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Anti-Inflammatory Activity of Phenylpropanoids and Phytoquinoids from Illicium Species in RBL-2H3 Cells

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Anti-Inflammatory Activity of Phenylpropanoids and Phytoquinoids from Illicium Species in RBL-2H3 Cells Anti-Inflammatory Activity of mediate phase and the latter is released in the late phase of type I allergic reactions [9], [10]. Phenylpropanoids and Phytoquinoids from Illicium Species in RBL-2H3 Cells This study was conducted to investigate the anti-inflammatory activity of the compounds isolated from Illicium species on mast Takuya Matsui1,2, Chihiro Ito1, Masataka Itoigawa3, Tadashi Okada2, cells. We analyzed the effect of six phenylpropanoids (1±6) and Hiroshi Furukawa1 six phytoquinoids (7±12), isolated from three Illicium species (Fig.1), on histamine release and TNF-a production and/or secre- tion from A23187-stimulated rat basophilic leukemia RBL-2H3 Abstract cells. Two phenylpropanoids, 1-allyl-3,5-dimethoxy-4-(3-methyl-but- Among the compounds tested, phenylpropanoids 4 and 6 and 2-enyloxy)benzene (4) and 4-allyl-2,6-dimethoxy-3-(3-methyl- phytoquinoids 7 and 8 at a concentration of 50 mM markedly in- 2-butenyl)phenol (6), and two phytoquinoids, 4R-(±)-illicinone- hibited histamine release from RBL-2H3 cells (96.9 2.9%, 84.3 Letter A(7) and 2S,4R-(±)-illicinone-B (8), isolated from plants of the 4.1%, 99.4 1.0% and 98.3 1.9% inhibition, respectively), Illicium species significantly inhibited histamine release from whereas the inhibition rate of the standard reference epigalloca- rat basophilic leukemia (RBL-2H3) cells stimulated with thechin gallate (EGCG) was 28.6 6.0% (Fig. 2A). These com- A23187. Furthermore, these compounds caused a decline in pounds showed a dose-dependent inhibitory effect in the con- TNF-a levels in culture supernatants of RBL-2H3 cells following centration range of 1±50 mM on histamine release without ap- treatment with A23187. The results indicate that these com- parent cytotoxicity at the highest concentration (50 mM) pounds might be useful as anti-inflammatory agents against (Fig. 2B). The IC50 values of phenylpropanoids 4 and 6 were calcu- mast cell-mediated inflammatory diseases. lated as 20.2 0.4 mM and 23.1 3.3 mM, respectively. The IC50 values of phytoquinoids 7 and 8 (16.2 2.2 mM and 15.7 Abbreviations 0.6 mM, respectively) were only slightly lower than those of phe- MTT assay: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazo- nylpropanoids 4 and 6. These results show that phenylpropa- lium bromide noids 4 and 6 and phytoquinoids 7 and 8 have an inhibitory ef- TNF-a: tumor necrosis factor-a fect on histamine release from mast cells. Supporting information available online at Based on the results obtained from the histamine release experi- http://www.thieme-connect.de/ejournals/toc/plantamedica ments, phenylpropanoids 4 and 6 and phytoquinoids 7 and 8 at 50 mM were assayed for a possible effect on TNF-a production and/or secretion from RBL-2H3 cells stimulated with A23187. Japanese star anise (Illicium anisatum L., Japanese name, Sikimi) The concentrations of TNF-a in the cultured supernatant from (Illiciaceae) has been reported to be neurologically and gastroin- RBL-2H3 cells pretreated with phytoquinoids 7 and 8 were re- testinally toxic [1], [2]. In our previous studies, several phenyl- duced by 87.4% and 83.1% compared to A23187-stimulated RBL- propanoids and phytoquinoids isolated from Illicium species [3], 2H3 cells (Fig. 3). Phenylpropanoids 4 and 6 also significantly re- [4], [5] were shown to have cancer chemopreventive activity [6]. duced TNF-a levels by 80.8 % and 30.0%, respectively (Fig. 3). In other reports, phenylpropanoids from Curcuma zedoaria (Zin- These findings suggest that phenylpropanoids 4 and 6 and phy- giberaceae) and Stella dichotoma L. var. lancolata (Caryophylla- toquinoids 7 and 8 have the potential to attenuate late-phase al- ceae) were reported to inhibit TNF-a release from mast cells [7], lergic reactions in mast cells. The inhibitory effect of phenylpro- [8], suggesting an anti-inflammatory effect. However, the effect panoids 4 and 6 on TNF-a production and/or secretion supports of other compounds isolated from Illicium plants on mast cells earlier reports [7], [8], [11], [12], [13]. Furthermore, the present is not yet fully understood. Mast cells play a central role in type report is the first to show that phytoquinoids suppress the pro- I allergic inflammatory reactions and in chronic inflammation duction and/or secretion of TNF-a from mast cells. associated with fibrosis. Histamine and TNF-a are the major che- mical mediators in mast cells. The former is released in the im- One structural feature common to the active phenylpropanoids 4 and 6 is the presence of a prenyl moiety on the aromatic ring. Furthermore, the O-prenylated 4 showed a greater inhibition of TNF-a activity than the C-prenylated 6. The presence of the O- Affiliation: 1 Faculty of Pharmacy, Meijo University, Tempaku-ku, Nagoya, or C-prenyl moiety in the molecule seems to influence the inhi- Aichi, Japan ´ 2 Department of Physiology, Aichi Medical University, Nagakute- bitory activity towards TNF-a production and/or secretion from 3 cho, Aichi-gun, Aichi, Japan ´ Faculty of Human Wellness, Tokai Gakuen Uni- RBL-2H3 cells. Phenylpropanoids 1, 2 and 3 have no prenyl group, versity, Tempaku, Nagoya, Aichi, Japan and the inhibitory effect of compounds 1 and 2 on histamine re- Correspondence: Dr. Takuya Matsui ´ Department of Medicinal Chemistry, Fa- lease was lower than that of compound 3 (Fig. 2A). Based on this culty of Pharmacy ´ Maijo University ´ Yagotoyama 150 ´ Tempaku-ku ´ Nagoya 468±8503 ´ Japan ´ Phone: +81-52-832-1781 ´ Fax: +81-52-834-8090 ´ E-mail: observation, the methylenedioxy ring system in these aromatic [email protected] molecules does not appear to be necessary for inhibitory activity. Received December 23, 2005 ´ Revised April 5, 2007 ´ Accepted April 24, 2007 On the other hand, among the phytoquinoids (7±12) which are Bibliography: Planta Med Georg Thieme Verlag KG Stuttgart ´ New York ´ constructed from 2,5-cyclohexadien-1-one or its dihydro skele- DOI 10.1055/s-2007-981528 ´ Published online 2007 ´ ISSN 0032-0943 ton, only phytoquinoids 7 and 8 inhibited histamine release and Fig. 1 Structures of phenylpropanoids (1±6) and phyto- quinoids (7±12) isolated from Illicium species. Letter Fig. 2 Inhibitory effects of phenylpropanoids and phyto- quinoids on histamine release from RBL-2H3 cells. A Com- parison of six phenylpropanoids (1±6) and six phytoqui- noids (7±12) at a concentration of 50 mM for the inhibition of histamine release from RBL-2H3 cells in response to A23187 (2 mM). RBL-2H3 cells were pretreated with the test compounds for 30 min at 37 8C and were stimulated with A23187 for 30 min at 37 8C. The white bar shows the stand- ard reference epigallocathechin gallate (EGCG). Bars repre- sent the mean + SD (n = 5). Significantly different from EGCG, **, p < 0.01. B Dose-response analysis of phenylpro- panoids 4 and 6 and phytoquinoids 7 and 8 at concentra- tions of 1, 5, 10, 25 and 50 mM. Results are shown as mean + SD (n = 3). * and **, p < 0.05 and p < 0.01, respectively for percent histamine release from RBL-2H3 cells treated with A23187 (2 mM) in the presence versus absence of the test compounds (not shown). Letter ¼ Planta Med Fig. 3 Inhibition of TNF-a production and/or secretion from RBL-2H3 cells by phenylpropanoids 4 and 6 and phyto- quinoids 7 and 8 at a concentration of 50 mM. Bars represent the mean + SD (n = 3). * and **, p < 0.05 and p < 0.01, respectively for TNF-a levels in the culture supernatant from RBL-2H3 cells treated with A23187 (2 mM) in the pres- ence of the test compounds (black bar) versus that in the ab- sence of the test compounds (white bar). Letter TNF-a production and/or secretion. The inhibitory activities of Cell culture: The RBL-2H3 cells obtained from the National Insti- compounds 7 and 8 on histamine release and the observed de- tute of Health Sciences (Japan Collection of Research Biosources; crease of the TNF-a concentration were similar, suggesting that cell number JCRB0023) were plated on a 96-well plate at a den- the enone and dienone moieties in these molecules may not sity of 1105 cells/well and cultured in Isocove's modified Dul- have a biological effect. The presence of an oxirane ring on the becco's medium (IMDM; Sigma-Aldrich Co.; St. Louis, MO, USA) prenyl group, as shown in phytoquinoid 9, conferred a weaker in- supplemented with 10% heat-inactivated FCS (Gibco BRL; Grand hibition of histamine release (Fig. 2A). Further, the lack of activ- Island, NY, USA), penicillin (Meiji Seika Kaisha, Japan) at 100 U/ ity of phytoquinoids 10, 11 and 12 demonstrates the importance mL, streptomycin (Meiji Seika Kaisha) at 100 mg/mL and 2 mM of the methylenedioxy moiety as well as the prenyl group in this glutamine (Nissui Pharmaceutical Co., Tokyo, Japan) in 5% CO2. structural system, as shown for the active compounds 7 and 8. Histamine release assay: The supernatants of stimulated RBL- As mentioned above, the present results suggest that the pres- 2H3 cells were collected and centrifuged at 400 g for 5 min at ence of a prenyl moiety (C5-terpenoid), not only on the aromatic 4 8C. Residual histamine present in the cells was released by dis- but also on the cyclic-enone molecules, seems to be necessary for rupting the cells with 1% perchloric acid, followed by centrifuga- the anti-inflammatory activity. tion at 9000g for 5 min at 4 8C. The histamine content was de- termined by HPLC, coupled with post-column derivatization We previously showed that the presence of a prenyl moiety at- fluorometry. A 5 mL sample of the supernatant was injected onto tached to the aromatic rings of naturally occurring xanthones, an ODS HPLC column (CAPCELL PAK C18 UG120 S5; Shiseido, Ja- coumarins, flavonoids and phenylpropanoids plays an important pan), with a mobile phase of 10 mM sodium heptanesulfonate role in anti-tumor promoting activity [6], [14], [15], [16], [17].
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