13C NMR and LC-MS Profiling of Stilbenes from Elicited Grapevine Hairy Root Cultures

Journal of Natural Products

Volumn 79, Issue 11, 2016, Pages 2846-2855

  Tisserant, Leo Paul ^a,b   Hubert, Jane ^a   Lequart, Michelle ^b   Borie, Nicolas ^a   Maurin, Nicolas ^a   Pilard, Serge ^c   Jeandet, Philippe ^a   Aziz, Aziz ^a   Renault, Jean Hugues ^a   Nuzillard, Jean Marc ^a   Clément, Christophe ^a   Boitel Conti, Michèle ^b   Courot, Eric ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b Université de Picardie Jules Verne   (France)

^c UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRIN; EPSILON VINIFERIN; ERIODICTYOL; FLAVONOID; JASMONIC ACID METHYL ESTER; MAACKIN; NARINGENIN; NATURAL PRODUCT; PALLIDOL; PICEATANNOL; PLANT EXTRACT; RESVERATROL; SCIRPUSIN A; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; VITISIN B; 3,3',4,5'-TETRAHYDROXYSTILBENE; BENZOFURAN DERIVATIVE; CYCLOPENTANE DERIVATIVE; EPSILON-VINIFERIN; FLAVANONE DERIVATIVE; MALVIDIN-3-O-GLUCOSIDE-4 VINYL; OXYLIPIN; PHENOL DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; COST EFFECTIVENESS ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; GRAPE; HAIRY ROOT CULTURE; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PARTITION CHROMATOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT; VITIS;

BENZOFURANS; CHROMATOGRAPHY, LIQUID; CYCLOPENTANES; FLAVANONES; FLAVONOIDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXYLIPINS; PHENOLS; PLANT ROOTS; POLYCYCLIC COMPOUNDS; STILBENES; VITIS;

EID: 84999157262     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.6b00608     Document Type: Article

References (41)

1. Abe, N.; Ito, T.; Ohguchi, K.; Nasu, M.; Masuda, Y.; Oyama, M.; Nozawa, Y.; Ito, M.; Iinuma, M. J. Nat. Prod. 2010, 73, 1499-1506 10.1021/np1002675
2. Chen, X.; Qiao, H.; Liu, T.; Yang, Z.; Xu, L.; Xu, Y.; Ge, H. M.; Tan, R. X.; Li, E. Antiviral Res. 2012, 95, 30-36 10.1016/j.antiviral.2012.05.001
3. Chung, E. Y.; Kim, B. H.; Lee, M. K.; Yun, Y. P.; Lee, S. H.; Min, K. R.; Kim, Y. Planta Med. 2003, 69, 710-714 10.1055/s-2003-42787
4. Lee, J. Y.; Kim, J. H.; Kang, S. S.; Bae, C. S.; Choi, S. H. Am. J. Chin. Med. 2004, 32, 521-530 10.1142/S0192415X04002168
5. Wang, X. F.; Yao, C. S. J. Asian Nat. Prod. Res. 2016, 18, 376-407 10.1080/10286020.2015.1094464
6. Xue, Y.-Q.; Di, J.-M.; Luo, Y.; Cheng, K.-J.; Wei, X.; Shi, Z. Oxid. Med. Cell. Longevity 2014, 15, 757-765 10.1155/2014/765832
7. Baell, J. B. J. Nat. Prod. 2016, 79, 616-628 10.1021/acs.jnatprod.5b00947
8. Bisson, J.; McAlpine, J. B.; Friesen, J. B.; Chen, S.-N.; Graham, J.; Pauli, G. F. J. Med. Chem. 2016, 59, 1671-1690 10.1021/acs.jmedchem.5b01009
9. Donnez, D.; Jeandet, P.; Clément, C.; Courot, E. Trends Biotechnol. 2009, 27, 706-713 10.1016/j.tibtech.2009.09.005
10. Jeandet, P.; Delaunois, B.; Aziz, A.; Donnez, D.; Vasserot, Y.; Cordelier, S.; Courot, E. J. Biomed. Biotechnol. 2012, 2012, 1 10.1155/2012/579089.
11. Jeandet, P.; Clément, C.; Courot, E. Eng. Life Sci. 2014, 14, 622-632 10.1002/elsc.201400022
12. Riker, A. J.; Banfield, W. M.; Wright, W. H.; Keitt, G. W.; Sagen, H. E. J. Agric. Res. 1930, 41, 507-540
13. Shams, M.; Vial, L.; Chapulliot, D.; Nesme, X.; Lavire, C. Syst. Appl. Microbiol. 2013, 36, 351-358 10.1016/j.syapm.2013.03.002
14. Georgiev, M. I.; Pavlov, A. I.; Bley, T. Appl. Microbiol. Biotechnol. 2007, 74, 1175-1185 10.1007/s00253-007-0856-5
15. Giri, A.; Narasu, M. L. Biotechnol. Adv. 2000, 18, 1-22 10.1016/S0734-9750(99)00016-6
16. Georgiev, M. I.; Agostini, E.; Ludwig-Müller, J.; Xu, J. Trends Biotechnol. 2012, 30, 528-537 10.1016/j.tibtech.2012.07.001
17. Medina-Bolivar, F.; Condori, J.; Rimando, A. M.; Hubstenberger, J.; Shelton, K.; O'Keefe, S. F.; Bennett, S.; Dolan, M. C. Phytochemistry 2007, 68, 1992-2003 10.1016/j.phytochem.2007.04.039
18. Nopo-Olazabal, C.; Hubstenberger, J.; Nopo-Olazabal, L.; Medina-Bolivar, F. J. Agric. Food Chem. 2013, 61, 11744-11758 10.1021/jf400760k
19. Tassoni, A.; Fornalè, S.; Franceschetti, M.; Musiani, F.; Michael, A. J.; Perry, B.; Bagni, N. New Phytol. 2005, 166, 895-905 10.1111/j.1469-8137.2005.01383.x
20. Taurino, M.; Ingrosso, I.; D'amico, L.; De Domenico, S.; Nicoletti, I.; Corradini, D.; Santino, A.; Giovinazzo, G. SpringerPlus 2015, 4, 49 10.1186/s40064-015-0831-z
21. Bru, R.; Sellés, S.; Casado-Vela, J.; Belchí-Navarro, S.; Pedreño, M. A. J. Agric. Food Chem. 2006, 54, 65-71 10.1021/jf051485j
22. Jeandet, P.; Clément, C.; Tisserant, L. P.; Crouzet, J.; Courot, E. C. R. Chim. 2016, 19, 1062-1070 10.1016/j.crci.2016.02.013
23. Belchí-Navarro, S.; Almagro, L.; Lijavetzky, D.; Bru, R.; Pedreño, M. A. Plant Cell Rep. 2012, 31, 81-89 10.1007/s00299-011-1141-8
24. Lijavetzky, D.; Almagro, L.; Belchi-Navarro, S.; Martinez-Zapater, J. M.; Bru, R.; Pedreno, M. A. BMC Res. Notes 2008, 1, 132-140 10.1186/1756-0500-1-132
25. Bru Martinez, R.; Pedreno Garcia, M. A. U.S. Patent 0205049 A1, 2006.
26. Walker, J. R. L.; Ferrar, P. H. Biotechnol. Genet. Eng. Rev. 1998, 15, 457-498 10.1080/02648725.1998.10647966
27. Berthod, A.; Hassoun, M.; Ruiz-Angel, M. J. Anal. Bioanal. Chem. 2005, 383, 327-340 10.1007/s00216-005-0016-7
28. Lins, A. P.; Felicio, J. D.; Braggio, M. M.; Roque, L. C. Phytochemistry 1991, 30, 3144-3146 10.1016/S0031-9422(00)98274-8
29. Sumner, L. W.; Amberg, A.; Barrett, D.; Beale, M. H.; Beger, R.; Daykin, C. A.; Fan, T. W. M.; Fiehn, O.; Goodacre, R.; Griffin, J. L.; Hankemeier, T.; Hardy, N.; Harnly, J.; Higashi, R.; Kopka, J.; Lane, A. N.; Lindon, J. C.; Marriott, P.; Nicholls, A. W.; Reily, M. D.; Thaden, J. J.; Viant, M. R. Metabolomics 2007, 3, 211-221 10.1007/s11306-007-0082-2
30. Yang, G.; Zhou, J.; Li, Y.; Hu, C. Planta Med. 2005, 71, 569-571 10.1055/s-2005-864162
31. Kulesh, N. I.; Maksimov, O. B.; Fedoreev, S. A.; Denisenko, V. A.; Glasunov, V. P.; Pokushalova, T. V.; Glebko, L. I. Chem. Nat. Compd. 1999, 35, 575-579 10.1007/BF02323300
32. Kulesh, N. I.; Isakov, V. V.; Maksimov, O. B. Chem. Nat. Compd. 1992, 28, 407-414 10.1007/BF00630640
33. Papastamoulis, Y.; Richard, T.; Nassra, M.; Badoc, A.; Krisa, S.; Harakat, D.; Monti, J. P.; Mérillon, J. M.; Waffo-Teguo, P. J. Nat. Prod. 2014, 77, 213-217 10.1021/np4005294
34. Lange, B. M.; Trost, M.; Heller, W.; Langebartels, C.; Sandermann, H. Planta 1994, 194, 143-148 10.1007/BF00201045
35. Castellano, G.; Lara, A.; Torrens, F. Phytochemistry 2014, 97, 62-69 10.1016/j.phytochem.2013.10.010
36. Vera-Urbina, J. C.; Selles-Marchart, S.; Martinez-Esteso, M. J.; Pedreno, M. A.; Bru-Martinez, R. In Resveratrol: Sources, Production and Health Benefits; Delmas, D., Ed.; Nova Science Publishers Inc: New York, 2013; Chapter 2, pp 19-40.
37. Aumont, V.; Larronde, F.; Richard, T.; Budzinski, H.; Decendit, A.; Deffieux, G.; Krisa, S.; Mérillon, J. M. J. Biotechnol. 2004, 109, 287-294 10.1016/j.jbiotec.2004.01.004
38. Donnez, D.; Kim, K. H.; Antoine, S.; Conreux, A.; De Luca, V.; Jeandet, P.; Clément, C.; Courot, E. Process Biochem. 2011, 46, 1056-1062 10.1016/j.procbio.2011.01.019
39. Houillé, B.; Papon, N.; Boudesocque, L.; Bourdeaud, E.; Besseau, S.; Courdavault, V.; Enguehard-Gueiffier, C.; Delanoue, G.; Guérin, L.; Bouchara, J. P.; Clastre, M.; Giglioli-Guivarc'h, N.; Guillard, J.; Lanoue, J. J. Nat. Prod. 2014, 77, 1658-1662 10.1021/np5002576
40. Xue, Y. Q.; Di, J. M.; Luo, Y.; Cheng, K. J.; Wei, X.; Shi, Z. Oxid. Med. Cell. Longevity 2014, 2014, 1 10.1155/2014/765832
41. Cichewicz, R. H.; Kouzi, S. A. Stud. Nat. Prod. Chem. 2002, 26, 507-579 10.1016/S1572-5995(02)80014-X