Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa
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2019
Authors
Stanković, JovanaGodjevac, Dejan
Tešević, Vele
Dajić-Stevanović, Zora
Ćirić, Ana
Soković, Marina
Novaković, Miroslav
Article (Published version)
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A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-beta-D-glucuronopyranosyl-(1 -> 2)-beta-D-glucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, beta-D-glucopyranosyl-3-O-(2-O-sulfo-beta-D-galactopyranosyl)-(1 -> 2)-alpha-L-arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, beta-D-glucopyranosyl-3-O-(2-O-sulfo-beta-D-galactopyranosyl)-(1 -> 2)-alpha-L-arabinopyranoside)-30-hydroxyolean-12-en-28-oate (3), named atriplexogenin II, and beta-D-glucopyranosyl-3-D-(beta-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside)-30-alolean-12-en-28-oate (4), named atriplexogenin III, were isolated by silica gel column and semipreparative HPLC chromatography from the n-butanol extract of the salt marsh plant Atriplex tatarica. In addition, two known secondary metabolites, patuletin3-O-beta-D-apiofuranosyl-(1 '''-> 2 '')-beta-D-glucopyranoside (5) and patuletin 3-O-5 '''-O-fer...uloyl-beta-D-apiofuranosyl-(1 '''-> 2 '')-beta-D-glucopyranoside (6), were isolated for the first time from A. tatarica. The structures of the isolated compounds were elucidated by 1D and 2D NMR, HRESIMS, IR, and UV data. Antibacterial activity by the microdilution method and antibiofilm activity against P. aeruginosa were assessed. Compound 5 possesses significant antibacterial activity, while the most potent antibiofilm agent is compound 2.
Source:
Journal of Natural Products, 2019, 82, 6, 1487-1495Publisher:
- Amer Chemical Soc, Washington
Funding / projects:
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-172053)
- Characterization and application of fungal metabolites and assessment of new biofungicides potential (RS-173032)
- Morphological, chemical, pharmacological and agronomic characterization of the Pannonian Thyme (Thymus pannonicus All., Lamiaceae), with the purpose of sustainable production in intensive cropping system (RS-31089)
DOI: 10.1021/acs.jnatprod.8b00970
ISSN: 0163-3864
PubMed: 31181926
WoS: 000473827300011
Scopus: 2-s2.0-85067065776
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Poljoprivredni fakultetTY - JOUR AU - Stanković, Jovana AU - Godjevac, Dejan AU - Tešević, Vele AU - Dajić-Stevanović, Zora AU - Ćirić, Ana AU - Soković, Marina AU - Novaković, Miroslav PY - 2019 UR - http://aspace.agrif.bg.ac.rs/handle/123456789/5049 AB - A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-beta-D-glucuronopyranosyl-(1 -> 2)-beta-D-glucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, beta-D-glucopyranosyl-3-O-(2-O-sulfo-beta-D-galactopyranosyl)-(1 -> 2)-alpha-L-arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, beta-D-glucopyranosyl-3-O-(2-O-sulfo-beta-D-galactopyranosyl)-(1 -> 2)-alpha-L-arabinopyranoside)-30-hydroxyolean-12-en-28-oate (3), named atriplexogenin II, and beta-D-glucopyranosyl-3-D-(beta-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside)-30-alolean-12-en-28-oate (4), named atriplexogenin III, were isolated by silica gel column and semipreparative HPLC chromatography from the n-butanol extract of the salt marsh plant Atriplex tatarica. In addition, two known secondary metabolites, patuletin3-O-beta-D-apiofuranosyl-(1 '''-> 2 '')-beta-D-glucopyranoside (5) and patuletin 3-O-5 '''-O-feruloyl-beta-D-apiofuranosyl-(1 '''-> 2 '')-beta-D-glucopyranoside (6), were isolated for the first time from A. tatarica. The structures of the isolated compounds were elucidated by 1D and 2D NMR, HRESIMS, IR, and UV data. Antibacterial activity by the microdilution method and antibiofilm activity against P. aeruginosa were assessed. Compound 5 possesses significant antibacterial activity, while the most potent antibiofilm agent is compound 2. PB - Amer Chemical Soc, Washington T2 - Journal of Natural Products T1 - Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa EP - 1495 IS - 6 SP - 1487 VL - 82 DO - 10.1021/acs.jnatprod.8b00970 ER -
@article{ author = "Stanković, Jovana and Godjevac, Dejan and Tešević, Vele and Dajić-Stevanović, Zora and Ćirić, Ana and Soković, Marina and Novaković, Miroslav", year = "2019", abstract = "A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-beta-D-glucuronopyranosyl-(1 -> 2)-beta-D-glucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, beta-D-glucopyranosyl-3-O-(2-O-sulfo-beta-D-galactopyranosyl)-(1 -> 2)-alpha-L-arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, beta-D-glucopyranosyl-3-O-(2-O-sulfo-beta-D-galactopyranosyl)-(1 -> 2)-alpha-L-arabinopyranoside)-30-hydroxyolean-12-en-28-oate (3), named atriplexogenin II, and beta-D-glucopyranosyl-3-D-(beta-D-glucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside)-30-alolean-12-en-28-oate (4), named atriplexogenin III, were isolated by silica gel column and semipreparative HPLC chromatography from the n-butanol extract of the salt marsh plant Atriplex tatarica. In addition, two known secondary metabolites, patuletin3-O-beta-D-apiofuranosyl-(1 '''-> 2 '')-beta-D-glucopyranoside (5) and patuletin 3-O-5 '''-O-feruloyl-beta-D-apiofuranosyl-(1 '''-> 2 '')-beta-D-glucopyranoside (6), were isolated for the first time from A. tatarica. The structures of the isolated compounds were elucidated by 1D and 2D NMR, HRESIMS, IR, and UV data. Antibacterial activity by the microdilution method and antibiofilm activity against P. aeruginosa were assessed. Compound 5 possesses significant antibacterial activity, while the most potent antibiofilm agent is compound 2.", publisher = "Amer Chemical Soc, Washington", journal = "Journal of Natural Products", title = "Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa", pages = "1495-1487", number = "6", volume = "82", doi = "10.1021/acs.jnatprod.8b00970" }
Stanković, J., Godjevac, D., Tešević, V., Dajić-Stevanović, Z., Ćirić, A., Soković, M.,& Novaković, M.. (2019). Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa. in Journal of Natural Products Amer Chemical Soc, Washington., 82(6), 1487-1495. https://doi.org/10.1021/acs.jnatprod.8b00970
Stanković J, Godjevac D, Tešević V, Dajić-Stevanović Z, Ćirić A, Soković M, Novaković M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa. in Journal of Natural Products. 2019;82(6):1487-1495. doi:10.1021/acs.jnatprod.8b00970 .
Stanković, Jovana, Godjevac, Dejan, Tešević, Vele, Dajić-Stevanović, Zora, Ćirić, Ana, Soković, Marina, Novaković, Miroslav, "Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa" in Journal of Natural Products, 82, no. 6 (2019):1487-1495, https://doi.org/10.1021/acs.jnatprod.8b00970 . .