A New Cycloheptapeptide from Zanthoxylum mezoneurispinosum Aké Assi (Rutaceae)

Authors

  • Philomene A. Yao-Kouassi Groupe Isolement et Structure, Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, CPCBAI, Bâtiment 18, Moulin de la Housse, BP 1039, 51687 Reims Cedex, France.
  • Catherine Caron Groupe Isolement et Structure, Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, CPCBAI, Bâtiment 18, Moulin de la Housse, BP 1039, 51687 Reims Cedex, France.
  • Emma Aké-Assi Laboratoire de Botanique, Université FHB Cocody-Abidjan, 22 BP 582, Abidjan, Côte d’Ivoire.
  • Agathe Martinez Groupe Isolement et Structure, Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, CPCBAI, Bâtiment 18, Moulin de la Housse, BP 1039, 51687 Reims Cedex, France.
  • Elisabeth Le Magrex-Debar Laboratoire de Microbiologie, EA "Biomatériaux et Inflammation en site osseux" UFR de Pharmacie, 1, Rue du Maréchal Juin, 51096 Reims Cedex, France.
  • Sophie C. Gangloff Laboratoire de Microbiologie, EA "Biomatériaux et Inflammation en site osseux" UFR de Pharmacie, 1, Rue du Maréchal Juin, 51096 Reims Cedex, France.
  • Monique Zéches-Hanrot Groupe Isolement et Structure, Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, CPCBAI, Bâtiment 18, Moulin de la Housse, BP 1039, 51687 Reims Cedex, France.

DOI:

https://doi.org/10.13171/mjc.3.5.2014.10.10.16.08

Abstract

A new cycloheptapeptide named akeassimezorine 1 and twelve known compounds: methoxy-chelerythrine 2, chelerythrine 3, nitidine 4, methoxyfagaridine 5, jatrorrhizine 6, tembetarine 7, N-methylatanine 8, magnoflorine 9, skimmianine 10, sesamine 11, hesperidine 12, and lupeol 13 were isolated from the roots of Zanthoxylum mezoneurispinosum Aké Assi (Rutaceae). The structures of those compounds were elucidated on the basis of one- and two-dimensional NMR and HR-ESI-MS analyses. Antibacterial activity of compound 1 was evaluated against pathogenic agents. This study constituted the first phytochemical investigation of the roots of Zanthoxylum mezoneurispinosum.

References

- D. J. Mabberly; The plant book: a portable dictionary of the higher plant. Cambridge University Press, 1987, 707.

- M. J. Cheng, I. L. Tsai and I. S. Chen, J. Chin. Chem. Soc., 2003, 50, 1241-1246.

- E. J. Adjanohoun, Contribution aux études ethnobotaniques et floristiques au Togo, Paris, France, A.C.C.T, 1986, 671.

- I. Elekwa, M. O. Monanu and E. O. Anosike, Biokemistri, 2005, 17, 7-12.

- O. M. Adegbolagun and O. O. Olukemi, Afr. J. Pharm. Pharmaco, 2010, 4, 145-150.

- O. J. Patiño, J. A. Prieto, J. M. Lozano, L. Lesmes and L. E. Cuca, Rev. Cubana Fram. 2011, 45, 431-438.

- N. Verma and R. L. Khosa, IJBB, 2010, 47, 124-127.

- J. Arrieta, B. Reyes, F. Calzada, R. Cedillo-Rivera and A. Navarrete, Fitoterapia, 2001, 72, 295-297.

- P. A. Olounlade, E. V. Azando, M. S. Hounzangbe-Adote, T. B. Ha, E. Leroy, C. Moulis, N. Fabre, J. F. Magnaval, H. Hoste and A. Valentin, Parasitol. Res., 2012, 110, 1427-1433.

- J. J. Chen, Y. H. Lin, S. H. Day, T. L. Hwang and I. S. Chen, Food Chem., 2011, 125, 282-287.

- F. Hiroyuki, K. Marii, M. Y. Kanami, S. Setsuko, S. Motoyoshi, I. Tsutomu, K. Fumiyuki and K. Nobuo, Chem. Pharm. Bull., 2010, 8, 1047-1050.

- F. Batool, S. S. Mubashir, J. B. T. Rocha, A. S. Hussain, Z. S. Saied and S. A. Dilnawad, PJB, 2010, 42, 4299-4311.

- L. Xia, J. You, G. Li, Z. Sun and Y. Suo, J. Am. Oil Chem. Soc., 2011, 88, 1029-1036.

- L. T. Tan, Phytochemistry, 2007, 68, 954-979.

- K. Tidgewell, N. Engene, T. Byrum, J. Media, T. Doi, F. A. Valeriote and W. H. Gerwick, Chem. Bio. Chem., 2010, 11, 1458-1466.

- A. Wélé, Y. Zhang, C. Caux, J. P. Brouard, L. Dubost, C. Guette, J. L. Pousset, M. Badiane and B. Bodo, J. Chem. Soc. Perkin Trans I, 2002, 2712-2718.

- A. Wélé, Y. Zhang, I. Ndoye, J. P. Brouard, J. L. Pousset and B. Bodo, J. Nat. Prod., 2004, 67, 1577-1579.

- A. N. T. Ribeiro, R. L. Da Silva, T. de S. P. Junior, N. R. Castro and G. M. A. De Carvalho, Helv. Chim. Acta, 2012, 95, 935-939.

- M. F. Talontsi, P. Facey, K. M. D. Tatong, T. M. Islam, H. Frauendorf, S. Draeger, A. Von Tiedemann and H. Laatsch, Phytochemistry, 2012, 83, 87-94.

- P. Marfey, Carlsberg Res. Commun., 1984, 49, 591-596.

- M. Grare, M. Mourer, J. B. Regnouf-de-Vains, C. Finance and R. E. Duval, Pathol. Biol., 2006, 54, 470-476.

- A. P. Yao-Kouassi, A. A. Magid, B. Richard, A. Martinez, M. J. Jacquier, C. Caron, D. E. Le Magrex, C. S. Gangloff, C. A. Ahiboand M. Zèches-Hanrot, J. Nat. Prod., 2008, 71, 2073-2076.

- N. Keawpradub, S. Dej-Adisaiand S. Yuenyongsawad,Songklanakarin J. Sci. Technol., 2005, 27 (Suppl.2), 455-467.

- H. Mozammel, B. Sufia, S. Hossain, A. Monira, M. H. Choudhury, A. Nuruddin and H. Rashedul, Pharmacogn. Mag., 2013, 9, 76-80.

- J. A Swinehart and F. R. Stermitz, Phytochemistry, 1980, 19, 1219-1223.

- J. M. Barbosa-Filho, E. V. L. Da-Cunha, M. L. Cornélio, C. D. Da Silva and A. I. Gray, Phytochemistry, 1997, 44, 959-961.

- E. Hisatomi, M. Matsui, A. Kobayashi and K. Kubota, J. Agric. Food Chem., 2000, 48, 4924-4928.

- A. P. Yao-Kouassi, A. Martinez, D. F. Malan, D. E. Le Magrex, C. S. Gangloff, C. Caron, C. A. Ahibo and M. Zèches-Hanrot, Int. J. Biol. Chem. Sci., 2014, 8, 377-385.

- D. E. Dorman and F. A. Bovey, J. Org. Chem., 1973, 38, 2379-2383.

- K. Wüthrich, M. Billeter and W. Braun, J. Mol. Biol., 1984, 180, 715-740.

- N. H. Tan and J. Zhou, Chem. Rev., 2006, 106, 840-895.

Published

2014-10-10

Issue

Section

Phytochemistry