[en] Two new compounds namely acetylcaloncobaside (1) and friedocaloncobic acid (2) were isolated from the leaves of Caloncoba welwitschii together with six known compounds. Their structures were determined by standard spectroscopic methods including one- and two-dimensional NMR, EI-MS, and HRESIMS. The new compounds were established as kaempferol 4′,7-dimethoxy-3-O-(3″,4″,6″-O-triacetyl)-β-null-glucopyranoside (1) and 15β-hydroxy-3-oxo-28-friedelanoic acid (2). The isolated compounds were evaluated for their ability to inhibit the 3D7 strain of Plasmodium falciparum, using the semi-automated in vitro model with parasite lactate dehydrogenase assay.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Douanla, Pascal D.
Tchuendem, Marguerite Hortence K.
Tchinda, Alembert T.
Kuiate, Turibio
Zofou, Denis
Cieckiewicz, Ewa ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Nkengfack, Augustin E.
Language :
English
Title :
Chemical Constituents of the Leaves of Caloncoba welwitschii Gilg.
Akihisa, T., Kokke, W.C.M.C., Tamura, T., Matsumoto, T., Sterols of Kalanchoepinnata: first report of the isolation of both C-24 epimers of 24-alkyl-Δ25-sterols from a higher plant. Lipids 26 (1991), 660–665.
Burkill, H.M. 1994. The Useful Plants of West Tropical Africa, Vol 2. Royal Botanic Gardens, Kew. Chaturvedula, V. S. P., Prakash, I., 2012. Isolation of stigmasterol and β-sitosterol from the dichloromethane extract of Rubus suavissimus. Int. Curr. Pharm. J. 1, 239–242.
Clausen, V., Frydenvang, K., Koopmann, R., Jorgersen, L.B., Abbiw, D.K., Ekpe, P., Jaroszweski, J.W., Plant analysis by butterflies: occurrence of cyclopentenylglycines in Passifloraceae, Flacourtiaceae and Turneraceae and discovery of the novel nonproteinogenic amino acid 2'-(3'-cyclopentenyl) glycine in Rinorea. J. Nat. Prod. 65 (2002), 542–547.
Desjardins, R.E.T., Canfield, C.J., Haynes, J.D., Chulay, J.D., Quantitative assessment of antimalarial activity in vitro by a semi-automated microdilution technique. Antimicrob. Agents Chemother. 16 (1978), 710–718.
Fathy, M.S., Afaf, H.S., Amal, E.K., Shahera, M.E., An Acylated Kaempferol Glycoside from Flowers of Foeniculum vulgare and F. Dulce. Molecules 7 (2002), 245–251.
Giner-Pons, R.M., Gray, A.I., Lavaud, C., Massiot, G., Gibbons, S., Waterman, P.G., 30-Norfriedelane triterpenes from the stem bark of Caloncoba glauca. Phytochemistry 31 (1992), 223–225.
Giner-Pons, R.M., Gray, A.I., Gibbons, S., Waterman, P.G., Friedelane triterpenes from the stem bark of Caloncoba glauca. Phytochemistry 33 (1993), 237–239.
Hang, N.T.M., Chien, N.Q., Hung, N.V., Triterpenes from the leaves of the Vietnamese plant Calophyllum inophyllum L. J. Chem. 44 (2006), 115–118.
Harborne, J.B., Mabry, T.J., Mabry, H., The Flavonoids I. 1975, Academic Press, New York, 192.
Hutchinson, J., Dalziel, J.M., Flora of West Tropical Africa, 1, 1954, H.M.S.O, London (revised by Keay, R.W.J.) p. 189.
Mabry, T.J., Markham, K.R., Thomas, M.B., The Systemic Identification of Flavonoids. 1970, Springer-Verlag, New York Heidelberg Berlin.p.187.
Mahato, S.B., Kundu, A.P., 13C NMR spectra of pentacyclic triterpenoids–a compilation and some salient features. Phytochemistry 37 (1994), 1517–1575.
Mpetga, J.D.S., Tene, M., Wabo, H.K., Li, S.-F., Kong, L.-M., He, H.-P., Hao, X.-J., Tane, P., Cytotoxic cycloartanes from the fruits of Caloncoba glauca. Phytochem. Lett. 5 (2012), 183–187.
Mpetga, J.D.S., Shen, Y., Tane, P., Li, S.-F., He, H.-P., Wabo, H.K., Tene, M., Leng, Y., Hao, X.-J., Cycloartane and friedelane triterpenoids from the leaves of Caloncoba glauca and their evaluation for inhibition of 11β-hydroxysteroid dehydrogenases. J. Nat. Prod. 75 (2012), 599–604.
Mpetga, J.D.S., He, H.-P., Hao, X.-J., Leng, Y., Tane, P., Further cycloartane and friedelane triterpenoids from the leaves of Caloncoba glauca. Phytochem. Lett. 7 (2014), 52–56.
Mustafa, K., Nurettin, Y., Hasan, B.S., Hasan, G., Flavonol glycosides from Consolida armeniaca. Turk. J. Chem. 24 (2000), 191–197.
Raponder-Walker, A., Sillans, R., Le Chevalier, Paul, (eds.) Plantes Utiles Du Gabon, 1961 Paris VI, p. 181.
Tchuendem, M.H.K., Ayafor, J.F., Connolly, J.D., Lophocarpin and 21β-hydroxylophocarpin, two new 30-norfriedelane triterpenes from Caloncoba lophocarpa. Nat. Prod. Lett. 9 (1996), 27–32.
Trager, W., Jensen, J., Human malaria parasites in continuous culture. Science 190 (1976), 673–675.
Zhang, J., Ding, A.W., Li, Y.B., Qian, D.W., Duan, J.A., Yin, Z.Q., Two new flavonoid glycosides from Chrysanthemum morifolium. Chin. Chem. Lett. 17 (2006), 1051–1053.
Ziegler, H.L., Staerk, D., Christiensen, J., Olsen, C.E., Sittie, A.A., Jarosweski, J.W., New dammarane and malabaricane triterpenes from Caloncoba echinata. J. Nat. Prod. 65 (2002), 1764–1765.
Zofou, D., Kengne, A.B.O., Tene, M., Ngemenya, M.N., Tane, P., Titanji, V.P.K., In vitro antiplasmodial activity and cytotoxicity of crude extracts and compounds from the stem bark of Kigelia africana (Lam.) Benth (Bignoniaceae). Parasitol. Res. 108 (2011), 1383–1390.
Zofou, D., Nyasa, R.B., Nsagha, D.S., Ntie-Kang, F., Meriki, H.D., Assob, J.C., Kuete, V., Control of malaria and other vector-borne protozoan diseases in the tropics: enduring challenges despite considerable progress and achievements. Infect. Dis. Poverty, 3, 2014, 1.