Sesquiterpenoids with antiplasmodial activities from Warburgia stuhlmanii Engl. root bark
الموضوعات :
Albert Makenzi
1
(Department of Chemistry, Maseno University, P. O. Box 333-40105 Maseno, Kenya)
Lawrence Manguro
2
(Department of Chemistry, Maseno University, P. O. Box 333-40105 Maseno, Kenya)
Philip Owuor
3
(Department of Chemistry, Maseno University, P. O. Box 333-40105 Maseno, Kenya)
الکلمات المفتاحية: Root bark, phytoconstituents, Antiplasmodial activities, identification, <i>Warburgia stuhlmannii</i> Engl, isolation,
ملخص المقالة :
Phytochemical investigation of Warburgia stuhlmannii ethyl acetate root extract led to isolation of ten known compounds identified as polygodial (1), cinnamolide (2), warburganal (3), bemadienolide (4), ugandensidial (5), muzigadial (6), mukaadial (7), 6α-hydroxymuzigadial (8), ugandensolide (9) and deacetylugandensolide (10). Structures of the isolated compounds were determined by spectroscopic methods; NMR, IR, UV-Vis and spectrometric method, EI-MS, as well as comparison with literature data. In their antiplasmodial activities, the compounds had moderate activities against the chloroquin sensitive (D10) and chloroquin resistant (W2) strains of Plasmodium falciparum. Among the compounds, mukaadial (7) had the highest activities against both D10 and W2 strains of P. falciparum, with IC50 values of 5.2 µM and 5.8 µM, respectively, while muzigadial (6) though effective on D10 strain (IC50 = 5.6 µM) was less effective against W2 strain (IC50 = 16.4 µM).
Anonymous, Centres for Disease Control and Prevention (CDC), 2007. Malaria Facts. United States Department of Health and Human Sciences, USA.
Bailly, C., 2021a. Anticancer butanolides and lignans from the Makko tree, Machilus thunbergii Siebold & Zucc. (Lauraceae). A review. Trends Phytochem. Res. 5(3), 136-147.
Bailly, C., 2021b. Bioactive biflavonoids from Wikstroemia indica (L.) C.A. Mey. (Thymelaeaceae): A review. Trends Phytochem. Res. 5(4), 190-198.
Beentje, H., 1994. Kenya Trees and Lianas, National Museums of Kenya, Nairobi.
Bordignon A., Frédérich, M., Ledoux, A., Campos, P., Clerc, P., Hermann, T., Quetin-Leclercq, J., Cieckiewicz, E., 2017. In vitro antiplasmodial and cytotoxic activities of sesquiterpene lactones from Vernonia fimbrillifera Less. (Asteraceae). Nat. Prod. Res. 32, 1463-1466.
Canonica, I., Corbella, A., Gariboldi, P., Jommi, G., Krepinsk, J., 1969. Sesquiterpenoids of Cinnamosma fragrans baillon: Structure of bemarivolide, bemadienolide and fragrolide. Tetrahedron 25, 3903-3908.
Grace, M.H., Lategan, C., Mbeunkui, F., Graziose, R., Smith, P.J., Raskin, I., Lila, M.A., 2010. Antiplasmodial and cytotoxic activities of drimane sesquiterpenes from Canella winterana. Nat. Prod. Comm. 5, 1869-1872.
Kioy, D., Gray, A.I., Waterman, P.G., 1989. Further drimane sesquiterpenes from the stem bark of Canella winterana. J. Nat. Prod. 52, 174-177.
Kioy, D., Gray, J., Waterman, P.G., 1990. A comparative study of the stem bark drimane sesquiterpenes and leaf volatile oils of Warburgia ugandensis and Warburgia stuhlmannii. Phytochemistry 29, 3535-3538.
Kokwaro, J.O., 2009. Medicinal Plants of East Africa. East African Literature Bureau, Nairobi, Kenya.
Kubo, I., Mashumoto, T., Kakooto, A.B., Mubiru, N.K., 1983. Structure of mukaadial, a molluscicide from the Warburgia plant. Chem. Lett. 7, 979-980.
Lindsay, S., Ansell, J., Selmano, C., Cox, V., Hamitan, K., Walraven, G., 2000. Effects of pregnancy on exposure to malaria mosquitoes. The Lancet 355, 1972-1975.
Maroyi, A., 2014. The genus Warburgia: A review of its traditional uses and pharmacology. Pharm. Biol. 52(3), 378-391.
Mehrotra, E., Vishwakarma, J., Tripathi, A.C., Sonar, P.K., Saraf, S.K., 2019. Schizonticidal antimalarial sesquiterpene lactones from Magnolia champaca (L.) Baill. ex Pierre: Microwave-assisted extraction, HPTLC fingerprinting and computational studies. Nat. Prod. Res. 33(4) 568-572.
Mohammadhosseini, M., Frezza, C., Venditti, A., Akbarzadeh, A., 2019. Ethnobotany and phytochemistry of the genus Eremostachys Bunge. Curr. Org. Chem. 23, 1828-1842.
Mohammadhosseini, M., Frezza, C., Venditti, A., Sarker, S., 2021. A systematic review on phytochemistry, ethnobotany and biological activities of the genus Bunium L. Chem. Biodivers. 18(11), e2100317.
Mohammadhosseini, M., Venditti, A., Akbarzadeh, A., 2019. The genus Perovskia Kar.: ethnobotany, chemotaxonomy and phytochemistry: a review. Toxin Rev. 40(4), 484-505.
Muchugi, A., Muluvi, G.M., Kindt, R., Kadu, C.A., Simons, A.J., Jamnadas, R.H., 2009. Genetic structuring of important medicinal species of genus Warburgia as revealed by AFLP analysis. Tree Genet. Genom. 4, 787-795.
Muthaura, C.N., Rukunga, G.M., Chhabra, S.C., Omar, S.A., Guantai, A.N., Gathirwa, J.W., Tolo, F.M., Mwitari, P.G., Keter, L.K., Kirira, P.G., Kimani, C.W., Mungai, G.M., Njagi, E.N.M., 2007. Antimalarial activity of some plants traditionally used in treatment of malaria in Kwale District. J. Ethnopharmacol. 112, 545-555.
Oloyede, G.K., Ibok, M.G., Ojo, T.K., 2021. Chemical constituents, antimicrobial and antioxidant activities of Leptoderris brachyptera (Benth.) Dunn and Leptoderris micrantha Dunn essential oils. Trends Phytochem. Res. 5(1), 13-23.
Sixsmith, D.G., Walkins, W.M., Chulay, J.D., Spencer, H.L., 1984. In vitro antimalarial activity of tetrahydrofolate dehydrogenase inhibition. Am. J. Trop. Med. Hyg. 33, 772-776.
Thagriki, D.S., Ray, U., 2022. An overview of traditional medicinal plants as dengue virus inhibitors. Trends Phytochem. Res. 6(2), 116-136.
Verdcourt, B., 1954. Notes on the Tropical African Canellaceae. East African Herbarium, Nairobi, Kenya.
Vignesh, A., Pradeepa Veerakumari, K., Selvakumar, S., Rakkiyappan, R., Vasanth, K., 2021. Nutritional assessment, antioxidant, anti-inflammatory and antidiabetic potential of traditionally used wild plant, Berberis tinctoria Lesch.. Trends Phytochem. Res. 5(2), 71-92.
World Health Organisation (WHO). 2020. World Malaria Report 2021, Geneva.
World Health Organization (WHO). 2001. In vitro Micro-test for Assessment of Response of Plasmodium falciparum to Chloroquine, Mefloquine, Quinine, Amodiaquine and Artemisinin, Geneva.
Wube, A.A., Bucar, F., Gibbons, S., Asres, K., 2005. Sesquiterpenes from Warburgia and their microbial activity. Phytochemistry 66, 2309-2315.
Wube, A.A., Bucar, F., Gibbons, S., Asres, K., Lauren, R., Simon, L.C., 2010. Antiprotozoal activity of drimane and coloratane sesquiterpenes towards Trypanosoma brucei rhodesience and Plasmodium falciparum in vitro. Phytother. Res. 24, 1468-1472.
