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Volumn 19, Issue 6, 2014, Pages 6975-6986

Novel gram-scale production of enantiopure R-Sulforaphane from tuscan black kale seeds

Author keywords

Biphasic system; Brassica oleracea; Glucoraphanin; Glucosinolate; R sulforaphane; Tuscan black kale

Indexed keywords

GLUCORAPHANIN; GLUCOSINOLATE; GLYCOSIDASE; IMIDOESTER; ISOTHIOCYANIC ACID DERIVATIVE; SULFORAFAN; THIOGLUCOSIDASE;

EID: 84903286823     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19066975     Document Type: Article
Times cited : (25)

References (32)
  • 1
    • 0026577605 scopus 로고
    • A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure
    • Zhang, Y.; Talala y, P.; Cho, C.G.; Posner, G.H. A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA 1992, 89, 2399-2403.
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 2399-2403
    • Zhang, Y.1    Talalay, P.2    Cho, C.G.3    Posner, G.H.4
  • 3
    • 84903298698 scopus 로고    scopus 로고
    • ClinicalTrials.gov. Available online: accessed on 16 April
    • ClinicalTrials.gov. Available online: http://clinicaltrials.gov/ct2/ resultsterm=sulforaphane& Search=Search (accessed on 16 April 2014).
    • (2014)
  • 4
    • 55049121677 scopus 로고    scopus 로고
    • Determination of the absolute configuration of the glucosinolate methyl sulfoxide group reveals a stereospecific biosynthesis of the side chain
    • Vergara, F.; Wenzler, M.; Hansen, B.G.; Kliebenstein, D.J.; Halkier, B.A.; Gershenzon, J.; Schneider, B. Determination of the absolute configuration of the glucosinolate methyl sulfoxide group reveals a stereospecific biosynthesis of the side chain. Phytochemistry 2008, 69, 2737-2742.
    • (2008) Phytochemistry , vol.69 , pp. 2737-2742
    • Vergara, F.1    Wenzler, M.2    Hansen, B.G.3    Kliebenstein, D.J.4    Halkier, B.A.5    Gershenzon, J.6    Schneider, B.7
  • 5
    • 84919394461 scopus 로고    scopus 로고
    • Cell cycle effects of L-sulforaphane, a major antioxid ant from cruciferous vegetables: The role of the anaphase promoting complex
    • Li, S.Z.; Royce, S.G.; Ververis, K.; Karagiannis, T.C. Cell cycle effects of L-sulforaphane, a major antioxid ant from cruciferous vegetables: The role of the anaphase promoting complex. Hell. J. Nucl. Med. 2013, 17, 11-16.
    • (2013) Hell. J. Nucl. Med. , vol.17 , pp. 11-16
    • Li, S.Z.1    Royce, S.G.2    Ververis, K.3    Karagiannis, T.C.4
  • 6
    • 0005035167 scopus 로고
    • Synthese der racemischen und der optisch aktiven Formen des Sulforaphans
    • Schmid, H.; Karrer, P. Synthese der racemischen und der optisch aktiven Formen des Sulforaphans. Helv. Chim. Acta 1948, 31, 1497-1505.
    • (1948) Helv. Chim. Acta , vol.31 , pp. 1497-1505
    • Schmid, H.1    Karrer, P.2
  • 7
    • 0033526014 scopus 로고    scopus 로고
    • Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: A chem oenzymatic route to sulforaphane
    • Iori, R.; Bernardi, R.; Gueyrard, D.; Rollin, P.; Palmieri, S. Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: A chem oenzymatic route to sulforaphane. Bioorg. Med. Chem. Lett. 1999, 9, 1047-1048.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 1047-1048
    • Iori, R.1    Bernardi, R.2    Gueyrard, D.3    Rollin, P.4    Palmieri, S.5
  • 8
    • 82955235585 scopus 로고    scopus 로고
    • New method for the synthesis of sulforaphane and related isothiocyanates
    • Chen, X.; Li, Z.; Sun, X.; Ma, H.; Chen, X.; Ren, J.; Hu, K. New method for the synthesis of sulforaphane and related isothiocyanates. Synthesis 2011, 24, 3991-3996.
    • (2011) Synthesis , vol.24 , pp. 3991-3996
    • Chen, X.1    Li, Z.2    Sun, X.3    Ma, H.4    Chen, X.5    Ren, J.6    Hu, K.7
  • 9
    • 79955416779 scopus 로고    scopus 로고
    • The natural chemopreventive phytochemical R-sulforaphane is a far more potent inducer of th e carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer
    • Abdull Razis, A.F.; Iori, R.; Ioannides, C. The natural chemopreventive phytochemical R-sulforaphane is a far more potent inducer of th e carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer. Int. J. Cancer 2011, 128, 2775-2782.
    • (2011) Int. J. Cancer , vol.128 , pp. 2775-2782
    • Abdull Razis, A.F.1    Iori, R.2    Ioannides, C.3
  • 10
    • 84880400731 scopus 로고    scopus 로고
    • Cruciferous vegetables: Dietary phytochemicals for cancer prevention
    • Abdull Razis, A.F.; Noor, N.M. Cruciferous vegetables: Dietary phytochemicals for cancer prevention. Asian Pac. J. Cancer Prev. 2013, 14, 1565-1570.
    • (2013) Asian Pac. J. Cancer Prev. , vol.14 , pp. 1565-1570
    • Abdull Razis, A.F.1    Noor, N.M.2
  • 11
    • 78649467294 scopus 로고    scopus 로고
    • Nutraceutical antioxidants as novel neuroprotective agents
    • Kelsey, N.A.; Wilkins, H.M.; Linseman, D.A. Nutraceutical antioxidants as novel neuroprotective agents. Molecules 2010, 15, 7792-7814.
    • (2010) Molecules , vol.15 , pp. 7792-7814
    • Kelsey, N.A.1    Wilkins, H.M.2    Linseman, D.A.3
  • 12
    • 28444453268 scopus 로고    scopus 로고
    • Purification of sulforaphane from Brassica oleracea seed meal using low-pressure column chromatography
    • Liang, H.; Yuan, Q.; Xiao, Q. Purification of sulforaphane from Brassica oleracea seed meal using low-pressure column chromatography. J. Chromatogr. B 2005, 828, 91-96.
    • (2005) J. Chromatogr. B , vol.828 , pp. 91-96
    • Liang, H.1    Yuan, Q.2    Xiao, Q.3
  • 13
    • 38349039813 scopus 로고    scopus 로고
    • Separation and purification of sulforaphane from broccoli seeds by solid phase extraction and preparative high-performance liquid chromatography
    • Liang H.Li C.Yuan Q.Vriesekoop F. Separation and purification of sulforaphane from broccoli seeds by solid phase extraction and preparative high-performance liquid chromatography. J. Agric. Food Chem. 2007.55.8047-53.
    • (2007) J. Agric. Food Chem. , vol.55 , pp. 8047-8053
    • Liang, H.1    Li, C.2    Yuan, Q.3    Vriesekoop, F.4
  • 14
    • 41649090154 scopus 로고    scopus 로고
    • Optimization of sulforaphane separation from broccoli seeds by macroporous resins
    • Li, C.; Liang, H.; Yuana , Q.; Houa, X. Optimization of sulforaphane separation from broccoli seeds by macroporous resins. Separ. Sci. Technol. 2008, 43, 609-623.
    • (2008) Separ. Sci. Technol. , vol.43 , pp. 609-623
    • Li, C.1    Liang, H.2    Yuana, Q.3    Houa, X.4
  • 15
    • 84864948268 scopus 로고    scopus 로고
    • Quantitative profiling of glucosinolates by LC-MS analysis reveals several cultivars of cabbage and kale as promising candidates for sulforaphane production
    • Sasaki, K; Neyazaki, M.; Shindo, K.; Ogawa, T.; Mo mose, M. Quantitative profiling of glucosinolates by LC-MS analysis reveals several cultivars of cabbage and kale as promising candidates for sulforaphane production. J. Chromatogr. B 2012, 903, 171-176.
    • (2012) J. Chromatogr. B , vol.903 , pp. 171-176
    • Sasaki, K.1    Neyazaki, M.2    Shindo, K.3    Ogawa, T.4    Momose, M.5
  • 16
    • 77957876664 scopus 로고    scopus 로고
    • Intact glucosinolates modulate hepatic cytochrome P450 and phase II conjugation activities and may contribute directly to the chemopreventive activity of cruc iferous vegetables
    • Abdull Razis, A.F.; Bagatta, M.; de Nicola, G.R.; Iori, R.; Ioannides, C. Intact glucosinolates modulate hepatic cytochrome P450 and phase II conjugation activities and may contribute directly to the chemopreventive activity of cruc iferous vegetables. Toxicology 2010, 277, 74-85.
    • (2010) Toxicology , vol.277 , pp. 74-85
    • Abdull Razis, A.F.1    Bagatta, M.2    De Nicola, G.R.3    Iori, R.4    Ioannides, C.5
  • 17
    • 77954188270 scopus 로고    scopus 로고
    • Glucosinolates structures and analysis in food
    • Clarke, D.B. Glucosinolates, structures and analysis in food. Anal. Method. Instrum. 2010, 2, 301-416.
    • (2010) Anal. Method. Instrum. , vol.2 , pp. 301-416
    • Clarke, D.B.1
  • 18
    • 0038359438 scopus 로고    scopus 로고
    • Separation and purification of glucosinolates from crude plant homogenates by high-speed counter-current chromatography
    • Fahey, J.F.; Wade, K.L.; Stephenson, K.K.; Chou, F.E. Separation and purification of glucosinolates from crude plant homogenates by high-speed counter-current chromatography. J. Chromatogr. A 2003, 996, 85-93.
    • (2003) J. Chromatogr. A , vol.996 , pp. 85-93
    • Fahey, J.F.1    Wade, K.L.2    Stephenson, K.K.3    Chou, F.E.4
  • 19
    • 70349101647 scopus 로고    scopus 로고
    • Enantiopure sulforaphane analogues with various substituents at the sulfinyl sulfur: Asymmetric synthesis and biologi cal activities
    • Khiar, N.; Werner, S.; Mallouk, S.; Lieder, F.; Alcudia, A.; Fernández, I. Enantiopure sulforaphane analogues with various substituents at the sulfinyl sulfur: Asymmetric synthesis and biologi cal activities. J. Org. Chem. 2009, 74, 6002-6009.
    • (2009) J. Org. Chem. , vol.74 , pp. 6002-6009
    • Khiar, N.1    Werner, S.2    Mallouk, S.3    Lieder, F.4    Alcudia, A.5    Fernández, I.6
  • 20
    • 0001135571 scopus 로고    scopus 로고
    • Gas chromatography/mass spectrometry method for the determination of sulforaphane and sulforaphane nitr ile in broccoli
    • Chiang, W.C.K.; Pusateri, D.J.; Leitz, R.E.A. Gas chromatography/mass spectrometry method for the determination of sulforaphane and sulforaphane nitr ile in broccoli. J. Agric. Food Chem. 1998, 46, 1018-1021.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 1018-1021
    • Chiang, W.C.K.1    Pusateri, D.J.2    Leitz, R.E.A.3
  • 21
    • 77955656454 scopus 로고    scopus 로고
    • Preparation and stability investigation of the inclusion complex of sulforaphane with hydroxypropyl-β-cyclodextrin
    • Wu, H.; Liang, H.; Yuan, Q.; Wang, T.; Yan, X. Preparation and stability investigation of the inclusion complex of sulforaphane with hydroxypropyl- β-cyclodextrin. Carbohydr. Polym. 2010, 82, 613-617.
    • (2010) Carbohydr. Polym. , vol.82 , pp. 613-617
    • Wu, H.1    Liang, H.2    Yuan, Q.3    Wang, T.4    Yan, X.5
  • 22
    • 36849026035 scopus 로고    scopus 로고
    • Evaluation of the safety and bioactivity of purified and semi-purified glucoraphanin
    • Lai, R.H.; Keck, A.S.; Wallig, M.A.; West, L.G.; Jeffery, E.H. Evaluation of the safety and bioactivity of purified and semi-purified glucoraphanin. Food Chem. Toxicol. 2008, 46, 195-202.
    • (2008) Food Chem. Toxicol. , vol.46 , pp. 195-202
    • Lai, R.H.1    Keck, A.S.2    Wallig, M.A.3    West, L.G.4    Jeffery, E.H.5
  • 23
    • 0001520970 scopus 로고    scopus 로고
    • Initial and final products, nitriles, and ascorbigens produced in myrosinase-catalyzed hydr olysis of indole glucosinolates
    • Agerbirk, N.; Olsen, C.E.; Sørensen, H. Initial and final products, nitriles, and ascorbigens produced in myrosinase-catalyzed hydr olysis of indole glucosinolates. J. Agric. Food Chem. 1998, 46, 1563-1571.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 1563-1571
    • Agerbirk, N.1    Olsen, C.E.2    Sørensen, H.3
  • 24
    • 80052746485 scopus 로고    scopus 로고
    • Induction of epoxide hydrolase and glucuron osyl transferase by isothiocyanates and intact glucosinolates in precision-cut rat liver slices: Importance of side-chain substituent and chirality
    • Abdull Razis, A.F.; Bagatta, M.; de Nicola, G.R.; Iori, R.; Ioannides, C. Induction of epoxide hydrolase and glucuron osyl transferase by isothiocyanates and intact glucosinolates in precision-cut rat liver slices: Importance of side-chain substituent and chirality. Arch. Toxicol. 2011, 85, 919-927.
    • (2011) Arch. Toxicol. , vol.85 , pp. 919-927
    • Abdull Razis, A.F.1    Bagatta, M.2    De Nicola, G.R.3    Iori, R.4    Ioannides, C.5
  • 25
    • 84880698963 scopus 로고    scopus 로고
    • Protective role of (RS)-glucoraphanin bioactivated with myrosinase in an experimental model of multiple sclerosis
    • Giacoppo, S.; Galuppo, M.; Iori, R.; de Nicola, G.R.; Cassata, G.; Bramanti, P.; Mazzon, E. Protective role of (RS)-glucoraphanin bioactivated with myrosinase in an experimental model of multiple sclerosis. CNS Neurosci. Ther. 2013, 19, 577-584.
    • (2013) CNS Neurosci. Ther. , vol.19 , pp. 577-584
    • Giacoppo, S.1    Galuppo, M.2    Iori, R.3    De Nicola, G.R.4    Cassata, G.5    Bramanti, P.6    Mazzon, E.7
  • 26
    • 84881373710 scopus 로고    scopus 로고
    • Anti-inflammatory and anti-apoptotic effects of (RS)-glucoraphanin bioactivated with myrosinase in murine sub-acute and acute MPTP-induced Parkinson?s Disease
    • Galuppo, M.; Iori, R.; de Nicola, G.R.; Ferrantelli, V.; Bramanti, P.; Mazzon, E. Anti-inflammatory and anti-apoptotic effects of (RS)-glucoraphanin bioactivated with myrosinase in murine sub-acute and acute MPTP-induced Parkinson?s Disease. Bioorg. Med. Chem. 2013, 21, 5532-5547.
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 5532-5547
    • Galuppo, M.1    Iori, R.2    De Nicola, G.R.3    Ferrantelli, V.4    Bramanti, P.5    Mazzon, E.6
  • 29
    • 0025359610 scopus 로고
    • An improved method for the purification of my rosinase and its physicochemical characterization
    • Pessina, A.; Thomas, R.M.; Palmieri, S.; Luisi, P.L. An improved method for the purification of my rosinase and its physicochemical characterization. Arch. Biochem. Biophys. 1990, 280, 383-389.
    • (1990) Arch. Biochem. Biophys. , vol.280 , pp. 383-389
    • Pessina, A.1    Thomas, R.M.2    Palmieri, S.3    Luisi, P.L.4
  • 30
    • 0003179805 scopus 로고
    • Oilseedsdetermination of glucosinolates high performance liquid chromatography
    • European Economic Community Commisssion Regulation EEC No. 1864/90
    • European Economic Community, Commisssion Regulation, EEC No. 1864/ 90. Oilseedsdetermination of glucosinolates high performance liquid chromatography. Off. J. Eur. Comm. 1990, L170, 27-34.
    • (1990) Off. J. Eur. Comm. , vol.L170 , pp. 27-34
  • 31
    • 84877588109 scopus 로고    scopus 로고
    • Comparison of bioactive phytochemical content and release of isothiocyanates in selected brassica sprouts
    • De Nicola, G.R.; Bagatta, M.; Pagnotta, E.; Angelino, D.; Gennari, L.; Ninfali, P.; Rollin, P.; Iori, R. Comparison of bioactive phytochemical content and release of isothiocyanates in selected brassica sprouts. Food Chem. 2013, 141, 297-303.
    • (2013) Food Chem. , vol.141 , pp. 297-303
    • De Nicola, G.R.1    Bagatta, M.2    Pagnotta, E.3    Angelino, D.4    Gennari, L.5    Ninfali, P.6    Rollin, P.7    Iori, R.8


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