A review: secondary metabolites of Uvaria chamae p. Beauv. (Annonaceae) and their biological activities

Year 2018, Volume: 2 Issue: 4, 177 - 185, 20.12.2018

Thomas Abu Edia Rex-ogbuku Koki Idibiye

https://doi.org/10.31015/jaefs.18031

Cited By: 8

Abstract

Uvaria chamae p. Beauv., synthesizes and accumulates a variety of secondary metabolites from its root,
stem, leaf and fruit. These consist mainly of essential oils, flavonoids, alkaloids
and annonaceous acetogenins. Some of these biologically active secondary
metabolites validate the claim made in traditional system of medicine. The
present review summarizes the information available on the secondary
metabolites isolated from U. chamae and their biological activities.

Keywords

Secondary metabolites, alkaloids, Essential oils, Flavonoids, Annonaceous acetogenins

References

• Abu T., Ajaiyeoba E.O., Abiodun O.O., Ogbole OO. 2018. Antioxidant and anti-inflammatory intestinal effect of Uvaria chamae P. Beauv (Annonaceae) in acetic acid-induced acute colitis in rats. Book of Abstract, The Nigerian society of Pharmacognosy (NSP) 30th AGM/14th scientific conference; Page 48.
• Achenbach, H., Hohn, M., Waibel, R., Nkunya, M.H.H., Jonker, S.A. & Muhie, S. (1997). Oxygenated pyrenes, their potential biosynthetic precursor and benzylated dihydroflavones from two African Uvaria species. Phytochemistry; 2:395-364. http://dx:doi.org/10.1016/s0031-9422(96) 00448-7.
• Adams, M.R. & Moss M.O. (1999). Food Microbiology. Cambridge: The Royal Society of Chemistry, pp. 471 – 476. Adepiti A.O., Taiwo, O.E., Dada, A.D. (2013). Evaluation of the in vivo antimalarial potentials of the leaf and fruit of Uvaria chamae P. Beauv. (Annonaceae). Planta medica, 013.
• Ake-Assi, L., Abeye, J., Guinko, S., Giguet, R. &Bangavou, Y. (1981). Contribution l’identificationet au recensement des plantes utilises dans la medicine traditionnelle et la pharmacopéeen. Republique Centrafricaine. Paris, Agencede Cooperation Culturelle et Technique.
• Alali, F.Q., Liu, X.X. & McLaughlin, J.L. (1999).Annonaceous acetogenins: Recent progress. J. Nat. Prod., 62, 504–540.http://dx:doi.org/10.1021/np980406d.
• Anam, E.M., Ekpa, O.D., Gariboldi, P.V., Morah, F.N.I. & Dosunmu, M.I. (1993). 6”-Hydroxybenzyl diuvaretins and related-compounds from Xylopia africana (Benth) Oliver. Indian J. Chem. B; 32:1051–1054.
• Arbonnier, M. (2000).Arbres, arbustesetlianes des zones sechesd’Afrique de l’ouest. CIRAD, MNHN, UICN. 541pp.
• Arbonnier, M. (2004).Trees, Shrubs and Lianas of West African Dry Zones. Germany: CIRAD Press Ltd. pp. 243 - 248.Verdict Press, p. 191.
• Awodiran, M.O., Adepiti, A.O. & Akinwunmi, K.F. (2017).Assessment of the cytotoxicity and genotoxicity properties of Uvaria chamae P. Beauv (Annonaceae) and Morinda lucida Benth (Rubiaceae) in mice. Drug and chemical toxicology, http://dx:doi.org/10.1080/01480545.2017.1365884.
• Ayedoun, M.A., Moudachirou, M., Adeoti, B.S., Menut, C., Lamaty, G. & Bessiére, J.M. (1999).Aromatic plants of Tropical West Africa. VII. Essential oil of leaf and root bark of Uvaria chamae P. Beauv. from Benin. Journal of Essential Oil Research 11:23-26. http://dx:doi.org/10.1080/10412905.1999.9701060.
• Basil, N. I. (2017). Antioxidant Activity of Cnestis ferruginea and Uvaria chamae Seed Extracts. British Journal of Pharmaceutical Research; 16(1): 1-8. http://dx:doi.org/10.9734/BJPR/2017/32924.
• Bermejo, A., Figadere, B., Zafra-Polo, M.C., Barrachina, I., Estornell, E. & Cortes, D. (2005). ‘Acetogenins from Annonaceae: Recent progress in isolation , synthesis and mechanisms of action’. Natural product reports; 22(2):269-303.http://dx:doi.org/10.1039/B500186M
• Bhawna, S. &Kumar, S.U. (2009). Hepatoprotective activity of some indigenous plants.Int. J. of Pharm. Tech. Res.; 4:1330-1334.
• Bindu. T. K. (1998). “Phytochemical investigation of a few plants” Thesis. Department of Chemistry, University of Calicut.
• Bongers, F., Parren, M.P.E. & Traore, D. (2005). Forest Climbing Plants of West Africa: Diversity, Ecology and Management. CAB International. Raton, Florida, 145.
• Borges, M.H., Alves, D.L.F., Raslan, D.S., Pilo-Veloso, D., Rodrigues, V.M., Homsi-Brandeburgo, M.I. & De Lima, M.E. (2005). Neutralizing properties of Musa paradisiaca L. (Musaceae) juice on phospholipase A2, myotoxic, hemorrhagic and lethal activities of crotalidae venoms. J. Ethnopharmacol.; 98:(1-2):21-29. http://dx:doi.org/10.1016/j.jep.2004.12.014.
• Borokini, T.I. & Omotayo, F.O. (2012). Phytochemical and ethnobotanical study of some selected medicinal plants from Nigeria. Journal of Medicinal Plants Research; 6(7):1106-1118. http://dx:doi.org/10.5897/JMPR09.430.
• Burkill, H.M. (2000). The useful plants of West Tropical Africa II. Bot. Gardens, Kew (k), 1: 481.
• Burkill, HM. (2004).The Useful Plants of West Tropical Africa.Royal Botanic Gardens, Kew Pp 278-283.
• Chih, H.W., Chiu, H.F., Tang, K.S., Chang, F.R. &Wu, Y.C. (2001). Bullatacin, a potent antitumor annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction. Life Sci., 69, 1321–1331.http://dx:doi.org/10.1016/S0024-3205(01)01209-7.
• Choi, J.S., Yokozawa, T. & Oura, H. (1991). Improvement of hyperglycaemia and hyperlipemia in streptozotocin-diabetic rats by a methanol extract of Prunus davidiana stems and its main component, Prunin. Planta Medica; 57: 208-11. http://dx:doi.org/10.1055/s-2006-960075.
• De Lima, A.B. (2008). Estudo da AçãoAntinociceptiva e Antiinflamatóriado 1-Nitro-2-feniletano, Pricipal Constituinte da Anibacanelilla.M. S. Thesis, Universidade de Federal doPará, Belém, Brazil.
• Derbre´, S., Poupon, E., Gleye, C. & Hocquemiller, R.J. (2004). Nat. Prod., 70: 300.
• Ebi, G.C.U., Ifeanachoa, C.J. & Kamalub, T.N. (1999). Antimicrobial properties of Uvaria chamae stem bark. Fitoterapia 70: 621-624.http://dx:doi.org/10.1016/S0367-326X(99)00099-4.
• El-Soly, H.N., Lasswell, W.L. Jr. & Hufford, C.D. (1979). Two new c-benzylated flavanones from Uvaria chamae and 13C NMR analysis of flavanone methyl ethers. Journal of natural products; 42(3):264-270.http://dx:doi.org/10.1021/np50003a003.
• Emordi J.E., Agbaje E.O., Oreagba I.A. & Iribhogbe I.O. (2016).Antidiabetic and hypolipidemic activities of hydroethanolic root extract of Uvaria chamae in streptozotocin induced diabetic albino rats. BMC Complementary and Alternative Medicine; 16:468. http://dx:doi.org/10.1186/s12906-016-1450-0.
• Ene, A.C., Egbosi, N.C., Obika, C.J., Ibegbulem, C.O., Ujowundu, C.O. &Alisi, C.S. (2016). In vivo Antiplasmodial Activity of Ethanol and Aqueous Extracts of Uvaria chamae and Phyllantus amarus Plants. Futo Journal Series; 2(2):83 – 97.
• Etukudo, I. (2003). Ethnobotany: Conventional and Traditional Uses of Plants. The Verdict Press,Uyo, Nigeria. 191p.
• Fahn A (1974). Plant Anatomy. Second Edition, Pergamon Press, Oxford, pp. 12-550.
• Fall, D., Gleye, C., Franck, X., Laurens, A. & Hocquemiller, R. (2002). Cis-bullatencin, a linear acetogenin from roots of Uvaria chamae. Natuaral Product Letter; 16(5):315-21. http://dx:doi.org/10.1080/10575630290026437.
• Fall, D., Duval, R.A., Gleye, C., Laurens, A. & Hocquemiller, R. (2004).Chamuvarinin, an acetogenin bearing a tetrahydropyran ring from the roots of Uvaria chamae. Nat. Prod., 67:1041. http://dx:doi.org/10.1021/np030521a.
• Fall, D., Pimentel, L., Champy, P., Gleye, C., Laurens, A. &Hocquemiller, R. (2006).A new adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Uvaria chamae. Planta medica; 72(10):938-940. http://dx:doi.org/10.1055/s2006-941542.
• Grau, A. &Ortiz, A. (1998). Dissimilar protection of tocopherol isomers against membrane hydrolysis by phospholipase A2.Chem Phys Lipids; 91(2):109-118. http://dx:doi.org/10.1016/S0009-3084 (97)00101-1
• Hassig, A., Liang, W.X., Schwab, H. &Stampfli, K. (1999). Flavonoids and tannins: Plant-based antioxidants with vitamin character. Med Hypotheses; 52: 479–81. http://dx:doi.org/10.1054/mehy.1997.0686.
• Hertog, M.G.L., Feskens, E.J.M, Hollman, D.C.H., Katan, M.B. & Kromhout, D. (1993). Dietary antioxidant flavonoids and risk of coronary heart disease.The Zutphen Elderly study. Lancet, 342: 1077-1011. http://dx:doi.org/10.1016/0140-6736(93)92876-U.
• Hufford C.D. & Lasswell W.J Jr. (1976).Uvaretin and Isouvaretin. Two novel cytotoxic c-benzyl flavanone from Uvaria chamae. J. Org. Chem., 41(7):1297-1298. http://dx:doi.org/10.1021/j000869a062.
• Hufford, C.D. & Oguntimein, B.O. (1980). Dihydrochalcones from Uvaria angolensis. Phytochem; 19(9):2036-2038. http://dx:doi.org/10.1016/S0031-9422(80) 83036-6.
• Hufford, C.D. & Lasswell, W.L., (1978). Anti-microbial activities of constituents of Uvaria chamae.Lloydia , 41,156–160.
• Igoli, J.O., Ogaji, O.G., Tor-Anyiin, T.A. & Igoli, N.P. (2005). Traditional Medicine Practice amongst the Igede People of Nigeria. Part II. Afr. J. Trad. CAM. 2(2): 134 – 152.
• Iwu, M.M. (1993). Handbook of African Medicinal Plants.CRC Press, Boca.22.495.
• Katerere, D.R., Gray, A.I., Nash, R.J. &Waigh, R.D. (2012). Phytochemical and antimicrobial investigations of stilbenoids and flavonoids isolated from three species of Combretaceae. Fitoterapia, 83(5):932-940. http://dx:doi.org/10.1016/j.fitote.2012.04.011.
• Kone, M., Toure, A., Ouattara, K. &Coulibaly, A. (2015). Phytochemical Composition, Antioxidant and Antibacterial Activities of Root of Uvaria chamaeP. Beauv. (Annonaceae) Used in Treatment of Dysentery in North of Côte d’Ivoire. International Journal of Pharmacognosy and Phytochemical Research; 7(6); 1047-1053.
• Lasswell, W.J Jr. & Hufford C.D. (1977). Cytotoxic c-benzylatedflavanoids from Uvaria chamae. Phytochem., 16:1441. http://dx:doi.org/10.1021/jO00428a006.
• Liu, R., Gao, M., Yang, ZH. & Du, GH. (2008). Pinocembrin protects rat brain against oxidation and apoptosis induced by ischemia-reperfusion both in vivo and in vitro. Brain Res., 1216:104-115. http://dx:doi.org/10.1016/j.brainres.2008.03.049.
• Liu, X., Kim, J., Li, Y., Li, J., Liu, F. & Chen, X. (2005). Tannic acid stimulates glucose transport and inhibits adipocyte differentiation in 3T3-Li cells. J Nutr.; 135: 165-71.
• Mabberly, D.J. (1997). The Plant – Book, 2nd Ed. Cambridge University Press, UK, 41-42.
• McLaughlin, J.L. (2008). Paw Paw and Cancer: Annonaceous Acetogenins from Discovery to Commercial products. Journal of Natural products; 71(7):1311-1321. http://dx:doi.org/10.1021/np800191t.
• Madubunyi, I.I., Njoku, C.J., Ibeh, E.O. &Dume A.B. (1996).Antihepatotoxic and trypanocidal effects of the root bark extract of Uvaria chamae. International Journal of pharmacognosy; 34(1):34-40.
• Madubunyi, II. (2012). Hepatoprotective activity of Uvariachamae root bark methanol extract against acetaminophen-induced liver lesions in rats.Comparative Clinical Pathology; 21(2):127-135.http://dx:doi.org/10.1007/S00580-010-1072-8.
• Manikandan, L., Senthilkumar, GP., Rajesh, L.T. & Suresh, R. (2006). Cancer chemoprotective agents from medicinal plants. In: Trivedi PC (ed). Medicinal Plants: Ethnobotanical approach. Agrobios., India. P. 410.
• Mariita, P.M., Ogol, C.K.P.O., Oguge, N.O. & Okemo, P.O. (2011). Methanol extract of three medicinal plants from samburu in Northern Kenya show significant antimycobacterial, antibacterial and antifungal properties. Res. J. of Med. Plant, 5:54-64. http://ir-library.ku.ac.ke/handle/123456789/5932.
• Marshall, S.J., Russel, P.F., Phillipson J.D., Kirby, G.C., Warhurst, D.C. &Wight, C.W. (2000). Antiplasmodial and antiamoebic activities of medicinal plants from Sieria Leone. Phytotherapy Research; 14(5):356-358. http://dx:doi.org/10.1002/1099-1573(200008)14:5<356::AID-PTR636>3.0.CO; 2-Z.
• Meiselman, H.L., Halpern, B.P. & Dateo, G.P. (1976). Reduction of sweetness judgments by extracts from the leaves of Ziziphus jujuba. Physiol Behavior; 17: 313-17. http://dx:doi.org/10.1016/0031-9384(76)90081-0.
• Metzner, J. & Schneidewind, E.M. (1978). Effect of pinocembrin on the course of experimental Candida infections in mice. Mykosen, 21(8):257-262.
• Moreno, J.J. (1993). Effect of aristolochic acid on arachidonic acid cascade and in vivo models of inflammation. Immunopharmacology; 26(1):1-9. http://dx:doi.org/10.1016/0162-3109(93)90061-T.
• Moses, S.O., Olowu, R., Adewale, N.S.D. &William, N.S. (2013). 1-Nitro-2-phenylethane dominates the chemical composition of the leaf essential oil of Uvaria chamae from Badagry, Nigeria. American Journal of Essential Oils and Natural Products; 1 (1): 48-50.
• Moukimou,A.O., dc Pascal, A., Annick, B., Yaya, K., Pierre, N.A., Felicien, A. &Dominique S.K. (2014). Chemical characterization and biological activities of extracts of three plants used in traditional medicine in Benin: Tectona grandis, Uvaria chameae and Justicia secunda. Asian J Pharm Clin Res, 7(5): 23-27.
• Negbenebor, H. E., Makanjuola, W. A., Denloye, A. A. and Nura, S. (2018). Toxicity of powdered and ethanolic extracts of Uvaria chamae (Annonaceae) Bark on selected stored product insect pests. African Journal of Biotechnology, Vol. 17(11), pp. 350-355. http://dx:doi.org/10.5897/AJB2017.16257
• Nkunya, M.H.H., Weenen, H., Reener, C., Waibel, R. & Achenbach, H. (1993). Benzylated dihydrochalcones from Uvaria leptocladon. Phytochemistry; 32(5):1297-1300. http://dx:doi.org/10.1016/S0031-9422(00)95109-4.
• Nwosu, M. (2000). Plant resources used by women as herbal medicines and cosmetics in Southeastern Nigeria. Arztezeitschrift for naturopathy, 41(11):760-7.
• Oguntimein, B., Ekundayo, O., Laakso, I. & Hiltunen, I. (1989). Volatile constituents of Uvaria chamae leaves and root bark. Planta Medica 55:312-313. http://dx:doi.org/10.1055/S-2006-962016.
• Okorie, D.A. (1977). New benzyldihydrochalcones from Uvaria chamae. Phytochem.; 16(10):1591-1594. http://dx:doi.org/10.1016/0031-9422(77) 84030-2.
• Okwu, D.E, & Iroabuchi, F. (2009). Phytochemical Composition and Biological Activities of Uvaria chamae and Clerodendoron splendens.E-J Chem.; 6:553–60.
• Oluremi, B.B. & Adeniji, J.A. (2015).Anti-viral Activity Evaluation of Selected Medicinal Plants of Nigeria against Measles Virus. British Microbiology Research Journal; 7(5): 218-225. http://dx:doi.org/10.9734/BMRJ/2015/16220.
• Oluremi, B.B., Osungunna, M.O. & Omafuma O.O. (2010). Comparative assessment of antibacterial activity of Uvaria chamae parts. Afr. J. Microbiol. Res. 4 (13):1391-1394.
• Omale, J., Ebiloma U.G. & Idoko G.O. (2013). Uvaria chamae (Annonaceae) plant extract neutralizes some biological effects of Naja nigricollis snake venom in rats. Br. J. Pharmacol. Toxicol., 4(2):41-50.
• Park, R. J. & Sutherland, M. D. (1969). Some constituents of Apium leptophyllum (d.C.) F. Muell. in relation to tainting of milk. Australian J. Chem., 22(3):495-6.
• Peana, A.T., D’Aquila, P.S., Chessa, M.L., Moretti, M.D.L., Serra, G. &Pippia, P. (2003). (–)-Linalool produces antinociception in two experimental models of pain. Eur. J. Pharmacol., 460:37-41.http://dx:doi.org/10.1078/094471102321621322.
• Peana, A.T., D’Aquila, P.S., Panin, F., Serra, G., Pippia, P. & Moretti, M.D.L. (2002). Anti-inflammatory activity of linalool and linalyl acetate constituents of essential oils. Phytomedicine; 9:721-726.
• Philipov, S., Ivanovska, N., Istatkova, R., Velikova, M. & Tuleva, P. (2000). Phytochemical study and cytotoxic activity of alkaloids from Uvaria chamae P. Beauv. Die Pharmazie; 55:688-689.
• Ruddock, P.S., Charland, M., Ramirez, S., Lopez, A., Neil Towers, G.H., Arnason, J.T., Liao, M. & Dillon, J.A. (2011). Antimicrobial activity of flavonoids from piper lanceaefolium and other Colombian medicinal plants against antibiotic susceptible and resistant strains of Neisseria gonorrhoeae. Sex Transm Dis., 38(2):82-88.http://dx:doi.org/10.1097/OLQ.Ob013e3181fobdbd
• Sala, A., Recio, M.C., Schinella, G.R., Manez, S., Giner, R.M., Cerda-Nicolas, M. &Rosi, J.L. (2003). Assessment of the anti-inflammatory activity and free radical scavenger activity of tiliroside. Eur. J. Pharmacol., 461(1):53-61. http://dx:doi.org/10.1016/S0014-2999(02)02953-9.
• Salisbury, F.B, & Ross, C.W. (1992).‘Mineral nutrition’. Plant Physiology. Wadsworth pp. 357-407, pp. 531-548.
• Sofowora, E.A (1982). The State of Medicinal Plants’ Research in Nigeria. Ibadan University Press, Nigeria, p. 404.
• Soromou, L.W., Chu, X., Jiang, L., Wei, M., Huo, M., Chen, N., Guan, S., Yang, X., Chen, C., Feng, H. & Deng, X. (2012). In vitro and in vivo protection provided by pinocembrin against lipopolysaccharide-induced inflammatory responses. Int. immunopharmacol., 14(1):66-74. http://dx:doi.org/10.3109/1547691X.2013.7
• Suba, V., Murugesan, T., Rao, B.R., Ghosh, L., Pal, M., Mandal, S.C. & Saha, B.P. (2004). Antidiabetic potential of Barleria lupulina extract in rats. Fitoterapia, 75: 1-4. http://dx:doi.org/10.1078/0944-7113-00316.
• Tempesta, M.S., Kriek, G.R. &Bates, R.B. (1982). Uvaricin, a new antitumor agent from Uvaria accuminata (annonaceae). J. Org. Chem., 47, 3151–3153. http://dx:doi.org/10.1021/j000137a024
• Thierry, C.A., Joachim, D.G., Salomé Kpoviessi, D.S., Georges, C.A, Moudachirou, M. & Gbeassor, M. (2012). Antihemolytic Properties of Extracts of Six Plants Used in the Traditional Treatment of Sickle Cell Disease in Benin. Journal of Applied Pharmaceutical Science, 02 (03): 08-13.
• Trease, G.E & Evans, W.C. (1989). Textbook of Pharmacognosy.14th Edition.W.B. Sanders, London.
• Uzel, A., Sorkun, K., Oncag, O., Cogulu, D., Gencay, O. & Salih, B. (2005). Chemical compositions and antimicrobial activities of four different Anatolian propolis samples. Microbiol. Res., 160(2):189-195.http://dx:doi.org/10.1016/j.micres.2005.01.002.
• Zafra-Polo, M.C., Figadère, B., Gallardo, T., Tormo, J. & Cortes, D. (1998). Natural acetogenins from annonaceae, synthesis and mechanisms of action.Phytochemistry; 48(7):1087–1117. http://dx:doi.org/10.1016/S0031-9422(97)00917-5.
• Zafra-Polo, M.C., González, M.C., Estornell, E., Sahpaz, S. & Cortes, D. (1996). Acetogenins from annonaceae, inhibitors of mitochondrial complex I. Phytochemistry, 42, 253–271. http://dx:doi.org/10.1016/0031-9422(95)00836-5.