Understanding hypocholesterolemic activity of soy isoflavones: Completing the puzzle through computational simulations

References

• Atho'illah, M. F., Safitri, Y. D., Nur’aini, F. D., Savitri, R. U., Rahayu, S., Widyarti, S., & Rifa'i, M. (2019). Evaluation of glyceollin accumulation and antioxidant properties on soybean (Glycine max L.) through combination of different biotic elicitor and light. Scientific Study & Research Chemistry & Chemical Engineering, Biotechnology, Food Industry 20, 199–208. https://doi.org/10.13140/RG.2.2.19614.28483
   Google Scholar
• Banerjee, P., Eckert, A. O., Schrey, A. K., & Preissner, R. (2018). ProTox-II: A webserver for the prediction of toxicity of chemicals. Nucleic Acids Research, 46(W1), W257–W263. https://doi.org/10.1093/nar/gky318
   PubMed Web of Science ®Google Scholar
• Boucher, P., & Vogel, H. G. (2016). Inhibition of cholesterol biosynthesis. In F. J. Hock (Ed.), Drug discovery and evaluation: Pharmacological assays (pp. 2247–2271). Springer International Publishing.
   Google Scholar
• Dallakyan, S., & Olson, A. J. (2015). Small-molecule library screening by docking with PyRx. Methods in molecular biology (Clifton, N.J.), 1263, 243–250. https://doi.org/10.1007/978-1-4939-2269-7_19
   PubMedGoogle Scholar
• Fu, Y., Zhao, J., & Chen, Z. (2018). Insights into the molecular mechanisms of protein-ligand interactions by molecular docking and molecular dynamics simulation: A case of oligopeptide binding protein. Computational and Mathematical Methods in Medicine, 2018, 3502514. https://doi.org/10.1155/2018/3502514
   PubMed Web of Science ®Google Scholar
• Goldstein, J. L., & Brown, M. S. (2009). History of discovery: The LDL receptor. Arteriosclerosis, Thrombosis, and Vascular Biology, 29(4), 431–438. https://doi.org/10.1161/ATVBAHA.108.179564
   PubMed Web of Science ®Google Scholar
• Gustafsen, C., Olsen, D., Vilstrup, J., Lund, S., Reinhardt, A., Wellner, N., Larsen, T., Andersen, C. B. F., Weyer, K., Li, J., Seeberger, P. H., Thirup, S., Madsen, P., & Glerup, S. (2017). Heparan sulfate proteoglycans present PCSK9 to the LDL receptor. Nature Communications, 8(1), 503. https://doi.org/10.1038/s41467-017-00568-7
   PubMedGoogle Scholar
• Herwana, E., Pusparini, P., & Graciela, A. (2020). High dietary daidzein intake lowers cholesterol levels among post-menopausal women. Universa Med, 39(1), 47–54. https://doi.org/10.18051/UnivMed.2020.v39.47-54
   Web of Science ®Google Scholar
• Huang, H., Xie, Z., Boue, S. M., Bhatnagar, D., Yokoyama, W., Yu, L. L., & Wang, T. T. Y. (2013). Cholesterol-lowering activity of soy-derived glyceollins in the golden Syrian hamster model. Journal of Agricultural and Food Chemistry, 61(24), 5772–5782. https://doi.org/10.1021/jf400557p
   PubMed Web of Science ®Google Scholar
• Istvan, E. S., Palnitkar, M., Buchanan, S. K., & Deisenhofer, J. (2000). Crystal structure of the catalytic portion of human HMG-CoA reductase: Insights into regulation of activity and catalysis. The EMBO Journal, 19(5), 819–830. https://doi.org/10.1093/emboj/19.5.819
   PubMed Web of Science ®Google Scholar
• Krieger, E., & Vriend, G. (2015). New ways to boost molecular dynamics simulations. Journal of Computational Chemistry, 36(13), 996–1007. https://doi.org/10.1002/jcc.23899
   PubMed Web of Science ®Google Scholar
• Lee, S.-O., Renouf, M., Ye, Z., Murphy, P. A., & Hendrich, S. (2007). Isoflavone glycitein diminished plasma cholesterol in female golden Syrian hamsters. Journal of Agricultural and Food Chemistry, 55(26), 11063–11067. https://doi.org/10.1021/jf070972r
   PubMed Web of Science ®Google Scholar
• Lee, S. J., Sekimoto, T., Yamashita, E., Nagoshi, E., Nakagawa, A., Imamoto, N., Yoshimura, M., Sakai, H., Chong, K. T., Tsukihara, T., & Yoneda, Y. (2003). The structure of importin-beta bound to SREBP-2: Nuclear import of a transcription factor. Science (New York, N.Y.), 302(5650), 1571–1575. https://doi.org/10.1126/science.1088372
   PubMed Web of Science ®Google Scholar
• Lewandowski, W., Lewandowska, H., Golonko, A., Świderski, G., Świsłocka, R., & Kalinowska, M. (2020). Correlations between molecular structure and biological activity in “logical series” of dietary chromone derivatives. PLoS ONE, 15(8), e0229477. https://doi.org/10.1371/journal.pone.0229477
   PubMed Web of Science ®Google Scholar
• Lu, R., Zheng, Z., Yin, Y., & Jiang, Z. (2019). Effect of Genistein on cholesterol metabolism-related genes in HepG2 cell. Journal of Food Science, 84(8), 2330–2336. https://doi.org/10.1111/1750-3841.14725
   PubMed Web of Science ®Google Scholar
• Ma, S., Sun, W., Gao, L., & Liu, S. (2019). Therapeutic targets of hypercholesterolemia: HMGCR and LDLR. Diabetes, Metabolic Syndrome and Obesity : targets and Therapy, 12, 1543–1553. https://doi.org/10.2147/DMSO.S219013
   PubMed Web of Science ®Google Scholar
• Maier, J. A., Martinez, C., Kasavajhala, K., Wickstrom, L., Hauser, K. E., & Simmerling, C. (2015). ff14SB: Improving the accuracy of protein side chain and backbone parameters from ff99SB. Journal of Chemical Theory and Computation, 11(8), 3696–3713. https://doi.org/10.1021/acs.jctc.5b00255
   PubMed Web of Science ®Google Scholar
• Mannino, G., Iovino, P., Lauria, A., Genova, T., Asteggiano, A., Notarbartolo, M., Porcu, A., Serio, G., Chinigò, G., Occhipinti, A., Capuzzo, A., Medana, C., Munaron, L., & Gentile, C. (2021). Bioactive triterpenes of protium heptaphyllum gum resin extract display cholesterol-lowering potential. International Journal of Molecular Sciences, 22(5), 2664. https://doi.org/10.3390/ijms22052664
   PubMed Web of Science ®Google Scholar
• Mannu, G. S., Zaman, M. J. S., Gupta, A., Rehman, H. U., & Myint, P. K. (2013). Evidence of lifestyle modification in the management of hypercholesterolemia. Current Cardiology Reviews, 9(1), 2–14. https://doi.org/10.2174/157340313805076313
   PubMedGoogle Scholar
• Mansouri, A., Vahdati, A., Nematbakhsh, M., & Moshtaghian, J. (2021). Hypercholesterolemia role of vitamin D3 and genistein effect in reducing atherosclerosis in rat. Hormozgan Med J, 19, 306–314.
   Google Scholar
• Marahatha, R., Basnet, S., Bhattarai, B. R., Budhathoki, P., Aryal, B., Adhikari, B., Lamichhane, G., Poudel, D. K., & Parajuli, N. (2021). Potential natural inhibitors of xanthine oxidase and HMG-CoA reductase in cholesterol regulation: In silico analysis. BMC Complementary Medicine and Therapies, 21(1), 1. https://doi.org/10.1186/s12906-020-03162-5
   PubMedGoogle Scholar
• Mezei, O., Banz, W. J., Steger, R. W., Peluso, M. R., Winters, T. A., & Shay, N. (2003). Soy Isoflavones exert antidiabetic and hypolipidemic effects through the PPAR Pathways in obese zucker rats and murine RAW 264.7 cells. The Journal of Nutrition, 133(5), 1238–1243. https://doi.org/10.1093/jn/133.5.1238
   PubMed Web of Science ®Google Scholar
• 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. https://doi.org/10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• 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. J Comput Chem 19:1639–1662. https://doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
   Google Scholar
• Mullen, E., Brown, R. M., Osborne, T. F., & Shay, N. F. (2004). Soy Isoflavones Affect sterol regulatory element binding proteins (SREBPs) and SREBP-regulated genes in HepG2 cells. The Journal of Nutrition, 134(11), 2942–2947. https://doi.org/10.1093/jn/134.11.2942
   PubMed Web of Science ®Google Scholar
• Notarnicola, M., Messa, C., Orlando, A., D'Attoma, B., Tutino, V., Rivizzigno, R., & Caruso, M. G. (2008). Effect of genistein on cholesterol metabolism-related genes in a colon cancer cell line. Genes & Nutrition, 3(1), 35–40. https://doi.org/10.1007/s12263-008-0082-5
   PubMed Web of Science ®Google Scholar
• 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. https://doi.org/10.1371/journal.pone.0012029
   PubMed Web of Science ®Google Scholar
• Ramdath, D. D., Padhi, E. M. T., Sarfaraz, S., Renwick, S., & Duncan, A. M. (2017). Beyond the cholesterol-lowering effect of soy protein: A review of the effects of dietary soy and its constituents on risk factors for cardiovascular disease. Nutrients, 9(4), 324. https://doi.org/10.3390/nu9040324
   PubMed Web of Science ®Google Scholar
• Sirtori, C. R., Lovati, M. R., Manzoni, C., Monetti, M., Pazzucconi, F., & Gatti, E. (1995). Soy and cholesterol reduction: Clinical experience. The Journal of Nutrition, 125(3 Suppl), 598S–605S. https://doi.org/10.1093/jn/125.suppl_3.598S
   PubMed Web of Science ®Google Scholar
• Soran, H., Adam, S., Mohammad, J. B., Ho, J. H., Schofield, J. D., Kwok, S., Siahmansur, T., Liu, Y., Syed, A. A., Dhage, S. S., Stefanutti, C., Donn, R., Malik, R. A., Banach, M., & Durrington, P. N. (2018). Hypercholesterolaemia – practical information for non-specialists. Archives of Medical Science : AMS, 14(1), 1–21. https://doi.org/10.5114/aoms.2018.72238
   PubMed Web of Science ®Google Scholar
• Sung, J. H., Lee, S.-J., Park, K. H., & Moon, T. W. (2004). Isoflavones inhibit 3-hydroxy-3-methylglutaryl coenzyme a reductase in vitro. Bioscience, Biotechnology, and Biochemistry, 68(2), 428–432. https://doi.org/10.1271/bbb.68.428
   PubMed Web of Science ®Google Scholar
• Taddei, C., Zhou, B., Bixby, H., Carrillo-Larco, R. M., Danaei, G., Jackson, R. T., Farzadfar, F., Sophiea, M. K., Di Cesare, M., Iurilli, M. L. C., Martinez, A. R., Asghari, G., Dhana, K., Gulayin, P., Kakarmath, S., Santero, M., Voortman, T., Riley, L. M., Cowan, M. J., … Ezzati, M. (2020). Repositioning of the global epicentre of non-optimal cholesterol. Nature, 582(7810), 73–77. https://doi.org/10.1038/s41586-020-2338-1
   PubMed Web of Science ®Google Scholar
• Taku, K., Umegaki, K., Sato, Y., Taki, Y., Endoh, K., & Watanabe, S. (2007). Soy isoflavones lower serum total and LDL cholesterol in humans: a meta-analysis of 11 randomized controlled trials. The American Journal of Clinical Nutrition, 85(4), 1148–1156. https://doi.org/10.1093/ajcn/85.4.1148
   PubMed Web of Science ®Google Scholar
• Tang, J.-J., Li, J.-G., Qi, W., Qiu, W.-W., Li, P.-S., Li, B.-L., & Song, B.-L. (2011). Inhibition of SREBP by a small molecule, betulin, improves hyperlipidemia and insulin resistance and reduces atherosclerotic plaques. Cell Metabolism, 13(1), 44–56. https://doi.org/10.1016/j.cmet.2010.12.004
   PubMed Web of Science ®Google Scholar
• Teixeira Damasceno, N. R., Apolinário, E., Dias Flauzino, F., Fernandes, I., & Abdalla, D. S. P. (2007). Soy isoflavones reduce electronegative low-density lipoprotein (LDL(-)) and anti-LDL (-) autoantibodies in experimental atherosclerosis. European Journal of Nutrition, 46(3), 125–132. https://doi.org/10.1007/s00394-006-0640-9
   PubMed Web of Science ®Google Scholar
• Wang, Q., Ge, X., Tian, X., Zhang, Y., Zhang, J., & Zhang, P. (2013). Soy isoflavone: The multipurpose phytochemical (Review). Biomedical Reports, 1(5), 697–701. https://doi.org/10.3892/br.2013.129
   PubMedGoogle Scholar
• Wong, W. W., Smith, E. O., Stuff, J. E., Hachey, D. L., Heird, W. C., & Pownell, H. J. (1998). Cholesterol-lowering effect of soy protein in normocholesterolemic and hypercholesterolemic men. The American Journal of Clinical Nutrition, 68(6 Suppl), 1385S–1389S. https://doi.org/10.1093/ajcn/68.6.1385S
   PubMed Web of Science ®Google Scholar
• Zárate, A., Manuel-Apolinar, L., Saucedo, R., Hernández-Valencia, M., & Basurto, L. (2016). Hypercholesterolemia as a risk factor for cardiovascular disease: Current controversial therapeutic management. Archives of Medical Research, 47(7), 491–495. https://doi.org/10.1016/j.arcmed.2016.11.009
   PubMed Web of Science ®Google Scholar