In vitro Antifungal and In silico Antibacterial Evaluations of Anacardic Acid and its Complexes from Cashew Nut Shell Oil
doi.org/10.26538/tjnpr/v6i8.22
Keywords:
Anacardic acid,, Antibacterial,, Antifungal,, Anacardic acid complexes.Abstract
Anacardic Acids (AcA) have been documented to have particularly important pathogenic properties. AcA and its complexes are being investigated in this article for their antimicrobial activities through in vitro and in silico assay methods. AcA from the cashew nut shell oil (CNSO) was isolated and Fourier-transform infrared spectroscopy (FTIR) and Proton nuclear magnetic resonance (1HNMR) were used to characterise the compound. AcA complexes were synthesised with hydrated metal (II) ions of Cobalt and Copper in a ratio of 1:1 using a modified method by Mendes et al. The antifungal activities of these AcA metal complexes were tested against five fungi. While AcA showed no antifungal activity, its complexes showed interesting results. Anacardic acid complex of cobalt (AcA-Co) showed activities against three of the five fungi; the best activity was against Penicillium citrinum (30±7.07 mm); a better result than clotrimazole (12.5±0.71 mm) which was the reference standard drug used. Anacardic acid complex of copper (AcA-Cu) also showed activities against all fungi tested against except Aspergillus flavus with the best activity also against Penicillium citrinum (15±2.83 mm). Standard precision (SP) and extra precision (XP) docking of AcA with 1Y54 revealed that it inhibits Enterococcus spp. better than standard drugs (Streptomycin and Tetracycline) as shown by docking scores and degree of binding affinities. These results of AcA and its complexes suggest additional studies which could lead to the development of new antifungal and antibacterial agents.
References
Saedtler M, Förtig N, Ohlsen K, Faber F, Masota N, Kowalick K, Meinel L. Anti-bacterial anacardic acid derivatives. ACS Infect Dis. 2020; 6(7):1674-1685.
Lima RA, de Souza SLX, Lima LA, Batista ALX, de Araújo JTC, Sousa FFO, Rolim JPML, Bandeira TJPG. Antimicrobial effect of anacardic acid-loaded zein nanoparticles loaded on Streptococcus mutans biofilms. Braz J Microbiol. 2020; 51(4):1623-1630.
Paramashivappa R, Kumar PP, Vithayathil PJ, Rao AS. Novel method for isolation of major phenolic constituents from cashew (Anacardium occidentale L.) nut shell liquid. J Agric Food Chem. 2001; 49(5):2548–2551.
Anon. Revised Test Plan for CNSO: Report submitted to The US-EPA by Cardolite Cooperation Inc., 2006; Cas No. 8007- 24-7www.cardolite.
Dos Santos ML, de Magalhães GC. Utilisation of cashew nut shell liquid from Anacardium occidentale as starting material for organic synthesis: A novel route to lasiodiplodin from cardols. J Braz Chem Soc. 1999; 10(1):13-20.
Ikeda R, Tanaka H, Uyama H, Kobayashi S. Synthesis and curing behaviors of a crosslinkable polymer from cashew nut shell liquid. Polymer. 2002; 43(12):3475-3481.
Kumar PP, Paramashivappa PJ, Vithayathil PJ, Subra Rao PV, Srinivasa Rao A. Process for isolation of cardanol from technical cashew (Anacardium occidentale) nut shell liquid. J Agric Food Chem. 2002; 50(16):4705-4708.
Ayyanar M and Ignacimuthu S. Herbal medicines for wound healing among tribal people in southern India: ethnobotanical and scientific evidences. Int J Appl Res Nat Prod. 2009; 3(3):29-42.
da Silva DPB, Florentino IF, da Silva Moreira LK, Brito AF, Carvalho VV, Vasconcelos GA, Rodriguesb MF, Vasconcelosb GA, Vazb BG, Pereira-Juniorc MA, Fernandesc KF, Costaa EA. Chemical characterization and pharmacological assessment of polysaccharide free, standardized cashew gum extract (Anacardium occidentale L.). J Ethnopharmacol. 2018; 213(1):395–402.
Kudi AC, Umoh JU, Eduvie LO, Gefu J. Screening of some Nigerian medicinal plants for antibacterial activity. J Ethnopharmacol.1999; 67(2):225–228.
Gomes Júnior AL, Islam MT, Nicolau LAD, de Souza LKM, Araújo TSL, Lopes de Oliveira GA, de Melo Nogueira K, da Silva Lopes L, Medeiros JR, Mubarak MS, Melo-Cavalcante AAC. Anti-Inflammatory, Antinociceptive, and Antioxidant Properties of Anacardic Acid in Experimental Models. ACS Omega. 2020; 31(5):19506-19515.
Marinho MM, dos Santos RP, Bezerra EM, Costa RF, Figueira CS, Martins AMC, Neto PL, Marinho ES, Nogueira VA, Albuquerque EL. Molecular fractionation with conjugate caps study of the interaction of the anacardic acid with the active site of trypanosoma cruzi gapdh enzyme: a quantum investigation. Asian J Pharm Clin Res. 2019; 12(12):183–189.
Park M, Upton D, Blackmon M, Dixon V, Craver S, Neal D, Perkins D. Anacardic acid inhibits pancreatic cancer cell growth, and potentiates chemotherapeutic effect by Chmp1A - ATM - p53 signaling pathway. BMC Compl Altern Med. 2018; 18(1):71-81.
da Silva W, Pinheiro SO, Alves DR, de Menezes J, Magalhães F, Silva F, Marinho MM, Marinho ES, de Morais SM. Anacardic Acid Complexes as Possible Agents Against Alzheimer's Disease Through Their Antioxidant, In vitro, and In silico Anticholinesterase and Ansiolic Actions. Neurotoxic Res. 2021; 39(2):467-476.
Schultz DJ, Krishna A, Vittitow SL, Alizadeh-Rad N, Muluhngwi P, Rouchka EC, Klinge CM. Transcriptomic response of breast cancer cells to anacardic acid. Sci Rep. 2018; 8:8063.
USP Global Public Policy Position: Addressing Antimicrobial Resistance. [Online]. 2020 [cited 2022 April 18]. Available from: https://www.usp.org/our-impact/antimicrobial-resistance.
Scorzoni L, de Paula e Silva ACA, Marcos CM, Assato PA, de Melo WCMA, de Oliveira HC, Costa-Orlandi CB, Mendes- Giannini MJS, Fusco-Almeida AM. Antifungal Therapy: New Advances in the Understanding and Treatment of Mycosis. Front Microbiol. 2017; 8(36):1-23.
Fisher JF and Mobashery S. Endless resistance. Endless antibiotics? Med Chem Comm. 2016; 7(1):37-49.
World Health Organization (WHO). The world is running out of antibiotics, WHO report confirms. [Online]. 2017 c https://www.who.int/news/item/20-09-2017-the-world-is- running-out-of-antibiotics-who-report-confirms.
Newman DJ and Cragg GM. Natural products as sources of new drugs from 1981 to 2014. J Nat Prod. 2016; 79(3):629-661.
Current Antibacterial Drug Development. [Online]. 2022 [cited 2022 July 15]. Available from: https://www.quinta.cz/news/current-antibacterial-drug- development.
Ruetschi P and Amlie RF. Solubility of hydrogen in potassium hydroxide and sulfuric acid. Salting-out and hydration. J Chem Phys. 1966; 70(3):718-723.
Mendes MN, de Oliveira AB, Guimarães JE, Pereira JP, Katz N. Molluscicidal activity of the mixture of 6-n-alkyl salicylic acids (anacardic acid) and its complexes with copper (II) and lead (II). Rev Soc Bras Med Trop. 1990; 23:217-224.
Oke DG and Oluranti OO. Antifungal, Antibacterial and Phytochemical Properties of Petiveria Alliacea Plant from Iwo Nigeria. Chem Res J. 2019; 4(1):12-18.
Protein Data Bank. [Online] 2022. [cited 2022 April 18]. Available from: https://rcsb.org.
Sastry GM, Adzhigirey M, Day T, Annabhimoju R, Sherman W. Protein, and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comp Aided Mol Des. 2013; 27(3):221-234.
Jacobson MP, Pincus DL, Rapp CS, Day TJF, Honig B, Shaw DE, Friesner RA. A hierarchical approach to all-atom protein loop prediction. Prot Struct Funct Bioinform. 2004; 55(2):351- 367.
Lig. Prep., Schrödinger. Schrödinger Release 2021-3: LLC, New York: NY; 2021.
Halgren T. Identifying and characterizing binding sites and assessing drug ability. J Chem Inf Model. 2009; 49(2):377-389.
Friesner RA, Murphy RB, Repasky MP, Frye LL, Greenwood JR, Halgren TA, Sanschagrin PC, Mainz DT. Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J Med Chem. 2006; 49(21):6177-6196.
Olanrewaju AA and Osowole AA. Synthesis, Spectroscopic Characterization and Antioxidant properties of some metal (ii) complexes of mixed drugs vitamin Bx and Paracetamol. F. J. Res Sci. 2017; 13(2):190-198.
Awad SH. Synthesis and characterization of some mixed –ligand complexes containing salicylic acid and pyridine with some metal ions. J Al-Nahrain Univ. 2012; 15(3):23-29.
Morais SM, Silva KA, Araujo H, Vieira IG, Alves DR, Fontenelle RO, Silva AM. Anacardic Acid Constituents from Cashew Nut Shell Liquid: NMR Characterization and the Effect of Unsaturation on Its Biological Activities. Pharm (Basel). 2017; 10(1):31-41.
Prithiviraj B, Singh UP, Manickam M, Ray AB. Antifungal activity of anacardic acid, a naturally occurring derivative of salicylic acid. Can J Bot. 1997; 75(1):207–211.
Published
How to Cite
Issue
Section
License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
