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Suppressive Effects of Alloxanthin and Diatoxanthin from Halocynthia

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Suppressive Effects of Alloxanthin and Diatoxanthin from Halocynthia Journal of Oleo Science Copyright ©2008 by Japan Oil Chemists’ Society J. Oleo Sci. 57, (3) 181-189 (2008) Suppressive Effects of Alloxanthin and Diatoxanthin from Halocynthia roretzi on LPS-induced Expression of Pro-inflammatory Genes in RAW264.7 Cells Izumi Konishi1, Masashi Hosokawa1＊, Tokutake Sashima2, Takashi Maoka3 and Kazuo Miyashita1 1 Faculty of Fisheries Sciences, Hokkaido University (3-1-1 Minato, Hakodate, Hokkaido 041-8611, JAPAN) 2 Creative Research Institute, Hokkaido University (3-1-1 Minato, Hakodate, Hokkaido 041-8611, JAPAN) 3 Research Institute for Production Development (15 Shimogamo-morimoto- cho, Sakyo-ku, Kyoto 606-0805, JAPAN) Abstract: To investigate anti-inflammatory effects of carotenoids from Halocynthia roretzi, gene expression levels were measured for pro-inflammatory cytokines and enzymes in the murine macrophage-like cell line, RAW264.7, stimulated with lipopolysaccharide (LPS). All-trans alloxanthin, all-trans diatoxanthin, and their 9-cis isomers isolated from H. roretzi significantly suppressed expression of IL-1b and IL-6 mRNA in cells induced by LPS without cytotoxicity. The expression level of IL-1b mRNA in cells treated with 25 mM all-trans alloxanthin for 24 h, followed by stimulation with 0.1 mg/mL LPS for 24 h in the presence of carotenoid decreased to 33.7±3.0% from that of control cells stimulated with LPS alone. All-trans diatoxanthin, 9-cis alloxanthin and 9-cis diatoxanthin also decreased expression of IL-1b mRNA to 25.1±2.1, 28.2±0.9 and 32.9±3.3%, respectively, from that of control cells stimulated with LPS. IL-1b production in culture medium was also suppressed by all-trans alloxanthin and all-trans diatoxanthin. Furthermore, all-trans alloxanthin, all-trans diatoxanthin and their 9-cis isomers suppressed the over- expression of cyclooxygenase-2 and nitric oxide synthase mRNA in RAW264.7 cells induced by LPS. The suppressive effects of these carotenoids were remarkable compared to those of b-carotene and zeaxanthin. Key words: alloxanthin, diatoxanthin, pro-inflammatory cytokines, COX-2, iNOS, RAW264.7 cells, Halocynthia roretzi 1 INTRODUCTION induce apoptosis in human leukemia, colon and breast can- Carotenoids are a family of natural pigments with at cer cells 6,7). However, there are no reports concerning the least 700 members. Marine organisms are known to con- health benefits of alloxanthin and diatoxanthin, which are tain many kinds of carotenoids with unique structures. For the major carotenoids in H. roretzi. example, the sea squirt Halocynthia roretzi contains a Macrophages play a crucial role in inflammation and number of carotenoids including halocynthiaxanthin, allox- immunity, such as regulation of antibody production and anthin, diatoxanthin, mytiloxanthin and fucoxanthinol with secretion of cytokines 8,9). They also play an important part allenic, acetylenic and epoxicide structures in the in host defense against noxious substances 10). In addition, molecule 1,2). Previous studies have shown that holocynthi- activation of macrophages induces expression of inducible axanthin exhibits an antiproliferative effect on various cyclooxygenase-2 (COX-2) and nitric oxide synthase (iNOS) tumor cells 3), inhibition of reverse transcriptases of to produce inflammatory mediators such as prostaglandin 4) 11) 12) immunodeficiency viruses , and suppression of both super- E2 and NO . However, their excess production of inflam- oxide and nitric oxide generation 5). We and others have matory cytokines and mediators causes tissue damage also reported that halocynthiaxanthin and fucoxanthinol associated with acute and chronic inflammation, which ＊Correspondence to: Masashi Hosokawa, Faculty of Fisheries Sciences, Hokkaido University, 3-1-1 Minato, Hakodate, Hokkaido 041-8611, JAPAN E-mail: [email protected] Accepted October 26, 2007 (received for reciew August 6, 2007) Journal of Oleo Science ISSN 1345-8957 print / ISSN 1347-3352 online http://www.jstage.jst.go.jp/browse/jos/ 181 I. Konishi, M. Hosokawa, T. Sashima et al. results in inflammatory disorders 13,14). Lipopolysaccharide was purchased from Extrasynthese (Genay, France). (LPS) from Gram-negative bacteria is known to induce genes for inflammatory cytokines, COX-2 and iNOS by 2.2 Isolation of carotenoids from H. roretzi activation of macrophages through regulation of the tran- Crude lipids were extracted from H. roretzi with two scriptional factor nuclear factor-kB (NF-kB)15) and activa- volumes of acetone for 4 days at room temperature under tor protein 1 (AP-1) signaling pathways 16). It has been shade. Extraction was repeated twice. Then, acetone was demonstrated that b-carotene 17), lycopene 18) and astaxan- evaporated, and the crude lipids obtained were applied thin 19,20) suppress the LPS-induced inflammatory response onto a silica gel column with n-hexane. Non-polar lipids in the murine macrophage-like cell line, RAW264.7. In addi- were first removed by n-hexane:diethylether (95:5, v/v), tion, fucoxanthin, which is found in brown algae, has also and the crude carotenoids were then eluted with acetone. been reported to exert anti-inflammatory effects in vivo Crude carotenoids were then separated into five fractions and in vitro 21). These results suggest that other by means of preparative silica gel thin layer charomatogra- carotenoids are expected to show anti-inflammatory phy (TLC) using ethyl acetate:n-hexane (4:6, v/v) as a effects through down-regulation of the genes for pro- developing solvent. Relative front values of each fraction inflammatory cytokines, iNOS and COX-2. were 0.7 (fraction 1), 0.6 (fraction 2), 0.4 (fraction 3), 0.2 Our main focus in this study was on carotenoids isolated (fraction 4) and 0.15 (fraction 5). Since fraction 2 exhibited from H. roretzi, because these possess a similar structure the highest activity on down-regulation of IL-1b mRNA to that of fucoxanthin to exhibit anti-inflammatory effects induced by LPS, fraction 2 was further purified by a high in vitro and in vivo 21). To evaluate the anti-inflammatory performance liquid chromatography (HPLC). All-trans effects of carotenoids from H. roretzi, their suppressive alloxanthin (retention time (RT): 9.7 min), all-trans diatox- effects on the expression of pro-inflammatory genes in anthin (RT: 10.4 min), 9-cis-alloxanthin (RT: 13.5 min) and LPS-stimulated RAW264.7 cells were measured. The pre- 9-cis-diatoxanthin (RT: 15.0 min) were isolated from frac- sent results demonstrate that all-trans alloxanthin, all- tion 2 by HPLC (Hitachi L-7100, Tokyo, Japan) using two trans diatoxanthin and their 9-cis isomers can potentially connecting Develosil ODS-UG-5 columns (150 × 4.6 mm, suppress the expression of IL-1b, IL-6, COX-2 and iNOS Nomura Chemical Co., Aich, Japan). The mobile phase used mRNA in RAW264.7 cells induced by LPS. was methanol:acetonitrile (7:3, v/v) at a flow rate of 1.0 ml/min, and carotenoids were detected at 450 nm. All- trans alloxanthin (RT: 17.6 min) was further purified by HPLC with two connecting Develosil ODS-UG-5 columns 2 EXPERIMENTAL (150 × 4.6 mm) with acetonitrile at a flow rate of 1.0 2.1 Materials ml/min. H. roretzi was obtained from Marine Tec Inc. (Kamaishi, The structures of carotenoids isolated from H. roretzi Japan). RPMI 1640 medium and antibiotics were purchased were identified by UV-VIS spectra, ESI-MS, 1H NMR and from Gibco (Grand Island, NY, USA). Fetal bovine serum 13C NMR (Table 1). The UV-VIS spectra were recorded (FBS) was obtained from Thermo Trace Ltd. (Melbourne, with a Shimadzu U-240 spectrophotometer in diethyl ether Australia). LPS from Escherichia coli and b-carotene were (Et2O). The ESI-MS spectra were recorded using a JEOL purchased from Sigma (St Louis, MO, USA). Zeaxanthin JMS-700TZ mass spectrometer. The 1H NMR (500 MHz) Fig. 1 Structures of Carotenoids Isolated from H. roretzi. 182 J. Oleo Sci. 57, (3) 181-189 (2008) Anti-inflammation by Marine Carotenoids Table 1 Analytical Data of Carotenoids Isolated from H. roretzi. all-trans alloxanthin 9-cis alloxanthin all-trans diatoxanthin 9-cis diatoxanthin ESI-MS m/z 564.4 m/z 564.4 m/z 566.4 m/z 566.4 UV-VIS lmax: 427, 451, 478 (Et2O) lmax: 424, 446, 475 (Et2O) lmax: 427, 450, 477 (Et2O) lmax: 423, 445, 475 (Et2O) NMR (Position) d 13C d 1H mult. J Hz d 13C d 1H mult. J Hz d 13C d 1H mult. J Hz d 13C d 1H mult. J Hz 1 36.6 36.6 36.6 36.6 2 46.7 ax. 1.45 dd (12.5, 12.5) 46.7 ax. 1.48 dd (12.5, 12.5) 46.7 ax. 1.45 dd (12.5, 12.5) 46.7 ax. 1.48 dd (12.5, 12.5) eq. 1.84 ddd (12.5, 4, 1.5) eq. 1.85 ddd (12.5, 4, 1.5) eq. 1.84 ddd (12.5, 4, 1.5) eq. 1.85 ddd (12.5, 4, 1.5) 3 64.9 4.00 m 64.9 4.00 m 64.9 4.00 m 64.9 4.00 m 4 41.5 ax. 2.07 dd (18.5, 9) 41.5 ax. 2.09 dd (18.5, 9) 41.5 ax. 2.07 dd (18.5, 9) 41.5 ax. 2.09 dd (18.5, 9) eq, 2.43 dd (18.5, 5.5, 1.5) eq. 2.46 ddd (18.5, 5.5, 1.5) eq, 2.43 dd (18.5, 5.5, 1.5) eq. 2.46 ddd (18.5, 5.5, 1.5) 5 137.3 137.6 137.3 137.7 6 124.2 124.2 124.2 124.3 7 89.0 94.2 89.0 94.2 8 98.6 94.8 98.6 94.7 9 120.1 119.0 120.1 119.9 10 135.2 6.46 d (11) 135.3 6.30 d (11) 135.2 6.46 d (11) 135.4 6.30 d (11) 11 124.2 6.51 dd (15.5, 11) 127.3 6.83 dd (15.5,11) 124.2 6.51 dd (15.5, 11) 127.2 6.83 dd (15.5,11) 12 138.1 6.35 d (15.5) 138.1 6.35 d (15.5) 138.1 6.35 d (15.5) 138.5 6.35 d (15.5) 13 136.6 136.2 136.6 136.3 14 133.4 6.25 m 132.9 6.25 m 133.4 6.25 m 133.0 6.25 m 15 130.4 6.63 m 130.1 6.63 m 130.4 6.63 m 130.0 6.63 m 16 28.8 1.15 s 28.9 1.19 s 28.8 1.15 s 28.8 1.19 s 17 30.5 1.20 s 30.5 1.25 s 30.5 1.20 s 30.6 1.25 s 18 22.5 1.92 s 22.5 1.97 s 22.5 1.92 s 22.6 1.97 s 19 18.1 2.00 s 23.5 2.00 s 18.1 2.00 s 23.5 2.00 s 20 12.7 1.95 s 12.7 1.93 s 12.7 1.95 s 12.7 1.93 s 1’ 36.6 36.6 37.1 37.1 2’ 46.7 ax.
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