Molecular docking studies of Chenopodium album Linn with Lanosterol synthase enzyme
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Abstract
Cardiovascular diseases (CVD) are the major cause of death among people across the globe. Hypercholesterolemia is one of the major contributing factors for CVD. Molecules that bind with Lanosterol synthase enzyme, can be potential drug targets. Statin group of compounds like Simvastatin, cerivastatin, Atorvastatin etc., used for treating hypercholesterolemia have side effects and hence there is a growing demand for plant derived flavonoids. This work focusses on studying the compounds quercetin-3-O-(2??,6??-di-O-?-l-rhamnopyranosyl)-?-d-glucopyranoside, kaempferol-3-O-(2??,6??-di-O-?-l-rhamnopyranosyl)-?-d-glucopyranoside, rutin; quercetin-3-O-?-d-glucopyranoside (Iso quercetin); and kaempferol-3-O-?-d-glucopyranoside (Astragalin) present in Chenopodium album Linn to inhibit Lanosterol synthase. Bioactivity score, drug likeness character was assessed in silico. Based on bioactivity spectrum, it is observed that the molecules are biologically active and the probability of these compounds to be biologically active is ranging from 0.784 to 0.992, suggesting that these compounds are effective for treating hypercholesterolemia. In the molecular docking studies, the compounds binding affinity score was in agreement that the molecules have the potential to be used as an alternative to the statin group of compounds in treating cholesterol.
Article Details
Article Details
Keywords
Bioactivity, Chenopodium album, Hypercholesterolemia, Lanosterol synthase enzyme, Molecular docking
References
Alexander Victor, Anand David , Radhakrishnan A. & Subramani, P. (2016). Overviews of Biological Importance of Quercetin: A Bioactive Flavonoid, Pharmacognosy reviews., 10(20), 84-89. doi:10.4103/0973-7847.194044.
Bajwa AA, Zulfiqar U, Sadia S, Bhowmik P & Chauhan BS. (2019). A global perspective on the biology, impact and management of Chenopodium album and Chenopodium murale: two troublesome agricultural and environmental weeds. Environmental Science and Pollution Research, 26, 5357 – 5371 https://doi.org/10.1007/s11356-018-04104-y.
Cutillo F, DellaGreca M, Gionti M, Previtera L & Zarrelli A. (2006). Phenols and lignans from Chenopodium album. Phytochem Anal. 17(5), 344-349. doi:10.1002/pca.924.
Charles-Schoeman C, Fleischmann R, Davignon J, Schwartz H, Turner SM, Beysen C, Milad M, Hellerstein MK, Luo Z, Kaplan IV, Riese R, Zuckerman A & McInnes IB. (2015). Potential mechanisms leading to the abnormal lipid profile in patients with rheumatoid arthritis versus healthy volunteers and reversal by tofacitinib. Arthritis Rheumatol., 67(3), 616-625. doi: 10.1002/art.38974.
FilimonovD, PoroikovV & Borodina GloriozovaT. (1999). Chemical Similarity Assessment Through Multilevel Neighborhoods of Atoms: Definition and Comparison with the Other Descriptors. J. Chem. Inf. Comput. Sci. 39(8), 666-670.
GoharAA & Elmazar MMA (1997). Isolation of hypotensive flavonoids from Chenopodium species growing in Egypt. Phytother Res., 11, 564–567.
Guedes, I. A, Barret A. M. S, Marinho, Krempser E, Kuenemann MA, Sperandio O, Dardenne L E & Miteva M A. (2021). Machine Learning and Physics-Based Scoring Functions for Drug Discovery. Sci.Rep., 11 (1), 3198-3217. https://doi.org/10.1038/s41598-021-82410-1.
GarnatjeT, Peñuelas J & Vallès, (2017) Ethnobotany, phylogeny, and ‘omics’ for human health and food security. Trends Plant Sci., 22(3), 187–191. DOI: 10.1016/j.tplants.2017.01.001
Guarise M, Borgonovo G, Bassoli A & Ferrante A. (2019). Evaluation of two wild populations of Hedge Mustard (Sisymbrium officinale (L.) Scop.) as a potential leafy vegetable. Horticulturae., 5(1), 13-23, https://doi.org/10.3390/horticulturae5010013
Jamolowicz AI, Chen HY & Panegyres PK (2015). Statins and memory loss: An Australian experience. Australas Med J., 8(3), 73-79. doi: 10.4066/AMJ.2015.2014.
Khan T, Dixit S, Ahmad R, Raza S, Azad I, Joshi S & Khan AR. (2017). Molecular docking, PASS analysis, bioactivity score prediction, synthesis, characterization and biological activity evaluation of a functionalized 2-butanone thiosemicarbazone ligand and its complexes. J.Chem.Biol., 10(3), 91–104. https://doi.org/10.1007/s12154-017-0167-y.
Laghari AH, Memon S, Nelofar A, Khan KM & Yasmin A. (2011). Determination of free phenolic acids and antioxidant activity of methanolic extracts obtained from fruits and leaves of Chenopodiumalbum. Food Chem., 126(4), 1850-1855. doi: 10.1016/j.foodchem.2010.11.165.
Lipinski, Christopher. (2004). Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov. Today Technol., 1(4), 337-341. DOI:10.1016/j.ddtec.2004.11.007
Lee JC, Park BK, Choung S, Kim JM, Joung KH, Lee JH, Kim KS, Kim HJ, Jeong JW, Rhee SD & Ku BJ. (2014). Amelioration of Hypercholesterolemia by an EGFR Tyrosine Kinase Inhibitor in Mice with Liver-Specific Knockout of Mig-6. PLoS ONE 9(12): 1-13. https://doi.org/10.1371/journal.pone.0114782
Morand OH, Aebi JD, Dehmlow H, Ji YH, Gains N, Lengsfeld H & Himber J. (1997). Ro 48-8071, a new 2,3-oxidosqualene: lanosterol cyclase inhibitor lowering plasma cholesterol in hamsters, squirrel monkeys, and minipigs: comparison to simvastatin. Journals of Lipid Research., 38(3), 373-390.
Pala, N.A., Sarkar B.C., Shukla, G, Nakul C Shovik D., Jahangeer AB & Sumit C (2019). Floristic composition and utilization of ethnomedicinal plant species in home gardens of the Eastern Himalaya. J Ethnobiology Ethnomedicine., 15(14), 1-16. https://doi.org/10.1186/s13002-019-0293-4
Santos KB, Guedes IA, Karl ALM & Dardenne LE. (2020). Highly Flexible Ligand Docking: Benchmarking of the DockThor Program on the LEADS-PEP Protein–Peptide Data Set, J.Chem.Inf Model., 60 (2), 667-683. doi: 10.1021/acs.jcim. 9b00905.
Salmerón-ManzanoEsther, Garrido-Cardenas Jose A & Manzano-Agugliaro, Francisco (2020). Worldwide Research Trends on Medicinal Plants. Int. J. Environ. Res. Public Health 17(10) 3376-3396. https://doi.org/10.3390/ijerph17103376
Telford DE, Lipson SM, Barrett PH, Sutherland BG, Edwards JY, Aebi JD, Dehmlow H, Morand OH & Huff MW. (2005). A Novel Inhibitor of Oxidosqualene:Lanosterol Cyclase Inhibits Very Low–
Density Lipoprotein Apolipoprotein B100 (ApoB100) Production and Enhances Low-Density Lipoprotein ApoB100 Catabolism Through Marked Reduction in Hepatic Cholesterol Content. Arteriosclerosis, Thrombosis, and Vascular Biology., 25(12), 2608-
2614. https://doi.org/10.1161/01.ATV.0000189158.2845 5. 94
Thilakavathy Thangasamy, Sivanandane Sittadjody & Randy Burd (2009). Chapter 27 - Quercetin: A Potential Complementary and Alternative Cancer Therapy, Complementary and Alternative Therapies and the Aging Population, Academic Press., 563-584. https://doi.org/10.1016/B978-0-12-374228-5.00027-5.
Vanessa Sales de Oliveira, Fernanda Silva Ferreira, Maria Clara Ramos Cople, Tatiana da Silva Labre, Ivanilda Maria Augusta, Ormindo Domingues Gamallo &Tatiana Saldanha (2018), Use of Natural Antioxidants in the Inhibition of Cholesterol Oxidation: A Review. Comprehensive Reviews in Food Science and Food Safety., 17(2), 1465-1483. https://doi.org/10.1111/1541-4337.12386
Wagstaff LR, Mitton MW, Arvik BM & Doraiswamy PM., (2003). Statin-associated memory loss: analysis of 60 case reports and review of the literature. Pharmacotherapy., 23(7), 871-880. doi: 10.1592/phco.2 3.7.871.32720.
Zhang MQ & Barrie Wilkinson, (2007) Drug discovery beyond the ‘rule-of-five’. Curr.Opin.Biotechnol., 18(6), 478-488. https://doi.org/10.1016/j.copbio.2007.10.005.
Bajwa AA, Zulfiqar U, Sadia S, Bhowmik P & Chauhan BS. (2019). A global perspective on the biology, impact and management of Chenopodium album and Chenopodium murale: two troublesome agricultural and environmental weeds. Environmental Science and Pollution Research, 26, 5357 – 5371 https://doi.org/10.1007/s11356-018-04104-y.
Cutillo F, DellaGreca M, Gionti M, Previtera L & Zarrelli A. (2006). Phenols and lignans from Chenopodium album. Phytochem Anal. 17(5), 344-349. doi:10.1002/pca.924.
Charles-Schoeman C, Fleischmann R, Davignon J, Schwartz H, Turner SM, Beysen C, Milad M, Hellerstein MK, Luo Z, Kaplan IV, Riese R, Zuckerman A & McInnes IB. (2015). Potential mechanisms leading to the abnormal lipid profile in patients with rheumatoid arthritis versus healthy volunteers and reversal by tofacitinib. Arthritis Rheumatol., 67(3), 616-625. doi: 10.1002/art.38974.
FilimonovD, PoroikovV & Borodina GloriozovaT. (1999). Chemical Similarity Assessment Through Multilevel Neighborhoods of Atoms: Definition and Comparison with the Other Descriptors. J. Chem. Inf. Comput. Sci. 39(8), 666-670.
GoharAA & Elmazar MMA (1997). Isolation of hypotensive flavonoids from Chenopodium species growing in Egypt. Phytother Res., 11, 564–567.
Guedes, I. A, Barret A. M. S, Marinho, Krempser E, Kuenemann MA, Sperandio O, Dardenne L E & Miteva M A. (2021). Machine Learning and Physics-Based Scoring Functions for Drug Discovery. Sci.Rep., 11 (1), 3198-3217. https://doi.org/10.1038/s41598-021-82410-1.
GarnatjeT, Peñuelas J & Vallès, (2017) Ethnobotany, phylogeny, and ‘omics’ for human health and food security. Trends Plant Sci., 22(3), 187–191. DOI: 10.1016/j.tplants.2017.01.001
Guarise M, Borgonovo G, Bassoli A & Ferrante A. (2019). Evaluation of two wild populations of Hedge Mustard (Sisymbrium officinale (L.) Scop.) as a potential leafy vegetable. Horticulturae., 5(1), 13-23, https://doi.org/10.3390/horticulturae5010013
Jamolowicz AI, Chen HY & Panegyres PK (2015). Statins and memory loss: An Australian experience. Australas Med J., 8(3), 73-79. doi: 10.4066/AMJ.2015.2014.
Khan T, Dixit S, Ahmad R, Raza S, Azad I, Joshi S & Khan AR. (2017). Molecular docking, PASS analysis, bioactivity score prediction, synthesis, characterization and biological activity evaluation of a functionalized 2-butanone thiosemicarbazone ligand and its complexes. J.Chem.Biol., 10(3), 91–104. https://doi.org/10.1007/s12154-017-0167-y.
Laghari AH, Memon S, Nelofar A, Khan KM & Yasmin A. (2011). Determination of free phenolic acids and antioxidant activity of methanolic extracts obtained from fruits and leaves of Chenopodiumalbum. Food Chem., 126(4), 1850-1855. doi: 10.1016/j.foodchem.2010.11.165.
Lipinski, Christopher. (2004). Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov. Today Technol., 1(4), 337-341. DOI:10.1016/j.ddtec.2004.11.007
Lee JC, Park BK, Choung S, Kim JM, Joung KH, Lee JH, Kim KS, Kim HJ, Jeong JW, Rhee SD & Ku BJ. (2014). Amelioration of Hypercholesterolemia by an EGFR Tyrosine Kinase Inhibitor in Mice with Liver-Specific Knockout of Mig-6. PLoS ONE 9(12): 1-13. https://doi.org/10.1371/journal.pone.0114782
Morand OH, Aebi JD, Dehmlow H, Ji YH, Gains N, Lengsfeld H & Himber J. (1997). Ro 48-8071, a new 2,3-oxidosqualene: lanosterol cyclase inhibitor lowering plasma cholesterol in hamsters, squirrel monkeys, and minipigs: comparison to simvastatin. Journals of Lipid Research., 38(3), 373-390.
Pala, N.A., Sarkar B.C., Shukla, G, Nakul C Shovik D., Jahangeer AB & Sumit C (2019). Floristic composition and utilization of ethnomedicinal plant species in home gardens of the Eastern Himalaya. J Ethnobiology Ethnomedicine., 15(14), 1-16. https://doi.org/10.1186/s13002-019-0293-4
Santos KB, Guedes IA, Karl ALM & Dardenne LE. (2020). Highly Flexible Ligand Docking: Benchmarking of the DockThor Program on the LEADS-PEP Protein–Peptide Data Set, J.Chem.Inf Model., 60 (2), 667-683. doi: 10.1021/acs.jcim. 9b00905.
Salmerón-ManzanoEsther, Garrido-Cardenas Jose A & Manzano-Agugliaro, Francisco (2020). Worldwide Research Trends on Medicinal Plants. Int. J. Environ. Res. Public Health 17(10) 3376-3396. https://doi.org/10.3390/ijerph17103376
Telford DE, Lipson SM, Barrett PH, Sutherland BG, Edwards JY, Aebi JD, Dehmlow H, Morand OH & Huff MW. (2005). A Novel Inhibitor of Oxidosqualene:Lanosterol Cyclase Inhibits Very Low–
Density Lipoprotein Apolipoprotein B100 (ApoB100) Production and Enhances Low-Density Lipoprotein ApoB100 Catabolism Through Marked Reduction in Hepatic Cholesterol Content. Arteriosclerosis, Thrombosis, and Vascular Biology., 25(12), 2608-
2614. https://doi.org/10.1161/01.ATV.0000189158.2845 5. 94
Thilakavathy Thangasamy, Sivanandane Sittadjody & Randy Burd (2009). Chapter 27 - Quercetin: A Potential Complementary and Alternative Cancer Therapy, Complementary and Alternative Therapies and the Aging Population, Academic Press., 563-584. https://doi.org/10.1016/B978-0-12-374228-5.00027-5.
Vanessa Sales de Oliveira, Fernanda Silva Ferreira, Maria Clara Ramos Cople, Tatiana da Silva Labre, Ivanilda Maria Augusta, Ormindo Domingues Gamallo &Tatiana Saldanha (2018), Use of Natural Antioxidants in the Inhibition of Cholesterol Oxidation: A Review. Comprehensive Reviews in Food Science and Food Safety., 17(2), 1465-1483. https://doi.org/10.1111/1541-4337.12386
Wagstaff LR, Mitton MW, Arvik BM & Doraiswamy PM., (2003). Statin-associated memory loss: analysis of 60 case reports and review of the literature. Pharmacotherapy., 23(7), 871-880. doi: 10.1592/phco.2 3.7.871.32720.
Zhang MQ & Barrie Wilkinson, (2007) Drug discovery beyond the ‘rule-of-five’. Curr.Opin.Biotechnol., 18(6), 478-488. https://doi.org/10.1016/j.copbio.2007.10.005.
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How to Cite
Molecular docking studies of Chenopodium album Linn with Lanosterol synthase enzyme. (2021). Journal of Applied and Natural Science, 13(2), 491-495. https://doi.org/10.31018/jans.v13i2.2618
