Influence of Natural and Synthetic Compounds on Cell Surface Expression of Cell Adhesion Molecules, ICAM-1 and VCAM-1

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