Isolation, characterization and biological activities of phytoconstituents from Lonchocarpus eriocalyx Harms leaves

Trends in Phytochemical Research

مقاله 3، دوره 2، شماره 3، آذر 2018، صفحه 135-146   

نوع مقاله: Original Article

نویسندگان

Lawrence Onyango Arot Manguro^{* 1}؛ Phillip Okind Owuor¹؛ Angeline Atieno Ochung²

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

²Department of Biological and Physical Sciences, Jaramogi Oginga Odinga University of Science and Technology, P.O Box 210-41061, Bondo, Kenya

چکیده

The plant species Lonchocarpus eriocalyx Harms (Fabaceae) is a deciduous slender tree or shrub which grows up to 15 m tall. It is an important medicinal plant in Kenya used to treat a wide range of ailments including eye infection, wound and ulcer. However, little is known about its chemical constituents. The present study aims to isolate secondary metabolites from the plant leaves along with their various biological activities. Eight compounds, namely friedelin (1), lupenone (2), lupeol (3), stigmasterol (4), chrysin (5), stigmasterol 3-O-β-glucoside (6), apigenin (7) and 3,5,7,2’,4’-pentahydroxyflavonol (8) were isolated from the CH₂Cl₂ and MeOH extracts of Lonchocarpus eriocalyx Harms leaves. Their structures were determined by using physical and spectroscopic methods as well as comparison with literature data. The CH₂Cl₂ and MeOH extracts together with the isolated compounds were subjected to an array of biological tests including antiplasmodial, larvicidal and mosquitocidal, antimicrobial and anti-inflammatory assays. The compounds 1-4 and 6 together with their anti-inflammatory activities are reported from this plant for the first time.

کلیدواژه‌ها

Biological activities؛ Fabaceae؛ Phytoconstituents؛ Lonchocarpus eriocalyx Harms

مراجع

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.

Adem, F.A., Kuete, V., Mbaveng, A.T., Heydenreich, M., Koch, A., Ndakala, A., Irungu, B., Yenesew, A., Efferth, T., 2018. Cytotoxic flavonoids from two Lonchocarpus species. Nat. Prod. Res. 1-9.

Adeyemi, O.O., Okpo, S.O., Okpaka, O., 2004. The analgesic effect of the methanol extract of Acanthus motanus. J. Ethnopharmacol. 90(1), 45-48.

Ahmad, R., Alfian, N., Soekamto, N.H., Harlim.T, Altenaand, I., 2012. A stigmasterol glycoside from the root wood of Melochia umbellta (Houtt) Stapf var degrabrata K. Indonesia J. Chem. 12(1), 100-103.

Alam, M.S., Chopra, N., Mohammed, A., Niwa, M., 1996. Oleanane and stigmasterol derivatives from Ambroma augusta. Phytochemistry 41(4), 1197-1200.

Attarde, D.J., Chaudhari, P.B., Pal, S., 2010. Estimation of sterols content in edible oil and ghee samples. Int. J. Pharm. Sci. Rev. 5(1), 135-137.

Batterman, T.J., Highet, R.J., 1964. Nuclear magnetic resonance spectra of flavonoids. Aust. J. Chem. 17(4), 428-439.

Bentjee, H., 1994. Kenyan Trees, Shrubs and Lianas, 3^rd Ed. National Museums of Kenya, Nairobi, Kenya.

Ceres, M., Gottlieb, R., Giovanno, B., Marini, B., France, D., Roger, P., 1981. Seven flavonoids from some Irarian angiosperms. Biochem. Syst. Ecol. 9(2-3), 129-147.

Chulay, J.D., Haynes, J.D., Diggs, C.L., 1983. Plasmodium falciparum: assessment of in vitro growth by 3H]hypoxanthine incorporation. Exp. Parasitol. 55(1), 138-146.

Coates, A., Hu, Y., Bax, R., Page, C., 2002. The future challenges facing the development of new antimicrobial drugs. Nat. Rev. Drug. Discov. 1(11), 895-910.

 Desjardins, R.E., Canfield, C.J., Haynes, J.D., Chulay, J.D., 1979. Quantitative assessment of antimalarial activity in vitro by a semi-automated microdilution technique. Antimicrob. Agents Chemother. 16(6), 710-718.

Duraipandiyan, V., Al-Dhabi, N.A., Irudayaraj,S.S., Sunil, C., 2016. Hypolipidemic activity of friedelin isolated from Azima tetracantha in hyperlipidemic rats. Rev. Bras. Farmacogn. 26(1), 89-93.

Eddy, N.B., Leimbach, D., 1953. Synthetic analgesics II. Dithienylbutenyl- and dithienyl butylamine. J. Pharmacol. Expl. Therapeutics 107(3), 385-393.

Gbolade, A.A., Lukwa, N., Kalenda, D., 2002. Guidelines for the Studies on Plant-Based Vector Control Agents, Obofemi Awolo University, Ile-Ile, Nigeria.

Haque, M., Begum, M.M., Hasan, M., Rahman, A.T., Hussain, M.I., Rahman, M.M., Ali, M.H., Islam, M.A., Sultan, M.Z., Reyad-ul-Ferdous, M., Hasan, C.M., 2015. Investigation of the medicinal potentials of Syzygium jambos (L.) extraction and characterization of the isolated compounds. Am. J. Biol. Sci.3(1-2), 12-18.

Hussain, J., Ali, L., Khan, A.L., Rehman, N.U., Jabeen, F., Kim, J., Al-Harrasi, A., 2014. Isolation and bioactivites of flavonoids morin and morin 3-O-β-D-glucoside from Acridocarpus orientalis- a wild Arabian medicinal plant. Molecules 19, 17763-17772.

Jong, H.K., Parry, C.M., Poll, T., Wiersinga, W.J., 2012. Host-pathogen interaction in invasive salmonellosis. PLoS Pathog. doi.org/10.1371/journal.ppat.1002933.

Kareru, P.G., Gachanja, A.N., Keriko, J.M., Kenji, G.M., 2007. Antimicrobial activity of some medicinal plants used by herbalists in Eastern province, Kenya. Afr. J. Tradit. Complement. Altern. Med.5(1), 51-55.

Kokwaro, J.O., 2009. Medicinal Plants of East Africa, 3^rd Ed., University of Nairobi Press, Nairobi, Kenya.

Koster, R, Anderso, M., De, B.E.J., 1959. Acetic Acid for Analgesic Screening. Federation Proceedings 18, 412.

Mabry, T., Markham, K.R., Thomas, M.B., 1970. The Systematic Identification of Flavonoids, 4^th Ed., Springer-Verlag, New York, USA.

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

Malca-Garcia, G.R., Hennig, L., Sieler, J., Bussmann, R.W., 2015. Constituents of Corynaea crassa “Pruvian Viagra”. Rev. Bras. Farmacogn. 25, 92-97.

Miyaichi, H.Y., Hanamitsue, E., Kizu, H., Tomimori, T. 2006. Studies on the constituents of Scutellaria species (XXII).1). Constituents of the roots of Scutellaria amabilis. Chem. Pharm. Bull. 54(4), 435-441.

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(1), 7-12.

 Opiyo, S.O., Ogur, J.A., Manguro, L.O.A., Lutz F. Itietze, L.F., Heiko Schuster, H., 2009. A new sterol diglycoside from Conyza floribunda. South African J. Chem. 62(4), 9-13.

Pavia, D.L., Lampman, G.M., Kris, G.S., 2009. Introduction to Spectroscopy: A Guide for Students of Organic Chemistry, 3^rd Ed., Belmont Brooks/Cole, CA, USA

Reginatto, H.F., Gosmann, G., Guillaume, D., Kauffmann, C., Schenkel, P.E., Schripsema, J., 2001. Steroidal and triterpenoidal glucosides from Passiflora alata. J. Brazillian Chem. Soc. 12(1), 32-36.

Singh, R.P., Pal, A., Pal, K. 2016. Antimicrobial activity of Phyllanthus niruri against different human pathogenic bacteria strains. World J. Pharmaceut. Res. 5(3), 1093-1098.

Trager, W., Jensen, J.B., 1976. Human malaria parasites in continuous culture. Sci. 193, 673-675.

Tuwei, J., 2006. Larvicidal and Antiplasmodial Compounds from Derris trifoliata, Lonchocarpus eriocalyx and Erythrina sacleuxii. MSc. Thesis, University of Nairobi, Nairobi, Kenya.

Yenesew, A., Derese, S., Midiwo, J.O., Irungu, B., Waters, N.C., Liyala, P., Akala, H., Heydenreich, M., Peter, M.G., 2003. Flavonoids and isoflavonoids with antiplasmodial activities from the root bark of Erythrina abyssinica. Planta Med. 69(7), 658-661.