Comprehensive Metabolite Fingerprinting of Australian Black and Green Olives and Their Antioxidant and Pharmacokinetics Properties
Abstract
:1. Introduction
2. Materials and Methods
2.1. Reagents and Chemicals
2.2. Preparation and Extraction of Phenolic Compounds
2.3. Measurement of Phenolic Contents and Antioxidant Activities of Olives
2.4. LC–ESI–QTOF–MS/MS Characterization of Metabolites in Olives
2.5. Pharmacokinetic Properties of Metabolites in Olives
2.6. Data Analysis
3. Results and Discussion
3.1. Measurement of Phenolic Content and Antioxidant Activities
3.2. LC-MS/MS Screening and Characterization of Phenolic Compounds
3.2.1. Phenolic Acids
Hydroxybenzoic Acids
Hydroxycinnamic Acids
3.2.2. Flavonoids
Flavanols
Flavonols and Dihydroflavonols
Flavones
Flavanones
3.2.3. Isoflavonoids
3.2.4. Stilbenes and Lignans
3.2.5. Other Compounds
3.3. Pharmacokinetics (ADMET) Properties
3.3.1. Oral Bioavailability
3.3.2. Absorption and Distribution
3.3.3. Metabolism, Excretion, and Toxicity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Variables | Black Olives | Green Olives |
---|---|---|
TPC (mg GAE/g) | 10.94 ± 0.42 | 7.58 ± 0.35 |
TFC (mg QE/g) | 4.94 ± 0.34 | 3.13 ± 0.57 |
TCT (mg CE/g) | 1.11 ± 0.09 | 0.61 ± 0.03 |
DPPH (mg AAE/g) | 19.35 ± 2.83 | 10.71 ± 0.36 |
FRAP (mg AAE/g) | 2.63 ± 0.26 | 3.97 ± 0.61 |
ABTS (mg AAE/g) | 10.35 ± 1.54 | 9.55 ± 0.45 |
FICA (μg EDTA/g) | 1240 ± 31.09 | 750 ± 17.45 |
•OH-RSA (mg AAE/g) | 17.46 ± 0.67 | 9.62 ± 0.46 |
No. | Proposed Compounds | Molecular Formula | RT (min) | Mode of Ionization | Theoretical (m/z) | Observed (m/z) | Mass Error (ppm) | MS/MS Product Ions | Samples |
---|---|---|---|---|---|---|---|---|---|
Phenolic acids | |||||||||
Hydroxybenzoic acids | |||||||||
1 | 3-O-Galloylquinic acid | C14H16O10 | 4.339 | [M + H]+ | 345.0817 | 345.0826 | 2.6 | 327, 283, 153, 125 | BO, GO |
2 | 3-O-Methylgallic acid | C8H8O5 | 6.738 | [M + H]+ | 185.0445 | 185.0456 | 5.9 | 167, 141, 123 | GO, BO |
3 | Protocatechuic acid | C7H6O4 | 12.067 | [M − H]− | 153.0188 | 153.0170 | −1.8 | 109 | BO |
4 | Benzoic acid | C7H6O2 | 16.298 | [M + H]+ | 123.0446 | 123.0449 | 2.4 | 105 | BO, GO |
5 | p-Hydroxybenzoic acid | C7H6O3 | 17.529 | [M − H]− | 137.0239 | 137.0238 | −0.7 | 93 | GO, BO |
6 | Syringic acid | C9H10O5 | 22.488 | [M − H]− | 197.0450 | 197.0455 | 1.6 | 182, 163, 153 | BO, GO |
7 | Ellagic acid | C14H6O8 | 28.754 | [M − H]− | 300.9985 | 300.9951 | −5.3 | 284 | BO |
8 | Paeoniflorin | C23H28O11 | 33.967 | [M − H]− | 479.1554 | 479.1565 | 2.3 | 461, 317 | GO, BO |
Hydroxycinnamic acids | |||||||||
9 | Feruloyl tartaric acid | C14H14O9 | 4.339 | [M + H]+ | 327.0711 | 327.0690 | −6.4 | 309, 177, 163, 151 | GO |
10 | Feruloyl glucose | C16H20O9 | 4.488 | [M + H]+ | 357.1180 | 357.1175 | −1.4 | 195, 177, 149 | GO, BO |
11 | 3-p-Coumaroylquinic acid | C16H18O8 | 4.676 | [M + H]+ | 339.1080 | 339.1087 | 2.1 | 191, 119 | BO |
12 | 3-Sinapoylquinic acid | C18H22O10 | 4.676 | [M + H]+ | 399.1291 | 399.1293 | 0.5 | 223, 191 | BO |
13 | Sinapic acid | C11H12O5 | 10.234 | [M − H]− | 223.0612 | 223.0618 | 2.7 | 193, 179, 149, 134 | BO, GO |
14 | Dihydroferulic acid | C10H12O4 | 13.816 | [M − H]− | 195.0658 | 195.0656 | −1.0 | 177, 151, 135 | BO, GO |
15 | Caffeic acid 4-O-glucoside | C15H18O9 | 14.236 | [M − H]− | 341.0873 | 341.0859 | −4.1 | 179, 135 | GO |
16 | 3-Caffeoylquinic acid | C16H18O9 | 15.157 | [M − H]− | 353.0873 | 353.0875 | 0.6 | 191, 179, 161, 135 | BO, GO |
17 | p-Coumaric acid 4-O-glucoside | C15H18O8 | 16.453 | [M − H]− | 325.0924 | 325.0925 | 0.3 | 163 | GO, BO |
18 | Caffeic acid | C9H8O4 | 18.326 | [M − H]− | 179.0345 | 179.0343 | −1.1 | 135 | GO, BO |
19 | Cinnamic acid | C9H8O2 | 19.374 | [M + H]+ | 149.0602 | 149.0600 | −1.3 | 105 | BO, GO |
20 | 1,2-Disinapoylgentiobiose | C34H42O19 | 20.274 | [M − H]− | 753.2242 | 753.2244 | 0.3 | 529, 223, 205 | GO |
21 | 1-Sinapoyl-2-feruloylgentiobiose | C33H40O18 | 20.527 | [M − H]− | 723.2137 | 723.2103 | −4.7 | 529, 499 | GO, BO |
22 | Verbascoside | C29H36O15 | 20.632 | [M − H]− | 623.1976 | 623.1974 | −0.3 | 461, 161, 133 | BO, GO |
23 | 3,5-Diferuloylquinic acid | C27H28O12 | 21.675 | [M − H]− | 543.1503 | 543.1496 | −1.3 | 193, 191, 134 | GO |
24 | Hydroxycaffeic acid | C9H8O5 | 23.442 | [M − H]− | 195.0294 | 195.0305 | 5.6 | 177, 151 | BO |
25 | Ferulic acid | C10H10O4 | 26.363 | [M − H]− | 193.0501 | 193.0510 | 4.7 | 178, 149, 134 | GO, BO |
26 | Caffeic acid 3-O-glucuronide | C15H16O10 | 29.084 | [M − H]− | 355.0666 | 355.0687 | 5.9 | 179 | BO, GO |
27 | p-Coumaric acid | C9H8O3 | 29.725 | [M − H]− | 163.0395 | 163.0395 | 0.0 | 119 | BO, GO |
Flavonoids | |||||||||
Anthocyanins | |||||||||
28 | Petunidin 3-rhamnoside | C22H23O10 | 9.674 | [M]+ | 447.1291 | 447.1287 | −0.9 | 317 | BO |
29 | Delphinidin | C15H11O7 | 20.848 | [M]+ | 303.0505 | 303.0516 | 3.6 | 303 | BO |
30 | Cyanidin | C15H11O6 | 21.076 | [M]+ | 287.0556 | 287.0576 | 7.0 | 287 | BO |
31 | Cyanidin 3-glucoside | C21H21O11 | 21.662 | [M]+ | 449.1084 | 449.1121 | 8.2 | 287 | BO |
32 | Cyanidin 3-rutinoside | C27H31O15 | 22.092 | [M]+ | 595.1663 | 595.1657 | −0.9 | 287 | BO |
Flavanols | |||||||||
33 | (+)-Gallocatechin | C15H14O7 | 14.021 | [M − H]− | 305.0662 | 305.0671 | 3.0 | 139 | BO, GO |
34 | (+)-Catechin 3-O-gallate | C22H18O10 | 16.159 | [M − H]− | 441.0822 | 441.0844 | 5.0 | 289, 245 | GO |
35 | Prodelphinidin dimer B3 | C30H26O14 | 24.791 | [M − H]− | 609.1245 | 609.1273 | 4.6 | 591, 539 | BO |
36 | (−)-Epicatechin | C15H14O6 | 25.878 | [M − H]− | 289.0712 | 289.0727 | 5.2 | 245, 205 | BO, GO |
Flavonols and dihydroflavonols | |||||||||
37 | 3,7-Dimethylquercetin | C17H14O7 | 16.655 | [M − H]− | 329.0662 | 329.0673 | 3.3 | 301, 283, 165, 121 | GO |
38 | Quercetin 3-rutinoside (Rutin) | C27H30O16 | 20.779 | [M − H]− | 609.1456 | 609.1459 | 0.5 | 301 | BO |
39 | Myricetin 3-O-rhamnoside | C21H20O12 | 21.652 | [M − H]− | 463.0877 | 463.0900 | 5.0 | 317 | BO |
40 | Isorhamnetin 3-O-glucoside 7-O-rhamnoside | C28H32O16 | 21.675 | [M − H]− | 623.1612 | 623.1593 | −3.0 | 315 | GO, BO |
41 | Quercetin 3-O-arabinoside | C20H18O11 | 22.876 | [M − H]− | 433.0771 | 433.0773 | 0.5 | 301 | BO, GO |
42 | Dihydroquercetin (Taxifolin) | C15H12O7 | 23.076 | [M − H]− | 303.0505 | 303.0517 | 4.0 | 217, 125 | BO |
43 | Dihydromyricetin 3-O-rhamnoside | C21H22O12 | 24.626 | [M − H]− | 465.1033 | 465.1035 | 0.4 | 319, 301, 151 | BO |
44 | Myricetin 3-O-rutinoside | C27H30O17 | 26.545 | [M − H]− | 625.1405 | 625.1434 | 4.6 | 317 | GO |
45 | Quercetin | C15H10O7 | 32.243 | [M − H]− | 301.0348 | 301.0355 | 2.3 | 271, 179, 151, 121 | BO |
46 | Isorhamnetin | C16H12O7 | 32.321 | [M − H]− | 315.0505 | 315.0500 | −1.6 | 300, 151, 107 | BO |
47 | Kaempferol 7-O-glucoside | C21H19O11 | 53.800 | [M −H]− | 446.0849 | 446.0854 | 1.1 | 285 | GO |
Flavones | |||||||||
48 | Apigenin 6,8-di-C-glucoside | C27H30O15 | 20.999 | [M − H]− | 593.1507 | 593.1509 | 0.3 | 269 | BO, GO |
49 | Quercetin-3-rhamnoside (Quercitrin) | C21H20O11 | 21.604 | [M − H]− | 447.0928 | 447.0932 | 0.9 | 301 | BO, GO |
50 | 6-Hydroxyluteolin | C15H10O7 | 23.726 | * [M − H]− | 301.0348 | 301.0350 | 0.7 | 283, 257, 175 | BO |
51 | Apigenin 6-C-glucoside | C21H20O10 | 23.340 | [M − H]− | 431.0978 | 431.0981 | 0.7 | 269 | GO, BO |
52 | Luteolin | C15H10O6 | 24.651 | [M − H]− | 285.0399 | 285.0397 | −0.7 | 267, 151, 109 | GO, BO |
53 | Nobiletin | C21H22O8 | 27.296 | [M + H]+ | 403.1393 | 403.1404 | 2.7 | 373, 343, 211 | BO |
54 | Apigenin 7-O-glucoside | C21H24O9 | 28.452 | [M − H]− | 419.1342 | 419.1327 | −3.6 | 269 | GO |
Flavanones | |||||||||
55 | 8-Prenylnaringenin | C20H20O5 | 18.368 | [M + H]+ | 341.1384 | 341.1392 | 2.3 | 323, 221, 147 | GO |
56 | Neoeriocitrin | C27H32O15 | 24.067 | [M − H]− | 595.1663 | 595.1643 | −3.4 | 459, 287, 151 | BO |
57 | Naringin | C27H32O14 | 25.739 | [M − H]− | 579.1714 | 579.1730 | 2.8 | 271 | GO, BO |
58 | Eriodictyol | C15H12O6 | 28.080 | [M − H]− | 287.0556 | 287.0563 | 2.4 | 269, 151 | BO |
59 | Naringenin | C15H12O5 | 30.167 | [M − H]− | 271.0607 | 271.0601 | −2.2 | 253, 229, 151 | BO, GO |
60 | Hesperidin | C28H34O15 | 33.307 | [M − H]− | 609.1820 | 609.1828 | 1.3 | 301 | GO |
61 | Liquiritigenin | C15H12O4 | 37.582 | [M − H]− | 255.0658 | 255.0648 | −3.9 | 237, 135, 93 | BO |
62 | 6-Geranylnaringenin | C25H28O5 | 45.281 | [M − H]− | 407.1859 | 407.1851 | −2.0 | 389, 287, 271 | BO |
Isoflavonoids | |||||||||
63 | Irilone | C16H10O6 | 4.887 | [M + H]+ | 299.0550 | 299.0544 | −2.0 | 299 | GO |
64 | Glycitin | C22H22O10 | 9.674 | [M + H]+ | 447.1291 | 447.1286 | −1.1 | 447 | BO, GO |
65 | 2’-Hydroxyformononetin | C16H12O5 | 11.048 | [M + H]+ | 285.0763 | 285.0762 | −0.4 | 277, 229 | BO |
66 | Daidzin 4’-O-glucuronide | C27H28O15 | 20.192 | [M − H]− | 591.1350 | 591.1375 | 4.2 | 429, 253 | BO |
67 | Dihydroformononetin | C16H14O4 | 23.855 | [M + H]+ | 271.0970 | 271.0958 | −4.4 | 271 | BO |
68 | Puerarin 4’-O-glucoside | C27H30O14 | 25.313 | [M − H]− | 577.1558 | 577.1560 | 0.3 | 415 | GO |
69 | Phloretin | C15H14O5 | 29.324 | [M − H]− | 273.0763 | 273.0763 | 0.0 | 255, 167, 147, 125, 119 | BO |
70 | Sativanone | C17H16O5 | 31.200 | [M − H]− | 299.0920 | 299.0924 | 1.3 | 283, 255, 163 | BO, GO |
71 | 3’-Hydroxymelanettin | C16H12O6 | 32.039 | [M − H]− | 299.0556 | 299.0554 | −0.7 | 284 | BO, GO |
72 | Violanone | C17H16O6 | 34.200 | [M − H]− | 315.0869 | 315.0864 | −1.6 | 297, 163 | BO, GO |
Stilbenes | |||||||||
73 | 3’-Hydroxy-3,4,5,4’-tetramethoxystilbene | C17H18O5 | 30.043 | [M − H]− | 301.1076 | 301.1070 | −2.0 | 283, 255 | BO, GO |
74 | Resveratrol 3-O-glucoside (Polydatin) | C20H22O8 | 32.392 | [M − H]− | 389.1237 | 389.1237 | 0.0 | 227 | BO, GO |
75 | 4’-Hydroxy-3,4,5-trimethoxystilbene | C17H18O4 | 33.113 | [M − H]− | 285.1127 | 285.1118 | −3.2 | 269, 253, 241, 211 | BO, GO |
Lignans | |||||||||
76 | Secoisolariciresinol | C20H26O6 | 24.726 | [M − H]− | 361.1651 | 361.1653 | 0.6 | 343, 331, 315, 165 | BO, GO |
77 | 7-Hydroxymatairesinol | C20H22O7 | 24.825 | [M − H]− | 373.1288 | 373.1281 | −1.9 | 343, 313, 298, 285 | GO |
78 | Lariciresinol | C20H24O6 | 26.023 | [M + H]+ | 361.1651 | 361.1658 | 1.9 | 343, 237, 137 | BO, GO |
79 | Matairesinol | C20H22O6 | 30.607 | [M + H]+ | 359.1494 | 359.1498 | 1.1 | 341, 299, 235, 137 | BO, GO |
80 | Syringaresinol | C22H26O8 | 30.607 | [M + H]+ | 419.1706 | 419.1708 | 0.5 | 419 | BO, GO |
81 | Schisantherin A | C30H32O9 | 30.665 | [M − H]− | 535.1968 | 535.1969 | 0.2 | 535 | GO, BO |
82 | Medioresinol | C21H24O7 | 31.405 | [M + H]+ | 389.1600 | 389.1601 | 0.3 | 389 | BO, GO |
83 | Schisandrol B | C23H28O7 | 35.575 | [M + H]+ | 417.1913 | 417.1916 | 0.7 | 399, 383, 369 | BO |
Other compounds | |||||||||
84 | Quinic Acid | C7H12O6 | 4.218 | [M − H]− | 191.0556 | 191.0566 | 5.2 | 127, 93 | GO, BO |
85 | Melatonin | C13H16N2O2 | 4.281 | [M + H]+ | 233.1284 | 233.1284 | 0.0 | 185, 152, 93 | BO, GO |
86 | Hydroxytyrosol 4-O-glucoside | C14H20O8 | 4.898 | [M − H]− | 315.1080 | 315.1081 | 0.3 | 153 | GO, BO |
87 | Pyrogallol | C6H6O3 | 8.893 | [M + H]+ | 127.0395 | 127.0399 | 3.1 | 107, 97 | BO, GO |
88 | Hydroxytyrosol | C8H10O3 | 10.964 | [M − H]− | 153.0552 | 153.0551 | 0.3 | 123 | BO, GO |
89 | 4-Ethylguaiacol | C9H12O2 | 13.816 | * [M − H]− | 151.0759 | 151.076 | 0.7 | 135, 119, 107 | BO, GO |
90 | Oleoside 11-methylester | C17H24O11 | 14.554 | [M − H]− | 403.1241 | 403.1244 | 0.7 | 223, 165 | BO, GO |
91 | Tyrosol | C8H10O2 | 16.262 | [M − H]− | 137.0603 | 137.0605 | 1.5 | 119, 107, 93 | BO, GO |
92 | 1,3,5-Trimethoxybenzene | C9H12O3 | 17.593 | [M − H]− | 167.0708 | 167.0711 | 1.8 | 137, 121, 111 | BO, GO |
93 | Esculetin | C9H6O4 | 17.873 | [M − H]− | 177.0188 | 177.0197 | 5.1 | 133 | GO, BO |
94 | p-Anisaldehyde | C8H8O2 | 18.326 | [M − H]− | 135.0446 | 135.0447 | 0.7 | 119 | GO, BO |
95 | Umbelliferone | C9H6O3 | 20.622 | * [M − H]− | 161.0239 | 161.0242 | 1.9 | 133, 117 | GO, BO |
96 | Ligstroside | C25H32O12 | 21.295 | [M − H]− | 523.1816 | 523.1816 | 0 | 505, 361, 319, 277 | BO |
97 | Urolithin B | C13H8O3 | 21.798 | [M − H]− | 211.0395 | 211.0398 | 1.4 | 183, 167 | BO, GO |
98 | p-HPEA-AC | C10H12O3 | 22.831 | [M + H]+ | 181.0864 | 181.0859 | −2.8 | 163, 139, 121 | BO, GO |
99 | Oleuropein | C25H32O13 | 23.922 | [M − H]− | 539.1765 | 539.1750 | −2.8 | 521, 377 | BO, GO |
100 | Coumarin | C9H6O2 | 24.189 | [M + H]+ | 147.0446 | 147.0450 | 2.7 | 119, 103 | BO, GO |
101 | 3,4-DHPEA-EDA | C17H20O6 | 24.626 | [M − H]− | 319.1182 | 319.1185 | 0.9 | 275, 195 | BO |
102 | Salvianolic acid G | C20H18O10 | 24.651 | [M − H]− | 417.0822 | 417.0820 | −0.5 | 399, 373, 237, 219 | GO |
103 | Mellein | C10H10O3 | 30.515 | [M − H]− | 177.0552 | 177.0557 | 2.8 | 133, 105 | BO, GO |
104 | Acetyl eugenol | C12H14O3 | 35.444 | [M + H]+ | 207.1021 | 207.1021 | 0.0 | 189, 174, 109 | BO, GO |
105 | Ricinoleic acid | C18H34O3 | 48.542 | [M − H]− | 297.2430 | 297.2439 | 4.9 | 279, 185 | BO, GO |
106 | Corosolic acid | C30H48O4 | 49.217 | [M − H]− | 471.3475 | 471.3475 | 0.0 | 453, 427 | BO, GO |
107 | Carvacrol | C10H14O | 49.840 | [M − H]− | 149.0967 | 149.0967 | 0.0 | 133, 105 | GO, BO |
108 | Kaurenoic acid | C20H30O2 | 50.365 | [M − H]− | 301.2168 | 301.2175 | 2.3 | 283, 255 | BO |
109 | Oleic acid | C18H34O2 | 56.431 | [M − H]− | 281.2481 | 281.2491 | 3.3 | 263, 237, 59 | BO, GO |
110 | Linoleic acid | C18H32O2 | 58.572 | [M − H]− | 279.2324 | 279.2329 | 1.6 | 221, 204, 131, 127 | BO, GO |
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Ali, A.; Ahmadi, F.; Cottrell, J.J.; Dunshea, F.R. Comprehensive Metabolite Fingerprinting of Australian Black and Green Olives and Their Antioxidant and Pharmacokinetics Properties. Separations 2023, 10, 354. https://doi.org/10.3390/separations10060354
Ali A, Ahmadi F, Cottrell JJ, Dunshea FR. Comprehensive Metabolite Fingerprinting of Australian Black and Green Olives and Their Antioxidant and Pharmacokinetics Properties. Separations. 2023; 10(6):354. https://doi.org/10.3390/separations10060354
Chicago/Turabian StyleAli, Akhtar, Farhad Ahmadi, Jeremy J. Cottrell, and Frank R. Dunshea. 2023. "Comprehensive Metabolite Fingerprinting of Australian Black and Green Olives and Their Antioxidant and Pharmacokinetics Properties" Separations 10, no. 6: 354. https://doi.org/10.3390/separations10060354