Antiplasmodial and antileishmanial inhibitory activity of triterpenes and steroidal alkaloid from the leaves of Funtumia elastica (Preuss) Stapf (Apocynaceae)
[en] The phytochemical study of leaves of Funtumia elastica led to the isolation of three undescribed ursane derivatives, funtumic acids A, B and C (1–3), as well as one steroidal alkaloid, elasticine (4) and five other known compounds (5–9). Their structures were elucidated on the basis of NMR, MS, IR, UV spectroscopic data as well as by comparison with the literature. The compound 5-hydroxypyridine-3-carboxamide (9) was isolated for the first time from the Apocynaceae family. All the isolated compounds were evaluated for their antiparasitic effects against 3D7 and Dd2 strains of Plasmodium falciparum and promastigotes of Leishmania donovani (MHOM/SD/62/1S). Compounds 1–4 possessed good in vitro antimalarial activities against CQR Dd2 with IC50 values ranging from 4.68 to 5.36 μg/mL and moderate on CQS 3D7. Only compounds 1 and 2 showed leishmanicidal activities with IC50 values ranging between 10.49 and 13.21 μg/mL. In addition, crude extract exhibited potent antiplasmodial (IC50 0.91 and 3.12 μg/mL) and antileishmanial (IC50 3.32 μg/mL) activities, thus demonstrating their potential synergistic action.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Ma'mag, Larissa Kom
Zintchem, Auguste Abouem A.
Théodora, Kopa Kowa
Théodore, Atchadé Alex De
lauve, Tchokouaha Yamthe
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Bikobo, Dominique Serge Ngono
Pegnyemb, Dieudonné Emmanuel
Language :
English
Title :
Antiplasmodial and antileishmanial inhibitory activity of triterpenes and steroidal alkaloid from the leaves of Funtumia elastica (Preuss) Stapf (Apocynaceae)
de Mesquita, M.L., Desrivot, J., Bories, C., Fournet, A., de Paula, J.E., Grellier, P., Espindola, L.S., Antileishmanial and trypanocidal activity of Brazilian Cerrado plants. Mem. Inst. Oswaldo Cruz. Rio De Janerio 100 (2005), 783–787.
Snow, R.W., Guerra, C.A., Noor, A.M., Myint, H.Y., Hay, S.I., The global distribution of clinical episodes of Plasmodium falciparum malaria. Nature. 434 (2005), 214–217.
Haerdi, F., Native Medicinal Plants of Ulanga District of Tangayika (East Africa) Dissertation. 1964, Verlag Fur Recht Und Gesellschaft, AG Basel.
Odugbemi, T.O., Odunayo, R., Akinsulire, I.E., Medicinal plants useful for malarial therapy in Okeigbo. Afr. J. Trad. Compl. Alter. Med. 4 (2007), 191–198.
Truong-Ho, M., Khuong-Huu, Q., Goutarel, R., Alcaloïdes stéroïdiques XV. Les irehdiamines A et B, alcaloïdes du Funtumia elastica (Preuss) Stapf. Bull. Soc. Chim. France, 594, 1963.
Hanelt, P., Mansfeld's world database of agricultural and horticultural crops. Mansfeld's World Database of Agricultural and Horticultural Crops. Gatersleben, 2018, Leibniz Institute of Plant Genetics and Crop Plant Research (IPK), Germany, 185.
Zirihi, G.N., Grellier, P., Guédé-Guina, F., Bodo, B., Mambu, L., Isolation, characterization and antiplasmodial activity of steroidal alkaloids from Funtumia elastica (Preuss) Stapf. Bioorg. Med. Chem. Lett. 15 (2005), 2637–2640.
Adekunle, A.A., Ikumapayi, A.M., Antifungal property and phytochemical screening of the crude extracts of Funtumia elastica and Mallotus oppositifolius. West Indian. Med. J. 55 (2006), 219–223.
Bouquet, A., Fetish and traditional medicine of Congo (Brazzaville). O.R.S.T.O.M. Paris. 36 (1969), 177–178.
Betti, J.L., An ethnobotanical study of medicinal plants among the Baka pygmies in the Dja biosphere reserve, Cameroon. Afr. Stud. Monogr. 25 (2004), 1–27.
Mukherjee, E., Gantait, S., Kundu, S., Sarkar, S., Bhattacharyya, S., Biotechnological interventions on the genus Rauvolfia: recent trends and imminent prospects. Appl. Microbiol. Biotechnol., 103, 2019, 73257354.
Burkill, H.M., The useful plants of West Tropical Africa. Families A–D, 2nd ed, Vol. 1, 1985, Kew, Richmond, Royal Botanic Gardens.
Mukam, L.C.G., Hentchoya, J., Njimi, T., Ourisson, G., Le cyclofon- tumienol, methyl-4a sterol en C31 de Funtumia elastica. Tetrahedron Lett. 29 (1973), 2779–2782.
Wagner, H., Seegert, K., Ilyas, M., Odenthal, K.P., The steroid alkaloids of Funtumia africana. Plant. Med. 53 (1987), 444–449.
Maduabuchi, A.C., Emeka, E.O., Li, L., Ying, L., Fuhui, W., Inhibitory action of Funtumia elastica extracts on the corrosion of Q235 mild steel in hydrochloric acid medium: experimental and theoretical studies. J. Dispers. Sci. Technol. 36 (2015), 1115–1125.
Lambros, C., Vanderberg, J.P., Synchronization of Plasmodium falciparum erythrocytic stages in culture. J. Parasitol. 65 (1979), 418–420.
Smilkstein, M., Sriwilaijaroen, N., Kelly, J.X., Wilairat, P., Riscoe, M., Simple and inexpensive fluorescence-based technique for high-throughput antimalarial drug screening. Antimicrob. Agents Chemother. 48 (2004), 1803–1806.
Süzgeç-Selçuk, S., Meriçli, A.H., Güven, K.C., Kaiser, M., Casey, R., Hingley-Wilson, S., Lalvani, A., Tasdemir, D., Evaluation of Turkish seaweeds for antiprotozoal, antimycobacterial and cytotoxic activities. Phytother. Res. 25 (2011), 778–783.
Gołembiewska, E., Skalicka-Wozniak, K., Głowniak, K., Methods for the isolation and identification of triterpenes and sterols in medicinal plants. Curr. Issues. Pharm. Med. Sci. 26 (2013), 26–32.
Weber, B., Herrmann, M., Hartmann, B., Joppe, H., Schmidt, C.O., Bertram, H.J., HPLC/MS and HPLC/NMR as hyphenated techniques for accelerated characterization of the main constituents in Chamomile (Chamomilla recutita [L.] Rauschert). Eur. Food Res. Technol. 226 (2008), 755–760.
Askari, M., Sahebkar, A., Iranshahi, M., Synthesis and purification of 7-prenyloxycoumarins and herniarin as bioactive natural coumarins, Iran. J. Basic Med. Sci. 12 (2009), 63–69.
Mouffok, S., Haba, H., Lavaud, C., Benkhaled, M., Chemical constituents of Centaurea omphalotricha Coss. & Durieu ex Batt. & Trab. Rec. Nat. Prod. 6 (2012), 292–295.
Amir Reza, J., Omidreza, F., Ramin, M., Sajad, S., Somayeh, Z., Mehdi, Z., Mehdi, M., Masroorbabanari, J.N., Chandran, M., Bernd, S., Ian, T.B., Cytotoxic activity and chemical constituents of Anthemis mirheydari. Pharm. Biol. 54 (2016), 2044–2049.
Maduabuchi, A.C., Emeka, E.O., Li, L., Ying, L., Fuhui, W., Inhibitory action of Funtumia elastica extracts on the corrosion of Q235 mild steel in hydrochloric acid medium: experimental and theoretical studies. J. Dispers. Sci. Technol. 36 (2015), 1115–1125.
Ding, H.Y., Lin, H.C., Teng, C.M., Wu, Y.C., Phytochemical and pharmacological studies on Chinese Paeonia species. J. Chin. Chem. Soc. Taip. 47 (2000), 381–388.
Mahato, S.B., Kundu, A.P., 13C NMR spectra of pentacyclic triterpenoids a compilation and some salient features. Phytochemistry 37 (1994), 1517–1575.
Akbar, E., Malik, A., Antimicrobial triterpenes from Debregeasia salicifolia. Nat. Prod. Lett. 16 (2002), 339–344.
Kim, K.H., Choi, S.U., Lee, K.R., Cytotoxic triterpenoids from Berberis koreana. Planta Med. 78 (2012), 86–89.
Triana, J., López, M., Pérez, F.J., Platas, J.G., Estévez, F., León, J.F., Hernández, J.C., Brouard, I., Bermejo, J., Chemical constituents of Tolpis species. Fitoterapia 80 (2009), 437–441.
Bhutani, K.K., Vaid, R.M., Ali, M., Kapoor, R., Soodan, S.R., Kumar, D., Steroidal alkaloids from Holarrhena antidysenterica. Phytochemistry 29 (1990), 969–972.
Kumar, A., Ali, M., A new steroidal alkaloid from the seeds of Holarrhena antidysenterica. Fitoterapia 71 (2000), 101–104.
Cheenpracha, S., Jitonnom, J., Komek, M., Ritthiwigrom, T., Laphookhieo, S., Acetylcholinesterase inhibitory activity and molecular docking study of steroidal alkaloids from Holarrhena pubescens barks. Steroids 108 (2016), 92–98.
Atta-ur, R., Zaheer-ul, H., Feroz, F., Khalid, A., Nawaz, S.A., Khan, M.R., Choudhary, M.I., New cholinesterase-inhibiting steroidal alkaloids from Sarcococca saligna. Helv. Chim. Acta. 87 (2004), 439–448.
Moretti, C., Sauvain, M., Lavaud, C., Massiot, G., Bravo, J.A., Muñoz, V.A., Novel antiprotozoal aminosteroid from Saracha punctate. J. Nat. Prod. 61 (1998), 1390–1393.
Kupchan, S.M., Kennedy, R.M., R. chleigh, S.W., Ohta, G., Buxus alkaloids. XII. Benzamide alkaloids from Boxus sempervirens. Tetrahedron 23 (1967), 4563–4586.
Černý, V., Šorm, F., Chapter 8: steroid alkaloids: alkaloids of Apocynaceae and Buxaceae. The alkaloids: chemistry and physiology, 9, 1967, Academic Press, New York, 305–426.
Stolyarova, L.G., Akhundov, R.A., Rakhmankulova, I.K., Voronina, T.A., Smimov, L.D., Dyamaev, K.M., Synthesis and psychopharmacological and antihypoxic activity of some β-substituted pyridine carboxylic acids. Pharm. Chem. J. 20 (1986), 29–31.
Güvenalp, Z., Demirezer, O., Flavonol glycosides from Asperula arvensis L. Turk. J. Chem. 29 (2005), 163–169.
He, Z.D., Ma, C.Y., Zhang, H.J., Tan, G.T., Tamez, P., Sydara, K., Bouamanivong, S., Southavong, B., Soejarto, D.D., Pezzuto, J.M., Fong, H.H.S., Antimalarial constituents from Nauclea orientalis (L.) L. Chem. Biodivers. 2 (2005), 1378–1386.
Torres-Santos, E.C., Lopes, D., Oliveira, R.R., Carauta, J.P., Falcao, C.A., Kaplan, M.A., Rossi-Bergmann, B., Antileishmanial activity of isolated triterpenoids from Pourouma guianensis. Phytomedicine 11 (2004), 114–120.
Cunha, W.R., Martins, C., Ferreira, D.S., Crotti, A.E.M., Lopes, N.P., Albuquerque, S., In vitro trypanocidal activity of triterpenes from Miconia species. Planta Med. 69 (2003), 470–472.