COMPUTATIONAL INTERACTION OF ENTOMOPATHOGENIC FUNGAL SECONDARY METABOLITES WITH PROTEINS INVOLVED IN HUMAN XENOBIOTIC DETOXIFICATION
Keywords:
Entomopathogenic fungi, Xenobiotic detoxification, In silico interaction, Serinocyclin-A, Glutathione S-transferase, Molegro virtual Docker, Helvolic acid, Cytochalasin B, Beauverolide HAbstract
Objective: Entomopathogenic fungi are rich source of secondary metabolites which posses both pharmacological and insecticidal activity. It is essential to assess metabolite toxicity of chemically diverse toxic metabolites of entomopathogenic fungus. Human acetylcholine esterase, cytochrome p450 and glutathione S-transferase are important enzymes involved in human xenobiotic detoxification.
Methods: In this study, in silico interaction of 13 selected secondary metabolites of entomopathogenic fungi with the target human proteins were carried out using Molegro Virtual Docker 4.0.2.
Results: This study reveals serinocyclin-A, have shown highest binding energy (176.07 KJ mol-1) with glutathione S-transferase followed by helvolic acid, cytochalasin B and beauverolide H have shown considerable inhibition among the metabolites tested.
Conclusion: The study concludes that serinocyclin-A, helvonic acid, cytochalasin B and beauverolide among 13 secondary metabolites tested were found to be more toxic and may inhibit the human metabolic pathways.
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Molnar I, Gibson DM, Krasnoff SB. Secondary metabolites from entomopathogenic Hypocrealean fungi. Nat Prod Rep 2010;27:1241-75.
Isaka M, Kittakoop P, Kirtikara K, Jones NLH, Thebtaranonth Y. Bioactive Substances from Insect Pathogenic Fungi. Acc Chem Res 2005;38:813-23.
Vey A, Hoagland R, Butt TM. Toxic metabolites of fungal biocontrol agents. In: Fungi as Biocontrol Agents. Progress, Problems & Potential. Butt TM, Jackson C. Magan N, Eds. CABI, Wallingford; 2001. p. 311-46.
Li Z. Recent progress in study of Cordyceps spp. and their application development for food and medicine materials. International Symposium on development on food and medicinal materials using agro-materials, Seoul, Korea; 2010.
Ravensberg WJ. A road map to the successful development and commercialization of microbial pest control products for control of Arthropods. Progress in Biological control. Dordrecht. The Netherland Springer 2011;10:1-5.
Ownley BH, Gwinn KD, Vega FE. Endophytic fungal entomopathogens with activity against plant pathogens: ecology and evolution. Bio Control 2010;55:113-28.
Faria MRD, Wraight SP. Mycoinsecticides and Mycoacaricides: A comprehensive list with worldwide coverage and international classification of formulation types. Bio Control 2007;43:237-56.
Laengle T, Strasser H. Developing a risk index to comparatively assess environmental risks posed by microbial and conventional pest control agents. Biocont Sci Technol 2010;20 (7):659-81.
Strasser H, Vey A, Butt TM. Are there any risks in using entomopathogenic fungi for pest control, with particular reference to the bioactive metabolites of Metarhizium, Tolypocladium and Beauveria species? Bio Sci Tech 2000;10:717–35.
Josephy PD. Genetic Variations in Human Glutathione Transferase Enzymes: Significance for Pharmacology and Toxicology. Hum Genomics Proteomics 2010;2010:1-14.
Wang YM, Lin W, Chai SC, Wu J, Ong SS, Schuetz EG, Chen T. Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1. Toxicol Appl Pharmacol 2013;272(1):96-107.
Pohanka M. Alpha7 Nicotinic Acetylcholine Receptor Is a Target in Pharmacology and Toxicology. Int J Mol Sci 2012;13:2219-38.
Favilla M, Macchia L, Gallo A, Altomare C. Toxicity assessment of metabolites of fungal biocontrol agents using two different (Artemia salina and Daphnia magna) invertebrate bioassays. Food Chem Toxicol 2006;44:1923-31.
Sharma AK, Gaur K, Tiwari Rk, Gaur MS. Computational interaction analysis of organophosphorus pesticides with different metabolic proteins in humans. J Biomed Res 2011;25(5):335-47.
Fan J, Xie Y, Xue J, Liu R. The effect of Beauveria brongniartii and its secondary metabolites on the detoxification enzymes of Pine cater pillar, Dendrolimus tabulaeformis. J Insect Sci 2013;13:44.
Krasnoff SB, Keresztes I, Gillilan RE, Szebenyi DME, Donzelli BGG, Churchill ACL, Gibson DM. Serinocyclins A and B, cyclic heptapeptides from Metarhizium anisopliae. J Nat Prod 2007;70:1919–24.
Thomas MB, Read AF. Can fungal biopesticides control malaria? Nat Rev Microbiol 2007;5:377–83.
Moon YS, Donzelli BGG, Krasnoff S, McLane H, Griggs MH, Cooke P, Vandenberg JD, et al. Agrobacterium-mediated disruption of a non ribosomal peptide synthetase gene in the fungal invertebrate pathogen Metarhizium anisopliae reveals a peptide spore factor. Appl Environ Microbiol 2008;74:4366–80.
Donzelli BGG, Krasnoff SB, Churchill ACL, Vandenberg JD, Gibson DM. Identification of a hybrid PKS–NRPS required for the biosynthesis of NG-391 in Metarhizium robertsii. Curr Genet 2010;56:151–62.
Ratnaweera PB, Williams DE, Silva ED, Wijesundera RLC, Dalisay, Andersen RJ. Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp of orchid Anoectochilus setaceus endemic to Sri Lanka. Mycology 2014;5(1):23-8.
Haidle AM, Myers AG. An enantioselective modular and general route to the cytochalasin: synthesis of L-696 474 and cytochalasin B. Proceedings of the National Academy of Sci 2004;101(33):12048-53.
Azumi M, Ishidoh K, Kinoshita H, Nihira T, Ihara F, Fujita T. Aurovertins F-H from the Entomopathogenic Fungus Metarhizium anisopliae. J Nat Prod 2008;71:278-80.
Huang TC, Chang HY, Hsu CH, Kuo WH, Chang KJ, Juan HF. Targeting therapy for breast carcinoma by ATP synthase inhibitor aurovertin B. J Proteome Res 2008;7:1433-44.
Claydon N, Grove JF. Insecticidal secondary metabolic products from the entomogenous fungus Verticillium lecanii. J Invertebr Pathol 1982;40:413–8.
Edwards TG, Helmus MJ, Koeller K, Bashkin JK, Fisher C. Human papilloma virus episome stability is reduced by Aphidicolin and controlled by DNA damage response pathways. J Virol 2013;87(7):3979-89.
Xu Y, Orozco R, Wijeratne EMK, Artiles PE, Gunatilaka AAL, Stock SP, et al. Biosynthesis of the cyclooligomer depsipeptide bassianolide, an insecticidal virulence factor of Beauveria bassiana. Fungal Genet Biol 2009;46:353–64.
Suzuki A, Kanaoka M, Isogai A, Murakoshi S, Ichinoe M, Tamura S. Bassianolide, a new insecticidal cyclodepsipeptide from Beauveria bassiana and Verticillium lecanii. Tetrahedron Lett 1977;25:2167-70.
Hamill RL, Higgens GE, Boaz HE, Gorman M. The structure of beauvericin, a new desipeptide antibiotic toxic to Artemia salina. Tetrahedron Lett 1969;49:4255-58.
Wang Q, Xu L. Beauvericin, a Bioactive Compound Produced by Fungi. Molecules 2012;17:2367-77.
Namatame I, Tomoda H, Tabata N, Si S, Omura S. Structure Elucidatation of Fungal Beauveriolide III, a Novel Inhibitor of Lipid Droplet Formation in Mouse Macrophages. The Journal of Antibiotics 1999;52:7-12.
Namatame I, Tomoda H, Ishibashi S, Omura S. Antiatherogenic activity of Fungal Beauverioloides, Inhibitors of Lipid Droplet Accumulation in Macrophages. Proc Natl Acad Sci U S A 2004;101:737-42.
Vilcinskas A, Matha V, Gotz P. Effects of the entomopathogenic fungus Metarhizium anisopliae and its secondary metabolites on morphology and cytoskeleton of plasmatocytes isolated from the greater wax moth, Galleria mellonella. Jou Ins Phy 1997;43(12): 1149-59.
Scheumann J, Hertweck C. Molecular basis of cytochalasin biosynthesis in fungi: gene cluster analysis and evidence for the involvement of a PKS-NRPS hybrid synthase by RNA silencing. J Am Chem Soc 2007;129:9564–65.
Pedras MSC, Irina Zaharia L, Ward DE. The destruxins: Synthesis, biosynthesis, biotransformation, and biological activity. Phytochemistry 2002;59:579–96.
Kershaw MJ, Moorhouse ER, Bateman R, Reynolds SE, Charnley AK. The role of destruxins in the pathogenicity of Metarhizium anisopliae for three species of Insect. J Invertebr Pathol. 1999;74:213–23.
Claydon N, Grove JF. Insecticidal secondary metabolic products from the entomopathogenous fungus Verticillium lecanii. J. Invertebr. Pathol. 1982;40:413-18.
Soman AG, Gloer JB, Angawi RF, Wicklow DT, Dowd PF. Vertilecanins:new phenopicolinic acid analogues from Verticillium lecanii. J. Nat. Prod. 2001;64:189-92.
Lee S, Kinoshita H, Ihara F, Igarashi Y, Nihira T. Identification of novel derivative of helvolic acid from Metarhizium anisopliae grown in medium with insect component. J Biosci Bioeng 2008;105:476–80.
Seger C, Erlebach D, Stuppner H, Griesser UJ, Strasser H. Physico-chemical characterization of oosporein, a major metabolite of the entomopathogenic fungus Beauveria brongniartii. Helv Chim Acta 2005;88:802–10.
Terry BJ, Liu WC, Cianci CW, Proszynski E, Fernandes P, Meyers E. Inhibition of Herpes Simplex virus type I DNA polymerase by the natural product oosporein. The Journal of Antibiotics 1992;2:286-88.
Li Z, Huang Y, Dong F, Li W, Ding L, Yu G, et al. Swainsonine promotes apoptosis in human oesophageal squamous cell carcinoma cells in vitro and in vivo through activation of mitochondrial pathway. J Biosci 2012;37:1005–16.
Sun JY, Yang H, Miao S, Li JP, Wang SW, Zhu MZ, et al. Suppressive effects of swainsonine on C6 glioma cell in vitro and in vivo. Phytomedicine 2009;16:1070–74.
You N, Liu W, Wang T, Ji R, Wang X, Gong Z, Dou K, et al. Swainsonine inhibits growth and potentiates the cytotoxic effect of paclitaxel in hepatocellular carcinoma in vitro and in vivo. Oncol Rep 2012;28:2091-2100.
Wat CK, McInnes AG, Smith DG. The yellow pigments of Beauveria species. Structures of tenellin and bassianin. Can. J. Chem 1977;55:4090-98.
Jeffs LB, Khachatourians GG. Toxic properties of Beauveria pigments on erythrocyte membranes. Toxicon 1997;35(8): 1351-56.