Table 1
Chemical composition of propolis extracts depending on geographical origin
| Geographical origin | Botanical genus and/or species | Bee type | Majority compounds | References |
|---|---|---|---|---|
| Turkey (10 different regions) | ns | Apis mellifera | Aromatic alcohol, alcohol, aromatic acid, flavonoid† (flavone, flavanone, flavonol), ketone, terpene†, vitamin E, acid | [36] |
| Medellin, Antioquia, Colombia | ns | Apis mellifera | Isocupressic acid, (+)-agathadiol, epi-13-torulosol | [49] |
| ‘El Siambon’ Tucuman, Argentina | Salix humboldiana, Pinus, Eucalyptus | Apis mellifera | Pinocembrin*, galangin* | [33] |
| Baoding County, Hebei Province, China | ns | ns | Pinobanksin*, pinocembrin*, chrysin*, galangin* | [46] |
| Tehran-Khojir, northern Iran | Populus (determined by studying the chemical composition of propolis by GC-MS) | ns | Pinobanksin*, pinobanksin-3-acetate, pinocembrin*, pinostrobin, chrysin*, galangin* | [44] |
| Haramaya, Ethiopia | ns | Apis mellifera | Benzenamine, N,N-dibutyl-(21.94%), Paromomycin (9.74%), 4-Aminobutyramide,N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl]-(9.26%) and DL-Tryptophan,5-methoxy(7.43%) | [30] |
| Northeastern Brazil | Dalbergia ecastophyllum | Apis mellifera | Medicarpin, 3-hydroxy-8.9-dimethoxypterocarpan, quercetin, chrysin*, ferulic acid, artepillin C† | [42] |
| Cabreuva, State of Sao Paulo, Brazil | Baccharis dracunculifolia | Apis mellifera | Artepillin C, p-Coumaric acid, kaempferid | [21, 75] |
| Temuco, Chile | ns | ns | Pinocembrin*, caffeic acid*, myricetin, quercetin, kaempferol, apigenin, galangin*, caffeic acid phenyl ester (CAPE) | [39] |
| State de Parana, Brazil | Baccharis dracunculifolia + Auraucaria spp. | ns | 3,5-Diprenyl-4-hydroxycinnamic acid† (DHCA), 2,2-Dimethyl-6-carboxyethenyl-2H-1-benzopyran (DCBEN), 3-Prenyl-4-hydroxycinnamic acid† (PHCA), 2,2-Dimethyl-8-prenyl-2H-1-benzopyran-6-propenoic acid (DPB) | [76] |
| State of Minas Gerais, Brazil | Baccharis dracunculifolia | ns | 3,5-Diprenyl-4-hydroxycinnamic acid† (DHCA), 3-Prenyl-4-hydroxycinnamic acid† (PHCA), 2,2-Dimethyl-8-prenyl-2H-1-benzopyran-6-propenoic acid (DPB), p-Coumaric acid (PCUM), Caffeic acid* (CA), caffeoylquinic acid derivates† | [76], [77] |
| State of Parana, Brazil | Auraucaria spp. | ns | 3-Methoxy-4-hydroxy-benzaldehyde, (VAN), 3-Methoxy-4-hydroxycinnamalde-hyde (G2), 2-[1-hydroxymethyl]vinyl-6-acetyl-5-hidroxycumarane (I) | [76] |
| Isfahan, central Iran | ns | ns | Pinocembrin*, caffeic acid*, kaempferol, phenethyl caffeate, chrysin*, galangin* | [78] |
| England and New York State, USA | ns | ns | p-coumaric acid, chrysin*, pinocembrin* | [77] |
| Hatay region, Turkey | pine forest, eucalyptus, poplar trees | Apis mellifera syriaca, Apis mellifera anatoliaca, Apis mellifera caucasica | Caffeic acid*, sesquiterpenes† | [79] |
| Northeastern Portugal | ns | Apis mellifera | New compound: p-coumaric ester derivative dimer, methylated and/or sterified or hydroxylated derivatives of flavonoids, other compounds found in temperate zones | [80] |
| Greece | ns | ns | α-pinene | [81] |
| Temuco, Chile | ns | ns | Caffeic acid*, myricetin, quercetin, kaempferol, apigenin, pinocembrin*, galangin*, CAPE, rutin | [45] |
| Sonora, Mexico | ns | ns | Pinocembrin*, pinobanksin 3-acetate, chrysin*, CAPE†, acacetin, galangin* | [50] |
| Kangaroo Island, Australia | Acacia paradoxa | Apis mellifera | 2′,3′,4′-trimethoxychalcone 2′-hydroxy-3′,4′-dimethoxychalcone 2′,4′-dihydroxy-3′-methoxychalcone pinobanksin 3-acetate 5,7-dihydroxy-6-methoxy-2,3-dihydroflavonol 3-acetate, | [82] |
| Montevideo, Uruguay | ns | ns | Pinobanksin 3-(2-methyl)butyrate pinobanksin 3-isobutyrate2-methyl-2-butenyl ferulate | [83] |
| Okinawa, Japan | Macaranga tanarius | Apis mellifera | Nymphaeol-B, Isonymphaeol-B, Nymphaeol-A, 3′-geranyl-naringenin, Nymphaeol-C | [84] |
| Waikato, New Zealand | ns | ns | Pinobanksin*, pinocembrin*, chrysin*, galangin*, cinnamic and ferulic acid | [47] |
Table 2
Antifungal activity of propolis extracts against plant pathogens
| Geographical origin | Tested extract | Pathogen/Origin | Analysed parameter | Method | Results | References |
|---|---|---|---|---|---|---|
| Turkey | EEP | Aspergillus versicolor Penicillium aurantiogriseum (isolated from Turkish cheese) | Percentage of mycelium growth inhibition | Agar medium dilution method | Mycelium growth inhibition (%) EEP concentration 10%: 100% inhibition on all the samples and the 2 strains EEP concentration 5%: >30% inhibition EEP concentration 1%: >15% inhibition | [36] |
| Hamaraya, Ethiopia | EEP | Fusarium sp. Aspergillus niger (isolated from avocado) | Relative inhibition of mycelium growth | Agar medium dilution method | Significant inhibition at a concentration of 10 mg mL−1 for Aspergillus niger and Fusarium sp. | [30] |
| 5 different regions of Turkey | MEP | Alternaria alternata Fusarium oxysporum | Percentage of mycelium growth inhibition | Agar medium dilution method | Mycelium growth inhibition (%) as of D+3 F. oxysporum: 100% for 2 regions (at 2% and 5% concentration) >52% for the 3 others (from a 2% concentration) A. alternata. 100% for 2 regions at a 5% concentration | [25] |
| Temuco, Chile | EEP | Alternaria alternata Fusarium sp. Botrytis cinerea Penicillium expansum | Percentage of mycelium growth inhibition | Agar medium dilution method | 100% inhibition for all the fungi at an EEP concentration = 2.5% except for B.cinerea = at 5% Inhibition still better than with the chemical fungicide | [45] |
| Baoding County, Hebei Province, China | EEP P-Fr E-Fr B-Fr W-Fr | Penicillium italicum (isolated from citrus blue mould) | Percentage of mycelium growth inhibition | Agar medium dilution method | Mycelium growth inhibition (%) EEP extract (1200 mg L−1): 93.20% P-Fr extract (200 mg L−1): 35.40% E-Fr extract (200 mg L−1): 100% B-Fr extract (200 mg L−1): 25% W-Fr extract (200 mg L−1): 6.82% | [46] |
| Medellin, Antioquia, Colombia | EPEM CH2Cl2 EtOAc MeOH | Colletotrichum gloeosporioides (isolated from papaya (Carica papaya) and mango (Mangifera indica)) Botryodiplodia theobromae (isolated from avocado, Persea americana) | Percentage of mycelium growth inhibition | Agar medium dilution method | Mycelium growth inhibition (%) on C. gloeosporioides (mango), C. gloeosporioides (papaya), B. theobromae, respectively EPEM extract: 39.8%, 26.1%, 29% CH2Cl2 extract: 47.6%, 38.1, 23.5% EtOAc extract: 6.5%, 11.6%, 5.7% MeOH extract: 9.9%, 5.2%, 4.9% | [49] |
| Sao Paulo, Brazil | EEP | Colletotrichum gloeosporioides | Percentage of mycelium growth inhibition | Agar medium dilution method | Mycelium growth inhibition (%) EEP concentration 2.5%: total inhibition EEP concentration 0.5/1.0/1.5/2.0%: partial inhibition | [4] |
| China | EEP | Colletotrichum capsici (isolated from capsicum) | Percentage of mycelium growth inhibition | Agar medium dilution method | Mycelium growth inhibition (%) EEP concentration 0.25%: 66.1% inhibition EEP concentration 0.50%: 84.3% inhibition EEP concentration 0.75%: 89% inhibition | [64] |
| Tehran-Khojir, northern Iran | EEP | Aspergillus niger | Determination of MIC value | Liquid medium dilution method | MIC value (μg mL−1) Aspergillus niger: 500 | [44] |
| El-Aslogy, Zagazig, Egypt | EEP | Aspergillus flavus (isolated from pealed peanut seed) | Percentage of spore germination | Liquid medium dilution method | For EEP concentrations varying from 3 to 4g L−1: 56 to 76% reduction in spore germination percentage | [57] |
| San Juan province, Argentina | EEP | Aspergillus flavus Apsergillus niger | Determination of MIC value | Liquid medium dilution method | Species of the genus Aspergillus are not susceptible to extracts of urban propolis (MIC > 250 μg mL−1) | [58] |
| ‘El Siambon’ Tucuman, Argentina | PPPE | Aspergillus niger (isolated from citrus) Fusarium sp. Penicillium notatum | Determination of MIC value | Liquid medium dilution method | MIC value (μg mL−1) Aspergillus niger: 232 ± 0.12 Fusarium sp. (20), (21), (22) : 349 ± 0.15, 310 ± 0.10, 194 ± 0.10 Penicillium notatum: 349 ± 0.14 | [33] |
| Sao Paulo, Brazil | EEP | Colletotrichum gloeosporioides | Percentage of spore germination inhibition | Liquid medium dilution method | Spore germination inhibition (%) EEP concentration 0.5%: 1.78% inhibition EEP concentration 1.0%: 47.3% inhibition EEP concentration 1.5%: 96.4% inhibition EEP concentration 2.0%: 100% inhibition EEP concentration 2.5%: 100% inhibition | [4] |
| ‘El Siambon’ Tucuman, Argentina | PPPE | Aspergillus niger (isolated from citrus) Fusarium sp. Penicillium notatum | Percentage of mycelium growth inhibition | Paper disc diffusion method | Mycelium growth inhibition (%) Aspergillus niger: 60.4 ± 0.04 Fusarium sp. (20), (21), (22): 63.1 ± 0.03, 59.9 ± 0.03, 59.1 ± 0.04 Penicillium notatum: 44.6 ± 0.05 | [33] |
| ‘El Siambon’ Tucuman, Argentina | PPPE | Aspergillus niger (isolated from citrus) Fusarium sp. Penicillium notatum | Compounds displaying activity potential | TLC bioautography | Discovery of phenolic compounds | [33] |
| Baoding County, Hebei Province, China | EEP P-Fr E-Fr B-Fr W-Fr | Penicillium italicum (isolated from citrus blue mould) | Compounds displaying activity potential | TLC bioautography | Identification: pinobanksin, pinocembrin, chrysin, galangin | [46] |
[i] EEP, ethanol extract of propolis; EPEM, n-hexane/methanol extract of propolis; CH2Cl2, dichloromethane; EtOAc, ethyl acetate; MeOH, methanol; PPPE, partially purified propolis extract; P-Fr, petroleum ether fraction; E-Fr, ethyl acetate fraction; B-Fr, n-butanol fraction; W-Fr, water fraction; HPMC, hydroxypropylmethylcellulose.