Isolation and Antimicrobial Activity of Coumarin Derivatives from Fruits of Peucedanum luxurians Tamamsch
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preliminary HPLC Analysis and Screening of Activity of Extracts
2.2. HPCCC Separation
2.3. Quantitative HPLC-DAD Analysis
2.4. Antimicrobial Activity
3. Materials and Methods
3.1. Chemicals
3.2. Plant Material
3.3. Accelerated Solvent Extraction
3.4. HPCCC Separation
3.4.1. HPCCC Apparatus
3.4.2. Selection of Two-Phase Solvent System
3.4.3. Separation Procedure
3.5. Semi-Preparative HPLC Separation
3.6. HPLC-DAD Analysis
3.7. HPLC-DAD-ESI-Q-TOF-MS Analysis
3.8. NMR Analysis
3.9. Antimicrobial Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 6′,7′-dihydroxybergamottin, officinalin, stenocarpin isobutyrate, officinalin isobutyrate, 8-methoxypeucedanin, and peucedaninare available from the authors. |
Solvent System | Coumarins | |||||
---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | |
HEMWat (5:6:5:6) | 0.83 | 3.01 | 5.14 | 5.16 | 9.49 | 11.57 |
HEMWat (1:1:1:1) | 0.47 | 1.59 | 3.09 | 3.25 | 5.31 | 6.34 |
PEMWat (1:1:1:1) | 0.50 | 1.95 | 2.47 | 2.51 | 4.38 | 4.90 |
HAtWat (3.9:5:1.9) | 0.16 | 1.22 | 1.15 | 1.06 | 0.55 | 0.33 |
HEMWat (6:5:6:5) | 0.19 | 0.89 | 1.57 | 1.65 | 2.85 | 3.61 |
α2/1 = 4.68 | α3/2 = 1.76 | α4/3 = 1.05 | α5/4 = 1.73 | α6/5 = 1.27 |
Coumarins | Plant Material | Solvent | Yield (mg/100 g d.w.) | RSD% |
---|---|---|---|---|
1 | Aerial parts | PE | 13.72 ± 0.41 | 2.99 |
DCM | 24.71 ± 0.66 | 2.67 | ||
MeOH | 30.61 ± 1.83 | 5.97 | ||
Fruits | PE | 83.17 ± 5.04 | 6.05 | |
DCM | 442.23 ± 2.45 | 0.55 | ||
MeOH | 465.74 ± 1.66 | 0.36 | ||
2 | Aerial parts | PE | 29.60 ± 0.84 | 2.84 |
DCM | 51.70 ± 2.71 | 5.24 | ||
MeOH | 53.51 ± 0.39 | 0.73 | ||
Fruits | PE | 229.12 ± 0.62 | 0.27 | |
DCM | 1336.26 ± 0.80 | 0.06 | ||
MeOH | 1309.43 ± 1.31 | 0.10 | ||
3 | Aerial parts | PE | 23.61 ± 0.02 | 0.09 |
DCM | 33.49 ± 0.19 | 0.58 | ||
MeOH | 47.84 ± 0.95 | 1.99 | ||
Fruits | PE | 56.86 ± 0.03 | 0.05 | |
DCM | 101.72 ± 0.10 | 0.10 | ||
MeOH | 93.88 ± 0.59 | 0.63 | ||
4 | Aerial parts | PE | 8.39 ± 0.12 | 0.13 |
DCM | 8.56 ± 0.16 | 0.12 | ||
MeOH | 8.47 ± 0.41 | 1.06 | ||
Fruits | PE | 89.93 ± 0.12 | 0.13 | |
DCM | 191.78 ± 0.02 | 0.01 | ||
MeOH | 170.06 ± 0.09 | 0.05 | ||
5 | Aerial parts | PE | 62.55 ± 0.03 | 0.05 |
DCM | 79.68 ± 0.29 | 0.37 | ||
MeOH | 66.21 ± 0.07 | 0.11 | ||
Fruits | PE | 341.91 ± 0.17 | 0.05 | |
DCM | 1652.15 ± 0.87 | 0.05 | ||
MeOH | 1622.91 ± 0.56 | 0.03 | ||
6 | Aerial parts | PE | 28.94 ± 0.11 | 0.38 |
DCM | 22.60 ± 0.11 | 0.49 | ||
MeOH | 21.49 ± 0.25 | 1.16 | ||
Fruits | PE | 3689.91 ± 1.07 | 0.03 | |
DCM | 4563.94 ± 3.35 | 0.07 | ||
MeOH | 4538.09 ± 1.13 | 0.02 |
Tested Extract/Compound | S. aureus | S. epidermidis | P. aeruginosa | E. cloacae | K. pneumoniae | E. coli |
---|---|---|---|---|---|---|
P. luxurians aerial parts DCM | 15/1.90 | 16/1.88 | 13/2.40 | 12/3.50 | 12/3.10 | 12/3.35 |
P. luxurians aerial parts MeOH | 17/0.90 | 17/0.92 | 13/2.80 | 12/3.50 | 12/2.75 | 12/2.50 |
P. luxurians fruits DCM | 17/0.84 | 17/0.90 | 14/3.00 | 13/3.45 | 13/2.77 | 13/2.60 |
P. luxurians fruits MeOH | 18/0.95 | 18/0.85 | 14/2.84 | 14/2.75 | 14/2.50 | 14/2.25 |
(1) 6′,7′-Dihydroxybergamottin | 17/1.20 | 17/1.35 | 17/1.37 | 16/1.75 | 16/2.10 | 17/1.45 |
(2) Officinalin | 13/4.50 | 12/5.50 | 12/5.00 | 12/5.75 | 13/4.80 | 13/4.90 |
(3) Stenocarpin isobutyrate | 12/5.25 | 14/4.00 | 13/5.00 | 13/4.80 | 14/3.90 | 14/4.50 |
(4) Officinalin isobutyrate | 14/3.50 | 15/2.70 | 14/3.50 | 15/2.75 | 15/2.25 | 13/4.80 |
(5) 8-metoxypeucedanin | 12/5.25 | 14/4.00 | 13/5.00 | 13/4.80 | 14/3.90 | 14/4.50 |
(6) Peucedanin | 16/1.50 | 16/1.75 | 17/1.40 | 16/2.10 | 16/2.50 | 16/2.75 |
Netilmicin | 21/0.004 | 25/0.004 | 20/0.088 | 23/0.008 | 22/0.008 | 24/0.010 |
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Share and Cite
Widelski, J.; Luca, S.V.; Skiba, A.; Chinou, I.; Marcourt, L.; Wolfender, J.-L.; Skalicka-Wozniak, K. Isolation and Antimicrobial Activity of Coumarin Derivatives from Fruits of Peucedanum luxurians Tamamsch. Molecules 2018, 23, 1222. https://doi.org/10.3390/molecules23051222
Widelski J, Luca SV, Skiba A, Chinou I, Marcourt L, Wolfender J-L, Skalicka-Wozniak K. Isolation and Antimicrobial Activity of Coumarin Derivatives from Fruits of Peucedanum luxurians Tamamsch. Molecules. 2018; 23(5):1222. https://doi.org/10.3390/molecules23051222
Chicago/Turabian StyleWidelski, Jarosław, Simon Vlad Luca, Adrianna Skiba, Ioanna Chinou, Laurence Marcourt, Jean-Luc Wolfender, and Krystyna Skalicka-Wozniak. 2018. "Isolation and Antimicrobial Activity of Coumarin Derivatives from Fruits of Peucedanum luxurians Tamamsch" Molecules 23, no. 5: 1222. https://doi.org/10.3390/molecules23051222