Antioxidant, antimicrobial and antiproliferative activities of fungal metabolite produced by <i>Aspergillus flavus</i> on <i>in vitro</i> study

ALMANAA, Taghreed N.; RABIE, Gamal; El-MEKKAWY, Rasha M.; YASSIN, Marwa A.; Saleh, Noha; EL-Gazzar, Nashwa

doi:10.1590/fst.01421

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Original Article • Food Sci. Technol (Campinas) 42 • 2022 • https://doi.org/10.1590/fst.01421 linkcopy

Antioxidant, antimicrobial and antiproliferative activities of fungal metabolite produced by Aspergillus flavus on in vitro study

Authorship SCIMAGO INSTITUTIONS RANKINGS

Regarding to the defiance came upon scientists to output natural products with potent biological activity from cheap sources and in an attempt to recover the average of antiproliferative agents, the employment of fungal metabolite in creating a cordial proper process was a prerequisite. In the present results, fungal metabolites were detected by thin layer chromatography. One fungal isolate out of ten isolates bioassayed, was showed to have the most potent antioxidant, antiproliferative and antimicrobial activity; this fungal isolate was identified as belonging to Aspergillus flavus (A. flavus). Fungal extract of A. flavus showed a high free radical scavenging activity using Diphenyl-1-picrylhydrazyl (DPPH) scavenging % with low a concentration of IC₅₀ and potent flavonoid content. The result of instrumental analysis using GC.Mass illustrates the presence of different potent products of A. flavus extract. In addition, A. flavus extract showed a promising antiproliferative activity. Inhibitory activity against Hepatocellular carcinoma cells was detected under these experimental conditions. This strategy can be further used to elicit new age drugs.

Keywords:
Aspergillus flavus; bioactive compounds; GC; DPPH; antibacterial; antifungal

No.	Fungal isolates	DPPH scavenging %		Flavonoid content
No.	Fungal isolates	Intra.	Extra.	Flavonoid content (μg/mg quercetin)
1	Aspergillus flavus	61.5 ± 1.15	81.4 ± 0.60	469 ± 1.25
2	Aspergillus fumigatus	-	48.9 ± 1.19	367 ± 1.22
3	Aspergillus terrus	21.1 ± 0.55	68.2 ± 1.19	332 ± 1.2
4	Penicillium chrysogenum.	-	22.9 ± 1.31	182 ± 1.19
5	Fusarium moniliform	-	17.6 ± 0.52	134 ± 0.85
6	Fusarium oxysporium	-	11.8 ± 0.45	129 ± 0.85
7	Penicillium citrinum.	-	21.6 ± 0.16	178 ± 1.19
8	Aspergillus flavups	15.9 ± 0.56	33.3 ± 0.76	166 ± 0.65
9	Trichoderma sp	49.6 ± 0.55	79.1 ± 0.56	221 ± 0.45
10	Aspergillus oryza	19.2 ± 0.60	42.5 ± 0.45	218 ± 0.45

Sample conc. (µg/mL)	DPPH scavenging %	Flavonoid content (µg/mg quercetin)
640	77.44^a ± 7.44	121^a ± 1.21
320	64.33^b ± 4.33	116^b ± 1.12
160	53.11^c ± 3.11	101^c ± 1.0
80	42.22^d ± 1.89	78^d ± 1.0
40	36.56^d ± 6.00	53^e ± 0.85
20	18.33^e ± 3.33	33^f ± 0.85
10	9.33^f ± 0.33	16^g ± 1.19
5	7.59^f ± 1.59	11^g ± 0.65
0	0 ± 0.00	0 ± 0.00

Sample conc. (µg/mL)	DPPH scavenging %
40	92.48^a ± 2.48
35	87.53^b ± 5.00
30	80.65^c ± 3.00
25	77.41^c ± 2.00
20	70.94^d ± 0.94
15	54.86^e ± 3.00
10	17.49^f ± 0.49
5	11.78^g ± 1.78
0	0^h ± 0.00

Tested bacteria	Sample code	Control
Tested bacteria	Sample code	Gentamycin
Gram Positive bacteria	Inhibition zone (mm)
Staphylococcus aureus (DSM1104)	16^b ± 2.00	23
Streptococcus pyogenes Atcc19615	19^ab ± 3.00	25
Gram negative bacteria
Pseudomomas aeruginosa LMG8629	24^a ± 4.00	16
Escherichia coli (LMG8223)	20^ab ± 1.00	29

Tested fungi	Sample	Control
Tested fungi	Inhibition Zone(mm)	Control
Fusarium oxysporirum	28^a ± 2.00	25
Candida albicans	15^b ± 3.00	20

Sample conc. (µg/mL)	Viability %	Inhibitory %	S.D. (±)
500	14.69	85.31	1.82
250	26.71	73.29	0.97
125	39.65	60.35	3.41
62.5	79.21	20.79	2.78
31.25	93.82	6.18	0.96
15.6	99.43	0.57	0.43
7.8	100	0
3.9	100	0
0	100	0

No.	Retention Time(Rt)	M.formula	M.W.	Compound name and structure	Area	Parent ion (M⁺)	Base Peak (m/e) (100%)	Biological activity
1	5.71	C₇H₁₀O2	126.0	2,4-HEXADIENOIC ACID, METHYL ESTER	3.15	126.0	67.00	Anticancer& Antioxidant, Kim et al. (2015).
2	7.31	C₁₆H₁₆O	224.0	1,4-DIPHENYLBUT-3-ENE-2-OL	0.60	224.0	207.0	Anticancer& Antioxidant, Mou et al. (2013)
3	7.31	C₁₁H₁₅NO2S	225.0	2-THIOPHENEETHANOL,5-(4,5-DIHYDRO-4,4-DIMETHYL-2-OXAZOLYL-	0.60	225.0	207.0	Anticancer & Antioxidant, Karakuş et al. (2018)
4	17.22	C₁₄H₂₂O	206.0	Phenol, 2,4-Bis(1,1-DIMETHYLETHYL)_	5.18	206.0	191.0	Anticancer& Antioxidant, Kim et al. (2015) Govindappa et al. (2017)
5	20.89	C₁₅H₂₄O	220.0	Caryophylla-4(2),8(13)-dien-5a-ol	1.41	220.0	136.0	Anticancer, Qsar (41); Al-Romaizan et al. (2019)
6	21.95	C₁₈H₁₆O₇	344.0	4H-1-BENZOPYRAN-4-ONE,2-(3,4-DIMETHOXYPHENYL)-3,5-DIHYDROXY-7-METHOXY-	11.57	344.0	57.0	Antioxidant, Tamil et al. (2017),; Al-Mohammadi et al. (2020),
7	23.53	C₂₉H₄₃NO₃Si	481.0	ANDROSTANE-11,17-DIONE,3-[(TRIMETHYLE SILYL) OXY]-17-[O-(PHENYLMETHYL)OXIME],(3a,5a)	0.83	481.0	73.0	Anticancer & Antioxidant, Purnamasari et al. (2019) ; Jelena & Maja (2015) ; Yadav et al. (2018),
8	23.68	C₁₂H₁₈O₂	194.0	Tricyclo[4,3,1,1(3,8)]undecane-3-carboxylic acid	0.84	194.0	149.0	Anticancer, Jelena & Maja (2015)
9	23.87	C₂₄H₃₄O₅	402.0	1,2,3,4,4a,5,6,7,8,8a,9- Dodecahydrophenanthren-9-one,2-acetoxy-7-methylene-1,1,4a-trimethyl-8-(2-methoxycarbonylethyl)-	1.40	402.0	43.0	Anticancer & Antioxidant (Purnamasari et al., 2019)
10	24.05	C₂₃H₃₂O	324.0	2-[4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hexa-1,3,5-trienyl]cyclohex-1-en-1-carboxaldehde	2.18	324.0	43.0	Anticancer & Antioxidant, Karakuş et al. (2018)
11	24.61	C₁₇H₃₄O₂	270.0	Hexadecanoic acid, methyl ester	37	270.0	74.0 & 87.0	Anticancer& Antioxidant, Narra et al. (2017),
12	25.70	C₁₈H₃₆O₂	284.0	Pentadecanoic acid, 14 methyl-, ethyl ester	4.23	284.0	88.0	Anticancer& Antioxidant, Narra et al. (2017),
13	26.18	C₃₂H₅₈OSi	486.0	Silane, trimethyl (stigmast-5-en-3beta-yloxy)-	4.87	486.0	73.0	Antioxidant activity, Yadav et al. (2018),
14	26.18	C₃₀H₅₃NO₄Si	519.0	Glycine, N-[(3alpha,5beta)-24-oxo-3-[(trimethyl silyl) oxy]cholan-24-yl]-, methyl ester	2.82	519.0	131.0	Antioxidant activity, Yadav et al. (2018),
15	26.73	C₃₀H₅₂O₂	444.0	2,6,10,15,19,23-hexamethyl-2,6,14,18,22-tetracosapentaene-10,11-diol	5.62	444.0	69.0	Antioxidant, Srivastava et al. (2015),
16	26.73.	C₂₃H₃₈O₂	346.0	6,9,12,15-Docosatetraenoic acid, methyl ester	2.81	346.0	69.0	Antioxidant (Srivastava et al. (2015),
17	27.34	C₁₉H₃₆O₂	296.0	9-octadecenoic acid, methyl ester, (E)-	19.26	296.0	55.0	Antioxidant (Narra et al. (2017)
18	27.44	C₂₇H₁₀₄O₆	884.0	9-Octadecenoic acid,1,2,3-propanetriyl ester, (E,E,E)	1.77	884.0	55.0	Antioxidant (Srivastava et al. (2015),
19	27.64	C₂₇H₄₀O₄	428.0	Spirost-8-en-11-one,3-hydroxy-,(3a,5a,14a,20a,22a,25R)	1.99	428.0	314.0	Anticancer, antibacterial and antioxidant (Lu et al. (2015)
20	27.74	C₁₉H₃₈O₂	298.0	Heptadecanoic acid, 16-methyl-, methyl ester	13	298.0	74.0	Antioxidant (Naganna et al.,
21	28.34	C₂₉H₅₀O2	430.0	Cholestan-3-ONE,Cyclic 1,2-Ethanediyl Aetal,*(5 a)-	2.62	430.0	99.0	Anticancer & Antioxidant (Sisa et al. (2003)
22	31.28	C18H24	240.0	Cyclohexane, hexaethyllidene-(isomer 1)	2.62	240.0	196.0	Anticancer, Zheng et al. (2018); Karakuş et al. (2018),
23	31.28	C₁₉H₂₄N₂	280.0	Curan, 16,17-didehydro-,(20.xi.)-	2.62	280.0	55.0	Anticancer (Mou et al. (2013)
24	35.36	C24H38O4	390.0	Bis(2-ETHYLHEXYL)PHTHALATE	6.68	390.0	149.0	Antioxidant Lemoreaux
25	38.25	C₂₁H₁₈O₆	366.0	9-Carbomethyl-6,11-DIMETHOXY-5-OXO-9,10-DIHydroXANTHO[3,2-G]NAPHTHALENE	29.72	366.0	307.0	Anticancer, Zheng et al.,2018)
26	38.25	C₁₉H₃₃NO₂	307.0	12-ACETYLAMINO-15,16,17-TRINORLABDAN-8-ONE	59.44	307.0	292.0	Anticancer and antimicrobial, El-Sayed et al. (2020), ; Popova et al. (2009),

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[1] Values with different superscripts within rows are significantly different (P < 0.05).