Subscribe to RSS
DOI: 10.1055/s-2001-11514
© Georg Thieme Verlag Stuttgart · New York
Influence of Natural and Synthetic Compounds on Cell Surface Expression of Cell Adhesion Molecules, ICAM-1 and VCAM-1
Publication History
March 23, 2000
July 16, 2000
Publication Date:
31 December 2001 (online)
Abstract
Various natural and synthetic compounds including alkaloids, terpenoids and phenolics were tested for inhibition of the cell surface expression of intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1), both of which are crucial in the regulation of immune response and inflammation. Of 40 compounds tested, two compounds significantly downregulated the expression of VCAM-1 on murine endothelial cells (F-2) and ten compounds that of ICAM-1 on mouse myeloid leukemia cells (M1). Sanguinarine chloride (5) and isoliquiritigenin (13) were capable of lowering the levels of both ICAM-1 and VCAM-1. The structure-activity relationships study on chalcone and flavone derivatives related to 13 suggested that the inhibitory activity of the chalcone derivatives is attributable to the 4-hydroxy group as well as the possible coplanarity between the phenyl ring and the adjacent conjugated ketone.
Abbreviations
ICAM-1:intercellular adhesion molecule-1
LFA-1:leukocyte function associated antigen-1
VCAM-1:vascular cell adhesion molecule-1
VLA-4:very late antigen-4
Key words
Chalcone - cell adhesion molecule - ICAM-1 - VCAM-1 - immunosuppressive, anti-inflammatory
References
- 1 Foster C A. VCAM-1/4-integrin adhesion pathway: Therapeutic target for allergic inflammatory disorders. Journal of Allergy and Clinical Immunology. 1996; 98 S270-7
- 2 Seventer G A, Newman W, Shimizu Y, Nutman T B, Tanaka Y, Horgan K J et al. Analysis of T cell stimulation by superantigen plus major histocompatibility complex class II molecules or by CD3 monoclonal antibody costimulation by purified adhesion ligands VCAM-1, ICAM-1, but not ELAM-1. Journal of Experimental Medicine. 1991; 174 901-13
- 3 Stolpe A, Saag P T. Intercellular adhesion molecule-1. Journal of Molecular Medicine. 1996; 74 13-33
- 4 Rice K C, Brossi A. Expedient synthesis of racemic and optically active N-norreticuline and N-substituted and 6′-bromo-N-norreticulines. Journal of Organic Chemistry. 1980; 45 592-601
- 5 Umezawa T, Isohata T, Kuroda H, Higuchi T, Shimada M. Chiral HPLC and LC-MS Analysis of Several Lignans. In: Kuwahara M, Shimada M, editors Biotechnology in Pulp and Paper Industry. Tokyo; Uni Publishers Co., Ltd. 1992: 507-12
- 6 Umezawa T, Shimada M. Syntheses of (±)-lariciresinols. Mokuzai Gakkaishi. 1994; 40 231-5
- 7 Heymann H, Tezuka Y, Kikuchi T, Supriyatna S. Constituents of Sindora sumatrana Miq. I. Isolation and NMR spectral analysis of sesquiterpenes from the dried pods. Chemical & Pharmaceutical Bulletin. 1994; 42 138-46
- 8 Kubota T, Kamikawa T. Derivation of gentianin from gentiopicrin. Bulletin of the Chemical Society of Japan. 1962; 35 1046
-
9 Wagner H, Farkas L.
Synthesis of Flavonoids . In: Harbone JB, Mabry TJ, Mabry H, editors The Flavonoids. New York, London; John Wiley & Sons 1975: 127-213 -
10 Wheeler T S.
Flavone . In: Rabjohn N, editor-in-chief Organic Syntheses Collective. Vol. 4 New York, London; John Wiley & Sons 1963: 478-81 - 11 Kamisako W, Suwa K, Morimoto K, Isoi K. Application of biosynthetic 13C-enrichment using [1-13C]-, [2-13C]- and [1,2-13C2]-acetate as precursor for 13C NMR spectral assignment of higher plant metabolites. Organic Magnetic Resonance. 1984; 22 93-100
- 12 Maruyama H, Toda K, Uno K, Miyake K, Matsushima K, Yamamoto K et al. Murine endothelial cell line cells, F-2: Interaction with leukocytes and cytokines production. Microbiology and Immunology. 1993; 37 895-903
- 13 Ichikawa Y. Differentiation of a cell line of myeloid leukemia. Journal of Cellular Physiology. 1969; 74 223-34
- 14 Bereta J, Bereta M, Allison A C, Kruger P B, Koj A. Inhibitory effect of di-catechol rooperol on VCAM-1 and iNOS expression in cytokine-stimulated endothelium. Life Sciences. 1997; 60 325-34
- 15 Sagara H, Matsuda H, Wada N, Yagita H, Fukuda T, Okumura K et al. Monoclonal antibody against very late antigen-4 inhibits eosinophil accumulation and late asthmatic response in a guinea pig model of asthma. International Archives of Allergy and Immunology. 1997; 112 287-94
- 16 Uchikoshi F, Ito T, Kamiike W, Moriguchi A, Nozaki S, Ito A et al. Anti-ICAM-1/LFA-1 monoclonal antibody therapy prevents graft rejection and IDDM recurrence in BB rat pancreas transplantation. Transplantation Proceedings. 1995; 27 1527-8
- 17 Tanaka S, Akimoto M, Tambe Y, Tabata M. Volatile antiallergic principles from a traditional herbal prescription of Kampo medicine. Phytotherapy Research. 1996; 10 238-41
- 18 Martin S, Padilla E, Ocete M A, Galvez J, Jimenez J, Zarzuelo A. Anti-inflammatory activity of the essential oil of Bupleurum fruticescens . Planta Medica. 1993; 59 533-6
- 19 Ivanovska N, Philipov S. Study on the anti-inflammatory action of Berberis vulgaris root extract, alkaloid fractions and pure alkaloids. International Journal of Immunopharmacology. 1996; 18 553-61
- 20 Firatli E, Unal T, Onan U, Sandalli P. Antioxidative activities of some chemotherapeutics. A possible mechanism in reducing gingival inflammation. Journal of Clinical Periodontology. 1994; 21 680-3
- 21 Kim H K, Son K H, Chang H W, Kang S S, Kim H P. Amentoflavone, a plant biflavone: a new potential anti-inflammatory agent. Archives Pharmacal Research. 1998; 21 406-10
- 22 Chaturvedi M M, Kumar A, Darnay B G, Chainy G BN, Agarwal S, Aggarwal B B. Sanguinarine (pseudochelerythrine) is a potent inhibitor of NF-κB activation IκBA phosphorylation, and degradation. Journal of Biological Chemistry. 1997; 272 30129-34
- 23 Herencia F, Ferrandiz M L, Ubeda A, Guillen I, Dominguez J N, Charris J E et al. Novel anti-inflammatory chalcone derivatives inhibit the induction of nitric oxide synthase and cyclooxygenase-2 in mouse peritoneal macrophages. FEBS Letters. 1999; 453 129-34
- 24 Mire-Sluis A. Cytokines and disease. Trend in Biotechnology. 1993; 11 74-7
Prof. Dr. S. Tanaka
Department of Bioscience
Tokyo University of Agriculture
1-1-1 Sakuragaoka
Setagaya-ku
Tokyo 156-8502
Japan
Email: stanaka@nodai.ac.jp
Fax: +81 3-5477-2762