A Bottom-Up Approach for Data Mining in Bioaromatization of Beers Using Flow-Modulated Comprehensive Two-Dimensional Gas Chromatography/Mass Spectrometry
Abstract
:1. Introduction
2. Materials and Methods
2.1. Samples
2.2. Materials and Extraction Devices
2.3. Solid-Phase Microextraction Method
2.4. Gas Chromatography
2.5. Identification
2.6. Pixel-Based Chemometric Analysis
3. Results and Discussions
3.1. SPME Optimization
3.2. VOC Tracing Using GC×GC
3.3. Chemometrics
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- KIRIN HOLDINGS. Available online: https://www.kirinholdings.co.jp/english/news/2018/1220_01.html (accessed on 2 April 2019).
- Vasconcelos, Y. Inovações cervejeiras. Pesqui. Fapesp 2017, 251, 18–25. [Google Scholar]
- da Silva, G.A.; Augusto, F.; Poppi, R.J. Exploratory analysis of the volatile profile of beers by HS–SPME–GC. Food Chem. 2008, 111, 1057–1063. [Google Scholar]
- Martins, C.; Brandão, T.; Almeida, A.; Rocha, S.M. Insights on beer volatile profile: Optimization of solid-phase microextraction procedure taking advantage of the comprehensive two-dimensional gas chromatography structured separation. J. Sep. Sci. 2015, 38, 2140–2148. [Google Scholar] [PubMed]
- Venturini Filho, W.G. Bebidas alcoólicas: Ciência e Tecnologia, 2nd ed.; Edgard Blücher Ltda.: Sao Paulo, Brazil, 2016. [Google Scholar]
- Vanderhaegen, B.; Neven, H.; Coghe, S.; Verstrepen, K.J.; Verachtert, H.; Derdelinckx, G. Evolution of Chemical and Sensory Properties during Aging of Top-Fermented Beer. J. Agric. Food Chem. 2003, 51, 6782–6790. [Google Scholar] [PubMed]
- Saison, D.; De Schutter, D.P.; Delvaux, F.; Delvaux, F.R. Optimisation of a complete method for the analysis of volatiles involved in the flavour stability of beer by solid-phase microextraction in combination with gas chromatography and mass spectrometry. J. Chromatogr. A 2008, 1190, 342–349. [Google Scholar] [PubMed]
- Rodrigues, J.A.; Barros, A.S.; Carvalho, B.; Brandão, T.; Gil, A.M.; Ferreira, A.C.S. Evaluation of beer deterioration by gas chromatography-mass spectrometry/multivariate analysis: A rapid tool for assessing beer composition. J. Chromatogr. A 2011, 1218, 990–996. [Google Scholar] [PubMed]
- Pizarro, C.; Pérez-del-Notario, N.; González-Sáiz, J.M. Optimisation of a simple and reliable method based on headspace solid-phase microextraction for the determination of volatile phenols in beer. J. Chromatogr. A 2010, 1217, 6013–6021. [Google Scholar]
- Basso, R.F.; Alcarde, A.R.; Portugal, C.B. Could non-Saccharomyces yeasts contribute on innovative brewing fermentations? Food Res. Int. 2016, 86, 112–120. [Google Scholar]
- Arthur, C.; Pawliszyn, J. Solid Phase Microextraction with Thermal Desorption Using Fused Silica Optical Fibers. Anal. Chem. 1990, 62, 2145–2148. [Google Scholar]
- Jeleń, H.H.; Majcher, M.; Dziadas, M. Microextraction techniques in the analysis of food flavor compounds: A review. Anal. Chim. Acta 2012, 738, 13–26. [Google Scholar]
- Lord, H.; Pawliszyn, J. Evolution of solid-phase microextraction technology. J. Chromatogr. A 2000, 885, 153–193. [Google Scholar]
- Kataoka, H.; Lord, H.L.; Pawliszyn, J. Applications of solid-phase microextraction in food analysis. J. Chromatogr. A 2000, 880, 35–62. [Google Scholar] [PubMed]
- Sterckx, F.L.; Saison, D.; Delvaux, F.R. Determination of volatile monophenols in beer using acetylation and headspace solid-phase microextraction in combination with gas chromatography and mass spectrometry. Anal. Chim. Acta 2010, 676, 53–59. [Google Scholar] [PubMed]
- Kobayashi, M.; Shimizu, H.; Shioya, S. Beer Volatile Compounds and Their Application to Low-Malt Beer Fermentation. J. Biosci. Bioeng. 2008, 106, 317–323. [Google Scholar] [PubMed] [Green Version]
- Riu-Aumatell, M.; Miró, P.; Serra-Cayuela, A.; Buxaderas, S.; López-Tamames, E. Assessment of the aroma profiles of low-alcohol beers using HS-SPME–GC-MS. Food Res. Int. 2014, 57, 196–202. [Google Scholar]
- Saison, D.; De Schutter, D.P.; Delvaux, F.; Delvaux, F.R. Determination of carbonyl compounds in beer by derivatisation and headspace solid-phase microextraction in combination with gas chromatography and mass spectrometry. J. Chromatogr. A 2009, 1216, 5061–5068. [Google Scholar] [PubMed]
- Tian, J. Determination of several flavours in beer with headspace sampling-gas chromatography. Food Chem. 2010, 123, 1318–1321. [Google Scholar]
- Leça, J.M.; Pereira, A.C.; Vieira, A.C.; Reis, M.S.; Marques, J.C. Optimal design of experiments applied to headspace solid phase microextraction for the quanti fi cation of vicinal diketones in beer through gas chromatography-mass spectrometric detection. Anal. Chim. Acta 2015, 887, 101–110. [Google Scholar]
- Cajka, T.; Riddellova, K.; Tomaniova, M.; Hajslova, J. Recognition of beer brand based on multivariate analysis of volatile fingerprint. J. Chromatogr. A 2010, 1217, 4195–4203. [Google Scholar]
- Griffith, J.F.; Winniford, W.L.; Sun, K.; Edam, R.; Luong, J.C. A reversed-flow differential flow modulator for comprehensive two-dimensional gas chromatography. J. Chromatogr. A 2012, 1226, 116–123. [Google Scholar]
- Martins, C.; Brandão, T.; Almeida, A.; Rocha, S.M. Unveiling the lager beer volatile terpenic compounds. Food Res. Int. 2018, 114, 199–207. [Google Scholar] [PubMed]
- Callao, M.P.; Ruisánchez, I. An overview of multivariate qualitative methods for food fraud detection. Food Control 2018, 86, 283–293. [Google Scholar]
- Escandar, G.M.; Olivieri, A.C.; Faber, N.M.; Goicoechea, H.C.; Muñoz de la Peña, A.; Poppi, R.J. Second- and third-order multivariate calibration: Data, algorithms and applications. TrAC Trends Anal. Chem. 2007, 26, 752–765. [Google Scholar]
- Olivieri, A.C. Analytical Advantages of Multivariate Data Processing. One, Two, Three, Infinity? Anal. Chem. 2008, 80, 5713–5720. [Google Scholar] [PubMed]
- Meilgaard, M.C. Flavor chemistry in beer: Part I: Flavor interaction between principal volatiles. Master Brew. Assoc. Am. Tech. Q. 1975, 12, 107–117. [Google Scholar]
- Verstrepen, K.J.; Derdelinckx, G.; Dufour, J.-P.; Winderickx, J.; Thevelein, J.M.; Pretorius, I.S.; Delvaux, F.R. Flavor-Active Esters: Adding Fruitiness to Beer. J. Biosci. Bioeng. 2003, 96, 110–118. [Google Scholar]
- Zhu, M.; Cui, Y. Determination of 4-vinylgaiacol and 4-vinylphenol in top-fermented wheat beers by isocratic high performance liquid chromatography with ultraviolet detector. Braz. Arch. Biol. Technol. 2013, 56, 1018–1023. [Google Scholar] [Green Version]
- Kishimoto, T.; Noba, S.; Yako, N.; Kobayashi, M.; Watanabe, T. Simulation of Pilsner-type beer aroma using 76 odor-active compounds. J. Biosci. Bioeng. 2018, 126, 330–338. [Google Scholar]
- Snow, N.H.; Sinex, J.; Danser, M. Multiple Dimensions of Separations: SPME with GC×GC and GC×GC-TOF-MS. Lc Gc Eur. 2010, 23, 260–267. [Google Scholar]
- Crucello, J.; Miron, L.F.O.; Ferreira, V.H.C.; Nan, H.; Marques, M.O.M.; Ritschel, P.S.; Zanus, M.C.; Anderson, J.L.; Poppi, R.J.; Hantao, L.W. Characterization of the aroma profile of novel Brazilian wines by solid-phase microextraction using polymeric ionic liquid sorbent coatings. Anal. Bioanal. Chem. 2018, 410, 4749–4762. [Google Scholar] [Green Version]
- The Good Scents Company. Available online: http://www.thegoodscentscompany.com/ (accessed on 6 August 2019).
- Yeastlab Biotecnologia. Available online: http://yeastlab.com.br/Files/YLB6001%20-%2001.pdf (accessed on 2 April 2019).
- Kumari, S.; Priya, P.; Misra, G.; Yadav, G. Structural and biochemical perspectives in plant isoprenoid biosynthesis. Phytochem. Rev. 2013, 12, 255–291. [Google Scholar]
- King, A.J.; Dickinson, J.R. Biotransformation of hop aroma terpenoids by ale and lager yeasts. FEMS Yeast Res. 2003, 3, 53–62. [Google Scholar] [PubMed]
- Silva, G.C.; Silva, A.A.S.; Silva, L.S.N.; Godoy, R.L.D.O.; Nogueira, L.C.; Quitério, S.L.; Raices, R.S.L. Method development by GC–ECD and HS-SPME–GC–MS for beer volatile analysis. Food Chem. 2015, 167, 71–77. [Google Scholar] [PubMed]
Compound | Formula | CAS | Match | LTPRI | Detection | Template Matching | Odor | Flavor | |||
---|---|---|---|---|---|---|---|---|---|---|---|
Exp | NIST | BR | ENG | BR | ENG | ||||||
isoamyl acetate | C7H14O2 | 123-92-2 | 885 | 841 | 876 | x | x | x | x | sweet, fruity, banana solvent | sweet, fruity, banana-like with a green ripe nuance |
2-methylpropyl isobutyrate | C8H16O2 | 97-85-8 | 832 | 898 | 910 | x | x | - | - | ethereal fruity, tropical fruit, pineapple, banana | fruity, pineapple, tropical fruit, ripe fruit |
pentyl propionate | C8H16O2 | 624-54-4 | 806 | 973 | 969 | - | x | - | - | sweet, fruity, apricot, pineapple | - |
ß-pinene | C10H16 | 127-91-3 | 890 | 989 | 979 | x | x | x | - | dry, woody, resinous pine and hay green | fresh, piney and woody, terpy and resinous with a slight minty, camphoraceous with a spicy nuance |
ß-myrcene | C10H16 | 123-35-3 | 849 | 990 | 991 | - | x | - | - | peppery, terpene spicy, balsam | woody, citrus, fruity with a tropical mango and slight leafy minty nuances |
ethyl hexanoate | C8H16O2 | 123-66-0 | 859 | 1003 | - | x | x | x | - | sweet, fruity, pineapple, waxy, green and banana | sweet, pineapple, fruity, waxy and banana with a green estry nuance |
hexanoic acid | C6H12O2 | 142-62-1 | 873 | 1045 | 990 | x | x | x | - | sour, fatty, sweat and cheese | cheesy, fruity, phenolic fatty goaty |
ß-ocimene | C10H16 | 13877-91-3 | 828 | 1052 | 1037 | - | x | - | - | citrus, tropical green terpene, woody green | green, tropical, woody with floral and vegetable nuances |
ethyl 5-methylhexanoate | C9H18O2 | 10236-10-9 | 857 | 1067 | 1072 | x | x | - | - | - | - |
linalool oxide | C10H18O2 | 5989-33-3 | 843 | 1076 | 1074 | x | x | - | - | earthy floral, sweet woody | - |
hop ether | C10H16O | 19901-95-2 | 869 | 1100 | - | x | x | x | x | - | - |
linalool | C10H18O | 78-70-6 | 899 | 1107 | 1099 | x | x | x | x | citrus, floral woody, green and blueberry | citrus, orange, lemon, floral, waxy, aldehydic and woody |
heptanoic acid | C7H14O2 | 111-14-8 | 834 | 1125 | 1078 | x | x | - | - | rancid, sour, cheesy, sweat | waxy, cheesy, fruity, dirty and fatty |
fenchol | C10H18O | 1632-73-1 | 828 | 1127 | - | x | - | - | - | camphor borneol pine, woody, dry, sweet, lemon | camphoreous cooling medicinal minty, earthy humus |
trans-pinocarveol | C10H16O | 547-61-5 | 864 | 1149 | - | x | x | x | x | warm, woody and balsamic fennel | - |
cis-isocarveol | C10H16O | 22626-43-3 | 821 | 1166 | - | x | x | - | - | - | - |
2,6-dimethyl-1,5,7-octatrien-3-ol | C10H16O | 29414-56-0 | 808 | 1168 | - | - | x | x | x | camphoreous lime | - |
borneol | C10H18O | 507-70-0 | 811 | 1181 | 1167 | x | - | - | - | pine, woody, camphor balsamic | - |
terpinen-4-ol | C10H18O | 562-74-3 | 825 | 1187 | 1177 | x | x | - | - | pepper, woody, earth musty sweet | cooling, woody, earthy, clove spicy with a citrus undernote |
ethyl octanoate | C10H20O2 | 106-32-1 | 911 | 1201 | 1196 | x | x | x | x | fruity, wine, waxy, sweet apricot, banana brandy and pear | sweet, waxy, fruity and pineapple with creamy, fatty, mushroom and cognac notes |
terpineol | C10H18O | 98-55-5 | 857 | 1206 | 1196 | x | x | - | x | pine, terpene, lilac citrus, woody, floral | citrus, woody with a lemon and lime nuance. it has a slight soapy mouth feel |
myrtenol | C10H16O | 515-00-4 | 823 | 1207 | 1195 | - | x | - | - | woody, pine, balsam sweet, mint | cooling, minty, camphoreous, green with a medicinal nuance |
cis-geraniol | C10H18O | 106-25-2 | 833 | 1236 | - | x | x | - | x | sweet, neroli, citrus, magnolia | lemon, bitter, green and fruity with a terpy nuance |
citronellol | C10H20O | 1117-61-9 | 877 | 1238 | - | x | x | x | x | citronella oil, rose leaf and oily petal | - |
ethyl phenylacetate | C10H12O2 | 101-97-3 | 815 | 1252 | 1246 | x | - | x | - | sweet, floral, honey, rose and balsam cocoa | strong sweet rosy honey and balsamic cocoa-like with molasses and yeasty nuances |
octanoic acid | C8H16O2 | 124-07-2 | 911 | 1257 | 1180 | x | x | x | x | fatty, waxy, rancid oily, vegetable cheesy | rancid soapy, cheesy, fatty brandy |
trans-geraniol | C10H18O | 106-24-1 | 930 | 1263 | - | x | x | x | x | sweet, floral, fruity, rose, waxy and citrus | floral, rosy, waxy and perfume with a fruity, peach-like nuance |
2-phenylethyl acetate | C10H12O2 | 103-45-7 | 935 | 1266 | 1255 | x | x | - | x | floral, rose, sweet, honey, fruity tropical | sweet, honey, floral, rosy with a slight green nectar fruity body and mouth feel |
2-isopropenyl-5-methylhex-4-enal | C10H16O | - | 832 | 1280 | - | - | x | - | - | - | - |
3-nonenoic acid, ethyl ester | C11H20O2 | 91213-30-8 | 805 | 1286 | - | x | x | - | - | - | - |
trans-shisool | C10H18O | 22451-48-5 | 885 | 1288 | - | x | x | x | - | - | - |
(Z)-3-decen-1-ol | C10H20O | 10340-22-4 | 807 | 1290 | - | - | x | - | - | - | - |
1,10-decanediol | C10H22O2 | 112-47-0 | 812 | 1290 | - | x | - | - | x | - | - |
methyl 2-nonynoate | C10H16O2 | 111-80-8 | 800 | 1292 | 1311 | - | X | - | x | floral, green, violet leaf, melon and cucumber | green melon, cucumber, violet tropical fruity |
2-dodecanol | C12H26O | 10203-28-8 | 839 | 1312 | - | x | x | - | - | - | - |
isocarveol | C10H16O | 536-59-4 | 879 | 1313 | - | x | x | - | x | green, linalool, terpineol and fatty | sweet, woody, aromatic spicy cardamom and green cumin like with dried orange peel and green waxy floral nuances |
4-vinylguaiacol | C9H10O2 | 7786-61-0 | 902 | 1323 | - | x | - | x | - | dry, woody, fresh amber cedar and roasted peanut | smoky bacon |
(E)-methyl geranate | C11H18O2 | 1189-09-9 | 918 | 1329 | - | x | x | x | x | waxy, green, fruity flower | - |
myrtanyl acetate | C12H20O2 | 29021-36-1 | 808 | 1351 | - | x | - | - | - | - | - |
citronellyl acetate | C12H22O2 | 150-84-5 | 873 | 1353 | - | x | x | x | x | floral green rose, fruity, citrus, woody and tropical fruit | floral, waxy, aldehydic, with green fruity nuances. fruity pear and apple like |
α-ylangene | C15H24 | 14912-44-8 | 812 | 1371 | 1372 | x | - | - | - | - | - |
γ-nonanolactone | C9H16O2 | 104-61-0 | 818 | 1374 | 1363 | - | x | - | - | coconut, creamy, waxy sweet, buttery oily | coconut, creamy, waxy with fatty milky notes |
α-copaene | C15H24 | 3856-25-5 | 861 | 1377 | - | x | - | - | - | woody | - |
ethyl trans-4-decenoate | C12H22O2 | 76649-16-6 | 878 | 1381 | - | x | x | x | - | green, fruity, waxy and cognac | fatty, waxy, green, pineapple and pear nuances |
geranyl acetate | C12H20O2 | 105-87-3 | 836 | 1381 | 1382 | x | x | x | x | floral rose lavender, green and waxy | waxy, green, floral, oily and soapy with citrus and winey, rum nuances |
ethyl 9-decenoate | C12H22O2 | 67233-91-4 | 858 | 1389 | 1387 | x | x | - | x | fruity, fatty | - |
ethyl decanoate | C12H24O2 | 110-38-3 | 910 | 1396 | 1396 | x | - | x | - | sweet, waxy, fruity, apple grape and oily brandy | waxy, fruity, sweet apple |
isopulegol acetate | C12H20O2 | 57576-09-7 | 801 | 1420 | - | - | x | - | - | woody, sweet peppermint, tropical | woody, berry green and camphoreous with a fruity nuance |
bicyclo[4.1.0]heptane, 7-(1-methylethylidene) | C10H16 | 53282-47-6 | 831 | 1420 | - | x | - | - | - | - | - |
isocaryophyllene | C15H24 | 118-65-0 | 890 | 1423 | 1406 | - | x | - | - | woody, spicy | |
caryophyllene | C15H24 | 87-44-5 | 939 | 1423 | 1419 | x | x | x | - | sweet, woody, spice clove dry | spicy, clove, woody, nut skin and powdery peppery |
isogermacrene D | C15H24 | 317819-80-0 | 872 | 1433 | 1448 | x | x | x | - | - | - |
p-mentha-1(7),8(10)-dien-9-ol | C10H16O | 29548-13-8 | 845 | 1440 | - | x | - | - | - | - | - |
perillyl acetate | C12H18O2 | 15111-96-3 | 863 | 1440 | 1436 | x | x | - | x | fruity, woody and raspberry | ionone raspberry |
isoamyl octanoate | C13H26O2 | 2035-99-6 | 812 | 1448 | 1446 | x | - | x | - | sweet, oily, fruity, green soapy, pineapple and coconut | sweet, fruity, waxy, pineapple, fruity and green with coconut and cognac nuances |
α-humulene | C15H24 | 6753-98-6 | 915 | 1460 | - | x | x | x | - | woody | - |
γ-muurolene | C15H24 | 30021-74-0 | 887 | 1478 | - | x | - | x | - | herbal, woody and spice | - |
farnesyl butanoate | C19H32O2 | 51532-27-5 | 811 | 1485 | - | x | - | x | - | - | - |
aromadendrene | C15H24 | 72747-25-2 | 861 | 1496 | - | x | - | x | - | woody | - |
guaia-1(10), 11-diene | C15H24 | - | 875 | 1501 | 1509 | x | - | x | - | - | - |
neryl isobutanoate | C14H24O2 | 2345-24-6 | 840 | 1509 | 1487 | x | - | - | - | sweet, fresh, fruity, raspberry, strawberry, green | juicy and fruity, green, sweet, melon and waxy |
neryl hexanoate | C16H28O2 | 68310-59-8 | 865 | 1510 | - | x | - | x | - | - | - |
γ-amorphene | C15H24 | 6980-46-7 | 903 | 1517 | 1496 | x | - | - | - | - | - |
delta-amorphene | C15H24 | 16729-01-4 | 904 | 1522 | - | x | - | x | - | - | - |
cis-calamenene | C15H22 | 72937-55-4 | 869 | 1527 | 1531 | x | - | x | - | - | - |
cadinadiene-1,4 | C15H24 | 16728-99-7 | 823 | 1537 | 1533 | x | - | - | - | - | - |
α-muurolene | C15H24 | 31983-22-9 | 836 | 1541 | - | x | - | - | - | - | - |
cis-7-hexadecene | C16H32 | 35507-09-6 | 884 | 1590 | 1566 | x | - | - | - | - | - |
caryophyllene oxide | C15H24O | 1139-30-6 | 914 | 1590 | 1581 | x | x | x | - | sweet, fresh, dry, woody and spicy | dry, woody, cedar old, carrot, ambrette amber |
Ethyl dodecanoate | C14H28O2 | 106-33-2 | 862 | 1594 | 1595 | x | - | x | - | sweet, waxy, floral, soapy clean | waxy, soapy and floral with a creamy, dairy and fruity nuance |
bisaboladien-4-ol | C15H26O | - | 800 | 1608 | - | x | x | - | x | - | - |
humulol | C15H26O | 28446-26-6 | 862 | 1613 | - | - | x | - | - | - | |
humulene-1,2-epoxide | C15H24O | 19888-34-7 | 914 | 1619 | - | x | x | - | x | - | - |
epicubenol | C15H26O | 19912-67-5 | 870 | 1624 | 1627 | x | x | - | - | - | - |
cubenol | C15H26O | 21284-22-0 | 878 | 1636 | 1642 | x | x | - | - | spicy, herbal green tea | - |
alloaromadendrene oxide | C15H24O | - | 833 | 1645 | - | x | x | - | x | - | - |
τ-cadinol | C15H26O | - | 902 | 1650 | 1640 | x | x | - | - | - | - |
intermedeol | C15H26O | 6168-59-8 | 800 | 1667 | 1667 | x | x | x | - | - | - |
elemol acetate | C17H28O2 | - | 800 | 1681 | - | x | x | - | - | - | - |
4(15), 5, 10(14)-germacratrien-1-ol | C15H24O | 81968-62-9 | 800 | 1694 | 1695 | x | x | - | x | - | - |
10-heneicosene | C10H16O | 95008-11-0 | 854 | 1792 | - | x | - | - | - | - |
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Paiva, A.C.; Simões Oliveira, D.; Hantao, L.W. A Bottom-Up Approach for Data Mining in Bioaromatization of Beers Using Flow-Modulated Comprehensive Two-Dimensional Gas Chromatography/Mass Spectrometry. Separations 2019, 6, 46. https://doi.org/10.3390/separations6040046
Paiva AC, Simões Oliveira D, Hantao LW. A Bottom-Up Approach for Data Mining in Bioaromatization of Beers Using Flow-Modulated Comprehensive Two-Dimensional Gas Chromatography/Mass Spectrometry. Separations. 2019; 6(4):46. https://doi.org/10.3390/separations6040046
Chicago/Turabian StylePaiva, Andre Cunha, Daniel Simões Oliveira, and Leandro Wang Hantao. 2019. "A Bottom-Up Approach for Data Mining in Bioaromatization of Beers Using Flow-Modulated Comprehensive Two-Dimensional Gas Chromatography/Mass Spectrometry" Separations 6, no. 4: 46. https://doi.org/10.3390/separations6040046