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. 2021 May 29;10(6):1236. doi: 10.3390/foods10061236

Table 2.

List of the most important bioactive compounds detected using mass spectrometry in olive leaves and olive pomace and in olive oil mill wastewater (OOMW).

Name Formula (M) m/z
[M-H]- 		m/z
[M + H]+ 		Ionization Source Leaves Olive Pomace OOMW
10-hydroxy-oleacin C17H20O7 335.114 337.128 APCI, ESI [106] 5 [49]
10-hydroxy-oleuropein C25H32O14 555.172 ESI [100] [127]
10-hydroxyoleuropein aglycone C19H22O9 393.120 395.133 APCI, ESI [106] 5
1-β-D-glucopyranosyl acyclodihydroelenolic acid glycosylate C23H28O16 569.209 ESI [128]
1-β-D-glucopyranosylacyclodihydro elenolic acid (acyclodihydroelenolic acid hexoside) C17H28O11 407.156 409.17 APCI, ESI [106] 5 [128]
2-(2-ethyl-3-hydroxy-6-propionylcyclohexyl) acetic acid glucoside C19H32O9 403.197 ESI [100]
2-hydroxy-oleuropein C25H32O14 555.172 ESI [129]
2-phenethyl-β-primeveroside C19H28O10 415.161 417.175 APCI, ESI [106] 5
3,4-dihydroxyphenylglycol C8H10O4 151.040 d 153.054 a APCI, ESI, MALDI [106] 5 [76] 1
4-hydroxyphenylacetic acid C8H8O3 151.040 153.054 APCI, ESI [106]5 [130]
6′-β-rhamnopyranosyl-oleoside C22H32O15 535.167 ESI [130]
6′-O-[2,6-dimethyl-8-hydroxy-2-octenoyloxy]-secologanoside C26H38O13 557.224 ESI [101]
7-deoxyloganic acid C16H24O9 359.135 ESI [108] [127]
Acteoside C29H36O15 623.198 ESI [103]
Acetoxypinoresinol C22H24O8 415.139 ESI [100] [131]
Aesculetin (Dihydroxhycoumarin isomers) C9H6O4 177.019 179.034 APCI, ESI [106] 5 [108]
Aesculin C15H16O9 339.072 341.088 APCI, ESI [106] 5
Apigenin C15H10O5 269.046 271.06 APCI, ESI [9] 3 [100] [106] 5 [108,109] [96,127,131,132,133] [133]
Apigenin 6,8-di-C-glucoside (Vicenin 2) C27H30O15 593.151 ESI [7]
Apigenin-7-O-glucoside C21H20O10 431.098 433.113 APCI, ESI, FAB [7] [9] 3 [99,100,101,105] [106] 5 [108] [96,127,131,133] [133]
Apigenin-7-O-rutinoside C27H30O14 577.156 579.171 APCI, ESI [7,23,100,101,102] [106] 5 [108] [134]
Ascorbyl hexoside C12H18O11 337.078 ESI [7]
Azelaic acid C9H16O4 187.097 189.113 APCI, ESI [106] 5
β-hydroxy-isoverbascoside C29H36O16 639.193 ESI [7,108] [128,129] [135,136]
β-hydroxyacteoside C29H36O16 639.193 ESI [129]
β-methoxyl-verbascoside C30H38O16 653.209 ESI [108]
Caffeic acid C9H8O4 179.035 181.05 APCI, ESI [103,105] [106] 5 [49,127,131] [134,136]
Caffeic acid derivative C18H18O9 377.089 ESI [103]
Caffeic acid diglycoside C21H30O13 489.161 ESI [108]
Caffeic alcohol derivative C21H30O13 489.161 ESI [103]
Caffeoyl-6′-secologanoside (Cafselogoside) C25H28O14 551.141 553.155 APCI, ESI [106] 5 [49,50,133] [133,134]
Caffeoyl-hexoside C15H18O9 341.088 ESI [49]
Calceolarioside C23H26O11 477.14 ESI [7,108] [49]
Chlorogenic acid (Caffeoyl-quinic acid) C16H18O9 353.088 355.102 ESI [7,105] [49,130] [134]
Chrysoeriol C16H12O6 299.056 301.071 ESI [134]
Chrysoeriol-7-O-glucoside C22H22O11 461.109 463.124 APCI, ESI [7,99,100,102] [106] 5
Cinammic acid C9H8O2 147.045 ESI [127]
Citric acid C6H8O7 191.02 175.024 a APCI, ESI [7] [106] 5
Comselogoside C25H27O13 535.146 537.16 APCI, ESI [106] 5 [49,50,133] [133,134,136]
Cyanidin-3-rutinoside C27H31O15+ 595.166 ESI [95]
D(+)-Erytro-1-(4-hydroxy-3-methoxy)-phenyl-1,2,3-propantriol C10H14O5 213.077 215.091 ESI [50] [134]
Decaffeoyl verbascoside C20H30O12 461.166 ESI [7] [49]
Dehydro ligstroside aglycone C19H20O7 359.114 361.129 APCI, ESI [106] 5
Dehydro oleuropein aglycone C19H20O8 375.109 377.124 APCI, ESI [106] 5
Demethyloleuropein C24H30O13 525.161 ESI [7,99,102,108] [132,133] [133]
Deoxyloganic acid lauryl ester C23H38O5 393.264 ESI [137]
Desoxyelenolic acid C11H14O5 225.077 227.091 APCI, ESI [106] 5
Dihydro-oleuropein C25H36O13 543.208 APCI, ESI [7] [106] 5 [49,127,128,133] [133]
Dihyroxybenzoic acid hexoside C13H16O9 315.072 ESI [7]
Dihyroxybenzoic acid hexoside pentoside C18H24O13 447.114 ESI [7]
Dimethyl oleuropein aglycone C21H26O8 405.156 407.17 APCI, ESI [106] 5
Diosmetin C16H12O6 299.056 301.071 APCI, ESI [98,100] [106] 5 [108] [127]
Diosmetin glucoside C22H22O11 461.109 ESI [108]
Diosmin C28H32O15 607.167 ESI [7,100,108]
Elenolic acid (EA)-methyl ester C12H16O6 255.088 257.102 APCI, ESI [106] 5
Elenolic acid (EA) C11H14O6 241.072 243.086, 225.077 a APCI, ESI, MALDI [76] 1 [106] 5 [49,127,131] [134,136,138]
Elenolic acid (EA) derivative (decarboxylated form of hydroxyelenolic acid) C10H14O5 213.077 197.081 a APCI, ESI, MALDI [106] 5 [132] [76] 1 [138]
Elenolic acid (EA) derivative C10H16O5 215.092 ESI [50,132]
Elenolic acid decarboxymethylated (EDA) C9H12O4 183.066 185.081 APCI, ESI, MALDI [106] 5 [50] [76] 1 [136,138]
Elenolic acid diglucoside C23H33O16 565.177 ESI [101]
Elenolic acid glucoside (Oleoside methyl ester) C17H24O11 403.125 405.139 APCI, ESI, MALDI [7] [76] 1 [99,100,101,102,103] [106] 5 [108] [127,128,130,133] [133,134]
Elenolic acid hexoside derivative C19H26O13 461.13 ESI [7]
Eriodictyol C15H12O6 287.056 ESI [103,105]
Eudesmic acid C10H12O5 211.06 213.076 APCI, ESI [106] 5
Ferulic acid C10H10O4 193.051 195.066 APCI, ESI [103] [106] 5 [109] [49,127]
Feruloyl-hexoside C16H20O9 401.109 ESI [49]
Flavonol diglicoside C27H30O16 609.146 ESI [108]
Fraxamoside C25H30O13 537.161 ESI [7,108]
Fustin C15H12O6 287.056 ESI [103]
Gallic acid C7H6O5 169.014 APCI, ESI [7,105] [106] 5 [109] [127] [138]
Gallocatechin C15H14O7 305.067 APCI, ESI [106] 5 [108]
Gingerol C17H26O4 293.176 295.19 APCI, ESI [106] 5
Gluconic acid C6H11O7 195.051 ESI [101]
Homovanillyl alcohol C9H12O3 167.071 ESI [103]
Hydrogenated EDA C9H14O4 185.082 MALDI [76] 1
Hydrogenated-EA C11H16O6 243.087 ESI [50]
Hydro-oleuropein C25H34O13 541.193 ESI [128]
Hydroxy-oleocanthal C17H20O6 319.119 321.134 APCI, ESI [106] 5
Hydroxy-EA C11H14O7 257.067 259.081 APCI, ESI [106] 5
Hydroxy-EDA C9H12O5 199.062 183.065 a APCI, ESI [106] 5 [49,132] [136]
Hydroxy-oleuropein C25H32O14 555.172 APCI, ESI [7,101,103] [106] 5 [108] [132]
Hydroxy-oleuropein aglycone C22H32O8 423.202 ESI [108]
Hydroxypinoresinol C20H22O7 373.129 375.145 APCI, ESI [106] 5 [127]
Hydroxytyrosol (3,4-DHPEA) C8H10O3 153.056 155.07 APCI, ESI, MALDI [94,97,99,100,101,103] [106] 5 [108,109] [49,50,96,127,131,132,133] [76] 1 [133,134,136,138,139]
Hydroxytyrosol acetate C10H11O4 195.066 ESI [97,101] [131,133] [133]
Hydroxytyrosol diglucoside C20H28O13 475.146 ESI [127]
Hydroxytyrosol glucoside C14H20O8 315.109 317.124 APCI, ESI, MALDI [7,23] [76] 1 [99,102,103,106] 5 [108] [49,127,130,133] [133,134,136]
Hydroxytyrosol rhamnoside C20H34013 481.193 ESI [127]
Hydroxytyrosil acyclodihydroelenolate C19H26O8 381.156 383.17 ESI [134,136]
Isoacetoside C29H36O15 623.198 625.213 ESI [99] [134]
Isoverbascoside C29H36O15 623.198 ESI [7] [135]
Jaspolyoside C42H54O23 925.298 ESI [7,108]
Jaspolyoside derivative C42H54O22 909.303 ESI [108]
Ligstroside C25H32O12 523.128 525.197
507.185 a
542.223 b 		APCI, ESI, FAB [7,23] [93] 4 [98,99,101,102,103] [106] 5 [108] [132,133] [133,134]
Ligstroside aglycone (p-HPEA-EA) C19H22O7 361.129 363.144 APCI, ESI [94,99] [106] 5 [127,128,131,133] [133,134]
Loganic acid C16H24O10 375.130 ESI [7] [127,132]
Loganic acid glucoside C22H33O16 537.183 ESI [7] [49,127]
Loganin (7-epiloganin) C17H26O10 389.145 ESI [7,101,108] [127]
Loganin glucoside C23H38O16 569.209 ESI [127]
Lucidumoside C C27H35O14 583.203 APCI, ESI [101] [106] 5
Luteolin derivative C31H36O13 615.208 ESI [108]
Luteolin C15H10O6 285.041 287.055 APCI, ESI [9] 3 [23,97,99,100,101,102,103,105] [106] 5 [108,109] [96,127,130,131,132,133] [133,134]
Luteolin derivative C31H28O14 623.141 ESI [108]
Luteolin diglucoside C27H30O16 609.146 611.161 APCI, ESI [7,23,100,101,102] [106] 5
Luteolin-4′-O-glucoside C21H20O11 447.093 449.108 APCI, ESI [94,97,101] [106] 5 [130,133] [133,134]
Luteolin-7-O-glucoside C21H20O11 447.093 449.108 APCI, ESI, MALDI [4,7] [9] 3 [76] 1 [94,97,98,101,105] [106] 5 [96,128,130,131,132,133] [133,134]
Luteolin-7-O-rutinoside C27H30O15 593.151 595.166 ESI APCI [7] [9] 3 [101] [130,132] [134]
Luteolin-hexoside C21H20O11 447.093 449.108 APCI, ESI [7,23,99,100,101,102,103] [106] 5 [108] [127,132]
Luteolin-O-rutinoside C27H30O15 593.151 595.166 APCI, ESI [23,100,102] [106] 5 [108] [49,130,133] [133]
Malic acid C4H6O5 133.014 ESI [7]
Maslinic acid C30H48O4 471.348 ESI [108]
Methoxyloleuropein C26H34O14 569.188 ESI [100,102,103,108]
Methoxyloleuroside C26H34O14 569.188 ESI [108]
Methyl oleacein C18H22O6 333.134 317.139 a APCI, ESI [106] 5
Methyl oleuropein aglycone C20H24O8 391.14 393.154 APCI, ESI [106] 5
Monohydrated oleacein (geminal diol) C17H22O7 337.129 MALDI [76] 1
Monohydrated-EDA C9H14O5 201.077 MALDI [76] 1
Naringenin C15H12O5 271.089 273.076 APCI, ESI [106] 5 [132]
Neo-nüzhenide C31H42O18 701.23 ESI, MALDI [76] 1 [108] [128]
Nüzhenide C31H42O17 685.235 687.25 APCI, ESI [99,103] [106] 5 [49,133] [133,134]
Oleacin (3,4-DHPEA-EDA) C17H20O6 319.119 321.133 APCI, ESI, MALDI [106] 5 [108] [127,131,133] [76] 1 [133,134]
Oleanolic acid C30H48O3 455.353 ESI [108]
Olenoside A and B C11H14O5 249.074 c MALDI [140] 1
Oleocanthal (p-HPEA-EDA) C17H20O5 303.124 305.138 APCI, ESI [106] 5 [127,131,133] [133,134]
Oleoside C16H22O11 389.109 391.117 APCI, ESI [7,23,94,99,101,102,103] [106] 5 [108] [49,50,127,130,132,133] [133,134,136]
Oleoside diglucoside C28H42O21 713.215 ESI [50,127]
Oleoside deoxyriboside C20H26O15 505.12 ESI [49,50,127]
Oleoside dimethyl ester C18H26O11 417.14 ESI [127]
Oleoside glucoside (6′-β-glucopyranosyl-oleoside) C22H32O16 551.162 ESI [127,130]
Oleoside methyl ester derivative C18H30O11 421.172 ESI [7]
Oleuricine A (oleuropein glucoside) C31H42O18 701.23 MALDI [76] 1
Oleuricine B (oleuroside glucoside) C31H42O18 701.23 MALDI [76] 1
Oleuropein C25H32O13 539.177 541.193
558.218 b
523.176 a 		APCI, ESI, FAB, MALDI [7,23] [76] 1 [92] 2 [93] 4 [94,97,98,99,100,101,102,103] [106] 5 [108,109] [96,127,128,130,131,132,133] [133,134,136]
Oleuropein aglycone (3,4-DHPEA-EA) C19H22O8 377.124 379.139 APCI, ESI, FAB, MALDI [23] [76] 1 [92] 2 [94,99,102] [106] 5 [108] [49,127,131,133] [76] 1 [133,134]
Oleuropein aglycone derivative C19H20O7 359.117 ESI [128]
Oleuropein aglycone derivative C16H26O10 377.145 ESI [7,100,103] [130] [134,136]
Oleuropein derivative C25H36O12 527.213 ESI [127]
Oleuropein dimer C50H62O25 1075.33 ESI [130]
Oleuropein glucoside isomers C31H42O18 701.23 703.244
720.271 b 		APCI, ESI, FAB [7] [93] 4 [94,99,100,101,102,103] [106] 5 [108] [49,130,133] [133,134]
Oleuropein trimer C75H90O39 1613.499 ESI [130]
Oleuroside C25H32O13 539.177 541.193 ESI [94,98,99,101,102,103,108] [49] [134]
Oxidized isoverbascoside C29H34O15 621.183 ESI [135]
Oxidized verbascoside C29H34O15 621.183 ESI [135]
p-Coumaric acid C9H8O3 163.04 165.055 APCI, ESI [101,105] [106] 5 [49,127,131,133] [133,136]
p-Coumaroyl aldarate C15H16O10 355.067 ESI [49]
p-Coumaroyl hexoside C15H18O8 325.093 ESI [49]
Phenylalanine C9H11NO2 164.072 ESI [127]
p-Hydroxybenzoic acid (4-hydroxybenzoic acid) C7H6O3 137.024 139.038 APCI, ESI [101,103] [106] 5 [138]
Peonidin-3-O-rutinoside C28H33O15+ 609.181 ESI [95]
Pinoresinol C20H22O6 357.134 359.149 APCI, ESI [100,105] [106] 5 [109] [50,127,131,132]
Protocatechuic acid C7H6O4 153.019 155.034 APCI, ESI [105] [106] 5 [127] [138]
Quercetin C15H10O7 301.035 303.05 APCI, ESI [98,99,103,105] [106] 5 [108,109] [127] [134]
Quercetin arabinose C20H18O11 433.078 ESI [128]
Quercetin-4-O-glucoside C21H20O12 463.088 465.101 APCI, ESI [106] 5 [108]
Quercetin-3-O-rhamnoside C21H20O11 447.093 449.108 ESI, MALDI [76] 1 [134]
Quinic acid C7H12O6 191.056 193.071 APCI, ESI [7,100,101] [106] 5 [49,132] [136]
Quinone oxydized hydroxytirosol C8H8O3 151.04 153.054 ESI [132]
Rutin C27H30O16 609.146 611.161 APCI, ESI [7] [9] 3 [23,94,99,100,101,102] [106] 5 [108] [127,130,131,133] [133,134,136]
Secologanic acid C18H26O10 401.145 ESI [127]
Secologanin C17H24O10 387.13 ESI [127]
Secologanoside (oleoside positional isomer) C16H23O11 389.109 APCI, ESI [7,23] [76] 1 [99,100,101,102,103] [106] 5 [108] [127,132,133] [133]
Shikimic acid C7H10O5 173.05 APCI, ESI [127]
Syringaresinol C22H25O8 417.156 419.169 APCI, ESI [99,100] [106] 5
Taxifolin C15H12O7 303.051 305.066 APCI, ESI [7,99,100,103,105] [106] 5 [127]
Tyrosol C8H10O2 137.061 121.064 a APCI, ESI [23] [106] 5 [109] [49,50,127,131,133] [133,136,138,139]
Tyrosol glucoside C14H20O7 299.114 301.13 APCI, ESI [102] [106] 5 [127,133] [133,134]
Vanillic acid C8H8O4 167.035 ESI [105] [127,131,132,133] [133,138]
Vanillic acid hexoside C14H18O9 329.088 ESI [49]
Vanillin C8H8O3 151.04 ESI [7,100,101,103,109] [131]
Verbascoside C29H36O15 623.198 625.213 APCI, ESI [7,23,94,98,101,102,105] [106] 5 [108] [49,96,127,128,130,131,133] [133,134,135,136]

1 MALDI-MS, 2 FAB-MS; 3 APCI-MS; 4 ESI-MS and FAB; 5 ESI-MS and APCI; a [M + H-H2O]+, b [M + NH4]+, c [M + Na]+, d [M + H-H2O].