Cymoside, a monoterpene indole alkaloid with a hexacyclic fused skeleton from Chimarrhis cymosa

Tetrahedron Letters

Volumn 56, Issue 40, 2015, Pages 5377-5380

  Lémus, Christelle ^a   Kritsanida, Marina ^a   Canet, Alban ^a   Genta Jouve, Grégory ^a   Michel, Sylvie ^a   Deguin, Brigitte ^a   Grougnet, Raphaël ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Chimarrhis cymosa; Cymoside; Monoterpene indole alkaloid; Rubiaceae

Indexed keywords

CYMOSIDE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; CHIMARRHIS CYMOSA; CIRCULAR DICHROISM; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PLANT LEAF; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 84940703144     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.07.066     Document Type: Article

References (32)

1. P.M. Dewick Medicinal natural products-a biosynthetic approach 3rd ed. 2009 Jonh Wiley & Sons Chichester p 369
2. M.C. Le Deley, A. Rosolen, D.M. Williams, K. Horibe, G. Wrobel, A. Attarbaschi, J. Zsiros, A. Uyttebroeck, I.M. Marky, L. Lamant, W. Woessmann, M. Pillon, R. Hobson, A. Mauguen, A. Reiter, and L. Brugières J. Clin. Oncol. 28 2010 3987 3993
3. R. Van der Heijden, D.I. Jacobs, W. Snoeijer, D. Hallard, and R. Verpoorte Curr. Med. Chem. 11 2004 607 628
4. L. Dassonneville, K. Bonjean, M.C. De Pauw-Gillet, P. Colson, C. Houssier, J. Quetin-Leclercq, L. Angenot, and C. Bailly Biochemistry 38 1999 7719 7726
5. M.E. Pesce, X. Acevedo, D. Bustamante, H.F. Miranda, and G. Pinardi Pharmacol. Toxicol. 87 2000 116 119
6. Y. Wang, P. Kruzik, A. Helsberg, I. Helsberg, and W.-D. Rausch Forensic Sci. Int. 169 2007 157 160
7. S.E. O'Connor, and J.J. Maresh Nat. Prod. Rep. 23 2006 532 547
8. A. Patthy-Lukats, L. Karolyhazy, L.F. Szabo, and B. Podanyi J. Nat. Prod. 60 1997 69 75
9. J. Stockigt, and S. Panjikar Nat. Prod. Rep. 24 2007 1382 1400
10. K. Miettinen, L. Dong, N. Navrot, T. Schneider, V. Burlat, J. Pollier, L. Woittiez, S. Van der Krol, R. Lugan, T. Ilc, R. Verpoorte, K.-M. Oksman-Caldentey, E. Martinoia, H. Bouwmeester, A. Goossens, J. Memelink, and D. Werck-Reichhart Nat. Commun. 5 2014 1 11
11. C.L. Cardoso, I. Castro-Gamboa, D.H.S. Silva, M. Furlan, R.d.A. Epifanio, A.d.C. Pinto, C. Moraes de Rezende, J.A. Lima, and V.d.S. Bolzani J. Nat. Prod. 67 2004 1882 1885
12. C.L. Cardoso, D.H.S. Silva, I. Castro-Gamboa, and V.d.S. Bolzani J. Braz. Chem. Soc. 16 2005 1353 1359
13. C.L. Cardoso, V.d.S. Bolzani, D.H.S. Silva, H. Ishii, N. Berova, and K. Nakanishi J. Nat. Prod. 69 2006 1046 1050
14. C.L. Cardoso, D.H.S. Silva, M.C.M. Young, I. Castro-Gamboa, and V.d.S. Bolzani Rev. Bras. Farmacogn. 18 2008 26 29
15. C.L. Cardoso, I. Castro-Gamboa, G.M. Bergamini, A.J. Cavalheiro, D.H.S. Silva, M.N. Lopes, A.R. ArauÌjo, M. Furlan, H. Verli, and V.d.S. Bolzani J. Nat. Prod. 74 2011 487 491
16. C.L. Cardoso, D.H. Siqueira Silva, D.M. Tomazela, H. Verli, M.C.M. Young, M. Furlan, M.N. Eberlin, and V. da Silva Bolzani J. Nat. Prod. 66 2003 1017 1021
17. Missouri botanical garden http://www.tropicos.org (accessed Apr 7, 2014).
18. Amorphous white powder; [α]20D +190 (c 0.011, MeOH); UV (MeOH) λmax (Log ε) 245 (2.45), 275 (2.78) nm; IR νmax 3315, 2917, 1717, 1611, 1466, 1434, 1397, 1319, 1260, 1139, 1067, 1009, 858, 804, 747 cm-1; 1H and 13C NMR spectroscopic data, see Table 1; ESIMS m/z 547.1 [M+H]+, m/z 569.2 [M+Na]+; HRESIMS m/z 547.2293 [M+H]+ (calcd for C27H35O10N2 547.2292).
19. P.A. Cockrum, S.M. Colegate, J.A. Edgar, K. Flower, D. Gardner, and R.I. Willing Phytochemistry 51 1999 153 157
20. X.-H. Cai, M.-F. Bao, Y. Zhang, C.-X. Zeng, Y.-P. Liu, and X.-D. Luo Org. Lett. 13 2011 3568 3571
21. J. Schinnerl, E.A. Orlowska, E. Lorbeer, A. Berger, and L. Brecker Phytochem. Lett. 5 2012 586 590
22. P. Hanhinen, T. Nurminen, R. Jokela, and M. Lounasmaa Heterocycles 38 1994 2027 2044
23. M.A. Beniddir, M.-T. Martin, M.-E. Tran Huu Dau, P. Grellier, P. Rasoanaivo, F. Gueritte, and M. Litaudon Org. Lett. 14 2012 4162 4165
24. N. Cachet, G. Genta-Jouve, E.L. Regalado, R. Mokrini, P. Amade, G. Culioli, and O.P. Thomas J. Nat. Prod. 72 2009 1612 1615
25. G. Genta-Jouve, L. Weinberg, V. Cocandeau, Y. Maestro, O.P. Thomas, and S. Holderith Chirality 25 2013 180 184
26. X.-H. Cai, Y. Li, Y.-P. Liu, X.-N. Li, M.-F. Bao, and X.-D. Luo Phytochemistry 83 2012 116 124
27. S. Uzir, A.M. Mustapha, A.H.A. Hadi, K. Awang, C. Wiart, J.-F. Gallard, and M. Païs Tetrahedron Lett. 38 1997 1571 1574
28. K. Ghedira, M. Zeches-Hanrot, B. Richard, G. Massiot, L. Le Men-Olivier, T. Sevenet, and S.H. Goh Phytochemistry 27 1988 3955 3962
29. N.M. Pérez, F.B. Torrico, and A. Morales J. Ethnopharmacol. 143 2012 599 603
30. X.-H. Cai, Q.-G. Tan, Y.-P. Liu, T. Feng, Z.-Z. Du, W.-Q. Li, and X.-D. Luo Org. Lett. 10 2008 577 580
31. Y. Hirasawa, S. Miyama, T. Hosoya, K. Koyama, A. Rahman, I. Kusumawati, N.C. Zaini, and H. Morita Org. Lett. 11 2009 5718 5721
32. N. Kogure, N. Ishii, M. Kitajima, S. Wongseripipatana, and H. Takayama Org. Lett. 8 2006 3085 3088