Analgesics from Lonchocarpus eriocalyx Harms

Ochung, Angeline A.; Owuor, Phillip O.; Manguro, Lawrence A.O.; Ismael, Ishola O.; Nyunja, Regina A.; Ochieng, Charles O.; Opiyo, Sylvia A.

Document Type : Original Article

Authors

¹ Department of Chemistry, Maseno University, P.O. Box 333-40105, Maseno, Kenya

² Department of Pharmacology, College of Medicine, University of Lagos, Nigeria

³ Department of Physical Sciences, Jaramogi Oginga Odinga University of Science and Technology, P.O. Box 210-41061, Bondo, Kenya

Abstract

Four lupane-type terpenoids, namely lupeol (1), friedelin (2), stigmasterol (3), and stigmasterol-3-O-glucoside (4) were isolated from the ethyl acetate extract of leaves of Lonchocarpus eriocalyx Harms. These compounds were obtained by extensive silica gel chromatography and their structures elucidated by 1D and 2D nuclear magnetic resonance (NMR) as well as comparison with literature data. The ethyl acetate, dichloromethane and methanol extracts (100 mg/Kg) had a pretreatment latency of 3.1±0.15, 3.0±0.01 and 3.5±0.12 at the zero minute. The post latency of 6.4±0.13 was observed for ethyl acetate at 30 minutes which confirmed its effectiveness to halt pain, while compounds 1 and 2 had pretreatment latency of 3.1±0.12 and 3.2±0.12, respectively. The isolated compounds from this medicinal plant along with their analgesic activity have been reported for the first time.

Graphical Abstract

Keywords

References

Abdullahi, S.M., Musa, A.M., Abdullahi, M.I., Sule, M.I., Sani, Y.M., 2013. Isolation of lupeol from the stem bark of Lonchocarpus sericeus (Papillonaceae). Scholars Acad. J. Biosci. 1(1), 18-19.

Adair, R.S.S., 2001. Biological activity of plant extracts: Novel analgesic drugs. Expert Opin. Emerg. Drugs6(2), 261-279.

Adeyemi, O.O., Okpo, S.O., Okpaka, O., 2004. The analgesic effect of the methanol extract of Acanthus motanus. J. Ethnopharmacol. 90, 45-48.

Alam, M.S., Chopra, N., Mohammed, A., Niwa, M., 1996. Oleanen and stigmasterol derivatives from Ambroma augusta. Phytochemistry 41, 1197-1200.

Alfian, N., Ahmad, R., Nunuk, H.S., Tjodi, H., Ian, V.A., 2012. A stigmasterol glycoside from the root wood of Melochia umbellata (Houtt) Stapf Var.Degrabrata K. Indones. J. Chem. 12(1), 100-103.

Cassidy, E., Caittnli, N., William, S., 2011. Lonchocarpus polyphenolics and their biological activities. Nat. Prod. J. 1(2), 75-104.

Ceres, M., Gottlieb, R., Giovanno, B., Marini, B., France, D., Roger, P., 1981. Seven flavonoids froms some Irarian angiosperms. Biochem. Syst. Ecol. 9(2), 129-147.

Correa, R.S., Colho, C.P., Santos, M.H., Ellena, J., Doriguetto, A.C., 2009. Lupeol. Acta Crystallogr. C, 65, 97-99.

Cragg, G., Newman, D.J., Snader, K.M., 1997. Natural products in drug discovery and development. J. Nat. Prod. 60(1), 52-60.

Daksha, A., Jaywant, P., Bhagyashree, C., Subodh, P., 2010. Estimation of sterols content in edible oil and ghee samples. Int. J. Pharm. Sci. Rev. Res. 5, 135-137.

Eddy, N.B., Leimbach, D., 1953. Synthetic analgesics II. Dithienylbutenyl- and dithienyl butylamine. J. Pharmacol. Exp. Ther. 107, 385-393.

Fotie, J., Bohle, D.S., Leimanis, M.L., Georges, E., Rukungu, C., Nkengfack, A.E., 2006. Lupeol, long-chain fatty esters with antimalarial activity from Holarrhena floribunda. J. Nat. Prod. 69, 62-67.

Frezza, C., Venditti, A., Serafini, I., Carassiti, A., Foddai, S., Bianco, A., Serafini, M., 2017. Phytochemical characteristics of Galeopsis ladanum subsp. angustifolia (Ehrh. ex Hoffm.) Gaudin collected in Abruzzo region (Central Italy) with chemotaxonomic and ethnopharmacological implications. Trends Phytochem. Res. 1, 61-68.

Grasiely, F.S., Lucienir, P.D., Antonio, F.C.A., Gracia, D.F., Sidney, A.V., Roqueline, R.S., Djalma, M.O., Jacqueline, A.T., 2012. New triterpenes from Maytenus robusta: Structural elucidation based on NMR experimental data and theoretical calculations. Molecules 17, 13439-13456.

Koster, R., Anderson, M., De, B.E.J., 1959. Acetic acid for analgesic screening. Federation Proceedings 18, 412.

Kulkarni, S.K., 2003. Handbook of Experimental Pharmacology. pp. 125-127.

Lutta, K.P., Bii, C., Akenga, A.T., Cornelius, W.W., 2008. Antimicrobial marine natural products from the sponge Axinella infundibuliformis. Rec. Nat. Prod.2, 116-127.

Mahbuba, K., Mirajum, B., Abdul, Q., 2012. Sterols and sterol glucoside from Phyllanthus species. Dhaka Univ. J. Sci. 60(1), 5-10.

Majidul, H.M., Marium, B., Moynul, H., Towheedur, R.M. Iftekhar, H., Mohammad, M.R., Hazrat, A., Ashraful, I. Zakir, S., Reyad, F., Choudhury, M.H., 2015. Investigation of the medicinal potentials of Syzygium jambos (L.) extract and characterization of the isolated compounds. Am. J. Biol. Sci. 3(2-1).

Mohammadhosseini, M., 2017. The ethnobotanical, phytochemical and pharmacological properties and medicinal applications of essential oils and extracts of different Ziziphora species. Ind. Crops Prod. 105, 164-192.

Mohammadhosseini, M., Sarker, S.D., Akbarzadeh, A., 2017. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J. Ethnopharmacol. 199, 257-315.

Mohammadhosseini, M., Venditti, A., Sarker, S.D., Nahar, L., Akbarzadeh, A., 2019. The genus Ferula: Ethnobotany, phytochemistry and bioactivities – A review. Ind. Crops Prod. 129, 350-394.

Omisore, N.O.A., Adewunmi, C.O., Iwalewa, E.O., Ngadjui, B.T., Watchueng, J., Abegaz, B.M., Ojewole, J.A.O., 2004. Antinociptive and anti-inflammatory effects of Dorstenia barteri (Moraceae) leaf and twig extracts in mice. J. Ethnopharmacol. 95, 7-12.

Orabi, Y.K, 2011. Search for new leads from marine macrofauna: collection from Kuwaiti Arabian gulf coast. Int. J. Pharm. Sci. 3(40), 228-232.

Pandey, R., Verma, R.K., Gupta, M.M., 2006. Pentadecanoic acid β-D-glucoside from Clerodendrum inerme. Indian J. Chem. 45(9), 2161-2163.

Reginatto, H.F., Gosmann, G., Guillaume, D., Kauffmann, C., Schenkel, P.E., Schripsema, J., 2001. Steroidal and triterpenoidal glucosides from Passiflora alata. J. Braz. Chem. Soc. 12, 32-36.

Shashank, M., Ajay, K.J., Manoj James, C.M., Debjit, B., 2013. Analgesic and anti inflammatory activity of Kalanchoe pinnata (Lam.) Pers. J. Med. Plants Stud. 1(2), 24-28.

Smet, P., 1997. The role of plant derived drugs and herbal medicines in healthcare. Drug54(6), 801-840.

Strohl, W., 2000. The role of natural products in a modern drug discovery program. Drug Discov. Today5(2), 39-41.

Thanakijcharoenpath, W., Theanphong, O., 2007. Triterpenoids from the stem of Diospyros glandulosa. Thai. J. Pharmacol. Sci. 31, 1-8.

Tuwei, J., 2006. Larvicidal and antiplasmodial compounds from Derris trifoliata, Lonchocarpus eriocalyx and Erythrina sacleuxii, M.Sc. Thesis, Department of Chemistry, University of Nairobi.

Venditti, A., Bianco, A., 2018. Secondary metabolites of Hypericum richeri Vill. collected in Central Italy: chemotaxonomy and ethnomedicinal relevance. Trends Phytochem. Res. 2, 155-162.

Venditti, A., Frezza, C., Serafini, I., Pulone, S., Scardelletti, G., Sciubba, F., Bianco, A., Serafini, M., 2018. Chemical profiling of the fruits of Styrax officinalis L. from Monti Lucretili (Latium region, Central Italy): Chemotaxonomy and nutraceutical potential. Trends Phytochem. Res. 2, 1-12.

Verpoorte, R., (1998). Exploration of nature´s chemodiversity: The role of secondary metabolites as leads in drug development. Drug Discov. Today3(5), 232-238.

Yenesew, A., Derese, S., Midiwo, J.O., Irungu, B., Waters, N.C., Liyala, P., Akala, H., Heydenreich, M., Peter, M.G., (2003a). Flavonoids and isoflavonoids with antiplasmodial activities from the root bark of Erythrina abyssinica. Planta Med. 69, 658-661.

Trends in Phytochemical Research

Analgesics from Lonchocarpus eriocalyx Harms

References

References

Volume 2, Issue 4 - Serial Number 4
Autumn 2018
Pages 253-260

Analgesics from Lonchocarpus eriocalyx Harms

References

References

Volume 2, Issue 4 - Serial Number 4Autumn 2018Pages 253-260

Volume 2, Issue 4 - Serial Number 4
Autumn 2018
Pages 253-260