A Comparative Analysis of the Influence of Human Salivary Enzymes on Odorant Concentration in Three Palm Wines
Abstract
:1. Introduction
2. Results and Discussion
2.1. Potent Wine Odorants
Compound a | Odour-quality b | Retention FFAP | Index SE-54 | FD factor | RW | EW | BW | RWs | EWs | BWs | Previously identified in palm wine c |
---|---|---|---|---|---|---|---|---|---|---|---|
Acetaldehyde | Pungent fruity | nd | 500 | 4 | - | - | + | - | - | + | |
Ethyl acetate | Fruity | 889 | 624 | 8 | - | - | + | - | - | - | |
2-Methyl butanal | Malty | 912 | 663 | 16 | + | + | - | - | - | - | |
3-Methyl butanal | Malty | 927 | 652 | 16 | + | + | + | - | - | - | |
Methyl butanoate | Sweet fruity | 981 | 723 | 16 | - | + | - | - | + | - | |
2,3-Butandione | Buttery | 993 | 592 | 16 | + | + | + | + | + | + | [21,22] |
Ethyl-2-methylbutanoate | Fruity | 1040 | 852 | 16 | + | + | + | + | + | + | |
Ethyl pentanoate | Sweet fruity | 1067 | 900 | 16 | - | + | - | - | + | - | [22] |
2-Heptanone | Soapy fruity | 1181 | 891 | 8 | - | - | + | - | - | + | |
2/3-Methylbutanol | Malty | 1213 | 738 | 64 | + | + | + | + | + | + | |
Ethyl hexanoate | Fruity | 1226 | 1001 | 64 | + | + | + | + | + | + | [21] |
Acetoin | Buttery | 1275 | nd | 256 | + | + | + | + | + | + | |
Ethyl lactate | Phenolic/smoky | 1321 | nd | 8 | + | + | - | - | - | - | |
2-Acetyl-1-pyrroline d | Popcorn | 1323 | 922 | 256 | + | + | + | + | + | + | |
3-Hydroxy-2-butanone | Buttery | nd | 718 | 8 | - | - | + | - | - | + | |
1-Hexanol | Rubbery | 1356 | 872 | 4 | + | + | + | + | + | + | |
Acetic acid | Sweaty | 1428 | 600 | 16 | + | + | + | + | + | + | [21,22] |
Ethyl octanoate | Fruity | 1429 | 1199 | 8 | + | - | - | + | - | - | |
Hexyl-3-methyl butanoate | Fruity | 1430 | nd | 16 | + | + | - | - | - | - | |
2-Ethyl 3,5-dimethylpyrazine | Roasty | 1451 | 1083 | 64 | + | + | - | + | + | + | |
Methional | Cooked potato | 1460 | nd | 8 | + | + | + | + | + | + | [22] |
3-Isobutyl-2-methoxypyrazine | Earthy | 1517 | 1175 | 256 | + | + | + | + | + | + | |
3-Methylbutyl acetate | Banana | 1527 | 878 | 128 | + | + | - | + | + | - | |
2-Acetylpyridine | popcorn | 1532 | nd | 64 | + | + | + | + | + | + | |
Linalool | Fresh-blooming | 1540 | 1103 | 64 | + | + | + | + | + | + | |
2-Methylpropanoic acid | Sweaty | 1563 | nd | 128 | + | + | + | + | + | + | |
Butanoic acid | Sweaty-buttery | 1619 | 821 | 8 | + | + | - | + | + | - | |
2/3-Methylbutanoic acid | Sweaty | 1661 | 875 | 16 | + | + | + | + | + | + | |
(z)-1-5-Octadien-3-one | Geranium-like | 1676 | 984 | 4 | + | + | + | + | + | + | |
( E,E)-2,4-Nonadienal | Fatty | 1718 | 1215 | 8 | - | + | - | - | + | - | |
Pentanoic acid | Sweaty | 1720 | 911 | 16 | + | + | + | + | + | + | |
3-Methylthiol-1,1-propanal | Broth-like | 1723 | 903 | 8 | + | + | - | - | - | - | |
3-Mercapto-2-methylpentanone d | Gravy-meaty | 1742 | 883 | 16 | - | + | - | - | - | - | |
β-Damascenone | Flowery | 1801 | 1389 | 16 | + | + | + | + | + | + | |
2-Methoxyphenol | Smoky | 1842 | 1089 | 64 | + | + | + | + | + | + | |
2-Phenylethanol | Honey | 1911 | 1117 | 128 | + | + | + | + | + | + | |
4-Hydroxy-2,5-dimethyl-3(2H)-furanone | Caramel-like | 2038 | 1070 | 16 | + | + | + | - | - | - | |
3-Methylpentanoic acid | Sweaty | 2040 | nd | 8 | + | + | + | + | + | + | |
Homofuraneol | Apple-like | 2095 | nd | 16 | + | + | - | + | + | - | |
Ethyl cinnamate | Sweet | 2167 | 1469 | 8 | - | + | - | - | - | - | |
Sotolone | Spicy | 2190 | 1110 | 8 | + | + | + | + | + | + | |
Diethyl succinate | Sweet-pineapple | 2390 | nd | 4 | + | + | - | - | - | - | |
y-Dodecalactone | Fruity | 2424 | 1497 | 16 | + | + | + | - | - | - | |
Phenylacetic acid | Honey | 2577 | 1262 | 64 | + | + | + | + | + | + | |
Vanillin | Vanilla | 2601 | 1404 | 16 | + | + | - | - | - | - | |
4-Methoxymethylphenol | Phenolic | 2639 | nd | 8 | - | + | - | - | + | - |
No | Compounds | RW | EW | BW | RWS | EWS | BWS | OAVs (RW) b | OAVs (EW) b | OAVs (BW) b | OTW (µg/L) c |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | 3-Methyl butanol | 19127 ± 25 a | 18300 ± 34 b | 18109 ± 15 c | 19315 ± 12 a | 18360 ± 19 b | 18315 ± 15 b | 19.1 a | 18.3 b | 19.3 a | 1000 |
2 | Ethyl hexanoate | 61.9 ± 3.2 a | 52.2 ± 7.1 b | 48.4 ± 5.2 c | 53.2 ± 6.3 a | 41.5 ± 3.8 b | 39.7 ± 4.6 c | 61.9 a | 52.2 b | 48.4 c | 1 |
3 | Acetoin | 712100 ± 21 a | 663500 ± 15 b | 452120 ± 10 c | 527100 ± 25 a | 410500 ± 14 b | 235600 ± 12 c | 890.13 a | 829.4 b | 565.15 c | 800 |
4 | 2-Acetylpyrroline | 9.8 ± 0.2 b | 11.4 ± 0.1 a | 5.3 ± 0.1 c | 9.6 ± 0.1 b | 11.3 ± 0.2 a | 5.0 ± 0.1 c | 98 b | 114 a | 53c | 0.1 |
5 | 2-Acetylpyridin | 0.32 ± 0.0 b | 0.32 ± 0.0 b | 0.45 ± 0.0 a | 0.30 ± 0.0 b | 0.30 ± 0.0 b | 0.41 ± 0.0 a | nd | nd | nd | nd |
6 | 2-Ethyl-3,5-dimethylpyrazine | 0.25 ± 0.0 b | 0.47 ± 0.0 a | nd | 0.23 ± 0.0 b | 0.46 ± 0.0 a | nd | 1.56 b | 2.9 a | nd | 0.16 |
7 | 3-Isobutyl-2-methoxypyrazine | 10.9 ± 0.0 b | 12.0 ± 0.0 a | 9.7 ± 0.0 c | 11.2 ± 0.0 b | 12.5 ± 0.1 a | 9.9 ± 0.0 c | 2180 b | 2400 a | 1940 c | 0.005 |
8 | 3-Methylbutyl acetate | 70.12 ± 5.2 a | 61.72 ± 3.1 b | nd | 68.50 ± 4.3 a | 59.73 ± 3.0 b | nd | 79.7 a | 70.0 b | nd | 0.88 |
9 | Linalool | 8.74 ± 0.1 c | 11.22 ± 0.1 b | 13.60 ± 0.1 a | 8.72 ± 0.1 c | 11.0 ± 0.1 b | 13.30 ± 1.2 a | 1.46c | 1.9 b | 2.3 a | 6 |
10 | 2-Methylpropanoic acid | 1650 ± 11 b | 1680 ± 9.0 b | 1735 ± 10 a | 1560 ± 8.5 b | 1580 ± 5.0 b | 1640 ± 9.0 a | <1 | <1 | <1 | 8100 |
11 | 2-Methoxy phenol | 0.34 ± 0.0 b | 0.28 ± 0.0 c | 0.40 ± 0.0 a | 0.34 ± 0.0 b | 0.28 ± 0.0 c | 0.40 ± 0.0 a | <1 | <1 | <1 | 3 |
12 | 2-Phenyl ethanol | 6570 ± 10 a | 5880 ± 8.0 b | 4870 ± 10 c | 6120 ± 15 a | 5470 ± 8.2 b | 4380 ± 10 c | 6.57 a | 5.88 b | 4.87 c | 1000 |
13 | Phenylacetic acid | 365 ± 4.5 c | 417 ± 7.0 b | 520 ± 5.0 a | 350 ± 6.0 c | 402 ± 4.1 b | 506 ± 6.0 a | <1 | <1 | <1 | 10000 |
2.2. Influence of Saliva on the Palm Wine Odorants
2.2.1. Pyrazines and Alcohols
2.2.2. Aldehydes and Esters
2.2.3. Thiols
2.3. Odour Activity Values (OAVs)
3. Experimental
3.1. Materials
3.1.1. Raw Materials
3.2. Chemicals
3.3. Stable-Isotope-Labelled Standards
No | Compounds a | Ions ( m/z) | Internal standard | Ion ( m/z) | Calibration factor b |
---|---|---|---|---|---|
1 | 2-Methyl butanol | 71 | [2H3]-2-Methyl butanol | 74 | 0.88 |
2 | 3-Methyl butanol | 71 | [2H3]-2-Methyl butanol | 74 | 0.88 |
3 | Ethyl hexanoate | 145 | [2,2,2,-2H3]-Ethyl hexanoate | 148 | 1.0 |
4 | Acetoin | 91 | 13C2-Acetoin | 93 | 0.89 |
5 | 2-Acetylpyrroline | 60 | [2H3]-Acetylpyrroline | 61 | 1.0 |
6 | Acetic acid | 61 | [13C2]-Acetic acid | 63 | 1.0 |
7 | 2-Ethyl 3,5-dimethylpyrazine | 137 | 2-Ethyl [3,5-2H3] dimethylpyrazine | 140 | 1.0 |
8 | Methional | 105 | 3-([2H3]-Methylthiol)-1-propanal | 108 | 0.71 |
9 | 3-Isobutyl-2-methoxypyrazine | 167 | 3-Isobutyl-2-[2H3]-methoxypyrazine | 170 | 0.95 |
10 | 3-Methylbutyl acetate | 131 | 3-Methyl [3,4-2H3]-methoxypyrazine | 133 | 0.79 |
11 | 2-Acetylpyridine | 53 | 2-[2H3]-Acetylpyridine | 54 | 1.0 |
12 | Linalool | 137 | Tetrahydrolinalool | 141 | 1.61 |
13 | 2-Methoxyphenol | 125 | 2-[2H3]-Methoxyphenol | 128 | 1.0 |
14 | 2-Phenylethanol | 105 | 2-phenyl-[1,1,-2H2] ethanol | 107 | 1.0 |
15 | Phenylacetic acid | 137 | [13C2]-Phenylacetic acid | 139 | 1.0 |
16 | Vanillin | 151 | [2 H3]-Vanillin | 156 | 1.01 |
3.4. Enzymatic Analyses
3.4.1. Collection of Saliva and Enzyme Assay
3.4.2. Interaction of Wine with Saliva
3.4.3. Inhibition of Enzymatic Activity
3.5. Quantitation of the Odorants by Stable Isotope Dilution Assays
3.6. Chromatography-Mass Spectrometry
3.7. Aroma Extracts Dilution Analysis (AEDA)
3.8. Identification of Volatile Compounds
3.9. Calculation of Odour Activity Values (OAVs)
3.10. Statistical Treatment of Data
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Lasekan, O. A Comparative Analysis of the Influence of Human Salivary Enzymes on Odorant Concentration in Three Palm Wines. Molecules 2013, 18, 11809-11823. https://doi.org/10.3390/molecules181011809
Lasekan O. A Comparative Analysis of the Influence of Human Salivary Enzymes on Odorant Concentration in Three Palm Wines. Molecules. 2013; 18(10):11809-11823. https://doi.org/10.3390/molecules181011809
Chicago/Turabian StyleLasekan, Ola. 2013. "A Comparative Analysis of the Influence of Human Salivary Enzymes on Odorant Concentration in Three Palm Wines" Molecules 18, no. 10: 11809-11823. https://doi.org/10.3390/molecules181011809