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Nutrients
Feb 23, 2023;15 (5):

The Degree of Hydroxylation of Phenolic Rings Determines the Ability of Flavonoids and Stilbenes to Inhibit Calcium-Mediated Membrane Fusion.

Polina D Zlodeeva, Egor V Shekunov, Olga S Ostroumova, Svetlana S Efimova
Author Information
  1. Polina D Zlodeeva: Laboratory of Membrane and Ion Channel Modeling, Institute of Cytology of Russian Academy of Sciences, Tikhoretsky 4, 194064 Saint Petersburg, Russia. ORCID
  2. Egor V Shekunov: Laboratory of Membrane and Ion Channel Modeling, Institute of Cytology of Russian Academy of Sciences, Tikhoretsky 4, 194064 Saint Petersburg, Russia.
  3. Olga S Ostroumova: Laboratory of Membrane and Ion Channel Modeling, Institute of Cytology of Russian Academy of Sciences, Tikhoretsky 4, 194064 Saint Petersburg, Russia.
  4. Svetlana S Efimova: Laboratory of Membrane and Ion Channel Modeling, Institute of Cytology of Russian Academy of Sciences, Tikhoretsky 4, 194064 Saint Petersburg, Russia. ORCID
PMID: 36904120 DOI: 10.3390/nu15051121

Abstract

This paper discusses the possibility of using plant polyphenols as viral fusion inhibitors with a lipid-mediated mechanism of action. The studied agents are promising candidates for the role of antiviral compounds due to their high lipophilicity, low toxicity, bioavailability, and relative cheapness. Fluorimetry of calcein release at the calcium-mediated fusion of liposomes, composed of a ternary mixture of dioleoyl phosphatidylcholine, dioleoyl phosphatidylglycerol, and cholesterol, in the presence of 4'-hydroxychalcone, cardamonin, isoliquiritigenin, phloretin, resveratrol, piceatannol, daidzein, biochanin A, genistein, genistin, liquiritigenin, naringenin, catechin, taxifolin, and honokiol, was performed. It was found that piceatannol significantly inhibited the calcium-induced fusion of negatively charged vesicles, while taxifolin and catechin showed medium and low antifusogenic activity, respectively. As a rule, polyphenols containing at least two OH-groups in both phenolic rings were able to inhibit the calcium-mediated fusion of liposomes. In addition, there was a correlation between the ability of the tested compounds to inhibit vesicle fusions and to perturb lipid packing. We suggest that the antifusogenic action of polyphenols was determined by the depth of immersion and the orientation of the molecules in the membrane.

Keywords

catechin lipid vesicles lipid-packing stress membrane piceatannol polyphenol nutrients taxifolin viral fusion inhibitors

References

  1. Proc Natl Acad Sci U S A. 2010 Oct 5;107(40):17339-44 [PMID: 20823220]
  2. Biochem Pharmacol. 2006 Jul 14;72(2):217-26 [PMID: 16756964]
  3. Nutr Metab Cardiovasc Dis. 2018 Jul;28(7):691-697 [PMID: 29739677]
  4. J Toxicol. 2016;2016:7651047 [PMID: 26880913]
  5. Pharmacol Res. 2019 Jun;144:192-209 [PMID: 31002949]
  6. Respirology. 2008 Mar;13(2):203-14 [PMID: 18339017]
  7. Molecules. 2017 Mar 19;22(3): [PMID: 28335502]
  8. Dermatol Ther. 2022 Aug;35(8):e15658 [PMID: 35726011]
  9. J Antimicrob Chemother. 2007 Aug;60 Suppl 1:i57-8 [PMID: 17656384]
  10. Trends Plant Sci. 1999 Oct;4(10):394-400 [PMID: 10498963]
  11. J Membr Biol. 2018 Aug;251(4):551-562 [PMID: 29549386]
  12. Bioorg Med Chem Lett. 2014 May 1;24(9):2115-7 [PMID: 24704028]
  13. Chem Phys Lipids. 2018 Dec;217:35-42 [PMID: 30385272]
  14. Biomed Res Int. 2022 Jun 6;2022:5445291 [PMID: 35707379]
  15. Int J Antimicrob Agents. 2019 Jul;54(1):80-84 [PMID: 30930299]
  16. Med Microbiol Immunol. 2011 Feb;200(1):53-60 [PMID: 20865277]
  17. Annu Rev Nutr. 2001;21:381-406 [PMID: 11375442]
  18. Biochemistry. 1986 Nov 4;25(22):6978-87 [PMID: 3801406]
  19. Biol Chem. 2011 Oct;392(10):837-47 [PMID: 21823902]
  20. Soft Matter. 2016 Feb 21;12(7):2118-26 [PMID: 26745787]
  21. Crit Rev Food Sci Nutr. 2017 Apr 13;57(6):1280-1293 [PMID: 26565435]
  22. Biochem (Mosc) Suppl Ser A Membr Cell Biol. 2022;16(4):311-319 [PMID: 36532263]
  23. Poult Sci. 2022 Mar;101(3):101626 [PMID: 34995876]
  24. Int J Mol Sci. 2021 May 10;22(9): [PMID: 34068829]
  25. Biomed Pharmacother. 2021 Oct;142:112004 [PMID: 34388527]
  26. ACS Nano. 2021 Aug 24;15(8):12880-12887 [PMID: 34338519]
  27. Antiviral Res. 2011 Oct;92(1):45-56 [PMID: 21641936]
  28. Cancers (Basel). 2021 Jan 01;13(1): [PMID: 33401375]
  29. Plants (Basel). 2022 Apr 20;11(9): [PMID: 35567117]
  30. Curr Opin Food Sci. 2020 Apr;32:149-155 [PMID: 32923374]
  31. Nutrients. 2020 Aug 21;12(9): [PMID: 32825564]
  32. Appl Microbiol Biotechnol. 2019 Apr;103(7):2959-2972 [PMID: 30798357]
  33. Int J Mol Sci. 2020 May 29;21(11): [PMID: 32485905]
  34. J Ethnopharmacol. 2020 Dec 05;263:113163 [PMID: 32758575]
  35. Antiviral Res. 2021 Nov;195:105091 [PMID: 34044060]
  36. Genes Nutr. 2011 May;6(2):125-47 [PMID: 21484163]
  37. Life (Basel). 2022 Dec 29;13(1): [PMID: 36676048]
  38. Langmuir. 2016 Dec 13;32(49):13234-13243 [PMID: 27951697]
  39. Antioxidants (Basel). 2022 Jul 11;11(7): [PMID: 35883840]
  40. Phytother Res. 2022 Jan;36(1):266-278 [PMID: 34709675]
  41. Antiviral Res. 2005 Dec;68(3):124-34 [PMID: 16188329]
  42. Front Aging Neurosci. 2018 Nov 01;10:348 [PMID: 30443212]
  43. Langmuir. 2012 Jul 3;28(26):9908-14 [PMID: 22702338]
  44. Biotechnol Lett. 2012 May;34(5):831-8 [PMID: 22350287]
  45. Nat Med. 2008 Dec;14(12):1357-62 [PMID: 19029986]
  46. Curr Res Pharmacol Drug Discov. 2020 Dec 10;2:100008 [PMID: 34909644]
  47. Nutrients. 2022 Sep 02;14(17): [PMID: 36079895]
  48. Chem Phys Lipids. 2014 Feb;178:77-83 [PMID: 24361549]
  49. PLoS One. 2014 Sep 03;9(9):e105070 [PMID: 25184746]
  50. Biomedicines. 2021 Oct 10;9(10): [PMID: 34680551]
  51. Prev Nutr Food Sci. 2022 Dec 31;27(4):347-353 [PMID: 36721750]
  52. Planta Med. 2014 Feb;80(2-3):177-82 [PMID: 24458263]
  53. Arch Biochem Biophys. 2000 Jan 1;373(1):102-9 [PMID: 10620328]
  54. J Gen Virol. 2007 Mar;88(Pt 3):942-950 [PMID: 17325368]
  55. J Membr Biol. 2013 Dec;246(12):985-91 [PMID: 24129663]
  56. Biomed Pharmacother. 2021 Feb;134:111017 [PMID: 33338751]
  57. Am J Med. 2002 Dec 30;113 Suppl 9B:71S-88S [PMID: 12566142]
  58. Phytomedicine. 2021 May;85:153311 [PMID: 33067112]

Grants

  1. # 22-15-00417/This study was funded by the Russian Foundation of Science

MeSH Term

Flavonoids
Calcium
Catechin
Liposomes
Membrane Fusion
Hydroxylation
Stilbenes
Polyphenols
Lipids

Chemicals

Flavonoids
Calcium
3,3',4,5'-tetrahydroxystilbene
Catechin
Liposomes
Stilbenes
Polyphenols
Lipids
Journal Article

Word Cloud

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