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. 2022 Feb 7;8:777576. doi: 10.3389/fnut.2021.777576

Table 3.

Antiviral effect of FA derivatives.

Derivative General structure Virus Antiviral activity/Cytotoxicity of the compound Structure References
Chemically synthesized
FA polymers graphic file with name fnut-08-777576-i0001.jpg HIV-1 IC50 = 1.0 μg/ml
IC50 = 0.9 μg/ml
IC50 = 2.7 μg/ml
IC50 = 3.2 μg/ml
>30 kDa
30–10 kDa
10–1 kDa
1 kDa−500 Da
(104)
Example: diferulate, triferulate
FA amide of 3-aminomethyl glaucine graphic file with name fnut-08-777576-i0002.jpg HRV-14 IC50 = 12.00 μM
CC50= 113 μM
- (105)
FA amides graphic file with name fnut-08-777576-i0003.jpg TMV 40.7% protective effect
46.4% curative effect
R1: n-Pr;
R2: H
R3: propynyl
(106)
Hydrogenated FA amides graphic file with name fnut-08-777576-i0004.jpg TMV 27.3% protective effect
30.4% curative effect
R1: Me
R2: p-Cl
R3: propynyl
(106)
graphic file with name fnut-08-777576-i0005.jpg TMV 15.2% protective effect
28.9% curative effect
R1: p-benzyloxy
R2: propynyl
(107)
α,β-unsaturated amide derivatives of FA with an α-aminophosphonate moiety graphic file with name fnut-08-777576-i0006.jpg TMV EC50 = 180.37 μg/ml (protective effect) R1: 4-Cl (108)
EC50 = 285.42 μg/ml (curative effect) R2: 4-CF3-Ph
CMV EC50 = 216.30 μg/ml (protective effect)
EC50 = 284.67 μg/ml (curative effect)
Trans-FA derivatives containing acylhydrazone moiety graphic file with name fnut-08-777576-i0007.jpg TMV 18.8% curative effect R1: PhCH2 (109)
23.0% protective effect R2: 2-Th
94.2% inactivating effect
EC50 = 36.59 μg/ml
FA sulfonamides graphic file with name fnut-08-777576-i0008.jpg TMV 39.8% curative effect R1: -C2H5 (110)
59.7% protective effect
87.3% inactivating effect
R2: 4-NO2-Ph
EC50 = 84.80 μg/ml
Myricetin derivatives with an FA amide scaffold graphic file with name fnut-08-777576-i0009.jpg TMV 55.5% curative effect
53.3% protective effect
EC50 = 472.4 μg/ml
R: 4-Br, n = 3 (111)
FA 3-amino derivatives/esters graphic file with name fnut-08-777576-i0010.jpg H1N1 IC50 =90.0 μg/ml R1: CH2(CH3) (78)
R2: CH(CH3)2
R3: NO2
FA derivatives with a quinazoline moiety graphic file with name fnut-08-777576-i0011.jpg TMV 60.8% curative effect R1: 2-OCH3-Ph (112)
78.2% protective effect R2: 4-oxoquinazolin-3(4H)-yl-methyl
90.8% inactivating effect
CMV 58.1% curative effect R1: 2-OCH3-4-allyl-Ph
69.8% protective effect
R2:4-oxoquinazolin-3(4H)-yl-methyl
78.2% inactivating effect
Trans-FA esters with a chalcone group graphic file with name fnut-08-777576-i0012.jpg TMV 63.9% curative effect R: Me (113)
64.6% protective effect Ar: 2-F-Ph
92.3% inactivating effect
EC50 = 214.20 μg/ml
FA derivatives containing dithioacetal moiety graphic file with name fnut-08-777576-i0013.jpg TMV 62.7% curative effect R1: 3-OCH3-4-OCOCH3 (114)
52.3% protective effect
73.8% inactivating effect R2: 2-OCH3
EC50=73.7 μg/ml R3: -(CH2)2OH
graphic file with name fnut-08-777576-i0014.jpg TMV 62.5% curative effect R1: 3-OCH3-4-OCOCH3
61.8% protective effect R2: H
R3: -(CH2)2OH
83.5% inactivating effect
EC50= 50.7 μg/ml
graphic file with name fnut-08-777576-i0015.jpg TMV 48.% curative effect R1: H
48.% protective effect R2:H
53.% inactivating effect
EC50=355.6 μg/ml
Enzymatically synthesized
FA rutinoside graphic file with name fnut-08-777576-i0016.jpg FCV 40% increase of cell viability (117)
FA β-sitosterol ester graphic file with name fnut-08-777576-i0017.jpg SARS-CoV-2 Binding energy = −7.8 kcal/mol (molecular docking simulation with SARS-CoV-2 3CLpro) (127)
(128)

HIV, human immunodeficiency virus; HRV, human rhinovirus; TMV, tobacco mosaic virus; CMV, cucumber mosaic virus; H1N1, influenza A virus subtype; FCV, feline calicivirus; SARS-CoV-2, severe acute respiratory syndrome coronavirus; EC50, half-maximal effective concentration; the concentration required to obtain a 50% inhibitory effect; IC50, half-maximal inhibitory concentration; the concentration at which the number of viral plaques is reduced by 50%; CC50, half-maximal cytotoxicity concentration, the concentration that reduced cell viability to 50% of the control.