Table 1.

Chemical composition of raw propolis

Class	Compounds
Alcohols	Benzene methanol, cinnamyl alcohol, glycerol; a-glycerophosphate; hydroquinone; isobutenol, phenethyl alcohol; prenyl alcohol [176, 177, 353]
Aldehydes	Benzaldehyde; caproiealdehyde; p-hydroxybenzaldehyde; isovanillin; protocatechuic aldehyde; vanillin [176, 353–356]
Aliphatic acids and aliphatic esters	Acetic acid; angelic acid; butyric acid; crotonic acid; fumaric acid; isobutyric acid; methylbutyric acid; isobutyl acetate; isopentyl acetate; isopentenyl acetate [176]
Amino acids	Alanine; β-alanine; α-aminobutyric acid; 6-aminobutyric acid; arginine; asparagine; aspartic acid; cystine; cysteine; glutamic acid; glycine; histidine; hydroxyproline; isoleucine; leucine, lysine; methionine; ornithine; phenylalanine; proline; pyroglutamic acid, sarcosine; serine; threonine, tryptophan; tyrosine; valine [49, 50, 176, 357]
Aromatic acid	p-Anisic acid; benzoic acid; caffeic acid; cinnamic acid; coumaric (-o,-m,-p) acid; 3,4-dimethoxycinnamic acid; ferulic acid; gallic acid; gentisic acid; hydroxycinnamic acid; p- hydroxybenzoic acid; isoferulic acid; 4-methoxycinnamic acid; protocatechuic acid; salicylic acid; vanillic acid; veratric acid [176, 177, 353–356, 358, 359]
Aromatic esters	Benzyl acetate, benzyl benzoate, benzyl caffeate, benzyl coumarate; benzyl-3,4-dimethoxycinnamate; benzyl ferulate; benzyl isoferulate; benzyl salicylate; butenyl caffeate; butyl caffeate; cinnamyl benzoate; cinnamyl caffeate; butyl caffeate; cinnamyl coumarate; cinnamyl isoferulate; ethyl benzoate; ethyl caffeate; methyl benzoate; 2-methyl-2-butenyl caffeate; 3-methyl-2-butenyl caffeate; 3-methyl-3-butenyl caffeate; 3-methyl-3-butenyl coumarate; 3-methyl-2 -butenyl ferulate; 3-methyl -3-butenyl ferulate; 2-methyl-2-butenyl isoferulate, 3-methyl-3-butenyl isoferulate; methyl salicylate; phenyl ethyl caffeate: phenyl ethylcoumarate; phenyl–ethyl isoferulate; pentyl caffeate; pentenyl caffeate, pentenyl ferulate; prenyl caffeate; prenyl coumarate; prenyl ferulate; prenyl isoferulate [176, 177, 353, 358, 359]
Chalcones and dihydrochalcones	Alpinetin chalcone; naringenin chalcone; pinobanksin chalcone, pinobanksin-3-acetate chalcone; pinocembrin chalcone; pinostrobin chalcone; sakuranetin chalcone; 2',4’,6' -trihydroxy-4'-methoxychalcone; 2',6'-dihydroxy-4'-methildihydrochalcone; 2’,4',6’- trihydroxydihydrochalcone [176, 177, 353, 359]; 3,4,2',3'-tetrahydroxychalcone [360], isoliquiritigenin, 4,4'-dihydroxy-2'-methoxychalcone; 4,2',4',alpha-tetrahydroxydihydrochalcone, 2',4'-dihydroxychalcone [361]
Flavanones	Naringenin; pinobanksin; pinobanksin-3-acetate; pinobanksin-3-butyrate; pinobanksin-3-hexanoate, pinobanksin-3-methyl ether; pinobanksin-3-pentanoate; pinobanksin-3-pentenoate; pinobanksin-3-propanoate; pinocembrin; pinostrobin; sakuranetin; 3,7-dihydroxy-5-methoxytlavanone; 2,5-dihydroxy-7-methoxyflavanone [49, 176, 177, 355, 359, 362–364]; 5,7-dihydroxy-6-methoxy-2,3-dihydroflavonol-3-acetate [365], 5-methoxy-3-hidroxyflavanone [366], (2R, 3R)-3,6,7-trihydroxyflavanone [367], alnustinol, (2R,3R)-3,7-dihydroxy-6-methoxyflavanone, garbanzol, (2R,3R)-3,7-dihydroxyflavanone, (2S)-dihydrooroxylin A, (2S)-dihydrobaicalein, (2S)-nNaringenin, (2S)-7-hydroxy-6-methoxyflavanone, (2S)-liquiritigenin, (2S)-7-hydroxyflavanone [361], sophoraflavanone A, solophenol A, bonannione A [368], sigmoidin B, propolin E, propolin B, propolin A [369], 5,7,3',4'-tetrahydroxy-2'-C-geranyl-6-prenlyflavanone, 5,7,3',4'-tetrahydroxy-2'-C-geranylflavanone, 5,7,3',4'-tetrahydroxy-6-C-geranylflavanone, 5,7,3',4'-tetrahydroxy-5'-C-geranylflavanone [48]; 3',4',6-trihydroxy-7-methoxy flavanone [367], (2R,3R)-6[1-(4'-hydroxy-3'-methoxyphenyl) prop-2en-1-yl]-pinobanksin-3-acetate, (2R,3R)-6[1-(4'-hydroxy-3'-methoxyphenyl) prop-2en-1-yl] pinobanksin [370], (2R,3R)-3,5-dihydroxy-7-methoxyflavanone 3-(2-methyl)-butyrate [97]; 7-O-prenylpinocembrin, 7-O-prenylstrobopinin [371]; pinobanksin-5-methyl-ether-3-O-pentanoate, hesperitin-5,7-dimethyl ether [366], (2S)-5,7-dihydroxy-4'-methoxy-8-prenylflavanone [368], 3-O-[(S)-2-methylbutyroyl] pinobanksin [372]
Flavones and flavonols	Acacetin; apigenin; apigenin-7-methyl ether; chrysin, fisetin; galangin; galangin-3-methyl ether; izalpinin; isorhamnetin; kaempferide; kaempferol; kaempterol-3-methyl ether; kaempferol-7-methyl ether; kaempferol-7,4’-dimethyl ether; pectolinarigenin; quercetin; quercetin-3,7-dimethyl ether; ramnetin; ramnocitrin, tectocrisin [49, 176, 177, 353–356, 364]; luteolin [373]; 6-cinnamylchrysin [372]; 3',5-dihydroxy-4',7-dimenthoxy flavones [374]; hexamethoxy flavones [375]; (7''R)-8-[1-(4'-hydroxy-3'-methoxyphenyl) prop-2-en-1-yl] chrysin [97]; (7"R)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin [97]; macarangin [376]; 2'-geranylquercetin, 8-(8"-hydroxy-3",8"-dimethyl-oct-2"-enyl)-quercetin, 2'-(8"-hydroxy-3",8"-dimethyl-oct-2"-enyl)-quercetin [368]
Isoflavones	4',7-dimethoxy-2'-isoflavonol, medicarpin, homopterocarpin, 7,4'-dihydroxyisoflavone [377], calycosin [361], 5,7-dihydroxy-4'-methoxyisoflavonoid, 7-hydroxy-4'-methoxyisoflavonoid [378], 7,3'-dihydroxy-6,5'-methoxyisoflavonoid, 6,7,3'-trihydroxy-4'-methoxyisoflavonoid, 7,3',4'-trihydroxy-5'-methoxyisoflavonoid, odoratin [367]; biochanin [379], (3R)-4'-Methoxy-2',3,7-trihydroxyisoflavanone, (3S)-ferreirin, (3S)-violanone, (3S)-vestitone, 2'-hydroxybiochanin A, pratensein, biochanin A, xenognosin B, formononetin, daidzein [361]
Flavans and Isoflavans	8-[(E)-4-phenylprop-2-en-1-one]-(2R,3S)-2-(3,5-dihydroxyphenyl)-3,4-dihydro-2H-2-be-nzopyran-5-methoxyl-3,7-diol, 8-[(E)-4-phenylprop-2-en-1-one]-(2S,3R)-2-(3,5-dihydroxyphenyl)-3,4-dihydro-2H-2-benzopyran-5-methoxyl-3,7-diol, 8-[(E)-4-phenylprop-2-en-1-one]-(2R,3S)-2-(3-methoxyl-4-hydroxyphenyl)-3,4-dihydro-2H-2-benzopyran-5-methoxyl-3,7-diol [380]; 3-hydroxy-5,6-dimethoxyflavan [381]; (3S)-vestitol, (3S)-isovestitol, (3S)-7-O-methylvestitol, (3S)-mucronulatol [361]; 7,4'-dihydroxy-2'-methoxyisoflavone [378]; neovestitol [379]
Open-chain neoflavonoids and other flavonoids	(S)-4-methoxydalbergione, (S)-3',4'-dihydroxy-4-methoxydalbergione, (S)-3'-hydroxy-4-methoxydalbergione [367], neoflavonoid 1–10 [382], (Z)-1-(2'-methoxy-4',5'dihydroxyphenyl)-2-(3-phenyl)propene, 1-(3',4'-dihydroxy-2'-methoxyphenyl)-3-(phenyl)propane [381], 2-(2',4'-dihydroxyphenyl)-3-methyl-6-methoxybenzofuran, 2,6-dihydroxy-2-[(4-hydroxyphenyl)methyl]-3-benzofuranone [361]
Hydrocarbon esters ethers, hydroxyl and keto waxes	Heneicosane; hentriacontane; heptacosane; hexacosane; nonacosane; pentacosane; tricosane; tripentacontane; tritriacontane; dotriacontyl hexadecanoate; dotriacontyl-[(Z)-octadec-9-enoate]; hexacosyl hexadecanoate; hexacosyl-[(Z)-octadec-9-enoate]; octacosylhexa decanoate; octacosyl-[(Z)-octadec-9-enoate] tetracosyl-hexadecanoate; tetracosyl-[(Z)-octadec-9-enoate]; tetratriacontyl-hexadecanoate tetratriacontyl-[(Z)-octadec-9-enoate]; triacontyl-hexadecanoate; triacontyl–[(Z)-octadec-9-enoate] [177, 353, 383, 384]
Pterocarpins (a type of neoflavonoid)	(6aR,11aR)-4-methoxymedicarpin, 6a-ethoxymedicarpin, 3,10-dihydroxy-9-methoxypterocarpan [361], 3,4-dihydroxy-9-methoxypterocarpan, 3-hydroxy-8,9-dimethoxypterocarpan, 3,8-dihydroxy-9-methoxypterocarpan, 4'-methoxy-5'hydroxyvesticarpan, homopterocarpin, 4-hydroxymedicarpin, medicarpin [378]
Fatty acids	Arachid acid; behenic acid; cerotic acid; lauric acid; linoleic acid; lignoceric acid; montanic acid; myristic acid; oleic acid; palmitic acids; stearic acid [177, 353, 359, 383]
Ketones	Acetophenone; p-acetophenolacetophenone; dihydroxy-acetophenone; methylacetophenone; hept-5-en-2-one; 6-methylketone [177, 353, 359]
Terpenoids and other compounds	α-Acetoxibetulenol; β-bisabolol; 1,8-cineole; α-copaene; cymene; limonene; pterostilbene; styrene; xanthorreol; xylitol; naphthalene; 4-hexanoIactone; sesquiterpene alcohol; sesquiterpene diol [49, 177, 353, 354, 363]; linalool [385], trans-β-terpineol [386], camphor [387]; junipene [386], γ-elemene, α-ylangene, valencene [385], 8-βH-cedran-8-ol, 4-βH,5α-eremophil-1(10)-ene, α-bisabolol, α-eudesmol, α-cadinol [388], patchoulene, manoyl oxide, ferruginol, ferruginolone, 2-hydroxyferruginol, 6/7-hydroxyferruginol, sempervirol, abietic acid, 18-succinyloxyabietadiene, 18-succinyloxyhydroxyabietatriene, 18-hydroxyabieta-8,11,13-triene, imbricataloic acid, diterpenic acid, neoabietic acid, labda-8(17),12,13-triene, hydroxydehydroabietic acid, dihydroxyabieta-8,11,13-triene, 13(14)-dehydrojunicedric acid, dehydroabietic acid, 18-hydroxyabieta-8,11,13-triene [389], junicedric acid, 14,15-dinor-13-oxo-8(17)-labden-19-oic acid, tran-communal, palmitoyl isocupressic acid, oleoyl isocupressic acid, 13-hydroxy-8(17),14-labdadien-19-oic acid, 15-oxolabda-8(17),13(E)-dien-19-oic acid, pimaric acid, totarolone [390]; lupeol alkanoates, lupeol, 24-methylene-9,19-ciclolanostan-3β-ol [391], lupeol acetate, lanosterol, germanicol acetate, germanicol, β-amyrin acetate, β-amyrone, α-amyrin acetate, α-amyrone [392], lanosterol acetate [375], (22Z,24E)-3-Oxocycloart-22,24-dien-26-oic acid, (24E)-3-oxo-27,28-dihydroxycycloart-24-en-26-oic acid [393], 3,4-seco-cycloart-12-hydroxy-4(28),24-dien-3-oicacid, cycloart-3,7-dihydroxy-24-en-28-oic acid [390], 3-oxo-triterpenic acid methyl ester [394]; 2H-cyclopentacyclooctene,4,5,6,7,8,9-hexahydro-1,2,2; 3-tetramethyl; germanicol; dimethyl-1,3,5,6-tetramethyl-[1,3-(13C2)] bicycle; dodeca-1,3,5,6,8,10-hexaene-9,10-dicarboxylate; spiro[benzo[α]cyclopenta [3, 4]cyclobuta[1,2-c]cycloheptene-8(5H),2'-[1,3]dioxane]; 6,7,7β,10α-tetrahydro-1; 14-methyl-cholest-7-en-3-ol-15-one; (3α,4α)- 4-methyl-stigmast-22-en-3-ol [28]
Lignans	Tetrahydrojusticidin B, 6-methoxydiphyllin, phyllamricin C [376]
Phenylpropanoids	cis-3-Methoxy-4-hydroxycinnamic acid, trans-3-methoxy-4-hydroxycinnamic acid [395]; 3-prenyl cinnamic acid allyl ester, p-methoxycinnamic acid, dihydrocinnamic acid, 3-methyl-2-butenyl isoferulate, 3-methyl-3-butenyl caffeate, hexadecyl caffeate [396]; 3-prenyl-4-hydroxycinnamic acid, 3,5-diprenyl-4-hydroxycinnamic acid [397]; methyl(E)-4-(4'-hydroxy-3'-methylbut-(E)-2'-enyloxy) cinnamate [398]; tetradecenyl caffeate (isomer), tetradecenyl caffeate [375]; 2-methyl-2-butenyl ferulate [48]
Chlorogenic acids	4-Feruoyl quinic acid [399]; 5-ferruoyl quinic acid [373]; 3,4,5-tri-O-caffeoylquinic acid [400]
Stilbenes	5'-Farnesyl-3'-hydroxyresveratrol [368]; schweinfurthin A, B [376]; 5,4'-dihydroxy-3'-methoxy-3-prenyloxy-E-stilbene, 3,5,3',4'-tetrahydroxy-2-prenyl-E-stilbene, 3,5,4'-trihydroxy-3'-methoxy-2-prenyl-E-stilbene, 5,3',4'-trihydroxy-3-methoxy-2-prenyl-E-stilbene, 5,4'-dihydroxy-3,3'-dimethoxy-2-prenyl-E-stilbene, 5,4'-dihydroxy-3-prenyloxy-E-stilbene, 3',4'-dihydroxy-E-stilbene, 3',4'-dihydroxy-3,5-dimethoxy-E-stilbene, diprenylated dihydrostilbene, 3,5-dihydroxy-2-prenyl-E-stilbene, 4-prenyldihydroresveratrol, 3-prenylresveratrol [398]; ( +)-pinoresinol dimethyl ether, ( +)-pinoresinol, ( +)-syringaresinol [361]
Other phenolics	8-(Methyl-butanechromane)-6-propenoic acid, 3-hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid, 2,2-dimethyl-8-prenylchromene-6-propenoic acid, 2,2-dimethylchromene-6-propenoic acid, 2,2-dimethyl-6-carboxyethnyl-2H-1-benzopyran, 2,2-dimethyl-6-carboxyethenyl-8-prenyl-2H-1-benzopyran [401]; nemorosone, 7-epi-clusianone, xanthochymol, gambogenone, hyperibone A [402]; 5-pentadecylresorcinol, 5-(8'Z,11'Z-heptadecadienyl)-resorcinol, 5-(11'Z-heptadecenyl)-resorcinol, 5-heptadecylresorcinol [95]; 1,3-bis(trimethylsilylloxy)-5,5-proylbenzene, 3,4-dimethylthioquinoline, 4-oxo-2-thioxo-3-thiazolidinepropionic acid, D-glucofuranuronic acid, dofuranuronic acid, 3-quinolinecarboxamine [403], baccharin [20], suberosin, tschimgin, tschimganin, bornyl p-hydroxybenzoate, bornyl vanillate, ferutinin, tefernin, ferutinol p-hydroxybenzoate, ferutinol vanillate [387]; 2-acetoxy-6-p-methoxybenzoyl jaeschkeanadiol, 2-acetoxy-6-p-hydroxybenzoyl jaeschkeanadiol [404]
Steroids	Calinasterol acetate; β-dihydrofucosterol acetate; ucosterol acetate; stigmasterol acetate [178]
Sugars	Fructofuranose-1; fructofuranose-2; α-D-glucopyranose; β-D-glucopyranose [177, 353, 358]; galactitol, gluconic acid, galacturonic acid and 2-O-glycerylgalactose [394]