Two new alkylresorcinol derivatives from the leaves of Scyphocephalium ochocoa
-
Hibrahim Foundikou
Abstract
Two new alkylresorcinol derivatives, namely ochocinone A and ochocinone B (1, 2), as well as a known alkylresorcinol oleiferinone (3) were isolated from the methanol extract of the leaves of Scyphocephalium ochocoa. The structures of these compounds were established by detailed spectroscopic analysis and by comparison with the spectral data of related known compounds. Compounds 1–3 showed significant immunomodulatory activity and cytotoxic effect on the mammary carcinoma MCF-7 cell line.
Acknowledgments
The authors thank Mr. Yves Issembe, the National Herbarium of Gabon, Libreville, Gabon. They are indebted to the International Center for Chemical and Biological Sciences, University of Karachi, for recording the spectral data and for providing the facilities for the biological analysis. This work was supported by the financial assistance of the International Foundation for Science (IFS) through the grants No. F-4738 “1 and 2” (GRFT). The research stay in Pakistan was sponsored through the TWAS and TWAS–UNESCO Associateship Scheme fellowships (HF and GRFT).
Competing interests: The authors declare that they have no competing interests.
References
[1] G. R. Feuya Tchouya, A. Souza, J. C. Tchouankeu, J. F. Yala, M. Boukandou, H. Foundikou, G. D. N. Obiang, F. F. Boyom, R. M. Mabika, E. Zeuko, J. Ethnopharmacol. 2015, 162, 306.10.1016/j.jep.2014.12.052Suche in Google Scholar
[2] A. R. Walker, R. Sillans, in Les plantes utiles du Gabon (Ed.: P. Lechevalier), Sépia, Paris, 1961.Suche in Google Scholar
[3] L. I. Filippin, R. Vercelino, N. P. Marroni, R. M. Xavier, Clin. Exp. Immunol.2008, 152, 415.10.1111/j.1365-2249.2008.03634.xSuche in Google Scholar
[4] M. Ahmed, J. Almas, A. H. Sobia, B. Afshan, A. K. Shukralla, A. Muhammad, F. Beenish, U. H. Zaheer, M. C. Iqbal, Chem. Biol. Drug. Des.2012, 79, 290.10.1111/j.1747-0285.2011.01310.xSuche in Google Scholar
[5] J. Arnhold, Biochemistry2004, 69, 4.10.1023/B:BIRY.0000016344.59411.eeSuche in Google Scholar
[6] G. R. Feuya Tchouya, H. Foundikou, J. Lebibi, M. I. Choudhary, E. Z. Menkem, E. A. Nantia, J. J. B. Kezetas, J. C. Tchouankeu, J. Pharmacogn. Nat. Prod. 2015, 1, 111.Suche in Google Scholar
[7] J. F. Hu, E. Garo, H. D. Yoo, P. A. Cremin, M. G. Goering, M. O’Neil-Johnson, G. R. Eldridge, Phytochemistry2005, 66, 1077.10.1016/j.phytochem.2005.03.014Suche in Google Scholar
[8] M. F. Mahomoodally, A. Gurib-Fakim, A. H. Subratty, J. Ethnopharmacol.2007, 110, 257.10.1016/j.jep.2006.09.020Suche in Google Scholar
[9] M. A. Mesaik, Z. U. Haq, S. Murad, Z. Ismail, N. R. Abdullah, H. K. Gill, A. U. Rahman, M. Yousaf, R. A. Siddiqui, A. Ahmad, M. I. Choudhary, Mol. Immunol. 2006, 43, 1855.10.1016/j.molimm.2005.10.020Suche in Google Scholar
[10] U. Singh, T. James, K. V. Senthil, D. Sridevi, J. Ishwarlal, Clin. Chem.2005, 51, 2252.10.1373/clinchem.2005.056093Suche in Google Scholar
[11] S. Inoue, S. I. Itagaki, F. Amano, Infect. Immun.1995, 63, 1876.10.1128/iai.63.5.1876-1886.1995Suche in Google Scholar
[12] T. Mosmann, J. Immunol. Methods. 1983, 65, 55.10.1016/0022-1759(83)90303-4Suche in Google Scholar
[13] S. Verma, E. Vashishth, R. Singh, A. Kumari, A. Meena, P. Pant, G. Bhuyan, M. Padhi, Res. J. Pharm. Technol. 2013, 6, 1307.Suche in Google Scholar
[14] G. Viswanadh, P. Ramaiah, H. Laatsch, R. Maskey, J. Trop. Med. Plant. 2006, 7, 267.Suche in Google Scholar
[15] N. R. Azevedo, S. C. Santos, E. G. De Miranda, P. H. Ferri, Phytochemistry1997, 46, 1375.10.1016/S0031-9422(97)00503-7Suche in Google Scholar
[16] M. J. G. Gonzalez, C. J. DeOliveira, J. Fernandes, A. Kijjoa, W. Herz, Phytochemistry1996, 43, 1333.10.1016/S0031-9422(96)00413-XSuche in Google Scholar
[17] M. J. Kato, L. M. Lopes, H. F. P. Fo, M. Yoshida, O. R. Gottlieb, Phytochemistry1985, 24, 533.10.1016/S0031-9422(00)80762-1Suche in Google Scholar
[18] P. Van Cuong, J. Akino, S. Thierry, B. Benardo, Tetrahedron2000, 56, 1707.10.1016/S0040-4020(00)00074-0Suche in Google Scholar
[19] R. A. Neucirio, C. S. Suzana, G. D. M. Euripedes, H. F. Pedro, Phytochemistry1997, 46, 1375.10.1016/S0031-9422(97)00503-7Suche in Google Scholar
[20] M. J. Cheng, S. J. Lee, Y. Y. Chang, S. H. Wu, I. L. Tsai, B. Jayaprakasam, I. S. Chen, Phytochemistry2003, 63, 603.10.1016/S0031-9422(03)00183-3Suche in Google Scholar
[21] R. R. Bartlett, M. Dimitrijevic, T. Mattar, T. Zielinski, T. Germann, Agents Actions1991, 32, 10.10.1007/BF01983301Suche in Google Scholar PubMed
[22] I. Jantan, N. H. Harun, A. W. Septama, S. Murad, M. A. Mesaik, J. Nat. Med. 2011, 65, 400.10.1007/s11418-010-0492-8Suche in Google Scholar PubMed
[23] T. Linn, H. Germann, R. G. Bretzel, K. Helmke, U. Bicker, J. Diabetes Res.1987, 4, 121.Suche in Google Scholar
[24] G. E. B. El Ghazali, M. S. El Tohami, A. A. B. El Egami, W. E. Abdalla, G. Mohamed, Medicinal Plants of Sudan, Part II, Medicinal Plants of Northern Kordofan, Khartoum University Press, Khartoum, 1994.Suche in Google Scholar
[25] J. Marx, Science2000, 306, 966.10.1126/science.306.5698.966Suche in Google Scholar PubMed
[26] N. M. Sodir, L. B. Swigart, A. N. Karnezis, D. Hanahan, G. I. Evan, L. Soucek, Genes Dev.2011, 25, 907.10.1101/gad.2038411Suche in Google Scholar PubMed PubMed Central
[27] F. R. Balkwill, A. Mantovani, Cancer Immunother. 2012, 22, 33.10.1016/j.semcancer.2011.12.005Suche in Google Scholar
[28] T. E. Reichert, L. Strauss, E. M. Wagner, W. Gooding, T. L. Whiteside, Clin. Cancer Res. 2002, 8, 3137.Suche in Google Scholar
[29] A. Ben-Baruch, Semin. Cancer Biol. 2006, 16, 38.10.1016/j.semcancer.2005.07.006Suche in Google Scholar PubMed
[30] R. Barrow, R. Capon, Aust. J. Chem.1991, 44, 1393.10.1071/CH9911393Suche in Google Scholar
[31] X. Wang, W. Qu, J. Liang, Nat. Prod. Res. 2013, 27, 796.10.1080/14786419.2012.704373Suche in Google Scholar PubMed
[32] P. H. Dang, H. X. Nguyen, N. T. Nguyen, H. N. T. Le, M. T. T. Nguyen, Phytother. Res.2014, 28, 1632.10.1002/ptr.5175Suche in Google Scholar PubMed
[33] A. Kozubek, S. Pietr, A. Czerwonka, J. Bacteriol.1996, 178, 4027.10.1128/jb.178.14.4027-4030.1996Suche in Google Scholar PubMed PubMed Central
[34] E. Zarnowska, R. Zarnowski, A. Kozubek, Z. Naturforsch. C2000, 55c, 881.10.1515/znc-2000-11-1206Suche in Google Scholar PubMed
[35] R. Zarnowski, T. Lewicka, S. Pietr, Z. Naturforsch. C2000, 55c, 846.10.1515/znc-2000-9-1030Suche in Google Scholar PubMed
[36] M.-J. Cheng, I.-S. Chen, J. Chil. Chem. Soc.2008, 53, 1539.10.4067/S0717-97072008000200021Suche in Google Scholar
[37] M. A. Othman, Y. Sivasothy, C. Y. Looi, A. Ablat, J. Mohamad, M. Litaudon, K. Awang, Fitoterapia2016, 111, 12.10.1016/j.fitote.2016.04.004Suche in Google Scholar PubMed
[38] A. B. Ross, A. Kamal-Eldin, P. Åman, Nutr. Rev.2004, 62, 81.10.1111/j.1753-4887.2004.tb00029.xSuche in Google Scholar PubMed
[39] A. Kozubek, J. Tyman, Chem. Rev. 1999, 99, 1.10.1021/cr970464oSuche in Google Scholar PubMed
[40] R. Zarnowski, A. Kozubek, S. Pietr, Bull. Pol. Acad. Sci., Biol.1999, 47, 231.Suche in Google Scholar
Supplementary Material:
The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2018-0008).
©2018 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- In this Issue
- Influence of different metal ions on the assembly, structures, and properties of two complexes based on the semi-rigid bis(pyridyl)-bis(amide) ligand and 4,4′-oxybis(benzoic acid)
- Structural, spectral and docking studies of a coordination polymer of zinc(II) formed by a pyridine-derived linker
- The isolation and structural elucidation of a new iridoid glycoside from Cymbaria dahurica L.
- Two new alkylresorcinol derivatives from the leaves of Scyphocephalium ochocoa
- Synthesis and antimicrobial evaluation of some heterocyclic compounds from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes
- Studying the reactivity of N-2-(2-aminobenzoyl)-N-phenyl-hydrazinecarbothioamide toward some selected carbonyl compounds
- A Zn(II) complex from an imidazolyl-thiophene ligand: synthesis, structural characterization, and fluorescence
- A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin
- Synthesis, structural characterization, and properties of Ag(I) complexes with N-donor ligands
Artikel in diesem Heft
- Frontmatter
- In this Issue
- Influence of different metal ions on the assembly, structures, and properties of two complexes based on the semi-rigid bis(pyridyl)-bis(amide) ligand and 4,4′-oxybis(benzoic acid)
- Structural, spectral and docking studies of a coordination polymer of zinc(II) formed by a pyridine-derived linker
- The isolation and structural elucidation of a new iridoid glycoside from Cymbaria dahurica L.
- Two new alkylresorcinol derivatives from the leaves of Scyphocephalium ochocoa
- Synthesis and antimicrobial evaluation of some heterocyclic compounds from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes
- Studying the reactivity of N-2-(2-aminobenzoyl)-N-phenyl-hydrazinecarbothioamide toward some selected carbonyl compounds
- A Zn(II) complex from an imidazolyl-thiophene ligand: synthesis, structural characterization, and fluorescence
- A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin
- Synthesis, structural characterization, and properties of Ag(I) complexes with N-donor ligands