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Anti-Inflammatory Effect and Hplc Analysis of Extract from Edible <Emphasis Type="Italic">Cirsium Setidens <

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Anti-Inflammatory Effect and Hplc Analysis of Extract from Edible <Emphasis Type= J. Korean Soc. Appl. Biol. Chem. 52(5), 437-442 (2009) Article Anti-inflammatory Effect and HPLC Analysis of Extract from Edible Cirsium setidens Sung-Hyun Lee†, Mee Jung Jung†, Seong-Il Heo, and Myeon-Hyeon Wang* School of Biotechnology, Kangwon National University, Chuncheon 200-701, Republic of Korea Received December 8, 2008; Accepted August 31, 2009 The anti-inflammatory effect of Cirsium setidens (C. setidens) roots was evaluated for its potential to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells. The ethanol (EtOH) extract of C. setidens exhibited strong anti-inflammatory activities in the NO production by LPS-stimulated RAW 264.7 cells. The individual fractions tested were, in order of most-to-least potent in anti-inflammatory activity: n-butanol (n-BuOH)>ethanol (EtOH)>water (H2O)>ethyl acetate (EtOAc)>dichloromethane (CH2Cl2). The n-BuOH soluble fraction, which exhibited the strongest anti-inflammatory activity, was further purified by repeated MCI gel, silicagel, and RP-18 gel column chromatography. Syringin, isolated from C. setidens roots for the first time, were found to inhibit NO production in LPS-induced RAW 264.7 cells. High performance liquid chromatography (HPLC) was used for the analysis of the syringin in the EtOH extract of Cirsumn species. Key words: anti-imflammatory, Cirsium setidens, MTT assay, nitric oxide, RAW 264.7 cells, syringin The Cirsium (thistle), all members of the Compositae including C. steidens leaf has attracted a lot of attention as family, have been used in traditional folk medicine as a functional health-maintenance and disease-prevention diuretic, antiphlogistic, hemostatic, and detoxifying agents food. However, the potential anti-inflammatory effects of [Lee, 1966; Kim, 1984]. A great deal of research has been C. setidens roots have not been fully investigated. conducted regarding the phytene-1,2-diol, b-sitosterol, Inflammation is a beneficial host response to foreign petolinarigenin, epilupeol acetate, apigenin, linaroside, challenge or tissue injury that leads to the recovery of siparunoside, notisopreonoids, triterpene hydorperosices, tissue structure and function [Zhou et al., 2007]. acyclic diterpenes, sesquiterpene, monoglalactosydiacy Inflammation is involved in a complex web of intercellular glycerol and sterol glycoside harbored by thistles, and a cytokine signals. Anti-inflammatory compounds have variety of activities were exhibited by these species [Lee investigated the potential inhibitory effects of natural et al., 1994; Perez et al., 2001; Chung et al., 2002; Lee et products in vitro using, lipopolysaccharide (LPS)-stimulated al., 2002; Lee and Lee, 2005; Nazaruk and Jakoniuk, macrophage. 2005]. In the present study, the anti-inflammatory activity of Cirsium setidens Nakai (Compositae), a perennial herb, the ethanol (EtOH) extract of C. setidens, along with its has been used to treat edema, bleeding hemoptysis, and organic solvent soluble fractions such as dichloromethane cancer [Lee et al.,2002]. C. setidens is used as a food and (CH2Cl2), ethyl acetate (EtOAc), n-buthanol (n-BuOH), a traditional fermented vegetable food, and Bibimbap and water (H2O) were evaluated according to nitric oxide (NO) production in LPS-induced RAW 264.7 cells. The †The first two authors are equally contributed to this work. isolation and identification of syringin from the active n- BuOH fraction of C. setidens roots was investigated. *Corresponding author Moreover, we conducted a quantitative analysis of two Phone: +82-33-250-6486; Fax: +82-33-241-6480 Cirsium species, namely C. setidens and C. japonicum, E-mail: [email protected] by analyzing syringin with HPLC-PDA. Abbreviations: n-BuOH, n-butanol; CH2Cl2, dichloromethane; EtOAc, ethyl acetate; EtOH, ethanol; H2O, water; HPLC, high- Materials and Methods performance liquid chromatography; LPS, lipopolysaccharide; NO, nitric oxide Plant extraction and purification. Roots of Cirsium doi:10.3839/jksabc.2009.076 setidens Nakai were collected in September, 2006 in 438 Sung-Hyun Lee et al. South Korea. The air-dried and chopped root powder of gel (12 nm S-75 µm, YMC Co. LTD., Kyoto, Japan). C. setidens Nakai (2.2 kg) was extracted with EtOH (18 L TLC was performed on precoated Kiesel gel 60 F254 plate ×3) at 80oC for 3 h. The total filtrate was concentrated and (0.25 µm, Merck, Darmstadt, Germany). dried in vacuo at 40oC to render the EtOH extract (225.7 Cell culture and cell viability assay. RAW 264.7 g). The extract was then suspended in distilled water and murine macrophages were obtained from Korean Cell sequentially partitioned CH2Cl2 (18.5 g), EtOAc (6.1 g), Line Bank (KCLB, Seoul, Korean). These cells were n-BuOH (41.7 g), and H2O (152.5 g). Each extract was cultured in RPMI 1640 containing 10% FBS, penicillin tested for its anti-inflammatory activity in lipopolysaccharide (100 U/mL), and streptomycin (100 µg/mL) in a 95% air, o (LPS)-induced RAW 264.7 cells, and the n-BuOH 5% CO2 humidified atmosphere at 37 C. Cell viability fraction exhibited strong activity. Therefore, n-BuOH was determined by 3-[4,5-dimethylthia-zol-2-yl]-2,5- (41.7 g) fraction loaded on a MCI gel column diphenyl tetrazolium bromide (MTT, Sigma, St. Louis, chromatography and eluted with methanol (MeOH)/H2O MO) assay. RAW 264.7 macrophages were plated at a (0:100, 40:60, 60:40, 100:0%) in a gradient mode to density of 2×105 cells in a 96-well cell culture plate with yield 4 fractions (CM1-4). Fraction CM2 (3.26 g) was 180 µL of culture medium, and incubated for 24 h. The chromatographed on a Sephadex LH-20 column cells incubated with C. setidens EtOH extract and its chromatography, using a solvent of MeOH to yield 7 fractions (1 mg/mL), and syringin (0.5, 1, 5 and 10 µM) fractions (CM2S1-7). Fraction CM2S2 (2.17 g) was for 20 h, and then 20 mL of MTT solution (2 mg/mL) chromatographyed on a silica gel column with was added to each well and incubated 2 h further. The CH2Cl2:MeOH (10:1→1:1, 0:1, gradient condition) to supernatant was carefully removed using a needle and yield 6 fractions (CM2S21-6). The fraction CM2S25 200 µL of DMSO was added to each well to dissolve (0.66 g) was rechromatographed through the repeated crystals. The absorbance at 550 nm was measured with a silica gel and RP-18 gel column chromatographies. microplate reader (Bioteck Instrucments, Winooski, VT). Finally, a lignan compound 1 (syringin, 113 mg) was Nitrite (NO) assay. RAW264.7 macrophages were isolated. plated at a density of 2×105 cells in a 96-well cell culture Chemical structure of compound 1. Pale yellow- plate with 180 µL of culture medium, and incubated for o 20 white amorphous powder; mp 185.8-186.0 C; []α D −16.9 24 h. The cells were pre-treated with EtOH extract, its (c 0.23, MeOH); LR-FABMS (positive ion mode) m/z soluble solvent fraction, and syringin (0.5, 1, 5 and 10 + 1 395 [M+Na] ; H-NMR (400 MHz, DMSO-d6) δ: 6.75 µM) and stimulated with LPS (2 µg/mL) for 20 h. The (2H, s, H-3,5), 6.54 (1H, brd, J=15.9 Hz, H-7), 6.32 (1H, nitrite concentration in the medium was measured according dt, J=5.6, 15.9 Hz, H-8), 4.85 (1H, s, Glc-1), 4.23 (2H, to the Griess reaction, and the calculated concentration dd, J=1.3, 5.6 Hz, H-9), 3.85 (6H, s, OCH3), 3.77 (1H, was taken as an indicator of NO production. Briefly, 100 dd, J=2.3, 12.0 Hz, Glc-6a), 3.67 (1H, dd, J=5.0, 12.0 µL of each supernatant was mixed with 100 µL of Griess Hz, Glc-6b), 3.48 (1H, ddd, J=2.7, 7.1 Hz, Glc-2), 3.42 reagent (1% sulfanilamide in 5% phosphoric acid and (1H, d, J=2.3 Hz, Glc-4), 3.41 (1H, d, J=2.3 Hz, Glc-5), 0.1% naphthylethylenediamine dihydrochloride in distilled 13 3.20 (1H, m, Glc-3); C-NMR (100 MHz, DMSO-d6) δ: water), and an absorbance of the mixture at 550 nm was 153.3 (C-2, 6), 134.8 (C-1), 134.3 (C-4), 130.2 (C-7), determined with a microplate reader (Bioteck Instrucments, 129.1 (C-8), 104.4 (C-3,5), 104.3 (Glc-1), 77.3 (Glc-3), Winooski, VT). 76.8 (Glc-5), 74.7 (Glc-2), 70.2 (Glc-4), 62.6 (C-9), 61.4 HPLC analysis. The EtOH extacts of C. setidens roots (Glc-6), 56.0 (OCH3). and Cirsium japonicum roots were analyzed by high General experimental procedures. Polarimeter was performance liquid chromatography (HPLC) using a measured on Perkin-Elmer 341 and FAB-MS was Waters system consisting of an M600E solvent delivery measured on Autospec. M363 series mass spectrometer. pump and M-996 photodiode array detector (PDA). The 1H and 13C-NMR spectra were measured on Bruker DPX system was controlled by Millenium-32 software. The 400 (400 MHz for 1H, 100 MHz for 13C, Karisruhe, column was Apollo C18 (4.6×250 mm; 5 mm particle Germany) spectrometer (Bruker). Chemical shift was size, Alltech Associates Inc, Deerield, IL). Elution was based on the decision of solvent peak (δH 2.50 and δC 39.5 performed in gradient mode with CH3CN/H2O (6:94- for DMSO-d6). DEPT, HMQC and HMBC spectra were 17:83, 0-30 min) at a flow rate of 1.0 mL/min. The C. measured on Bruker DPX 400. To perform column setidens (3 g) and C. japonicum (3 g) roots were extracted chromatography used Si gel [BW-820MH (S), Fuji silysia with 100 mL of EtOH by reflux and evaporated in vacuo.
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