Document Type : Original Article

Authors

1 Department of Chemistry, Higher Teacher Training College, University of Bamenda, P.O Box 39, Bambili, Cameroon

2 Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany

3 Department of Chemistry, Higher Teacher Training College, University of Yaounde I, P. O. Box 47, Yaounde, Cameroon

4 Department of Organic Chemistry, Faculty of Sciences, University of Yaounde I, P.O. Box 812, Yaounde, Cameroon

10.30495/tpr.2021.680493

Abstract

A new phenylpropanoid glycoside named psorospermoside (1) possessing an allose unit was isolated from the Psorospermum tenuifolium Hook f. bark extract together with eleven known compounds. Their structures were elucidated using spectroscopic and spectrometric methods including 1D, 2D-NMR, and ESI-MS, as well as by comparison of their data with those reported in the literature. All the isolated compounds were assessed for their cytotoxicity effect on the human cervix carcinoma cell line KB3-1. Emodin (2) and its congener 2-geranylemodin (3) displayed significant cytotoxicity with IC50 values of 11.4 µM and 19.0µM, respectively. Furthermore, the chemotaxonomic significance of the isolated compounds was also discussed.

Graphical Abstract

A new phenylpropanoid glucoside from Psorospermum tenuifolium Kotschy (Hypericaceae)

Keywords

African plant database (version 3.4.0), accessed on 2019 December 18, http://www.ville-ge.ch/musinfo/bd/cjb/africa/.
Amonkar, A., Chang, C.J., Cassady, J.M., 1981. 6-Geranyloxy-3-methyl-1,8-dihydroxanthone, a novel antileukemic agent from Psorospermum febrifugum Spach var. ferrugineum (Hook. fil). Experientia 37, 1138-1139.
Bisoli, E., Garcez, W.S., Hamerski, L., Tieppo, C., Garcez, F.R., 2008. Bioactive pentacyclic triterpenes from the stems of Combretum laxum. Molecules 13, 2717-2728.
Botta, B., Delle Monache, G., Delle Monache, F., Bettolo, M.G.B., Msonthi, J.D., 1985. Prenylated bianthrones and vismione F from Psorospermum febrifugum. Phytochemistry 24(4), 827-830.
Buchalter, L., 1969. Isolation and identification of emodin (1,3,8-tri-hydroxy-6-methylanthraquinone) from Rumex hymenosepalus, Family Polygonaceae. J. Pharm. Sci. 58(7), 904.
Davis, A.L., Cai, Y., Davies, A.P., Lewis, J.R., 1996. 1H and 13C assignments of some green tea polyphenols. Magn. Res. Chem. 34, 887-890.
Delle Monache, G., Botta, B., Oguakwa, J.U., Delle Monache, F., 1987a. New vismiones from Psorospermum tenuifolium. Bull. Chem. Soc. Ethiop. 1(1), 42-46.
Delle Monache, G., Delle Monache, F., Di Benedetto, R., Oguakwa, J.U., 1987b. New metabolites from Psorospermum tenuifolium. Phytochemistry 26, 2611-2613.
Epifano, F., Fiorito, S., Genovese, S., 2013. Phytochemistry and phramacognosy of the genus Psorospermum. Phytochem. Rev. 12, 673-684.
Facchetti, I., Grandi, M., Cucchi, P., Geroni, C., Penco, S., Vigevani, A., 1991. Influence of lipophilicity on cytotoxicity of anthracyclines in LoVo and LoVo/Dx human cell lines. Anticancer Drug Des. 6, 385-397.
Ge, L., Zhang, W., Zhou, G., Ma, B., Mo, Q., Chen, Y., Wang, Y., 2017. Nine phenylethanoid glycosides from Magnolia officinalis var. Biloba fruits and their protective effects against free radical-induced oxidative damage. Sci. Rep. 7, 45342; doi: 10.1038/srep45342.
Happi, G.M., Tiani, G.L.M., Gbetnkom, B.Y.M., Hussain, H., Green, I.R., Ngadjui, B.T., Kouam, S.F., 2020. Phytochemistry and pharmacology of Harungana madagascariensis: mini review. Phytochem. Lett. 35, 103-112.
Jain, P.S., Bari, S.B., 2010. Isolation of lupeol, stigmasterol and campesterol from petroleum ether extract of woody stem of Wrigtia tinctoria. Asian J. Plant Sci. 9(3), 163-167.
Jansen, O., Angenot, L., Tits, M., Nicolas, J.P., De Mol, P., Nikiema, J.B., Frederich, M., 2010. Evaluation of 13 selected medicinal plants from Burkina Faso for their antiplasmodial properties. J. Ethnopharmacol. 130, 143-15.
Kerharo, J., Adam, J.G., 1964. Les plantes medicinales, toxiques et magiques des Niominka et des Socé des iles du Saloum (Senegal). Acta Trop. Suppl. 8, 279-334.
Leet, J.E., Liu, X., Drexter, D.M., Cantone, J.L., Huang, S., Mamber, S.W., Fairchild, C.R., Hussain, R., Newman, D.J., Kingston, D.G.I., 2008. Cytotoxic xanthones from Psorospermum molluscum from the Madagascar rain forest. J. Nat. Prod. 71, 460-463.
Lenta, B.N., Devkota, K.P., Ngouela, S., Boyom, F.F., Naz, Q., Choudhary, M.I., Tsamo, E., Rosenthal, P.J., Sewald, N., 2008. Anti-plasmodial and cholinesterase inhibiting activities of some constituents of Psorospermum glaberrimum. Chem. Pharm. Bull. 56, 222-226.
Li, Y., Jiang, J-G., 2018. Health functions and structure-activity relationships of natural anthraquinones from plants. Food Funct. 9, 6063-6080.
Milne-Redhead, E., 1953. Flora of Tropical East Africa. London (UK): Royal Botanic Gardens, pp. 3-7.
Milne-Redhead, E., 1954. Hypericaceae, Flora of West Tropical Africa, 1:1. London (UK): Royal Botanic Gardens, pp 47-52.
Mouffok, S., Haba, H., Lavaud, C., Long, C., Benkhaled, M., 2012. Chemical constituents of Centaurea omphalotricha Coss. & Durieu ex Batt. & Trab. Rec. Nat. Prod. 6(3), 292-295.
Pouli, N., Marakos, P., 2009. Fused xanthone derivatives as antiproliferative agents. Anticancer Agents Med. 9, 77-98.
Poumale, P.H.M., Krebs, H.C., Amadou, D., Shiono, Y., Guedem, A.N., Komguem, J., Ngadjui, B.T., Randrianasolo, R., 2011. Flavonol glycoside from Psorospermum androsaemifolium. Chin. J. Chem. 29, 85-88.
Robson, N.K.B., 1961. Guttiferae Flora of Zimbabwe 1, p. 378.
Sahin, F.P., Ezer, N., Calis, I., 2006. Terpenic and phenolic compounds from Sideritis stricta. Turk. J. Chem. 30, 495-504.
Ssegawa, P., Kasenene, J.M., 2007. Medicinal plant diversity and uses in Sango bay area, southern Uganda. J. Ethnopharmacol. 113, 521-540.
Tabuti, J.R.S., Lye, K.A., Dhillion, S.S., 2003. Traditional herbal drugs of Bulamogi, Uganda: plants, use and administration. J. Ethnopharmacol. 88, 19-44.
Tchakam, P.D., Lunga, P.K., Kowa, T.K., Lonfouo, A.H., Wabo, H.K., Tapondjou, L.A., Tane, P., Kuiate, J.R., 2012. Antimicrobial and antioxidant activities of the extracts and compounds from the leaves of Psorospermum aurantiacum Engl. and Hypericum lanceolatum Lam. BMC Complement. Alternat. Med. 12, 136. doi: 10.1186/1472-668-12-136.
Tiani, G.L.M., Ahmed, I., Krohn, K., Green, I.R., Nkengfack, A.E., 2013. Kenganthranol F, a new anthranol from Psorospermum aurantiacum. Nat. Prod. Comm. 8(1), 103-104.
Xue, Z., Yan, R., Yang, B., 2016. Phenylethanoid glycosides and phenolic glycosides from stem bark of Magnolia officinalis. Phytochemistry 127, 50-62.
Zubair, M.F., Oladosu, I.A., Olawore, N.O., Usman, L.A., Fakunle, C.O., Hamid, A.A., Ali, M.S., 2011. Bioactive steroid from the root bark of Psorospermum corymbiferum. Chin. J. Nat. Med. 9, 264-266.