Chapter Two - Propolis flavonoids and terpenes, and their interactions with model lipid membranes: a review
Section snippets
List of abbreviations
- DODAB
Dioctadecyldimethylammonium bromide
- DOPC
Dioleoylphosphatidylcholine
- DOPE
Dioleoylphosphatidylethanolamine
- DPPC
Dipalmitoylphosphatidylcholine
- DPPE
Dipalmitoylphosphatidylethanolamine
- DPPG
Dipalmitoylphosphatidylglycerol
- DPPS
Dipalmitoylphosphatidylserine
- POPC
1-palmitoyl-2-oleoylphosphatidylcholine
- POPE
1-palmitoyl-2-oleoylphosphatidylethanolamine
- POPS
1-palmitoyl-2-oleoylphosphatidylserine
- SOPS
1-stearoyl-2-oleoylphosphatidylserine
Propolis definition, its history and its characteristics
Propolis, or “bee glue”, is a sticky, hydrophilic, gummy and resinous material that is produced by different species of bees, including honeybees (Apis spp.) and stingless bees (Melipona spp.). Its name derives from the Hellenistic Ancient Greek meaning “suburb/bee glue” or “defense of the city”, depending on the interpretation. Bees use it to seal cracks in their hives, to smooth the internal walls, and to protect the hive against intruders. Propolis also acts as a natural antibiotic, to
Artificial lipid membranes
The basic structural unit of biological membranes is the lipid bilayer. Lipid bilayers are sheet-like assemblies of countless amphiphilic lipid molecules where their structural arrangement is held together by hydrophobic interactions. These lipid bilayers form the boundary between the inner and outer cellular environments, as the plasma membrane, which effectively defines the cell; within the cell, lipid bilayers also define the intracellular organelles [10]. The plasma membrane contains lipids
Conclusions
Flavonoids and terpenes are the most biologically important constituents of propolis, and because of their broad spectrum of activities, they have been well studied. Most of these form strong interactions with different types of membranes, from artificial membranes composed of lipids with unsaturated and saturated chains, to cell ghosts, organelle membranes, and bacterial and fungal cells. In general, the flavonoids and terpenes fluidify membranes with saturated chains and membranes with lipids
References (112)
- et al.
Signaling from the living plasma membrane
Cell
(2011) - et al.
Key role of lipids in heat stress management
FEBS Lett.
(2013) - et al.
Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis
Phytochemistry
(2014) Review of the biological properties and toxicity of bee propolis (propolis)
Food Chem. Toxicol.
(1998)- et al.
Characterization and biological evaluation of selected Mediterranean propolis samples. Is it a new type?
LWT - Food Sci. Technol.
(2016) Chemical diversity of propolis and the problem of standardization
J. Ethnopharmacol.
(2005)- et al.
Analysis of the polyphenolic fraction of propolis from different sources by liquid chromatography-tandem mass spectrometry
J. Pharmaceut. Biomed.
(2007) - et al.
Terpenes with antimicrobial activity from Cretan propolis
Phytochemistry
(2009) - et al.
Chemical profile and anti-leishmanial activity of three Ecuadorian propolis samples from Quito, Guayaquil and Cotacachi regions
Fitoterapia
(2017) - et al.
Antioxidant activity of propolis of various geographic origins
Food Chem.
(2004)
New anti-trypanosomal active prenylated compounds from African propolis
Phytochem. Lett.
A review on phospholipids and their main applications in drug delivery systems
Asian J. Pharm. Sci.
Interactions of ρ-coumaric, caffeic and ferulic acids and their styrenes with model lipid membranes
Food Chem.
The role of membrane structure and function in cellular aging: a review
Mech. Ageing Dev.
Structure-dependent membrane interaction of flavonoids associated with their bioactivity
Food Chem.
Lipid bilayer pre-transition as the beginning of the melting process
Biochim. Biophys. Acta
Localization and interaction of hydroxyflavones with lipid bilayer model membranes: a study using DSC and multinuclear NMR
Eur. J. Med. Chem.
The uncoupling efficiency and affinity of flavonoids for vesicles
Biochem. Pharmacol.
Characterization of flavonoid–biomembrane interactions
Arch. Biochem. Biophys.
Permeability characteristics and membrane affinity of flavonoids and alkyl gallates in Caco-2 cells and in phospholipid vesicles
Arch. Biochem. Biophys.
Effect of flavonoid structure on the fluidity of model lipid membranes
Food Chem.
Medicinal chemical properties of successful central nervous system drugs, NeuroRx
J. Amer. Soc. Exper. NeuroTherapeut.
Flavonoids and cell membrane fluidity
Food Chem.
Interaction of the antioxidant flavonoid quercetin with planar lipid bilayers
Int. J. Pharm. (Amst.)
Effect of flavonoids on the Aβ (25-35)-phospholipid bilayers interaction
Eur. J. Med. Chem.
Flavonoids as antioxidant agents: importance of their interaction with biomembranes
Free Radical Biol. Med.
Unique uptake and transport of isoflavone aglycones by human intestinal Caco-2 cells: comparison of isoflavonoids and flavonoids
J. Nutr.
Modification of membranes by quercetin, a naturally occurring flavonoid, via its incorporation in the polar head group
Biochim. Biophys. Acta
The study of the quercetin action on human erythrocyte membranes
Biochem. Pharmacol.
Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1
Biochem. Pharmacol.
In-vitro anti-proliferative and anti-oxidant activity of galangin, fisetin and quercetin: role of localization and intermolecular interaction in model membrane
Eur. J. Med. Chem.
The interaction of flavonoids with mitochondria: effects on energetic processes
Chem. Biol. Interact.
Characteristics of quercetin interactions with liposomal and vacuolar membranes
Biochim. Biophys. Acta
Kaempferol and quercetin interactions with model lipid membranes
Food Res. Int.
Spin-label studies on phosphatidylcholine-cholesterol membranes: effects of alkyl chain length and unsaturation in the fluid phase
Biochim. Biophys. Acta Biomembr.
Modulation of liposomal membrane fluidity by flavonoids and isoflavonoids
Arch. Biochem. Biophys.
Antimicrobial mechanism of flavonoids against Escherichia coli ATCC 25922 by model membrane study
Appl. Surf. Sci.
FTIR, (1)H NMR and EPR spectroscopy studies on the interaction of flavone apigenin with dipalmitoylphosphatidylcholine liposomes
Biochim. Biophys. Acta
Investigation of the membrane localization and distribution of flavonoids by high-resolution magic angle spinning NMR spectroscopy
Biochim. Biophys. Acta
Estimation of the location of natural α-tocopherol in lipid bilayers by 13C-NMR spectroscopy
Biochim. Biophys. Acta Biomembr.
α-Tocopherol interacts with natural micelle-forming single-chain phospholipids stabilizing the bilayer phase
Arch. Biochem. Biophys.
The interaction of eugenol with cell membrane models at the air-water interface is modulated by the lipid monolayer composition
Biophys. Chem.
The Cell: A Molecular Approach
Biomembranes: Molecular Structure and Function
Molecular Cell Biology
Life: The Science of Biology
Membrane lipids and cell signaling
Curr. Opin. Lipidol.
Cited by (9)
Unraveling the antibacterial mechanism of 3-carene against Pseudomonas fragi by integrated proteomics and metabolomics analyses and its application in pork
2022, International Journal of Food MicrobiologyCitation Excerpt :However, 3-carene does not have any OH groups, just like limonene. Recent studies suggested that limonene hardly reacted with the polar lipid head groups but rapidly entered the hydrophobic core of the membrane, where it formed van der Waals interactions with the acyl chain of the lipids (Šturm and Ulrih, 2020). Hence, we speculated that the interaction mechanism between 3-carene and the membrane was similar to that of limonene.
Interactions of (−)-epigallocatechin-3-gallate with model lipid membranes
2022, Biochimica et Biophysica Acta - BiomembranesCitation Excerpt :Since the researchers proved, that EGCG incorporates in the membrane mostly with its galloyl moiety and B ring [21,25,27], that EGCG molecules can self-aggregates in the solution [24], and that flavonoids are too small, unlike tannins, to form a bridge between two membranes [45], it is very likely that EGCG incorporates into one bilayer of the liposome and then forms H-bonds with other EGCG molecules incorporated into different liposome. This is most probably due to specific structure of EGCG, since EGCG includes an addition galloyl group (Fig. 8), which is lacking in most other flavonoids [46]. Not only does the galloyl group add additional surface area to the molecule, it also adds additional OH groups (Fig. 8), which enables the formation of more bonds.
Synthesis and antimicrobial activity of new thiomonoterpene carboxylic acids
2024, Russian Chemical BulletinMonoterpene Thiols: Synthesis and Modifications for Obtaining Biologically Active Substances
2023, International Journal of Molecular SciencesCorrelation between total phenolic and flavonoid contents and biological activities of 12 ethanolic extracts of Iranian propolis
2023, Food Science and Nutrition