Antiviral Activity of Red Propolis Against Herpes Simplex Virus-1

Negri, Giuseppina; Duarte-Almeida, Joaquim Maurício; Figueiredo, Cristina Adelaide; Toledo-Piza, Ana Rita de; Tonelli, Flávia Cristina Policarpo; Barbosa, Tamyris Fernanda; Mendonça, Ronaldo Zucatelli

doi:10.1590/s2175-97902024e23746

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Brazilian Journal of Pharmaceutical Sciences

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Article • Braz. J. Pharm. Sci. 60 • 2024 • https://doi.org/10.1590/s2175-97902024e23746 copy

Antiviral Activity of Red Propolis Against Herpes Simplex Virus-1

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Brazilian Red Propolis is a resinous material produced by Apis mellifera bees through the collection of the exudates of Dalbergia ecastaphyllum , rich in flavonoids, and Symphonia globulifera and Clusia species, which are rich in polyprenylated benzophenones. More than 200 compounds, including flavonoids and polyprenylated benzophenones have been found in Brazilian red propolis. The objective of the present study was to evaluate the chemical composition and antiviral activity of an ethanolic extract of red propolis from Alagoas, Brazil, against Herpes Simplex Virus (HSV-1). In the HPLC-PDA-ESI-MS/MS analysis were detected flavanones, isoflavones, chalcones, pterocarpans and polyprenylated benzophenones. The measurement of antiviral activity of red propolis extract was performed by DNA quantification through quantitative real-time PCR assay and negative staining Electron Microscopy. The pretreatment, post-treatment, and virucide assays using ethanolic extract of red propolis with concentration of 8, 12, 24, 48, or 96 µ g/mL, indicated an inhibition of the viral binding and viral entry into cells as well as the replication of HSV-1. In the electron microscopy imaging was observed the disruption of the viral membrane in the HSV-1 treated with red propolis, when compared with HSV-1 that was treated with phosphate buffered saline alone, indicating that ethanolic extract from red propolis can act directly on the viral envelope, through lipid membrane degradation and/or directly blocking the enriched proteins on the viral surface.

Keywords:
Antiviral activity; Red propolis; Apis mellifera ; Herpes Simplex Virus-1; Flavonoids; Polyprenylated benzophenones

Comp. no	RT Min	UV λ _{max - nm}	HPLC-PAD-ESI-MS/MS m/z (% base peak) [M - H] ^-	Proposed structure	References
1	22.8	289, 313sh	[M - H] ^- - 331 MS/MS – 313 (60), 177 (100)	3,3',5-trihydroxy-4',7-dimethoxy flavanone	Yen et al ., 2012, Vieira de Moraes et al. , 2021
2	24.5	289, 313sh	[M - H] ^- - 301 MS/MS – 283 (100), 177 (50)	3,3',5-trihydroxy-4'-methoxy flavanone	Yen et al. , 2012, Vieira de Moraes et al. , 2021
3	27.6	280, 314sh	[M - H] ^- - 255 MS/MS - 135	liquiritigenin – (4',7-dihydroxy flavanone)	Silva et al. , 2020Silva VC, Silva AMGS, Basílio JAD, Xavier JA, Do Nascimento TG, Naal RMZG, et al. New Insights for Red Propolis of Alagoas—Chemical Constituents, Topical Membrane Formulations and Their Physicochemical and Biological Properties. Molecules. 2020;25:5811.
4	28.6	249, 291sh	[M - H] ^- - 313	5,7-dihydroxy-3',4’-dimethoxy isoflavone	Vieira de Moraes et al. , 2021Vieira De Morais D, Rosalen PL, Ikegaki M, De Souza Silva AP, Massarioli AP, De Alencar SM. Active Antioxidant Phenolics from Brazilian Red Propolis: An Optimization Study for Their Recovery and Identification by LC-ESI- QTOF-MS/MS. Antioxidants. 2021;10:297.
5	29.5	254	[M - H] ^- - 283	calycosin – (3'-hydroxy formononetin)	Vieira de Moraes et al. , 2021Vieira De Morais D, Rosalen PL, Ikegaki M, De Souza Silva AP, Massarioli AP, De Alencar SM. Active Antioxidant Phenolics from Brazilian Red Propolis: An Optimization Study for Their Recovery and Identification by LC-ESI- QTOF-MS/MS. Antioxidants. 2021;10:297. , Silva et al. , 2020Silva VC, Silva AMGS, Basílio JAD, Xavier JA, Do Nascimento TG, Naal RMZG, et al. New Insights for Red Propolis of Alagoas—Chemical Constituents, Topical Membrane Formulations and Their Physicochemical and Biological Properties. Molecules. 2020;25:5811. , Bankova et al. , 2019Bankova V, Galabov AS, Antonova D, Vilhelmova N, Di Perri B. Chemical composition of Propolis Extract ACF® and activity against herpes simplex virus. Phytomedicine, 2014;21:1432-1438.
6	30.2	300sh, 370	[M - H] ^- - 271 MS/MS - 151	2’,3’,4, 6’-tetrahydroxy chalcone	Ferreira et al. , 2017
7	31.3	265	[M - H] ^- - 283	biochanin A – (5,7-dihydroxy-4'-methoxy isoflavone)	Silva et al. , 2020Silva VC, Silva AMGS, Basílio JAD, Xavier JA, Do Nascimento TG, Naal RMZG, et al. New Insights for Red Propolis of Alagoas—Chemical Constituents, Topical Membrane Formulations and Their Physicochemical and Biological Properties. Molecules. 2020;25:5811.
8	32.8	300sh, 365	[M - H] ^- - 271 MS/MS – 135 (50), 109 (100)	2’,3,4,4’-tetrahydroxy chalcone	Righi et al. , 2011Righi AA, Alves TR, Negri G, Marques LM, Breyer H, Salatino A. Brazilian red propolis: unreported substances, antioxidant and antimicrobial activities. J Sci Food Agric. 2011;91:2363-2370.
9	33.5	300sh, 370	[M - H] ^- - 255 MS/MS - 135	isoliquiritigenin – (4,2',4'-trihydroxy chalcone)	Vieira de Morais et al. , 2021Vieira De Morais D, Rosalen PL, Ikegaki M, De Souza Silva AP, Massarioli AP, De Alencar SM. Active Antioxidant Phenolics from Brazilian Red Propolis: An Optimization Study for Their Recovery and Identification by LC-ESI- QTOF-MS/MS. Antioxidants. 2021;10:297. Silva et al. , 2020Silva VC, Silva AMGS, Basílio JAD, Xavier JA, Do Nascimento TG, Naal RMZG, et al. New Insights for Red Propolis of Alagoas—Chemical Constituents, Topical Membrane Formulations and Their Physicochemical and Biological Properties. Molecules. 2020;25:5811.
10	33.9	290	[M - H] ^- - 271	vestitol – (2',7-dihydroxy-4'-methoxy isoflavan)	Silva et al. , 2020Silva VC, Silva AMGS, Basílio JAD, Xavier JA, Do Nascimento TG, Naal RMZG, et al. New Insights for Red Propolis of Alagoas—Chemical Constituents, Topical Membrane Formulations and Their Physicochemical and Biological Properties. Molecules. 2020;25:5811.
11	35.3	290	[M - H] ^- - 255	demethyl medicarpin	Vieira de Morais et al. , 2021Vieira De Morais D, Rosalen PL, Ikegaki M, De Souza Silva AP, Massarioli AP, De Alencar SM. Active Antioxidant Phenolics from Brazilian Red Propolis: An Optimization Study for Their Recovery and Identification by LC-ESI- QTOF-MS/MS. Antioxidants. 2021;10:297.
12	36.5	290	[M - H] ^- - 283	homopterocarpin – (3,9-dimethoxy pterocarpan)	Silva et al., 2020Silva VC, Silva AMGS, Basílio JAD, Xavier JA, Do Nascimento TG, Naal RMZG, et al. New Insights for Red Propolis of Alagoas—Chemical Constituents, Topical Membrane Formulations and Their Physicochemical and Biological Properties. Molecules. 2020;25:5811. Vieira de Morais et al. , 2021Vieira De Morais D, Rosalen PL, Ikegaki M, De Souza Silva AP, Massarioli AP, De Alencar SM. Active Antioxidant Phenolics from Brazilian Red Propolis: An Optimization Study for Their Recovery and Identification by LC-ESI- QTOF-MS/MS. Antioxidants. 2021;10:297.
13	38.0	290	[M - H] ^- - 285 MS/MS – 149 (50), 123 (100)	7,3’-dihydroxy-4’-methoxy-8-methylflavan	Silva et al., 2020Silva VC, Silva AMGS, Basílio JAD, Xavier JA, Do Nascimento TG, Naal RMZG, et al. New Insights for Red Propolis of Alagoas—Chemical Constituents, Topical Membrane Formulations and Their Physicochemical and Biological Properties. Molecules. 2020;25:5811. Vieira de Moraes et al. , 2021Vieira De Morais D, Rosalen PL, Ikegaki M, De Souza Silva AP, Massarioli AP, De Alencar SM. Active Antioxidant Phenolics from Brazilian Red Propolis: An Optimization Study for Their Recovery and Identification by LC-ESI- QTOF-MS/MS. Antioxidants. 2021;10:297.

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