From: Propolis volatile compounds: chemical diversity and biological activity: a review
Method of isolation* | Geographic origin | Percentage% (W/W) | Main constituents | Bioactivity | Reference | Year |
---|---|---|---|---|---|---|
DE | Albania | 0.3 | cadinene (10.5%), methoxyacetophenone (9.0%), sesquiterpene alcohol M = 222 (18.5%) | NT** | [17] | 1994 |
DE | Bulgaria | 0.3 | β-eudesmol (8.8%), δ-cadinen (5.3%), sesquiterpene alcohol M = 222 (15.5%) | Antibacterial | 1994, 1999 | |
DE | China (Inner Mongolia) | NA*** | α –bisabolol (20.1%), 2-methyl-3-buten-2-ol (10.8%), 3-methyl-2-butene-1-ol (8.3%) | NT | [21] | 2009 |
DE | Mongolia | 0.6 | benzyl benzoate (8.6%), Sesquiterpene alcohol M = 222 (15.7%) | NT | [17] | 1994 |
DE | Brazil, stingless bees | 0.1 | Tetragona: nerolidol (12.3%), spatulenol (10.4%); | antibacterial | [22] | 1999 |
Melipona quadrifasciata – p-cimen-8-ol (11.4); | ||||||
M. comperittes – ethylphenol (10.2%) | ||||||
DE | Mexico (Yucatan) | 0.02 | α-pinene (11.9%), hexadecanoic acid (10.9%), trans-verbenol (7.0%) | NT | [23] | 2006 |
DE | Mexico (Yucatan), stingless bees | 0.4 | α-pinene (17.6%), β-caryophyllene (11.8%), spatulenol (9.7%), caryophyllene oxide (9.5%), β-bourbonene (9.2%) | NT | [23] | 2006 |
DE | Canary islands | 0.1-0.3 | nerolidol (3.2 – 11.0%), spatulenol (3.2 – 8.4%), ledol (1.6 – 3.8%) | Antibacterial | [24] | 2000 |
HD | Croatia | 0.2 | limonene (6.4 – 10.5%), benzyl alcohol (3.1 – 18.2%), benzyl benzoate (3.6 – 4.4%) | NT | [25] | 1996 |
HD | Czech Republic | NA* | benzoic acid, benzyl alcohol, vanillin, eugenol | NT | [13] | 1974 |
HD | Greece | 0.03-0.1 | α –pinene (7.9 – 45.8%), trans-β-terpineol (2.2 – 6.6%), Junipene (1.5 – 11.7%), δ-cadinene (0.3 – 8.4) | Antibacterial | [26] | 2007 |
HD | Hungary | 0.3–1.5 | β-eudesmol, benzyl benzoate (2 types, one richer in benzyl benzoate) | Antibacterial | [16] | 1988 |
HD | India (Maharashtra state) | 3.2 | tricosane (13.6%), hexacosane (11.5%), palmitic acid (8.5%), linalool (6.7%), methyleugenol (6.0%) | Repellent activity against the honeybee Apis florea | [27] | 2013 |
HS, HD | Italy (Northern) | NA | benzoic acid (3.1 – 30.1%), benzyl benzoate (0.2 – 13.1%), β-eudesmol (2.9 – 12.9%), δ-cadinene (1.3 – 13.3%), γ-cadinene (1.4 – 8.9%), Т-cadinol (2.7 – 10.0%), α-cadinol (4.8 – 9.7%) | NT | [18] | 2013 |
HD | Portugal | 0.05 | viridiflorol (9.0 – 39.0%), n-tricosane (5.3%), n-nonadecane (4.0 – 18.0%) | NT | [28] | 2013 |
HD | China (Inner Mongolia) | NA | 3-methyl-2-buten-1-ol (26.8%), phenylethyl alcohol (17.1%), 2-methoxy-4-vinylphenol (9.5%) | NT | [21] | 2009 |
HD | Brazil | 0.4 | spatulenol (3.0 – 13.9%), (2Z,6E)-farnesol (1.6 – 14.9%), prenyl-acetophenone (0.2 – 8.7%), benzyl benzoate (0.3 – 18.3%) | NT | [29] | 1998 |
HD | Brazil | 0.1 | β-caryophyllene (12.7%), acetophenone (12.3%) | Antibacterial | [30] | 2010 |
HD | Brazil | NA | nerolidol (6.6%), trans-caryophyllene (4.1), spatulenol (3.6%) | NT | [31] | 2008 |
HD | Brazil (Minas Gerais State) | (E)-nerolidol (17.1%), β-caryophyllene (13.4%), selina-3,7(11) diene (10.4%) | NT | [32] | 2008 | |
HD | Brazil (Teresina, Piaui State) | NA | 1,8 – cineole (24.0%), exo-fenchol (11.3%), terpinen-4-ol (7.7%) | NT | [33] | 2008 |
HD | Brazil (Piaui State) | NA | α-pinene (0.3 – 34.4%), E-caryophyllene (2.6 – 17.4%), α-copaene (3.6 – 7.5%) | NT | [33] | 2008 |
HD | Brazil (Rio de Janeiro State) | 0.04 | α-pinene (18.3%), β-pinene (6.5%), δ-cadinene (7.0%) | Antifungal | [34] | 2010 |
HD | Brazil (Rio Grande do Sul State) | 3-3.8 | α-pinene (57.0 – 63.0%), β-pinene (12.5 – 30.8%), limonene (1.5 – 11.2%) | Antibacterial | [35] | 2012 |
HD | Ethiopia (Assela) | 0.9 | 5,6,7,8-tetramethylbicyclo [4,1,0] hept-4-en-3-one (15.0%), acoradiene (13.8%), epicedrol (6.8%) | NT | [36] | 2012 |
HD | Ethiopia (Haramaya) | 1.2 | calamenene (13.8%), 4-terpineol (8.6%), epi-bicyclosesquiphellandrene (8.4%) | NT | [36] | 2012 |
SHS | Estonia | NA | eucalyptol (25.9%), α-pinene (20.6%), benzaldehyde (10.8%), β-pinene (8.9%) | NT | [37] | 2014 |
SHS | China | NA | 3-methyl-3-butene-1-ol (40.3%), 3-methyl-2-butene-1-ol (11.6%), 4-penten-1-yl acetate (9.0%), α-longipinene (9.4%) | NT | [37] | 2014 |
SHS | Brazil | NA | α-pinene (52.5%), β-pinene (20.8%) | NT | [37] | 2014 |
SHS | Uruguay | NA | α-pinene (23.0 – 53.4%), β –pinene (24.1 – 27.4%), limonene (2.1 – 15.6%) | NT | [37] | 2014 |
HS | Italy (Southern) | NA | α-pinene (13.2%), germacrene D-4-ol (6.3%) | NT | [18] | 2013 |
HS | UK (Wales) | NA | 6-methylheptyl-5-en-2-one (16.0%), benzyl alcohol (14.2%), benzaldehyde (9.0%) | NT | [38] | 1989 |
HS | Argentina (Andean region) | NA | O-cimene, limonene | NT | [39] | 2011 |
DHS | China (Inner Mongolia) | NA | heptadecane (7.0%), phenantrene (4.0%) | NT | [21] | 2009 |
DHS | China (Heilongjiang, Beijing) | NA | acetic acid (44.3 - 60.0%), benzyl alcohol (7.3 - 13.9%) | NT | [40] | 2013 |
DHS | China (Shanghai) | NA | acetic acid (25.3%), cedrene (10.4%), 3-methyl-3-buten-1-ol (7.1%) | NT | [40] | 2013 |
DHS | China (Shandong) | NA | acetic acid (11.4%), 1-(1,5-dimethyl-4-hexenyl)-4-methyl-benzene (9.7%), 1,2,3,4, 4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)-naphthalene (8.3%), benzyl alcohol (7.4%) | NT | [40] | 2013 |
HS-SPME | Turkey (Eastern Anatolia) | NA | phenyl ethyl alcohol (7.7%), benzyl alcohol (7.4%), decanal (6.7%), ethyl benzoate (6.5%) | Antimicrobial, antioxidant | [41] | 2013 |
HS-SPME | Turkey (North Eastern Anatolia) | NA | cedrol (7.0 - 15.6%), α-bisabolol (14.3%), δ-cadinene (2.7 - 5.6%) | Antimicrobial, antioxidant | [41] | 2013 |
HS-SPME | Turkey (South Eastern Anatolia) | NA | α –terpinene (21.8%), α –terpineol (12.3%), junipene (9.1%), cinnamyl alcohol (8.7%), β-cariophyllene (8.1%) | NT | [42] | 2004 |
Brazil, stingless Friesomelita | Bee legs samples | manool, totarol | NT | [43] | 2002 | |
Extraction | France | 0.5 | β-eudesmol (30.0%), guaiol (10.0%), benzyl benzoate (8.0%) | NT | [15] | 1981 |
SD | Poland (Southern) | 1.2 of ethanol extract | farnesol, dihydroeudesmol, guaiol | antibacterial | [44] | 1983 |
UAE | Brazil | 5.4 in raw 0.3 in ethanol | nerolidol (10.4 – 14.7%), benzenepropanoic acid (14.9 – 20.8%) | NT | [45] | 2013 |
MAE | Brazil | longipinene (24.9%), α-eudesmol (6.9%), β-eudesmol (6.1%), β-caryophyllene (5.3%) | Therapeutic effect on anxiety | [46] | 2012 |