Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. Roots
In this study, three new undescribed triterpene saponins named primulasaponin III–V (<b>19</b>–<b>21</b>) were isolated from the roots of <i>Primula veris</i> L. of Bulgarian origin together with the known primulasaponin I. Their structures were elucidated via 1D...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/8/1702 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850180004422352896 |
|---|---|
| author | Antoaneta Trendafilova Desislava Raykova Viktoria Ivanova Miroslav Novakovic Paraskev Nedialkov Tsvetelina Paunova-Krasteva Ralitsa Veleva Tanya Topouzova-Hristova |
| author_facet | Antoaneta Trendafilova Desislava Raykova Viktoria Ivanova Miroslav Novakovic Paraskev Nedialkov Tsvetelina Paunova-Krasteva Ralitsa Veleva Tanya Topouzova-Hristova |
| author_sort | Antoaneta Trendafilova |
| collection | DOAJ |
| description | In this study, three new undescribed triterpene saponins named primulasaponin III–V (<b>19</b>–<b>21</b>) were isolated from the roots of <i>Primula veris</i> L. of Bulgarian origin together with the known primulasaponin I. Their structures were elucidated via 1D and 2D NMR spectroscopy and HR-ESI-MS. In addition, 17 known phenolic compounds (six flavones, three acetophenones, four bisbibenzyls, and four phenolic glycosides) were identified in the chloroform and methanol extracts. Among them, flavone, 2′-methoxyflavone, 3′-methoxyflavone, 3′-hydroxy-4′,5′-dimethoxyflavone, 2′,5′-dimethoxyflavone, 3′-methoxy-4′,5′-methylendioxyflavone, paeonol, 2-primeverosyl-5-methoxy-acetophenone, and paeonolide were detected for the first time in the roots of <i>P. veris.</i> The minimum inhibitory and minimum bactericidal concentrations of the chloroform and methanol extracts of <i>P. veris</i> roots and the saponin-enriched fraction were determined, with MIC values ranging between 0.5 and 1 mg/mL. Additionally, the tested samples were evaluated for their ability to inhibit biofilm formation in the presence of sub-MICs. All tested samples showed better biofilm inhibition of Gram-negative strains compared to Gram-positive strains. The strongest effect was observed for the chloroform extract against the biofilm formation of <i>Pseudomonas aeruginosa</i>, while the saponin-enriched fraction showed the highest percentage of biofilm inhibition of <i>Escherichia coli</i>, <i>Staphylococcus aureus</i>, and <i>Staphylococcus mutans</i>. At the same time, chloroform extract showed lower cytotoxicity against human keranocyte cell line HaCaT, as compared with methanol extract and the saponin-enriched fraction. |
| format | Article |
| id | doaj-art-e66eae91df7f4d1d840ce0917241d10f |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-e66eae91df7f4d1d840ce0917241d10f2025-08-20T02:18:20ZengMDPI AGMolecules1420-30492025-04-01308170210.3390/molecules30081702Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. RootsAntoaneta Trendafilova0Desislava Raykova1Viktoria Ivanova2Miroslav Novakovic3Paraskev Nedialkov4Tsvetelina Paunova-Krasteva5Ralitsa Veleva6Tanya Topouzova-Hristova7Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 1113 Sofia, BulgariaInstitute of Chemistry, Technology and Metallurgy, National Institute of the Republic of Serbia, University of Belgrade, 11000 Belgrade, SerbiaPharmacognosy Department, Faculty of Pharmacy, Medical University of Sofia, 1000 Sofia, BulgariaStephan Angeloff Institute of Microbiology, Bulgarian Academy of Sciences, 1113 Sofia, BulgariaDepartment of Cellular and Developmental Biology, Faculty of Biology, Sofia University St Kliment Ohridski, 1164 Sofia, BulgariaDepartment of Cellular and Developmental Biology, Faculty of Biology, Sofia University St Kliment Ohridski, 1164 Sofia, BulgariaIn this study, three new undescribed triterpene saponins named primulasaponin III–V (<b>19</b>–<b>21</b>) were isolated from the roots of <i>Primula veris</i> L. of Bulgarian origin together with the known primulasaponin I. Their structures were elucidated via 1D and 2D NMR spectroscopy and HR-ESI-MS. In addition, 17 known phenolic compounds (six flavones, three acetophenones, four bisbibenzyls, and four phenolic glycosides) were identified in the chloroform and methanol extracts. Among them, flavone, 2′-methoxyflavone, 3′-methoxyflavone, 3′-hydroxy-4′,5′-dimethoxyflavone, 2′,5′-dimethoxyflavone, 3′-methoxy-4′,5′-methylendioxyflavone, paeonol, 2-primeverosyl-5-methoxy-acetophenone, and paeonolide were detected for the first time in the roots of <i>P. veris.</i> The minimum inhibitory and minimum bactericidal concentrations of the chloroform and methanol extracts of <i>P. veris</i> roots and the saponin-enriched fraction were determined, with MIC values ranging between 0.5 and 1 mg/mL. Additionally, the tested samples were evaluated for their ability to inhibit biofilm formation in the presence of sub-MICs. All tested samples showed better biofilm inhibition of Gram-negative strains compared to Gram-positive strains. The strongest effect was observed for the chloroform extract against the biofilm formation of <i>Pseudomonas aeruginosa</i>, while the saponin-enriched fraction showed the highest percentage of biofilm inhibition of <i>Escherichia coli</i>, <i>Staphylococcus aureus</i>, and <i>Staphylococcus mutans</i>. At the same time, chloroform extract showed lower cytotoxicity against human keranocyte cell line HaCaT, as compared with methanol extract and the saponin-enriched fraction.https://www.mdpi.com/1420-3049/30/8/1702<i>Primula veris</i> L.phenolic compoundsprimulasaponin Inew primulasaponinsNMRantibiofilm activity |
| spellingShingle | Antoaneta Trendafilova Desislava Raykova Viktoria Ivanova Miroslav Novakovic Paraskev Nedialkov Tsvetelina Paunova-Krasteva Ralitsa Veleva Tanya Topouzova-Hristova Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. Roots Molecules <i>Primula veris</i> L. phenolic compounds primulasaponin I new primulasaponins NMR antibiofilm activity |
| title | Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. Roots |
| title_full | Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. Roots |
| title_fullStr | Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. Roots |
| title_full_unstemmed | Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. Roots |
| title_short | Phytochemical Characterization and Anti-Biofilm Activity of <i>Primula veris</i> L. Roots |
| title_sort | phytochemical characterization and anti biofilm activity of i primula veris i l roots |
| topic | <i>Primula veris</i> L. phenolic compounds primulasaponin I new primulasaponins NMR antibiofilm activity |
| url | https://www.mdpi.com/1420-3049/30/8/1702 |
| work_keys_str_mv | AT antoanetatrendafilova phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots AT desislavaraykova phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots AT viktoriaivanova phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots AT miroslavnovakovic phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots AT paraskevnedialkov phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots AT tsvetelinapaunovakrasteva phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots AT ralitsaveleva phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots AT tanyatopouzovahristova phytochemicalcharacterizationandantibiofilmactivityofiprimulaverisilroots |