Two new antioxidant anthraquinones namely Obtusifolate A and B from Rumex obtusifolius
Paper Details
Two new antioxidant anthraquinones namely Obtusifolate A and B from Rumex obtusifolius
Abstract
According to folk medicine Rumex obtusifolius ’s root has a prominent detoxifying result on the liver and is used against fever, jaundice, and as an anti-anemic tonic. The roots are laxative and the leaves of this Rumex are used against hepatic, dermatological and eye problems. The diverse medicinal applications of R. obtusifolius and its genus have prompted us to investigate the constituents of the said plant. In bio-guided isolation Two new anthraquinones namely sec-butyl 1, 8-dihydroxy-5-methyl-3-(4′-(5”methylbut-4”-enoyl)-2′-(2”oxopropyl)-6-tert-pentyl-anthraquinone-2-carboxylate (Obtusifolate A) and methyl 1, 8-dihydroxy-5-methyl-3-(2’methyl-4′-(2”methylbut-1”-enoyl)-6-tert-pentyl-anthraquinone-2-carboxylate (Obtusifolate B) were isolated from Rumex obtusifolius. Their structures were identified by chemical and modern spectroscopic techniques i.e. 1H and 13C NMR, UV, IR and mass spectrometry. Both the compounds showed excellent antioxidant activities in the DPPH radical scavenging assay. Our findings provide evidence that R. obtusifolius is a potent source of natural antioxidants, and thus justified its uses in folkloric medicines.
Agarwal SK, Singh SS, Verma S, Kumar S. 2000. Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of ethnopharmacology 72(1), 43-46. http://dx.doi,org/10.1016/S0378-8741(00)00195 -1
Demirezer LÖ, Kuruüzüm A. 1997. A comparative chemotaxonomic study on eleven Rumex species growing in Turkey. FABAD Journal of Pharmaceutical Sciences 22, 153-158. http://dx.doi.org/10.1016/S0031-9422(00)9419-3
Demirezer Ö, Kuruüzüm A, Bergere I, Schiewe HJ, Zeeck A. 2001. Five naphthalene glycosides from the roots of Rumex patientia. Phytochemistry 56(4), 399-402. http://dx.doi.org/10.1016/S0031-9422(00)00368-X
Demirezer LÖ, Kuruüzüm-Uz A, Bergere I, Schiewe HJ, Zeeck A. 2001. The structures of antioxidant and cytotoxic agents from natural source: anthraquinones and tannins from roots of Rumex patientia. Phytochemistry 58(8), 1213-1217. http://dx.doi.org/ 10.1016/ S0031-9422(01)00337-5
Fassil Y, Bezabeh A, Abegaz B, Botta B, Monache GD, Monache FD. 1985. Anthracene derivatives from Rumex abyssinicus. Journal of Natural Products 48(1), 148-148. http://dx.doi.org/10.1021/np50037a034
Gautam R, Karkhile KV, Bhutani KK, Jachak SM. 2010. Anti-inflammatory ,cyclooxygenase (COX)-2, COX-1 inhibitory and free radical scavenging effects of Rumex nepalensis Spreng. Planta medica. http://dx.doi.org/10.1055/s-0030-1249779.
Girault L. 1984.Kallawaya, guérisseurs itinerants des Andes: recherches sur les pratiques médicinales et magiques (No.107).IRD Editions.
Harborne JB, Mokhtari N. 1977. Two sulphated anthraquinone derivatives in Rumex pulcher. Phytochemistry 16(8), 1314-1315.
Harding WW, Henry GE, Lewis PA, Jacobs H, McLean S, Reynolds WF. 1999. Alvaradoins A− D. Anthracenone C Arabinosides from Alvaradoa jamaicensis. Journal of natural products 62(1), 98-101. http://dx.doi.org/10.1021/np980300i
Hasan A, Ahmed I, Jay M, Voirin B. 1995. Flavonoid glycosides & an anthraquinone from Rumex chalepensis. Phytochemistry 39(5), 1211-1213 http://dx.doi.org/10.1016/0031-9422(95) 00071-E
Haslett BG, Bailey CJ, Ramshaw JA, Scawen, MD, Boulter D. 1978. The amino acid sequence of plastocyanin from Rumex obtusifolius. Phytochemistry 17(4), 615-617. http://dx.doi.org/10.1016/S0031-9422(00)94194-3
Ibáñez-Calero SL, Jullian V, Sauvain M. 2009.A new anthraquinone isolated from Rumex obtusifolius. Revista Boliviana de Química 26(2), 49-56.
Iizuka A, Iijima OT, Kondo K, Itakura H, Yoshie F, Miyamoto H, Matsumiya T. 2004. Evaluation of Rhubarb using antioxidative activity as an index of pharmacological usefulness. Journal of ethnopharmacology 91(1), 89-94. http://dx.doi.org/10.1016/j.jep.2003.11.021
Kasai T, Okuda M, Sakamura S. 1981.6-O-Malon- yl-β-methyl-D-glucopyranoside from roots of Rumex obtusifolius. Phytochemistry 20(5), 1131-1132. http://dx.doi.org/10.1016/0031-9422(81) 83043 -9
Khabir A, Khan F, Afzal M, Haq ZU, Ullah M. A, Shah AMH, Khan S. 2017. Antimicrobial Efficacy and Cytotoxic Screening of Dichloromethane Sub-fractions of Rumex obtusifolius. Asian Journal of Chemistry 29(2), 367.
Mahato SB, Kundu AP. 1994. 13C NMR spectra of pentacyclic triterpenoids—a compilation and some salient features. Phytochemistry 37(6), 1517-1575. http://dx.doi.org/10.1016/S0031-9422(00)89569-2
Midiwo JO, Rukunga GM. 1985. Distribution of anthraquinone pigments in Rumex species of Kenya. Phytochemistry 24(6), 1390-1391. http://dx.doi.org/10.1016/S0031-9422(00)81145-0
Mueller SO, Schmitt M, Dekant W, Stopper H, Schlatter J, Schreier P, Lutz WK. 1999. Occurrence of emodin, chrysophanol and physcion in vegetables, herbs and liquors. Genotoxicity and anti-genotoxicity of the anthraquinones and of the whole plants. Food and chemical toxicology 37(5), 481-491. http://dx.doi.org/10.1016/S0278-6915(99)00027-7
Munavu RM, Mudamba LO, Ogur JA. 1984. Isolation and characterization of the major anthraquinone pigments from Rumex abysinica. Planta medica 50(01), 111-111.
Schripsema J, Dagnino D. 1996. Elucidation of the substitution pattern of 9, 10-anthraquinones through the chemical shifts of peri-hydroxyl protons. Phytochemistry 42(1), 177-184. http://dx.doi.org/10.1016/0031-9422(95)00885-3
Suri JL, Dhar KL, Atal CK. 1978. Chemical constituents of Rumex orientalis Bernh. Journal.
Takao T, Kitatani F, Watanabe N, Yagi A, Sakata K. 1994. A simple screening method for antioxidants and isolation of several anti-oxidants produced by marine bacteria from fish and shellfish. Bioscience, Biotechnology & Biochemistry 58(10), 17801783.
Abdul Khabir, Farman Ullah Khan, Zia ul Haq, Zakir Khan, Shahidullah Khan, Shafiullah Khan, 2017. Two new antioxidant anthraquinones namely Obtusifolate A and B from Rumex obtusifolius. Int. J. Biosci., 10(4), 49-57.
Copyright © 2017 by the Authors. This article is an open access article and distributed under the terms and conditions of the Creative Commons Attribution 4.0 (CC BY 4.0) license.