CYTOTOXIC AND ANTIOXIDANT ACTIVITIES OF SECONDARY METABOLITES FROM PULICARIA UNDULATA

  • Taha A. Hussien Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Egypt
  • Sayed A. El-toumy Chemistry of Tannins Department, National Research Center, El-Bohouth St., Dokki, 12622 Cairo, Egypt
  • Hossam M. Hassan Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Egypt
  • Mona H. Hetta Department of Pharmacognosy, Faculty of Pharmacy, Fayoum University, Egypt

Abstract

Objective: To evaluate the in vitro cytotoxicity, antioxidant activities and structure-activity relationship of secondary metabolites isolated from Pulicaria undulata.

Methods: The methylene chloride-methanol (1:1) extract of the air-dried aerial parts of Pulicaria undulata was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of the isolated compounds were determined on the basis of the extensive spectroscopic analysis, including 1D and 2D NMR and compared with the literature data. The crude extract and the isolated compounds were evaluated for in vitro antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method and cytotoxic assay using human breast cancer (MCF-7) and hepatoma (Hep G2) cell line.

Results: Nine secondary metabolites were isolated from Pulicaria undulata in this study. Of which two terpenoidal compounds; 8-epi-ivalbin and 11β, 13-dihydro-4H-xanthalongin 4-O-β-D-glucopyranoside firstly isolated from the genus pulicaria and three flavonoids; eupatolitin, 6-methoxykaempferol, and patulitrin firstly isolated from P. undulata. 6-methoxykaempferol (IC50 2.3 µg/ml) showed the most potent antioxidant activity. The highest cytotoxic effect against MCF-7 and Hep G2 cells was obtained with eupatolitin (IC50 27.6 and 23.5 µg/ml) respectively. The structure-activity relationship was also examined and the findings presented here showed that 3, 5, 7, 4' and 3, 5, 4', 5'-hydroxy flavonoids were potent antioxidant and has cytotoxic activity.

Conclusion: Pulicaria undulata is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as antioxidant drug and in the treatment of cancer.

Keywords: Pulicaria undulata, Sesquiterpenes, Ditepenoids, Flavonoids, Cytotoxicity, Antioxidant

Downloads

Download data is not yet available.

References

1. El-Shemy H, Aboul-Enein A, Aboul-Enein M, Issa S, Fujita K. The effect of willow leaf extract on human leukemic cells, in vitro. J Biochem Mol Biol 2003;36:387-9.
2. El-Shemy HA, Aboul-Enein AM, Aboul-Enein KM, Fujita K. Willow leaves’ extracts contain anti-tumor agents effective against three cell types. PLoS One 2007;2:178.
3. Vickers A. Botanical medicines for the treatment of cancer: rationale, an overview of current data, and methodological considerations for phase I and II trials. Cancer Invest 2002;20:1069-79.
4. Williams CA, Harborne BJ, Greenham JR, Grayer JR, Kite CG, Eagles J. Variations in lipophilic and vacuolar flavonoids among European Pulicaria species. Phytochemistry 2003;64:275-83.
5. Liu LL, Yang JL, Shi YP. Phytochemicals and biological activities of Pulicaria species. Chem Biodiversity 2010;7:327-49.
6. Al-Yahya AM, El-Sayed MA, Mossa SJ, Kozlowski FJ, Antoun DM, Ferin M, et al. Potential cancer chemopreventive and cytotoxic agents from Pulicaria crispa. J Nat Prod 1988;51:621-4.
7. Awadh AU, Juelich NA, Kusnick WO, Lindequist CU. Screening of Yemeni medicinal plants for antibacterial and cytotoxic activities. J Ethnopharmacol 2001;74:173-9.
8. EL-Kamali HH, Ahmed AH, Mohammed AS, Yahia AAM, EL-Tayeb IH, Ali AA. Antibacterial properties of essential oils from Nigella sativa seeds, Cymbopogon citratus, leaves and Pulicaria undulata aerial parts. Fitoterapia 1998;1:77-8.
9. Basta A, Tzakou O, Couladis M, Pavlovic M. Chemical composition of Pulicaria dysenterica (L.) Bernh. from Greece. J Essent Oil Res 2007;19:333-5.
10. Ezoubeiri A, Gadhi CA, Fdil N, Benharref A, Vanhaelen M. Isolation and antimicrobial activity of two phenolic compounds from Pulicaria odora L. J Ethnopharm 2005;99:287–92.
11. Tanira MOM, Ali BH, Bashir AK, Wasfi IA, Chandranath I. Evaluation of the relaxant activity of some United Arab Emirates plants on intestinal smooth muscle. J Pharm Pharmacol 1996;48:545-50.
12. Mahfouz M, Ghazal A, El-Dakhakhny M, Ghoneim MT. Pharmacological studies on the active principle isolated from Pulicaria dysenterica. J Drug Res 1973;5:151–72.
13. Hegazy M, Matsuda H, Nakamura S, Yabe M, Matsumoto T, Yoshikawa M. Sesquiterpenes from an Egyptian herbal medicine, Pulicari undulata, with inhibitory effects on nitric oxide production in RAW264.7 macrophage cells. Chem Pharm Bull 2012;60:363-70.
14. Yen GC, Duh PD. Scavenging effect of methanolic extract of peanut hulls on free radical and active oxygen species. J Agric Food Chem 1994;42:629-32.
15. Mosamnn T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55-63.
16. Gangadevi V, Muthumary J. Preliminary studies on the cytotoxic effect of fungal taxol on cancer cell lines. Afr J Biotechnol 2007;6:1382-6.
17. Herz W, Chikamatsu H, Viswanathan N, Sudarsanam V. Constituents of Iva species. VIII. The structure of ivalbin, a modified guaianolide from Iva dealbata Gray. J Org Chem 1967;32:682-6.
18. Claus MP, Irmgard M, Christoph B, Günter W, Alois S. 11a,13-and 11b,13-Dihydro-4H-xanthalongin 4-OGlucopyranosides: new sesquiterpene lactone glycosides from flowers of Arnica amplexicaulis and A. mollis. Planta Med 1996;62:39-41.
19. Karamenderes C, Bedir E, Abou-Gazar H, Khan AI. Chemical constituents of Centaurea cadmea. Chem Nat Compd 2007;43:694-5.
20. Abdel-Mogib M, Jakupovic J, Dawidar AM, Metwally MA, Abou-Elzahab M. Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry 1990;29:2581-4.
21. Eckhard W, Abdolhossein R. Exudate flavonoids in three Persian asteraceae species. Biochem Syst Ecol 1991;19:673-5.
22. Takaharu H, Hajime A, Hiroto C, Shigeharu F, Masashi K. Isolation and identification of anti-Helicobacter pylori compounds from Polygonum tinctorium Lour. Nat Med 1999;53:27-31.
23. Christine AW, Jeffrey BH, Jenny RG, Rene´e JG, Geoffrey CK, John E. Variations in lipophilic and vacuolar flavonoids among European Pulicaria species. Phytochemistry 2003;64:275-83.
24. Wiesława B. A new acylated flavonol diglycoside from Atriplex littoralis. Acta Physiol Plant 2004;26:393-8.
25. Pal RS, Ariharasivakumar G, Girhepunjhe K, Upadhay A. In the vitro antioxidative activity of phenolic and flavonoids compounds extracted from seeds of Abrus precatorius. Int J Pharm Pharm Sci 2009;1:136-40.
26. Francis D, Rita L. Rapid colorimetric assay for cell growth and survival: modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods 1986;89:271-7.
27. Burda S, Oleszek W. Antioxidant and antiradical activities of flavonoids. J Agric Food Chem 2001;49:2774–9.
28. Di Majo D, Giammanco M, La Guardia M, Tripoli E, Giammanco S, Finotti E. Flavanones in citrus fruit: structure-antioxidant activity relationships. Food Res Int 2005;38:1161-6.
29. Benavente-Garcia O, Castillo J, Marin FR, Ortuno A, Del Rio JA. Uses and properties of citrus flavonoids. J Agric Food Chem 1997;45:4505–15.
30. Bors W, Hellers W, Michel C, Saran M. Radical chemistry of flavonoids. Adv Exp Med Biol 1990;264:165–70.
31. Bors W, Hellers W, Michel C, Saran M. Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods Enzymol 1990;186:343–55.
32. Arora A, Nair MG, Strasburg GM. Structure–activity relationships for antioxidant activities of a series of flavonoids in a liposomal system. Free Radical Biol Med 1998;24:1355-63.
33. Rusakc G, Gutzeita HO, Muller JL. Structurally related flavonoids with antioxidative properties differentially affect cell cycle progression and apoptosis of human acute leukemia cells. Nutr Res 2005;25:141-53.
34. Plochmann K, Korte G, Koutsilieri E, Richling E, Riederer P, Rethwilm A, et al. Structure–activity relationships of flavonoid-induced cytotoxicity on human leukemia cells. Arch Biochem Biophys 2007;460:1-9.
35. Li F, Awale S, Tezuka Y, Kadota S. Cytotoxic constituents from Brazilian red propolis and their structure–activity relationship. Bioorg Med Chem 2008;16:5434–40.
36. Ducki S, Forrest R, Hadfield JA, kendall A, Lawrence NJ, Mcgown AT, et al. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett 1998;8:1051-6.
37. Pouge TC, Lauthier F, Simon A, Fagnere C, Basly JP, Delage C, et al. Flavonoids: structural requirements for antiproliferative activity on breast cancer cells. Bioorg Med Chem Lett 2001;11:3095–7.
38. Militao GC, Dantas IN, Pessoa C, Falcao MJ, Silveira ER, Lima MA, et al. Induction of apoptosis by pterocarpans from Platymiscium floribundum in HL-60 human leukemia cells. Life Sci 2006;78:2409–17.
39. Wang IK, Lin-Shiau SY, Lin JK. Induction of apoptosis by apigenin related flavonoids trough cytochrome c release and activation of caspase-9 and caspase-3 in leukemia HL-60 cells. Eur J Cancer 1999;35:1517–25.
40. Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M. Effect of citrus flavonoids on HL-60 cell differentiation. Anticancer Res 1999;19:1261-70.
Statistics
426 Views | 798 Downloads
How to Cite
Hussien, T. A., S. A. El-toumy, H. M. Hassan, and M. H. Hetta. “CYTOTOXIC AND ANTIOXIDANT ACTIVITIES OF SECONDARY METABOLITES FROM PULICARIA UNDULATA”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 8, no. 9, Sept. 2016, pp. 150-5, doi:10.22159/ijpps.2016v8i9.12814.
Section
Original Article(s)