Flavonoids-rich Orthosiphon stamineus extract as new candidate for angiotensin I-converting enzyme inhibition: A molecular docking study

Molecules

Volumn 21, Issue 11, 2016, Pages

  Shafaei, Armaghan ^a   Khan, Md Shamsuddin Sultan ^a   Aisha, Abdalrahim F A ^a   Majid, Amin Malik Shah Abdul ^a   Hamdan, Mohammad Razak ^b   Mordi, Mohd Nizam ^b   Ismail, Zhari ^a  

^a SCHOOL OF PHARMACEUTICAL SCIENCES   (Malaysia)

^b SCHOOL OF PHYSICS   (Malaysia)

Author keywords

Angiotensin converting enzyme; Flavonoids; HPLC UV; Hypertension; Molecular ducking study

Indexed keywords

ACE PROTEIN, HUMAN; DIPEPTIDYL CARBOXYPEPTIDASE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; FLAVONOID; PLANT EXTRACT;

CHEMISTRY; HUMAN; MOLECULAR DOCKING; ORTHOSIPHON;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; FLAVONOIDS; HUMANS; MOLECULAR DOCKING SIMULATION; ORTHOSIPHON; PEPTIDYL-DIPEPTIDASE A; PLANT EXTRACTS;

EID: 84997270905     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21111500     Document Type: Article

References (52)

1. Kearney, P.M.; Whelton, M.; Reynolds, K.; Muntner, P.; Whelton, P.K.; He, J. Global burden of hypertension: Analysis of worldwide data. Lancet 2005, 365, 217-223.
2. Hartmann, R.; Meisel, H. Food-derived peptides with biological activity: From research to food applications. Curr. Opin. Biotechnol. 2007, 18, 163-169.
3. Mittal, B.V.; Singh, A.K. Hypertension in the developing world: Challenges and opportunities. Am. J. Kidney Dis. 2010, 55, 590-598.
4. Maruthur, N.M.; Wang, N.-Y.; Appel, L.J. Lifestyle interventions reduce coronary heart disease risk results from the premier trial. Circulation 2009, 119, 2026-2031.
5. Coates, D. The angiotensin converting enzyme (ACE). Int. J. Biochem. Cell Biol. 2003, 35, 769-773.
6. Al Shukor, N.; Van Camp, J.; Gonzales, G.B.; Staljanssens, D.; Struijs, K.; Zotti, M.J.; Raes, K.; Smagghe, G. Angiotensin-converting enzyme inhibitory effects by plant phenolic compounds: A study of structure activity relationships. J. Agric. Food Chem. 2013, 61, 11832-11839.
7. Pfeffer, M.A.; Frohlich, E.D. Improvements in clinical outcomes with the use of angiotensin-converting enzyme inhibitors: Cross-fertilization between clinical and basic investigation. Am. J. Physiol. Heart Circ. Physiol. 2006, 291, H2021-H2025.
8. Israili, Z.H.; Hall, W.D. Cough and angioneurotic edema associated with angiotensin-converting enzyme inhibitor therapy: A review of the literature and pathophysiology. Ann. Intern. Med. 1992, 117, 234-242.
9. Opie, L. Ace inhibitors in pregnancy: How to avoid the sting in the tail. S. Afr. Med. J. 1996, 86, 326-327.
10. Nyman, U.; Joshi, P.; Madsen, L.; Pedersen, T.; Pinstrup, M.; Rajasekharan, S.; George, V.; Pushpangadan, P. Ethnomedical information and in vitro screening for angiotensin-converting enzyme inhibition of plants utilized as traditional medicines in gujarat, rajasthan and kerala (india). J. Ethnopharmacol. 1998, 60, 247-263.
11. Park, P.-J.; Je, J.-Y.; Kim, S.-K. Angiotensin i converting enzyme (ace) inhibitory activity of hetero-chitooligosaccharides prepared from partially different deacetylated chitosans. J. Agric. Food Chem. 2003, 51, 4930-4934.
12. Heran, B.S.;Wong, M.M.; Heran, I.K.;Wright, J.M. Blood pressure lowering efficacy of angiotensin converting enzyme (ace) inhibitors for primary hypertension. Cochrane Libr. 2008.
13. Cinq-Mars, C.D.; Li-Chan, E.C. Optimizing angiotensin I-converting enzyme inhibitory activity of pacific hake (merluccius productus) fillet hydrolysate using response surface methodology and ultrafiltration. J. Agric. Food Chem. 2007, 55, 9380-9388.
14. Vercruysse, L.; Van Camp, J.; Smagghe, G. Ace inhibitory peptides derived from enzymatic hydrolysates of animal muscle protein: A review. J. Agric. Food Chem. 2005, 53, 8106-8115.
15. Somova, L.; Nadar, A.; Rammanan, P.; Shode, F. Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension. Phytomedicine 2003, 10, 115-121.
16. Guerrero, L.; Castillo, J.; Quiñones, M.; Garcia-Vallvé, S.; Arola, L.; Pujadas, G.; Muguerza, B. Inhibition of angiotensin-converting enzyme activity by flavonoids: Structure-activity relationship studies. PLoS ONE 2012, 7, e49493.
17. Dong, J.; Xu, X.; Liang, Y.; Head, R.; Bennett, L. Inhibition of angiotensin converting enzyme (ace) activity by polyphenols from tea (Camellia sinensis) and links to processing method. Food Funct. 2011, 2, 310-319.
18. Ojeda, D.; Jiménez-Ferrer, E.; Zamilpa, A.; Herrera-Arellano, A.; Tortoriello, J.; Alvarez, L. Inhibition of angiotensin convertin enzyme (ACE) activity by the anthocyanins delphinidin-and cyanidin-3-O-sambubiosides from Hibiscus sabdariffa. J. Ethnopharmacol. 2010, 127, 7-10.
19. Loizzo, M.R.; Said, A.; Tundis, R.; Rashed, K.; Statti, G.A.; Hufner, A.; Menichini, F. Inhibition of angiotensin converting enzyme (ACE) by flavonoids isolated from Ailanthus excelsa (Roxb) (Simaroubaceae). Phytother. Res. 2007, 21, 32-36.
20. Häckl, L.; Cuttle, G.; Sanches Dovichi, S.; Lima-Landman, M.; Nicolau, M. Inhibition of angiotensin-converting enzyme by quercetin alters the vascular response to bradykinin and angiotensin I. Pharmacology 2002, 65, 182-186.
21. Alam, M.A.; Sernia, C.; Brown, L. Ferulic acid improves cardiovascular and kidney structure and function in hypertensive rats. J. Cardiovasc. Pharmacol. 2013, 61, 240-249.
22. Actis-Goretta, L.; Ottaviani, J.I.; Keen, C.L.; Fraga, C.G. Inhibition of angiotensin converting enzyme (ACE) activity by flavan-3-ols and procyanidins. FEBS Lett. 2003, 555, 597-600.
23. Kwon, E.-K.; Lee, D.-Y.; Lee, H.; Kim, D.-O.; Baek, N.-I.; Kim, Y.-E.; Kim, H.-Y. Flavonoids from the buds of Rosa damascena inhibit the activity of 3-hydroxy-3-methylglutaryl-coenzyme a reductase and angiotensin I-converting enzyme. J. Agric. Food Chem. 2009, 58, 882-886.
24. Bormann, H.; Melzig, M. Inhibition of metallopeptidases by flavonoids and related compounds. Die Pharm. 2000, 55, 129-132.
25. Yesudas, R.; Gumaste, U.; Snyder, R.; Thekkumkara, T. Tannic acid down-regulates the angiotensin type 1 receptor through a mapk-dependent mechanism. Mol. Endocrinol. 2012, 26, 458-470.
26. Balasuriya, B.N.; Rupasinghe, H.V. Plant flavonoids as angiotensin converting enzyme inhibitors in regulation of hypertension. Funct. Foods Health Dis. 2011, 1, 172-188.
27. Quiñones, M.; Sánchez, D.; Muguerza, B.; Miguel, M.; Aleixandre, A. Mechanisms for antihypertensive effect of cocoanox, a polyphenol-rich cocoa powder, in spontaneously hypertensive rats. Food Res. Int. 2011, 44, 1203-1208.
28. Junior, A.G.; Gasparotto, F.M.; Lourenço, E.L.B.; Crestani, S.; Stefanello, M.E.A.; Salvador, M.J.; da Silva-Santos, J.E.; Marques, M.C.A.; Kassuya, C.A.L. Antihypertensive effects of isoquercitrin and extracts from Tropaeolum majus L.: Evidence for the inhibition of angiotensin converting enzyme. J. Ethnopharmacol. 2011, 134, 363-372.
29. Lahogue, V.; Réhel, K.; Taupin, L.; Haras, D.; Allaume, P. A HPLC-UV method for the determination of angiotensin I-converting enzyme (ACE) inhibitory activity. Food Chem. 2010, 118, 870-875.
30. Alves, M.; Araujo, M.d.C.; Juliano, M.A.; Oliveira, E.M.d.; Krieger, J.E.; Casarini, D.E.; Juliano, L.; Carmona, A.K. A continuous fluorescent assay for the determination of plasma and tissue angiotensin I-converting enzyme activity. Braz. J. Med. Biol. Res. 2005, 38, 861-868.
31. Sentandreu, M.Á.; Toldrá, F. A rapid, simple and sensitive fluorescence method for the assay of angiotensin-I converting enzyme. Food Chem. 2006, 97, 546-554.
32. Cushman, D.; Cheung, H. Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung. Biochem. Pharmacol. 1971, 20, 1637-1648.
33. Inoue, K.; Kitade, M.; Hino, T.; Oka, H. Screening assay of angiotensin-converting enzyme inhibitory activity from complex natural colourants and foods using high-throughput LC-MS/MS. Food Chem. 2011, 126, 1909-1915.
34. Miguel, M.; Manso, M.A.; Martín-Álvarez, P.J.; Aleixandre, A.; López-Fandiño, R. Angiotensin-converting enzyme activity in plasma and tissues of spontaneously hypertensive rats after the short-and long-term intake of hydrolysed egg white. Mol. Nutr. Food Res. 2007, 51, 555-563.
35. Mohamed, E.A.H.; Mohamed, A.J.; Asmawi, M.Z.; Sadikun, A.; Ebrika, O.S.; Yam, M.F. Antihyperglycemic effect of orthosiphon stamineus benth leaves extract and its bioassay-guided fractions. Molecules 2011, 16, 3787-3801.
36. Matsubara, T.; Bohgaki, T.; Watarai, M.; Suzuki, H.; Ohashi, K.; Shibuya, H. Antihypertensive actions of methylripariochromene a from Orthosiphon aristatus, an Indonesian traditional medicinal plant. Biol. Pharm. Bull. 1999, 22, 1083-1088.
37. Arafat, O.; Tham, S.; Sadikun, A.; Zhari, I.; Haughton, P.; Asmawi, M. Studies on diuretic and hypouricemic effects of Orthosiphon stamineus methanol extracts in rats. J. Ethnopharmacol. 2008, 118, 354-360.
38. Dolečková, I.; Rárová, L.; Grúz, J.; Vondrusová, M.; Strnad, M.; Kryštof, V. Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves. Fitoterapia 2012, 83, 1000-1007.
39. Akowuah, G.; Zhari, I.; Norhayati, I.; Sadikun, A.; Khamsah, S. Sinensetin, eupatorin, 30-hydroxy-5,6,7,40-tetramethoxyflavone and rosmarinic acid contents and antioxidative effect of Orthosiphon stamineus from Malaysia. Food Chem. 2004, 87, 559-566.
40. Akowuah, G.; Ismail, Z.; Norhayati, I.; Sadikun, A. The effects of different extraction solvents of varying polarities on polyphenols of orthosiphon stamineus and evaluation of the free radical-scavenging activity. Food Chem. 2005, 93, 311-317.
41. Corradini, E.; Foglia, P.; Giansanti, P.; Gubbiotti, R.; Samperi, R.; Laganà, A. Flavonoids: Chemical properties and analytical methodologies of identification and quantitation in foods and plants. Natl. Prod. Res. 2011, 25, 469-495.
42. Hughes, R.J.; Croley, T.R.; Metcalfe, C.D.; March, R.E. A tandem mass spectrometric study of selected characteristic flavonoids. Int. J. Mass Spectrom. 2001, 210, 371-385.
43. Fraga, C.G.; Galleano, M.; Verstraeten, S.V.; Oteiza, P.I. Basic biochemical mechanisms behind the health benefits of polyphenols. Mol. Asp. Med. 2010, 31, 435-445.
44. Navarro-Nunez, L.; Castillo, J.; Lozano, M.L.; Martinez, C.; Benavente-García, O.; Vicente, V.; Rivera, J. Thromboxane a2 receptor antagonism by flavonoids: Structure-activity relationships. J. Agric. Food Chem. 2009, 57, 1589-1594.
45. Benavente-Garcia, O.; Castillo, J.; Lorente, J.; Ortuno, A.; Del Rio, J. Antioxidant activity of phenolics extracted from Olea europaea L. Leaves. Food Chem. 2000, 68, 457-462.
46. Parellada, J.; Suárez, G.; Guinea, M. Inhibition of zinc metallopeptidases by flavonoids and related phenolic compounds: Structure-activity relationships. J. Enzym. Inhib. 1998, 13, 347-359.
47. Ende, C.; Gebhardt, R. Inhibition of matrix metalloproteinase-2 and-9 activities by selected flavonoids. Planta Med. 2004, 70, 1006-1008.
48. Siddiqui, M.J.A.; Ismail, Z. Simultaneous analysis of bioactive markers from Orthosiphon stamineus benth leaves extracts by reverse phase high performance liquid chromatography. Trop. J. Pharm. Res. 2011, 10, 97-103.
49. International Conference on Harmonization. Validation of Analytical Procedures: Methodology (Q2B); FDA: Rockville, MD, USA, 1996.
50. Karamać, M. Chelation of Cu (II), Zn (II), and Fe (II) by tannin constituents of selected edible nuts. Int. J. Mol. Sci. 2009, 10, 5485-5497.
51. Böhm, H.-J. Prediction of binding constants of protein ligands: A fast method for the prioritization of hits obtained from de novo design or 3D database search programs. J. Comput. Aided Mol. Des. 1998, 12, 309-309.
52. Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A fast flexible docking method using an incremental construction algorithm. J. Mol. Biol. 1996, 261, 470-489.