Abstract
Ethanolic and aqueous leaf extracts of Ficus cyathistipula significantly reduced blood-glucose level, improved triglycerides and cholesterol levels of dyslipidemia in diabetic-rats. They similarly reduced the inflammation of paw-edema and stomach-ulcers in rats. Fractions obtained by successive partition of ethanolic extract were assessed for their cytotoxicity, antioxidant and antimicrobial activities; Petroleum ether fraction was the most cytotoxic (IC50 = 4.43 ± 0.2, 17.3 ± 2.22 and 15.5 ± 3.67 μg/ml on MCF7, HepG2 and HeLa cell lines, respectively). Ethyl acetate fraction was the strongest antioxidant in DPPH assay (IC50 = 100 μg/ml). All samples exhibited low to strong antimicrobial activity. Chemical investigation of leaf extracts led to the isolation of α-amyrin palmitate (1), lupeol acetate (2), taraxerol (3), β-sitosterol (4), protocatechuic acid (5) and 3-O-caffeoyl quinic acid (6) that were identified via spectral and chromatographic analyses. Metabolite profiling was performed via UPLC-PDA-MS and revealed the presence of flavonoid glycosides, phenolic acids, isoflavones, coumarins and fatty acids. Quantitative determination revealed 593 ± 0.5 mg BSE, 348.1 ± 0.09 mg GAE, 238.7 ± 0.5 mg rutin and 9 ± 0.5 g tannins per 100 g d.wt. of leaves. GLC analysis of lipid fraction revealed identification of phytosterols (15.6%), saturated (51.71%) and unsaturated (41.9%) fatty acids. Galactose, glucose, arabinose and glucoronic acid (36.98%, 28.86%, 22.56% and 1.06%, respectively) were identified by HPLC analysis of mucilage-hydrolysate.
Acknowledgments:
The authors were grateful to Prof. Mohamed Farag for carrying out UPLC-MS analysis.
References
1. Phan VK, Nguyen XC, Nguyen XN, Vu KT, Ninh KB, Chau VM, et al. Antioxidant activity of a new C-glycosylflavone from the leaves of Ficus microcarpa. Bioorg Med Chem Lett 2011;21:633–37.10.1016/j.bmcl.2010.12.025Search in Google Scholar
2. Ramadan MA, Ahmed AS, Nafady AM, Mansour AI. Chemical composition of the stem barks and leaves of Ficus pandurata Hance. Nat Prod Res 2009;23:1218–30.10.1080/14786410902757899Search in Google Scholar
3. Sirisha N, Sreenivasulu M, Sangeeta K, Chetty CM. Antioxidant properties of Ficus species. Int J PharmTech Res 2010;2:2178–82.Search in Google Scholar
4. Chopra RN, Chopra IC, Handa RL, Kapin ID. Indigenous drugs of India. U.N. Calcutta: Dhur and Sons Private Ltd., 1950.Search in Google Scholar
5. Teixeira DM, Patao RF, Coelho AV, da Costa CT. Comparison between sample disruption methods and Solid–Liquid Extraction (SLE) to extract phenolic compounds from Ficus carica leaves. J Chromatogr A 2005;1103:22–8.10.1016/j.chroma.2005.11.047Search in Google Scholar
6. Wanjari M, Kumar P, Umathe SN. Anti-inflammatory effect of ethanolic extract of Ficus benghalensis Linn. in Carrageenan induced paw edema in rats. J Phcog 2011;3:96–9.10.5530/pj.2011.23.15Search in Google Scholar
7. Chandraker A, Saha R. Anti-inflammatory activity and pharmacognostical study of Ficus arnottiana (Miq) leaves extract. Int J Res Ayurveda Pharm 2011;2:1566–7.Search in Google Scholar
8. Ghazi F, Rahumat A, Yassin Z, Ramil NS, Buslima NA. Determination of total polyphenols and nuitritional composition of two different types of Ficus carica leaves cutivated in Saudi Arabia. Pak J Nutr 2012;11:1061–5.10.3923/pjn.2012.1061.1065Search in Google Scholar
9. Barwick M. Tropical & subtropical trees. Thames & Hudson Ltd: London, 2004.Search in Google Scholar
10. Huxely A. Dictionary of gardening. MacMillan Company: New York, 1992.Search in Google Scholar
11. El-Sakhawy FS, Kassem HA, El-Gayed SH, Abou-Hussein DR, Mostafa MM. Botanical and genetic characterization of Ficus cyathistipula Warb. Growing in Egypt, IJPSR 2015;6:1992–2004.Search in Google Scholar
12. El-Gayed SH. Pharmacognostical study of certain plants belonging to family Moraceae, Ph.D. Thesis, Faculty of Pharmacy, Cairo University, Cairo, 2000.Search in Google Scholar
13. Chrums SC, Stephen AM. The determination of molecular weight distribution of Maize Starch Dextrins by Gel Chromatography. J S Afr Chem Inst 1973;26:46–50.Search in Google Scholar
14. Andress JM. The mouse: toxicology, acute toxicity studies. In: Animal models in toxicology Gad SC, Chengelis CP, editors. New York: Marcel Dekker, 1992:193–5.Search in Google Scholar
15. Devi MN, Singh KB, Singh SR, Singh CB, Lukesh D, Amitabh D. Antihyperglycemic effect of aqueous and ethanol extract of aerial part of Osbeckia nepalensis Hook in alloxan-induced diabetic rats. Int J PharmTech Res 2012;4:233–44.Search in Google Scholar
16. Winter CC, Risely EA, Nuss GW. Carrageenan-induced edema in hind paw if the rats as an assay for anti-inflammatory drugs. Proc Soc Exp Biol Med 1962;111:544–7.10.3181/00379727-111-27849Search in Google Scholar
17. Mózsik G, Móron F, Jávor T. Cellular mechanisms of the development of gastric mucosal damage and of gastrocytoprotection induced by prostacyclin in rats. A Pharmacological Study. Prostagland Leukot Med 1982;9:71–84.10.1016/0262-1746(82)90074-9Search in Google Scholar
18. Zengil H, Onuk E, Ercan ZS, Turker RK. Protective effect of iloprost and UK 38485 against gastric mucosal damage induced by various stimuli. Prostagland Leukot Med 1987;30:61–7.10.1016/0262-1746(87)90135-1Search in Google Scholar
19. Skehan P, Storeng R, Scudiero D, Monks A, McMahom JM, Vistica D, et al. New colorimetric cytotoxicity assay for anticancer drug screening. J Natl Cancer Inst 1990;82:1107–12.10.1093/jnci/82.13.1107Search in Google Scholar
20. Holder IA, Boyce ST. Agar well diffusion assay testing of bacterial susceptibility to various antimicrobials in concentrations non-toxic for human cells in culture. Burns 1994;20:426–9.10.1016/0305-4179(94)90035-3Search in Google Scholar
21. Doughari JH. Antimicrobial activity of Tamarindus indica Linn. Trop J Pharm Res 2006;5:597–603.10.4314/tjpr.v5i2.14637Search in Google Scholar
22. Romano CS, Abadi K, Repetto V, Vojnov AA, Moreno S. Synergistic antioxidant and antibacterial activity of rosemary plus butylated derivatives. Food Chem 2009;115:456–61.10.1016/j.foodchem.2008.12.029Search in Google Scholar
23. Stahl E. Thin layer chromatography, 2nd ed. Springer Verlag: New York, 1969.10.1007/978-3-642-88488-7Search in Google Scholar
24. Markham KR. Techniques of flavonoid identification. Academic Press: London, 1982.Search in Google Scholar
25. Wagner H, Baldt S, Zagainiski EM. Droger analyse. Springer-Verlag: Berlin, 1983.Search in Google Scholar
26. Farag MA, Abdelfattah MS, Badr SE, Wessjohann LA. Profiling the chemical content of Ficus lyrata extracts via UPLC-PDA-qTOF-MS and chemometrics. Nat Prod Res 2014;28:1549–56.10.1080/14786419.2014.926353Search in Google Scholar PubMed
27. Sanchez-Mata MC, Camara-Hurtado M, Diez-Marques C. Identification and quantificatIon of soluble sugars in green beans by HPLC. Eur Food Res Technol 2002;214:254–8.10.1007/s00217-001-0447-0Search in Google Scholar
28. Vogel AI. A text book of practical organic chemistry, 3rd ed. Longmans and Green Co. Ltd: London, 1975.Search in Google Scholar
29. Wen J, Kang L, Liu H, Xiao Y, Zhang X, Chen Y. A validated UV-HPLC method for determination of chlorogenic acid in Lepidogrammitis drymoglossoides (Baker) Ching, Polypodiaceae. Pharmacognosy Res 2012;4:148–53.10.4103/0974-8490.99076Search in Google Scholar PubMed PubMed Central
30. Finar IL. Organic chemistry, 6th ed. Longman group Ltd: England, 1973.Search in Google Scholar
31. Daksha A, Jaywant P, Bhagyashree C, Subodh P. Estimation of sterols content in edible oil and ghee samples. Int J Pharm Sci Rev Res 2010;5:135–7.Search in Google Scholar
32. Druckerei CH. European Pharmacopoeia, 4th ed. Beck, Nördlingen: Germany, 2002.Search in Google Scholar
33. Geissman TA. The chemistry of flavonoid compounds. The Macmillan Company: New York, 1962.Search in Google Scholar
34. European Pharmacopeia, Brand I-III, Frankfurt/M: Deutscher, Apotheker, Verlag, Stuttgart, Govi Verlag, Gmbh, 1978.Search in Google Scholar
35. Biswas M, Biswas K, Ghosh AK, Haldar PK. A pentacyclic triterpenoid possessing anti-inflammatory activity from the fruits of Dregea volubilis. Phcog Mag 2009;5:64–8.10.3742/OPEM.2009.9.4.315Search in Google Scholar
36. Jamal AK, Yaacob WA, Din LB. A chemical study on Phyllanthrus reticulatus. J Phys Sci 2008;19:45–50.Search in Google Scholar
37. Rasoanaivo LH, Wadouachi A, Andriamampianina TT, Andriamalala SG, Razafindrakoto EJ, Raharisololalao A, et al. Triterpenes and steroids from the stem bark of Gambeya boiviniana Pierr. J Pharmacogn Phytochem 2014;3:68–72.Search in Google Scholar
38. Yu Y, Gao H, Tang Z, Song X, Wu L. Several phenolic acids from the fruit of Capparis spinosa. Asian J Tradit Med 2006;1:3–4.Search in Google Scholar
39. Ragasa CY, Tsai PW, Shen CC. Terpenoids and sterols from the endemic and endangered Philippine trees, Ficus pseudopalma and Ficus ulmifolia. Philipp J Sci 2009;138:205–9.Search in Google Scholar
40. Ao C, Higa T, Ming H, Ding YT, Tawata S. Isolation and identification of antioxidant and hyaluronidase inhibitory compounds from Ficus microcarpa L. fil. Bark. J Enzyme Inhib Med Chem 2010;25:406–13.10.3109/14756360903213473Search in Google Scholar PubMed
41. El-Hawary SS, Wassel GM, El-Menshawi BS, Ibrahim NA, Mahmoud K, Ayoub MM. Antitumor and antioxidant of Ficus elastica and Ficus benghalensis Linn. Family Moraceae. World Appl Sci J 2012;19:1532–9.Search in Google Scholar
42. Somwong P, Suttisri R, Buakeaw A. New sesquiterpenes and phenolic compound from Ficus foveolata. Fitoterapia 2013;85:1–7.10.1016/j.fitote.2012.12.026Search in Google Scholar PubMed
43. Veberic R, Colaric M, Stampar F. Phenolic acids and flavonoids of fig fruit (Ficus carica L.) in the Northern mediterranean region. Food Chem 2008;10:153–7.10.1016/j.foodchem.2007.05.061Search in Google Scholar
44. Park C, Moon D, Choi BT, Lee WH, Kim G, Choi YH. β-sitosterol induces anti-proliferation and apoptosis in human leukemic U937 cells through activation of caspase-3 and induction of Bax/Bcl-2 ratio. Bio Pharm Bull 2007;30:1317–23.10.1248/bpb.30.1317Search in Google Scholar PubMed
45. Rabie A. Bioactivity of extracts and components of Pteleopsismyrtifolia, Ph.D. thesis Pharmacology, University of Pretoria: Pretoria, 2005.Search in Google Scholar
46. Yousef MF, Eid HH, Ezzat SM. Cytotoxic sterol and triterpenes from Ficus binnendijkii (Miq.) Cultivated in Egypt. Egypt J Biomed Sci 2009;29:241–8.Search in Google Scholar
47. Abou-El Wafa GSE, Shaaban M, Shaaban KA, El-Naggar MEE, Laatsch H. Three new unsaturated fatty acids from marine green alga Ulva fasciata Delile. Z Naturforsch 2009;64b:1199–207.10.1515/znb-2009-1014Search in Google Scholar
48. Li SS, Jiang ZM, Thamm L, Zhou GT. 10-hydroxy-2-decenoic acid as an antimicrobial agent in draft keg-conditioned wheat beer. J Am Soc Brew Chem 2010;68:114–8.10.1094/ASBCJ-2010-0303-01Search in Google Scholar
49. Martin-Arjol I, Bassas-Galia M, Bermudo E, Garcia F, Manresa A. Identification of oxylipins with antifungal activity by LC-MS/MS from the supernatant of Pseudomonas 42A2. Chem Phys Lipids 2010;163:341–6.10.1016/j.chemphyslip.2010.02.003Search in Google Scholar PubMed
Supplemental Material:
The online version of this article (DOI: 10.1515/znc-2015-0274) offers supplementary material, available to authorized users.
©2016 by De Gruyter
Articles in the same Issue
- Frontmatter
- Editorial
- ZNC opens a new chapter focussing on the emerging field of natural and natural-like compounds
- Research Articles
- Design, synthesis and evaluation of antitumor activity of new rotundic acid acylhydrazone derivatives
- Synthesis and in vitro anti-HIV-1 activity of a series of N-arylsulfonyl-3-propionylindoles
- Jaspiferin G, a new isomalabaricane-type triterpenoid from the sponge Jaspis stellifera
- The effect of coniine on presynaptic nicotinic receptors
- Nematicidal effect of plumbagin on Caenorhabditis elegans: a model for testing a nematicidal drug
- Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil
- Phytochemical investigation of the bioactive extracts of the leaves of Ficus cyathistipula Warb.
- Chemical composition and biological activity of the essential oil from Thymus lanceolatus
- Ascidian bioresources: common and variant chemical compositions and exploitation strategy – examples of Halocynthia roretzi, Styela plicata, Ascidia sp. and Ciona intestinalis
- Structural and evolutionary relationships among RuBisCOs inferred from their large and small subunits
Articles in the same Issue
- Frontmatter
- Editorial
- ZNC opens a new chapter focussing on the emerging field of natural and natural-like compounds
- Research Articles
- Design, synthesis and evaluation of antitumor activity of new rotundic acid acylhydrazone derivatives
- Synthesis and in vitro anti-HIV-1 activity of a series of N-arylsulfonyl-3-propionylindoles
- Jaspiferin G, a new isomalabaricane-type triterpenoid from the sponge Jaspis stellifera
- The effect of coniine on presynaptic nicotinic receptors
- Nematicidal effect of plumbagin on Caenorhabditis elegans: a model for testing a nematicidal drug
- Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil
- Phytochemical investigation of the bioactive extracts of the leaves of Ficus cyathistipula Warb.
- Chemical composition and biological activity of the essential oil from Thymus lanceolatus
- Ascidian bioresources: common and variant chemical compositions and exploitation strategy – examples of Halocynthia roretzi, Styela plicata, Ascidia sp. and Ciona intestinalis
- Structural and evolutionary relationships among RuBisCOs inferred from their large and small subunits