Impacts of Fermentation on the Phenolic Composition, Antioxidant Potential, and Volatile Compounds Profile of Commercially Roasted Coffee Beans
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemical and Reagents
2.2. Sample Preparation
2.3. Extraction of Free and Bound Phenolic Compounds
2.4. Estimation of Phenolic Content and Antioxidant Potentials
2.4.1. Total Phenolic Content (TPC)
2.4.2. Total Flavonoid Content (TFC)
2.4.3. Total Condensed Tannins (TCT)
2.4.4. 2,2-Diphenyl-1-picrylhydrazyl (DPPH) Assay
2.4.5. 2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) Radical Cation-Based Assay
2.4.6. Ferric Reducing Antioxidant Power (FRAP) Assay
2.4.7. Hydroxyl Radical (•OH) Scavenging Activity Assay
2.4.8. Ferrous Ion Chelating Activity Assay
2.4.9. Reducing Power Assay (RPA)
2.5. Liquid Chromatography–Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry (LC-ESI-QTOF-MS/MS)
2.6. Headspace Solid-Phase Microextraction Coupled to Gas Chromatography–Mass Spectrometry (HS-SPME-GC-MS)
2.7. Statistical Analysis
3. Results and Discussion
3.1. Phenolic Content Estimation Assays (TPC, TFC, TCT)
3.2. Antioxidant Activities of Coffee Bean Estimation
3.3. Correlation between Phenolic Compounds and Antioxidant Potential
3.4. LS-ESI-QTOF-MS/MS Characterization of Phenolic Compounds in Roasted Fermented and Unfermented Coffee Beans
3.4.1. Phenolic Acids
Hydroxycinnamic Acids
3.4.2. Lignans and Stilbenes
3.4.3. Flavonoids and Isoflavonoids
3.4.4. Other Polyphenols
3.5. Volatile Compounds in Fermented and Unfermented Coffee Beans
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Fermented Coffee Bean | Unfermented Coffee Bean | |||
---|---|---|---|---|
Geisha | Bourbon | Geisha | Bourbon | |
Free Phenolic | ||||
TPC (mg GAE/g) | 33.52 ± 2.31 a | 29.95 ± 1.75 b | 29.19 ± 0.74 abc | 23.82 ± 0.81 c |
TFC (mg QE/g) | 0.42 ± 0.07 a | 0.35 ± 0.06 ab | 0.35 ± 0.08 ab | 0.25 ± 0.08 b |
TCT (mg CE/g) | 3.49 ± 0.38 a | 3.18 ± 0.23 a | 4.91 ± 0.74 b | 4.45 ± 0.81 b |
DPPH (mg TE/g) | 116.79 ± 0.55 a | 91.34 ± 0.23 b | 32.81 ± 2.97 c | 32.68 ± 3.20 c |
FRAP (mg TE/g) | 110.06 ± 0.55 a | 86.83 ± 1.97 b | 62.39 ± 4.95 c | 30.99 ± 0.16 d |
ABTS (mg TE/g) | 285.45 ± 1.77 a | 266.61 ± 3.84 a | 144.41 ± 1.94 b | 256.27 ± 1.06 ab |
OH-RSA (mg TE/g) | 255.08 ± 3.91 a | 279.66 ± 1.18 a | 230.51 ± 3.35 ab | 196.61 ± 4.82 b |
FICA (mg EE/g) | 0.79 ± 0.13 a | 0.77 ± 0.42 a | 0.68 ± 0.10 ab | 0.63 ± 0.29 b |
RPA (mg TE/g) | 45.37 ± 0.61 ab | 52.95 ± 3.90 a | 29.56 ± 1.47 c | 34.16 ± 0.15 b |
TAC (GAE mg/g) | 6.48 ± 0.28 a | 5.83 ± 0.66 b | 5.89 ± 0.27 ab | 5.20 ± 0.36 b |
Bound Phenolic | ||||
TPC (mg GAE/g) | 7.59 ± 0.12 a | 6.97 ± 0.08 a | 3.14 ± 0.12 b | 2.56 ± 0.15 b |
TFC (mg QE/g) | 0.07 ± 0.01 a | 0.04 ± 0.16 a | - | - |
TCT (mg CE/g) | - | - | - | - |
DPPH (mg TE/g) | 13.30 ± 2.30 a | 9.79 ± 0.70 ab | 0.60 ± 0.86 b | 0.53 ± 0.15 b |
FRAP (mg TE/g) | 12.89 ± 1.23 ab | 20.00 ± 0.78 a | 5.56 ± 0.87 b | 8.08 ± 0.12 b |
ABTS (mg TE/g) | 75.63 ± 1.03 a | 73.62 ± 0.38 a | 41.81 ± 1.13 b | 8.89 ± 3.11 c |
OH-RSA (mg TE/g) | 53.25 ± 1.53 a | 49.15 ± 1.38 ab | 48.31 ± 1.38 ab | 28.25 ± 1.44 b |
FICA (mg EE/g) | 0.79 ± 0.16 ab | 0.97 ± 0.15 a | 0.78 ± 0.06 ab | 0.72 ± 0.20 b |
RPA (mg TE/g) | 8.01 ± 0.83 a | 9.31 ± 0.05 a | 3.59 ± 0.06 b | 2.63 ± 0.54 b |
TAC (GAE mg/g) | 0.99 ± 0.13 a | 0.94 ± 0.02 a | 0.75 ± 0.08 b | 0.81 ± 0.18 ab |
TPC | TFC | TCT | DPPH | FRAP | ABTS·+ | ·OH | FICA | RPA | TAC | |
TPC | 1 | |||||||||
TFC | 0.997 * | 1 | ||||||||
TCT | 0.918 * | 0.900 * | 1 | |||||||
DPPH | 0.859 * | 0.873 * | 0.605 | 1 | ||||||
FRAP | 0.918 * | 0.935 * | 0.702 | 0.966 * | 1 | |||||
ABTS·+ | 0.917 * | 0.900 * | 0.808 | 0.876 * | 0.837 * | 1 | ||||
·OH | 0.986 * | 0.979 * | 0.904 * | 0.856 * | 0.905 * | 0.919 * | 1 | |||
FICA | −0.357 | −0.348 | −0.601 | −0.061 | −0.092 | −0.290 | −0.382 | 1 | ||
RPA | 0.953 * | 0.942 * | 0.820 | 0.908 * | 0.909 * | 0.960 * | 0.975 * | −0.279 | 1 | |
TAC | 0.992 * | 0.985 * | 0.949 * | 0.824 | 0.884 * | 0.910 * | 0.985 * | −0.451 | 0.943 * | 1 |
No. | Proposed Compounds | Molecular Formula | RT (min) | Ionization (ESI+/ESI−) | Molecular Weight | Theoretical (m/z) | Observed (m/z) | Error (ppm) | MS2 Product Ions | Coffee Samples |
---|---|---|---|---|---|---|---|---|---|---|
Phenolic acid | ||||||||||
Hydroxycinnamic acids | ||||||||||
1 | p-Coumaroyl tartaric acid | C13H12O8 | 9.185 | [M−H]- | 296.0541 | 295.0468 | 295.0470 | 0.7 | 115 | FG |
2 | 3-Caffeoylquinic acid | C16H18O9 | 25.788 | ** [M−H]- | 354.0942 | 353.0869 | 353.0871 | 0.6 | 253, 190, 144 | * FB, UFG |
3 | 5-5′-Dehydrodiferulic acid | C20H18O8 | 27.889 | [M+H]+ | 386.0999 | 387.1072 | 387.1073 | 0.3 | 369 | * FB, FG |
Lignans | ||||||||||
4 | Enterolactone | C18H18O4 | 16.535 | [M+H]+ | 298.1192 | 299.1265 | 299.1263 | −0.7 | 281, 187, 165 | FG |
5 | 7-Oxomatairesinol | C20H20O7 | 45.824 | [M+H]+ | 372.122 | 373.1293 | 373.1297 | 1.1 | 358, 343, 328, 325 | FB |
6 | Schisandrol B | C23H28O7 | 89.329 | [M+H]+ | 416.1825 | 417.1898 | 417.1892 | −1.4 | 224, 193, 165 | FB |
7 | Schisantherin A | C30H32O9 | 86.857 | [M+H]+ | 536.2054 | 537.2127 | 537.2130 | 0.6 | 519, 415, 385, 371 | * FG, FB |
Stilbenes | ||||||||||
8 | 4-Hydroxy-3,5,4′-trimethoxystilbene | C17H18O4 | 39.862 | [M+H]+ | 286.1191 | 287.1264 | 287.1264 | 0.0 | 271, 241, 225 | * FB, FG |
Flavonoids | ||||||||||
Flavonols | ||||||||||
9 | Quercetin 3-O-(6″-malonyl-glucoside) | C24H22O15 | 24.64 | [M+H]+ | 550.0956 | 551.1029 | 551.1028 | −0.2 | 303 | * FB, FG |
10 | Prodelphinidin dimer B3 | C30H26O14 | 34.76 | [M+H]+ | 610.1332 | 611.1405 | 611.1394 | −1.8 | 469, 311, 291 | FB |
11 | Quercetin 3-O-xylosyl-rutinoside | C32H38O20 | 40.43 | [M+H]+ | 742.1962 | 743.2035 | 743.2009 | −3.5 | 479, 317 | FG |
Flavones | ||||||||||
12 | Gardenin B | C19H18O7 | 88.235 | [M+H]+ | 358.1066 | 359.1139 | 359.1148 | 2.5 | 344, 329, 311 | FB |
Anthocyanins | ||||||||||
13 | Pelargonidin 3-O-rutinoside | C27H31O14 | 21.545 | [M+H]+ | 579.1701 | 580.1774 | 580.1775 | 0.2 | 271, 433 | * FB, FG |
Isoflavonoids | ||||||||||
14 | 6″-O-Malonylgenistin | C24H22O13 | 4.081 | [M+H]+ | 518.107 | 519.1143 | 519.1118 | −4.8 | 271 | UFG |
15 | 6″-O-Acetylglycitin | C24H24O11 | 10.044 | [M+H]+ | 488.1327 | 489.14 | 489.1397 | −0.6 | 285, 270 | UFG |
Other polyphenols | ||||||||||
Hydroxycoumarins | ||||||||||
16 | Esculin | C15H16O9 | 26.85 | [M+H]+ | 340.0794 | 341.0867 | 341.0855 | −3.5 | 179, 151 | FG |
17 | Coumarin | C9H6O2 | 24.106 | [M+H]+ | 146.0369 | 147.0442 | 147.0442 | 0.0 | 103, 91 | * UFG, FG |
Furanocoumarins | ||||||||||
18 | Isopimpinellin | C13H10O5 | 80.679 | [M+H]+ | 246.0539 | 247.0612 | 247.0611 | −0.4 | 232, 217, 205, 203 | * FG, FB |
No. | Compound Name | Molecular Formula | RT (mins) | Aroma | Content (mg/g) | |||
---|---|---|---|---|---|---|---|---|
Fermented | Unfermented | |||||||
Geisha | Bourbon | Geisha | Bourbon | |||||
Phenols | ||||||||
1 | Phenol | C6H6O | 31.02 | Phenolic/Rubbery | 0.07 ± 0.01 | 0.10 ± 0.03 | 0.05 ± 0.03 | 0.09 ± 0.01 |
2 | 1,6-Octadien-3-ol, 3,7-dimethyl- (linalool) | C10H18O2 | 20.97 | Citrus/Floral/Woody/Green | 0.09 ± 0.03 | 0.05 ± 0.03 | 0.07 ± 0.03 | 0.03 ± 0.01 |
3 | 2,3-Butanediol | C4H10O2 | 21.43 | Fruity/Creamy/Buttery | 0.41 ± 0.09 | 0.23 ± 0.12 | 0.20 ± 0.02 | 0.12 ± 0.19 |
Pyrazines | ||||||||
4 | Pyrazine | C4H4N2 | 11.36 | Nutty/Roasted | 1.25 ± 0.17 | 1.32 ± 0.44 | 1.21 ± 0.06 | 1.11 ± 0.33 |
5 | Pyrazine, 2,5-dimethyl- | C6H8N2 | 14.76 | Nutty/Peanut/Musty/Earthy | 0.10 ± 0.27 | 0.93 ± 0.20 | 0.99 ± 0.36 | 0.64 ± 0.01 |
6 | Pyrazine, 2,3-dimethyl- | C6H8N2 | 15.44 | Butter/Coffee/Caramellic/Roasted | 0.33 ± 0.04 | 0.27 ± 0.03 | 0.25 ± 0.01 | 0.16 ± 0.06 |
7 | Pyrazine, 2-ethyl-5-methyl- | C7H10N2 | 16.75 | Coffee/Roasted/Nutty | 0.42 ± 0.09 | 0.41 ± 0.10 | 0.38 ± 0.15 | 0.28 ± 0.02 |
8 | Pyrazine, 2,6-diethyl- | C8H12ON2 | 17.93 | Nutty/Hazelnut | 0.06 ± 0.01 | 0.06 ± 0.02 | 0.04 ± 0.02 | 0.04 ± 0.01 |
Acid and esters | ||||||||
9 | Acetic acid | C2H4O2 | 18.24 | Sour/Overripe fruit | 9.80 ± 2.61 | 8.31 ± 0.93 | 9.13 ± 0.55 | 7.73 ± 1.00 |
10 | Butanoic acid, 3-methyl- | C5H10O2 | 23.83 | Mentholic/Fruity | 1.18 ± 0.17 | 1.32 ± 0.44 | 1.21 ± 0.06 | 1.34 ± 0.33 |
11 | Propanoic acid | C3H6O2 | 20.61 | Acidic/Cheesy/Vinegar/Oniony | 0.26 ± 0.01 | 0.34 ± 0.03 | 0.35 ± 0.01 | - |
12 | 2-Butenoic acid, 3-methyl- | C5H8O2 | 26.67 | Green/Phenolic/Dairy | 0.28 ± 0.06 | 0.24 ± 0.06 | 0.28 ± 0.02 | 0.32 ± 0.11 |
Furan and Furanic compounds | ||||||||
13 | Furfural | C5H4O2 | 18.56 | Bready/Woody/Baked | 4.57 ± 0.13 | 5.34 ± 0.67 | 4.11 ± 0.92 | 5.25 ± 1.35 |
14 | 2-Furanmethanol | C5H6O2 | 23.62 | Sweet/Caramellic/Bready/Coffee | 5.02 ± 0.37 | 4.97 ± 0.52 | 4.52 ± 0.40 | 4.86 ± 0.92 |
15 | 2-Furancarboxaldehyde, 5-methyl- | C6H6O2 | 21.37 | Caramellic/Spice/Maple/Bready | 2.70 ± 0.41 | 3.28 ± 0.56 | 2.25 ± 0.47 | 3.14 ± 0.93 |
Ketones | ||||||||
16 | Butyrolactone | C4H6O2 | 22.65 | Creamy/Oily/Caramellic | 0.58 ± 0.13 | 0.55 ± 0.04 | 0.50 ± 0.01 | 0.44 ± 0.11 |
17 | 2-Cyclopenten-1-one, 3-ethyl-2-hydroxy- | C7H10O2 | 28.86 | Caramellic/Maple/Brown/Toasted | 0.06 ± 0.01 | 0.06 ± 0.01 | 0.05 ± 0.01 | 0.07 ± 0.01 |
Other compounds | ||||||||
18 | Anethole | C10H12O | 27.41 | Licorice/Anise/Spice/Sweet | 0.95 ± 0.13 | 1.05 ± 0.16 | 0.80 ± 0.10 | 0.99 ± 0.21 |
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Tan, Y.; Wu, H.; Shi, L.; Barrow, C.; Dunshea, F.R.; Suleria, H.A.R. Impacts of Fermentation on the Phenolic Composition, Antioxidant Potential, and Volatile Compounds Profile of Commercially Roasted Coffee Beans. Fermentation 2023, 9, 918. https://doi.org/10.3390/fermentation9100918
Tan Y, Wu H, Shi L, Barrow C, Dunshea FR, Suleria HAR. Impacts of Fermentation on the Phenolic Composition, Antioxidant Potential, and Volatile Compounds Profile of Commercially Roasted Coffee Beans. Fermentation. 2023; 9(10):918. https://doi.org/10.3390/fermentation9100918
Chicago/Turabian StyleTan, Yuanyuan, Hanjing Wu, Linghong Shi, Colin Barrow, Frank R. Dunshea, and Hafiz A. R. Suleria. 2023. "Impacts of Fermentation on the Phenolic Composition, Antioxidant Potential, and Volatile Compounds Profile of Commercially Roasted Coffee Beans" Fermentation 9, no. 10: 918. https://doi.org/10.3390/fermentation9100918