Propolis

Propolis (bee glue) has been used widely in folk medicine in some European countries (e.g., Denmark). It contains, among other things, well-known sensitizers such as cinnamic acid and vanillin. When a commercial propolis ointment was incorporated in the standard patch test series in a Danish dermatology department, 20 of 295 showed positive reactions (Petersen 1977). 

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Bienen-harz, n., -kitt, m. bee glue, propolis, -korbi m. beehive. -korb(koks)ofen, m. beehive (coke) oven, -wachs, n. beeswax. 

Pich-pech, n. common pitch, -wachs, n. propolis. 

Vorwachs, n. bee glue, propolis, vor-walken, v.t. scour (cloth), -walten, v.i. prevail, prMominate. -walzen, v.t. Metal.) rough down (blooms). 

Each plant tissue tends to have an obviously distinctive profile of flavonoids. The flavonoid content can reach about 0.5% in pollen, 10% in propolis, and about 6 mg/kg in honey. Havonoid aglycones appear to be present only in propolis and honey, while pollen contains flavanols in herosidic forms. The flavonoids in honey and propolis have been identified as flavanones and flavanones/flavanols (Campos et ah, 1990). The antimi-crobially active flavanone pinocembrine was foimd to be a major flavonoid in honey (Bogdanov, 1989). Amiot et ah (1989) studied two blossom and two honeydew Swiss honey samples and foimd that pinocembrine was the main flavonoid. Pinocembrine concentration varied between 2 and 3 mg/kg (Bogdanov, 1989). Berahia et ah (1993) analyzed sunflower honey samples and detected six flavone/flavols, four flavanone/ flavols, and pinocembrin, of which pinocembrin is the main flavonoid. The flavonoids in sunflower honey and propolis were characterized and assessed for their effects on hepatic drug-metabolizing enzymes and benzo [fl]pyrene-DNA adduct formation (Sabatier et ah, 1992 Siess et ah, 1996). 

Pinocembrin, chrysin, galangin, and pinobanksin are main flavonoids in honey and propolis. 

Some phenolic acids such as ellagic acid can be used as floral markers of heather honey (Cherchi et al., 1994 Ferreres et al., 1996a,b), and the hydroxyciimamates (caffeic, p-coumaric, and ferulic acids) as floral markers of chestnut honey (Cherchi et al., 1994). Pinocembrin, pinobanksin, and chrysin are the characteristic flavonoids of propolis, and these flavo-noid compounds have been found in most European honey samples (Tomas-Barberan et al., 2001). However, for lavender and acacia honeys, no specific phenolic compoimds could be used as suitable floral markers (Tomas-Barberan et al., 2001). Other potential phytochemical markers like abscisic acid may become floral markers in heather honey (Cherchi et al., 1994). Abscisic acid was also detected in rapeseed, lime, and acacia honey samples (Tomas-Barberan et al., 2001). Snow and Manley-Harris (2004) studied antimicrobial activity of phenolics. 

Martos, I., Cossentini, M., Ferreres, F., and Tomas-Barberan, F. A. (1997). Flavonoid composition of Tunisian honeys and propolis. J. Agric. Food Chem. 45, 2824—2829. 

Nagai, T., Sakai, M., Inoue, R., Inoue, H., and Suzuki, N. (2001). Antioxidative activities of some commercially honeys, royal jelly, and propolis. Food Chem. 75, 237-240. 

Siess, M. H., Le Bon, A. M., Canivenc-Lavier, M. C., Amiot, M. ]., Sabatier, S., Yaubert, S. Y., and Suschetet, M. (1996). Flavonoids of honey and propolis Characterization and effects on hepatic drug-metabolizing enzymes and benzoja] pyrene-DNA.. Agric. Food Chem. 44, 2297-2301. 

Chang CC, Yang MH, Wen HM and Chen JC. 2002. Estimation of total flavonoid content in propolis by two complementary colorimetric methods. J Food Drug Anal 10 178-182. 

Viuda-Martos M, Ruiz-Navajas Y, Femandez-Lopez J and Perez-Alvarez JA. 2008. Functional properties of honey, propolis, and royal jelly. J Food Sci 73(9) R117—R124. 

There is the often-overlooked group of polyphenols containing the derivatives of hydro-xycinnamic and hydroxybenzoic acids such as caffeic, chlorogenic, and gallic acids (Figure 29.8), which occur in food and exhibit certain antioxidant activity. For example, some caffeic acid esters isolated from propolis from honeybee hives showed antiinflammatory... 

Flavonoids in propolis have also been investigated by TLC using a silica stationary phase and various mobile phases. Samples of 14 propolis with different geographical origin were extracted with 80 per cent ethanol and analysed with normal-phase TLC. The retention data are compiled in Table 2.47. 

Using numerical taxonomy it was found that the best separations were obtained by chloroform-methanol-(98-100 per cent) formic acid (44.1 3 2.35) and n-hexane-ethyl acetate-glacial acetic acid (31 14 5, v/v) as mobile phases. As the flavonoid profile of the propolis samples showed considerable differences, the method has been proposed for the authenticity test and traceability of various propolis products [141]. 

I. Jasprica, A. Smolcic-Bubalo, A. Mornar and M. Medic-Saric, Investigation of the flavonoids in Croatian propolis by thin-layer chromatography. J. Plan. Chromatogr.—Mod. TLC 17 (2004) 95-101. 

Chapter 4 - Propolis has been used for as a traditional medicine in Eastern Europe as an antifungal, antimicrobial, antiviral, anti-inflammatory, and anticarcinogenic agent. The author isolated three cinamic acid derivatives and one flavanol derivative from Brazilian propolis and determined their structures by spectroscopic analysis. Results were assayed, the anticancer drug potential of these compounds to identify new drug candidates, by determining the... 

Antiproliferative Effects of Phenolic Compounds Isolated from Brazilian Propolis... 

To whom correspondence should be addressed Seung-Wan Lee - Seoul Propolis Research Institute, BI Center, KAERI, 150 Deokjin-dong, Yuseong-gu Daejeon 305-453, Korea, Tel +82-862-4888, Fax +82-862-4887, E-mail biovera hanmail.net. 

Keywords Brazilian propolis, MDA-MB-231, kaempferide, apoptosis, biosafety... 

Propolis is a resinous substance gathered by honeybees from various plants. It has been used as a traditional medicine since ancient times [9], as an anticarcinogenic [10], antifungal [11], antimicrobial [12], antiviral [13], and anti-inflammatory [14] agent. 

Several compounds have been isolated from propolis and among them, kaempferide has been reported to have several pharmaceutical functions, including melanogenesis inhibitor [15], antioxidant [16], and hypertension modulator [17], However, whether treatment of carcinoma cells with kaempferide has an antiproliferative effect is unclear as cancer study of it is rare until now. 

In this study, we isolated single compounds from propolis and determined whether they had an antiproliferative effect against carcinoma cells. 

Compound extraction and isolation The raw propolis (155 g) was soaked in 90% aqueous ethanol (1 L) for 1 week and the extraction was repeated twice. 

Drupanin (M.W 232.27), kaempferide (M.W 300.26), artepillin C (M.W 300.39), and baccharin (M.W 364.44) were isolated from Brazilian propolis. Raw propolis was extracted with 90% aqueous ethanol and the extract was fractionated on a reverse phase flash column. The bioactive fractions were subjected to preparative Ci8 HPLC to obtain four major compounds (Supplementary Figure 1). 

Figure 1. Chemical structure of compounds isolated from Brazilian propolis.

In this study, we conclusively show that all compounds isolated from Brazilian green propolis had proliferation inhibitive effects on both breast and prostate cancer cell lines at a concentration of 0.33 mM, with the exception of drupanin in MCF-7 breast cancer cells. 

In conclusion, kaempferide isolated from Brazilian propolis may be a potent anticancer agent although further study is needed to determine biological safety and clinical availability. 

Ozukul, Y., Silici, S. and Eroglu, E. (2005) Phytomedicine, The anticarcinogenic effect of propolis in human lymphocytes culture, 12, 742-747. 

Murad, JM., Calvi. SA., Soares, AMVC., Bankova, V. and Sforcin, JM. (2002) J. Ethnopharmacol., Effects of propolis from Brazil and Bulgaria on fungicidal activity of macrophages against Paracoccidiodes brasiliensis, 79, 331-334. 

Kartal, M., Yildiz, S., Kaya, S., Kurucu, S. and Topcu, G. (2003) J. Ethnopharmacol., Antimicrobial activity of propolis samples from two different regions of Anatolia. 86, 69-73. 

Amoros, M., Lurton, E., Boustie, J., Girre, L., Sauvager, F. and Cormier, M. (1994) J. Nat. Prod., Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. 57(5), 644-647. 

Simoes, LMC., Gregorio LE., Filho, AADS., Souza, MLD., Azzolini, AECS., Bastos, JK. and Lucisano-Valim, YM. (2004) J. Ethnopharm., Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils, 94, 59-65. 

Maruyama, H., Sumitou, Y., Sakamoto, T., Araki, Y. and Hara, H. (2009) Biol. Pharm. Bull., Antihypertensive effects of flavonoids isolated from Brazilian green propolis in spontaneously hypertensive rats, 32(7), 1244-1250. 

Aga, H., Shibuya, T., Sugimoto, T., Kurimoto, M. and Nakajima, S. (1994) Biosci. Biotech. Biochem., Isolation and identification of antimicrobial compounds in Brazilian propolis, 58, 945-946. 

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