Browse > Article

A New Naphthoquinone with Anti-inflammatory Activity from An Egyptian Collection of Echiochilon fruticosum  

Fathy, Hoda M. (Department of Pharmacognosy, Faculty of Pharmacy, Alexandria University)
Aboushoer, Mohamed I. (Department of Pharmacognosy, Faculty of Pharmacy, Alexandria University)
Baraka, Azza (Department of Pharmacology, Faculty of medicine, Alexandria University)
Abdel-Kader, Maged S. (Department of Pharmacognosy, Faculty of Pharmacy, Alexandria University)
Omar, Abdallah A. (Department of Pharmacognosy, Faculty of Pharmacy, Alexandria University)
Publication Information
Natural Product Sciences / v.15, no.1, 2009 , pp. 22-26 More about this Journal
Abstract
Phytochemical investigation of the roots of Echiochilon fruticosum resulted in the isolation of two naphthoquinone derivatives. Compound 1 was identified as anhydroalkanin while compound 2 was identified as a new derivative 5-hydroxy 8-methoxy 2-(4-methylpent-1,3-dienyl) naphthalene-1,4-dione named as echiochiloquinone. In addition, caffeic acid 3, caffeic acid methyl ester 4 were isolated. The structures were determined by physical, chemical and spectral methods. The anti-inflammatory activity of the root extracts and compound 2 was evaluated utilizing both cotton pellet-induced and carragenin-induced rat paw edema. The ulcerogenic effect was also studied.
Keywords
Echiochilon fruticosum; Naphthoquinones; Echiochiloquinone; Caffeic acid; Anti-inflammatory; Ulcerogenic;
Citations & Related Records

Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Hammami, S., Ben Janet, H., Bergaoui, A., Ciavatta, L., Cimino, G., andMighri, Z., Isolation and structure elucidation of a flavanone glycosideand vomifoliol from Echiochilon fruticosum growing in Tunisia.Molecules. 9, 602-608 (2004)   DOI   ScienceOn
2 Han, J. and Kaishim, B., Antioxidants from a chinese medicinal herbLithospermum erythrorhizon. Food Chem. 106, 2-10 (2008)   DOI   ScienceOn
3 Hashem, A., Phytochemical study of Echiochilon fruticosum Desf.Bulletin Of the National Research Centre (EGYPT). 28, 151-162(2003)
4 Karyagina, T., Arumanyan, V., Timchenko, T., and Airamshyili, D.,Antimicrobial activity of shikonin preparations. PharmaceuticalChemistry Journal, (translation of khimiko-farmateyticheskii Zhurnal).35, 435-436 (2001)   ScienceOn
5 Kourounakis, A.P., Assimopoulou, A.A.N., Papageorgiou, A.G., Gavalas,A., and Kourounakis, P.N., Alkanin and shikonin effect on free radicleprocess and on inflammation-A preliminary pharmacochemicalinvestigation. Archiv der Pharmazie. 6, 262-266 (2002)
6 Papageorgiou, V.P., 1HNMR spectra of naturally occuring isohenylnaphthazarin pigments. Planta Med. 185-187 (1979)   PUBMED
7 Tackholm, V., Student's flora of Egypt, 2nd Ed, Cairo University Press(1974)
8 Afzal, M. and Tofeeq, M., 5,8-dihydroxy-2,4-(4-methylpent-3-enyl)-1,4-naphthoquinone and its 2-[4-methyl-1-(2-methylcrotonyloxy)pent-3-enyl] analogue (shikonin angelate) from Alkanna hirsutissima. J.Chem. Soci. Perkin I. 1334-1335 (1975)
9 Boshra, S., Omayed biosphere reserve and its hinterland, EGYPT,www.UNESCO.org/mab/ecosyst/dryland
10 Zhen, H., Liao, M., and Guo, J., Contraceptive constituents from Arnebiaeuchroma (Royle) Johnst. Tianran Chanwu Yanjui Yu Khaifa. 14, 1-4(2002)
11 Suleyman, H., Demirezer, L.O., Kurunzum, A., Banoglu, Z.N., Gocer, F.,and Ozbakir, G., Anti inflammatory effect of the aqueous extract fromRumex patientia L. roots. J. Ethnopharmacol. 65, 141-148 (1999)   DOI   ScienceOn
12 Bergaoui, A., Hammami, S., Ben Janet, H., Ciavatta, L., Cimino, G., andMighri, Z., Isolation of two O-heterosides from Echiochilonfruticosum plant growing in Tunisia. Journal de la Societe Algeriennede Chimie. 14, 235-244 (2004)   ScienceOn
13 Roeder, E., Medicinal plants in Europe containing pyrrolizidine alkaloids. Pharmazie. 50, 83-98 (1995)   PUBMED   ScienceOn
14 Thomson, R.H., Naturally occuring quinones. Academic Press (1971)
15 Komatsu, T., Awata, H., Sakai, Y., and Yamanoto H., Additional data onanti inflammatory agent, ID-955. Arzneim Forsch (Drug research).23, 500-503 (1973)   ScienceOn
16 Singh, B., Sharma, M.K., Meghwal, P., and Singh, S., Anti inflammatoryactivity of shikonin derivatives from Arnebia hispidissima.Phytomedicine. 10, 375-380 (2003)   DOI   ScienceOn
17 Leyva, A., Pessoa, C., Boogaert, F., Sokaroski, R., Lemos, T.L.G.,Wetmore, L.A., Huruta, R.R., and Moraes, M.O., Oncocalyxones Aand C, 1,4-anthracendiones from Auxemma oncocalyx: Comparisonwith anticancer 1,9-anthracenediones. Anticancer Research. 20(2A),1029-1031 (2000)
18 Li, T.S.C., Chinese and related North American herbs: Phytopharmacologyand therapeutic values. CRC press, Boca Raton, Florida(2002)
19 Winter, C.A., Risley, E.A., and Nuss, G.W., Carrageenin induced oedemain hind paw of the rat as assay for anti inflammatory drugs.Experimental Biology and Medicine. 111, 544-547 (1962)   DOI
20 Mats, M.N., Korkhov, V.V., Bogatkina, V.F., Ovacharenko, S.N., Kozhina,I.S., Shukhobodskii, B.A., and Nosova, L.I., Contraceptive propertiesof galenics from several plants of the family Boraginaceae.Rastitel'nye Resursy. 18, 87-91 (1982)
21 Khatoon, S. and Mehrota, S., Pharmacognostical study of Japanese drug'Nan-Shikon', root of Arnebia euchroma growing in India. Naturalmedicines. 54, 171-177 (2000)
22 Inoue, K., Akaji, M., and Inouye, H., Quinones and related compounds inhigher plants. XXI. New findings on the proton and carbon-13 nuclearmagnetic resonance spectra of shikonin. Chem. Pharm. Bull. 9, 3993-3997 (1985)