Identification and analysis of isothiocyanates and new acylated anthocyanins in the juice of Raphanus sativus cv. Sango sprouts

Food Chemistry

Volumn 133, Issue 2, 2012, Pages 563-572

  Matera, Riccardo ^a   Gabbanini, Simone ^a   De Nicola, Gina Rosalinda ^b   Iori, Renato ^b   Petrillo, Gianna ^c   Valgimigli, Luca ^c  

^a RandD Division   (Italy)

^b ISTITUTO NAZIONALE DELLA NUTRIZIONE   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Anthocyanin; Antioxidants; Isothiocyanate; Mass spectrometry; Radish sprouts; Sango

Indexed keywords

ACETONE EXTRACTS; ACID HYDROLYSIS; AGLYCONES; ANTIOXIDANTS; CYANIDIN; DIETARY SOURCES; GC-MS ANALYSIS; HPLC ANALYSIS; HPLC-PDA-ESI-MS; ISOTHIOCYANATE; ISOTHIOCYANATES; RADISH SPROUTS; RAPHANUS SATIVUS; SANGO;

ACETONE; ACYLATION; HEXANE; MASS SPECTROMETRY; TRACE ELEMENTS;

ANTHOCYANINS;

4 METHYLSULFINYL 3 BUTENYL ISOTHIOCYANATE; 4 METHYLTHIO 3 BUTENYL ISOTHIOCYANATE; ACETIC ACID; ACETONE; AGLYCONE; ANTHOCYANIN; CAFFEIC ACID; CYANIDIN 3 DIGLY(FERULOYL) 5 GLY(SUCCINOYL); CYANIDIN 3 DIGLY(SINAPOYL FERULOYL) 5 DIGLY(MALONOYL); CYANIDIN 3 DIGLY(SINAPOYL FERULOYL) 5 DIGLYL(MALONOYL); CYANIDIN 3 DIGLY(SINAPOYL FERULOYL) 5 GLY; FERULIC ACID; HEXANE; ISOTHIOCYANIC ACID DERIVATIVE; MALONIC ACID; PARA COUMARIC ACID; SINAPIC ACID; SOPHOROSE; SUCCINIC ACID; UNCLASSIFIED DRUG; PLANT EXTRACT;

ACYLATION; ARTICLE; DEACYLATION; DRUG ISOLATION; ELECTROSPRAY MASS SPECTROMETRY; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MASS FRAGMENTOGRAPHY; METHODOLOGY; NONHUMAN; PLANT; RADISH; SANGO; SPROUT; ANALYSIS; BEVERAGE; CHEMICAL STRUCTURE; CHEMISTRY; GROWTH, DEVELOPMENT AND AGING; RAPHANUS;

RAPHANUS SATIVUS;

ANTHOCYANINS; BEVERAGES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ISOTHIOCYANATES; MOLECULAR STRUCTURE; PLANT EXTRACTS; RAPHANUS;

EID: 84858296206     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.01.050     Document Type: Article

References (31)

1. P. Arapitsas, P.J.R. Sjoeberg, and C. Turner Characterisation of anthocyanins in red cabbage using high resolution liquid chromatography coupled with photodiode array detection and electrospray ionization-linear ion trap mass spectrometry Food Chemistry 109 2008 219 226
2. J. Barillari, R. Cervellati, M. Paolini, A. Tatibouet, P. Rollin, and R. Iori Isolation of 4-methylthio-3-butenyl glucosinolate from Raphanus sativus sprouts (kaiware daikon) and its redox properties Journal of Agricultural and Food Chemistry 53 2005 9890 9896 (Pubitemid 43081194)
3. C.S. Charron, B.A. Clevidence, S.J. Britz, and J.A. Novotny Effect of dose size on bioavailability of acylated and nonacylated anthocyanins from red cabbage (Brassica oleracea L. Var. capitata) Journal of Agricultural and Food Chemistry 55 2007 5354 5362 (Pubitemid 47056098)
4. C.C. Conaway, S.M. Getahun, L.L. Liebes, D.J. Pusateri, D.K. Topham, M. Botero-Omary, and F.L. Chung Disposition of glucosinolates and sulforaphane in humans after ingestion of steamed and fresh broccoli Nutrition and Cancer 38 2000 168 178 (Pubitemid 32762016)
5. A. Crozier, I.B. Jaganath, and M.N. Clifford Dietary phenolics: chemistry, bioavailability and effects on health Natural Products Reports 26 2009 1001 1043
6. C. Fimognari, M. Lenzi, and P. Hrelia Chemoprevention of cancer by isothiocyanates and anthocyanins: mechanisms of action and structure-activity relationship Current Medicinal Chemistry 15 2008 440 447 (Pubitemid 351472410)
7. M.M. Giusti, H. Ghanadan, and R.E. Wrolstad Elucidation of the structure and conformation of red radish (Raphanus sativus) anthocyanins using one- and two-dimensional nuclear magnetic resonance techniques Journal of Agricultural and Food Chemistry 46 1998 4858 4863 (Pubitemid 128488229)
8. M.M. Giusti, and R.E. Wrolstad Characterization of red radish anthocyanins Journal of Food Science 61 1996 322 326 (Pubitemid 126581911)
9. Y. Goda, T. Shimizu, Y. Kato, M. Nakamura, T. Maitani, T. Yamada, N. Terahara, and M. Yamaguchi Two acylated anthocyanins from purple sweet potato Phytochemistry 44 1997 183 186 (Pubitemid 27091453)
10. M. Horbowicz, R. Kosson, A. Grzesiuk, and H. Debski Anthocyanins of fruits and vegetables - their occurrence, analysis and role in human nutrition Vegetable Crops Research Bullettin 68 2008 5 22
11. M. Khoobchandani, B.K. Ojeswi, N. Ganesh, M.M. Srivastava, S. Gabbanini, R. Matera, R. Iori, and L. Valgimigli Antimicrobial properties and analytical profile of traditional Eruca sativa seed oil: comparison with various aerial and root plant extracts Food Chemistry 120 2010 217 224
12. A. Kraemer-Schafhalter, T.H. Fuchs, and W. Pfannhauser Solid-phase extraction (SPE) a comparison of 16 materials for the purification of anthocyanins from Aronia melanocarpa var nero Journal of the Science of Food and Agriculture 78 1998 435 440 (Pubitemid 28533936)
13. M. Kristensen, K.S. Krogholm, H. Frederiksen, F. Duus, C. Cornett, S.H. Bugel, and S.E. Rasmussen Improved synthesis methods of standards used for quantitative determination of total isothiocyanates from broccoli in human urine Journal of Chromatography B 852 2007 229 234 (Pubitemid 46830114)
14. n identification of new anthocyanins in Purple Bordeaux radish (R. sativus L. variety) Journal of Agricultural and Food Chemistry 59 2011 6616 6627
15. C. Malien-Aubert, O. Dangles, and M.J. Amiot Color stability of commercial anthocyanin-based extracts in relation to the phenolic composition. Protective effects by intra- and intermolecular copigmentation Journal of Agricultural and Food Chemistry 49 2001 170 176 (Pubitemid 32104506)
16. T.K. McGhie, and M.C. Walton The bioavailability and absorption of anthocyanins: towards a better understanding Molecolar Nutrition & Food Research 51 2007 702 713 (Pubitemid 47083681)
17. D.A. Moreno, S. Pérez-Balibrea, F. Ferreres, Á. Gil-Izquierdo, and C. García-Viguera Acylated anthocyanins in broccoli sprouts Food Chemistry 123 2010 358 363
18. M. Mori, S. Nakagawa, M. Maeschima, S. Niiura, and K. Yoshida Anthocyanin from the rhizome of Raphanus sativus, and change in the composition during maturation Heterocycles 69 2006 239 251
19. H. Olsen, K. Aaby, and G.I. Borge Characterization, quantification, and yearly variation of the naturally occurring polyphenols in a common red variety of Curly Kale (Brassica oleracea L. convar. acephala var. sabellica cv. 'Redbor') Journal of Agricultural and Food Chemistry 58 2010 11346 11354
20. T. Otsuki, H. Matsufuji, M. Takeda, M. Toyoda, and Y. Goda Acylated anthocyanins from red radish (Raphanus sativus L.) Phytochemistry 60 2002 79 87 (Pubitemid 34516843)
21. Papi, A., Orlandi, M., Bartolini, G., Barillari, J., Iori, R., Paolini, M., Ferroni, F., Grazia Fumo, M., Pedulli, G. F. & Valgimigli, L. (2008). Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) sprouts. Journal of Agricultural and Food Chemistry, 56, 875-883. (Pubitemid 351300258)
22. N. Saito, K. Toki, Y. Morita, A. Hoshino, S. Iida, A. Shigihara, and T. Honda Acylated peonidin glycosides from duskish mutant flowers of Ipomoea nil Phytochemistry 66 2005 1852 1860 (Pubitemid 41080091)
23. M. Scordino, A. Di Mauro, A. Passerini, and E. Maccarone Adsorption of flavonoids on resins: cyanidin 3-glucoside Journal of Agricultural and Food Chemistry 52 2004 1965 1972
24. N.P. Seeram Berry fruits for cancer prevention: current status and future prospects Journal of Agricultural and Food Chemistry 56 2008 630 635 (Pubitemid 351300223)
25. S. Tamura, K. Tsuji, P. Yongzhen, M. Ohnishi-Kameyama, and N. Murakami Six new acylated anthocyanins from red radish (Raphanus sativus) Chemical & Pharmaceutical Bulletin (Tokyo) 58 2010 1259 1262
26. F. Tatsuzawa, N. Saito, K. Toki, K. Shinoda, A. Shigihara, and T. Honda Acylated cyanidin 3-sophoroside-5-glucosides from the purple roots of red radish (Raphanus sativus L.) 'Benikanmi' Journal of the Japanese Society for Horticultural Science 79 2010 103 107
27. F. Tatsuzawa, K. Toki, N. Saito, K. Shinoda, A. Shigihara, and T. Honda Anthocyanin occurrence in the root peels, petioles and flowers of red radish (Raphanus sativus L.) Dyes and Pigments 79 2008 83 88
28. L. Valgimigli, and R. Iori Antioxidant and pro-oxidant capacities of ITCs Environmental and Molecular Mutagenesis 50 2009 222 237
29. L.S. Wang, and G.D. Stoner Anthocyanins and their role in cancer prevention Cancer Letters 269 2008 281 290
30. X. Wu, and R.L. Prior Identification and characterization of anthocyanins by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in common foods in the United States: vegetables, nuts, and grains Journal of Agricultural and Food Chemistry 53 2005 3101 3113 (Pubitemid 40528455)
31. Y. Zhang, K.L. Wade, T. Prestera, and P. Talalay Quantitative determination of isothiocyanates, dithiocarbamates, carbon disulfide, and related thiocarbonyl compounds by cyclocondensation with 1,2-benzenedithiol Analytical Biochemistry 239 1996 160 167 (Pubitemid 26268798)