The hemisynthesis of three new chalcones, namely kenzanol, kelianol A, and kelianol B, from Dorstenia barteri (Moraceae) is described here for the first time. The synthetic pathways employed in this work involved the pyrolysis and catalytic hydrogenation of readily available and starting materials, 4-hydroxylonchocarpin and isobavachalcone, two major constituents of the herbaceous plant D. barteri. The structural elucidation of all the compounds was done by mass spectrometry, IR, UV, 1D and 2D NMR analysis, and also by comparison with previous reports.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. Jurasek, V. Knoppava, M. Dandarova, A. Kovac, and J. Reinprecht, Tetrahedron, 34, 1883 (1978).
G. V. Subbraju, A. R. Nayakulu, and D. Parameshwara, Ind. J. Heterocycl. Chem., 4, 87 (1994).
B. A. Bhat, K. L. Dhar, S. C. Puri, A. K. Saxena, M. Shanmugavel, and G. N. Qazi, Bioorg. Med. Chem. Lett., 15, 3177 (2005).
J. N. Dominguez, C. J. Rodrigues, N. Gamboa de Dominguez, J. Gut, J. Philip, and P. Rosenthal, J. Farmaco, 60, 307 (2005).
N. Yauli, O. Ucuncu, E. Aydin, Y. Gok, A. Yaar, C. Baltaci, N. Yildirim, and M. Kucuk, J. Photochem. Photobiol. A: Chem., 169, 229 (2005).
S. Khatib, O. Narya, R. Musa, M. Shmuel, S. Tamir, and J. Vaya, Bioorg. Med. Chem., 13, 433 (2005).
B. Ngameni, M. Touaibia, A. Belkaid, P. Ambassa, J. Watchueng, R. Patnam, B. T. Ngadjui, B. Annabi, and R. Roy, Arkivoc, ix, 91 (2007).
H. N. ElSohly, A. S. Joshi, A. C. Nimrod, L. A. Walker, and A. M. Clark, Planta Med., 67, 87 (2001).
B. Ngameni, M. Touaibia, R. Patnam, A. Belkaid, P. Sonna, B. T. Ngadjui, B. Annabi, and R. Roy, Phytochemistry, 67, 2573 (2006).
B. Ngameni, J. Watchueng, B. F. Fekam, F. Keumedjio, B. T. Ngadjui, J. Gut, M. B. Abegaz, and J. P. Rosenthal, Arkivoc, xiii, 116 (2007).
V. Kuete, B. Ngameni, A. T. Mbaveng, B. T. Ngadjui, J. J. M. Meyer, and N. Lall, Acta Tropica, 116, 100 (2010).
B. M. Abegaz, B. T. Ngadjui, E. Dongo, and H. Tamboue, Phytochemistry, 49, 1147 (1998).
M. S. Rao, P. S. Rao, B. Balazs, and H. Duddeck, J. Nat. Prod, 61, 1148 (1998).
B. T. Ngadjui, G. W. F. Kapche, H. Tamboue, B. M. Abegaz, and J. D. Connolly, Phytochemistry, 51, 119 (1999).
B. T. Ngadjui, S. F. Kouam, E. Dongo, G. W. F. Kapche, and B. M. Abegaz, Phytochemistry, 55, 915 (2000).
J. March, Advanced Organic Chemistry, 3rd Ed., John Wiley & Sons, New York, 1985, 125 pp.
J. Clayden, N. Greeves, S. Warren, and P. Wothers, Organic Chemistry, Oxford University Press, New York, 2001, 456 pp.
F. R. Jensen and C. H. Bushweller, J. Am. Chem. Soc., 88, 4279 (1966).
F. R. Jensen and C. H. Bushweller, J. Am. Chem. Soc., 91, 3223 (1969).
H. Chen, Y. Lin, G. Chen, G. Hu, L. Wang, and L. L. P. Vrijmoed, Chem. Nat. Compd., 42, 407 (2006).
Acknowledgment
BN and BTN are grateful to the Chemistry Department of the University of Botswana for providing research facilities. BN and AD are also thankful to the Department of Chemistry, Ataturk University, Turkey for important support with the experimental equipment.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2017, pp. 207–212.
Rights and permissions
About this article
Cite this article
Ngameni, B., Fotso, G.W., Ambassa, P. et al. Hemisynthesis and Spectroscopic Characterization of Three New Chalcone Derivatives from Dorstenia barteri . Chem Nat Compd 53, 241–247 (2017). https://doi.org/10.1007/s10600-017-1962-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-017-1962-y