[en] ETHNOPHARMACOLOGICAL RELEVANCE: Heinsia crinita is used in traditional medicine for the treatment of febrile illness and erectile dysfunction. Its stem bark powder is found in some peripheral markets in the Democratic Republic of the Congo (DRC) as a remedy against malaria. Investigations were conducted on crude extracts of leaves, fruits and stem barks in view to validate their use and to determine which plant part possesses the best antiplasmodial properties. MATERIALS AND METHODS: Different plant parts were extracted with methanol, ethanol and dichloromethane. Based on the preliminary assays, the dichloromethane extract of the stem bark was subjected to fractionation using preparative HPLC system and column chromatography. This step led to the isolation of two new iridoids which had their structures elucidated by NMR, UV, MS and FT-IR spectroscopic techniques. Extracts and pure compounds were tested in vitro against the 3D7 strain of Plasmodium falciparum. The inhibition of the parasite growth was evaluated in vitro by colorimetric method (p-LDH assay) and their cytotoxicity evaluated in vitro against the human non-cancer fibroblast cell line (WI38) through WST1 assay. The in vivo antiplasmodial activity was assessed by the inhibition of Plasmodium berghei growth in infected mice treated with the ethanol extract of H. crinita stem bark at the concentrations of 200 and 300mg/Kg/day per os, using a protocol based on the 4-d suppressive test of Peters and compared to a non-treated negative control group of mice (growth =100%). Finally the antioxidant activity of the same extract was evaluated using ABTS, DPPH and cell-based assays. RESULTS: A moderate in vitro antiplasmodial activity was observed for the dichloromethane extract of the stem bark of H. crinita (IC50 =29.2+/-1.39microg/mL) and for the two new iridoids, lamalbide 6, 7, 8- triacetate (IC50 =16.39+/-0.43microg/mL) as well as for its aglycone lamiridosin 6, 7, 8-triacetate (IC50 =0.44.56+/-1.12microg/mL). The ethanolic stem bark extract (200 and 300mg/kg/day, oral route) showed a moderate in vivo antimalarial activity in Plasmodium berghei-infected mice with 27.84+/-2.75% and 48.54+/-3.76% of inhibition of the parasite growth, respectively (p<0.01).). This extract displayed high cellular antioxidant activity using dichlorofluorescein-diacetate (DCFDA) on HL-60 monocytes. These crude extracts and pure compounds tested at the higher concentration of 100microg/mL did not show any cytotoxicity against WI38 cells. CONCLUSIONS: The results showed that H. crinita extracts possess antimalarial activity and contain some unusual iridoids with moderate antiplasmodial activity, therefore justifying to some extent its traditional use by the local population in DRC for this purpose. This is the first report of the isolation and antiplasmodial activity of these two new iridoids.
Abo, K.A., Lawal, I.O., Ogunkanmi, A., Evaluation of extracts of Triclisia suboardata oliv and Heinsia crinita (Afz) G. Taylor for antimicrobial activity against some clinical bacterial isolates and fungi. Afr. J. Pharm. Pharmacol. 5 (2011), 125–131.
Andrew, Ukeme Essien, Okokon, J.E., Idiong, O.J., Anti-inflammatory and Analgesic activities of Heinsia crinita. J. Mol. Clin. Pharmacol. 3 (2012), 30–39.
Brieskorn, C.H., Ahlborn, R., Lamalbid, ein neues iridoids aus flores lamii albi. Tetrahedron Lett. 2 (1973), 4037–4038.
Eigtved, P., Jensen, S.R., Nielsen, B.J., A novel Iridoid glucoside isolated from Lamium album L. Acta Chem. Scand. 28 (1974), 85–91.
Eseyin, O., Etiemmana, G., Enobong, M., Ebong, A., Etim, I., Udobre, S., Johnson, E., Attih, E., Effiong, A., Evaluation of the Antioxidant Properties of Some Commonly Eaten Vegetables in Akwa Ibom State of Nigeria. Annu. Res. Rev. Biol. 5 (2015), 165–173, 10.9734/ARRB/2015/13439.
Fidock, D.A., Rosenthal, P.J., Croft, S.L., Brun, R., Nwaka, S., Einstein, A., Antimalarial drug discovery: efficacy models for compound screening. Nat. Rev. Disco. 3 (2004), 509–520, 10.1038/nrd1416.
Floegel, A., Kim, D., Chung, S., Koo, S.I., Chun, O.K., Comparison of ABTS/DPPH assays to measure antioxidant capacity in popular antioxidant-rich US foods. J. Food Compos. Anal. 24 (2011), 1043–1048, 10.1016/j.jfca.2011.01.008.
Franck, T., Mouithys-Mickalad, A., Robert, T., Ghitti, G., Deby-Dupont, G., Neven, P., Serteyn, D., Chemico-biological interactions differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: A structure/redox potential relationship study. Chem. Biol. Interact. 206 (2013), 194–203, 10.1016/j.cbi.2013.09.009.
Frederich, M., Tits, M., Goffin, E., Philippe, G., Grellier, P., De Mol, P., Hayette, M.-P., Angenot, L., In vitro and in vivo antimalarial properties of isostrychnopentamine, an indolomonoterpenic alkaloid from Strychnos usambarensis. Planta Med. 70 (2004), 520–525, 10.1055/s-2004-827151.
Frédérich, M., Jacquier, M.J., Thépenier, P., De Mol, P., Tits, M., Philippe, G., Delaude, C., Angenot, L., Zèches-Hanrot, M., Antiplasmodial activity of alkaloids from various Strychnos species. J. Nat. Prod. 65 (2002), 1381–1386, 10.1021/np020070e.
Girard-Lalancette, K., Pichette, A., Legault, J., Sensitive cell-based assay using DCFH oxidation for the determination of pro- and antioxidant properties of compounds and mixtures: analysis of fruit and vegetable juices. Food Chem. 115 (2009), 720–726, 10.1016/j.foodchem.2008.12.002.
Jansen, O., Angenot, L., Tits, M., Nicolas, J.P., De Mol, P., Nikiéma, J.B., Frédérich, M., Evaluation of 13 selected medicinal plants from Burkina Faso for their antiplasmodial properties. J. Ethnopharmacol. 130 (2010), 143–150, 10.1016/j.jep.2010.04.032.
Jonville, M.C., Kodja, H., Humeau, L., Fournel, J., De Mol, P., Cao, M., Angenot, L., Frédérich, M., Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity. J. Ethnopharmacol. 120 (2008), 382–386, 10.1016/j.jep.2008.09.005.
Odukoya, Inya-Agba, Segun, Sofidiya, Ilori, Antioxydant activity of selected Nigerian green Leafy vegetables. Am. J. Food Technol. 2 (2007), 169–175.
Okokon, J.E., Umoh, E.E., Etim, E.I., Jackson, C.L., Antiplasmodial and antidiabetic activities of ethanolic leaf extract of Heinsia crinata. J. Med. Food 12 (2009), 131–136, 10.1089/jmf.2008.0116.
Plouvier, V., Favre-Bonvin, J., Les iridoids et séco-iridoids: répartition, structure, propriété, biosynthèse. Phytochemistry 10 (1971), 1697–1722.
Souza, B.D., Souza, V.D., Swagata, H., Vijayalaxmi, K., Namratha, A.S., Erythrocyte antioxidant enzymes and their correlation with malon- dialdehyde in malaria. Biomed. Res. 20 (2009), 25–27.
Tsumbu, C.N., Deby-Dupont, G., Tits, M., Angenot, L., Franck, T., Serteyn, D., Mouithys-Mickalad, A., Antioxidant and antiradical activities of Manihot esculenta Crantz (Euphorbiaceae) leaves and other selected tropical green vegetables investigated on lipoperoxidation and phorbol-12-myristate-13-acetate (PMA) activated monocytes. Nutrients 3 (2011), 818–838, 10.3390/nu3090818.
Udousoro, I., Ekanem, P., Assessment of proximate compositions of Twelve edible vegetables in Nigeria. Int. J. Mod. Chem. 4 (2013), 79–89.
Uwakwe, A.A., Akaninwor, J., Effect of queous leaf extract of Heinsia crinita on haematological and some biochemical indices of toxicity in streptozotocin induced diabetic rats. Int. J. Sci. Res. Innov. Technol. 2 (2015), 116–126.
Zhang, H., Rothwangl, K., Mesecar, A.D., Sabahi, A., Rong, L., Fong, H.H.S., Lamiridosins, hepatitis C virus entry inhibitors from Lamium album. J. Nat. Prod. 72 (2009), 2158–2162.
