Antimicrobial, Cytotoxic, Antiviral Effects, and Spectroscopic Characterization of Metabolites Produced by Fusarium oxysporum YP9B

Abstract

The goal of the work is to determine the bioactive pharmaceutical metabolites produced by the Fusarium oxysporum YP9B isolate. Ten new natural compounds were isolated from the ethyl acetate extract of the F. oxysporum YP9B strain. Their structures were elucidated by spectroscopic methods using 1D and 2D NMR, UV, FT-IR, and mass spectra (LC-QTOF MS and GC-FID/MS). Identified compounds were named as; (1-benzyl-2-methoxy-2-oxoethyl)-2-hydroxy-3-methylbutanoate (1), 2-oxo-8-azatricyclo[9.3.1.13,7]-hexadeca-1(15),3(16),4,6,11,13-hexaen-10-one (2), 2,3-dihydroxypropanoic, hexadecanoic anhydride (3a), 2,3-dihydroxypropanoic (9Z)-octadecenoic anhydride (3b), 2,3-dihydroxy-propanoic (9Z,12Z)-octadecadienoic anhydride (3c), 2,3-dihydroxypropanoic (11Z)-octadecenoic anhydride (4a), 2,3-dihydroxypropanoic, (9E,12E)-octadecadienoic anhydride (4b), 3-hydroxy-1,2,6,10-tetramethylundecyl hexzadecanoate (5a), 3-hydroxy-1,2,6,10-tetramethylundecyl (9E)-octadecaenoate (5b), and 3-hydroxy-1,2,6,10-tetramethylundecyl octadecanoate (5c). Antimicrobial activities of the isolates obtained from the YP9B strain were determined. Cytotoxic and antiviral activities were tested for the isolates against VERO, MCF-7, PC-3, and A549. Compounds 5a-c, 1, and 3a-c showed bacteriostatic activity at low concentrations, and 4a-b and 2 were found to be bactericides. MIC and MBC values against Mycobacterium smegmatis for the compounds 5a-c and 1 were determined to be ​​ <0.5 µg/mL and 0.46 µg/mL, respectively. The experimental result showed that compounds 2, 5a-c and 1 have strong cytotoxic (7.51±1.38 and 19.13± 0.68 (µM) IC50) activity. The antiviral activity against HSV type-1 was determined to be 1.25 µM for compounds 4a-c and 0.312 µM for compound 1.

Bright Side of Fusarium oxysporum: Secondary Metabolites Bioactivities and Industrial Relevance in Biotechnology and Nanotechnology

“…The nitrogen atom of pyridine ring is originated mainly from glutamine [191]. The formation of 2-Oxo-8-azatricyclo [9.3.1.1 3,7 ]-hexadeca-1(15),3( 16),4,6,11,13-hexaen-10-one (80) isolated from F. oxysporum, exhibited weak activity towards MCF-7, PC-3, and A549 and potent antimicrobial effect more than controls against various tested microorganisms with MIC values ranging from 0.8-12.5 µ g/mL [73] (Figure 7). Fusarioxazin (81) was separated from F. oxysporum associated with Vicia faba roots.…”

“…Nenkep et al, isolated a polycyclic quinazoline alkaloid, oxysporizoline (73), in addition to 1H-indol-3-butanamide (74) and butenolide (75) from marine-mudflat-derived F. oxysporum. Compounds 73 and 75 displayed weak antibacterial activity against MRSA (MIC 6.25 µ g/mL).…”

“…They also exhibited potent DPPH radical scavenging potential (IC50 10 and 12 µM, respectively) than ascorbic acid (IC50, 20 µM) [70] (Figure 6). Nenkep et al, isolated a polycyclic quinazoline alkaloid, oxysporizoline (73), in addition to 1H-indol-3-butanamide (74) and butenolide (75) from marine-mudflat-derived F. oxysporum. Compounds 73 and 75 displayed weak antibacterial activity against MRSA (MIC 6.25 µg/mL).…”

“…0.312 µM). Moreover, it had a powerful antibacterial potential (MICs 0.47-1.8 µg/mL) towards B. cereus, S. mutans, S. aureus, E. faecalis, and M. smegmatis[73].ungi 2021, 7, x FOR PEER REVIEW 53 of Phenolic and Aromatic Compounds Podophyllotoxin (151), an aryltetralin lignan was reported from F. oxysporum isolated from Juniperus recurva and quantified by HPLC, LC-MS, and LC-MS/MS[106] (Figure16). Kılıç et al, reported the isolation of 153 from F. oxysporum YP9B that displayed potent cytotoxic potential towards MCF-7, PC-3, and A549 (IC50 15.01, 19.13, and 17.06 µ M, respectively), compared to doxorubicin (IC50 0.053, 0.09, 17.75 µ M, respectively).…”

“…0.312 µ M). Moreover, it had a powerful antibacterial potential (MICs 0.47-1.8 µ g/mL) towards B. cereus, S. mutans, S. aureus, E. faecalis, and M. smegmatis[73].…”