Table 2.
Identified flavonoids, phenolic and terpen compounds in global propolis samples
| Country (Reference) | Geographic origin (year) | Flavonoids * | Phenolic compounds* | Terpens* |
|---|---|---|---|---|
| [28-30] | Lavark | Pinocembrin; kaempferol; chrysin; galangin | Caffeic acid; phenethyl caffeate | |
| Khojir (2003) | Pinostrobin; pinocembrin; pinobanksin-3-acetate; chrysin; pinobanksin; galangin; pinocembrin chalcone; kaempferol; pinobanksin-3-propanoate; quercetin; quercetin methyl ether | p-Coumaric acid; dimethyl caffeic acid; isoferulic acid; ferulic acid; caffeic acid; benzyl-p-coumarate; 1-phenylethyl trans-caffeate; cinnamyl caffeate; methyl-butenyl-ferulate; methyl-butenyl-isoferulate; methyl-butenyl-caffeate; methyl-butenyl-coumarate | δ-9-tetra-Hydrocannabinol acid | |
| Khojir (2004) | Pinostrobin chalcone; pinocembrin chalcone; pinocembrin; chrysin; galangin; pinobanskin butanoate; pinobanskin pentanoate; pinobanksin acetate; apigenin; kaempferol methyl ether; isosakuranetin | p-Coumaric acid; dimethoxycinnamic acid; ferulic acid; isoferulic acid; caffeic acid; penetyl caffeate; isopentenyl ferulate; dimethylallyl ferulate; isopentenyl caffeate; dimethylallyl caffeate; phenethyl caffeate; cinnamyl caffeate | Sesquiterpene; triterpene | |
| Telo (2003) | Pinostrobin chalcone; pinocembrin chalcone; pinocembrin; chrysin; galangin; pinobanskin butanoate; pinobanskin pentanoate; pinobanksin acetate; dihydroxymethoxy flavones; sakuranetin; pinobanskin | p-Coumaric acid; dimethoxy cinnamic acid; ferulic acid; isoferulic acid; caffeiccid; pentenyl-p-coumarate; beutenyl caffeate; penetyl caffeate; isopentenyl caffeate; hexyl-p-coumarate; dimethylallyl caffeate; hexyl caffeate | Eudesmol; α-bisabolol; diterpenic acid; triterpene | |
| [14,20,49] | Brejo Grande (2010) | 6-Acetyl-2,2-dimethyl-3-hydroxy chromen; 2-hydroxy-4-methoxy- chalcone; liquiritigenin; formononetin; medicarpin; hesperetin 7-rhamno glucoside; biochanin A; retusapurpurin B | - | - |
| Brotas, São paulo (2000) | - | Hydrocinnamic acid;p-hydroxybenzoic acid; p-cumaric acid; caffeic acid; o-cumaric acid; dihydroxy benzoic acid | Lupeol acetate; lupeol; lupenone; lanosterol; cycloartenol; friedour-7-en-3-one; friedour-7-en-3-ol; α-amyrin; β-amyrin; obtusifoliol; β-amyrin acetate | |
| Marde Espanha (2004) | Pinostrobin | Caffeic acid, cinnamic acid, ethyl hydro cinnamate, ferulic acid, hydrocinnamic acid | α-Amyrin; β-amyrin; β-amyrin acetate; amyrin 3-methoxy; glycyrrhizic acid; patchouli alcohol | |
| [62] | Different provinces (2003-2004) | Chrysin; pinocembrin; naringenin; sakuranetin; hesperetin; pinobanksin -3-acetate; pinobanksin-3-propionate | Vanillin; caffeic acid; gallaic acid; ferulic acid; ferulic acid methyl ester; isoprenyl coumarate; prenyl caffeate; isopentyl caffeate; isoprenyl ferulate; benzyl caffeate | - |
| [51] | Different provinces (2003-2004) | Isoliquiritigenin; liquiritigenin; formononetin; vestitol; neovestitol; isosativan; medicarpin; homo- pterocarpin; vesticarpan; 3-hydroxy-8, 9-dimethoxy pterocarpan; 3,4-dihydroxy-9-methoxy pterocarpan | - | Nemorosone; 24-methylene-9,19-ciclolanostan-3β-ol; α-amyrin; α-amyrone; β-amyrin; β-amyrinacetate; β-amyrone; cycloartenol; germanicol; germanicol acetate; lanosterol; lanosterol acetate; lupeol; lupeol acetate |
| [61] | Baniswief | Pinostrobin; pinocembrin; pinobankasin; pinobankasin-3-acetate; chrysin; galangin | trans-p-Coumaric acid; dimethyl caffeic acid; ferulic acid; caffeic acid; isopentenyl caffeate; dimethyl allyl caffeate; benzyl caffeate; dodecyl caffeate; tetradecylcaffeate; hexa decylcaffeate; tetradecenyl caffeate | Cycloartinol; lanosterol; β-amyrin; triterpene of β-amyrin type |
| Fayoum | Pinostrobin chalcone; pinocembrin chalcone; galangin; chrysin; Sakauranetin chalcone; pinobankasin; pinobankasin-3-acetate | diMethylcaffeic acid; caffeic acid; isopentenyl caffeate; 2-methyl-2-butenyl caffeate | - | |
| Asyut | Pinostrobin chalcone; pinocembrin; pinobankasin; chrysin | 4-Methoxy-cinnamic acid; dimethyl caffeic acid; isoferulic acid; caffeic acid;different derivatives of methyl-butenyl-coumarate;isopentenylcaffeate; 2-methyl-2-butenyl caffeate;3-methyl-2-butenyl caffeate | - | |
| Shouhag | Hexamethoxy flavone | p-Hydroxy benzoic acid; dimethyl caffeic acid; caffeic acid | Dehydroabietic acid;β-amyrin; triterpene of β-amyrin type | |
| [13,15,27,54] | Erzurum (Anatolia) | Naringenin; chrysin; acacetin | Ferulic acid; dimethyl caffeic acid; isoferulic acid; 4-vinylphenol; 2-Methoxy-4-vinyphenol | Chrysophanol; α-cadinol β-eudesmol; α-bisabolol; α-eudesmol; 2-naphtalenemethanol |
| Bursa and Hatay (2007) | Tectochrysin; pinocembrin; chrysin; 4H-1-benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl | Methylhomovanillate; isoferulic acid | Totarolone; hinokione; bicyclo(4.4.0) dec-1-ene; δ-cadinene | |
| Different provinces (2002-2003) | Isalpinin; pinocembrin; pinostropin; naringenin; 4´,5-dihydroxy-7-methoxy flavanone; chrysin; 3,4´,7-trimethoxy flavanone; pinobanksin; quercetin; galangine; apigenin | Ferulic acid; caffeic acid; isoferulic acid | 5-Azulenementhanol; α-bisabolol | |
| Kazan and marmaris (1996) | - | Ferulic acid; caffeic acid; caffeic acid isomers | 1-Naphthalene methanol, decahydro-1,10-dimethyl-6-methenyl-5-(5-hydroxy-3-Pentene); thunbergol; isopimaric acid; 3-α,5-β-pregnan-20-one; androstan-1,17-dimethyl-17-hydroxy-3-one; α-terpineol; 4-βH,5α-eremophi1D1(10)-ene; dehydroabietic acid; abietic acid; farnesol | |
| [14] | Burgas (2003) | Pinobanksin 3-butanoate; pinobanksin 3-etanoate; pinostrobin chalcone; chrysin; pinobanksin 3-pentanoate; pinocembrin | Benzyl caffeate; caffeic acid; dimethyl caffeic acid; ferulic acid; isoferulic acid;p-coumaric acid; pentenyl caffeate; pentenyl ferrulate; phenethylcaffeate | Squalene |
*
The bold compositions are common between different propolis samples collected from global regions. In comparasion with Table 1 (A and B), Iranian propolis from Chenaran, Taleghan, Morad Beyg, and Kalaleh (the present study) are rich in flavonoids, phenolic, and terpenes compounds similar to Cuban, Brazilian, and Egyptian propolis.