Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites
Аутори
Bukvicki, DankaNovaković, Miroslav
Ilić - Tomić, Tatjana
Nikodinović-Runić, Jasmina
Todorović, Nina
Veljić, Milan
Asakawa, Yoshinori
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound-perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 µM and 450 µM. The me...tabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.
Кључне речи:
1D and 2D NMR / Aspergillus niger / Biotransformation / Cytotoxic activity / Liverworts / Perrottetin FИзвор:
Records of Natural Products, 2021, 15, 4, 281-292Издавач:
- Türkiye : ACG Publications
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200178 (Универзитет у Београду, Биолошки факултет) (RS-MESTD-inst-2020-200178)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200042 (Универзитет у Београду, Институт за молекуларну генетику и генетичко инжењерство) (RS-MESTD-inst-2020-200042)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- The Matsumae International Foundation
DOI: 10.25135/rnp.215.20.09.1812
ISSN: 1307-6167
WoS: 000641301200006
Scopus: 2-s2.0-85105008970
Институција/група
IHTMTY - JOUR AU - Bukvicki, Danka AU - Novaković, Miroslav AU - Ilić - Tomić, Tatjana AU - Nikodinović-Runić, Jasmina AU - Todorović, Nina AU - Veljić, Milan AU - Asakawa, Yoshinori PY - 2021 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4630 AB - Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound-perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 µM and 450 µM. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures. PB - Türkiye : ACG Publications T2 - Records of Natural Products T1 - Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites VL - 15 IS - 4 SP - 281 EP - 292 DO - 10.25135/rnp.215.20.09.1812 ER -
@article{ author = "Bukvicki, Danka and Novaković, Miroslav and Ilić - Tomić, Tatjana and Nikodinović-Runić, Jasmina and Todorović, Nina and Veljić, Milan and Asakawa, Yoshinori", year = "2021", abstract = "Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound-perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 µM and 450 µM. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.", publisher = "Türkiye : ACG Publications", journal = "Records of Natural Products", title = "Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites", volume = "15", number = "4", pages = "281-292", doi = "10.25135/rnp.215.20.09.1812" }
Bukvicki, D., Novaković, M., Ilić - Tomić, T., Nikodinović-Runić, J., Todorović, N., Veljić, M.,& Asakawa, Y.. (2021). Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites. in Records of Natural Products Türkiye : ACG Publications., 15(4), 281-292. https://doi.org/10.25135/rnp.215.20.09.1812
Bukvicki D, Novaković M, Ilić - Tomić T, Nikodinović-Runić J, Todorović N, Veljić M, Asakawa Y. Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites. in Records of Natural Products. 2021;15(4):281-292. doi:10.25135/rnp.215.20.09.1812 .
Bukvicki, Danka, Novaković, Miroslav, Ilić - Tomić, Tatjana, Nikodinović-Runić, Jasmina, Todorović, Nina, Veljić, Milan, Asakawa, Yoshinori, "Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites" in Records of Natural Products, 15, no. 4 (2021):281-292, https://doi.org/10.25135/rnp.215.20.09.1812 . .