PHYTOCHEMICAL INVESTIGATION OF CHENOPODIUM MURALE (FAMILY: CHENOPODIACEAE) CULTIVATED IN IRAQ, ISOLATION AND IDENTIFICATION OF SCOPOLETIN AND GALLIC ACID

Omer H Ahmed; Maha N Hamad; Noor S Jaafar

doi:10.22159/ajpcr.2017.v10i11.20504

Authors

Omer H Ahmed Department of Pharmacognosy and Medicinal Plants, College of Pharmacy, University of Tikrit, Tikrit, Iraq.
Maha N Hamad Department of Pharmacognosy and Medicinal Plants, College of Pharmacy, University of Baghdad, Baghdad, Iraq.
Noor S Jaafar Department of Pharmacognosy and Medicinal Plants, College of Pharmacy, University of Baghdad, Baghdad, Iraq.

DOI:

https://doi.org/10.22159/ajpcr.2017.v10i11.20504

Keywords:

Chenopodium murale, Coumarins, Phenolic acid, High-performance liquid chromatography, High-performance thin-layer chromatography

Abstract

Â

Â Objective: The aim of our study was to investigate chemical constituents of leaves of Chenopodium murale since no phytochemical investigation had been done previously in Iraq.

Methods: Leaves of C. murale were macerated in absolute methanol for 2 days and fractionated by petroleum ether, chloroform, ethyl acetate, and n-butanol. The ethyl acetate fraction was analyzed by high-performance liquid chromatography (HPLC) and high-performance thin-layer chromatography (HPTLC) for its phenolic acid and coumarins contents. Coumarin derivative and phenolic acid were isolated from this fraction and identified by gas chromatography/mass spectrometry, infrared, ultraviolet, HPLC, and HPTLC.

Results: The different chromatographic and spectroscopic results revealed the presence of gallic acid and coumarin.

Conclusion: The results of the current study showed the presence of scopoletin and gallic acid in the ethyl acetate fraction of C. murale.

Downloads

Download data is not yet available.

References

Fuentes-Bazan S, Uotila P, Borsch T. A novel phylogeny-based generic classification for Chenopodium sensu lato, and a tribal rearrangement of Chenopodioideae (Chenopodiaceae). Willdenowia 2012;1(42):14.

KÃ¼tz. BSBI List 2007. Botanical Society of Britain and Ireland. The Original (xls) on 2015-01-25. [Last retrieved on 2014 Oct 17].

Chenopodiastrum murale. Germplasm Resources Information Network (GRIN). Agricultural Research Service (ARS), United States Department of Agriculture (USDA). [Last retrieved 2013 Jul 09].

Marie CN. Gardens of Hawaii. Honolulu, HI, USA: Bishop Museum Press; 1965. p. 331.

Boulos L. Medicinal Plants of North Africa. Algonac, MI: Reference Publications; 1983. p. 103.

Watt JM, Breyer-Brandwijk MG. The Medicinal and Poisonous Plants of Southern and Eastern Africa. 2nd ed. London, UK: E and S Lining Stone Ltd.; 1962. p. 1457.

Vasishita PC. Taxonomy of Angiosperms. India: Ram Chand; 1989. p. 648.

Gohar AA, Maatooq GT, Niwa M. Two flavonoid glycosides from Chenopodium murale. Phytochemistry 2000;53(2):299-303.

Lozoya J, Lozoya M. Flora Medicinal de Mexico, Primera Part: Plantas in Digenas. Mexico: Instituto Mexicano del Seguro Social; 1982. p. 31.

Rustenbekova GB, Goryaev MI, Nizhinskaya GA. Flavonoids of Chenopodium botrys. Khim Prir Soedin Tashk 1994;3:406.

De Pascual TJ, Torres C, Gonzalez MS, Grande M, Bellido IS. Delta-5-hydro-1-hydroxy carvomenthols from the essential oil of Chenopodium multifidum. Phytochemistry 1983;22:2749-52.

Bahrman N, Jay M, Gorenflot R. Contribution to the chemosystematic knowledge of some species of genus Chenopodium. Lett Bot 1985;2:107-13.

Ahmad AG, Maatooq GT, Niwa M. Two flavonoid glycosides from Chenopodium murale. Phytochemistry 2000;53:299-303.

El-Sayed NH, Awaad AS, Hifnawy MS, Mabry TJ. A flavonol triglycoside from Chenopodium murale. Phytochemistry 1999;51:591-3.

van Rompuy L, Zeevaart J. Are steroidal oestrogens natural plants constituents. Phytochemistry 1979;18:863-6.

Bathory M, Toth I, Szendrei K, Reisch J. Ecdysteroids in Spinacia oleraceae and Chenopodium bonus. Phytochemistry 1982;21:236-8.

Rizk AM. Constituents of plants growing in Qatar. Fitoterapia 1986;57:3-9.

Rizk AM. The Photochemistry of Flora of Qatar. London: King Print of Richmond; 1986. p. 30-2.

Aritomi M, Kawasaki T. Photochemistry. In: Boulos L, editor. Medicinal Plants of North Africa. Vol. 23. Algonac, MI: Reference Publications Inc.; 1984. p. 2043.

Zhao Y, Liu F, Lou HX. Studies on the chemical constituents of Solanum nigrum. Zhong Yao Cai 2010;33(4):555-6.

Ouzir M, El-Bairi K, Amzazi S. Toxicological properties of fenugreek (Trigonella foenum graecum). Food Chem Toxicol Int J Publ Br Ind Biol Res Assoc 2016;96:145-54.

Ma J, Jones SH, Hecht SM. A coumarin from Mallotus resinosus that mediates DNA cleavage. J Nat Prod 2004;67(9):1614-6.

Corbett JT. The scopoletin assay for hydrogen peroxide. A review and a better method. J Biochem Biophys Methods 1989;18(4):297-307.

Shaw CY, Chen CH, Hsu CC, Chen CC, Tsai YC. Antioxidant properties of scopoletin isolated from Sinomonium acutum. Phytother Res 2003;17(7):823-5.

Ojewole JA, Adesina SK. Mechanism of the hypotensive effect of scopoletin isolated from the fruit of Tetrapleura tetraptera. Planta Med 1983;49(1):46-50.

Capra JC, Cunha MP, Machado DG, Zomkowski AD, Mendes BG, Santos AR, et al. Antidepressant-like effect of scopoletin, a coumarin isolated from Polygala sabulosa (Polygalaceae) in mice: Evidence for the involvement of monoaminergic systems. Eur J Pharmacol 2010;7:232-8.

Carpinella MC, Ferrayoli CG, Palacios SM. Antifungal synergistic effect of scopoletin, a hydroxycoumarin isolated from Melia azedarach L. Fruits. J Agric Food Chem 2005;8:2922-7.

Cheng AS, Cheng YH, Chang TL. Scopoletin attenuates allergy by inhibiting Th2 cytokines production in EL-4 T cells. Food Funct 2012;3(8):886-90.

Pan R, Dai Y, Gao X, Xia Y. Inhibition of vascular endothelial growth factor-induced angiogenesis by scopoletin through interrupting the auto phosphorylation of VEGF receptor 2 and its downstream signaling pathways. Vasc Pharmacol 2011;54:18-28.

Tanaka Y, Data ES, Hirose S, Taniguchi T, Uritani I. Biochemical changes in secondary metabolites in wounded and deteriorated cassava roots. Agric Biol Chem 1983;47:603-700.

Uritani I. Biochemistry on postharvest metabolism and eterioration of some tropical tuberous crops. Bot Bull Acad Sin 1999;40:177-83.

Buschmann H, Rodriguez MX, Thome J, Beeching J. Accumulation of hydroxycoumarins during post-harvest deterioration of tuberous roots of cassava (Manihot esculenta Crantz). Ann Bot 2000;86:1153-60.

Giesemann A, Biehl B, Lieberei R. Identification of scopoletin as a phytoalexin of the rubber tree Hevea brasiliensis. J Phytopathol 2008;117:373-6.

Liu XL, Zhang L, Fu XL, Chen K, Qian BC. Effect of scopoletin on PC3 cell proliferation and apoptosis. Acta Pharmacol Sin 2001;22(10):929-33.

Manuele MG, Ferraro G, Barreiro Arcos ML, LÃ³pez P, Cremaschi G, Anesini C. Comparative immunomodulatory effect of scopoletin on tumoral and normal lymphocytes. Life Sci 2006;79(21):2043-8.

Panda S, Kar A. Evaluation of the ant thyroid, ant oxidative and ant hyperglycemic activity of scopoletin from Aegle marmelos leaves in hyperthyroid rats. Phytother Res 2006;20(12):1103-5.

Obasi SC, Njoku OU, Obidoa O. Effects of single oral doses of scopoletin and aflatoxin B1 on the clotting time, serum cholesterol and phospholipid levels of chicks. Indian J Physiol Pharmacol 1994;38(2):89-94.

Wirasutisna KR, Prabowo WC, Insanu M. Isolation and characterization of 3-acetyl aleuritolic acid and scopoletin from stem bark of Aleurites moluccana (L.) Willd. Int J Pharm Pharm Sci 2013;5(7):851-3.

Sampath M. Isolation and identification of gallic acid from Polyalthia longifolia (Sonn.) Thawaites. Int J Pharm Bio Sci 2013;4(2):966-72.

Kumari S. Evaluation of phytochemical analysis and antioxidant and antifungal activity of Pithecellobium dulce leavesâ€™ extract. Asian J Pharm Pharm Sci 2017;1(10):370-5.

Bhatt MK, Dholwani KK, Saluja A. Isolation and structure elucidation of scopoletin from Ipomoea reniformis (Convolvulaceae). J Appl Pharm Sci 2011;1(5):138-44.

Abri A, Maleki M. Isolation and identification of gallic acid from the Elaeagnus angustifolia leaves and determination of total phenolic, flavonoids contents and investigation of antioxidant activity. Iran Chem Commun 2016;41:46-154.

Chanwitheesuk A, Teerawutgulrag A, Kilburn JD, Nuansri R. Antimicrobial Gallic acid from Caesalpinia mimosoides Lamk. Food Chem 2005;100(3):1044-8.

Chen H, Walsh CT. Synthesis of novel N-substituted-2-oxo-2H- 1-coumarin-3-carboxamide and evaluated for selective anti helicobacter pylori activity and cytotoxicity. Chem Biol 2001;8:288-301.

Jain PK, Himanshu J. Coumarin: Chemical and pharmacological profile. J Appl Pharm Sci 2012;2(6):236-40.