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. 2022 Nov 9;27(22):7686. doi: 10.3390/molecules27227686

Table 3.

Group composition of diethyl ether extracts of Argentine propolis of SLBs (1—S. postica; 2—T. clavipes; 3—M. quadrifasciata quadrifasciata; 4—T. fiebrigi).

Group of Compounds Relative Composition (% of TIC)
1 2 3 4
Monoterpenoids, including: - * 1.10 (11) ** 4.09 (20) -
  • -

    α-Pinene

 - 0.86 1.89 -
  • -

    β-Pinene

 - 0.29 0.73 -
  • -

    Camphene hydrate

 - 0.06 0.16 -
Sesquiterpenoids, including: trace *** (5) 2.06 (20) 0.23 (3) -
  • -

    β-Caryophyllene

 trace 0.32 - -
  • -

    Germacrene D

 - 0.36 - -
  • -

    Bicyclogermacrene

 - 0.11 - -
  • -

    α-Cadinol, TMS

 - 0.25 - -
Diterpene acids, including: 0.03 (4) 57.52 (16) 64.81 (16) 2.38 (9)
  • -

    Pimaric acid, TMS

 - 1.34 2.20 trace
  • -

    Isopimaric acid, TMS

 trace 4.11 5.79 -
  • -

    Communic acid, TMS

 - 5.32 5.90 -
  • -

    Abietic acid, TMS

 trace 6.43 2.23 0.13
  • -

    Dehydroabietic acid, TMS

 0.01 3.10 8.10 0.08
  • -

    Neoabietic acid, TMS

 - 7.03 1.39 0.07
  • -

    13-epi-Cupresic acid, TMS

 trace 5.75 10.35 -
  • -

    Isocupresic acid, di-TMS

 - 6.67 15.20 -
  • -

    Imbricatoloic acid, di-TMS

 - 4.08 8.48 -
Other diterpenoids, including: - 6.61 (16) 20.36 (22) 0.62 (2)
  • -

    Sandaracopimarinal

 - 0.06 0.09 -
  • -

    13-epi-Manool, TMS

 - 0.22 0.94 -
  • -

    Totarol, TMS

 - 2.83 5.99 trace
  • -

    Ferruginol, TMS

 - 0.90 0.45 -
  • -

    Copalool, TMS

 - 0.15 0.79 -
  • -

    Unidentified diterpenoid, RI 2497

 - 0.65 4.81 -
Triterpenoids, including: 76.93 (29) 12.54 (22) 0.39 (3) 49.91 (32)
  • -

    Cycloartenol, TMS

 7.50 - - 11.54
  • -

    Lupeol, TMS

 9.87 - - 3.444
  • -

    α-Amyrin, TMS

 9.91 0.40 0.07 3.96
  • -

    β-Amyrin, TMS

 8.73 0.69 0.11 5.08
  • -

    Dipterocarpol, TMS

 - - - 1.87
  • -

    Unidentified triterpenoid, RI 3417

 7.50 - - -
  • -

    Unidentified triterpenoid, RI 3645

 2.53 - - 0.71
  • -

    Isomangiferolic acid, di-TMS

 2.41 - - 2.06
  • -

    Mangiferolic acid, di-TMS

 2.46 - - 1.99
  • -

    Mangiferonic acid, TMS

 3.81 - - 5.01
Phenols, including: 1.60 (7) - - 1.03 (6)
  • -

    Hydroginkgol, TMS

 0.07 - - 0.08
  • -

    3-Heptadeca-9,12-dienylphenol, TMS

 0.30 - - 0.55
  • -

    3-Heptadecenylphenol, isomer 1, TMS

 0.07 - - 0.10
  • -

    3-Heptadecenylphenol, isomer 2, TMS

 0.15 - - 0.15
  • -

    3-Heptadecylphenol, TMS

 0.12 - - 0.14
  • -

    3-Heptadecyl-13-hydroxyphenol, di-TMS

 0.84 - - -
Resorcinols, including: 8.16 (10) - - 9.38 (9)
  • -

    5-Pentadecenyl resorcinol, di-TMS

 0.61 - - 0.23
  • -

    5-Pentadecyl resorcinol, di-TMS

 1.00 - - 0.61
  • -

    5-(8,11-Heptadecadienyl) resorcinol, di-TMS

 3.04 - - 4.29
  • -

    5-Heptadecatrienyl resorcinol, di-TMS

 - - - 0.25
  • -

    5-Heptadecenyl resorcinol, isomer 1, di-TMS

 0.51 - - 0.25
  • -

    5-Heptadecenyl resorcinol, isomer 2, di-TMS

 0.60 - - 0.81
  • -

    5-Heptadecenyl resorcinol, isomer 3, di-TMS

 2.32 - - 1.40
  • -

    5-Heptadecyl resorcinol, di-TMS

 - - - 1.14
  • -

    5-Nonadecenyl resorcinol, di-TMS

 0.59 - - -
Salicylates, including: 2.76 (6) - - 4.07 (8)
  • -

    6-Pentadecenyl salicylic acid, di-TMS

 0.06 - - -
  • -

    6-Heptadecadienyl salicylic acid, di-TMS

 0.82 - - 1.63
  • -

    6-Heptadecenyl salicylic acid, isomer 1, di-TMS

 0.25 - - 0.09
  • -

    6-Heptadecenyl salicylic acid, isomer 2, di-TMS

 0.21 - - 0.39
  • -

    6-Heptadecenyl salicylic acid, isomer 3, di-TMS

 0.97 - - 0.61
  • -

    6-Heptadecyl salicylic acid, di-TMS

 - - - 0.61
  • -

    6-(12-Hydroxyheptadecyl) salicylic acid, tri-TMS

 0.45 - - -
Aliphatic alcohols, including: 0.04 (1) 3.32 (4) - 6.73 (7)
  • -

    Octacosanol, TMS

 - 0.22 - -
  • -

    Triacontanol, TMS

 - 1.69 - -
  • -

    Dotriacontanol, TMS

 - 1.22 - 2.68
  • -

    Tetratriacontanol, TMS

 - 0.19 - 3.72
Aliphatic acids, including: 0.39 (10) 0.65 (7) - 1.15 (10)
  • -

    Palmitic acid, TMS

 0.12 0.15 - 0.21
  • -

    Linoleic acid, TMS

 0.04 trace - 0.06
  • -

    Oleic acid, TMS

 0.12 0.21 - 0.22
Aliphatic esters 2.14 (2) 4.57 (7) - 4.56 (6)
  • -

    Triacontyl acetate

 - 1.44 -
  • -

    Dotriacontyl acetate

 - 1.38 -
  • -

    Tetratriacontyl acetate

 - 0.30 3.15
  • -

    Unknown aliphaic acids acetate (2 isomers)

 2.14 - 0.51
Other 0.61 (9) 2.56 (5) 1.05 (1) 11.68 (9)
NN 7.44 (8) 9.48 (31) 9.08 (21) 8.49 (17)

* —not detected; ** the number of peaks in a particular group of components is given in parentheses; *** trace—below 0.01% of TIC.