Isorhapontigenin: A novel bioactive stilbene from wine grapes

Food Chemistry

Volumn 135, Issue 3, 2012, Pages 1353-1359

  Fernández Marín, María Isabel ^a   Guerrero, Raúl F ^a   García Parrilla, María Carmen ^b   Puertas, Belén ^a   Richard, Tristan ^c   Rodriguez Werner, Miriam Adriana ^d   Winterhalter, Peter ^d   Monti, Jean Pierre ^c   Cantos Villar, Emma ^a  

^a IFAPA CENTRO EL TORUÑO   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

^c Bordeaux Segalen University   (France)

^d TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Bioactivity; Grape; HSCCC; Isorhapontigenin; NMR; Stilbenes; UVC

Indexed keywords

GRAPE; HSCCC; ISORHAPONTIGENIN; STILBENES; UVC;

BIOACTIVITY; LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

FRUITS;

ISORHAPONTIGENIN; RESVERATROL; STILBENE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CONCENTRATION (PARAMETERS); COUNTER CURRENT CHROMATOGRAPHY; DRUG ACTIVITY; FRACTIONATION; GRAPE; HARVEST; HETERONUCLEAR MULTIPLE BOND CONNECTIVITY; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTON CORRELATION SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; ROTATING FLAME NUCLEAR OVERHAUSER EFFECT SPECTROSCOPY; ULTRAVIOLET C RADIATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; PLANT EXTRACTS; STILBENES; ULTRAVIOLET RAYS; VITIS;

VITACEAE; VITIS VINIFERA;

EID: 84865740852     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.05.086     Document Type: Article

References (37)

1. T.A. Aburjai Anti-platelet stilbenes from aerial parts of Rheum palaestinum Phytochemistry 55 2000 407 410
2. Z. Ali, T. Tanaka, I. Iliya, M. Iinuma, M. Furusawa, and T. Ito Phenolic constituents of Gnetum klossii Journal of Natural Products 66 2003 558 560 (Pubitemid 36531912)
3. F. Buiarelli, F. Coccioli, R. Jasionowska, M. Merolle, and A. Terracciano Analysis of some stilbenes in Italian wines by liquid chromatography/tandem mass spectrometry Rapid Communications in Mass Spectrometry 21 2007 2955 2964 (Pubitemid 47401432)
4. E. Cantos, J.C. Espin, and F.A. Tomas-Barberan Postharvest stilbene-enrichment of red and white table grape varieties using UV-C irradiation pulses Journal of Agricultural and Food Chemistry 50 2002 6322 6329 (Pubitemid 35216734)
5. R.F. Guerrero, M.C. García-Parrilla, B. Puertas, and E. Cantos-Villar Wine, resveratrol and health: a review Natural Product Communications 4 2009 635 658
6. R.F. Guerrero, B. Puertas, M.I. Fernández, M. Palma, and E. Cantos-Villar Induction of stilbenes in grapes by UV-C: comparison of different subspecies of Vitis Innovative Food Science and Emerging Technologies 11 2010 231 238
7. R.F. Guerrero, B. Puertas, M.J. Jiménez, J. Cacho, and E. Cantos-Villar Monitoring the process to obtain red wine enriched in resveratrol and piceatannol without quality loss Food Chemistry 122 2010 195 202
8. J.B. Harborne The comparative biochemistry of phytoalexin induction in plants Biochemical Systematics and Ecology 27 1999 335 367 (Pubitemid 29156950)
9. S. He, Y. Lu, L. Jiang, B. Wu, F. Zhang, and Y. Pan Preparative isolation and purification of antioxidative stilbene oligomers from Vitis chunganensis using high-speed counter-current chromatography in stepwise elution mode Journal of Separation Science 32 2009 2339 2345
10. I. Iliya, Z. Ali, T. Tanaka, M. Iinuma, M. Furusawa, and K.-I. Nakaya Stilbene derivatives from Gnetum gnemon Linn Phytochemistry 62 2003 601 606 (Pubitemid 36216080)
11. Y. Ito Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography Journal of Chromatography A 1065 2005 145 168 (Pubitemid 40228728)
12. P. Jeandet, A.-C. Douillet-Breuil, R. Bessis, S. Debord, M. Sbaghi, and M. Adrian Phytoalexins from the vitaceae: Biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism Journal of Agricultural and Food Chemistry 50 2002 2731 2741 (Pubitemid 34493577)
13. V. Jerkovic, F. Nguyen, S. Nizet, and S. Collin Combinatorial synthesis, reversed-phase and normal-phase high-performance liquid chromatography elution data and liquid chromatography/positive atmospheric pressure chemical ionization tandem mass spectra of methoxylated and glycosylated resveratrol analogues Rapid Communications in Mass Spectrometry 21 2007 2456 2466 (Pubitemid 47203273)
14. E. Kato, Y. Tokunaga, and F. Sakan Stilbenoids isolated from the seeds of Melinjo (Gnetum gnemon. L.) and their biological activity Journal of Agricultural and Food Chemistry 57 2009 2544 2549
15. 2-induced inhibition of gap junctional intercellular communication in rat liver cell line Food and Chemical Toxicology 47 2009 404 409
16. S.K. Ko, S.M. Lee, and W.K. Whang Anti-platelet aggregation activity of stilbene derivatives from Rheum undulatum Archives of Pharmacal Research 22 1999 401 403
17. N. Landrault, F. Larronde, J.C. Delaunay, C. Castagnino, J. Vercauteren, and J.M. Merillon Levels of stilbene oligomers and astilbin in French wines and grapes during noble rot development Journal of Agricultural and Food Chemistry 50 2002 2046 2052 (Pubitemid 34260009)
18. H.-L. Li, A.-B. Wang, Y. Huang, D.-P. Liu, C. Wei, and G.M. Williams Isorhapontigenin, a new resveratrol analog, attenuates cardiac hypertrophy via blocking signaling transduction pathways Free Radical Biology and Medicine 38 2005 243 257 (Pubitemid 39656135)
19. X.-M. Li, M. Lin, Y.-H. Wang, and X. Liu Four new stilbenoids from the lianas of Gnetum montanum f. megalocarpum Planta Medica 70 2004 160 165 (Pubitemid 38299779)
20. A.-L. Liu, F. Yang, M. Zhu, D. Zhou, M. Lin, and S.M.-Y. Lee In vitro anti-influenza viral activities of stilbenoids from the lianas of Gnetum pendulum Planta Medica 76 2010 1874 1876
21. H. Matsuda, T. Morikawa, I. Toguchida, J.-Y. Park, S. Harima, and M. Yoshikawa Antioxidant constituents from rhubarb: Structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides Bioorganic and Medicinal Chemistry 9 2001 41 50 (Pubitemid 32007962)
22. H. Matsuda, S. Tewtrakul, T. Morikawa, and M. Yoshikawa Anti-allergic activity of stilbenes from Korean rhubarb (Rheum undulatum L.): Structure requirements for inhibition of antigen-induced degranulation and their effects on the release of TNF-α and IL-4 in RBL-2H3 cells Bioorganic and Medicinal Chemistry 12 2004 4871 4876 (Pubitemid 39164395)
23. F. Mattivi, F. Reniero, and S. Korhammer Isolation, characterization, and evolution in red wine vinification of resveratrol monomers Journal of Agricultural and Food Chemistry 43 1995 1820 1823
24. F. Mattivi, U. Vrhovsek, G. Malacarne, D. Masuero, L. Zulini, and M. Stefanini Profiling of resveratrol oligomers, important stress metabolites, accumulating in the leaves of hybrid Vitis vinifera (Merzling × Teroldego) genotypes infected with Plasmopara viticola Journal of Agricultural and Food Chemistry 59 2011 5364 5375
25. N. Mulinacci, M. Innocenti, A.R. Santamaria, G. la Marca, and G. Pasqua High-performance liquid chromatography/electrospray ionization tandem mass spectrometric investigation of stilbenoids in cell cultures of Vitis vinifera L., cv. Malvasia Rapid Communications in Mass Spectrometry 24 2010 2065 2073
26. R. Pezet, C. Perret, J.B. Jean-Denis, R. Tabacchi, K. Gindro, and O. Viret Δ-viniferin, a resveratrol dehydrodimer: One of the major stilbenes synthesized by stressed grapevine leaves Journal of Agricultural and Food Chemistry 51 2003 5488 5492
27. T. Püssa, J. Floren, P. Kuldkepp, and A. Raal Survey of grapevine Vitis vinifera stem polyphenols by liquid chromatography-diode array detection-tandem mass spectrometry Journal of Agricultural and Food Chemistry 54 2006 7488 7494 (Pubitemid 44645762)
28. K.A. Roupe, G.L. Helms, S.C. Halls, J.A. Yáñez, and N.M. Davies Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: Applications to metabolism, pharmacokinetics and anti-cancer studies Journal of Pharmacy and Pharmaceutical Sciences 8 2005 374 386 (Pubitemid 41529316)
29. K.A. Roupe, C.M. Remsberg, J.A. Yáñez, and N.M. Davies Pharmacometrics of stilbenes: Seguing towards the clinic Current clinical pharmacology 1 2006 81 101
30. A. Silayo, B.T. Ngadjui, and B.M. Abegaz Homoisoflavonoids and stilbenes from the bulbs of Scilla nervosa subsp. rigidifolia Phytochemistry 52 1999 947 955
31. C. Vergara, D. von Baer, C. Mardones, A. Wilkens, K. Wernekinck, and A. Damm Stilbene levels in grape cane of different cultivars in Southern Chile: Determination by HPLC-DAD-MS/MS method Journal of Agricultural and Food Chemistry 60 2012 929 933
32. X. Vitrac, J.-P. Monti, J. Vercauteren, G. Deffieux, and J.-M. Merillon Direct liquid chromatographic analysis of resveratrol derivatives and flavanonols in wines with absorbance and fluorescence detection Analytica Chimica Acta 458 2002 103 110 (Pubitemid 34273824)
33. Q.L. Wang, M. Lin, and G.T. Liu Antioxidative activity of natural isorhapontigenin Japanese Journal of Pharmacology 87 2001 61 66
34. A. Wilkens, J. Paulsen, V. Wray, and P. Winterhalter Structures of two novel trimeric stilbenes obtained by horseradish peroxidase catalyzed biotransformation of trans-resveratrol and (-) - viniferin Journal of Agricultural and Food Chemistry 58 2010 6754 6761
35. P. Winterhalter ASEV honorary research lecture 2008: Application of countercurrent chromatography for wine research and wine analysis American Journal of Enology and Viticulture 60 2009 123 129
36. K. Xiao, H.-J. Zhang, L.-J. Xuan, J. Zhang, Y.-M. Xu, and D.-L. Bai Stilbenoids: Chemistry and bioactivities Studies in Natural Products Chemistry 34 2008 453 646
37. R. Zamora-Ros, C. Andres-Lacueva, R.M. Lamuela-Raventós, T. Berenguer, P. Jakszyn, and C. Martínez Concentrations of resveratrol and derivatives in foods and estimation of dietary intake in a Spanish population: European Prospective Investigation into Cancer and Nutrition (EPIC)-Spain cohort British Journal of Nutrition 100 2008 188 196