Secondary metabolites from marine cyanobacteria and algae inhibit LFA-1/ICAM-1 mediated cell adhesion

Planta Medica

Volumn 70, Issue 2, 2004, Pages 127-131

  Takamatsu, Satoshi ^a   Nagle, Dale G ^b   Gerwick, William H ^c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c OREGON STATE UNIVERSITY   (United States)

Author keywords

Algae; Cell adhesion; Cell aggregation; Chinese hamster ovary cell; Cyanobacteria; HL 60 cell; ICAM 1; LFA 1; Marine natural products

Indexed keywords

4 HYDROXYBENZYL ALCOHOL; 7 HYDROXYCYMOPOL; ANTIINFLAMMATORY AGENT; AVRAINVILLEOL; CHLOROCYCLOHEXENONE; CYMOPOL; ECKLONIALACTONE E; HORMOTHAMNIONE; HORMOTHAMNIONE DIACETATE; INTERCELLULAR ADHESION MOLECULE 1; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1; LYNGBYA INDOLE ALDEHYDE; MALYNGAMIDE C; MALYNGAMIDE J; MALYNGAMIDE L; MALYNGOLIDE; MICROCOLIN A; MICROCOLIN B; MICROCOLIN D; UNCLASSIFIED DRUG;

ALGA; ANIMAL CELL; ARTICLE; CELL ADHESION; CELL AGGREGATION; CELL LINE; CELL STRAIN HL 60; CHO CELL; CONTROLLED STUDY; CYANOBACTERIUM; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG MECHANISM; DRUG SCREENING; HUMAN; HUMAN CELL; METABOLITE; MOLECULE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ALGAE; ANIMALS; BIOLOGICAL FACTORS; CELL ADHESION; CELL AGGREGATION; CHO CELLS; CRICETINAE; CRICETULUS; CYANOBACTERIA; FEMALE; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; INTERCELLULAR ADHESION MOLECULE-1; LYMPHOCYTE FUNCTION-ASSOCIATED ANTIGEN-1; STRUCTURE-ACTIVITY RELATIONSHIP;

ALGAE; ANIMALIA; CRICETINAE; CRICETULUS GRISEUS; CRYPTOPHYTA; CYANOBACTERIA; CYMATHERE; LYNGBYA;

EID: 1542314414     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815488     Document Type: Article

References (29)

1. Springer TA. Adhesion receptors of the immune system. Nature 1990; 346: 425-34
2. Hynes RO. Integrins: versatility, modulation, and signaling in cell adhesion. Cell 1992; 69: 11-25
3. Carlos TM, Harlan JM. Leukocyte-endothelial adhesion molecules. Blood 1994; 84: 2068-101
4. Takamatsu S, Zhang Q, Schrader KK, ElSohly HN, Walker LA. Characterization of Mycotypha metabolites found to be inhibitors of cell adhesion molecules. J Antibiot 2002; 55: 585-92
5. Zhang Q, Schrader KK, ElSohly HN, Takamatsu S. New cell-cell adhesion inhibitors from Streptomyces sp. UMA-044. J Antibiot 2003; 56: 673-81
6. Cragg GM, Newman DJ, Snader KM. Natural Products in Drug Discovery and Development. J Nat Prod 1997; 60: 52-60
7. Kobayashi M, Mahmud T, Tajima H, Wang W, Aoki S, Nakagawa S et al. Marine natural products. XXXVI. Biologically active polyacetylenes, adociacetylenes A, B, C, and D, from an Okinawan Marine sponge of Adocia sp. Chem Pharm Bull 1996; 44: 720-4
8. Burdick DJ, Paris K, Weese K, Stanley M, Beresini M, Clark K et al. N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure-activity relationship. Bioorg Med Chem Lett 2003; 13: 1015-8
9. Tanaka S, Sakata Y, Morimoto K, Tambe Y, Watanabe Y, Honda G et al. Influence of natural and synthetic compounds on cell surface expression of cell adhesion molecules, ICAM-1 and VCAM-1. Planta Med 2001; 67: 108-13
10. Ahn K-S, Kim J-H, Oh S-R, Ryu S-Y, Lee H-K. Inhibitory activity of stilbenes from medicinal plants on the expression of cell adhesion molecules on THP1 cells. Planta Med 2000; 66: 641-44
11. Lu H, Youker K, Ballantyne C, Entman M, Smith CW. Hydrogen peroxide induces LFA-1-dependent neutrophil adherence to cardiac myocytes. Am J Physiol Heart Circ Physiol 2000; 278: H835-42
12. Takamatsu S, Hodges TW, Rajbhandari I, Gerwick WH, Hamann MT, Nagle DG. Marine Natural Products as Novel Antioxidant Prototypes. J Nat Prod 2003; 66: 605-8
13. Roy S, Sen CK, Kobuchi H, Packer L. Antioxidant regulation of phorbol ester-induced adhesion of human Jurkat T-cells to endothelial cells. Free Rad Biol Med 1998; 25: 229-41
14. Tanaka S, Yoichi S, Ao L, Matumoto M, Morimoto K, Akimoto N et al. Potential immunosuppressive and antiinflammatory activities of Malaysian medicinal plants characterized by reduced cell surface expression of cell adhesion molecules. Phytotherapy Res 2001; 15: 681-6
15. Proteau PJ. Oxylipins from temperate marine algae and a photoprotective sheath pigment from blue-green algae. Ph. D. Dissertation, Oregon State University, 1993
16. Todd JS, Proteau PJ, Gerwick WH. The absolute configuration of ecklonialactones A, B, and E, novel oxylipins from brown algae of the genera Eckonia and Egregia. J Nat Prod 1994; 57: 171-4
17. Cardellina JH II, Moore RE, Arnold EV, Clardy J. Structure and absolute configuration of malyngolide, an antibiotic from the marine blue-green alga Lyngbya majuscula Gomont. J Org Chem 1976; 44: 4039-42
18. Cardellina JH II, Dalietos D, Marner FJ, Mynderse JS, Moore RE. (-)-trans-7(S)-Methoxytetradec-4-enoic acid and related amides from the marine cyanophyte Lyngbya majuscula. Phytochemistry 1978; 17: 2091-5
19. Wu M, Milligan KE, Gerwick W. Three new malyngamides from the marine cyanobacterium Lyngbya majuscula. Tetrahedron 1997; 53: 15983-90
20. Koehn FE, Longley RE, Reed JK. Microcolins A and B, new immunosuppressive peptides from the blue-green alga Lyngbya majuscula. J Nat Prod 1992; 55: 613-9
21. Yoo H-D. Bioactive secondary metabolites from marine algae and study of oxidized anandamide derivatives. Ph.D. Dissertation, Oregon State University, 1997
22. Todd JS, Gerwick WH. Isolation of a cyclic carbonate, a γ-butyrolactone, and a new indole derivative from the marine cyanobacterium Lyngbya majuscula. J Nat Prod 1995; 58: 586-9
23. Higa T. 2-(1-Chloro-2-hydroxyethyl)-4,4-dimethylcyclohexa-2,5-die-none: a precursor of 4,5-dimethylbenzo[b]furan from the red alga Desmia hornemanni. Tetrahedron Lett 1985; 26: 2335-6
24. Sun HH, Paul VJ, Fenical W. Avrainvilleol, a brominated diphenylmethane derivative with feeding deterrent properties from the tropical green alga Avrainvillea longicaulis. Phytochemistry 1983; 22: 743-5
25. Hoegberg HE, Thomson RH, King TJ. The cymopols, a group of prenylated bromohydroquinones from the green calcareous alga Cymopolia barbata. J Chem Soc Perkin Trans 1 1976: 1696-701
26. Gerwick WH, Lopez A, Van D, Gregory D, Clardy J, Ortiz W, Baez A. Hormothamnione, a novel cytotoxic styrylchromone from the marine cyanophyte Hormothamnion enteromorphoides Grunow. Tetrahedron Lett 1986; 27: 1979-82
27. Gerwick WH. 6-Desmethoxyhormothamnione, a new cytotoxic styrylchromone from the marine cryptophyte Chrysophaeum taylori. J Nat Prod 1989; 52: 252-6
28. Ayyangar NR, Khan RA, Deshpande VH. Synthesis of hormothamnione. Tetrahedron Lett 1988; 29: 2347-8
29. Flodin C, Whitfield FB. 4-Hydroxybenzoic acid: a likely precursor of 2,4,6-tribromophenol in Ulva lactuca. Phytochemistry 1999; 51: 249-55