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Isolation and characterization of polyphenols from Euphorbia heterophylla L. (Euphorbiaceae) leaves

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Many of Euphorbiaceae species are recognized as traditional medicinal plants and the oils and latex of many species have also economic importance. In fact, Euphorbia heterophylla L., belonging to this family and popularly known in Brazil as “leiteira”, “flor-de-poetas” and wild poinsettia, has been used traditionally in Africa and India to treat many kinds of health disorders. However, the chemical composition of this species has been little studied so far. In the present investigation, the flavonoids quercitrin (quercetin 3-O-α-L-rhamnopyranoside), hyperin (quercetin 3-O-β-D-galactopyranoside), isoquercitrin (quercetin 3-O-β-D-glucopyranoside) and isoquercitrin 6”-malonate (quercetin 3-O-β-D-(6”-malonate)-glucopyranoside) were isolated from an ethyl acetate partition of aqueous ketone extract from E. heterophylla leaves. The dehydroellagitannins geraniin and phyllantusiin D as well as 1,2,3,4,6- penta-O-galloyl- β-D-glucopyranoside, caffeic acid  and the coumarin aesculetin (6,7-dihydroxycoumarin) were also isolated. All the compounds were characterized by spectroscopic methods such as 1H and 13C-NMR, COSY, HETCOR, APT and by comparison with literature data. The presence of these substances of relevant bioactivity is reported for the first time in E. heterophylla through our study supporting in this way the medicinal use of this specie.

DOI
10.17648/2446-4775.2019.696
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Referências do artigo
The Plant List. Version 1.1. Published on the Internet. Access on: Feb 23, 2019. [Link]. Cruz GL. Dicionário das Plantas Úteis do Brasil. 5th ed. Rio de Janeiro: Bertrand Brasil; 1995. ISBN: 9788528602609. Babili FE, Moulis C, Bon M, Respaud M-J, Fourasté I. Three furano-diterpenes from the bark of Croton campestris. Phytochemistry. 1998; 48(1):165-169. ISSN: 0031-9422. [CrossRef]. Rizzini CT, Mors WB. Botânica Econômica Brasileira. 2nd ed. Rio de Janeiro: Âmbito Cultural; 1995. ISBN: 9788586742187. Hawash SI, Abdel Kader E, El Diwani G. Biodiesel production from Jatropha seeds using heterogeneous integrated extraction reaction process. Afinidad. 2015; 72:150-154. ISSN: 2339-9686. [Link]. Kumar S, Malhotra R, Kumar D. Euphorbia hirta: Its chemistry, traditional and medicinal uses, and pharmacological activities. Pharmacog Rev. 2010; 4(7):58-61. ISSN: 0976-2787. [CrossRef][PubMed]. Wilson AK. Euphorbia heterophylla: A review of distribution, importance and control. Trop Pest Manag 1981; 27(1):32-38. ISSN: 1366-5863. [CrossRef]. Lorenzi H. Manual de Identificação e Controle de Plantas Daninhas: Plantio Direto e Convencional. 4ª ed. Nova Odessa: Plantarum. 1994. ISBN: 9788586714450. Nalule AS, Mbaria JM, Kimenju W. In vitro anthelmintic potential and phytochemical composition of ethanolic and water crude extracts of Euphorbia heterophylla Linn. J Med Plants Res. 2013; 7(43):3202-3210. ISSN: 1996-0875. [CrossRef][Link]. El-Emary NA, Makboul MA, Abdel-Hafiz MA, Farag SF. Phytochemical study of Euphorbia heterophylla L. cultivated in Egypt. B Pharm Sci, Assiut Univ. 1990; 13:51-58. ISSN: 1110-0052. Tiwari KP, Kumar P, Minocha PK, Massod M. Chemical constituents of Euphorbia heterophylla Linn. and Euphorbia parviflora. Proc Natl Acad Sci, India, Sect. A Phys Sci. 1981; 51:213-214. ISSN: 0369-8203. Wagner H, Bladt S. Plant Drug Analysis: A Thin Layer Chromatography Analysis Atlas. 2nd ed. New York: Springer-Verlag; 1991. ISBN: 0-387-13195-7. Yoshida T, Itoh H, Matsunaga S, Tanaka R, Okuda T. Tannins and related polyphenols of euphorbiaceous plants. IX. Hydrolyzable tannins with 1C4 glucose core from Phyllanthus flexuosus Muell. Arg. Chem Pharm Bull. 1992; 40(1):53-60. ISSN: 0009-2363. [CrossRef][Link]. Bate-Smith EC. Detection and determination of ellagitannins. Phytochemistry. 1972; 11(3):1153-1156. ISSN: 0031-9422. [CrossRef]. Budavari S, O’Neil MJ, Smith A, Heckelman PE, Kinneary, JF. The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals. 12th ed. New Jersey: Merck & Co; 1996. ISBN: 0911910-12-3. Yoshida T, Namba O, Chen L, Liu Y, Okuda T. Ellagitannins monomers and oligomers from Euphorbia prostrata Ait. and oligomers from Loropetalum chinense Oliv. Chem Pharm Bull. 1990; 38(12):3296-3302. ISSN: 0009-2363. [CrossRef][Link]. Markham KR, Chari VM, Mabry TJ. Carbon-13 NMR Spectroscopy of Flavonoids. In: Harborne, JB, Mabry, TJ, editors. The flavonoids - Advances in Research. Authors, London: Chapman & Hall; 1982. Chapter Two. p. 19-134. ISBN-13:978-0-412-22480-5. Agrawal PK. Carbon-13 NMR of Flavonoids. In: Studies in Inorganic Chemistry. 1st ed. Vol. 39. Amsterdam: Elsevier Science; 1989. ISBN: 9781483290744. Almeida AP, Miranda MMFS, Simoni IC, Wigg MD, Lagrota MHC, Costa SS. Flavonol monoglycosides isolated from the antiviral fractions of Persea americana (Lauraceae) leaf infusion. Phytother Res. 1998; 12(8):562-567. ISSN: 0951-418X. [CrossRef] Prasain JK, Barnes S. Uptake and Metabolism of Dietary Proanthocyanidins. In: Watson RR, Preedy VR, Zibadi S, editors. Polyphenols in human health and disease. San Diego: Academic Press. 2013. Chapter 41. p. 553-560. ISBN: 9780123984678. Seleen D, Pardi V, Murata RM. Review of flavonoids: A diverse group of natural compounds with anti-Candida albicans activity in vitro. Arch Oral Biol. 2017; 76:76-83. ISSN: 0003-9969. [CrossRef][PubMed]. Hahn R, Nahrstedt A. Hydroxycinnamic acid derivatives, caffeoylmalic and caffeoylaldonic acid esters, from Chelidonium majus. Planta Med. 1993; 59(1):71-75. ISSN: 0032-0943. [CrossRef] [PubMed]. Steck W, Mazurek M. Identification of natural coumarins by NMR spectroscopy. Lloydia. 1972; 35(4):418-439. ISSN: 0163-3864. [PubMed]. Magnani C, Isaac VLB, Correa MA, Salgado HRN. Caffeic acid: A review of its potential use in medications and cosmetics. Anal Methods. 2014; 6:3203-3210. ISSN: 1759-9679. [CrossRef]. Liang C, Ju W, Pei S, Tang Y, Xiao Y. Pharmacological activities and synthesis of esculetin and its derivatives: A mini-review. Molecules. 2017; 22(3):387. ISSN: 1420-3049. [CrossRef][PubMed]. Tanaka T, Nonaka G-I, Nishioka I. Punicafolin, an ellagitannin from the leaves of Punica granatum. Phytochemistry. 1985; 24(9): 2075-2078. ISSN: 0031-9422. [CrossRef]. Berlinck RGS, Okuda T, Yoshida T, Hatano T. Hydrolyzable Tannins and Related Polyphenols. In: Herz W, Kirby W, Moore RE, Steglich W, Tamm C, editors. Progress in the Chemistry of Organic Natural Products. New York: Spring-Verlag; 1995. Vol. 66, p.1-117. ISBN: 978-3-7091-9363-1. [CrossRef]. Londhe JS, Devasagayam TPA, Foo LY, Shastry P, Ghaskadbi SS. Geraniin and amariin, ellagitannins from Phyllanthus amarus, protect liver cells against ethanol induced cytotoxicity. Fitoterapia. 2012; 83(8):1562-1568. ISSN: 0367-326X. [CrossRef][PubMed]. Perera A, Ton SH, Palanisamy D. Perspectives on geraniin, a multifunctional natural bioactive compound. Trends Food Sci Technol. 2015; 44(2):243-257. ISSN: 0924-2244. [CrossRef] Foo LY, Wong H. Phyllantusiin D, an unusual hydrolysable tannin from Phyllantus amarus. Phytochemistry. 1992; 31(2):711-713. ISSN: 0031-9422. [CrossRef]. Londhe JS, Devasagayam TPA, Foo LY, Ghaskadbi SS. Antioxidant activity of some polyphenol constituents of the medicinal plant Phyllantus amarus Linn. Redox Rep. 2008; 13(5):199-207. ISSN: 1351-0002. [CrossRef][PubMed]. Zhang J, Li L, Kim S-H, Hagerman AE, Lü J. Anti-cancer, anti-diabetic and other pharmacologic and biological activities of penta-galloyl-glucose. Pharm Res. 2009; 26(9):2066-2080. ISSN: 0724-8741. [CrossRef][PubMed]. Sancheti S, Sancheti S, Um B-H, Seo S-Y. 1,2,3,4,6-penta-O-galloyl-β-D-glucose: A cholinesterase inhibitor from Terminalia chebula. S Afr J Bot. 2010; 76(2):285-288. ISSN: 0254-6299. [CrossRef] Santos RT, Hiramoto LL, Lago JHG, Sartorelli P, Tempone AG, Pinto EG, Lorenzi H. Anti-trypanosomal activity of 1,2,3,4,6-penta-O-galloyl-β-D-glucose isolated from Plectranthus barbatus Andrews (Lamiaceae). Quim Nova. 2012; 35(11):2229-2232. ISSN: 1678-7064. [CrossRef].
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