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. 2022 Feb 16;12:2656. doi: 10.1038/s41598-022-05979-1

Table 1.

LC–ESI/MS data.

Compound RT (min) m/z (+ /− ESI) Exact mass Peak
(a) For ethanolic propolis extracts
C6H6O4 Octane, 3,5-dimethyl- 0.2 142.00 142.20 1 ES + 
C4H6N2O2 1-Methylhydantoin 0.49 114.00 114.10 2 ES + 
C3H4O4 Malonate 0.75 104.10 104.60 3ES + 
C9H11NO3 Alpha-amino-p-hydroxyhydrocinnamic acid 0.75 181.07 181.10 3 ES−
C9H11NO3 Alpha-amino-p-hydroxyhydrocinnamic acid 0.93 179.17 179.07 4 ES + 
C9H8O4 Caffeic acid 1.14 180.13 180.16 5 ES + 
C10H10O4 Ferulic acid 6.10 195.10 194.186 6 ES + 
C15H10O7 Quercetin 7.28 302.102 302.2 7 ES + 
C3H7N3O2 Glycocyamine 7.75 117.024 117.05 8 ES + 
C17H21NO3 Galantamine 7.89 287.10 287.15 9 ES + 
C15H12O5 Kaempferol 7.89 285.13 285.10 9 ES−
C15H10O8 Myricetin 8.08 317.08 316.70 10 ES + 
C15H10O8 Myricetin 8.08 315.10 316.70 10 ES−
C5H9NO3 5-Aminolevulinic acid 8.18 131.014 131.06 11ES + 
C9H8O3 P-Coumaric acid 8.27 164.07 164.047 12ES + 
C15H10O5 Apigenin 8.51 269.074 269.1 13 ES + 
C15H10O5 Apigenin 8.51 269.1 269.1 13 ES−
C15H15NO2S Modafinil 8.76 273.072 273.08 14 ES + 
C15H10O5 Galangin 8.76 271.11 271.1 14 ES−
C14H6O8 Ellagic acid 9.10 302.186 302.199 15ES + 
C11H12O5 3,5-Diphenyl-4 hydroxy cinnamic acid 9.10 299.1 299.105 15ES−
C16H20F3NO3 L-Valine, N-(2-trifluoromethylbenzoyl)-, propyl ester 9.26 331.33 331.11 16 ES + 
C13H16N3O3 2,3 Di-O-acetyl-5-deoxy-S-fluorocytidine 9.20 329.13 329.09 16 ES−
C15H12O5 Kaempferol 9.73 285.10 285.10 17 ES + 
C17H17NO3 Coumaroyl tyramine 9.73 283.1 283.3 17 ES−
C20H17NO3 3,5-Diphenyl-4 hydroxy cinnamic acid 9.95 299.1 299.1 18 ES−
C7H11NO3 N-Tigloylglycine 157.07 157.07 19 ES + 
(b) For ethanolic propolis extract
C18H19NO5 Lycorine-monoacetate 10.41 329.114 329.13 20 ES−
C22H43NO Erucamide 10.68 337.28 337.33 21 ES + 
C18H23O4 5,8-Dihydroxy 9,12-octadecadienoic acid 10.68 313.00 313.23 21ES−
C15H12O4 Pinocembrin 10.93 255.18 256.1 22ES + 
C15H10O4 Chrysin 10.93 253.105 254.057 22ES−
C12H16CINO3 Meclofenoxate 11.22 257.08 257.08 23 ES + 
C15H12O5 Naringenin 11.31 271.1 272.1 24 ES + 
C15H10O5 Naringenin 11.30 270.05 270.11 24 ES−
C17H14O6 Kampferol-dimethyl-ether 11.53 313.11 313.00 25 ES−
C15H14O5 Flavon-3-Ols + 3O 11.60 274.26 274.27 26 ES + 
C15H12O5 Kampferol 11.79 285.10 285.10 27 ES + 
C17H14O4 Chrysin-6-methyl-ether 11.79 283.1 283.00 27 ES−
C12H18N4O4PS Thiamine monophosphate 11.99 345.1 345.08 28 ES + 
C22H33NO5 Fumaric acid, monoamide, N-(3,4-dimethoxyphenethyl)-, 2-ethylhexyl ester 12.20 391.20 391.50 29 ES−
C21H30FN3O2 Pipamperone 12.25 375.15 375.23 30 ES + 
C14H17NO8 P-Acetamidophenylglcuronide 12.32 327.1 327.10 31ES−
C3H7N3O2 Glycocyamine 12.45 117.03 117.05 32ES + 
C19H21NO2 Caffeic acid cinnamylester 12.45 295.16 295.00 32ES−
C22H33NO5 Fumaric acid, monoamide, N-(3,4-dimethoxyphenethyl)-, 2-ethylhexyl ester 12.56 391.16 391.50 33ES + 
C11H19N10S2 2-Hydroxy-3butenyl-glucosinolate 12.56 389.20 389.40 33ES−
C18H19NO5 Lycorine-monoacetate 12.78 329.14 329.13 34ES + 
C14H17NO8 P-Acetamidophenyl-glcuronide 12.78 327.12 327.10 34ES−
C3H7NO3 L-Serine 12.89 105.04 105.04 35ES + 
C13H17NO2 2-Dimethylaminoethyl-cinnamate 13.01 219.20 219.30 36ES + 
C17H14O4 Chrysin-6-methyl-ether 13.30 283.10 283.00 37ES + 
C21H30FN3O2 Pipamperone 13.30 375.21 375.23 37ES−
C3H7N3O2 Glycocyamine 13.69 117.03 117.05 38 ES + 
C15H10O5 Apigenin 13.96 269.2 269.10 39ES + 
C20H23NO4 Coumarin 13.96 341.16 341.16 39 ES−
C15H10O6 Luteolin 14.26 285.06 286.00 40ES + 
C16H18O9 Chlorogenic acid 14.26 355.20 354.095 40 ES−
(c) For BV
C4H6N2O2 1- Methylhydantion 0.25 113.92 113.92 1 ES−
C17H32O2 7-Hexadecenoic acid, methyl ester 0.78 268.40 268.83 2 ES + 
C131H229N39O31 Melittin 2.80 570.28 570.28 3 ES + 
C15H24O2 Curcumol 3.90 236.35 236.20 4 ES + 
C13H21N3O Procainamide 4.47 235.325 235.327 5 ES + 
C13H21N3O Procainamide 4.54 235.325 235.33 6 ES + 
C14H21NO2 Isonicotinic acid, octyl ester 4.61 235.322 235.317 7 ES + 
C12H10FNOS Acetamide, N-(4-fluorophenyl)-2-(2-thienyl)- 4.73 235.277 235.276 8 ES + 
C8H9NO2 Phenol, 4-methyl-2-nitro- 6.78 153.14 153.05 9 ES + 
C15H14O5 Phenol, 2,6-dimethyl-4-nitroso- 6.79 151.16 151.04 9 ES−
C15H10O4 Genistein 6.93 269.074 269.15 10 ES + 
C79H131N31O24S4 Apamin 8.91 507.62 507.62 11 ES + 
C12H22N2O5 Sarcosylsarcosine, n-propoxycarbonyl-, ethyl ester 11.60 274. 31 274.29 12 ES + 
C11H9NO4 Acetoxyacetic acid, 4-cyanophenyl ester 13.01 219.194 219.197 13 ES + 
C14H19NO4 l-Valine, N-(m-anisoyl)-, methyl ester 14.16 265.31 265.212 14 ES−
C13H9N3S Isothiocyanic acid, (p-phenylazo) phenyl ester 20.89 239.30 239.23 15 ES + 
C15H22F5NO3 l-Proline, n-pentafluoropropionyl-, heptyl ester 23.75 359.33 359.36 16 ES + 
C15H10O5 Apigenin 27.65 117.00 116.92 17 ES−
C5H11NO2 Valine 27.98 117.15 116.94 18 ES−
C5H10O2 Butanoic acid, 2-methyl- 31.12 102.13 102.08 19 ES + 
C6H14O2 3-Methylpentane-2,3-diol 31.12 117.916 118.17 20 ES−
C6H6FN 2-Fluoro-6 methylpyridine 31.25 111.12 111.104 21 ES +