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Synthesis, antimicrobial and mutagenic activity of a new class of D-xylopyranosides

2023
journal article
article
10.3390/antibiotics12050888
Journal
Antibiotics
70
Author
Sikora Karol

Szweda Piotr

Słoczyńska Karolina

Samaszko-Fiertek Justyna

Madaj Janusz
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Volume
12
Number
5
Article ID
888
ISSN
2079-6382
eISSN
2079-6382
Keywords in English

d-xylosides

quaternary ammonium salts

NMR

antimicrobial activity

mutagenicity

URL
https://www.mdpi.com/2079-6382/12/5/888
Access date
2023-06-14
Language
English
Journal language
English
Abstract in English

Eight N-[2-(2′,3′,4′-tri-O-acetyl-α/β-d-xylopyranosyloxy)ethyl]ammonium bromides, a new class of d-xylopyranosides containing a quaternary ammonium aglycone, were obtained. Their complete structure was confirmed using NMR spectroscopy (, , COSY and HSQC) and high-resolution mass spectrometry (HRMS). An antimicrobial activity against fungi (Candida albicans, Candida glabrata) and bacteria (Staphylococcus aureus, Escherichia coli) and a mutagenic Ames test with Salmonella typhimurium TA 98 strain were performed for the obtained compounds. The greatest activity against the tested microorganisms was shown by glycosides with the longest (octyl) hydrocarbon chain in ammonium salt. None of the tested compounds exhibited mutagenic activity in the Ames test.

Affiliation
Wydział Farmaceutyczny : Zakład Biochemii Farmaceutycznej
Scopus© citations
2
dc.abstract.enEight N-[2-(2′,3′,4′-tri-O-acetyl-α/β-d-xylopyranosyloxy)ethyl]ammonium bromides, a new class of d-xylopyranosides containing a quaternary ammonium aglycone, were obtained. Their complete structure was confirmed using NMR spectroscopy ($_{}^{1}\textrm{H}$, $_{}^{13}\textrm{C}$, COSY and HSQC) and high-resolution mass spectrometry (HRMS). An antimicrobial activity against fungi (Candida albicans, Candida glabrata) and bacteria (Staphylococcus aureus, Escherichia coli) and a mutagenic Ames test with Salmonella typhimurium TA 98 strain were performed for the obtained compounds. The greatest activity against the tested microorganisms was shown by glycosides with the longest (octyl) hydrocarbon chain in ammonium salt. None of the tested compounds exhibited mutagenic activity in the Ames test.
dc.affiliationWydział Farmaceutyczny : Zakład Biochemii Farmaceutycznejpl
dc.cm.date2023-06-14T22:18:43Z
dc.cm.id112389pl
dc.cm.idOmegaUJCM1cb5c52100384bee9be5ebb83a17e530pl
dc.contributor.authorSikora, Karolpl
dc.contributor.authorSzweda, Piotrpl
dc.contributor.authorSłoczyńska, Karolina - 200093 pl
dc.contributor.authorSamaszko-Fiertek, Justynapl
dc.contributor.authorMadaj, Januszpl
dc.contributor.authorLiberek, Beatapl
dc.contributor.authorPękala, Elżbieta - 133125 pl
dc.contributor.authorDmochowska, Barbarapl
dc.date.accession2023-06-14pl
dc.date.accessioned2023-06-14T22:18:43Z
dc.date.available2023-06-14T22:18:43Z
dc.date.issued2023pl
dc.date.openaccess0
dc.description.accesstimew momencie opublikowania
dc.description.number5pl
dc.description.versionostateczna wersja wydawcy
dc.description.volume12pl
dc.identifier.articleid888pl
dc.identifier.doi10.3390/antibiotics12050888pl
dc.identifier.eissn2079-6382pl
dc.identifier.issn2079-6382pl
dc.identifier.urihttps://ruj.uj.edu.pl/xmlui/handle/item/312260
dc.identifier.weblinkhttps://www.mdpi.com/2079-6382/12/5/888pl
dc.languageengpl
dc.language.containerengpl
dc.pbn.affiliationDziedzina nauk medycznych i nauk o zdrowiu : nauki farmaceutyczne
dc.rightsUdzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa
dc.rights.licenceCC-BY
dc.rights.simpleviewWolny dostęp
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/legalcode.pl
dc.share.typeOtwarte czasopismo
dc.subject.end-xylosides
dc.subject.enquaternary ammonium salts
dc.subject.enNMR
dc.subject.enantimicrobial activity
dc.subject.enmutagenicity
dc.subtypeArticlepl
dc.titleSynthesis, antimicrobial and mutagenic activity of a new class of D-xylopyranosidespl
dc.title.journalAntibioticspl
dc.typeJournalArticlepl
dspace.entity.typePublication
dc.abstract.en
Eight N-[2-(2′,3′,4′-tri-O-acetyl-α/β-d-xylopyranosyloxy)ethyl]ammonium bromides, a new class of d-xylopyranosides containing a quaternary ammonium aglycone, were obtained. Their complete structure was confirmed using NMR spectroscopy ($_{}^{1}\textrm{H}$, $_{}^{13}\textrm{C}$, COSY and HSQC) and high-resolution mass spectrometry (HRMS). An antimicrobial activity against fungi (Candida albicans, Candida glabrata) and bacteria (Staphylococcus aureus, Escherichia coli) and a mutagenic Ames test with Salmonella typhimurium TA 98 strain were performed for the obtained compounds. The greatest activity against the tested microorganisms was shown by glycosides with the longest (octyl) hydrocarbon chain in ammonium salt. None of the tested compounds exhibited mutagenic activity in the Ames test.
dc.affiliationpl
Wydział Farmaceutyczny : Zakład Biochemii Farmaceutycznej
dc.cm.date
2023-06-14T22:18:43Z
dc.cm.idpl
112389
dc.cm.idOmegapl
UJCM1cb5c52100384bee9be5ebb83a17e530
dc.contributor.authorpl
Sikora, Karol
dc.contributor.authorpl
Szweda, Piotr
dc.contributor.authorpl
Słoczyńska, Karolina - 200093
dc.contributor.authorpl
Samaszko-Fiertek, Justyna
dc.contributor.authorpl
Madaj, Janusz
dc.contributor.authorpl
Liberek, Beata
dc.contributor.authorpl
Pękala, Elżbieta - 133125
dc.contributor.authorpl
Dmochowska, Barbara
dc.date.accessionpl
2023-06-14
dc.date.accessioned
2023-06-14T22:18:43Z
dc.date.available
2023-06-14T22:18:43Z
dc.date.issuedpl
2023
dc.date.openaccess
0
dc.description.accesstime
w momencie opublikowania
dc.description.numberpl
5
dc.description.version
ostateczna wersja wydawcy
dc.description.volumepl
12
dc.identifier.articleidpl
888
dc.identifier.doipl
10.3390/antibiotics12050888
dc.identifier.eissnpl
2079-6382
dc.identifier.issnpl
2079-6382
dc.identifier.uri
https://ruj.uj.edu.pl/xmlui/handle/item/312260
dc.identifier.weblinkpl
https://www.mdpi.com/2079-6382/12/5/888
dc.languagepl
eng
dc.language.containerpl
eng
dc.pbn.affiliation
Dziedzina nauk medycznych i nauk o zdrowiu : nauki farmaceutyczne
dc.rights
Udzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa
dc.rights.licence
CC-BY
dc.rights.simpleview
Wolny dostęp
dc.rights.uri
http://creativecommons.org/licenses/by/4.0/legalcode.pl
dc.share.type
Otwarte czasopismo
dc.subject.en
d-xylosides
dc.subject.en
quaternary ammonium salts
dc.subject.en
NMR
dc.subject.en
antimicrobial activity
dc.subject.en
mutagenicity
dc.subtypepl
Article
dc.titlepl
Synthesis, antimicrobial and mutagenic activity of a new class of D-xylopyranosides
dc.title.journalpl
Antibiotics
dc.typepl
JournalArticle
dspace.entity.type
Publication
Affiliations
Wydział Farmaceutyczny
Słoczyńska, Karolina
Pękala, Elżbieta
No affiliation
Sikora, Karol
Szweda, Piotr
Samaszko-Fiertek, Justyna
Madaj, Janusz
Liberek, Beata
Dmochowska, Barbara

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Except as otherwise noted, this item is licensed under : Udzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa

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