ACL-4, an Endophytic Fungus Isolated from Ageratum conyzoides Leaves Possesses the Unique Potential of Generating Low Molecular Weight Bioactive Lead Compounds . http://www.doi.org/10.26538/tjnpr/v6i12.24
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Abstract
Over the years, endophytic fungi have generated novel bioactive lead molecules for drug development. A detailed chemical investigation of ACL-4, an endophytic fungus previously isolated from Ageratum conyzoides, led to the isolation of eight low molecular weight bioactive secondary metabolites. The metabolites generated by the axenic fungus, when grown on rice medium using solid fermentation, were extracted using ethyl acetate. Further chromatographic separation of the crude extract led to the isolation of compounds 1-8. The chemical structures of these compounds were determined using a combination of HPLC-DAD, and NMR analyses. The fractions from which the compounds were isolated were also subjected to antimicrobial screening using Agar well dilution techniques. The chemical structures of the compounds were elucidated as 2-hydroxy-6- (1'-hydroxyethyl) benzoic acid (1), 2-(4'-hydroxyphenyl) ethanol (2), 4-hydroxybenzoic acid (3), 2-(4'-methylphenyl) ethanol (4), 3-methoxy-4-hydroxybenzoic acid (5), epiguaymasol (6), 2- {4'- (4''hydroxyphenyl) methylphenyl) ethanol (7), and protocatechuic acid (8). The tested fractions displayed varying degrees of antimicrobial activity, with MICs ranging from 0.125 – 0.5 mg/mL. The antimicrobial activities shown by the fungal extract and fractions may be as a result of the presence of some of these compounds, which have been previously reported as antimicrobial agents.
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Amaechi AA, Oli AN, Okezie UM, Adejumo SA, Abba CC, Okeke IJ, Okoye FBC. Secondary Metabolites of Endophytic Fungi from Newbouldia laevis and Cassia tora Leaves: Prospecting for New Antimicrobial Agents. Recent Advances in Anti-Infect Drug Dis (Formerly Recent Pat on Anti-Infect Drug
Dis) 2021; 16(1):50-62.
Fasinu PS, Okoye FBC, Abiodun OO, Kamdem RST and Ogbole OO. Editorial: Fungal Bioactive Metabolites of Pharmacological Relevance. Front. Pharmacol. 2022; 13:912068.
Okezie UM, Eze PM, Okoye FBC, Esimone CO. Orthosporin, a major component of the fermentation product of Lasiodiplodia theobromae – an endophytic fungus of Musa paradisiaca as a potential antimicrobial agent. Notulae Scientia Biologicae 2022; 14 (2): 11084.
Nwobodo DC, Eze PM, Okezie UM, Okoye FBC, Esimone CO. Bioactive Compounds Characterization and Antimicrobial Potentials of Crude Extract of Curvularia lunata, a Fungal Endophyte from Elaeis guineensis. Trop J Nat Prod Res. 2022; 6(3):395–402.
Ujam NT, Ajaghaku DL, Okoye FBC, Esimone CO. Antioxidant and immunosuppressive activities of extracts of endophytic fungi isolated from Psidium guajava and Newbouldia laevis. Phytomedicine Plus. 2021; 1(2):100028.
Chigozie VU, Okezie MU, Ajaegbu EE, Okoye FBC, Esimone CO. Bioactivities and HPLC analysis of secondary metabolites of a morphologically identified endophytic Aspergillus fungus isolated from Mangifera indica, Nat Prod Res, 2021; 1-5.
Uzor PF, Ebrahim W, Osadebe PO, Nwodo JN, Okoye FBC, Müller W, Lin W, Liu Z, Proksch P. Metabolites from Combretum dolichopetalum and its associated endophytic fungus Nigrospora oryzae – Evidence for a metabolic partnership. Fitoter. 2015; 105:147-150.
Ebada SS, Eze P, Okoye FBC, Esimone CO, Proksch P. The Fungal Endophyte Nigrospora oryzae Produces Quercetin Monoglycosides Previously Known Only from Plants. Chem Sel. 2016; 1(11):2767-2771.
Alvin A, Miller KI, Neilan BA. Exploring the potential of endophytes from medicinal plants as sources of antimycobacterial compounds. Microbiol Res. 2014; 169:483– 495.
Stierle A, Strobel G, Stierle D. Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew. Sci. 1993; 260(5105):214–216.
Li JY, Sidhu RS, Bollon A, Strobel GA. Stimulation of taxol production in liquid cultures of Pestalotiopsis microspore. Mycol Res. 1998; 102:461–464.
Puri SC, Verma V, Amna T, Qazi GN, Spiteller M. An endophytic fungus from Nothapodytes foetida that produces camptothecin. J Nat Prod. 2005; 68:1717–1719.
Puri SC, Nazir A, Chawla R, Arora R, Riyaz-Ul-Hasan S, Amna T, Ahmed B, Verma V, Singh S, Sagar R, Sharma A, Kumar R, Sharma RK, Qazi GN. The endophytic fungus Trametes hirsuta as a novel alternative source of podophyllotoxin and related aryl tetralin lignans. J Biotech. 2006; 122(4):494–510.
Guo B, Li H, Zhang L. Isolation of a fungus producing vinblastine, J. Yunnan Univ. 1998; 20:214–215.
Yang X, Zhang L, Guo B, Guo S. Preliminary study of a vincristine-producing endophytic fungus isolated from leaves of Catharanthus roseus, Zhong Cao Yao (Chin Tradit. Herb. Drugs). 2004; 35:79–81.
Ujam NT, Eze PM, Chukwunwejim CR, Okoye FBC, Esimone CO. Antimicrobial and immunomodulatory activities of secondary metabolites of an endophytic fungus isolated from Ageratum conyzoides. Curr Life Sci. 2019; 5(1):19-27.
Trischman JA, Jensen PR, Fenical W. Guaymasol and Epiguaymasol: Aromatic Triols from a DeepSea Bacillus Isolate. Nat Prod Lett. 1998; 11(4):279-284.
Guimarães DO, Borges KB, Bonato PS, Pupo MT. Simple method for the quantitative analysis of tyrosol by HPLC in liquid Czapek Cultures from endophytic fungi. J Braz Chem Soc. 2009; 20(1):188-194.
Abba CC, Eze PM, Abonyi DO, Nwachukwu CU, Proksch P, Okoye FBC, Eboka CJ. Phenolic Compounds from Endophytic Pseudofusicoccum sp. Isolated from Annona muricata. Trop J Nat Prod Res. 2018; 2(7):332-337.
Giovannini C, Straface E, Modesti D, Coni E, Cantafora A, De Vincenzi M, Malorni W, Masella R. Tyrosol, the major olive oil biophenol, protects against oxidized-LDL induced injury in Caco-2 cells. J Nutr. 1999; 129:1269–1277.
EU Commission Implementing Regulation. No 872/2012. Off J Eur Union. 2012; Document 32012R0872 http://data.europa.eu/eli/reg_impl/2012/872/oj.
Cho JY, Moon JH, Seong KY, Park KH. Antimicrobial activityof 4-hydroxybenzoic acid and trans 4-hydroxycinnamic acid isolated and identified from rice hull. Biosci Biotechnol Biochem. 1998; 62(11):2273-2276.
Farhoosh R, Johnny S, Asnaashari M, Molaahmadibahraseman N, Sharif A. Structure-antioxidant activity relationships of ohydroxyl, o-methoxy, and alkyl ester derivatives of phydroxybenzoic acid. Food Chem. 2016; 194:128-134.
Lewis RJ, Sr (Ed.). Hawley's Condensed Chemical Dictionary. 3th ed. New York: John Wiley & Sons, Inc.; 1997; 595p.
O'Neil MJ. (Ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc.; 2001; 862p.
Verschueren K. Handbook of Environmental Data on Organic Chemicals. 4th ed. New York: John Wiley & Sons; 1997; 1296p.
Ullmann's Encyclopedia of Industrial Chemistry. Federal Republic of Germany: 6th ed. Vol 1: Wiley-VCH Verlag GmbH & Co. 2003 to Present, 2003; 17:330p.
Kakkar S and Bais S. A Review on Protocatechuic Acid and Its Pharmacological Potential. ISRN Pharmacol. 2014; Article ID 952943:1-9.
Abonyi DO, Eze PM, Abba CC, Ujam NT, Proksch P, Okoye FBC, Esimone CO. Biologically active phenolic acids produced by Aspergillus sp., an endophyte of Moringa oleifera. Eur J Biol Res. 2018; 8(3):158-168.