The dark brown mixture resulting from the autooxidation of catechinic acid (CA) (AOCA) has been reported to possess antiviral activity against Herpes Simplex Virus 1 and 2 (HSV-1 and HSV-2). Unfortunately, the constituents of AOCA were not separated or identified and the compound(s) responsible for AOCA’s antiviral activity remained unknown until recently. Colorless 4-hydroxy benzoic acid (4-HBA) has been reported as the main constituent (75%) of AOCA, and as being responsible for its antiviral activity. The findings seem not to be reliable because of the existence in the literature of very different findings, the high concentration that was attributed to the supposed 4-HBA in the dark mixture, and the insufficient or inaccurately interpreted analytical experiments reported in the study identifying 4-HBA in AOCA. Of particular concern is the lack of AOCA chromatograms highlighting a peak attributable to 4-HBA, using commercial 4-HBA as a standard, and investigations concerning the antiviral activity of marketed 4-HBA. Therefore, in this study, to verify the exactness of the recent reports, we prepared CA from catechin and AOCA from CA, and the absence of 4-HBA in the mixture was first established by thin-layer chromatography (TLC), and then was confirmed by UHPLC–MS/MS, UV–Vis, and ATR–FTIR analyses. For further confirmation, the ATR–FTIR spectral data were processed by principal components analysis (PCA), which unequivocally established strong structural differences between 4-HBA and AOCA. Finally, while the antiviral effects of AOCA against HSV-2 were confirmed, a commercial sample of 4-HBA was completely inactive.

4-Hydroxybenzoic Acid as an Antiviral Product from Alkaline Autoxidation of Catechinic Acid: A Fact to Be Reviewed

Alfei, Silvana;Caviglia, Debora;Penco, Susanna;Zuccari, Guendalina;
2022

Abstract

The dark brown mixture resulting from the autooxidation of catechinic acid (CA) (AOCA) has been reported to possess antiviral activity against Herpes Simplex Virus 1 and 2 (HSV-1 and HSV-2). Unfortunately, the constituents of AOCA were not separated or identified and the compound(s) responsible for AOCA’s antiviral activity remained unknown until recently. Colorless 4-hydroxy benzoic acid (4-HBA) has been reported as the main constituent (75%) of AOCA, and as being responsible for its antiviral activity. The findings seem not to be reliable because of the existence in the literature of very different findings, the high concentration that was attributed to the supposed 4-HBA in the dark mixture, and the insufficient or inaccurately interpreted analytical experiments reported in the study identifying 4-HBA in AOCA. Of particular concern is the lack of AOCA chromatograms highlighting a peak attributable to 4-HBA, using commercial 4-HBA as a standard, and investigations concerning the antiviral activity of marketed 4-HBA. Therefore, in this study, to verify the exactness of the recent reports, we prepared CA from catechin and AOCA from CA, and the absence of 4-HBA in the mixture was first established by thin-layer chromatography (TLC), and then was confirmed by UHPLC–MS/MS, UV–Vis, and ATR–FTIR analyses. For further confirmation, the ATR–FTIR spectral data were processed by principal components analysis (PCA), which unequivocally established strong structural differences between 4-HBA and AOCA. Finally, while the antiviral effects of AOCA against HSV-2 were confirmed, a commercial sample of 4-HBA was completely inactive.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11567/1092096
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