Natural Product Sciences 15(1) : 22-26 (2009) 22 A New Naphthoquinone with Anti-inflammatory Activity from An Egyptian Collection of Echiochilon fruticosum Hoda M. Fathy, Mohamed I. Aboushoer, Azza Baraka 1 , Maged S. Abdel-Kader*, and Abdallah A. Omar Department of Pharmacognosy, Faculty of Pharmacy 1 Departmentof Pharmacology, Faculty of medicine, Alexandria University, Alexandria 21215, Egypt. 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 Introduction Several members of the family Boraginaceae are used in folk medicine as anti-inflammatory, antiseptic, and remedy for wounds (Li, 2002; Roeder, 1995). Antitumor, antimi- crobial, anti-inflammatory, contraceptive and hypotrigly- ceridemic activities were reported for members of the family (Leyva et al., 2000; Karyagina et al., 2001; Kourounakis et al., 2002; Singh et al., 2003; Zhen et al., 2002; Mats et al., 1982). Echiochilon fruticosum is distributed in the sandy and stony ground of North Africa, Sinai, Syria and Arabia (Täckholm, 1974). The nutritive value of E. fruticosum has been investigated and the possibility of its use as forage for domestic animals were demonstrated (Boshra). A variety of chemical entities has been reported from E. fruticosum, including volatile com- ponents, Eugenol glycoside, vomifoliol and trans syringin. Several flavonoid derivatives such as 5-deoxy vitexin, 5,7- dimethoxy isoflavone, dihydro robinetin, garbanzol, 5,6,7- trihydroxy flavanone, naringenin 5-methyl ether and pincomberin-7-glycoside were also isolated (Hashem, 2003; Bergaoui et al., 2004; Hammami et al., 2004). Experimental General − Silica gel (230 - 400 mesh) and C 18 -silica gel, E. Merck were used for column chromatography. Precoated TLC plates 0.25 mm, silica gel 60 (GF-254), and precoated TLC 0.20 mm, RP18 F 254 , E. Merck, were used for TLC analysis. Melting points were determined on a Sturat SMP heating stage microscope. 1D and 2D NMR analyses were obtained using jeol 500 MHz spectrometer for 1 H and 125 MHz for 13 C NMR. Residual peaks of the deuterated solvents were used to reference the spectrum. EIMS was obtained on a Delsi-Nermag R30-10, while electrospray-ionization mass spectra were carried on a Finnigan LCQ. UV-VIS spectra were carried on a Helios α thermo spectronic, England, supported with software Vision 32. Plant materials − Echiochilon fruticosum Desf. was collected from Omayed biosphere, 90 km west Alexandria, Egypt. The plant material was identified by Prof. Dr. Lotfy Boulos, National Research Center, Dokki, Cairo, Egypt. A voucher was kept in the Department of Pharma- cognosy, Faculty of Pharmacy, Alexandria University, Egypt. Extraction and Isolation − The powdered air-dried roots (400 g) were extracted by maceration with light pet. (1 × L 2). The combined extract was evaporated under reduced pressure to give 1.7 g of dark red semisolid residue. The marc left after extraction with light pet. was air dried then macerated in 70% EtOH (1 L × 2) followed by 50% EtOH (1 L × 2). Each extract was evaporated under reduced pressure to yield 3 and 6 g respectively. *Author for correspondence Tel: +00-000-0000; E-mail: mpharm101@hotmail.com .