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Copyright (c) 2014 B. Ngameni1, G.W. Fotso2, E. Ngachussi2, H.M. Poumale Poumale2, B.T. Ngadjui2, Y. Shiono3, T. Murayama3
This work is licensed under a Creative Commons Attribution 4.0 International License.
Hemisynthesis and Spectroscopic Characterization of Two Novel O-Allylated Benzophenones from Garcinia punctata Oliv. (Clusiaceae)
Corresponding Author(s) : B. Ngameni1
Asian Journal of Chemistry,
Vol. 26 No. 20 (2014)
Abstract
Four known natural compounds i.e., (-) isogarcinol, (+) 7-epigarcinol, stigmasterol and b-sitosterol-3-O-b-D-glucoside were isolated from the stem bark of Garcinia punctata oliv. From (-) isogarcinol, two new hemisynthesis O-allylated benzophenones were synthesized using allylbromide in the presence of potassium carbonate in anhydrous acetone. The structural elucidation of all the compounds was done by mass spectrometry, IR, 1D- and 2D-NMR analysis and also by comparison with previous reports. This is the first study to report on the one step allylation of the natural (-) isogarcinol using the base catalysis conditions.
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References
P.S. Bailey and C.A. Bailey, Organic Chemistry, Prentice-Hall Inc, New Jersey, edn 5 (1995).
R. Ciochina and R.B. Grossman, Chem. Rev., 106, 3963 (2006).
Y.H. Li, Flora Reipublicae Popularis Sinicae, Science Press, Beijing, pp 89-110 (1990).
M.M. Iwu, A.D. Diop, L. Meserole and O.C. Okunji, Ethnomed. Drug Discovery, 1, 191 (2002).
K.R. Gustafson, J.W. Blunt, M.H.G. Munro, R.W. Fuller, T.C. McKee, J.H. Cardellina II, J.B. McMahon, G.M. Cragg and M.R. Boyd, Tetrahedron, 48, 10093 (1992).
S.X. Huang, C. Feng, Y. Zhou, G. Xu, Q.B. Han, C.F. Qiao, D.C. Chang, K.Q. Luo and H.X. Xu, J. Nat. Prod., 72, 130 (2009).
M. Masullo, C. Bassarello, H. Suzuki, C. Pizza and S.J. Piacente, Agric. Food Chem., 56, 5205 (2008).
J. Hong, S.J. Kwon, S. Sang, J. Ju, J.N. Zhou, C.T. Ho, M.T. Huang and C.S. Yang, Free Radic. Biol. Med., 42, 1211 (2007).
H.M. Burkill, The Useful Plants of West Tropical Africa, Families E-I. Royal Botanic Gardens Kew, edn 2. Vol. 2, pp. ISBN No. 0-947643-56-7 (1994).
S. Mukherjee, V. Kumar, A.K. Prasad, H.G. Raj, M.E. Bracke, C.E. Olsen, S.C. Jain and V.S. Parmar, Bioorg. Med. Chem., 9, 337 (2001).
G. Marti, V. Eparvier, C. Moretti, S. Prado, P. Grellier, N. Hue, O. Thoison, B. Delpech, F. Guéritte and M. Litaudon, Phytochemistry, 71, 964 (2010).
G. Marti, V. Eparvier, C. Moretti, S. Susplugas, S. Prado, P. Grellier, P. Retailleau, F. Guéritte and M. Litaudon, Phytochemistry, 70, 75 (2009).
V. Rukachaisirikul, W. Kaewnok, S. Koysomboon, S. Phongpaichit and W.C. Taylor, Tetrahedron, 56, 8539 (2000).
E. Elfita, M. Muharni, M. Latief, D. Darwati, A. Widiyantoro, S. Supriyatna, H.H. Bahti, D. Dachriyanus, P. Cos, L. Maes, K. Foubert, S. Apers and L. Pieters, Phytochemistry, 70, 907 (2009).
W. Hamed, S. Brajeul, F. Mahuteau-Betzer, O. Thoison, S. Mons, B. Delpech, N.V. Hung, T. Sevenet and C. Marazano, J. Nat. Prod., 69, 774 (2006).
A.L. Piccinelli, O. Cuesta-Rubio, M.B. Chica, N. Mahmood, B. Pagano, M. Pavone, V. Barone and L. Rastrelli, Tetrahedron, 61, 8206 (2005).
M. Iinuma, H. Tosa, T. Tanaka, S. Kanamaru, F. Asai, Y. Kobayashi, K. Miyauchi and R. Shimano, Biol. Pharm. Bull., 19, 311 (1996).
N. Krishnamurthy, Y.S. Lewis and B. Ravindranath, Tetrahedron Lett., 22, 793 (1981).
S. Baggett, E.P. Mazzola and E.K. Kennelly, Studies Nat. Prod. Chem., 32, 721 (2005).