Download PDF
Planta Med 2015; 81(08): 630-636
DOI: 10.1055/s-0034-1396205
Reviews
Georg Thieme Verlag KG Stuttgart · New York

Marine and Soil Derived Natural Products: A New Source of Novel Cardiovascular Protective Agents Targeting the Endothelin System

Nadir Planes
1   Institute for Scientific Research and High Technology Services, City of Knowledge, Clayton, Panama, Republic of Panama
2   Department of Biotechnology, Acharya Nagarjuna University, Guntur, India
,
Catherina Caballero-George
1   Institute for Scientific Research and High Technology Services, City of Knowledge, Clayton, Panama, Republic of Panama
› Author Affiliations
Further Information

Publication History

received 03 August 2014
revised 15 October 2014

accepted 15 December 2014

Publication Date:
05 February 2015 (online)

   Permissions and Reprints

Abstract

Inhibition of the endothelin system is a recognized therapeutic approach for treating complex cardiovascular diseases. The search for natural inhibitors of the endothelin system has focused mainly on land, with recent, emerging data suggesting the underestimated potential of marine microorganisms for producing leads with cardioprotective potential. The present work reviews natural products identified as inhibitors of the endothelin system, their origin, their mechanism of action, and their ecological significance.

Key words

endothelin - hypertension - cardiovascular - marine natural products - microorganisms - ecology
 

  • References

  • 1 Skropeta D, Wei L. Recent advances in deep-sea natural products. Nat Prod Rep 2014; 31: 999-1025
    CrossrefPubMedGoogle Scholar
  • 2 Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR. Marine natural products. Nat Prod Rep 2014; 31: 160-258
    CrossrefPubMedGoogle Scholar
  • 3 Abad MJ, Bedoya LM, Bermejo P. Natural marine anti-inflammatory products. Mini Rev Med Chem 2008; 8: 740-754
    CrossrefPubMedGoogle Scholar
  • 4 König G, Wright AD. Marine natural products research: current directions and future potential. Planta Med 1996; 62: 193-211
    Article in Thieme ConnectPubMedGoogle Scholar
  • 5 Mayer AM, Hamann MT. Marine pharmacology in 1999: compounds with antibacterial, anticoagulant, antifungal, anthelmintic, anti-inflammatory, antiplatelet, antiprotozoal and antiviral activities affecting the cardiovascular, endocrine, immune and nervous systems, and other miscellaneous mechanisms of action. Comp Biochem Physiol C Toxicol Pharmacol 2002; 132: 315-339
    CrossrefPubMedGoogle Scholar
  • 6 Mayer AM, Rodríguez AD, Taglialatela-Scafati O, Fusetani N. Marine pharmacology in 2009–2011: marine compounds with antibacterial, antidiabetic, antifungal, anti-inflammatory, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous systems, and other miscellaneous mechanisms of action. Mar Drugs 2013; 1: 2510-2573
    PubMedGoogle Scholar
  • 7 von Lueder TG, Atar D, Krum H. Current role of neprilysin inhibitors in hypertension and heart failure. Pharmacol Ther 2014; 144: 41-49
    CrossrefPubMedGoogle Scholar
  • 8 Nasser SA, El-Mas MM. Endothelin ETA receptor antagonism in cardiovascular disease. Eur J Pharmacol 2014; 15: 210-213
    PubMedGoogle Scholar
  • 9 Miyagawa K, Emoto N. Current state of endothelin receptor antagonism in hypertension and pulmonary hypertension. Ther Adv Cardiovasc Dis 2014; 8: 202-216
    CrossrefPubMedGoogle Scholar
  • 10 Novo G, Sansone A, Rizzo M, Guarneri FP, Pernice C, Novo S. High plasma levels of endothelin-1 enhance the predictive value of preclinical atherosclerosis for future cerebrovascular and cardiovascular events: a 20-year prospective study. J Cardiovasc Med (Hagerstown) 2014; 15: 696-701
    CrossrefPubMedGoogle Scholar
  • 11 Wijesekara I, Kim SK. Angiotensin-I-converting enzyme (ACE) inhibitors from marine resources: prospects in the pharmaceutical industry. Mar Drugs 2010; 18: 1080-1093
    PubMedGoogle Scholar
  • 12 Gulavita NK, Wright AE, McCarthy PJ, Pomponi SA, Kelly-Borges M, Chin M, Sills MA. Isolation and structure elucidation of 34-sulfatobastadin 13, an inhibitor of the endothelin A receptor, from a marine sponge of the genus Ianthella . J Nat Prod 1993; 56: 1613-1617
    CrossrefPubMedGoogle Scholar
  • 13 Pairet L, Wrigley SK, Chetland I, Reynolds EE, Hayes MA, Holloway J, Ainsworth AM, Katzer W, Cheng XM, Hupe DJ. Azaphilones with endothelin receptor binding activity produced by Penicillium sclerotiorum: taxonomy, fermentation, isolation, structure elucidation and biological activity. J Antibiot (Tokyo) 1995; 48: 913-923
    CrossrefPubMedGoogle Scholar
  • 14 Caballero-George C, Sorkalla T, Jakobs D, Bolaños J, Raja H, Shearer C, Bermingham E, Häberlein H. Fluorescence correlation spectroscopy in drug discovery: study of Alexa532-endothelin 1 binding to the endothelin ETA receptor to describe the pharmacological profile of natural products. Sci World J 2012; 2012: 524169
    PubMedGoogle Scholar
  • 15 Caballero-George C. Does nature has the cure for hypertension?: Endothelin Receptors as Drug Targets. Curr Trends Biotechnol Pharm 2011; 5: 1251-1272
    PubMedGoogle Scholar
  • 16 Yanagisawa M, Kurihara H, Kimura S, Tomobe Y, Kobayashi M, Mitsui Y, Yazaki Y, Goto K, Masaki T. A novel potent vasoconstrictor peptide produced by vascular endothelial cells. Nature 1988; 332: 411-415
    CrossrefPubMedGoogle Scholar
  • 17 Simonson MS, Dunn MJ. Cellular signaling by peptides of the endothelin gene family. FASEB J 1990; 4: 2989-3000
    PubMedGoogle Scholar
  • 18 Rabelink TJ, Stroes ES, Bouter KP, Morrison P. Endothelin blockers and renal protection: a new strategy to prevent end-organ damage in cardiovascular disease. Cardiovasc Res 1998; 39: 543-549
    CrossrefPubMedGoogle Scholar
  • 19 Tirapelli CR, Fecteau MH, Honore JC, Legros E, Gobeil F, DʼOrleans-Juste P. Enzymatic pathways involved in the generation of endothelin-1(1–31) from exogenous big endothelin-1 in the rabbit aorta. Br J Pharmacol 2006; 148: 527-535
    PubMedGoogle Scholar
  • 20 Casey ML, Word RA, MacDonald PC. Endothelin-1 gene expression and regulation of endothelin mRNA and protein biosynthesis in a vascular human amnion. Potential source of amniotic fluid endothelin. J Biol Chem 1991; 266: 5762-5768
    PubMedGoogle Scholar
  • 21 Agapitov AV, Haynes WG. Role of endothelin in cardiovascular disease. J Renin Angiotensin Aldosterone Syst 2002; 3: 1-15
    CrossrefPubMedGoogle Scholar
  • 22 Holzhauser L, Zolty R. Endothelin receptor polymorphisms in the cardiovascular system: potential implications for therapy and screening. Heart Fail Rev 2014; 19: 743-758
    CrossrefPubMedGoogle Scholar
  • 23 Mazzuca MQ, Khalil RA. Vascular endothelin receptor type B: structure, function and dysregulation in vascular disease. Biochem Pharmacol 2012; 84: 147-162
    CrossrefPubMedGoogle Scholar
  • 24 Kirkby NS, Hadoke PW, Bagnall AJ, Webb DJ. The endothelin system as a therapeutic target in cardiovascular disease: great expectations or bleak house. Br J Pharmacol 2008; 153: 1105-1119
    PubMedGoogle Scholar
  • 25 Moorhouse RC, Webb DJ, Kluth DC, Dhaun N. Endothelin antagonism and its role in the treatment of hypertension. Curr Hypertens Rep 2013; 15: 489-496
    CrossrefPubMedGoogle Scholar
  • 26 Gray GA, Webb D. The endothelin system and its potential as a therapeutic target in cardiovascular disease. Pharmacol Ther 1996; 72: 109-148
    CrossrefPubMedGoogle Scholar
  • 27 McMahon EG, Palomo MA, Moore WM. Phosphoramidon blocks the pressor activity of big endothelin[1–39] and lowers blood pressure in spontaneously hypertensive rats. J Cardiovasc Pharmacol 1991; 17: 29-33
    PubMedGoogle Scholar
  • 28 Martínez-Miguel P, Medrano-Andrés D, Lopes-Martín V, Arribas-Gómez I, Rodríguez-Puyol M, Rodríguez-Puyol D, López-Ongil S. Regulation of endothelin-converting enzyme-1 (ECE-1) by the calcimimetic R-568. Pharmacol Res 2013; 76: 106-118
    CrossrefPubMedGoogle Scholar
  • 29 Habib GB, Basra SS. Are there any new pharmacologic therapies on the horizon to better treat hypertension: a state-of-the-art paper. J Cardiovasc Pharmacol Ther 2014; 19: 516-525
    CrossrefPubMedGoogle Scholar
  • 30 Strachan E, Spratt C, Wilkinson B, Johnston R, Gray G, Webb J. Systemic blockade of the endothelin-B receptor increases peripheral vascular resistance in healthy men. Hypertension 1999; 33: 581-585
    CrossrefPubMedGoogle Scholar
  • 31 Nakamura H, Kobayashi J, Kobayashi M, Ohizumi Y, Hirata Y. Xestoquinone. A novel cardiotonic marine natural product isolated from the Okinawan sea sponge Xestospongia sapra . Chem Letters 1985; 6: 713-716
    PubMedGoogle Scholar
  • 32 Zhu HB, Geng MY, Guan HS, Zhang JT. Antihypertensive effects of D-polymannuronic sulfate and its related mechanisms in renovascular hypertensive rats. Acta Pharmacol Sin 2000; 21: 727-732
    PubMedGoogle Scholar
  • 33 Endo M, Nakagawa W, Hamamoto Y, Ishihama M. Pharmacologically active substances from southern pacific marine invertebrates. Pure Appl Chem 1986; 58: 387-394
    PubMedGoogle Scholar
  • 34 Kaul PN. Biomedical potencial of the sea. Pure Appl Chem 1982; 54: 1963-1972
    PubMedGoogle Scholar
  • 35 Anastasi A, Erspamer V. The isolation and amino acid sequence of eledoisin, the active endecapeptide of the posterior salivary glands of Eledone . Arch Biochem Biophys 1963; 101: 56-65
    CrossrefPubMedGoogle Scholar
  • 36 Ihara M, Fukuroda T, Saeki T, Nishikibe M, Kojiri K, Suda H, Yano M. An endothelin receptor (ETA) antagonist isolated from Streptomyces misakiensis . Biochem Biophys Res Commun 1991; 178: 132-137
    CrossrefPubMedGoogle Scholar
  • 37 Ihara M, Ishikawa K, Fukuroda T, Saeki T, Funabashi K, Fukami T, Suda H, Yano M. In vitro biological profile of a highly potent novel endothelin (ET) antagonist BQ-123 selective for the ETA receptor. J Cardiovasc Pharmacol 1992; 20 (Suppl. 12) S11-S14
    PubMedGoogle Scholar
  • 38 Miyata S, Ohhata N, Murai H, Masui Y, Ezaki M, Takase S, Nishikawa M, Kiyoto S, Okuhara M, Kohsaka M. WS009 A and B, new endothelin receptor antagonists isolated from Streptomyces sp. No. 89009. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo) 1992; 45: 1029-1040
    CrossrefPubMedGoogle Scholar
  • 39 Takaishi S, Tuchiya N, Sato A, Negishi T, Takamatsu Y, Matsushita Y, Watanabe T, Iijima Y, Haruyama H, Kinoshita T, Tanaka M, Kodama K. B-90063, a novel endothelin converting enzyme inhibitor isolated from a new marine bacterium, Blastobacter sp. SANK 71894. J Antibiot (Tokyo) 1998; 51: 805-815
    CrossrefPubMedGoogle Scholar
  • 40 Tsurumi Y, Fujie K, Nishikawa M, Kiyoto S, Okuhara M. Biological and pharmacological properties of highly selective new endothelin converting enzyme inhibitor WS79089B isolated from Streptosporangium roseum No. 79089. J Antibiot (Tokyo) 1995; 48: 169-174
    CrossrefPubMedGoogle Scholar
  • 41 Nakamura M, Ito Y, Ogawa K, Michisuji Y, Sato S, Takada M, Hayashi M, Yaginuma S, Yamamoto S. Stachybocins, novel endothelin receptor antagonists, produced by Stachybotrys sp. M6222. I. Taxonomy, fermentation, isolation and characterization. J Antibiot (Tokyo) 1995; 48: 1389-1395
    CrossrefPubMedGoogle Scholar
  • 42 Wu B, Oesker V, Wiese J, Malien S, Schmaljohann R, Imhoff JF. Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347. Mar Drugs 2014; 12: 1924-1938
    CrossrefPubMedGoogle Scholar
  • 43 Zhou H, Zhu T, Cai S, Gu Q, Li D. Drimane sesquiterpenoids from the mangrove-derived fungus Aspergillus ustus . Chem Pharm Bull (Tokyo) 2011; 59: 762-766
    CrossrefPubMedGoogle Scholar
  • 44 Liu H, Edrada-Ebel R, Ebel R, Wang Y, Schulz B, Draeger S, Müller WE, Wray V, Lin W, Proksch P. Drimane sesquiterpenoids from the fungus Aspergillus ustus isolated from the marine sponge Suberites domuncula . J Nat Prod 2009; 72: 1585-1588
    CrossrefPubMedGoogle Scholar
  • 45 Roggo BE, Petersen F, Sills M, Roesel JL, Moerker T, Peter HH. Novel spirodihydrobenzofuranlactams as antagonists of endothelin and as inhibitors of HIV-1 protease produced by Stachybotrys sp. I. Fermentation, isolation and biological activity. J Antibiot (Tokyo) 1996; 49: 13-19
    CrossrefPubMedGoogle Scholar
  • 46 Ogawa T, Ando K, Tanaka T, Uosaki Y, Matsuda Y. RES-1149-1 and − 2, novel non-peptidic endothelin type B receptor antagonists produced by Aspergillus sp. I. Taxonomy of producing strain, fermentation, isolation, and physico-chemical and biological properties. J Antibiot (Tokyo) 1996; 49: 1-5
    CrossrefPubMedGoogle Scholar
  • 47 Hayes MA, Wrigley SK, Chetland I, Reynolds EE, Ainsworth AM, Renno DV, Latif MA, Cheng XM, Hupe DJ, Charlton P, Doherty AM. Novel drimane sesquiterpene esters from Aspergillus ustus var. pseudodeflectus with endothelin receptor binding activity. J Antibiot (Tokyo) 1996; 49: 505-512
    CrossrefPubMedGoogle Scholar
  • 48 Li J, Yang X, Lin Y, Yuan J, Lu Y, Zhu X, Li J, Li M, Lin Y, He J, Liu L. Meroterpenes and azaphilones from marine mangrove endophytic fungus Penicillium 303#. Fitoterapia 2014; 97: 241-246
    CrossrefPubMedGoogle Scholar
  • 49 Yamada T, Jinno M, Kikuchi T, Kajimoto T, Numata A, Tanaka R. Three new azaphilones produced by a marine fish-derived Chaetomium globosum . J Antibiot (Tokyo) 2012; 65: 413-417
    CrossrefPubMedGoogle Scholar
  • 50 Gao SS, Li XM, Zhang Y, Li CS, Cui CM, Wang BG. Comazaphilones A–F, azaphilone derivatives from the marine sediment-derived fungus Penicillium commune QSD-17. J Nat Prod 2011; 74: 256-261
    CrossrefPubMedGoogle Scholar
  • 51 Ogawa T, Ando K, Aotani Y, Shinoda K, Tanaka T, Tsukuda E, Yoshida M, Matsuda Y. RES-1214-1 and -2, novel non-peptidic endothelin type A receptor antagonists produced by Pestalotiopsis sp . J Antibiot (Tokyo) 1995; 48: 1401-1406
    CrossrefPubMedGoogle Scholar
  • 52 Proksch P, Ebel R, Edrada RA, Wray V, Steube K. Bioactive natural products from marine invertebrates and associated fungi. Prog Mol Subcell Biol 2003; 37: 117-142
    PubMedGoogle Scholar
  • 53 Patil A, Freyer A, Breen A, Carte B, Johnson R. Halistanol disulfate B, a novel sulfate sterol from sponge Pachastrella sp.: inhibitor of endothelin converting enzyme. J Nat Prod 1996; 59: 606-608
    CrossrefPubMedGoogle Scholar
  • 54 Gershenzon J, Dudareva N. The function of terpene natural products in the natural world. Nat Chem Biol 2007; 3: 408-414
    CrossrefPubMedGoogle Scholar
  • 55 Latek D, Modzelewska A, Trzaskowski B, Palczewski K, Filipek S. G protein-coupled receptors-recent advances. Acta Biochim Pol 2012; 59: 515-529
    PubMedGoogle Scholar
  • 56 Pin JP, Galvez T, Prézeau L. Evolution, structure, and activation mechanism of family 3/C G-protein-coupled receptors. Pharmacol Ther 2003; 98: 325-354
    CrossrefPubMedGoogle Scholar
  • 57 Senni K, Pereira J, Gueniche F, Delbarre-Ladrat C, Sinquin C, Ratiskol J, Godeau G, Fischer AM, Helley D, Colliec-Jouault S. Marine polysaccharides: a source of bioactive molecules for cell therapy and tissue engineering. Mar Drugs 2011; 9: 1664-1681
    CrossrefPubMedGoogle Scholar
  • 58 Conibear AC, Craik DJ. The chemistry and biology of theta defensins. Angew Chem Int Ed Engl 2014; 53: 10612-10623
    CrossrefPubMedGoogle Scholar
  • 59 Sjögren M, Jonsson PR, Dahlström M, Lundälv T, Burman R, Göransson U, Bohlin L. Two brominated cyclic dipeptides released by the coldwater marine sponge Geodia barretti act in synergy as chemical defense. J Nat Prod 2011; 74: 449-454
    CrossrefPubMedGoogle Scholar
  • 60 Xiong Z, Wang J, Hao J, Wang Y. Recent advances in the discovery and development of marine microbial natural products. Mar Drugs 2013; 11: 700-717
    CrossrefPubMedGoogle Scholar