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. 2021 Jan 7;10(1):111. doi: 10.3390/foods10010111

Table 3.

Phenolic compounds characterized in olive leaves (OL), olive mill leaves (OML), exhausted olive pomace (EOP), and residual fraction from olive pit cleaning (RFOPC).

N° RT 1 (Min) Molecular Formula 2 m/z2,3 Error (Ppm) 3 Score 2 MS/MS 1 Compound Class OL OML EOP RFOPC
1 1.2 C14H20O8 315.11 −3.4 94 153, 135, 123 Hydroxytyrosol glucoside Phenylethanoids (not linked to secoiridoids) + − + +
2 1.1 C8H10O3 153.06 1.1 99 123 Hydroxytyrosol Phenylethanoids (not linked to secoiridoids) + + + +
3 1.9 C14H20O7 299.11 0.5 95 179, 161, 119, 101 Tyrosol glucoside Phenylethanoids (not linked to secoiridoids) − − + −
4 7.3 C27H30O15 593.15 −2.8 94 503, 473, 383, 353 Apigenin 6,8-di-C-glucoside Flavones + + − −
5 8.1 C27H30O16 609.15 −3.2 90 447, 285 Luteolin di-hexoxide 1 Flavone + + − −
6 8.4 C25H32O14 555.17 −3.5 91 537, 403, 323, 223 Hydroxyoleuropein 1 Phenylethanoids (linked to secoiridoids) + + − −
7 8.4 C27H30O16 609.15 −2.7 94 447, 285 Luteolin di-hexoside 2 Flavone + + − −
8 8.5 C24H30O13 525.16 −3.4 91 481, 389, 319, 195, 165 Demethyloleuropein Phenylethanoids (linked to secoiridoids) + + − −
9 8.9 C25H32O15 571.17 −3.5 92 523, 403, 359, 223, 179 Dihydroxyoleuropein Phenylethanoids (linked to secoiridoids) + − − −
10 9.2 C27H30O16 609.15 −3.5 91 447, 285 Luteolin di-hexoxide 3 Flavones + + − −
11 9.3 C25H32O14 555.17 −3.1 92 537, 403, 371, 323, 223 Hydroxyoleuropein 2 Phenylethanoids (linked to secoiridoids) + + − −
12 9.3 C23H32O11 483.19 −3.5 93 347, 123 3,4-DHPEA-EDA derivative (+ hexose + H2) Phenylethanoids (linked to secoiridoids) − − + −
13 9.7 C20H32O12 463.18 −3.0 95 347, 301 Quercetin glucoside Flavonols + − + −
14 9.9 C27H30O16 609.15 −3.2 92 447, 301, 179 Quercetin 3-O-rutinoside Flavonols + + + −
15 9.9 C29H36O15 623.20 −3.3 91 461, 315 Verbascoside Caffeoyl phenylethanoid derivatives + + + −
16 10.0 C21H20O11 447.10 −3.7 91 285 Luteolin 7-O-glucoside Flavones + + + −
17 10.2 C27H30O15 593.15 −3.6 90 285 Luteolin hexoside deoxyhexoside 1 Flavones + + + −
18 10.5 C27H30O15 593.15 −3.6 92 447, 285 Luteolin hexoside deoxyhexoside 2 Flavones + + + −
19 10.6 C31H42O18 701.23 −1.9 96 539, 377, 307, 275 Oleuropein hexoside 1 Phenylethanoids (linked to secoiridoids) + + + −
20 10.7 C29H36O15 623.20 −3.7 90 461 Isoverbascoside Caffeoyl phenylethanoid derivatives + + + −
21 10.8 C17H20O7 335.11 −4.0 93 317, 199, 153, 111 Hydroxyde (carboxymethyl) oleuropein aglycone Phenylethanoids (linked to secoiridoids) − − + −
22 11.1 C31H42O18 701.23 −2.4 93 539, 437, 377, 307, 275 Oleuropein hexoside 2 Phenylethanoids (linked to secoiridoids) + + − −
23 11.2 C30H34O11 569.20 −2.6 95 551, 539, 393, 373, 177, 162 G(8-O-4)S(8-5)G 5 (−C) Lignan derivatives − − − +
24 11.3 C27H30O14 557.16 −3.7 90 269 Apigenin 7-O-rutinoside Flavones + + − −
25 11.4 C25H32O13 539.18 −4.6 85 403, 223 Oleouropein 1 Phenylethanoids (linked to secoiridoids) − − + −
26 11.5 C21H20O11 447.09 −3.5 91 285 Luteolin 7-O-hexoside 1 Flavones + + − −
27 11.6 C25H32O13 539.18 −3.1 92 403, 377, 307, 275, 223 Oleuropein Phenylethanoids (linked to secoiridoids) + + + +
28 11.7 C25H28O14 551.14 −3.6 92 507, 389, 341, 281, 251, 179, 161 Caffeoyl-6′-secologanoside Hydroxycinnamics (linked to secoiridoids) − − + −
29 12.0 C22H22O11 461.11 −4.2 90 446, 299, 284 Diosmetin 7-O-glucoside Flavones + + − −
30 12.3 C21H20O11 447.09 −3.5 92 285 Luteolin 7-O-hexoside isomer 2 Flavones + + − −
31 12.4 C25H32O13 539.18 −2.9 92 377, 307, 275, 223 Oleouropein 2 Phenylethanoids (linked to secoiridoids) + + + −
32 12.7 C25H32O13 539.18 −3.5 92 403, 377, 307, 275, 223 Oleouropein 3 Phenylethanoids (linked to secoiridoids) + + + −
33 13.0 C27H36O14 583.20 −2.1 95 537, 403, 223, 179 Lucidumoside C Phenylethanoids (linked to secoiridoids) + + − −
34 13.1 C17H20O6 319.12 −3.6 94 183, 181, 153, 111 3,4-DHPEA-EDA Phenylethanoids (linked to secoiridoids) − − + −
35 13.2 C19H22O8 377.13 −4.3 91 307, 275 Oleuropein aglycone 1 Phenylethanoids (linked to secoiridoids) + − − −
36 13.2 C25H28O13 535.15 −4.0 90 491, 389, 345, 265, 163 p-Coumaroyl-6′-secologanoside Hydroxycinnamics (linked to secoiridoids) − − + +
37 13.5 C25H32O12 523.18 −2.9 94 361, 291, 259, 223 Ligustroside Phenylethanoids (linked to secoiridoids) + + + −
38 14.1 C19H22O8 377.13 −4.0 91 307, 275 Oleuropein aglycone 2 Phenylethanoids (linked to secoiridoids) + − − −
39 14.4 C21H20O6 367.12 −3.7 95 352, 337, 336, 322, 307, 177, 162 S(8-5)G 4 derivative 1 (−H2O) Lignan derivatives − − − +
40 14.6 C20H18O5 337.11 −3.9 93 322, 307, 291, 177, 162 S(8-5)G 4 derivative 2 (−H2O, −CH2O) Lignan derivatives − − − +
41 15.0 C28H34O13 577.19 4.4 92 531, 415, 398, 285, 273, 239 (+)-1-Acetoxypinoresinol 4′-b-O-glucoside Lignan derivatives + − − −
42 15.4 C31H28O14 623.14 −2.2 94 323, 299, 285 Diosmetin di-hexoside Flavones + + − −
43 15.4 C42H54O23 925.30 0.9 97 539, 377, 307, 275 Jaspolyoside isomer 1 Phenylethanoids (linked to secoiridoids) + − − −
44 15.8 C31H36O11 583.22 −3.2 93 565, 535, 413, 387, 373, 357, 343, 195, 165 G(8-O-4)S(8-8)G 5 Lignan derivatives − − − +
45 16.2 C31H34O11 581.20 −2.9 93 563, 551, 533, 503, 385, 367, 355, 337, 336, 218, 195, 177, 165 G(8-O-4)S(8-5)G 4 1 Lignan derivatives − − − +
46 16.4 C41H50O21 877.28 0.2 99 715, 701, 539, 377, 307, 275, 149 Oleuropein derivative 1 (oleuropein hexoside + C10H8O3) Phenylethanoids (linked to secoiridoids) + + − −
47 16.9 C42H54O23 925.30 0.6 96 539, 377, 307, 275 Jaspolyoside isomer 2 Phenylethanoids (linked to secoiridoids) + − − −
48 17.0 C31H34O11 581.20 −2.6 94 551, 367, 355, 337, 218, 195, 165 G(8-O-4)S(8-5)G 4 2 Lignan derivatives − − − +
49 17.0 C34H38O15 685.21 −1.7 92 539, 377, 307, 275 Oleuropein derivative 2 (oleuropein + C9H6O2) Phenylethanoids (linked to secoiridoids) + − − −
50 18.3 C41H58O20 869.34 0.6 95 829, 707, 539, 377, 325, 307, 275, 145 Oleuropein derivative 3 (oleuropein hexoside + C10H16O2) Phenylethanoids (linked to secoiridoids) + − − −
51 18.7 C19H22O7 361.13 −1.6 98 329, 291, 225, 193, 181 Hydroxytyrosol linked to desoxy elenolic acid Phenylethanoids (linked to secoiridoids) − − + −
52 19.3 C35H48O15 707.29 −0.5 97 539, 377, 307, 275 Oleuropein derivative 4 (oleuropein + C10H16O2) Phenylethanoids (linked to secoiridoids) + − − −
53 26.2 C43H60O14 799.39 0.04 99 539, 377, 307, 277 Oleuropein derivative 6 (oleuropein + C18H28O) Phenylethanoids (linked to secoiridoids) + − − −
54 26.8 C41H62O14 777.41 0.23 98 539, 377, 307, 275 Oleuropein derivative 7 (oleuropein + C16H30O) Phenylethanoids (linked to secoiridoids) + − − −
55 14.2 C15H10O6 285.04 −2.12 98 175, 151 Luteolin Flavones − + + −

+ Presence; − absence; bold letter indicates novel compounds. 1 By RP-HPLC-IT-MS. 2 By RP-HPLC-QTOF-MS. 3 [M−H]− ions. 4 G is coniferyl alcohol; S, sinapyl alcohol; G′ is coniferyl aldehyde. The first coniferyl alcohol is hydroxylated (+O). 5 G is coniferyl alcohol; S, sinapyl alcohol. The first coniferyl alcohol is hydroxylated (+O).