Novel direct factor Xa inhibitory compounds from Tenebrio molitor with anti-platelet aggregation activity

Food and Chemical Toxicology

Volumn 109, Issue , 2017, Pages 19-27

  Lee, Wonhwa ^a   Kim, Mi Ae ^a,b   Park, InWha ^c   Hwang, Jae Sam ^b   Na, MinKyun ^c   Bae, Jong Sup ^a  

^a Kyungpook National University   (South Korea)

^b National Institute of Animal Science   (South Korea)

^c Chungnam National University   (South Korea)

Author keywords

Diketopiperazine; FXa; Phenylethanoid; Platelet aggregation; Tenebrio molitor

Indexed keywords

BLOOD CLOTTING FACTOR 10A; BLOOD CLOTTING FACTOR 10A INHIBITOR; DUAL SPECIFICITY PHOSPHATASE 2; ENDOTHELIN 1; MARCKS PROTEIN; NITRIC OXIDE; PADGEM PROTEIN; PHENYLETHANOID; PIPERAZINEDIONE; PROTEIN KINASE C; RIVAROXABAN; THROMBOPLASTIN; UNCLASSIFIED DRUG; ANTITHROMBOCYTIC AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTICOAGULATION; ARTICLE; BLOOD CLOTTING; BLOOD CLOTTING TIME; CALCIUM MOBILIZATION; CAROTID ARTERY THROMBOSIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFECT; DRUG ISOLATION; DRUG MECHANISM; DRUG PURIFICATION; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC50; LUNG EMBOLISM; MAXIMUM REACTION VELOCITY; MOUSE; NONHUMAN; PARTIAL THROMBOPLASTIN TIME; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; PROTHROMBIN TIME; THROMBOCYTE AGGREGATION INHIBITION; ANIMAL; CHEMISTRY; DRUG EFFECTS; GENETICS; METABOLISM; PHYSIOLOGY; TENEBRIO; THROMBOCYTE; THROMBOCYTE AGGREGATION;

ANIMALS; BLOOD PLATELETS; ENDOTHELIN-1; FACTOR XA; FACTOR XA INHIBITORS; HUMANS; MICE; P-SELECTIN; PLATELET AGGREGATION; PLATELET AGGREGATION INHIBITORS; TENEBRIO;

EID: 85028390212     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2017.08.026     Document Type: Article

References (43)

1. Bauer, K.A., New anticoagulants: anti IIa vs anti Xa–is one better?. J. Thromb. Thrombolysis 21 (2006), 67–72.
2. Bredt, D.S., Snyder, S.H., Nitric oxide: a physiologic messenger molecule. Annu. Rev. Biochem. 63 (1994), 175–195.
3. Chen, M., Ye, X., Ming, X., Chen, Y., Wang, Y., Su, X., Su, W., Kong, Y., A novel direct factor Xa inhibitory peptide with anti-platelet aggregation activity from Agkistrodon acutus venom hydrolysates. Sci. Rep., 5, 2015, 10846.
4. Covas, M.I., Ruiz-Gutierrez, V., de la Torre, R., Kafatos, A., Lamuela-Raventos, R.M., Osada, J., Owen, R.W., Visioli, F., Minor components of olive oil: evidence to date of health benefits in humans. Nutr. Rev. 64 (2006), S20–S30.
5. d'Uscio, L.V., Barton, M., Shaw, S., Luscher, T.F., Endothelin in atherosclerosis: importance of risk factors and therapeutic implications. J. Cardiovasc. Pharmacol. 35 (2000), S55–S59.
6. Dahlback, B., Blood coagulation. Lancet 355 (2000), 1627–1632.
7. Dai, C.H., Ma, H.L., Luo, L., Yin, X.L., Angiotensin I-converting enzyme (ACE) inhibitory peptide derived from Tenebrio molitor (L.) larva protein hydrolysate. Eur. Food Res. Technol. 236 (2013), 681–689.
8. Diehl, K.H., Hull, R., Morton, D., Pfister, R., Rabemampianina, Y., Smith, D., Vidal, J.M., van de Vorstenbosch, C., A good practice guide to the administration of substances and removal of blood, including routes and volumes. J. Appl. Toxicol. 21 (2001), 15–23.
9. Eikelboom, J.W., Hirsh, J., Spencer, F.A., Baglin, T.P., Weitz, J.I., Antiplatelet drugs: antithrombotic therapy and prevention of thrombosis, 9th ed: american college of chest physicians evidence-based clinical practice guidelines. Chest 141 (2012), e89S–119S.
10. Elzagallaai, A., Rose, S.D., Trifaro, J.M., Platelet secretion induced by phorbol esters stimulation is mediated through phosphorylation of MARCKS: a MARCKS-derived peptide blocks MARCKS phosphorylation and serotonin release without affecting pleckstrin phosphorylation. Blood 95 (2000), 894–902.
11. Fares, A., Winter cardiovascular diseases phenomenon. N. Am. J. Med. Sci. 5 (2013), 266–279.
12. Ferraris, V.A., Ferraris, S.P., Saha, S.P., Antiplatelet drugs: mechanisms and risks of bleeding following cardiac operations. Int. J. Angiol. 20 (2011), 1–18.
13. Ghosh, S., Ezban, M., Persson, E., Pendurthi, U., Hedner, U., Rao, L.V., Activity and regulation of factor VIIa analogs with increased potency at the endothelial cell surface. J. Thromb. Haemost. 5 (2007), 336–346.
14. Hahn, B.S., Jo, Y.Y., Yang, K.Y., Wu, S.J., Pyo, M.K., YunChoi, H.S., Kim, Y.S., Evaluation of the in vivo antithrombotic, anticoagulant and fibrinolytic activities of Lumbricus rubellus earthworm powder. Arch. Pharm. Res. 20 (1997), 17–23.
15. Hourani, S.M., Cusack, N.J., Pharmacological receptors on blood platelets. Pharmacol. Rev. 43 (1991), 243–298.
16. Izuhara, Y., Takahashi, S., Nangaku, M., Takizawa, S., Ishida, H., Kurokawa, K., van Ypersele de Strihou, C., Hirayama, N., Miyata, T., Inhibition of plasminogen activator inhibitor-1: its mechanism and effectiveness on coagulation and fibrosis. Arterioscler. Thromb. Vac. Biol. 28 (2008), 672–677.
17. Jauch, E.C., Saver, J.L., Adams, H.P. Jr., Bruno, A., Connors, J.J., Demaerschalk, B.M., Khatri, P., McMullan, P.W. Jr., Qureshi, A.I., Rosenfield, K., Scott, P.A., Summers, D.R., Wang, D.Z., Wintermark, M., Yonas, H., Guidelines for the early management of patients with acute ischemic stroke: a guideline for healthcare professionals from the American Heart Association/American Stroke Association. Stroke 44 (2013), 870–947.
18. Jiang, D., Zhan, B., Mayor, R.S., Gillespie, P., Keegan, B., Bottazzi, M.E., Hotez, P., Ac-AP-12, a novel factor Xa anticoagulant peptide from the esophageal glands of adult Ancylostoma caninum. Mol. Biochem. Parasitol. 177 (2011), 42–48.
19. Kang, H., Ku, S.K., Choi, H., Bae, J.S., Three diketopiperazines from marine-derived bacteria inhibit LPS-induced endothelial inflammatory responses. Bioorg Med. Chem. Lett. 26 (2016), 1873–1876.
20. Lee, W., Lee, J., Kulkarni, R., Kim, M.A., Hwang, J.S., Na, M., Bae, J.S., Antithrombotic and antiplatelet activities of small-molecule alkaloids from Scolopendra subspinipes mutilans. Sci. Rep., 6, 2016, 21956.
21. Li, G., Yu, K., Li, F., Xu, K., Li, J., He, S., Cao, S., Tan, G., Anticancer potential of Hericium erinaceus extracts against human gastrointestinal cancers. J. Ethnopharmacol. 153 (2014), 521–530.
22. Loffredo, L., Perri, L., Violi, F., Myocardial infarction and atrial fibrillation: different impact of anti-IIa vs anti-Xa new oral anticoagulants: a meta-analysis of the interventional trials. Int. J. Cardiol. 178 (2015), 8–9.
23. Malmsten, C.L., Prostaglandins, thromboxanes, and leukotrienes in inflammation. Am. J. Med. 80 (1986), 11–17.
24. Mehnaz, S., Saleem, R.S., Yameen, B., Pianet, I., Schnakenburg, G., Pietraszkiewicz, H., Valeriote, F., Josten, M., Sahl, H.G., Franzblau, S.G., Gross, H., Lahorenoic acids A-C, ortho-dialkyl-substituted aromatic acids from the biocontrol strain Pseudomonas aurantiaca PB-St2. J. Nat. Prod. 76 (2013), 135–141.
25. Merten, M., Thiagarajan, P., P-selectin expression on platelets determines size and stability of platelet aggregates. Circulation 102 (2000), 1931–1936.
26. Moon, H.J., Lee, S.Y., Kurata, S., Natori, S., Lee, B.L., Purification and molecular cloning of cDNA for an inducible antibacterial protein from larvae of the coleopteran, Tenebrio molitor. J. Biochem. 116 (1994), 53–58.
27. Ostrem, J.A., Al-Obeidi, F., Safar, P., Safarova, A., Stringer, S.K., Patek, M., Cross, M.T., Spoonamore, J., LoCascio, J.C., Kasireddy, P., Thorpe, D.S., Sepetov, N., Lebl, M., Wildgoose, P., Strop, P., Discovery of a novel, potent, and specific family of factor Xa inhibitors via combinatorial chemistry. Biochem. (Mosc) 37 (1998), 1053–1059.
28. Perzborn, E., Roehrig, S., Straub, A., Kubitza, D., Mueck, W., Laux, V., Rivaroxaban: a new oral factor Xa inhibitor. Arterioscler. Thromb. Vac. Biol. 30 (2010), 376–381.
29. Philippides, G.J., Loscalzo, J., Potential advantages of direct-acting thrombin inhibitors. Coron. Artery Dis. 7 (1996), 497–507.
30. Ruggeri, Z.M., Platelets in atherothrombosis. Nat. Med. 8 (2002), 1227–1234.
31. Samuelsson, B., Goldyne, M., Granstrom, E., Hamberg, M., Hammarstrom, S., Malmsten, C., Prostaglandins and thromboxanes. Annu. Rev. Biochem. 47 (1978), 997–1029.
32. Schmitz-Spanke, S., Schipke, J.D., Potential role of endothelin-1 and endothelin antagonists in cardiovascular diseases. Basic Res. Cardiol. 95 (2000), 290–298.
33. Shen, R.F., Tai, H.H., Thromboxanes: synthase and receptors. J. Biomed. Sci. 5 (1998), 153–172.
34. Shi, Y.N., Tu, Z.C., Wang, X.L., Yan, Y.M., Fang, P., Zuo, Z.L., Hou, B., Yang, T.H., Cheng, Y.X., Bioactive compounds from the insect Aspongopus chinensis. Bioorg. Med. Chem. Lett. 24 (2014), 5164–5169.
35. Sim, D., Flaumenhaft, R., Furie, B., Interactions of platelets, blood-borne tissue factor, and fibrin during arteriolar thrombus formation in vivo. Microcirculation 12 (2005), 301–311.
36. Takaya, Y., Furukawa, T., Miura, S., Akutagawa, T., Hotta, Y., Ishikawa, N., Niwa, M., Antioxidant constituents in distillation residue of Awamori spirits. J. Agric. Food Chem. 55 (2007), 75–79.
37. Van, H.A., Van, I.J., Harmke, K., Esther, M., Afton, H., Giulia, M., Paul, V., FAO Edible Insects: Future Prospects for Food and Feed Security. 2013, Food and agriculture organization of the united nations, Rome.
38. Verhamme, P., Hoylaerts, M.F., The pivotal role of the endothelium in haemostasis and thrombosis. Acta Clin. Belg 61 (2006), 213–219.
39. Wei, A.H., Schoenwaelder, S.M., Andrews, R.K., Jackson, S.P., New insights into the haemostatic function of platelets. Br. J. Haematol. 147 (2009), 415–430.
40. 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 332 (1988), 411–415.
41. Youn, K., Yun, E.Y., Lee, J., Kim, J.Y., Hwang, J.S., Jeong, W.S., Jun, M., Oleic acid and linoleic acid from Tenebrio molitor larvae inhibit BACE1 activity in vitro: molecular docking studies. J. Med. Food 17 (2014), 284–289.
42. Zhang, H.-Y., Qin, M., Li, F.-C., Laatsch, H., Wang, H.-P., Qin, S., Isolation and identification of metabolites produced by marine streptomyces sp. S007. Nat. Prod. Res. Dev. 23 (2011), 410–414.
43. Zhao, W.Y., Zhu, T.J., Fan, G.T., Liu, H.B., Fang, Y.C., Gu, Q.Q., Zhu, W.M., Three new dioxopiperazine metabolites from a marine-derived fungus Aspergillus fumigatus Fres. Nat. Prod. Res. 24 (2010), 953–957.