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Article ; Online: Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines.

Krompiec, Stanisław / Lodowski, Piotr / Kurpanik-Wójcik, Aneta / Gołek, Bogumiła / Mieszczanin, Angelika / Fijołek, Aleksandra / Matussek, Marek / Kaszuba, Klaudia

Molecules (Basel, Switzerland)

2023 Volume 28, Issue 6

Abstract: The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines ... ...

Abstract	The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH
Language	English
Publishing date	2023-03-10
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules28062547
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Article ; Online: Electroactive Dyes Based on 1,8-Naphthalimide with Acetylene Linkers as Promising OLED Materials - the Relationship Between Structure and Photophysical Properties.

Matussek, Marek / Kurpanik-Wójcik, Aneta / Gogoc, Szymon / Fijołek, Aleksandra / Filapek, Michał / Naumczuk, Beata / Data, Przemysław

Chemistry (Weinheim an der Bergstrasse, Germany)

2023 Volume 29, Issue 61, Page(s) e202302115

Abstract: Four A-π-D-π-A type small organic molecules with 1,8-naphthalimide motifs were successfully synthesised. The designed compounds are built of two 1,8-naphthalimide units linked via ethynyl π-linkages with selected functionalised donor motifs i. e. 2,2'- ... ...

Abstract	Four A-π-D-π-A type small organic molecules with 1,8-naphthalimide motifs were successfully synthesised. The designed compounds are built of two 1,8-naphthalimide units linked via ethynyl π-linkages with selected functionalised donor motifs i. e. 2,2'-bithiophene, fluorene, phenothiazine and carbazole derivative. The synthesis based on Sonogashira cross-coupling allowed us to obtain the presented dyes with good yields. The resulting symmetrical small molecules' optical, electrochemical and thermal properties were thoroughly investigated, and their potential applicability for the OLED devices was demonstrated. In addition, the relationship between molecular structure and properties was considered by employing experimental and theoretical studies. As a result of using various donor groups, it was possible to achieve efficient electroluminescence in the range from green (DEV4) to orange-red light (DEV3) with a maximum luminance of 3 820 cd/m
Language	English
Publishing date	2023-09-25
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202302115
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Article ; Online: The effect of chlorination degree and substitution pattern on the interactions of polychlorinated biphenyls with model bacterial membranes.

Wójcik, Aneta / Bieniasz, Agata / Wydro, Paweł / Broniatowski, Marcin

Biochimica et biophysica acta. Biomembranes

2019 Volume 1861, Issue 6, Page(s) 1057–1068

Abstract: Polychlorinated biphenyls (PCB) are persistent organic pollutants that due to their chemical resistivity and inflammability found multiple applications. In spite of the global ban for PCB production, due to their long half-lives periods, PCB accumulate ... ...

Abstract	Polychlorinated biphenyls (PCB) are persistent organic pollutants that due to their chemical resistivity and inflammability found multiple applications. In spite of the global ban for PCB production, due to their long half-lives periods, PCB accumulate in the soils, so effective bioremediation of the polluted lands is of crucial importance. Some of the 209 PCB congeners exhibit increased toxicity to soil bacteria and their presence impoverish the soil decomposer community and slows down the degradation of environmental pollutants in the soils. The exact mechanism of PCB antimicrobial activity is unknown, but it is strictly related with the membrane activity of PCB. Therefore, to shed light on these interactions we applied Langmuir monolayers formed by selected phospholipids as model bacterial membranes. In our studies we tested 5 PCB congeners differing in the degree of chlorination and the distribution of the chlorine substituents around the biphenyl frame. Special attention was paid to tetra-substituted PCB because of their increased presence in the environment and disubstituted PCB being their degradation products. To characterize the model membranes as Langmuir monolayers, we used surface pressure measurements, Brewster angle microscopy and Grazing Incidence X-ray Diffraction. It turned out that among the tetra-substituted PCB the ortho-substituted non-dioxin like compound was much more membrane destructive than the flat dioxin-like congener. On the contrary, among the di-substituted PCB the flat para-substituted 2,2'-dichlorobiphenyl turned out to exhibit high membrane activity.
MeSH term(s)	Cell Membrane/drug effects ; Gram-Negative Bacteria/drug effects ; Gram-Negative Bacteria/metabolism ; Gram-Negative Bacteria/ultrastructure ; Gram-Positive Bacteria/drug effects ; Gram-Positive Bacteria/metabolism ; Gram-Positive Bacteria/ultrastructure ; Halogenation ; Membrane Lipids/metabolism ; Microscopy/methods ; Phospholipids/metabolism ; Polychlorinated Biphenyls/pharmacology ; X-Ray Diffraction/methods
Chemical Substances	Membrane Lipids ; Phospholipids ; Polychlorinated Biphenyls (DFC2HB4I0K)
Language	English
Publishing date	2019-03-16
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	60-7
ISSN	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650 ; 0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
ISSN (online)	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650
ISSN	0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
DOI	10.1016/j.bbamem.2019.03.009
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Article ; Online: The role of phospholipid composition and ergosterol presence in the adaptation of fungal membranes to harsh environmental conditions-membrane modeling study.

Perczyk, Paulina / Wójcik, Aneta / Wydro, Paweł / Broniatowski, Marcin

Biochimica et biophysica acta. Biomembranes

2019 Volume 1862, Issue 2, Page(s) 183136

Abstract: Soil fungi play an important role in the environment decomposing dead organic matter and degrading persistent organic pollutants (POP). The presence of hydrophobic POP in the soil and membrane-lytic substances excreted by competing microorganism to the ... ...

Abstract	Soil fungi play an important role in the environment decomposing dead organic matter and degrading persistent organic pollutants (POP). The presence of hydrophobic POP in the soil and membrane-lytic substances excreted by competing microorganism to the soil solution is the constant threat to these organisms. To survive in the harsh environment and counteract these hazards the fungal cells have to strictly control the composition of the lipids in their cellular membranes. However, in the case of fungal membranes the correlation between their composition and physical properties is not fully understood. In our studies we applied Langmuir monolayers formed by phospholipids typical to fungal membranes and ergosterol as versatile model membranes. These membranes were characterized by the Langmuir technique, Brewster Angle Microscopy and Grazing Incidence X-ray Diffraction, as well as were exposed to the action of phospholipase A2 treated as a model membrane-lytic protein. We started our studies from the equimolar mixture of phosphatidylethanolamine with phosphatidylcholine and doped this matrix with phosphatidylserine (PS) or phosphatidylinositol (PI). It turned out that the membranes with PS were much more condensed at the mesoscale and periodically organized at the molecular level. Starting from these models we derived two families of model fungal membranes adding to these phospholipid matrices ergosterol. It turned out that the level of ergosterol content is of crucial importance for the model membrane structure and its durability. Changing the ergosterol mole ratio from 0 to 0.5 we defined and described in detail four different 2D crystalline phases.
MeSH term(s)	Cell Membrane/chemistry ; Ergosterol/chemistry ; Fungi/chemistry ; Phosphatidylcholines/chemistry ; Phosphatidylinositols/chemistry ; Phosphatidylserines/chemistry ; Phospholipases A2/metabolism ; Unilamellar Liposomes/chemistry
Chemical Substances	Phosphatidylcholines ; Phosphatidylinositols ; Phosphatidylserines ; Unilamellar Liposomes ; Phospholipases A2 (EC 3.1.1.4) ; Ergosterol (Z30RAY509F)
Language	English
Publishing date	2019-11-18
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	60-7
ISSN	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650 ; 0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
ISSN (online)	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650
ISSN	0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
DOI	10.1016/j.bbamem.2019.183136
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Article ; Online: The composition of phospholipid model bacterial membranes determines their endurance to secretory phospholipase A2 attack - The role of cardiolipin.

Perczyk, Paulina / Wójcik, Aneta / Hachlica, Natalia / Wydro, Paweł / Broniatowski, Marcin

Biochimica et biophysica acta. Biomembranes

2020 Volume 1862, Issue 6, Page(s) 183239

Abstract: Soil bacteria are decomposer organisms crucial for the biodegradation of organic pollutants, mineralization of dead organic matter and the turnover of biogenic elements. In their environment they are constantly exposed to membrane-lytic enzymes emitted ... ...

Abstract	Soil bacteria are decomposer organisms crucial for the biodegradation of organic pollutants, mineralization of dead organic matter and the turnover of biogenic elements. In their environment they are constantly exposed to membrane-lytic enzymes emitted to the soil by other microorganisms competing for the same niche. Therefore, the composition and structure of their membranes is of utmost importance for survival in the harsh environment. Although soil bacteria species can be Gram-negative or Gram-positive and their membranes differ significantly, they are formed by phospholipids belonging mainly to three classes: phosphatidylethanolamines (PE), phosphatidylglycerols (PG) and cardiolipins (CL). The correlation of the membrane phospholipid composition and its susceptibility to secretory membrane-lytic enzymes is widely unknown; thus, to shed light on these phenomena we applied the Langmuir monolayer technique to construct models of soil bacteria membranes differing in the mutual proportion of the main phospholipids. To characterize the systems we studied their elasticity, mesoscopic texture, 2D crystalline structure and discussed the thermodynamics of the interactions between their components. The model membranes were exposed to secretory phospholipase A2. It turned out that in spite of the structural similarities the model membranes differed significantly in their susceptibility to s-PLA2 attack. The membranes devoid of cardiolipin were completely degraded, whereas, these containing cardiolipin were much more resistant to the enzymatic hydrolysis. It also turned out that the sole presence of cardiolipin in the model membrane did not guarantee the membrane durability and that the interplay between cardiolipin and the zwitterionic phosphatidylethanolamine was here of crucial importance.
MeSH term(s)	Bacterial Outer Membrane/chemistry ; Bacterial Outer Membrane/physiology ; Cardiolipins/analysis ; Cardiolipins/physiology ; Membranes, Artificial ; Models, Biological ; Phosphatidylethanolamines/analysis ; Phosphatidylglycerols/analysis ; Phospholipases A2, Secretory/metabolism ; Phospholipids/analysis ; Phospholipids/chemistry ; Soil Microbiology
Chemical Substances	Cardiolipins ; Membranes, Artificial ; Phosphatidylethanolamines ; Phosphatidylglycerols ; Phospholipids ; Phospholipases A2, Secretory (EC 3.1.1.4)
Language	English
Publishing date	2020-02-28
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	60-7
ISSN	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650 ; 0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
ISSN (online)	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650
ISSN	0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
DOI	10.1016/j.bbamem.2020.183239
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Article: Diels-Alder Cycloaddition with CO, CO

Krompiec, Stanisław / Kurpanik-Wójcik, Aneta / Matussek, Marek / Gołek, Bogumiła / Mieszczanin, Angelika / Fijołek, Aleksandra

Materials (Basel, Switzerland)

2021 Volume 15, Issue 1

Abstract: Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials' properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels-Alder ... ...

Abstract	Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials' properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels-Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, 1,3-cyclopentadienones are valuable substrates for [4 + 2] cycloaddition, leading to multisubstituted derivatives of benzene, naphthalene, and other aromatics. Cycloadditions of dienes can be carried out with extrusion of carbon dioxide, carbon oxide, or sulphur dioxide. When pyranones, dioxothiophenes, or cyclopentadienones and DA cycloaddition are aided with acetylenes including masked ones, conjugated or isolated diynes, or polyynes and arynes, aromatic systems are obtained. This review covers the development and the current state of knowledge regarding thermal DA cycloaddition of dienes mentioned above and dienophiles leading to (hetero)aromatics via CO, CO
Language	English
Publishing date	2021-12-27
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	2487261-1
ISSN	1996-1944
ISSN	1996-1944
DOI	10.3390/ma15010172
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Article ; Online: Effects of water soluble perfluorinated pollutants on phospholipids in model soil decomposer membranes.

Wójcik, Aneta / Perczyk, Paulina / Wydro, Paweł / Broniatowski, Marcin

Biochimica et biophysica acta. Biomembranes

2018 Volume 1860, Issue 12, Page(s) 2576–2587

Abstract: Water soluble perfluorinated compounds (PFCs) as perfluorooctanesulfonate (PFOS), perfluorooctanoate (PFOA) and their shorter chain homologues are persistent organic pollutants widely distributed in the environment. PFCs accumulate in soils and sediments ...

Abstract	Water soluble perfluorinated compounds (PFCs) as perfluorooctanesulfonate (PFOS), perfluorooctanoate (PFOA) and their shorter chain homologues are persistent organic pollutants widely distributed in the environment. PFCs accumulate in soils and sediments and because of their toxicity endanger the decomposer organisms. PFCs are toxic to a wide spectrum of soil bacteria and their biocide activity was related with their membrane activity; however, the exact mechanism of PFCs - bacterial membrane interactions is unknown. Therefore, to shed light on these questions we applied phospholipid Langmuir monolayers as simplified models of bacterial membranes and studied their interactions with selected environmentally relevant PFCs. The mechanical properties of the monolayers were characterized by surface pressure-mean molecular area isotherms and the analysis of compression modulus. The effects of PFC on the texture of the model membranes were studied with Brewster angle microscopy, whereas their influence on molecular packing in the 2D crystal lattice was searched by the Grazing Incidence X-ray diffraction technique. The effects of PFCs on the phospholipid polar heargroup conformation were studied by PM-IRRAS spectroscopy, whereas the effectivenes of the incorporation of PFCs into the model membrane was monitored in penetration tests. It turned out that the membranes rich in phosphatidylethanolamine typical to Gram negative bacteria are much PFCs susceptible than the cardiolipin rich membranes imitating Gram positive species. Moreover, the studies indicated that the switch from eight‑carbon atom perfluorinated chains to shorter chain homologues is not necessarily environmentally benign as perfluorobutane sulfonate caused also significant structural changes in the model membranes.
MeSH term(s)	Fluorocarbons/chemistry ; Fluorocarbons/toxicity ; Models, Chemical ; Phospholipids/chemistry ; Soil Pollutants/chemistry ; Soil Pollutants/toxicity ; Solubility ; Water/chemistry
Chemical Substances	Fluorocarbons ; Phospholipids ; Soil Pollutants ; Water (059QF0KO0R)
Language	English
Publishing date	2018-09-21
Publishing country	Netherlands
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	60-7
ISSN	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650 ; 0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
ISSN (online)	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650
ISSN	0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
DOI	10.1016/j.bbamem.2018.09.014
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Article ; Online: Effects of Polychlorinated Pesticides and Their Metabolites on Phospholipid Organization in Model Microbial Membranes.

Wojcik, Aneta / Pawłowski, Marcin / Wydro, Paweł / Broniatowski, Marcin

The journal of physical chemistry. B

2018 Volume 122, Issue 50, Page(s) 12017–12030

Abstract: Polychlorinated pesticides (PPs) were classified as persistent organic pollutants because of their toxicity, limited degradability in the environment, bioaugmentation, and accumulation in animal tissues. PPs accumulate in the environment mainly in the ... ...

Abstract	Polychlorinated pesticides (PPs) were classified as persistent organic pollutants because of their toxicity, limited degradability in the environment, bioaugmentation, and accumulation in animal tissues. PPs accumulate in the environment mainly in the soils and water sediments where they are toxic to the decomposer organisms including soil bacteria and fungi. Therefore, there is an urgent need to search for the microorganisms capable of PP biodegradation which could be applied for soil bioremediation. The exact mechanism of PP microbial toxicity is unknown; however, there is evidence that it can be membrane related. To shed light on the interactions of PPs with microbial membranes, we applied Langmuir monolayers formed by phospholipids as model biomembranes. The model membranes were formed by phospholipids typical to microbial membranes: cardiolipins and phosphatidylglycerols the main components of Gram positive bacteria membranes, phosphatidylcholine typical to fungal membranes, as well as phosphatidylethanolamine found in the inner membranes of Gram negative bacteria. For the studies, the most ecotoxic PPs and their water-soluble metabolites were chosen. The monolayers were studied with the application of mutually complementary techniques: Langmuir technique, grazing incidence X-ray diffraction, and PM-IRRAS spectroscopy. It turned out that the cyclodiene PPs are more membrane active than monocyclic PPs and that the possibility of their incorporation is strictly related to the phospholipid structure. The membranes prepared with cardiolipin turned out to be especially resistant to PP incorporation. Regarding the metabolites, pentachlorophenol turned out to be especially structure breaking, affecting the molecular organization of all of the investigated phospholipids.
MeSH term(s)	Animals ; Gram-Negative Bacteria/chemistry ; Gram-Negative Bacteria/cytology ; Gram-Negative Bacteria/metabolism ; Hydrocarbons, Chlorinated/chemistry ; Hydrocarbons, Chlorinated/metabolism ; Intracellular Membranes/chemistry ; Intracellular Membranes/metabolism ; Models, Biological ; Molecular Structure ; Particle Size ; Pesticides/chemistry ; Pesticides/metabolism ; Phospholipids/chemistry ; Phospholipids/metabolism ; Surface Properties
Chemical Substances	Hydrocarbons, Chlorinated ; Pesticides ; Phospholipids
Language	English
Publishing date	2018-12-11
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	1520-5207
ISSN (online)	1520-5207
DOI	10.1021/acs.jpcb.8b08989
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Article ; Online: Interactions of Long-Chain Perfluorotelomer Alcohol and Perfluorinated Hydrocarbons with Model Decomposer Membranes.

Wójcik, Aneta / Perczyk, Paulina / Wydro, Paweł / Flasiński, Michał / Broniatowski, Marcin

The journal of physical chemistry. B

2018 Volume 122, Issue 29, Page(s) 7340–7352

Abstract: Perfluorinated hydrocarbons and their polar derivatives are produced annually in high quantities and find multiple industrial and technological applications due to their chemical and physical durability, significant hydro- and lipophobicity and excellent ...

Abstract	Perfluorinated hydrocarbons and their polar derivatives are produced annually in high quantities and find multiple industrial and technological applications due to their chemical and physical durability, significant hydro- and lipophobicity and excellent surface activity. Unfortunately, multiple perfluorinated compounds are recognized as persistent organic pollutants as they are completely nonbiodegradable and accumulate in soils and sediments. In our studies, we applied Langmuir monolayers formed by different structural phospholipids as models of soil bacteria and fungi membranes and investigated the effects exerted by long-chain perfluorinated pollutants, perfluorotelomer alcohol and two structurally different perfluorinated hydrocarbons, on the artificial membranes. Various mutually complemental methods such as surface pressure-mean molecular area isotherm registration, Brewster angle microscopy (BAM), and grazing incidence X-ray diffraction (GIXD) were applied. It turned out that the presence of the perfluorinated chemicals profoundly affected the phospholipid monolayers. The miscibility of the phospholipid with the perfluorotelomer alcohol depended strongly on the size and charge of the polar headgroup. Additionally, it was observed by BAM that the presence of the perfluorinated molecules significantly changed the texture of all the investigated phospholipid monolayers. On the basis of the BAM and GIXD results and other studies described in the scientific literature, we postulated that the perfluorinated hydrocarbons form an additional monolayer anchored on top of the phospholipid film. Our studies prove that both polar and nonpolar perfluorinated pollutants can be toxic to decomposer organisms and that their toxicity is strictly correlated with the phospholipid composition of the cellular membrane.
MeSH term(s)	Fluorocarbons/chemistry ; Hydrocarbons, Fluorinated/chemistry ; Lipid Bilayers/chemistry ; Microscopy ; Phospholipids/chemistry ; Thermodynamics ; X-Ray Diffraction
Chemical Substances	Fluorocarbons ; Hydrocarbons, Fluorinated ; Lipid Bilayers ; Phospholipids
Language	English
Publishing date	2018-07-13
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	1520-5207
ISSN (online)	1520-5207
DOI	10.1021/acs.jpcb.8b05194
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Article ; Online: The influence of terpinen-4-ol and eucalyptol - The essential oil components - on fungi and plant sterol monolayers.

Połeć, Karolina / Wójcik, Aneta / Flasiński, Michał / Wydro, Paweł / Broniatowski, Marcin / Hąc-Wydro, Katarzyna

Biochimica et biophysica acta. Biomembranes

2019 Volume 1861, Issue 6, Page(s) 1093–1102

Abstract: Antifungal and herbicidal activity of terpenes, being the components of the essential oils, is directly related to the incorporation of these compounds into cellular membranes. Thus, the differences in the lipid composition of various pathogenic ... ...

Abstract	Antifungal and herbicidal activity of terpenes, being the components of the essential oils, is directly related to the incorporation of these compounds into cellular membranes. Thus, the differences in the lipid composition of various pathogenic membranes may be the factor determining the activity of these molecules. One of the class of lipids, which form the membrane environment are sterols. The aim of this work was to compare the effect of two terpenes: terpinen-4-ol and eucalyptol on the monolayers formed by ergosterol and β - sitosterol, which are the components of fungi and plant membranes, respectively. The modifications in the sterol monolayer properties were investigated in the surface pressure-area measurements and penetration studies as well as in a micrometer scale (Brewster angle microscopy experiments) and in nanoscale (GIXD technique). It was evidenced that although at higher surface pressure the terpene molecules are in part removed from the interface, they are able to substantially modify the condensation, morphology and molecular organization of the sterol film. It was also found that the incorporation of terpenes into sterol films is comparable for both sterols, however, β - sitosterol monolayers properties are affected more strongly than ergosterol films. Finally, the analysis of the results of the studies performed on model membrane systems and the results of antimicrobial studies reported in literature, enabled us to suggest that the activity of terpenes depends on the membrane composition and that the sterol concentration may be important from the point of view of antifungal effect of terpinen-4-ol and eucalyptol.
MeSH term(s)	Eucalyptol/chemistry ; Fungi/chemistry ; Microscopy/methods ; Oils, Volatile/chemistry ; Phytosterols/chemistry ; Sterols/chemistry ; Surface Properties ; Terpenes/chemistry ; X-Ray Diffraction/methods
Chemical Substances	Oils, Volatile ; Phytosterols ; Sterols ; Terpenes ; terpinenol-4 (562-74-3) ; Eucalyptol (RV6J6604TK)
Language	English
Publishing date	2019-03-26
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	60-7
ISSN	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650 ; 0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
ISSN (online)	1879-2642 ; 1879-2596 ; 1879-260X ; 1872-8006 ; 1879-2618 ; 1879-2650
ISSN	0006-3002 ; 0005-2728 ; 0005-2736 ; 0304-4165 ; 0167-4838 ; 1388-1981 ; 0167-4889 ; 0167-4781 ; 0304-419X ; 1570-9639 ; 0925-4439 ; 1874-9399
DOI	10.1016/j.bbamem.2019.03.015
Database	MEDical Literature Analysis and Retrieval System OnLINE

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