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Published in: Journal of Thrombosis and Thrombolysis 2/2011

01-02-2011

Anticoagulation and antiplatelet effects of a dolastane diterpene isolated from the marine brown alga Canistrocarpus cervicornis

Authors: Laura de Andrade Moura, Éverson Miguel Bianco, Renato Crespo Pereira, Valéria Laneuville Teixeira, André Lopes Fuly

Published in: Journal of Thrombosis and Thrombolysis | Issue 2/2011

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Abstract

Marine brown algae of the family Dictyotaceae are rich sources of monocyclic, bicyclic, and tricyclic diterpenes. These molecules are responsible for a wide range of pharmacological and ecological functions, as antitumor and antiviral. Here, we analyzed the effect of the dolastane diterpene (4R, 9S, 14S)-4α-Acetoxy-9β,14α-dihydroxydolast-1(15),7-diene, isolated from the marine brown alga, Canistrocarpus cervicornis on blood clotting and platelet aggregation. The dolastane diterpene was able to inhibit either plasma or fibrinogen coagulation induced by thrombin as well as delayed coagulation in the recalcification test. The dolastane diterpene impaired, in a concentration-dependent manner platelet aggregation induced by collagen or adenosine diphosphate with no lysis on such cells. Thus, the dolastane diterpene maybe a promising source of natural inhibitors for hemostatic disturbs (clotting and platelet aggregation) leading to the discovery of drugs of potential use as antithrombotic and antiplatelet. In addition, the dolastane diterpene may be used as a molecular model for development of new antithrombotic agents giving new approaches to the management to the treatment of thrombotic disturbs.
Literature
1.
go back to reference Esmon CT (2000) Regulation of blood coagulation. Biochim Biophys Acta 7:349–360CrossRef Esmon CT (2000) Regulation of blood coagulation. Biochim Biophys Acta 7:349–360CrossRef
3.
go back to reference de Azevedo TC, Bezerra ME, Santos MG, Souza LA, Marques CT, Benevides NM, Leite EL (2009) Heparinoids algal and their anticoagulant, hemorrhagic activities and platelet aggregation. Biomed Pharmacother 63:477–483CrossRefPubMed de Azevedo TC, Bezerra ME, Santos MG, Souza LA, Marques CT, Benevides NM, Leite EL (2009) Heparinoids algal and their anticoagulant, hemorrhagic activities and platelet aggregation. Biomed Pharmacother 63:477–483CrossRefPubMed
4.
go back to reference Melo FR, Pereira MS, Monteiro RQ, Foguel D, Mourão PA (2008) Sulfated galactan is a catalyst of antithrombin-mediated inactivation of α-thrombin. Biochim Biophys Acta 1780:1047–1053PubMed Melo FR, Pereira MS, Monteiro RQ, Foguel D, Mourão PA (2008) Sulfated galactan is a catalyst of antithrombin-mediated inactivation of α-thrombin. Biochim Biophys Acta 1780:1047–1053PubMed
5.
go back to reference Béguin S, Lindhout T, Hemker HC (1988) The mode of action of heparin in plasma. Thromb Haemost 60:457–462PubMed Béguin S, Lindhout T, Hemker HC (1988) The mode of action of heparin in plasma. Thromb Haemost 60:457–462PubMed
6.
go back to reference Melo FR, Pereira MS, Foguel D, Mourão PA (2004) Antithrombin-mediated anticoagulant activity of sulfated polysaccharides: different mechanisms for heparin and sulfated galactans. J Biol Chem. 14:20824–20835CrossRef Melo FR, Pereira MS, Foguel D, Mourão PA (2004) Antithrombin-mediated anticoagulant activity of sulfated polysaccharides: different mechanisms for heparin and sulfated galactans. J Biol Chem. 14:20824–20835CrossRef
7.
go back to reference König GM, Wright AD, Sticher O, Angerhofer CK, Pezzuto JM (1994) Biological activities of selected marine natural products. Planta Med 60:532–537CrossRefPubMed König GM, Wright AD, Sticher O, Angerhofer CK, Pezzuto JM (1994) Biological activities of selected marine natural products. Planta Med 60:532–537CrossRefPubMed
8.
go back to reference König GM, Wright AD, Franzblau SG (2000) Assessment of antimycobacterial activity of a series of mainly marine derived natural products. Planta Med 66:337–342CrossRefPubMed König GM, Wright AD, Franzblau SG (2000) Assessment of antimycobacterial activity of a series of mainly marine derived natural products. Planta Med 66:337–342CrossRefPubMed
9.
go back to reference Pereira HS, Leão-Ferreira LR, Moussatché N, Teixeira VL, Cavalcanti DN, Costa LJ, Diaz R, Frugulhetti IC (2004) Antiviral activity of diterpenes isolated from the Brazilian marine alga Dictyota menstrualis against human immunodeficiency virus type 1 (HIV-1). Antiviral Res 64:69–76PubMed Pereira HS, Leão-Ferreira LR, Moussatché N, Teixeira VL, Cavalcanti DN, Costa LJ, Diaz R, Frugulhetti IC (2004) Antiviral activity of diterpenes isolated from the Brazilian marine alga Dictyota menstrualis against human immunodeficiency virus type 1 (HIV-1). Antiviral Res 64:69–76PubMed
10.
go back to reference Kolesnikova SA, Kalinovsky AI, Fedorov SN, Shubina LK, Stonik VA (2006) Diterpenes from the Far-eastern brown alga Dictyota dichotoma. Phytochemistry 67:2115–2119CrossRefPubMed Kolesnikova SA, Kalinovsky AI, Fedorov SN, Shubina LK, Stonik VA (2006) Diterpenes from the Far-eastern brown alga Dictyota dichotoma. Phytochemistry 67:2115–2119CrossRefPubMed
11.
go back to reference Jongaramruong J, Kongkam N (2007) Novel diterpenes with cytotoxic, anti-malarial and anti-tuberculosis activities from a brown alga Dictyota sp. J Asian Nat Prod Res 9:743–751CrossRefPubMed Jongaramruong J, Kongkam N (2007) Novel diterpenes with cytotoxic, anti-malarial and anti-tuberculosis activities from a brown alga Dictyota sp. J Asian Nat Prod Res 9:743–751CrossRefPubMed
12.
go back to reference Matsubara K (2004) Recent advances in marine algal anticoagulants. Curr Med Chem Cardiovasc Hematol Agents 2:13–19CrossRefPubMed Matsubara K (2004) Recent advances in marine algal anticoagulants. Curr Med Chem Cardiovasc Hematol Agents 2:13–19CrossRefPubMed
13.
go back to reference Mourão PA (2004) Use of sulfated fucans as anticoagulant and antithrombotic agents: future perspectives. Curr Pharm Des 10:967–981CrossRefPubMed Mourão PA (2004) Use of sulfated fucans as anticoagulant and antithrombotic agents: future perspectives. Curr Pharm Des 10:967–981CrossRefPubMed
14.
go back to reference Teixeira VL, Tomassini T, Fleury BG, Kelecon A (1986) Dolastane and secodolastane diterpenes from the marine brown alga, Dictyota cervicornis. J Nat Prod 49:570–575CrossRef Teixeira VL, Tomassini T, Fleury BG, Kelecon A (1986) Dolastane and secodolastane diterpenes from the marine brown alga, Dictyota cervicornis. J Nat Prod 49:570–575CrossRef
15.
go back to reference Vallim MA, de Paula JC, Pereira RC, Teixeira VL (2005) The diterpenes from Dictyotacea marine brown algae in the Tropical Atlantic American region. Biochem Syst Ecol 33:1–16CrossRef Vallim MA, de Paula JC, Pereira RC, Teixeira VL (2005) The diterpenes from Dictyotacea marine brown algae in the Tropical Atlantic American region. Biochem Syst Ecol 33:1–16CrossRef
16.
go back to reference de Clerck O, Leliaert F, Verbruggen H, Lane CE, de Paula JC, Payo DA, Eric CA (2006) A revised classification of the dictyoteae (Dictyotales, Phaeophyceae) based on rbcL and 26 s ribosomal DNA sequence analyses. J Phycol 42:1271–1288CrossRef de Clerck O, Leliaert F, Verbruggen H, Lane CE, de Paula JC, Payo DA, Eric CA (2006) A revised classification of the dictyoteae (Dictyotales, Phaeophyceae) based on rbcL and 26 s ribosomal DNA sequence analyses. J Phycol 42:1271–1288CrossRef
17.
go back to reference Kim JY, Alamsjah MA, Hamada A, Fujita Y, Ishibashi F (2006) Algicidal diterpenes from the brown alga Dictyota dichotoma. Biosci Biotechnol Biochem 70:2571–2574CrossRefPubMed Kim JY, Alamsjah MA, Hamada A, Fujita Y, Ishibashi F (2006) Algicidal diterpenes from the brown alga Dictyota dichotoma. Biosci Biotechnol Biochem 70:2571–2574CrossRefPubMed
18.
go back to reference Costa LS, Fidelis GP, Cordeiro SL, Oliveira RM, Sabry DA, Camara RB, Nobre LT, Costa MS, Almeida-Lima J, Farias EH, Leite EL, Rocha HA (2010) Biological activities of sulfated polysaccharides from tropical seaweeds. Biomed Pharmacother 64:21–28CrossRefPubMed Costa LS, Fidelis GP, Cordeiro SL, Oliveira RM, Sabry DA, Camara RB, Nobre LT, Costa MS, Almeida-Lima J, Farias EH, Leite EL, Rocha HA (2010) Biological activities of sulfated polysaccharides from tropical seaweeds. Biomed Pharmacother 64:21–28CrossRefPubMed
19.
go back to reference Albuquerque IR, Queiroz KC, Alves LG, Santos EA, Leite EL, Rocha HA (2004) Heterofucans from Dictyota menstrualis have anticoagulant activity. Braz J Med Biol Res 37:167–171CrossRefPubMed Albuquerque IR, Queiroz KC, Alves LG, Santos EA, Leite EL, Rocha HA (2004) Heterofucans from Dictyota menstrualis have anticoagulant activity. Braz J Med Biol Res 37:167–171CrossRefPubMed
20.
go back to reference Garcia DG, Bianco EM, Santos MC, Pereira RC, Faria MV, Teixeira VL, Burth P (2009) Inhibition of mammal Na(+)K(+)-ATPase by diterpenes extracted from the Brazilian brown alga Dictyota cervicornis. Phytother Res 23:943–947CrossRefPubMed Garcia DG, Bianco EM, Santos MC, Pereira RC, Faria MV, Teixeira VL, Burth P (2009) Inhibition of mammal Na(+)K(+)-ATPase by diterpenes extracted from the Brazilian brown alga Dictyota cervicornis. Phytother Res 23:943–947CrossRefPubMed
21.
go back to reference González AG, Martin JD, Norte M, Rivera P, Perales A, Fayos J (1988) Structure and absolute configurations of Dictyota sp. diterpenes. Tetrahedron 339:3355–3357 González AG, Martin JD, Norte M, Rivera P, Perales A, Fayos J (1988) Structure and absolute configurations of Dictyota sp. diterpenes. Tetrahedron 339:3355–3357
22.
go back to reference Fuly AL, Machado OL, Alves EW, Carlini CR (1997) Mechanism of inhibitory action on platelet activation of a phospholipase A2 isolated from Lachesis muta (Bushmaster) snake venom. Thromb Haemost 78:1372–1380PubMed Fuly AL, Machado OL, Alves EW, Carlini CR (1997) Mechanism of inhibitory action on platelet activation of a phospholipase A2 isolated from Lachesis muta (Bushmaster) snake venom. Thromb Haemost 78:1372–1380PubMed
23.
go back to reference Ardlie NG, Packham MA, Mustard JF (1970) Adenosine diphosphate-induced platelet aggregation in suspensions of washed rabbit platelets. Br J Haematol 19:7–17CrossRefPubMed Ardlie NG, Packham MA, Mustard JF (1970) Adenosine diphosphate-induced platelet aggregation in suspensions of washed rabbit platelets. Br J Haematol 19:7–17CrossRefPubMed
24.
go back to reference Licari LG, Kovacic JP (2009) Thrombin physiology and pathophysiology. Vet Emerg Crit Care 19:11–22CrossRef Licari LG, Kovacic JP (2009) Thrombin physiology and pathophysiology. Vet Emerg Crit Care 19:11–22CrossRef
25.
go back to reference Tanaka KA, Key NS, Levy JH (2009) Blood coagulation: hemostasis and thrombin regulation. Anesth Analg 108:1433–1446CrossRefPubMed Tanaka KA, Key NS, Levy JH (2009) Blood coagulation: hemostasis and thrombin regulation. Anesth Analg 108:1433–1446CrossRefPubMed
26.
go back to reference Beretz A, Cazenave JP (1991) Old and new natural products as the source of modern antithrombotic drugs. Planta Med 57:S68–S72CrossRef Beretz A, Cazenave JP (1991) Old and new natural products as the source of modern antithrombotic drugs. Planta Med 57:S68–S72CrossRef
27.
go back to reference Trento F, Cattaneo F, Pescador R, Porta RL (2001) Antithrombin activity of an algal polysaccharide. Thromb Res 102:457–465CrossRefPubMed Trento F, Cattaneo F, Pescador R, Porta RL (2001) Antithrombin activity of an algal polysaccharide. Thromb Res 102:457–465CrossRefPubMed
28.
go back to reference Michelson AD (2010) Antiplatelet therapies for the treatment of cardiovascular disease. Nat Rev Drug Discov 9:154–169CrossRefPubMed Michelson AD (2010) Antiplatelet therapies for the treatment of cardiovascular disease. Nat Rev Drug Discov 9:154–169CrossRefPubMed
29.
go back to reference Lasser G, Guchhait P, Ellsworth JL, Sheppard P, Lewis K, Bishop P (2006) C1qTNF-related protein-1 (CTRP-1): a vascular wall protein that inhibits collagen-induced platelet aggregation by blocking VWF binding to collagen. Blood 107:423–430CrossRefPubMed Lasser G, Guchhait P, Ellsworth JL, Sheppard P, Lewis K, Bishop P (2006) C1qTNF-related protein-1 (CTRP-1): a vascular wall protein that inhibits collagen-induced platelet aggregation by blocking VWF binding to collagen. Blood 107:423–430CrossRefPubMed
30.
go back to reference Rocha HA, Moraes FA, Trindade ES, Franco CR, Torquato RJ, Veiga SS, Valente AP, Mourão PA, Leite EL, Nader HB, Dietrich CP (2005) Structural and hemostatic activities of a sulfated galactofucan from the brown alga Spatoglossum schroederi. An ideal antithrombotic agent? J Biol Chem 280:41278–41288CrossRefPubMed Rocha HA, Moraes FA, Trindade ES, Franco CR, Torquato RJ, Veiga SS, Valente AP, Mourão PA, Leite EL, Nader HB, Dietrich CP (2005) Structural and hemostatic activities of a sulfated galactofucan from the brown alga Spatoglossum schroederi. An ideal antithrombotic agent? J Biol Chem 280:41278–41288CrossRefPubMed
31.
go back to reference Barroso EM, Costa LS, Medeiros VP, Cordeiro SL, Costa MS, Franco CR, Nader HB, Leite EL, Rocha HA (2008) A non-anticoagulant heterofucan has antithrombotic activity in vivo. Planta Med 74:712–718CrossRefPubMed Barroso EM, Costa LS, Medeiros VP, Cordeiro SL, Costa MS, Franco CR, Nader HB, Leite EL, Rocha HA (2008) A non-anticoagulant heterofucan has antithrombotic activity in vivo. Planta Med 74:712–718CrossRefPubMed
32.
go back to reference Mayer AM, Rodríguez AD, Berlinck RG, Hamann MT (2009) Marine pharmacology in 2005–2006: marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune and nervous systems, and other miscellaneous mechanisms of action. Biochim Biophys Acta 1790:283–308PubMed Mayer AM, Rodríguez AD, Berlinck RG, Hamann MT (2009) Marine pharmacology in 2005–2006: marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune and nervous systems, and other miscellaneous mechanisms of action. Biochim Biophys Acta 1790:283–308PubMed
33.
go back to reference Domingos TF, Carvalho C, Moura LA, Teixeira VL, Pereira RC, Bianco EM, Ferreira WJ, Ramos CJ, de Miranda AL, Melo PA, Guimarães JA, Fuly AL (2009) Antilonomic effects of Brazilian brown seaweed extracts. Nat Prod Commun 4:1075–1078PubMed Domingos TF, Carvalho C, Moura LA, Teixeira VL, Pereira RC, Bianco EM, Ferreira WJ, Ramos CJ, de Miranda AL, Melo PA, Guimarães JA, Fuly AL (2009) Antilonomic effects of Brazilian brown seaweed extracts. Nat Prod Commun 4:1075–1078PubMed
34.
go back to reference Abrantes JL, Barbosa J, Cavalcanti D, Pereira RC, Frederico Fontes CL, Teixeira VL, Moreno Souza TL, Paixão IC (2010) The effects of the diterpenes isolated from the Brazilian brown algae Dictyota pfaffii and Dictyota menstrualis against the herpes simplex type-1 replicative cycle. Planta Med 76:339–344CrossRefPubMed Abrantes JL, Barbosa J, Cavalcanti D, Pereira RC, Frederico Fontes CL, Teixeira VL, Moreno Souza TL, Paixão IC (2010) The effects of the diterpenes isolated from the Brazilian brown algae Dictyota pfaffii and Dictyota menstrualis against the herpes simplex type-1 replicative cycle. Planta Med 76:339–344CrossRefPubMed
Metadata
Title
Anticoagulation and antiplatelet effects of a dolastane diterpene isolated from the marine brown alga Canistrocarpus cervicornis
Authors
Laura de Andrade Moura
Éverson Miguel Bianco
Renato Crespo Pereira
Valéria Laneuville Teixeira
André Lopes Fuly
Publication date
01-02-2011
Publisher
Springer US
Published in
Journal of Thrombosis and Thrombolysis / Issue 2/2011
Print ISSN: 0929-5305
Electronic ISSN: 1573-742X
DOI
https://doi.org/10.1007/s11239-010-0545-6

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