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Submitted:
19 February 2024
Posted:
21 February 2024
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Variables | Rosemary | coffee | herbal coffee |
TPC mg GAE/g | 54.2 ± 4.8 b | 14.3 ± 2.2 c | 61.5 ± 5.1 a |
TFC mg QE/g | 16.1 ± 1.1 b | 3.2 ± 0.1 c | 19.3 ± 0.9 a |
TCT mg CE/g | 2.3 ± 0.2 b | 3.5 ± 0.3 c | 7.6 ± 0.7 a |
Variables | ABTS mg AAE /g |
FICA mg EDTA/g |
•OH-RSA mg AAE/g |
Alpha-glucosidase inhibition activity IC50 μg/mL |
AChE inhibition activity (IC50 μg/mL) |
Rosemary | 101.8 ± 9.2 b | 1.8 ± 0.4 b | 24.3 ± 1.9 b | 15.9 ± 1.5 b | 17.3 ± 1.9 b |
Coffee | 24.8 ± 2.2 c | 1.3 ± 0.2 c | 8.2 ± 0.5 c | 32.4 ± 2.3 c | 31.1 ± 2.2 c |
Herbal coffee | 126.3 ± 9.5 a | 3.4 ± 0.3 a | 30.1 ± 1.3 a | 12.4 ± 1.2 a | 9.6 ± 0.7 a |
No. | Proposed compounds | Molecular Formula | RT (min) | Mode of ionization | Theoretical (m/z) | Observed (m/z) | Mass Error (ppm) | MS2 product ions |
Phenolic acids | ||||||||
Hydroxybenzoic acids | ||||||||
1 | * Protocatechuic acid | C7H6O4 | 10.346 | [M−H]− | 153.0193 | 153.0197 | 2.6 | 109 |
2 | 4-Hydroxybenzoic acid 4-O-glucoside | C13H16O8 | 17.296 | [M−H]− | 299.0772 | 299.0783 | 4.7 | 255, 137 |
3 | * Syringic acid | C9H10O5 | 22.003 | [M−H]− | 197.0455 | 197.0463 | 3.6 | 182, 153, 138, 123 |
4 | * 2-Hydroxybenzoic acid | C7H6O3 | 28.002 | [M−H]− | 137.0244 | 137.0252 | 5.8 | 93 |
Hydroxycinnamic acids | ||||||||
5 | * 3-Caffeoylquinic acid | C16H18O9 | 8.052 | **[M−H]− | 353.0878 | 353.0878 | 0.0 | 191, 179, 161, 135 |
6 | p-Coumaric acid 4-O-glucoside | C15H18O8 | 10.391 | [M−H]− | 325.0929 | 325.0937 | 2.5 | 163 |
7 | Methyl chlorogenate | C16H18O9 | 12.624 | [M+H]+ | 369.1180 | 369.1193 | 4.9 | 177, 145 |
8 | Dihydroferulic acid | C10H12O4 | 14.611 | [M−H]− | 195.0663 | 195.0664 | 0.5 | 151, 135 |
9 | * Caffeic acid | C9H8O4 | 15.013 | [M−H]− | 179.0350 | 179.0356 | 4.5 | 161, 135 |
10 | 1-Sinapoyl-2-feruloylgentiobiose | C33H40O18 | 15.290 | [M−H]− | 723.2142 | 723.2123 | -3.0 | 529, 449 |
11 | * Rosmarinic acid | C18H16O8 | 15.876 | [M−H]− | 359.0772 | 359.0789 | 4.3 | 197, 179, 161, 135 |
12 | 3-p-Coumaroylquinic acid | C16H18O8 | 17.558 | [M−H]− | 337.0929 | 337.0924 | -1.5 | 191, 173, 93 |
13 | Feruloyl glucose | C16H20O9 | 18.655 | [M−H]− | 355.1034 | 355.103 | -1.1 | 177, 149, 133, 59 |
14 | 1,2-Diferuloylgentiobiose | C32H38O17 | 18.685 | **[M−H]− | 693.2036 | 693.203 | -0.9 | 499, 191 |
15 | 3-Sinapoylquinic acid | C18H22O10 | 18.722 | [M-H]- | 397.114 | 397.1128 | -3.0 | 353, 233, 191 |
16 | 3-Feruloylquinic acid | C17H20O9 | 18.983 | ** [M-H]- | 367.1034 | 367.1034 | 0.0 | 193, 191, 173, 161 |
17 | * Cinnamic acid | C9H8O2 | 19.515 | [M−H]− | 147.0451 | 147.0457 | 4.1 | 103 |
18 | 1,5-Dicaffeoylquinic acid | C25H24O12 | 20.336 | [M−H]− | 515.1195 | 515.1179 | -3.1 | 353, 191, 179, 161 |
19 | 1-O-Sinapoyl-beta-D-glucose | C17H22O10 | 20.384 | [M−H]− | 385.114 | 385.1132 | -2.1 | 367, 223, 205 |
20 | p-Coumaroyl glycolic acid | C11H10O5 | 21.25 | [M−H]− | 221.0455 | 221.0471 | 7.2 | 177, 119, 65 |
21 | * Ferulic acid | C10H10O4 | 22.34 | [M−H]− | 193.0506 | 193.0507 | 0.5 | 178, 149, 134 |
22 | 1-Sinapoyl-2,2’-diferuloylgentiobiose | C43H48O21 | 23.155 | [M−H]− | 899.2615 | 899.2633 | 5.1 | 675, 193 |
23 | 2-Feruloyl-1,2’-disinapoylgentiobiose | C44H50O22 | 23.74 | [M−H]− | 929.2721 | 929.2707 | -1.5 | 223, 205, 193 |
24 | * Sinapic acid | C11H12O5 | 24.43 | [M−H]− | 223.0612 | 223.0607 | -2.2 | 205, 163 |
25 | 1-Caffeoyl-5-feruloylquinic acid | C26H26O12 | 25.86 | [M−H]− | 529.1351 | 529.1324 | -5.1 | 353, 179, 161, 135 |
26 | 1,2,2’-Triferuloylgentiobiose | C42H46O20 | 27.446 | [M−H]− | 869.2509 | 869.25 | -1.0 | 675, 193 |
27 | Cinnamoyl glucose | C15H18O7 | 27.504 | [M−H]− | 309.0979 | 309.0986 | 4.4 | 147, 131, 103 |
28 | * p-Coumaric acid | C9H8O3 | 27.561 | [M−H]− | 163.04 | 163.0396 | -2.5 | 109 |
29 | 3,5-Diferuloylquinic acid | C27H28O12 | 27.896 | [M−H]− | 543.1508 | 543.1495 | -3.2 | 367, 191 |
30 | p-Coumaric acid ethyl ester | C11H12O3 | 28.32 | [M+H]+ | 193.0859 | 193.0859 | 0.0 | 191, 145 |
31 | Verbascoside A | C31H40O16 | 28.517 | [M−H]− | 667.2243 | 667.2261 | 2.7 | 283, 94 |
Flavonoids | ||||||||
Flavanols | ||||||||
32 | 3’-O-Methyl-(-)-epicatechin-7-O-glucuronide | C22H24O12 | 4.94 | [M−H]− | 479.1195 | 479.1194 | -0.2 | 149, 121 |
33 | (+)-Gallocatechin 3-O-gallate | C22H18O11 | 6.905 | [M+H]+ | 459.0922 | 459.0928 | 1.3 | 289 |
34 | * (-)-Epicatechin | C15H14O6 | 9.804 | [M−H]− | 289.0717 | 289.0713 | -1.4 | 245 |
35 | * Procyanidin dimer B2 | C30H26O12 | 23.061 | [M−H]− | 577.1351 | 577.1398 | 8.1 | 451, 425 |
36 | Epicatechin gallate | C22H18O10 | 24.073 | [M−H]− | 441.0827 | 441.0856 | 6.6 | 289 |
37 | Gallocatechin | C15H14O7 | 26.235 | [M−H]− | 305.0667 | 305.0681 | 4.7 | 245 |
38 | 3’-O-Methylepicatechin | C16H16O6 | 28.75 | [M−H]− | 303.0874 | 303.0887 | 5.6 | 271, 163 |
Flavonols | ||||||||
39 | Kaempferol 7-O-glucoside | C21H19O11 | 3.369 | [M−H]− | 446.0854 | 446.0873 | 4.3 | 285 |
40 | Jaceidin 4’-O-glucuronide | C24H24O14 | 4.141 | [M+H]+ | 537.1239 | 537.1257 | 3.4 | 361 |
41 | Myricetin 3-O-rutinoside | C27H30O17 | 4.141 | **[M+H]+ | 627.1556 | 627.1564 | 2.7 | 319 |
42 | Isorhamnetin | C16H12O7 | 4.669 | [M+H]+ | 317.0656 | 317.0673 | 4.6 | 302, 229, 152 |
43 | Myricetin 3-O-rhamnoside | C21H20O12 | 5.787 | [M+H]+ | 465.1028 | 465.1056 | 6.0 | 319, 301 |
44 | Kaempferol-3-O-(2’’-rhamnosyl-galactoside) 7-O-rhamnoside | C33H40O19 | 26.665 | [M−H]− | 739.2091 | 739.2052 | -5.3 | 575, 431, 163 |
45 | Kaempferol | C15H10O6 | 34.542 | [M−H]− | 285.0404 | 285.0423 | 6.5 | 267, 151 |
46 | Quercetin 3-O-(6’’-acetyl-galactoside) 7-O-rhamnoside | C29H32O17 | 59.628 | [M+H]+ | 653.1713 | 653.1731 | 3.3 | 489, 449, 431, 301, 285 |
Flavones | ||||||||
47 | Tricin 7-neohesperidoside | C29H34O16 | 4.715 | [M−H]− | 637.1774 | 637.174 | -5.3 | 491, 329 |
48 | Nobiletin | C21H22O8 | 25.096 | [M−H]− | 401.1242 | 401.1247 | 1.2 | 237, 188, 145, 59 |
49 | Apigenin 6,8-di-C-glucoside | C27H30O15 | 47.368 | [M+H]+ | 595.1658 | 595.171 | 8.7 | 577, 383 |
Flavanones | ||||||||
50 | Didymin | C28H34O14 | 4.306 | [M−H]− | 593.1876 | 593.1865 | -1.9 | 431, 285 |
51 | Hesperetin 3’-O-glucuronide | C22H22O12 | 4.635 | [M+H]+ | 479.1184 | 479.1204 | 4.2 | 303, 285, 177, 151 |
52 | Naringenin 7-O-glucoside | C21H22O10 | 22.752 | [M−H]− | 433.114 | 433.1129 | -2.5 | 271, 151 |
Isoflavonoids | ||||||||
53 | 6’’-O-Malonyldaidzin | C24H22O12 | 3.663 | [M−H]− | 501.1038 | 501.1056 | 3.6 | 253 |
54 | 3’-O-Methylviolanone | C18H18O6 | 4.25 | [M−H]− | 329.1030 | 329.1020 | -3.8 | 285, 163 |
55 | 6’’-O-Acetylglycitin | C24H24O11 | 5.285 | [M−H]− | 487.1246 | 487.1239 | -1.6 | 283, 267, 59 |
56 | 4’-Methoxy-2’,3,7-trihydroxyisoflavanone | C16H14O6 | 6.488 | [M−H]− | 301.0717 | 301.0725 | 2.7 | 177, 135 |
57 | Violanone | C17H16O6 | 8.956 | [M−H]− | 315.0874 | 315.0866 | -3.4 | 300, 285, 135 |
58 | 3’,4’,5,7-Tetrahydroxyisoflavanone | C15H12O6 | 18.008 | [M−H]− | 287.0561 | 287.057 | 3.1 | 269, 179 |
59 | Equol 7-O-glucuronide | C21H22O9 | 21.038 | [M−H]− | 417.1191 | 417.1207 | 3.8 | 399, 241 |
60 | Glycitin | C22H22O10 | 23.403 | [M−H]− | 445.114 | 445.1166 | 5.8 | 427, 311, 267 |
61 | 3’,4’,7-Trihydroxyisoflavanone | C15H12O5 | 23.494 | [M−H]− | 271.0612 | 271.0631 | 7.0 | 163, 135, 109 |
62 | Glycitein 7-O-glucuronide | C22H20O11 | 23.669 | [M−H]− | 459.0933 | 459.0934 | 0.2 | 441, 283, 267 |
63 | Dihydrobiochanin A | C16H14O5 | 27.03 | [M−H]− | 285.0768 | 285.0771 | 1.1 | 269, 203, 175 |
64 | 3’-O-Methylequol | C16H16O4 | 27.479 | [M+H]+ | 273.1122 | 273.112 | -0.7 | 255, 149, 121 |
65 | Daidzin | C21H20O9 | 29.599 | [M−H]− | 415.1034 | 415.1038 | 1.0 | 253 |
66 | Formononetin | C16H14O4 | 34.046 | [M−H]− | 269.0819 | 269.0824 | 1.9 | 251, 223 |
67 | 6’-Hydroxyangolensin | C16H16O5 | 34.255 | [M−H]− | 287.0925 | 287.0917 | -2.8 | 181, 125 |
Dihydroflavonols | ||||||||
68 | Dihydromyricetin 3-O-rhamnoside | C21H22O12 | 4.141 | [M+H]+ | 467.1184 | 467.1215 | 6.6 | 321, 153 |
Dihydrochalcones | ||||||||
69 | 3-Hydroxyphloretin 2’-O-xylosyl-glucoside | C26H32O15 | 12.086 | [M−H]− | 583.1668 | 583.1684 | 2.7 | 565, 289, 271 |
70 | 3-Hydroxyphloretin 2’-O-glucoside | C21H24O11 | 13.591 | [M−H]− | 451.1246 | 451.1252 | 1.3 | 433, 289 |
71 | Phloridzin | C21H24O10 | 25.198 | [M−H]− | 435.1297 | 435.1266 | -7.1 | 273, 255 |
72 | Phloretin 2’-O-xylosyl-glucoside | C26H32O14 | 29.198 | [M−H]− | 567.1719 | 567.1724 | 0.9 | 273, 149 |
Tyrosols | ||||||||
73 | p-HPEA-EDA | C17H20O5 | 4.141 | [M+H]+ | 305.1384 | 305.1378 | -2.0 | 287, 167, 121 |
74 | Hydroxytyrosol | C8H10O3 | 22.684 | [M−H]− | 153.0557 | 153.0555 | -1.3 | 123, 109 |
75 | Hydroxytyrosol 4-O-glucoside | C14H20O8 | 28.715 | ** [M+H]+ | 317.1231 | 317.1228 | -0.9 | 155, 137 |
Phenolic terpenes | ||||||||
76 | Carnosol | C20H26O4 | 32.131 | [M−H]− | 329.1758 | 329.1733 | -7.6 | 285 |
77 | Carnosic acid | C20H28O4 | 40.483 | [M−H]− | 331.1915 | 331.1919 | 1.2 | 287 |
78 | Carvacrol | C10H14O | 49.831 | [M−H]− | 149.0972 | 149.0969 | -2.0 | 133 |
Other polyphenols | ||||||||
79 | Phlorin | C12H16O8 | 4.715 | [M−H]− | 287.0772 | 287.0782 | 3.5 | 125 |
80 | Pyrogallol | C6H6O3 | 9.088 | [M−H]− | 125.0244 | 125.0252 | 6.4 | 107, 97, 79 |
Alkaloids | ||||||||
81 | Trigonelline | C7H7NO2 | 4.116 | [M+H]+ | 138.0549 | 138.0561 | 9.3 | 120, 94, 92 |
82 | Theophylline | C7H8N4O2 | 4.223 | [M−H]− | 179.0574 | 179.0562 | -5.8 | 164, 161, 129, 83 |
83 | ꞵ-Carboline | C11H8N2 | 8.175 | [M+H]+ | 169.0760 | 169.0767 | 5.5 | 142, 117, 115, 70 |
84 | Fontanesine B | C23H19N3O2 | 9.02 | [M+H]+ | 370.1550 | 370.1545 | -2.1 | 208, 147 |
85 | Caffeine | C8H10N4O2 | 16.828 | [M+H]+ | 195.0877 | 195.0887 | 5.3 | 138, 110 |
86 | Vasicine | C11H12N2O | 31.617 | [M+H]+ | 189.1022 | 189.1033 | 5.1 | 171, 161, 147, 121 |
Organic acids | ||||||||
87 | Citric acid | C6H8O7 | 3.769 | [M−H]− | 191.0197 | 191.0196 | -0.5 | 112, 87 |
88 | Quinic Acid | C7H12O6 | 4.173 | [M−H]− | 191.0561 | 191.0561 | 0.0 | 173, 127, 85 |
89 | Fumaric acid | C4H4O4 | 4.515 | [M−H]− | 133.0036 | 115.0033 | -2.6 | 71 |
90 | Mandelic acid | C8H8O3 | 7.156 | [M−H]− | 151.0400 | 151.0412 | 7.9 | 151 |
91 | Malic acid | C4H6O5 | 7.216 | [M−H]− | 133.0142 | 133.0140 | -1.5 | 73 |
Amino acids and hormones | ||||||||
92 | L-Tyrosine | C9H11NO3 | 4.425 | [M+H]+ | 182.0811 | 182.0838 | 17.6 | 167, 165, 136, 124, 122 |
93 | L-Phenylalanine | C9H11NO2 | 4.643 | [M+H]+ | 166.0862 | 166.0880 | 10.8 | 151, 149, 122, 107 |
94 | L-Pyroglutamic acid | C5H7NO3 | 4.751 | [M+H]+ | 130.0498 | 130.0506 | 6.2 | 84 |
95 | Melatonin | C13H16N2O2 | 6.820 | [M+H]+ | 233.1284 | 233.1309 | 10.7 | 185, 152, 93 |
Variables | Before digestion | Gastric digestion | Intestinal stage |
TPC (mg GAE/g) | 61.5 ± 5.1 c | 67.3 ± 6.2 b | 82.2 ± 5.7 a |
TFC (mg QE/g) | 19.3 ± 0.9 a | 13.3 ± 1.1 c | 17.5 ± 1.5 b |
ABTS (mg AAE/g) | 126.3 ± 9.5 b | 124.1 ± 11.2 c | 141.2 ± 12.3 a |
No. | Compounds | Formula | μg/mL | Proposed structure |
1 | Salicylic acid | C7H6O3 | 281.5 ± 14.3 | ![]() |
2 | Cinnamic acid | C9H8O2 | 201.3 ± 11.4 | ![]() |
3 | p-Coumaric acid | C9H8O3 | 29.3 ± 2.6 | ![]() |
4 | 3-p-coumaryolquinic acid | C16H18O8 | 31.4 ± 3.1 | ![]() |
5 | Ferulic acid | C10H10O4 | 142.7 ± 9.8 | ![]() |
6 | 3-Ferulolquinic acid | C17H20O9 | 194.6 ± 12.4 | ![]() |
7 | Chlorogenic acid | C16H18O9 | 18251.5 ± 56.5 | ![]() |
8 | Syringic acid | C9H10O5 | 43.2 ± 4.1 | ![]() |
9 | Caffeic acid | C9H8O4 | 1124.6 ± 11.3 | ![]() |
11 | Protocatechuic acid | C7H6O4 | 45.4 ± 3.9 | ![]() |
12 | Epicatechin | C15H14O6 | 21.4 ± 1.7 | ![]() |
13 | Kaempferol | C15H10O6 | 17.9 ± 1.4 | ![]() |
14 | Procyanidin B2 | C30H26O12 | 11.4 ± 0.7 | ![]() |
15 | Pyrogallol | C6H6O3 | 16.9 ± 0.8 | ![]() |
17 | Carnosol | C20H26O4 | 545.2 ± 22.9 | ![]() |
18 | Quinic acid | C7H12O6 | 1463.6 ± 11.3 | ![]() |
19 | Rosmarinic acid | Rosmarinic acid | 16142.4 ± 89.2 | ![]() |
20 | Carnosic acid | C20H28O4 | 1341.4 ± 12.1 | ![]() |
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