Phytoconstituents with contact toxicity and antifeedant activities from Englerodaphne subcordata (Meisn) Engl. (Thymelaeaceae) crude leaf extracts
الموضوعات :
Albert Makenzi
1
,
Lawrence Manguro
2
,
Phillip Owuor
3
1 - Department of Chemistry, Maseno University, P.O. Box 333-40105 Maseno, Kenya
2 - Department of Chemistry, Maseno University, P.O. Box 333-40105 Maseno, Kenya
3 - Department of Chemistry, Maseno University, P.O. Box 333-40105 Maseno, Kenya
الکلمات المفتاحية: <i>Englerodaphne subcordata</i> (Meisn) Engl, contact toxicity, identification, phytoconstituents, Leaves, isolation, Antifeedant activity,
ملخص المقالة :
Englerodaphne subcordata (Meisn) Engl. (Thymelaeaceae) is a shrub that grows in dry evergreen forests, acacia woodlands and wooded grasslands. Phytochemical evaluation of the ethyl acetate and methanol crude leaf extracts of the plant led to the isolation of seven known compounds; β-amyrin acetate (1), 3-hydroxy-11-oxoolean-12-ene (2), dihydronitidine (3), dihydrochelerythrine (4), nagilactone (5), quercetin (6) and kaempferol-3-O-β-galactoside (7). The compounds showed moderate contact toxicity and antifeedant activities against Sitophilus zeamais and Prostephanus truncatus, insect pests of stored maize.
Abbot, W. S., 1925. A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 18, 265-267.
Adeyemi, M.M., Adebote, D.A., Amupitan, J.O., Oyewale, A.O., Agbaji, A.S., 2010. Antifeedant activity of quercetin isolated from the stem bark of Bobgunnia Madagascarensis (Desv.) J.H., Kirkbr and Wiersema (Caesalpiniaceae). Aust. J. Basic Appl. Sci. 4, 3342-3346.
Ali, A., Hussain, J., Al-Rawali, A., Al-Harrassi, A., 2014. Two new and four known triterpenes fom Boswellia sacra Fluckiger. Rec. Nat. Prod. 8, 407-411.
Ahsan, M., Haque, M.R., Hossain, M.D.B., Islam, S.N., Gray, A.I., Hassan, C.M., 2014. Cytotoxic dimeric quinolone-terpene alkaloids from the root bark of Zanthoxylum rhetsa. Phytochemistry 103, 8-12.
Aisya, L.S., Yun, Y.F., Herlina, T., Julachha, E., Zainuddin, A., Nurfarida, I., Hidayat, A.C., Supratman, V., Shiono, Y., 2017. Flavonoid compounds from the leaves of Kalonchoe prolifera and their cytotoxic activity against P-388 murine leukemia cells. Nat. Prod. Sci. 23, 139-145.
Arivoli, S., Tennyson, S., 2013. Antifeedant activity, developmental indices and morphogenetic variations of plant extracts against Spodoptera litura (Fab) (Lepidoptera: Noctuidae). J. Entomol. Zool. Studies 1, 87-96.
Beaumont, J.A., Edwards, T.J., Manning, J., Maurin, O., Rautenbach, M., Motsi, M.C., Fay, F. M., Chase, M.W., Van der Bank, M., 2009. Gnidia (Thymelaeaceae) is not monophyletic: Taxonomic implications for Thymelaeoideae and a partial new generic taxonomy for Gnidia. Botan J. Lin. Soc. 160, 412-417.
Berhanu, A., Asfaw, Z., Kelbessa, E., 2006. Ethnobotany of plants used as insecticides, repellents and antimalarial agents in Jabitehnan district, West Gojjam. Ethiop. J. Sci. 29, 87-92.
Borris, R., Blasko, G., Cordell, G., 1988. Ethnopharmacologic and phytochemical studies of Thymelaeaceae. J. Ethnopharmacol. 24, 41-91.
Brinks, M., 2009. Gnidia subcordata Meisn, In: Brinks M & Achigan-Dako E G Prota 16: Fibres/Plantes à fibres [CD-Rom], PROTA, Wageningen, Netherlands.
Davila, M., Sterner, O., Hinojosa, N., 2014. Secondary metabolites from Podocarpus parlatorei Pilger. Bol. J. Chem. 31, 21-27.
Dubey, S.C., Suresh, M., Singh, B., 2007. Evaluation of Trichoderma species against Fusarium oxysporum sp. Ciceris for integrated management of chickpea wilt. Biol. Control 40 118-127.
Feleke, S., Brehane, A., 2005. Triterpene compounds from the latex of Ficus sur. Bull. Chem. Soc. Ethiop. 19, 307-310.
Feng, F., Ye, F.Z., Li, C.L., Liu, W.Y., Xie, N., 2012. New benzophenanthridine isoquinoline alkaloids from Macleaya cordata Chin. J. Nat. Med. 10, 378-382.
Finney, D.J., 1971. Statistical Method in Biological Assay Griffin. London, U.K.
He, W., Cik, M., Appendino, G., Puyvelde, L.V., Leysen, J.E., De Kimpe, N., 2002. Daphnane-type diterpene orthoesters and their biological activities. Rev. Med. Chem. 2, 185-200.
Huang, Z., Zhou, F.C., Xu, D., Afzal, M., Bashir, M.H., Ali, S., Freed, S., 2008. Antifeedant activities of secondary metabolites from Ajuga nipponensis against Plutella xylostella Pak. J. Bot. 40, 1983-1992.
Isman, M.B., 2006. Botanical insecticides, deterrents and repellents in modern agriculture and an increasingly regulated world. Annu. Rev. Entomol. 51, 45-66.
Iwasaki, H., Oku, H., Takara, R., Miyahira, H., Hanashiro, K., Yoshida, Y., Kamada, Y., Toyokawa, T., Takara, K., Inafuku, M., 2006. The tumor specific cytotoxicity of dihydronitidine from Toddalia asiatica. Cancer Chemother. Pharmacol. 58, 451-459.
Kim, M., Lee, S., Lee, H., 2000. Growth inhibition effects of Brazilian and oriental medicinal plants on human intestinal bacteria. Agric. Chem. Biotechnol. 43(1), 54-58.
Kosini, D., Nukenine, E.N., 2017. Bioactivity of novel botanical insecticide from Gnidia kaussiana against Callosobruchus maculatus (Coleoptera chrysomelidae) in stored Vigna subterranea (Fabaceae) grains. J. Insect Sci. 31, 1-7.
Kumar, K., Mishra, A.K., Dubey, N.K., Tripathi, Y.B., 2007. Evaluation of Chenopodium ambrosioides oil as a potential source of antifungal, antiaflatoxigenic and antioxidant activity. Int. J. Food Microbiol. 115, 159-164.
Kuo, R., Chen, C., Lin, A., Yang-Chang, W., Fang-Rong, C., 2014. A new phenanthrene alkaloid, romucosine, from Rollinia mucosa Bail. Chem. Inform. 35, 1-12.
Kupchan, S.M., Baxter, Y.S.R.L., Hynes, H.R., 1977. Gnididione, new furano sesquiterpene from Gnidia latifolia. J. Org. Chem. 42, 348-350.
Kupchan, S.M., Shizuri, Y., Murae, T., Sweeny, J.G., Haynes, H.R., Shen, M., Barrick, J.C., Bryan, R.F., 1976. Gnidimacrin and gnidimacrin 20-palmitate, novel macrocyclic antileukemic diterpenoid esters from Gnidia subcordata. J. Am. Chem. Soc. 98, 5719-5720.
Ladan, Z., Amupitan, J.O., Oyewale, O.A., Okonkwo, E.M., Bamaiyi, L., Habila, N., Magaji, B., Ladan, E.O., 2013. Insecticidal activity of the leaf extract of Hyptis spicigera against Callosobruchus maculates on grains harvested in Zaria, Northern Nigeria. Int. J. Curr. Res. 5, 452-455.
da Liu, C., Chen, J., Wang, J.H., 2009. A novel kaempferol triglycoside from flower buds of Panax quinquefolium Chem. Nat. Compd. 45, 808-810.
Mabry, T.J., Markham, K.R., Thomas, M.B., 1970. The Systematic Identification of Flavonoids. Springer, Berlin, pp. 150-152.
Mallavadhani, U.V., Mahapatra, A., Raja, S., Manjula, C., 2003. Antifeedant activity of some pentacyclic triterpene acids and their fatty acid ester analogues. J. Agric. Food Chem. 51, 1952-1955.
Manguro, L.O.A., Kraus, W., Midiwo, J.O., 1996. A flavonol glycoside from Myrsine africana leaves. Phytochemistry 43, 1107-110.
Moussavi, N., Malterud, K.E., Mikolo, B., Dawes, D., Chandre, F., Corbel, V., Massamba, D., Overgaard, H.J., Wangensteen, H., 2015. Identification of chemical constituents of Zanthoxylum heitzii stem bark and their insecticidal activity against the malaria mosquito Anopheles gambiae. Parasit Vectors 8, 503-505.
Munkombwe, N.M., Galebotswe, P., Modibesane, K., Morebodi, N., 2003. Phenylpropanoid glycosides of Gnidia polycephala. Phytochemistry 64, 1401-1404.
Nyahanga, T., Jondiko, J.I., Manguro, L.O.A., Orwa, J.A., 2013. Antiplasmodial and larvicidal compounds of Toddalia asiatica root bark. J. Chem. Sci. 125, 1115-1121.
Obeng-Ofori, D., Reichmuth, C., 1997. Bioactivity of eugenol, a major component of essential oil of Ocimum suave (Wild.) against four species of stored-product Coleoptera. Int. J. Pest. Manag. 43, 89-94.
Oechslin, S.M., Konig, M., Oechslin-Merkeal., K., Wright, D., Kinghorn, A.D., Sticher, O., 1991. An NMR study of four benzophenanthridine alkaloids. J. Nat. Prod. 54, 519-524.
Ohmura, W., Doi, S., Aoyama, M., Ohara, S., 2000. Antifeedant activity of flavonoids and related compounds against the subterranean termite, Coptotermes formosanus Shiraki. J. Food Sci. 46, 149-153.
Okoye, N.N., Ajaghaku, D.L., Okeke, H.N., Ilodigwe, E.E., Nworu, S.C., Okoye, C.F.B., 2014. Beta-amyrin and alpha-amyrin acetate isolated from the stem bark of Alstonia boonei display profound anti-inflammatory activity. Pharm. Biol. 52, 1478-1486.
Olaniyan, O.D., van der Bank, M., Boatwright, J.S., Magee, A.R., Manning, J.C. 2020. A taxonomic revision of Englerodaphne Gilg (Thymelaeaceae: Thymelaeoideae). S. Afr. J. Bot. 130, 348-355.
Omar, S.M., Ahmat, N., Fatini, N., Azmin, N., 2015. Three flavonol glycosides from Calliandra surinamensis Benth. Malaysian. J. Anal. Sci. 20, 1530-1534.
Rosenthal, G.A., 1986. The chemical defences of higher plants. Sci. Am. 254, 94-99.
Sannabommaji, T., Kumar, V., Poornima, D.V., Gajula, H., Rajashekar, J., Manjunatha, T., Basappa, G., 201 Phytochemical Analysis With Special Reference to Leaf Saponins in Gnidia glauca (Fresen.), in N. Kumar (Ed.). Biotechnological Approaches for Medicinal and Aromatic Plants, pp 281-286, Gilg, Springer Nature, Singapore.
Sathyadevi, M., Subramanian, S., 2015. Extraction, isolation and characterization of flavonoids from the fruits of Physalis peruviana (Linn) extract. Asian J. Pharm. Clin. Res. 8, 152-157.
Souza, P.A., Marques, M.R., Mahmoud, P., Bolzani, V.S., Caputo, P.A., Canhete, G.M., Lette, B., Delima, D.P., 2010. Insecticidal effect of extracts from native plants to Mato Grosso do Sul Brazil on Sitophilus zeamais mots. (Coleopteran Curculionidae). Soc. Ent. Bras. 5, 1-5.
Sukumar, M., Rizo, J., Wall, M., Dreyfus, L.A., Kupersztoch, Y.M., Gierasch, L.M., 1995. The structure of Escherichia coli heat-stable enterotoxin by nuclear magnetic resonance and circular dichroism. Protein Sci. 4, 1718-1729.
Weinzierl, R.A., 2000. Botanical insecticides, soaps, and oils,’ In: Rechcigl, J. E., Rechcigl, N.A., (Eds) Biological and Biotechnological Control of Insect Pests. Lewis Publisher, New York.
Win, M.T., Pio, A.J., Flor, A.C., 2013. Insecticidal activity of crude plant extracts against Sitophilus zeamais spp. (Coleoptera: Curculionidae) and Callosobruchus chinensis (l.) (Coleoptera: Bruchidae) Philipp. Agric. Sci. 96, 154-162.
Zhang, W., Wang, Y., Geng, Z., Guo, S., Cao, J., Zhang, Z., Pang, X., Chen, Z., Du, S., Deng, Z., 2018. Antifeedant activities of lignans from stem bark of Zanthoxylum erratum DC against Tribolium castaneum. Molecules 617, 1-10.
Zhang, Y., Wang, D., Yang, L., Zhou, D., Zhang, J., 2014. Purification and characterization of flavonoids from the leaves of Zanthoxylum bungeanum and correlation between their structure and antioxidant activity. PLoS ONE 9, 1-3.
