Propolis is a honeybee product with broad clinical applications. Current literature describes that propolis is collected from plant resins. From a systematic database search, 241 compounds were identified in propolis for the first time between 2000 and 2012; and they belong to such diverse chemical classes as flavonoids, phenylpropanoids, terpenenes, stilbenes, lignans, coumarins, and their prenylated derivatives, showing a pattern consistent with around 300 previously reported compounds. The chemical characteristics of propolis are linked to the diversity of geographical location, plant sources and bee species.

https://www.mdpi.com/1420-3049/19/12/19610/pdf

Recent advances in the chemical composition of propolis.

Propolis is a natural resinous mixture produced by honey bees from substances collected from parts of plants, buds, and exudates. Due to its waxy nature and mechanical properties, bees use propolis in the construction and repair of their hives for sealing openings and cracks and smoothing out the internal walls and as a protective barrier against external invaders like snakes, lizards, and so forth, or against weathering threats like wind and rain. Bees gather propolis from different plants, in the temperate climate zone mainly from poplar. Current antimicrobial applications of propolis include formulations for cold syndrome (upper respiratory tract infections, common cold, and flu-like infections), wound healing, treatment of burns, acne, herpes simplex and genitalis, and neurodermatitis. Worldwide propolis has a tremendous popularity, but in India the studies over propolis have just started, not extensively reported except few regions of India like Maharashtra, West Bengal, Tamil Nadu, Gujrat, and Madhya Pradesh.

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Propolis: A Wonder Bees Product and Its Pharmacological Potentials

Chemical compositions and antimicrobial activities of four different Anatolian propolis samples.

Honeybees produce honey, royal jelly, propolis, bee venom, bee pollen, and beeswax, which potentially benefit to humans due to the bioactives in them. Clinical standardization of these products is hindered by chemical variability depending on honeybee and botanical sources, but different molecules have been isolated and pharmacologically characterized. Major honey bioactives include phenolics, methylglyoxal, royal jelly proteins (MRJPs), and oligosaccharides. In royal jelly there are antimicrobial jelleins and royalisin peptides, MRJPs, and hydroxy-decenoic acid derivatives, notably 10-hydroxy-2-decenoic acid (10-HDA), with antimicrobial, anti-inflammatory, immunomodulatory, neuromodulatory, metabolic syndrome preventing, and anti-aging activities. Propolis contains caffeic acid phenethyl ester and artepillin C, specific of Brazilian propolis, with antiviral, immunomodulatory, anti-inflammatory and anticancer effects. Bee venom consists of toxic peptides like pain-inducing melittin, SK channel blocking apamin, and allergenic phospholipase A2. Bee pollen is vitaminic, contains antioxidant and anti-inflammatory plant phenolics, as well as antiatherosclerotic, antidiabetic, and hypoglycemic flavonoids, unsaturated fatty acids, and sterols. Beeswax is widely used in cosmetics and makeup. Given the importance of drug discovery from natural sources, this review is aimed at providing an exhaustive screening of the bioactive compounds detected in honeybee products and of their curative or adverse biological effects.

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Therapeutic Properties of Bioactive Compounds from Different Honeybee Products.

Propolis is a potential source of natural antioxidants such as phenolic acids and flavonoids. Its wide biological effects have been known and used since antiquity. In the modern world natural substances are sought which would be able to counteract the effects of antioxidative stress, which underlies many diseases, such as cancer, diabetes and atherosclerosis. This paper aims to present the antioxidative activity of phenolic acids and flavonoids present in Polish propolis and the relationship between their chemical structure and antioxidative activity influencing its medicinal properties. Data concerning the biological activity of propolis are summarized here, including its antibacterial, anti-inflammatory, anticarcinogenic, antiatherogenic, estrogenic effects, as well as AIDS- counteracting and reparative-regenerative function.

http://www.molvis.org/molvis/v19/78/mv-v19-78.pdf

Structure and antioxidant activity of polyphenols derived from propolis.

Spectrometric analyses of flavonoids in twenty propolis samples collected from ten different geographic localities in northern Croatia using two complementary methods, are reported. Flavones and flavonols were determined using aluminum chloride and expressed as quercetine equivalent while flavanones were determined using 2,4-dinitrophenylhydrazine and expressed as naringenin. Contents of flavones and flavonols were similar for most samples and ranged from 2 to 2.3%, except for one sample with a concentration of 1.3% and one sample in which it was not possible to detect flavones and flavonols. The content of flavanones in propolis samples is very variable. 55% of samples contain flavanons between 15 and 24% and 45% of samples between 4 and 14%. Total levels of flavonoids in raw propolis samples ranged between 5 and 26%; for the majority of samples (75%), the total level of flavonoids ranged between 15 and 25.9%. The high variability of flavanone concentration will affect biological activity of propolis preparations.

/pdf/quantitative-analysis-of-the-flavonoids-in-raw-propolis-from-3x27xsviwq.pdf

Quantitative analysis of the flavonoids in raw propolis from northern Croatia

Propolis ethanolic solutions are the most used propolis products on the market for the treatment of minor ulcers in the mouth, angina, thrush or skin infections. Since it is still an unofficial drug in pharmacy, we analyzed the contents of flavonoids in ten commercially available ethanolic solutions of propolis from the Croatian market using two complementary colorimetric methods. Antimicrobial activities, determined with the diffusion method, against six bacterial species (Bacillus subtilis NCTC 8236, Staphylococcus aureus ATCC 25923, Streptococcus pyogenes ATCC 12204, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 10536, Pseudomonas aeruginosa ATCC 27853, and one yeast-like fungus Candida albicans ATCC 10231 were compared. Results of flavonoids analysis suggested that the contents of flavones and flavonols in the products were uniform and ranged from 0.14 to 0.41%, but the content of flavanones varied greatly from 0.43 to 18.78%. Total flavonoid content, as the sum of two colorimetric methods, in propolis products was between 0.78 and 18.92%, and most products had the flavonoids content below 9%. All products with the total flavonoids content above 1% showed antimicrobial activity against the four Gram-positive bacterial species tested, and against P. aeruginosa and the yeast-like fungus C. albicans. Total flavonoids contents, expressed as the sum of two colorimetric methods, could be useful methods for estimating the flavonoid contents of propolis products. Our results indicate that the quality of commercially available propolis products requires verification.

/pdf/flavonoid-analysis-and-antimicrobial-activity-of-xung5ncz4u.pdf

Flavonoid analysis and antimicrobial activity of commercially available propolis products.

The radioprotective effects of propolis and polyphenolic compounds from propolis on the radiation-induced mortality of mice exposed to 9 Gy of gamma-irradiation were studied. Intraperitoneal (i.p.) treatment of mice at doses of 100 mg kg(-1) body weight of propolis (water or ethanolic extract; WSDP or EEP) or its polyphenolic compounds (quercetin, naringin caffeic acid, chrysin) consecutively for 3 d before irradiation, delayed the onset of mortality and reduced the symptoms of radiation sickness. All test compounds provided protection against hematopoietic death (death within 30 d after irradiation). The greatest protection was achieved with quercetin; the number of survivors at the termination of the experiment was 63%. According to statistical analyses by the Kaplan-Meier method and the log-rank test, a significant difference between test components and control was found (p<0.001). Treatment with test components after lethal irradiation was ineffective. These results suggest that propolis and its polyphenolic compounds given to mice before irradiation protect mice from the lethal effects of whole-body irradiation.

https://www.jstage.jst.go.jp/article/bpb/30/5/30_5_946/_pdf

Assessment by survival analysis of the radioprotective properties of propolis and its polyphenolic compounds.

Thin-layer chromatography of ethanolic extract of propolis (EEP) from the continental and Adriatic regions of Croatia showed that 72.2% of propolis samples contain galangin, 88.8% of samples contain kaempferol, naringenin and apigenin and 66.6% of samples contain caffeic acid. Caffeic acid, pinocembrin, galangin, chrysin and naringenin were analyzed by HPLC. In all samples, pinocembrin was the dominant flavonoid. In samples from the Adriatic region, concentration of pinocembrin ranged from 0.03 to 6.14% (x = 2.87%) and in the continental region samples from 0 to 4.74% (x = 2.84%). Chrysin was found in all propolis samples in a concentration ranging from 0.22 to 5.32% (x = 1.86%) in the continental region samples and from 0.03 to 3.64% (x = 1.96%) in samples from the Adriatic region. Chrysin was followed by naringenin, ranging from 0 to 1.14% (x = 0.42%) in samples from the Adriatic region and from 0.22 to 2.41% (x = 0.60%) in the continental region samples. Concentration of caffeic acid ranged from 0 to 10.11% (x = 2.69%) in the Adriatic region samples and from 0.27 to 2.67% (x = 1.37%) in samples from the continental region of Croatia. Results of HPLC analyses suggest that propolis samples collected from various parts of Croatia do not differ markedly in contents of chrysin, pinocembrin, naringenin and galangin but differ in the concentration of caffeic acid. All EEPs significantly inhibited the growth of Bacillus subtilis in comparison with the control (80% ethanol) (p < 0.05), showing inhibition zones of 16 +/- 2 mm for samples from the continental region, and of 18 +/- 3 mm for samples from the Adriatic region. There was no significant difference in antimicrobial activity of EEPs from the continental and Adriatic regions of Croatia, suggesting that bactericidal activity depends on synergism of all phenolic compounds.

Analysis of propolis from the continental and Adriatic regions of Croatia.

The propolis of honeybee hives which is frequently used in phytomedicine, exhibits a wide spectrum of biological activities. Because plant sources have the biggest influence on the chemical and biological activities, the goal of present study was to compare two different chemotypes of propolis: poplar-type and alecrim-type, taking into the account geographical positions of hives and flora around hives (Croatian and Brazilian source of propolis). The influence of extraction methods (water and 80 vol % ethanol extraction) was also included in study. Ethanol was found to be better solvent for polyphenols than water. The Croatian raw propolis sample was richer in extractable substances and polyphenols than the Brazilian propolis sample. However, water extracted more polyphenols from Brazilian propolis. Comparative antimicrobial activity testing showed differences in inhibition zones of growth, and minimal inhibitory concentrations (MIC) between ethanol extracts from Croatian and Brazilian liophilized propolis. Lower MIC values of Croatian ethanol extract (which indicate more potent antimicrobial activity) was noticed against gram-negative bacterial species (E. coli and P. aeruginosa), as well as against yeast (C. albicans). Ethanolic extracts of propolis samples showed significantly more anti-oxidative activity using DPPH radical scavenging activity assay, as well as using  -carotene bleaching assay. Using electron paramagnetic resonance (EPR) spectroscopy with DPPH as source of electron spin, significant difference between ethanol and water extracts of Croatian and Brazilian propolis samples was found. Interestingly, source of propolis did not has the influence on anti-oxidative activity of propolis using EPR spectroscopy, but extraction method dramatically changes anti-oxidative potency of propolis. As complex mixture, kinetics of propolis extracts were neither kinetics of the first order nor pseudo-first order, what suggesting many different reaction pathways. The comparative study of two geographically and chemically different types of propolis showed interestingly anti-oxidant and antimicrobial differences of extraction method used.

Marina Bakmaz

Papers

Quantitative analysis of the flavonoids in raw propolis from northern Croatia

Flavonoid analysis and antimicrobial activity of commercially available propolis products.

Assessment by survival analysis of the radioprotective properties of propolis and its polyphenolic compounds.

Analysis of propolis from the continental and Adriatic regions of Croatia.

Antimicrobial and antioxidant activity of propolis from Croatia and Brazil: a comparative study