Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

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)
  • Published : 2009.03.31
Download PDF
⟨ Previous Next ⟩

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

References

  1. 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)
  2. 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)
  3. Boshra, S., Omayed biosphere reserve and its hinterland, EGYPT,www.UNESCO.org/mab/ecosyst/dryland
  4. 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) https://doi.org/10.3390/90700602
  5. Han, J. and Kaishim, B., Antioxidants from a chinese medicinal herbLithospermum erythrorhizon. Food Chem. 106, 2-10 (2008) https://doi.org/10.1016/j.foodchem.2007.01.031
  6. Hashem, A., Phytochemical study of Echiochilon fruticosum Desf.Bulletin Of the National Research Centre (EGYPT). 28, 151-162(2003)
  7. 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)
  8. 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)
  9. Khatoon, S. and Mehrota, S., Pharmacognostical study of Japanese drug'Nan-Shikon', root of Arnebia euchroma growing in India. Naturalmedicines. 54, 171-177 (2000)
  10. Komatsu, T., Awata, H., Sakai, Y., and Yamanoto H., Additional data onanti inflammatory agent, ID-955. Arzneim Forsch (Drug research).23, 500-503 (1973)
  11. 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)
  12. 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)
  13. Li, T.S.C., Chinese and related North American herbs: Phytopharmacologyand therapeutic values. CRC press, Boca Raton, Florida(2002)
  14. 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)
  15. Papageorgiou, V.P., 1HNMR spectra of naturally occuring isohenylnaphthazarin pigments. Planta Med. 185-187 (1979)
  16. Roeder, E., Medicinal plants in Europe containing pyrrolizidine alkaloids. Pharmazie. 50, 83-98 (1995)
  17. Singh, B., Sharma, M.K., Meghwal, P., and Singh, S., Anti inflammatoryactivity of shikonin derivatives from Arnebia hispidissima.Phytomedicine. 10, 375-380 (2003) https://doi.org/10.1078/0944-7113-00262
  18. 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) https://doi.org/10.1016/S0378-8741(98)00175-5
  19. Tackholm, V., Student's flora of Egypt, 2nd Ed, Cairo University Press(1974)
  20. Thomson, R.H., Naturally occuring quinones. Academic Press (1971)
  21. 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) https://doi.org/10.3181/00379727-111-27849
  22. Zhen, H., Liao, M., and Guo, J., Contraceptive constituents from Arnebiaeuchroma (Royle) Johnst. Tianran Chanwu Yanjui Yu Khaifa. 14, 1-4(2002)