Investigation of Chemical Composition, Antioxidant, Anticholinesterase and Anti-urease activities of Euphorbia helioscopia

Year 2018, Volume: 5 Issue: 3, 259 - 269, 15.09.2018

Ebru Deveci Gülsen Tel-çayan , Mehmet Emin Duru

https://doi.org/10.21448/ijsm.433681

Cited By: 4

Abstract

In this
study, chemical composition, antioxidant, anticholinesterase and anti-urease activities
of the essential oil, hexane, acetone, methanol and water extracts of Euphorbia helioscopia were investigated.
The chemical composition of the essential oil was analyzed by GC and GC/MS and β-cubebene (19.3 %), palmitic acid (12.2
%) and caryophyllene oxide (11.7 %) were identified as major compounds. The antioxidant
activity of essential oil and extracts was performed by several methods such as
β-carotene-linoleic acid, DPPH^•, ABTS^•+ radical scavenging,
CUPRAC and metal chelating assays. The water extract showed higher antioxidant activity
than BHA and α-tocopherol in β-carotene-linoleic acid, DPPH^•, ABTS^•+
and CUPRAC assays with IC₅₀: 1.08±0.39, 15.57±0.48, 1.89±0.33 and 12.50±0.11
μg/mL values, respectively. Also, the anticholinesterase and anti-urease activities
were tested against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and
urease enzymes, spectrophotometrically. The acetone extract (81.23±0.58 %) showed
very close BChE inhibitory activity to galantamine. The hexane extract (96.97±0.36
%) of E. helioscopia showed higher anti-urease
activity than thiourea (96.93±0.17 %) whereas the essential oil (91.37±0.26 %) indicated
very close anti-urease activity to the standard.

Keywords

Euphorbia helioscopia, Essential oil, Antioxidant activity, Anticholinesterase activity, Anti-urease activity

Investigation of Chemical Composition, Antioxidant, Anticholinesterase and Anti-urease activities of Euphorbia helioscopia

Abstract

In this study, chemical composition, antioxidant, anticholinesterase and anti-urease activities of the essential oil, hexane, acetone, methanol and water extracts of Euphorbia helioscopia were investigated. The chemical composition of the essential oil was analyzed by GC and GC/MS and β-cubebene (19.3 %), palmitic acid (12.2 %) and caryophyllene oxide (11.7 %) were identified as major compounds. The antioxidant activity of essential oil and extracts was performed by several methods such as β-carotene-linoleic acid, DPPH•, ABTS•+ radical scavenging, CUPRAC and metal chelating assays. The water extract showed higher antioxidant activity than BHA and α-tocopherol in β-carotene-linoleic acid, DPPH•, ABTS•+ and CUPRAC assays with IC50: 1.08±0.39, 15.57±0.48, 1.89±0.33 and 12.50±0.11 μg/mL values, respectively. Also, the anticholinesterase and anti-urease activities were tested against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and urease enzymes, spectrophotometrically. The acetone extract (81.23±0.58 %) showed very close BChE inhibitory activity to galantamine. The hexane extract (96.97±0.36 %) of E. helioscopia showed higher anti-urease activity than thiourea (96.93±0.17 %) whereas the essential oil (91.37±0.26 %) indicated very close anti-urease activity to the standard.

Keywords

Euphorbia helioscopia, Essential oil, Antioxidant activity, Anticholinesterase activity, Anti-urease activity

References

• [1] Uzair, M., Loothar, B.A. & Choudhary, B.A. (2009). Biological screening of Euphorbia helioscopia L. Pakistan Journal of Pharmaceutical Sciences. 22(2). 184-186.
• [2] Nazir, M., Ahmad, W. & Kreiser W. (1998). Isolation and NMR-assignments of 19αH-lupeol from E. helioscopia Linn (N.O. Euphorbiaceae). Pakistan Journal of Scientific and Industrial Research. 41. 6-10.
• [3] Zhang, W. & Guo Y.W. (2006). Chemical studies on the constituents of the Chinese medicinal herb Euphorbia helioscopia L. Chemical and Pharmaceutical Bulletin. 54(7). 1037-1039.
• [4] Kosemura, S., Shizuri, Y. & Yamamura, S. (1985). Isolation and structures of euphohelins, new toxic diterpenes from Euphorbia helioscopia. Bulletin of the Chemical Society of Japan. 58. 3112-3117.
• [5] Lee, S.H., Tanaka, T., Nonaka, G. & Nishioka I. (1991). Tannins and related-compounds .105. monomeric and dimeric hydrolyzable tannins having a dehydrohexahydroxydiphenoyl group, supinanin, euphorscopin, euphorhelin and jolkianin, from Euphorbia species. Chemical and Pharmaceutical Bulletin. 39. 630-638.
• [6] Lee, S.H., Tanaka, T., Nonaka, G. & Nishioka I. (1990). Tannins and related-compounds .95. isolation and characterization of helioscopinins and helioscopins, 4 new hydrolyzable tannins from Euphorbia helioscopia L. Chemical and Pharmaceutical Bulletin. 38. 1518-1523.
• [7] Park, K.H., Koh, D., Lee, S., Jung, I., Kim, K.H., Lee, C.H., Kim, K.H. & Lim Y. (2001). Anti-allergic and anti-asthmatic activity of helioscopinin-A, a polyphenol compound, isolated from Euphorbia helioscopia. Journal of Microbiology and Biotechnology. 11. 138-142.
• [8] Cummings, J.L. (2004). Alzheimer’s disease. The New England Journal of Medicine. 351. 56-67.
• [9] Tu, Y., Huang, J. & Li, Y. (2017). Anticholinesterase, antioxidant, and beta-amyloid aggregation inhibitory constituents from Cremastra appendiculata. Medicinal Chemistry Research. 27. 857-863.
• [10] Varadarajan, S., Yatin, S., Aksenova, M. & Butterfield, D.A. (2000). Alzheimer's amyloid β-peptide-associated free radical oxidative stress and neurotoxicity. Journal of Structural Biology. 130. 184-208.
• [11] Senol, F.S., Orhan, I., Yilmaz, G., Ciçek, M.& Sener, B. (2010). Acetylcholinesterase, butyrylcholinesterase, and tyrosinase inhibition studies and antioxidant activities of 33 Scutellaria L. taxa from Turkey. Food and Chemical Toxicology. 48. 781-788.
• [12] Adams, R.P. (2007). Identification of essential oil components by gas chromatography/quadrupole mass spectrometry. Journal of The American Society for Mass Spectrometry. 16. 1902-1903.
• [13] Tel. G., Apaydın. M., Duru. M.E. & Ozturk, M. (2012). Antioxidant and cholinesterase inhibition activities of three Tricholoma species with total phenolic and flavonoid contents: The edible mushrooms from Anatolia. Food Analytical Methods. 5. 495- 504.
• [14] Çayan, F., Tel, G., Duru, M.E., Öztürk, M., Türkoğlu, A. & Harmandar, M. (2014). Application of GC, GC-MSD, ICP-MS and spectrophotometric methods for the determination of chemical composition and in vitro bioactivities of Chroogomphus rutilus: The edible mushroom species. Food Analytical Methods. 7. 449-458.
• [15]. Slinkard K., Singleton V.L. (1977) Total phenol analyses: Automation and comparison with manual methods, American Journal of Enology and Viticulture, 28: 49-55.
• [16] Park, Y.K., Koo, M.H., Ikegaki, M. & Contado, J.L. (1997). Comparison of the flavonoid aglycone contents of Apis mellifera propolis from various regions of Brazil. Brazilian Archives of Biology and Technology. 40. 97-106.
• [17] Ellman, G.L., Courtney, K.D., Andres, V. & Featherston, R.M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology. 7. 88-95.
• [18] Weatherburn, M.W. (1967). Phenol-hypochlorite reaction for determination of ammonia. Analytical Chemistry. 3. 971-974.
• [19] Fokialakis, N., Melliou, E., Magiatis, P., Harvala, C. & Mitaku, S. (2003). Composition of the steam volatiles of six Euphorbia spp. from Greece. Flavour and Fragrance Journal. 18. 39-42.
• [20] Mateo, C., Calderón, J. & Sanz, J. (1988). Essential oils of some Sideritis species from central and southern Spain. Phytochemistry. 27. 151-153.
• [21] Bravo, L. (1988). Polyphenols: Chemistry, dietary sources, metabolismand nutritional significance. Nutrition Reviews. 56. 317-333.
• [22] Sen, S., De, B., Devanna, N. & Chakraborty, R. (2013). Total phenolic, total flavonoid content, and antioxidant capacity of the leaves of Meyna spinosa Roxb., an Indian medicinal plant. Chinese Journal of Natural Medicines. 11(2). 0149-0157.
• [23] Maoulainine, L.B.M., Jelassi, A., Hassen, I. & Boukhari, O.M.S.O.A. (2012). Antioxidant proprieties of methanolic and ethanolic extracts of Euphorbia helioscopia (L.) aerial parts. International Food Research Journal. 19(3). 1125-1130.
• [24] Zhang, D., Zheng, X.Y., Yan, X.W., Cao, W.G. & Wang, G. (2011). Determination of total flavonoids and rutin in Euphorbia helioscopia L. from Chongqing. Medicinal Plant. 2(7). 30-32.
• [25] Rauf. A., Qaisar. M., Uddin. G., Akhtar. S. & Muhammed. N. (2012). Antioxidant profile and phytochemical screening of E. helioscopia. Middle-East Journal of Medicinal Plants Research. 1(1). 19-23.
• [26] Saleem, U., Ahmad, B., Hussain, K., Ahmad, M., Bukhari, N.I. & Ishtiaq, S. (2014). Estimation of antioxidant power in various extracts of Euphorbia helioscopia L. with five different in vitro antioxidant models. Asian Journal of Chemistry. 26. 1241-1245.
• [27] Vinutha, B., Prashanth, D., Salmab, K., Sreeja, S.L., Pratiti, D., Padmaja, R., Radhika, S., Amit, A., Venkateshwarlu, K. & Deepak, M. (2007). Screening of selected Indian medicinal plants for acetylcholinesterase inhibitory activity. Journal of Ethnopharmacology. 109. 359-363.
• [28] Pisano, B., Cosentino, S., Viale, S., Spanò, D., Corona, A., Esposito, F., Tramontano, E., Montoro, P., Tuberoso, C.I.G., Medda, R. & Pintus, F. (2016). Biological activities of aerial parts extracts of Euphorbia characias. BioMed Research International. 2016. 11 pages.
• [29] Zengin, G., Uysal, A., Aktumsek, A., Mocan, A., Mollica, A., Locatelli, M., Custodio, L., Neng, N.R., Nogueira, J.M.F., Aumeeruddy-Elalfi, Z. & Mahomoodally, M.F. (2017). Euphorbia denticulata Lam.: A promising source of phyto-pharmaceuticals for the development of novel functional formulations. Biomedicine & Pharmacotherapy. 87. 27-36.
• [30] Gholamhoseinian, A., Moradali, M.N. & Sharifi-far F. (2009). Screening the methanol extracts of some Iranian plants for acetylcholinesterase inhibitory activity. Research in Pharmaceutical Sciences. 4(2). 105-112.
• [31] Ahmad, V.U., Hussain, J., Hussain, H., Jassbi, A.R., Ullah, F., Lodhi, M.A., Yasin, A. & Choudhary, M.I. (2003). First natural urease inhibitor from Euphorbia decipiens. Chemical and Pharmaceutical Bulletin. 51. 719-723.
• [32] Ahmad, V.U., Hussain, J., Hussain, H., Farooq, U., Ullah, F., Lodhi, M.A. & Choudhary, M.I. (2005). Two new diterpene polyesters from Euphorbia decipiens. Natural Product Research. 19. 267-274.
• [33] Lodhi, M.A., Hussain, J., Abbasi, M.A., Jassbi, R., Choudhary, M.I. & Ahmad, V.U. (2006). A new Bacillus pasteurii urease inhibitor from Euphorbia decipiens. Journal of Enzyme Inhibition and Medicinal Chemistry. 21(5). 531-535.
• [34] Minozzo, B.R., Leme, B.M., Justo, A.D.S., Lara, J.E., Petry, V.E.K., Fernandes, D., Belló, C., Vellosa, J.C.R., Campagnoli, E.B., Nunes, O.C., Kitagawa, R.R., Avula, B., Khan, I.A. & Beltrame, F.L. (2016). Anti-ulcer mechanisms of polyphenols extract of Euphorbia umbellata (Pax)Bruyns (Euphorbiaceae). Journal of Ethnopharmacology. 191. 29-40.