Triterpenes from Urtica dioica L. roots of Ethiopian origin
محورهای موضوعی : Natural Products: Isolation and Characterization
Tegene Tole
1
(Chemistry Department, College of Natural and Computational Sciences, Hawassa University, P.O. Box 5, Hawassa, Ethiopia)
کلید واژه: Ursane type, Antidiabetic, Dihydroxy ursolic acid, Hepato-protective, ursolic acid, <i>Urtica dioica</i> L,
چکیده مقاله :
Urtica dioica L. (family Urticaceae) is an herbaceous shrub originally from the colder regions of northern Europe and Asia grows today all over the world. It has a long history of use in the household home remedies and nutritious diet. This study was conducted to investigate the chemical constituents of the root of Urtica dioica L. grown in Ethiopia. The secondary metabolite class screening test of n-hexane extract revealed the presence of alkaloids, saponins and terpenoids, whereas the chloroform crude extract showed the presence of phenols, flavonoids, and tannins in addition to the classes of secondary metabolites present in the n-hexane extract. The methanolic extract revealed the presence of alkaloids, glycosides, phenols, saponins, steroids, tannins, flavonoids, and terpenoids. The column chromatographic separation of the methanolic extract afforded two ursane-type pentacyclic triterpenes namely 3β-hydroxy-urs-12-ene-28-oic acid commonly known as ursolic acid and 3,7,24-trihydroxyl-urs-12-en-28-oic acid which is also known as 7,24 dihydroxy ursolic acid.
Adamski, Z., Blythe, L.L., Milella, L., Bufo, S.A., 2020. Biological activities of alkaloids: From toxicology to pharmacology. Toxins (Basel) 12(4), 210-213.
Ahmed, M.I., 2021. Phytochemical Screening and Antimicrobial Activities of Stinging Nettle (Urtica dioica L.) Leaf, Fruit and Root Extacts. MSc Thesis, Haramaya University, Haramaya, Ethiopia.
Akgeul, A., 1993. Spies Science and Technology. Association Food Technology, Publ. No: 15. Ankara, Turkey.
Anees, A.S., Farah, I., Seemi, S., Kapendra, S., 2014. Role of natural products in drug discovery process. Int. J. Drug. Dev. Res. 6(2), 172-204.
Aziz, R.A., Sarmidi, M.R., Kumaresan, S., 2003. Phytocehemical processing: The next emerging field in chemical engineering aspects and opportunities. J. Kejurut. Kim Malay 3, 45-60.
Barrett, D., 2002. From natural products to clinically useful antifungals. Biochim. Biophys. Acta. 1587(2-3), 224-233.
Baytop, T., 1989. Therapy with Plant in Turkey. Istanbul University, Faculty of Pharmacy (Second Press). Nobel Medicine Bookstores, Istanbul, Turkey.
Bhattaram, V.A., Graefe, U., Kohlert, C., Veit, M., Derendorf, H., 2002. Pharmacokinetics and bioavailability of herbal medicinal products. Phytomedicine 9(Suppl 3), 1-33.
Bhuwan, C.J, Minky, M., Ajudhia, N.K.. 2014. Pharmacognostical review of Urtica dioica L. Int. J. Green Pharm. 8, 201-209.
Bisht, S., Bhandari, S., Bisht, N.S., 2012. Urtica dioica (L): An undervalued, economically important plant. Int. Res. J. 2(5), 250-252.
Bradley, P., 1992. Ed. British Herbal Compendium. Dorset, England: British Herbal Medicine Association; 1, 166-167.
Brodal, P., 2004. The Central Nervous System: Structure and Function. Oxford University Press, pp., 170.
Chrubasik, S., Enderlein, W., Bauer, R., Grabner, W., 1997. Evidence for antirheumatic effectiveness of Herba Urticae dioica in acute arthritis: A pilot study. Phytomedicine 4(2), 105-108.
Cordell, G.A., 2002. Recent developments in the study of biologically active natural products. ACGC Chem. Commun. 14, 31-63.
Dhanani, T., Shah, S., Gajbhiye, N.A., Kumar, S., 2017. Effect of extraction methods on yield, phytochemical constituents and antioxidant activity of Withania somnifera. Arab. J. Chem. 10(Suppl 1), 1193-1199.
Does, M.P., Ng, D.K., Dekker, H.L., Peumans, W.J., Houterman, P.M., Van Damme, E.J., Cornelissen, B.J., 1999. Characterization of Urtica dioica agglutinin isolectins and the encoding gene family. Plant Mol. Biol. 39(2), 335-347.
Đurović, S., Pavlić, B., Šorgić, S., Popov, S., Savić, S., Petronijević, M., Radojković, M., Cvetanović, A., Zeković, Z., 2017. Chemical composition of stinging nettle leaves obtained by different analytical approaches. J. Funct. Foods 32, 18-26.
Ernst, E., Chrubasik, S., 2000. Phyto-anti-inflammatories: A systematic review of randomized, placebo-controlled, double-blind trials. Rheum. Dis. Clin. North Am. 26(1), 13-27.
Farag, M.A., Weigend, M., Luebert, F., Brokamp, G., Wessjohann, L.A., 2013. Phytochemical, phylogenetic, and anti-inflammatory evaluation of 43 Urtica accessions (stinging nettle) based on UPLC-Q-TOF-MS metabolomic profiles. Phytochemistry 96, 170-183.
Fischer, C., 1997. Nettles-an aid to the treatment of allergic rhinitis. Eur. Herbal Med. 3(2), 34-35.
Ganesh, S., Vennila, J., 2011. Phytochemical analysis of Acanthus ilicifolius and Avicennia ofcinalis by GC-MS. Res. J. Phytochem. 5(1), 60-65.
Gnoatto, S.C.B., Dassonville-Klimpt, A., Da Nascimento, S., Galera, P., Boumediene, K., Gosmann, G., Sonnet, P., Moslemi, S., 2008. Evaluation of Ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition. Eur. J. Med. Chem. 43(9), 1865-1877.
Gulcin, I., Kufre, O., Oktay, M., Buyuko, E., 2004. Antioxidant, antimicrobial, anticancer and analgesic activities of U. dioica. J. Ethnopharmacol. 90(2-3), 205-215.
Harwood, M.B., Danielewska, J.F., Borzelleca, G.W., Flamm, G.M., Williams, T.C., 2007. A critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic/carcinogenic properties. Food Chem. Toxicol. 45(11), 2179-2205.
Hayouni, E.A., Abedrabba, M., Bouix, M., Hamdi, M., 2007. The effects of solvents and extraction method on the phenolic contents and biological activities in vitro of Tunisian Quercus coccifera L. and Juniperus phoenica L. fruit extracts. Food Chem. 105(3), 1126-1134.
Ilies, D.C., Tudor, I., Radulescu, V., 2012. Chemical composition of the essential oil of Urtica dioica. Chem. Nat. Comp. 48(3), 506-507.
Ishida, B.K., Ma, J., Bock, C., 2001. A simple rapid method for HPLC analysis of lycopene isomers. Phytochem. Anal. 12(3), 194-198.
Jacob, R.A., Burri, B.J., 1996. Oxidative damage and defense. Am. J. Clin. Nutr. 63(6), 985S-990S.
Ji, H.F., Li, X.J., Zhang, H.Y., 2009. Natural products and drug discovery. Can thousands of years of ancient medical knowledge lead us to new and powerful drug combinations in the fight against cancer and dementia? EMBO Rep. 10(3), 194-200.
Joshi, N., Pandey, S.T., 2007. Stinging nettle (Urtica dioica)-history and its medicinal uses. Asian Agrihist. 21(2), 133-138.
Juang, Y.P., Liang, P.H., 2020. Biological and pharmacological effects of synthetic saponins. Molecules 25(21), 4974.
Kinghorn, A.D., Pan, L., Fletcher, J.N., Chai, H., 2011. The relevance of higher plants in lead compound discovery programs. J. Nat. Prod. 74(6), 1539-1555.
Kumar, S., Pandey, A.K., 2013. Chemistry and biological activities of flavonoids: An overview. Sci. World J. 2013, 162750.
Le Moal, M.A., Truffa-Bachi, P., 1988. Urtica dioica agglutinin, a new mitogen for murine T lymphocytes: Unaltered interleukin-1 production but late interleukin 2-mediated proliferation. Cell Immunol. 115(1), 24-35.
Li, J.W., Vederas, J.C., 2009. Drug discovery and natural products: End of an era or an endless frontier? J. Sci. 325 (5937), 161-165.
Lukesova, H., 2017. Identifying plant fiber textiles from Norwegian Merovingian Period and Viking Age graves: The Late Iron Age Collection of the University Museum of Bergen. J. Archaeol. Sci. Reports. 13, 281-285.
Manganelli, R.E., Uncini, L.Z., Tomei, P.E., 2005. Antiviral activity in vitro of Urtica dioica L., Parietariadiffusa M. et K. and Sambucus nigra L. J. Ehnopharmacol. 98(3), 323-327.
Mazumder, K., Siwu, E.R.O., Nozaki, S., Watanabe, Y., Tanaka, K., Fukase, K., 2011. Ursolinic acid derivatives from Bangladeshi medicinal plant, Saurauja roxburghii: Isolation and cytotoxic activity against A431 and C6 glioma cell lines. Phytochem. Lett. 4(3), 287-291.
Mazumder, K., Tanaka, K., Fukase, K., 2013. Cytotoxic activity of ursolic acid derivatives obtained by isolation and oxidative derivatization. Molecules 18(8), 8929-8944.
Mlala, S., Oyedeji, A.O., Gondwe, M., Oyedeji, O.O., 2019. Ursolic acid and its derivatives as bioactive agents. Molecules 24(15), 2751-2775.
Mohammadhosseini, M., Frezza, C., Venditti, A., Akbarzadeh, A., 2019a. Ethnobotany and phytochemistry of the genus Eremostachys Bunge. Curr. Org. Chem. 23, 1828-1842.
Mohammadhosseini, M., Venditti, A., Flamini, G., Sarker, S.D., Kalaee, M., 2022. The genus Micromeria Benth.: An overview on ethnobotany, chemotaxonomy and phytochemistry. Trends Phytochem. Res. 6(3), 155-186.
Olaoluwa, O., Taiwo, O., Nahar, L., Sarker, S.D., 2022. Ethnopharmacology, phytochemistry and biological activities of the African species of the genus Ficus L. Trends Phytochem. Res. 6(1), 46-69.
Newman, D.J., Cragg, G.M., Snader, K.M., 2003. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 66(7), 1022-1037.
Ngo, L.T., Okogun, J.I., Folk, W.R., 2013. 21st Century natural product research and drug development and traditional medicines. J. Nat. Prod. Rep. 30(4), 584-592.
Pakrashi, C.S., Datta, S., Ghosh-Dastidar, P.P., 1968. Indian medicinal plants-XVII.3 Phytochemical examination of Carissa SPP. Phytochemistry 7(3), 495-496.
Pashazadeh, M., Rahbani, M., Zakhireh, S., 2013. Effect of Nettle oil (Urtica dioica) consumption on levels of blood glucose and lipids in alloxan-induced diabetic rats. Bull. Env. Pharmacol. Life Sci, 2(10), 84-89.
Prashant, T., Bimlesh, K., Mandeep, K., Gurpreet, K., Harleen, K., 2011. Phytochemical screening and extraction: A review. Int. Pharm. Sci. 1(1), 98-106.
Riehemann, K., Behnke, B., Schulze-Osthoff, K., 1999. Plant extracts from stinging nettle (Urtica dioica), an antirheumatic remedy, inhibit the proinflammatory transcription factor NF-κB. FEBS Lett. 442(1), 89-94.
Rout, S.P., Choudary, K.A., Kar, D.M., Das, L., Jain, A., 2009. Plants in traditional medicinal system-future source of new drugs. Int. J. Pharm. Pharm. Sci. 1(1), 1-23.
Seebacher, W., Simic, N., Weis, R., Saf, R., Kunert, O., 2003. Complete assignments of 1H and 13C NMR resonances of oleanolic acid, 18α‐oleanolic acid, ursolic acid and their 11‐oxo derivatives. Magn. Reson. Chem. 41(8), 636-638.
Serrano, J., Puupponen-Pimi, R., Dauer, A., Aura, A.M., Saura-Calixto, F., 2009. Tannins: Current knowledge of food sources, intake, bioavailability and biological effects. Mol. Nutr. Food Res. 53, 310-329.
Silva, I.F., Oliveira, F.F.d., Oliveira, R.A.d., 2021. Siparuna Aublet genus (Siparunaceae): From folk medicine to chemical composition and biological activity. Trends Phytochem. Res. 5(4), 168-189.
Sitrallah, S., Merza, J., 2018. Chemical composition of essential oil extracted from Urtica pilulifera and evaluation of its biological activity. Food Sci. Qual. Manag. 78, 44-48.
Soto-Blanco, B., 2022. Chapter 12-Herbal Glycosides in Healthcare, Editor(s): Subhash C. Mandal, Amit Kumar Nayak, Amal Kumar Dhara, Herbal Biomolecules in Healthcare Applications, Academic Press, pp. 239-282.
Taheri, Y., Quispe, C., Herrera-Bravo, J., Sharifi-Rad, J., Ezzat, S.M., Merghany, R.M., Shaheen, S., Azmi, L., Prakash Mishra, A., Sener, B., Kılıç, M., Sen, S., Acharya, K., Nasiri, A., Cruz-Martins, N., Tsouh Fokou, P.V., Ydyrys, A., Bassygarayev, Z., Daştan, S.D., Alshehri, M.M., Calina, D., Cho, W.C., 2022. Urtica dioica-derived phytochemicals for pharmacological and therapeutic applications. Evid. Based Complement. Alternat. Med. 4024331.
Upton, R., 2013. Stinging nettles leaf (Urtica dioica L.): Extraordinary vegetable medicine. J. Herb. Med. 3, 9-38.
Urtica dioica L. Plants of the World Online: Kew Royal Botanic Gardens. https://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:260630-2_accession date 12:29/2022.
Venditti, A., Guarcini, L., Ballero, M., Bianco, A., 2015. Iridoid glucosides from Pentas lanceolata (Forssk.) Deflers growing on the Island of Sardinia. Plant Syst. Evol. 301, 685-690.
Venditti, A., Lattanzi, C., Ornano, L., Maggi, F., Sanna, C., Ballero, Alvino, A., Serafini, M., Bianco, A., 2016. A new glucosidic phthalide from Helichrysum microphyllum subsp. tyrrhenicum from La Maddalena Island (Sardinia, Italy). Nat. Prod. Res. 30(7), 789-795.
Wagner, H., Willer, F., Kreher, B., 1989. Biologically active compounds from the aqueous extract of Urtica dioica. Planta Med. 55(5), 452-454.
Wetherilt, H., 1989. Isırgan Otu Yaprak Ve Tohumlarının Besleyici €ozelliklerive Antit €um €ore Etkileri. PhD Thesis, (Turkish). Hacettepe University. Graduate Institute of Health Science, Ankara, Turkey.
World Health Organization, 2002. National Cancer Control Programmes: Policies and Managerial Guidelines, 2nd Edn. Geneva, World Health Organization.