w GRE, compared to its isolated components. KDE administered in combinatio...
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cytotoxic and antioxidant activity of 4 methylthio 3 butenyl isothiocyanate from Raphanus sativus l kaiware daikon sprouts
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Alessio Papi, Jessica Barillari, Renato Iori, Marina Orlandi, G Bartolini, Gian Franco Pedulli, M Paolini, Fiammetta Ferroni, Maria Grazia Fumo, Luca ValgimigliAbstract:There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase II detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulf...
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antioxidant and choleretic properties of Raphanus sativus l sprout kaiware daikon extract
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Jessica Barillari, E Speroni, M C Guerra, Rinaldo Cervellati, Stefano Costa, And Aneli Utan, Renato IoriAbstract:Brassica vegetables and glucosinolates contained therein are supposed to reduce the risk of cancer and to possess health-promoting properties. The benefits of a Brassica-based diet may be particularly expressed by eating sprouts, in which the glucosinolate content is higher than in mature vegetables. With this in mind, a first objective of this study was to evaluate the antioxidant properties of radish (Raphanus sativus L.) sprouts (Kaiware Daikon) extract (KDE), in which the glucosinolate glucoraphasatin (GRH), showing some antioxidant activity, is present at 10.5% w/w. The contribution of GRH to KDE's antioxidant activity was considered in two chemical assays (Trolox equivalent antioxidant capacity and Briggs−Rauscher methods). The total phenol assay by Folin−Ciocalteu reagent was performed to quantify the reducing capacity of KDE. Finally, on the basis of the putative choleretic properties of antioxidant plant extracts, the effect on the bile flow of KDE administration was investigated in an animal exp...
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isolation of 4 methylthio 3 butenyl glucosinolate from Raphanus sativus sprouts kaiware daikon and its redox properties
Journal of Agricultural and Food Chemistry, 2005Co-Authors: Jessica Barillari, Rinaldo Cervellati, M Paolini, Arnaud Tatibouet, Patrick Rollin, Renato IoriAbstract:The most promising among glucosinolates (GLs) are those bearing in their aglycon an extra sulfur function, such as glucoraphasatin (4-methylthio-3-butenyl GL; GRH) and glucoraphenin (4-methylsulfinyl-3-butenyl GL; GRE). The GRE/GRH redox couple is typically met among secondary metabolites of Raphanus sativus L. and, whereas GRE prevails in seeds, GRH is the major GL in full-grown roots. During the 10 days of sprouting of R. sativus seeds, the GRE and GRH contents were determined according to the Eurpean Union official method (ISO 9167-1). In comparison to the seeds, the GRE content in sprouts decreased from about 90 to about 12 μmol g-1 of dry weight (dw), whereas a 25-fold increasefrom about 3 to 76 μmol g-1 of dwof the GRH content was measured. An efficient pure GRH gram-scale production process from R. sativus (kaiware daikon) sprouts resulted in significant yield improvement of up to 2.2% (dw basis). The reaction of GRH with both H2O2 and ABTS•+ radical cation was investigated. Whereas H2O2 oxidation ...
Luca Valgimigli - One of the best experts on this subject based on the ideXlab platform.
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acylated anthocyanins from sprouts of Raphanus sativus cv sango isolation structure elucidation and antioxidant activity
Food Chemistry, 2015Co-Authors: Riccardo Matera, Renato Iori, Simone Gabbanini, Serena Berretti, Riccardo Amorati, Gina Rosalinda De Nicola, Luca ValgimigliAbstract:Abstract Little is known on structure–activity relationships of antioxidant anthocyanins. Raphanus sativus cv Sango sprouts are among the richest sources (270 mg/100 g fresh weight). We isolated from sprouts’ juice 9 acylated anthocyanins, including 4 new compounds. All comprise a cyanidin core bearing 3–4 glucose units, multiply acylated with malonic and phenolic acids (ferulic and sinapic). All compounds were equally effective in inhibiting the autoxidation of linoleic acid in aqueous micelles, with rate constant for trapping peroxyl radicals kinh = (3.8 ± 0.7) × 104 M–1 s–1 at 37 °C. In acetonitrile solution kinh varied with acylation: (0.9–2.1) × 105 M–1 s–1 at 30 °C. Each molecule trapped a number n of peroxyl radicals ranging from 4 to 7. Anthocyanins bearing sinapic acid were more effective than those bearing the ferulic moiety. Under identical settings, deacylated cyanin, ferulic and sinapic acids had kinh of 0.4 × 105, 0.3 × 105 and 1.6 × 105 M–1 s–1 respectively, with n ranging 2–3. Results show the major role of acylation on antioxidant performance.
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kaiware daikon Raphanus sativus l extract a naturally multipotent chemopreventive agent
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Jessica Barillari, Renato Iori, Alessio Papi, Marina Orlandi, G Bartolini, Simone Gabbanini, Gian Franco Pedulli, Luca ValgimigliAbstract:Brassica vegetables are attracting major attention as healthy foods because of their content of glucosinolates (GLs) that release the corresponding isothiocyanates (ITCs) upon myrosinase hydrolysis. A number of studies have so far documented the chemopreventive properties of some ITCs. On the other hand, single nutrients detached from the food itself risk being somewhat “reductive”, since plants contain several classes of compounds endowed with a polyhedral mechanism of action. Our recent finding that 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) and 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC), released by the GLs purified from Japanese (Kaiware) Daikon (Raphanus sativus L.) seeds and sprouts, had selective cytotoxic/apoptotic activity on three human colon carcinoma cell lines prompted further research on the potential chemopreventive role of a standardized Kaiware Daikon extract (KDE), containing 10.5% w/w GRH and 3.8% w/w GRE, compared to its isolated components. KDE administered in combinatio...
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cytotoxic and antioxidant activity of 4 methylthio 3 butenyl isothiocyanate from Raphanus sativus l kaiware daikon sprouts
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Alessio Papi, Jessica Barillari, Renato Iori, Marina Orlandi, G Bartolini, Gian Franco Pedulli, M Paolini, Fiammetta Ferroni, Maria Grazia Fumo, Luca ValgimigliAbstract:There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase II detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulf...
Jessica Barillari - One of the best experts on this subject based on the ideXlab platform.
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kaiware daikon Raphanus sativus l extract a naturally multipotent chemopreventive agent
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Jessica Barillari, Renato Iori, Alessio Papi, Marina Orlandi, G Bartolini, Simone Gabbanini, Gian Franco Pedulli, Luca ValgimigliAbstract:Brassica vegetables are attracting major attention as healthy foods because of their content of glucosinolates (GLs) that release the corresponding isothiocyanates (ITCs) upon myrosinase hydrolysis. A number of studies have so far documented the chemopreventive properties of some ITCs. On the other hand, single nutrients detached from the food itself risk being somewhat “reductive”, since plants contain several classes of compounds endowed with a polyhedral mechanism of action. Our recent finding that 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) and 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC), released by the GLs purified from Japanese (Kaiware) Daikon (Raphanus sativus L.) seeds and sprouts, had selective cytotoxic/apoptotic activity on three human colon carcinoma cell lines prompted further research on the potential chemopreventive role of a standardized Kaiware Daikon extract (KDE), containing 10.5% w/w GRH and 3.8% w/w GRE, compared to its isolated components. KDE administered in combinatio...
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cytotoxic and antioxidant activity of 4 methylthio 3 butenyl isothiocyanate from Raphanus sativus l kaiware daikon sprouts
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Alessio Papi, Jessica Barillari, Renato Iori, Marina Orlandi, G Bartolini, Gian Franco Pedulli, M Paolini, Fiammetta Ferroni, Maria Grazia Fumo, Luca ValgimigliAbstract:There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase II detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulf...
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antioxidant and choleretic properties of Raphanus sativus l sprout kaiware daikon extract
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Jessica Barillari, E Speroni, M C Guerra, Rinaldo Cervellati, Stefano Costa, And Aneli Utan, Renato IoriAbstract:Brassica vegetables and glucosinolates contained therein are supposed to reduce the risk of cancer and to possess health-promoting properties. The benefits of a Brassica-based diet may be particularly expressed by eating sprouts, in which the glucosinolate content is higher than in mature vegetables. With this in mind, a first objective of this study was to evaluate the antioxidant properties of radish (Raphanus sativus L.) sprouts (Kaiware Daikon) extract (KDE), in which the glucosinolate glucoraphasatin (GRH), showing some antioxidant activity, is present at 10.5% w/w. The contribution of GRH to KDE's antioxidant activity was considered in two chemical assays (Trolox equivalent antioxidant capacity and Briggs−Rauscher methods). The total phenol assay by Folin−Ciocalteu reagent was performed to quantify the reducing capacity of KDE. Finally, on the basis of the putative choleretic properties of antioxidant plant extracts, the effect on the bile flow of KDE administration was investigated in an animal exp...
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isolation of 4 methylthio 3 butenyl glucosinolate from Raphanus sativus sprouts kaiware daikon and its redox properties
Journal of Agricultural and Food Chemistry, 2005Co-Authors: Jessica Barillari, Rinaldo Cervellati, M Paolini, Arnaud Tatibouet, Patrick Rollin, Renato IoriAbstract:The most promising among glucosinolates (GLs) are those bearing in their aglycon an extra sulfur function, such as glucoraphasatin (4-methylthio-3-butenyl GL; GRH) and glucoraphenin (4-methylsulfinyl-3-butenyl GL; GRE). The GRE/GRH redox couple is typically met among secondary metabolites of Raphanus sativus L. and, whereas GRE prevails in seeds, GRH is the major GL in full-grown roots. During the 10 days of sprouting of R. sativus seeds, the GRE and GRH contents were determined according to the Eurpean Union official method (ISO 9167-1). In comparison to the seeds, the GRE content in sprouts decreased from about 90 to about 12 μmol g-1 of dry weight (dw), whereas a 25-fold increasefrom about 3 to 76 μmol g-1 of dwof the GRH content was measured. An efficient pure GRH gram-scale production process from R. sativus (kaiware daikon) sprouts resulted in significant yield improvement of up to 2.2% (dw basis). The reaction of GRH with both H2O2 and ABTS•+ radical cation was investigated. Whereas H2O2 oxidation ...
Yasushi Nakamura - One of the best experts on this subject based on the ideXlab platform.
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comparison of the glucosinolate myrosinase systems among daikon Raphanus sativus japanese white radish varieties
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Yasushi Nakamura, Johan Meijer, Kei Nakamura, Yumi Asai, Toyoaki Wada, Kiwamu Tanaka, Tomoaki Matsuo, Shigehisa Okamoto, Yasuki Kitamura, Akiyoshi NishikawaAbstract:Myrosinase is a cytosolic plant enzyme present in daikon (Raphanus sativus, Japanese white radish) roots that hydrolyzes 4-methylthio-3-butenyl glucosinolate (MTBGLS) into the natural pungent agent 4-methylthio-3-butenyl isothiocyanate (MTBITC), which possesses antimicrobial, antimutagenic, and anticarcinogenic properties. The concentration of MTBGLS, myrosinase activity, and production of MTBITC in seven daikon varieties (one conventional and six heirlooms) were determined to rank the activity of the glucosinolate−myrosinase system and identify critical factors influencing the production of MTBITC. The six heirloom varieties produced 2.0–11.5 times higher levels of MTBITC as compared to the conventional variety, Aokubi, which is consumed by the present Japanese population. The myrosinase was located exclusively in the outer epidermal layer in Aokubi, and MTBGLS was widely distributed throughout the root tissue. Although the skin is a potentially rich source of myrosinase in Aokubi, the skin is usually pe...
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4 methylthio 3 butenyl isothiocyanate a principal antimutagen in daikon Raphanus sativus japanese white radish
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Yasushi Nakamura, Tomoaki Matsuo, Shigehisa Okamoto, Takako Iwahashi, Atsuo Tanaka, Jun Koutani, Kenji Sato, Kozo OhtsukiAbstract:The antimutagenic activity of n-hexane extracts from eight strains of daikon (Raphanus sativus; Japanese white radish) have been examined using the UV-induced mutation assay of Escherichia coli B/r WP2. A correlation was found between the potency of antimutagenicity and the amount of 4-(methylthio)-3-butenyl isothiocyanate (MTBITC) in their n-hexane extracts. Because the pure MTBITC also showed antimutagenicity, MTBITC is presumably the active antimutagen principle in n-hexane extracts of daikon. Among the eight strains of daikon studied, Aokubi, the improved common strain in Japan, contained 71.0 μmol of MTBITC in 100 g of fresh daikon. In contrast, Karami and Momoyama, which are original wild strains, contained much more MTBITC (363.5 and 168.0 μmol/100 g, respectively). In addition, phenethyl isothiocyanate was found in a lesser amount (5−33 nmol/100 g) in eight strains of daikon, and allyl isothiocyanate and benzyl isothiocyanate were not detectable in any strains (<3 nmol/100 g). The amount of total ...
Alessio Papi - One of the best experts on this subject based on the ideXlab platform.
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kaiware daikon Raphanus sativus l extract a naturally multipotent chemopreventive agent
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Jessica Barillari, Renato Iori, Alessio Papi, Marina Orlandi, G Bartolini, Simone Gabbanini, Gian Franco Pedulli, Luca ValgimigliAbstract:Brassica vegetables are attracting major attention as healthy foods because of their content of glucosinolates (GLs) that release the corresponding isothiocyanates (ITCs) upon myrosinase hydrolysis. A number of studies have so far documented the chemopreventive properties of some ITCs. On the other hand, single nutrients detached from the food itself risk being somewhat “reductive”, since plants contain several classes of compounds endowed with a polyhedral mechanism of action. Our recent finding that 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) and 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC), released by the GLs purified from Japanese (Kaiware) Daikon (Raphanus sativus L.) seeds and sprouts, had selective cytotoxic/apoptotic activity on three human colon carcinoma cell lines prompted further research on the potential chemopreventive role of a standardized Kaiware Daikon extract (KDE), containing 10.5% w/w GRH and 3.8% w/w GRE, compared to its isolated components. KDE administered in combinatio...
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cytotoxic and antioxidant activity of 4 methylthio 3 butenyl isothiocyanate from Raphanus sativus l kaiware daikon sprouts
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Alessio Papi, Jessica Barillari, Renato Iori, Marina Orlandi, G Bartolini, Gian Franco Pedulli, M Paolini, Fiammetta Ferroni, Maria Grazia Fumo, Luca ValgimigliAbstract:There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase II detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulf...
