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Repositioning the Bioactive Compounds Isolated from Bauhinia

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Repositioning the Bioactive Compounds Isolated from Bauhinia Communication in Physical Sciences 2020, 6(1); 627-634 Repositioning the Bioactive Compounds Isolated from Bauhinia Galpinii Leaves as Potential Inhibitors Against Human Immunodeficiency Virus (HIV) II Protease Through Application of In Silico Studies Victor Okezie Ikpeazu, Amaku James Friday, Kalu K. Igwe and Ifeanyi E. Otuokere, Received 30 June 2020/Accepted 29 August 2020/Published online: 01 September 2020 Abstract The global health implication of human Email: [email protected] immunodeficiency virus (HIV) II protease has Orcid id: 0000-0002-8118-5689 posed an unmatched health challenge provoking Ifeanyi E. Otuokere increasing interest in search, design and Department of Chemistry, Michael Okpara development of new. Therapeutic agents with the University of Agriculture, capacity to curb the spread of the disease. The Umudike, Abia State Nigeria bioactive compound in the leaf extract of Bauhinia Email: [email protected] galpiniiand were investigated for inhibitory Orcid id: 0000-0002-7921-8250 activity against human immunodeficiency virus (HIV) II protease using molecular docking 1.0 Introduction technique. Result obtained from the docking Bauhinia galpinii (Fabaceae), commonly known analysis revealed that 24-isopropylcholest-5-en- as “Pride of De Kaap” or Pride of the Cape due to 3, 8-diol-1hsh interacted with binding energies of its attractive nature. It is commonly found in -5.6 Kcal/mol and was selected as the lead some parts of Eastern and Southern Africa. molecule. This molecule was observed to interact However, the plant originated from South Africa with PRO81, ILE84, ALA28, ASP29, ASP30, (Aderogba et al., 2007; Erhabor et al., 2020). ILE32, MET76, VAL47, GLY48, GLY49 and Bauhinia galpinii is a shrub (creeper) and belongs ILE50 within the active site of the 1hsh. ADME to the Fabaceae family. Besides its usage as a prediction revealed that the lead molecule obeys garden plant, different part of Bauhinia galpinii the Lipinski rule without any violation and had a are extensively used in folk medicine to treat a 0.55 bioavailability score. The blood-brain variety of ailments. Available literature reveals barrier (BBB) permeant and gastrointestinal that the leaf of the plant is often used by absorption (GI) were hindered and low, alternative medical practitioner to manage respectively. The study concluded that 24- epilepsy and convulsions (Risa et al., 2004), isopropylcholest-5-en-3, 8-diol is a promising diarrhoea and infertility are commonly treated candidate for the development of HIV drug. using the bark and leaves of Bauhinia galpinii. Key Words: Morus alba, molecular docking, The seeds are also used to treat amenorrhoea (Van ADMET, bioactive compound Wyk & Gericke, 2000) while the root are useful Victor O. Ikpeazu for the treatment of stomach spasms and infertility Department of Biochemistry, Abia State challenge (Arnold & Gulumian, 1984). The tuber University, Abia State is used to treat pneumonia, venereal disease and Email: [email protected] diarrhoea (Van Wyk & Gericke, 2000). The Amaku James Friday treatment of diabetes, inflammation, Department of Chemistry, Michael Okpara gastrointestinal tract (GIT) disorders and University of Agriculture, infectious diseases are commonly achieved using Umudike, Abia State Nigeria Bauhinia species (Ahmed et al., 2012; Filho, Email: [email protected] 2009) (Ahmed et al., 2012; Filho, 2009). In a bid Orcid id: 0000-0003-4894-0512 to define the pharmacological characteristics of Bauhinia galpinii, by several researchers, findings Kalu . K. Igwe indicate that its leaves contain antiepileptic, Departmemt of Veterinary Physiology, antimutagenicity antioxidant, antimicrobial, and Pharmacology and Biochemistry, cytotoxicity properties (Aderogba et al., 2007; Michael Okpara University of Agriculture, Reid et al., 2006; Risa et al., 2004). Umudike, Abia Satate, Nigeria Communication in Physical Sciences 2020, 5(4): 627-634 Available at https://journalcps.com/index.php/volumes Communication in Physical Sciences 2020, 6(1); 627-634 628 In 1981 acquired immunodeficiency syndrome 2.0 Receptor and ligand preparation (AIDS) was recognized and was reported to be The chemical structure of the bioactive compounds caused by human immunodeficiency virus (HIV- was built using ACD/ChemSketch 2018.2.5 1). The high degree of human immunodeficiency Freeware version. The 2D conformation of the virus replication results in high viral load and bioactive compounds was converted into their 3D immune-mediated destruction of the key immune forms. Thereafter, the molecules were optimized effector cell (CD4 lymphocyte). Different strain using the MMF94 force field on Avogadro of HIV tend to vary and dominate with interface (Hanwell et al., 2012). The dock-prep geographical location. Consequently, subtype B tools on the UCSF Chimera interface were used to is most prevalent in the Americas and Europe, prepare the optimized chemical structures before subtype C accounts for half of all strains identified the molecular docking step. The crystallized globally. However, the exact mechanism structure of human immunodeficiency virus underlying the CD4 decline in HIV patient is not (HIV) II protease complexing with a L-735,524, fully understood (Lewthwaite & Wilkins, 2009). an orally bioavailable inhibitor (ID: 1hsh) with Owing to its global spread and health implication, 1.9 Å resolution was retrieved from the Protein HIV/AIDS was declared a pandemic on the 5th of Data Bank (https://www.rcsb.org). The structure June 1981. Currently, researches on discovery of of the human immunodeficiency virus (HIV) II new active antiretroviral therapy (HAART) with protease consist of four distinct chains bounded better activity and possibility of complete cure is to small chemical residues (MK1). The ongoing and is receiving global research attention. preparation of the biological target (1hsh) was Record from WHO (2007) reveals that globally, performed on the UCSF Chimera interface 33.2 million people are living with HIV/AIDS (Pettersen et al., 2004). while 2.5 million new cases and 2.1 million deaths 2.2 Molecular docking have also been estimated. Generally, the major Molecular docking simulation was performed routes of transmission of this virus are through using AutoDockVina software (Morris et al., sexual (heterosexual) intercourse, parenterally 1998). Specific docking of the ligands to the (from mother to child), blood or blood product active site of the human immunodeficiency virus recipients, illicit drug-use and occupational (HIV) II protease (ID: 1hsh) was achieved by injury. According to Lewthwaite & Wilkins generating grid box coordinate of the ligand to be (2009), there is currently no vaccine/drug has substituted on the receptor. The grid box that been reported to have the capacity to truncate the defines the pocket of 1hsh receptor was designed viral replication of this virus (Lewthwaite & by making use of AutoDock Vina functionality on Wilkins, 2009) indicating that there is still a UCSF Chimera interface (Pettersen et al., 2004). research vacuum on the discovery and trial of new The grid box size and centre coordinates for the drugs with the hope of finding better options. 1hsh were x(11.1811, 14.871)Å, y (0.52812, Therefore, the aim of this study is to repurpose the 12.0096)Å and z (9.07564, 16.4572)Å bioactive compounds in Bauhinia galpinii leaves respectively. The bioactive compound with the as potential inhibitors against human highest binding affinity for the human immunodeficiency virus (HIV) II protease using immunodeficiency virus (HIV) II protease (ID: the molecular docking technique. 1hsh) was selected for further in silico ADME 2.0 Materials and Methods analysis. Fig 1: The crystalized structure of human immunodeficiency virus (HIV) II protease (ID:1hsh). Communication in Physical Sciences 2020, 6(1); 627-634 629 2.3 Validation and ADME analysis of lead et al., 2014; Keiser et al., 2007). The online web molecule server, SWISS-ADME (Adsorption, distribution, It is imperative to evaluate phenotypical side metabolism and excretion) was used to predict the effects or potential cross-reactivity caused by the drug-likeness, solubility uniqueness and action of small biomolecules in molecular pharmacokinetics characteristics of the lead simulation of ligand-receptor interaction (Gfeller molecule (https://www.swissadme.ch). 3.0 Results and Discussion 3.1 Docking scores Chemical identity (structure and IUPAC name) as compounds are presented in Table 1. well as docking score obtained for the isolated Table 1: 2D chemical structure of bioactive compound isolated from the leaf extract of Bauhinia galpiniiand their corresponding Glide score (G-Score) value calculated for the related query Score Code Names *G Stucture (Kcal/mol) H3C H3C CH3 CH3 24-Isopropylcholest-5-en-3, 8- CH3 CPD1 -7.3 CH3 diol H3C HO HO OH OH HO O OH Myricetin-3-O-beta CPD2 -7.2 O galactopyranose H OH O O H OH HO H H H OH OH OH HO O OH Quercetin-3-O-beta O CPD3 -6.9 H galactopyranose OH O O H OH HO H H H OH OH CH3 O OH 5, 7, 4', 5' tetrahydroxy-2- HO O CPD4 methoxyflavone -6.9 OH (Isoetin 2'-methyl ether) OH O OH OH 3, 5, 7, 3' 4', 5' HO O CPD5 Hexahydroxyflavone -6.8 OH (Myricetin) OH OH O In this study, six compounds reported to have been potential against human immunodeficiency virus isolated from the leaf extract of Bauhinia (HIV) II protease. The docking study revealed galpiniiand were studied to evaluate their binding that CPD1 (24-Isopropylcholest-5-en-3, 8-diol), Communication in Physical Sciences 2020, 6(1); 627-634 630 CPD2 (Myricetin-3-O-beta galactopyranose), was observed for ASP 30 and THR80 residues CPD3 (Quercetin-3-O-beta galactopyranose), (see Fig 3). Quercetin-3-O-beta galactopyranose CPD4 (5, 7, 4', 5' tetrahydroxy-2- was also observed to interact with ASP30, ILE32, methoxyflavone), CPD5 (3, 5, 7, 3' 4', 5' ASP25, VAL47, PRO81, ILE84, ILE82, GLY27, Hexahydroxyflavone) and CPD6 (3, 5, 7, 3' 4' ALA28, ASP29, GLY48, GLY49, ILE54 and Pentahydroxyflavone) had a favourable predicted THR80 residues which led to the formation of docking score of -7.3 kcal/mol, -7.2 kcal/mol, -6.9 hydrogen bonds with ASP30 and ASP25 (Fig 4).
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