Characterization and Biological Evaluation of Propolis from Poland
Abstract
:1. Introduction
2. Results and Discussion
2.1. Propolis Composition
2.2. Antimicrobial Activity
2.3. Antiproliferative Activity
2.4. The Effect of Propolis Extracts in Lung Cancer Cell Proliferation and Toxicity
2.5. The Effect of Propolis Extracts in Colon Cancer Cell Proliferation and Toxicity
2.6. The Effect of Propolis Extracts in Breast Cancer Cell Proliferation and Toxicity
2.7. The Effect of Propolis Extracts in Glioblastoma Cell Proliferation and Toxicity
2.8. The Effect of Propolis Extracts in Fibroblast Cell Proliferation and Toxicity
3. Materials and Methods
3.1. Samples
3.2. Extraction and Sample Derivatization
3.3. GC–MS Analysis
3.4. Antimicrobial Bioassay
3.5. Antiproliferative Activity
3.6. Statistical Analysis
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Sample of studied propolis and previously isolated compounds, like pinocembrin, pinobanksin, chrysin, galangin, kaempferol (by KG and IC), which were used for co-chromatograph are available from the authors. |
Chemical Category | Compounds | % Total Ion Current a |
---|---|---|
Aromatic Acids | Benzoic acid | 3.1 |
Dihydrocinnamic acid | 0.1 | |
Cinnamic acid | 0.1 | |
p-Hydroxybenzoic acid | 0.1 | |
Vanillic acid | 0.1 | |
p-Coumaric acid (Z) | 0.3 | |
p-Methoxycinnamic acid | 0.1 | |
Ferulic acid (Z) | 0.1 | |
p-Coumaric acid (E) | 5.0 | |
Dimethoxycinnamic acid | 0.7 | |
Isoferulic acid | 0.4 | |
Ferulic acid (E) | 3.4 | |
Caffeic acid | 0.1 | |
Other Aromatics | Benzyl alcohol | 0.3 |
Phenylethyl alcohol | 0.1 | |
p-Hydroxybenzaldehyde | 0.1 | |
Hydroquinone | 0.1 | |
Vanilin | 1.0 | |
Fatty Acids | Palmitic acid | 0.4 |
Linoleic acid | 0.7 | |
Oleic acid | 0.3 | |
Esters | Benzyl benzoate | 0.2 |
Propyl p-coumarate | 0.1 | |
Pentyl p-coumarate | 0.2 | |
Butyl p-coumarate | 0.8 | |
Butenyl p-coumarate | 0.4 | |
Benzyl cinnamate | 0.2 | |
Pentyl p-coumarate | 2.6 | |
Pentenyl p-coumarate | 3.4 | |
Isobutyl caffeate | 0.1 | |
Pentenyl ferulate | 0.1 | |
Benzyl p-coumarate (Z) | 0.3 | |
2-Methylbutyl caffeate | 0.1 | |
3-Methyl-3-butenyl caffeate | 0.5 | |
3-Methyl-2-butenyl ferulate | 0.2 | |
2-Methyl-2-butenyl caffeate | 0.3 | |
3-Methyl-2-butenyl caffeate | 0.5 | |
Phenylethyl p-coumarate | 0.1 | |
Benzyl ferulate | 0.1 | |
Benzyl p-coumarate (E) | 6.7 | |
Coniferyl benzoate | 0.6 | |
Benzyl ferulate | 1.9 | |
Benzyl caffeate | 1.5 | |
Phenylethyl caffeate | 0.8 | |
Cinnamyl p-coumarate | 4.0 | |
Cinnamyl ferulate | 0.2 | |
Cinnamyl caffeate | 0.7 | |
Glycerol ester of phenolic acids | 0.6 | |
Coumaryl coumarate | 0.2 | |
Flavonoids and Chalcones | 2′,6′-Dihydroxy-4′-methoxydihydrochalcone | 1.3 |
Trihydroxymonomethoxy chalcone (m/z: 502) | 0.2 | |
Pinostrobin chalcone | 1.2 | |
Pinocembrin chalcone | 2.6 | |
Pinocembrin * | 4.8 | |
Pinobanksin chalcone | 0.3 | |
Sakuranetin | 0.3 | |
Pinobanksin * | 5.7 | |
3-Acetylpinobanksin chalcone | 0.2 | |
Trihydroxyflavanone (m/z: 488) | 0.2 | |
2′,6′-Dihydroxy-4,4′-dimethoxydihydrochalcone | 0.3 | |
3-Acetylalpinon | 0.3 | |
Dihydroxymethoxyflavanone (m/z: 430) | 0.5 | |
3-Acetylpinobanksin | 3.3 | |
2′,6′,4-Trihydroxy-4′-methoxydihydrochalcone | 0.5 | |
Chrysin * | 3.0 | |
Galangin * | 4.0 | |
Dihydroxydimethoxychalcone (m/z: 444) | 0.7 | |
Dimethoxyhydroxyflavanone (m/z: 372) | 0.5 | |
Isosakuranetin chalcone | 1.9 | |
Isosakuranetin | 2.0 | |
Alpinon chalcone | 2.0 | |
Alpinon | 1.9 | |
Naringenin | 0.2 | |
Kaempferol-dimethyl ether | 1.3 | |
Kaempferol-methyl-ether | 2.4 | |
Dihydroxymethoxyflavone (m/z: 428) | 0.6 | |
Kaempferol * | 0.3 | |
Quercetin-methyl-ether | 0.7 | |
Others | Ethylamine | 0.4 |
Glycerol | 0.1 |
Tested Compounds | S. aureus | S. epidermidis | P. aeruginosa | E. cloacae | K. pneumoniae | E. coli | C. albicans | C. tropicalis | C. glabrata |
---|---|---|---|---|---|---|---|---|---|
Propolis extr1 | 18/0.95 | 19/0.90 | 16/1.10 | 16/1.15 | 17/1.03 | 14/1.34 | 12/1.40 | 13/1.28 | 14/1.25 |
Propolis extr2 | 13 | 12 | 10 | 10 | 9 | 8 | NA | NA | NA |
Netilmicin | 21/0.004 | 25/0.004 | 20/0.088 | 23/0.008 | 22/0.008 | 24/0.010 | NT | NT | NT |
Itraconazole | NT | NT | NT | NT | NT | NT | 20/0.01 | 22/0.001 | 23/0.0001 |
5-flucytosine | NT | NT | NT | NT | NT | NT | 21/0.01 | 22/0.001 | 24/0.0001 |
A549 | H23 | Caco-2 | DLD-1 | HT-29 | ||
---|---|---|---|---|---|---|
Propolis Extr1 | 1 μg/mL | 0 | 0 | 0 | 0 | 0 |
25 μg/mL | 59% ± 11 | 69% ± 1 | 96% ± 0.5 | 82% ± 2 | 35% ± 33 | |
50 μg/mL | 36% ± 34 | 78% ± 7 | 112% ± 60 | 49% ± 38 | 71% ± 14 | |
100 μg/mL | 23% ± 62 | 28% ± 7 | 67% ± 4 | 29% ± 55 | 60% ± 18 | |
Propolis Extr2 | 1 μg/mL | 5% ± 18 | 0 | 0 | 0 | 0 |
25 μg/mL | 19% ± 9 | 27% ± 1 | 0 | 74% ± 35 | 39% ± 29 | |
50 μg/mL | 48% ± 50 | 82% ± 37 | 5% ± 93 | 72% ± 55 | 40% ± 48 | |
100 μg/mL | 84% ± 60 | 68% ± 54 | 23% ± 103 | 110% ± 72 | 60% ± 57 | |
Doxorubicin | 20 μM | 0.3% ± 0.3 | 1.2% ± 1.2 | 0.3% ± 0.3 | 1.2% ± 1.2 | 0 |
100 μM | 22% ± 7 | 21% ± 6 | 22% ± 7 | 21% ± 6 | 17% ± 5 | |
Farmorubicin | 20 μM | 0 | 9% ± 9 | 0 | 9% ± 9 | 0 |
100 μM | 33% ± 18 | 28% ± 6 | 33% ± 18 | 28% ± 6 | 30% ± 8 |
MCF-7 | MDA-MB-468 | U87 | LN18 | L-929 | ||
---|---|---|---|---|---|---|
Propolis extr1 | 1 μg/mL | 0 | 0 | 0 | 0 | 0 |
25 μg/mL | 196% ± 183 | 57% ± 30 | 9% ± 0.5 | 50% ± 38 | 112% ± 58 | |
50 μg/mL | 170% ± 148 | 42% ± 23 | 50% ± 43 | 25% ± 3 | 95% ± 58 | |
100 μg/mL | 178% ± 154 | 40% ± 24 | 52% ± 42 | 52% ± 16 | 172% ± 14 | |
Propolis extr2 | 1 μg/mL | 6% ± 1 | 0 | 38% ± 39 | 15% ± 17 | 16% ± 33 |
25 μg/mL | 65% ± 57 | 0 | 7% ± 6 | 86% ± 85 | 202% ± 67 | |
50 μg/mL | 87% ± 72 | 13% ± 55 | 14% ± 3 | 64% ± 32 | 221% ± 7 | |
100 μg/mL | 146% ± 118 | 0 | 17% ± 0.5 | 92% ± 10 | 269% ± 62 | |
Doxorubicin | 20 μM | 121% ± 2 | 60% ± 38 | 0 | 121% ± 2 | 60% ± 38 |
100 μM | 177% ± 16 | 21% ± 10 | 17% ± 5 | 177% ± 16 | 21% ± 10 | |
Farmorubicin | 20 μM | 83% ± 33 | 16% ± 2 | 0 | 83% ± 33 | 16% ± 2 |
100 μM | 159% ± 9 | 38% ± 12 | 30% ± 8 | 159% ± 9 | 38% ± 12 |
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Popova, M.; Giannopoulou, E.; Skalicka-Woźniak, K.; Graikou, K.; Widelski, J.; Bankova, V.; Kalofonos, H.; Sivolapenko, G.; Gaweł-Bęben, K.; Antosiewicz, B.; et al. Characterization and Biological Evaluation of Propolis from Poland. Molecules 2017, 22, 1159. https://doi.org/10.3390/molecules22071159
Popova M, Giannopoulou E, Skalicka-Woźniak K, Graikou K, Widelski J, Bankova V, Kalofonos H, Sivolapenko G, Gaweł-Bęben K, Antosiewicz B, et al. Characterization and Biological Evaluation of Propolis from Poland. Molecules. 2017; 22(7):1159. https://doi.org/10.3390/molecules22071159
Chicago/Turabian StylePopova, Milena, Efstathia Giannopoulou, Krystyna Skalicka-Woźniak, Konstantia Graikou, Jaroslaw Widelski, Vassya Bankova, Haralabos Kalofonos, Gregory Sivolapenko, Katarzyna Gaweł-Bęben, Beata Antosiewicz, and et al. 2017. "Characterization and Biological Evaluation of Propolis from Poland" Molecules 22, no. 7: 1159. https://doi.org/10.3390/molecules22071159