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Table 1 Propolis volatiles from different geographic origin

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

[17, 20]

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

  1. *DE Distillation-extraction; HD hydrodestilation; SHS static headspace; HS headspace; DHS dynamic headspace; HS-SPME headspace solid-phase microextraction; SD steam destilation; UAE ultrasonic assisted extraction; MAE microwave assisted extraction. ** NT not tested; *** NA not available.