187
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Alpha-cadinol as a potential ACE-inhibitory volatile compound identified from Phaseolus vulgaris L. through in vitro and in silico analysis

, & ORCID Icon
Pages 3847-3861 | Received 22 Nov 2021, Accepted 20 Mar 2022, Published online: 05 Apr 2022

References

  • Abraham, M. J., Murtola, T., Schulz, R., Páll, S., Smith, J., Hess, B., & Lindahl, E. (2015). GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX, 1-2, 19–25. https://doi.org/10.1016/j.softx.2015.06.001
  • Aguiar, J., Gonçalves, J. L., Alves, V. L., & Câmara, J. S. (2021). Relationship between Volatile composition and bioactive potential of vegetables and fruits of regular consumption—An integrative approach. Molecules, 26(12), 3653. https://doi.org/10.3390/molecules26123653
  • Amadei, A., Linssen, A. B., & Berendsen, H. J. (1993). Essential dynamics of proteins. Proteins, 17(4), 412–425.https://doi.org/10.1002/prot.340170408.PMID:8108382.
  • Bayan, L., Koulivand, P. H., & Gorji, A. (2014). Garlic: a review of potential therapeutic effects. Avicenna J. Phytomedicine, 4(1), 1–14.
  • Berendsen, H. J. C., Postma, J. P. M., van Gunsteren, W. F., & Hermans, J. (1981). Interaction models for water in relation to protein hydration. In Pullman B. (Eds.), Intermolecular Forces. The Jerusalem Symposia on Quantum Chemistry and Biochemistry. Vol. 14. Springer. https://doi.org/10.1007/978-94-015-7658-1_21
  • Bussi, G., Donadio, D., & Parrinello, M. (2007). Canonical sampling through velocity rescaling. The Journal of Chemical Physics, 126(1), 014101. https://doi.org/10.1063/1.2408420
  • Caballero, J. (2020). Considerations for docking of selective angiotensin-converting enzyme inhibitors. Molecules, 25(2), 295. https://doi.org/10.3390/molecules25020295
  • Cosconati, S., Forli, S., Perryman, A. L., Harris, R., Goodsell, D. S., & Olson, A. J. (2010). Virtual screening with AutoDock: theory and practice. Expert Opinion on Drug Discovery, 5(6), 597–607.
  • Del Rio, D., Rodriguez-Mateos, A., Spencer, J., Tognolini, M., Borges, G., & Crozier, A. (2013). Dietary (poly)phenolics in human health: Structures, bioavailability, and evidence of protective effects against chronic diseases. Antioxidants & Redox Signaling, 18(14), 1818–1892. https://doi.org/10.1089/ars.2012.4581
  • Durán-Iturbide, N. A., Díaz-Eufracio, B. I., & Medina-Franco, J. L. (2020). In silico ADME/Tox profiling of natural products: A focus on BIOFACQUIM. ACS Omega, 5(26), 16076–16084. https://doi.org/10.1021/acsomega.0c01581
  • Ehlers, M. R., & Riordan, J. F. (1989). Angiotensin-converting enzyme: New concepts concerning its biological role. Biochemistry, 28(13), 5311–5318.
  • Fang, L., Geng, M., Liu, C., Wang, J., Min, W., & Liu, J. (2019). Structural and molecular basis of angiotensin-converting enzyme by computational modeling: Insights into the mechanisms of different inhibitors. PloS One, 14(4), e0215609. https://doi.org/10.1371/journal.pone.0215609
  • Ferreira de Freitas, R., & Schapira, M. (2017). A systematic analysis of atomic protein-ligand interactions in the PDB. MedChemComm, 8(10), 1970–1981. https://doi.org/10.1039/c7md00381a
  • Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., & Mainz, D. T. (2006). Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. Journal of Medicinal Chemistry, 49(21), 6177–6196.https://doi.org/10.1021/jm051256o
  • Fuhrmann, J., Rurainski, A., Lenhof, H. P., & Neumann, D. (2010). A new Lamarckian genetic algorithm for flexible ligand-receptor docking. Journal of Computational Chemistry, 31(9), 1911–1918.https://doi.org/10.1002/jcc.21478.PMID:20082382
  • Gassia, J. P., Durand, D., & Ton That, H. (1980). Long Term Effect of Captopril in Hypertension with Chronic Renal Failure. Proceedings of the European Dialysis and Transplant Association, 17, 719–724.
  • Genheden, S., & Ryde, U. (2015). The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities. Expert Opinion on Drug Discovery, 10(5), 449–461.https://doi.org/10.1517/17460441.2015.1032936.
  • Guerrero, L., Castillo, J., Quiñones, M., Garcia-Vallvé, S., Arola, L., Pujadas, G., & Muguerza, B. (2012). Inhibition of angiotensin-converting enzyme activity by flavonoids: Structure-activity relationship studies. PloS One, 7(11), e49493. https://doi.org/10.1371/journal.pone.0049493
  • Guimarães, A. C., Meireles, L. M., Lemos, M. F., Guimarães, M. C. C., Endringer, D. C., Fronza, M., & Scherer, R. (2019). Antibacterial activity of terpenes and terpenoids present in essential oils. Molecules, 24(13), 2471. https://doi.org/10.3390/molecules24132471
  • Hanif, K., Bid, H., & Konwar, R. (2010). Reinventing the ACE inhibitors: Some old and new implications of ACE inhibition. Hypertension Research: Official Journal of the Japanese Society of Hypertension, 33(1), 11–21. https://doi.org/10.1038/hr.2009.184
  • Hess, B., Bekker, H., Berendsen, H. J., & Fraaije, J. G. (1997). LINCS: A linear constraint solver for molecular simulations. Journal of Computational Chemistry, 18(12), 1463–1472. https://doi.org/10.1002/(SICI)1096-987X(199709)18:12<1463::AID-JCC4>3.0.CO;2-H
  • Ho, C. L., Liao, P. C., Wang, E. I., & Su, Y. C. (2011). Composition and antimicrobial activity of the leaf and twig oils of Litsea acutivena from Taiwan. Natural Product Communications, 6(11), 1755–1758.
  • Huang, J., & MacKerell, A. (2013). CHARMM36 all-atom additive protein force field: Validation based on comparison to NMR data. Journal of Computational Chemistry, 34(25), 2135–2145.
  • Iwalokun, B. A., Hodonu, S. A., Nwoke, S., Ojo, O., & Agomo, P. U. (2011). Evaluation of the possible mechanisms of antihypertensive activity of Loranthus micranthus: An African mistletoe. Biochemistry Research International, 2011, 159439. https://doi.org/10.1155/2011/159439
  • Kumari, R., Kumar, R., & Lynn, A., Open Source Drug Discovery Consortium. (2014). g_mmpbsa-a GROMACS tool for high-throughput MM-PBSA calculations . Journal of Chemical Information and Modeling, 54(7), 1951–1962.https://doi.org/10.1021/ci500020m.
  • Lahlou, S., Interaminense, L. F., Leal-Cardoso, J. H., & Duarte, G. P. (2003). Antihypertensive effects of the essential oil of Alpinia zerumbet and its main constituent, terpinen-4-ol, in DOCA-salt hypertensive conscious rats. Fundamental & Clinical Pharmacology, 17(3), 323–330.https://doi.org/10.1046/j.1472-8206.2003.00150.x.
  • Lasekan, O., & Azeez, S. (2014). Chemo-preventive activities of common vegetables’ volatile organic compounds (VOCs). Pharmaceutica. Analytica Acta, 5(7), 1000306.
  • Laskowski, R. A., & Swindells, M. B. (2011). LigPlot+: multiple ligand-protein interaction diagrams for drug discovery. Journal of Chemical Information and Modeling, 51(10), 2778–2786.https://doi.org/10.1021/ci200227u. Epub 2011 Oct 5.
  • Li, G. H., Liu, H., Shi, Y. H., & Le, G. W. (2005). Direct spectrophotometric measurement of angiotensin I-converting enzyme inhibitory activity for screening bioactive peptides. Journal of Pharmaceutical and Biomedical Analysis, 37(2), 219–224.
  • Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 46(1–3), 3–26.
  • Liu, K., Watanabe, E., & Kokubo, H. (2017). Exploring the stability of ligand binding modes to proteins by molecular dynamics simulations. Journal of Computer-Aided Molecular Design, 31(2), 201–211. https://doi.org/10.1007/s10822-016-0005-2
  • Maurya, D. K., & Sharma, D. (2020). Evaluation of traditional ayurvedic Kadha for prevention and management of the novel Coronavirus (SARS-CoV-2) using in silico approach. Journal of Biomolecular Structure and Dynamics, 30, 1–16. https://doi.org/10.1080/07391102.2020.1852119
  • Menezes, I. A., Barreto, C. M., Antoniolli, A. R., Santos, M. R., & de Sousa, D. P. (2010). Hypotensive activity of terpenes found in essential oils. Zeitschrift Fur Naturforschung. C, Journal of Biosciences, 65(9–10), 562–566. https://doi.org/10.1515/znc-2010-9-1005
  • Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19(14), 1639–1662. https://doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
  • Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). Autodock4 and AutoDockTools4: automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791.
  • Mu, Y., Nguyen, P. H., & Stock, G. (2004). Energy landscape of a small peptide revelaed by dihedral angle principal component analysis. Proteins: Structure, Function, and Bioinformatics, 58(1), 45–52. 2005. https://doi.org/10.1002/prot.20310
  • Murphey, L., Vaughan, D., & Brown, N. (2003). Contribution of bradykinin to the cardioprotective effects of ACE inhibitors. European Heart Journal Supplements, 5, A37–A41. https://doi.org/10.1016/S1520-765X(03)90062-9
  • Naeem, H., & Hasnain, H. Y. B. (2014). Study on the angiotensin converting enzyme inhibiting properties of the terpenoid extract of (Crataegus monogyna). Afr. J. Food Sci. Res, 2(4), 071–073.
  • Natesh, R., Schwager, S. L., Sturrock, E. D., & Acharya, K. R. (2003). Crystal structure of the human angiotensin-converting enzyme-lisinopril complex. Nature, 421(6922), 551–554.https://doi.org/10.1038/nature01370.
  • Ning, X., Zhang, Y., Yuan, T., Li, Q., Tian, J., Guan, W., Liu, B., Zhang, W., Xu, X., & Zhang, Y. (2018). Enhanced thermostability of glucose oxidase through computer-aided molecular design. International Journal of Molecular Sciences, 19(2), 425. https://doi.org/10.3390/ijms19020425
  • Nosé, S., & Klein, M. L. (1983). Constant pressure molecular dynamics for molecular systems. Molecular Physics, 50(5), 1055–1076. https://doi.org/10.1080/00268978300102851
  • Ogu, C. C., & Maxa, J. L. (2000). Drug interactions due to cytochrome P450. Proceedings (Baylor University. Medical Center), 13(4), 421–423.https://doi.org/10.1080/08998280.2000.11927719.
  • Ondetti, M. A., Williams, N. J., Sabo, E. F., Pluscec, J., Weaver, E. R., & Kocy, O. (1971). Angiotensin-converting enzyme inhibitors from the venom of Bothrops jararaca. Isolation, elucidation of structure, and synthesis. Biochemistry, 10(22), 4033–4403. https://doi.org/10.1021/bi00798a004
  • Parrinello, M., & Rahman, A. (1981). Polymorphic transitions in single crystals: A new molecular dynamics method. Journal of Applied Physics, 52(12), 7182–7190. https://doi.org/10.1063/1.328693
  • Patil, R., Das, S., Stanley, A., Yadav, L., Sudhakar, A., & Varma, A. K. (2010). Optimized hydrophobic interactions and hydrogen bonding at the target-ligand interface leads the pathways of drug-designing. PloS One, 5(8), e12029.
  • Persson, I. (2009). Plant-derived substances and cardiovascular diseases: effects of flavonoids, terpenes, and sterols on angiotensin-converting enzyme and nitric oxide. [PhD Thesis]. Linkoping University. https://doi.org/10.1080/00021369.1985.10867226
  • Phan, T. T. V., Heo, S.-Y., Jung, W.-K., & Yi, M. (2020). Spontaneous hinge-bending motions of angiotensin I converting enzyme: Role in activation and inhibition. Molecules (Basel, Switzerland), 25(6), 1288. https://doi.org/10.3390/molecules25061288
  • Pires, D. E., Blundell, T. L., & Ascher, D. B. (2015). PkCSM: Predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. Journal of Medicinal Chemistry, 58(9), 4066–4072. https://doi.org/10.1021/acs.jmedchem.5b00104
  • Roberts, J. L., & Moreau, R. (2016). Functional properties of spinach (Spinacia oleracea L.) phytochemicals and bioactives. Food & Function, 7(8), 3337–3353.https://doi.org/10.1039/c6fo00051g
  • Salah, K. B., Mahjoub, M. A., Chaumont, J. P., Michel, L., Millet-Clerc, J., Chraeif, I., Ammar, S., Mighri, Z., & Aouni, M. (2006). Chemical composition and in vitro antifungal and antioxidant activity of the essential oil and methanolic extract of Teucrium sauvagei Le Houerou. Natural Product Research, 20(12), 1089–1097.https://doi.org/10.1080/14786410600704748.
  • Salentin, S. (2015). PLIP: Fully automated protein-ligand interaction profiler. Nucleic Acids Research, 43, 443–447. https://doi.org/10.1093/nar/gkv315
  • Schnider, P. (2021). Overview of strategies for solving ADMET challenges., in The Medicinal Chemist's Guide to Solving ADMET Challenges. 1–15. https://doi.org/10.1039/9781788016414-00001, eISBN: 978-1-78801-641-4
  • Seeliger, D., & de Groot, B. L. (2010). Ligand docking and binding site analysis with PyMOL and Autodock/Vina. Journal of Computer-Aided Molecular Design, 24(5), 417–422. https://doi.org/10.1007/s10822-010-9352-6
  • Silva, E. AP., Carvalho, J. S., Guimarães, A. G., Barreto, R. S. S., Santos, M. R. V., Barreto, A. S., & Quintans-Júnior, L. J. (2019). The use of terpenes and derivatives as a new perspective for cardiovascular disease treatment: A patent review (2008–2018). Expert Opinion on Therapeutic Patents, 29(1), 43–53. https://doi.org/10.1080/13543776.2019.1558211
  • Suetsuna, K. (1998). Isolation and characterization of angiotensin I converting enzyme inhibitor dipeptides derived from Allium sativum L (garlic). The Journal of Nutritional Biochemistry, 9(7), 415–419. https://doi.org/10.1016/S0955-2863(98)00036-9
  • Tagliazucchi, D., Martini, S., Bellesia, A., & Conte, A. (2015). Identification of ACE-inhibitory peptides from Phaseolus vulgaris after in vitro gastrointestinal digestion. International Journal of Food Sciences and Nutrition, 66(7), 774–782. https://doi.org/10.3109/09637486.2015
  • Tung, Y. T., Huang, C. C., Ho, S. T., Kuo, Y. H., Lin, C. C., Lin, C. T., & Wu, J. H. (2011). Bioactive phytochemicals of leaf essential oils of Cinnamomum osmophloeum prevent lipopolysaccharide/D-galactosamine (LPS/D-GalN)-induced acute hepatitis in mice. Journal of Agricultural and Food Chemistry, 59(15), 8117–8123. doi:https://doi.org/10.1080/10412905.1999.9712005
  • Wang, E., Sun, H., Wang, J., Wang, Z., Liu, H., Zhang, J., & Hou, T. (2019). End-point binding free energy calculation with MM/PBSA and MM/GBSA: Strategies and applications in drug design. Chemical Reviews, 119(16), 9478–9508. https://doi.org/10.1021/acs.chemrev.9b00055
  • Wang, Q., Wang, Y., & Chen, G. (2016). Influence of secondary-structure folding on the mutually exclusive folding process of GL5/I27 protein: Evidence from molecular dynamics simulations. International Journal of Molecular Sciences, 17(11), 1962. https://doi.org/10.3390/ijms17111962
  • Watermeyer, J. M., Sewell, B. T., Schwager, S. L., Natesh, R., Corradi, H. R., Acharya, K. R., & Sturrock, E. D. (2006). Structure of testis ACE glycosylation mutants and evidence for conserved domain movement. Biochemistry, 45(42), 12654–12663. https://doi.org/10.1021/bi061146z
  • Yang, Y., Marczak, E. D., Usui, H., Kawamura, Y., & Yoshikawa, M. (2016). Antihypertensive properties of spinach leaf protein digests. ACS Publications. https://doi.org/10.1021/jf034551v
  • Yu, D., Wang, C., Song, Y., Zhu, J., & Zhang, X. (2019). Discovery of novel angiotensin-converting enzyme inhibitory peptides from todarodes pacificus and their inhibitory mechanism: In silico and in vitro studies. International Journal of Molecular Sciences, 20(17), 4159. https://doi.org/10.3390/ijms20174159

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.