Principal Component Analysis of Hop-Derived Odorants Identified by Stir Bar Sorptive Extraction Method

Literature cited

• The International Hop Growers’ Convention (IHGC). IHGC Hop Variety List, 2017. http://www.hmelj-giz.si/ihgc/obj.htm.
   Google Scholar
• Kishimoto, T.; Wanikawa, A.; Kono, K.; Shibata, K. Comparison of the Odor-Active Compounds in Unhopped Beer and Beers Hopped with Different Hop Varieties. J. Agric. Food Chem. 2006, 54, 8855–8861. DOI: 10.1021/jf061342c.
   PubMed Web of Science ®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. DOI: 10.1016/S1567-1356(02)00141-1.
   PubMed Web of Science ®Google Scholar
• Peacock, V. E.; Deinzer, M. L.; McGill, L. A.; Wrolstad, R. E. Hop Aroma in American Beer. J. Agric. Food Chem. 1980, 28, 774–777. DOI: 10.1021/jf60230a025.
   Web of Science ®Google Scholar
• Dresel, M.; Praet, T.; Van Opstaele, F.; Van Holle, A.; Naudts, D.; De Keukeleire, D.; De Cooman, L.; Aerts, G. Comparison of the Analytical Profiles of Volatiles in Single-Hopped Worts and Beers as a Function of the Hop Variety. Brew. Sci. 2015, 68, 8–28.
   Web of Science ®Google Scholar
• Dresel, M.; Van Opstaele, F.; Praet, T.; Jaskula-Goiris, B.; Van Holle, A.; Naudts, D.; De Keukeleire, D.; De Cooman, L.; Aerts, G. Investigation of the Impact of the Hop Variety and the Hopping Technology on the Analytical Volatile Profile of Single-Hopped Worts and Beers. Brew. Sci. 2013, 66, 162–175.
   Google Scholar
• Eyres, G. T.; Marriott, P. J.; Dufour, J. P. Comparison of Odor-Active Compounds in the Spicy Fraction of Hop (Humulus lupulus L.) Essential Oil from Four Different Varieties. J. Agric. Food Chem. 2007, 55, 6252–6261. DOI: 10.1021/jf070739t.
   PubMed Web of Science ®Google Scholar
• Tressl, R.; Friese, L.; Fendesack, F.; Koeppler, H. Gas Chromatography-Mass Spectrometric Investigation of Hop Aroma Constituents in Beer. J. Agric. Food Chem. 1978, 26, 1422–1426. DOI: 10.1021/jf60220a037.
   Web of Science ®Google Scholar
• Forster, A.; Gahr, A. On the Fate of Certain Hop Substances during Dry Hopping. Brew. Sci. 2013, 66, 93–103.
   Google Scholar
• Forster, A.; Gahr, A.; Van Opstaele, F. On the Transfer Rate of Geraniol with Dry Hopping. Brew. Sci. 2014, 67, 60–62.
   Google Scholar
• Hao, J.; Dong, J.; Yin, H.; Yan, P.; Ting, P. L.; Li, Q.; Tao, X.; Yu, J.; Chen, H.; Li, M. Optimum Method of Analyzing Hop Derived Aroma Compounds in Beer by Headspace Solid-Phase Microextraction (SPME) with GC/MS and Their Evolutions during Chinese Lager Brewing Process. J. Am. Soc. Brew. Chem. 2014, 72, 261–270. DOI: 10.1094/ASBCJ-2014-1021-01.
   Web of Science ®Google Scholar
• Inui, T.; Tsuchiya, F.; Ishimaru, M.; Oka, K.; Komura, H. Different Beers with Different Hops. Relevant Compounds for Their Aroma Characteristics. J. Agric. Food Chem. 2013, 61, 4758–4764. DOI: 10.1021/jf3053737.
   PubMed Web of Science ®Google Scholar
• Cibaka, M. L. K.; Ferreira, C. S.; Decourrière, L.; Lorenzo-Alonso, C. J.; Bodart, E.;.; Collin, S. Dry Hopping with the Dual-Purpose Varieties Amarillo, Citra, Hallertau Blanc, Mosaic, and Sorachi Ace: minor Contribution of Hop Terpenol Glucoside to Beer Flavor. J. Am. Soc. Brew. Chem. 2017, 75, 122–129.
   Web of Science ®Google Scholar
• Lam, K. C.; Foster, R. T.; Deinzer, M. L. Aging of Hops and Their Contribution to Beer Flavor. J. Agric. Food Chem. 1986, 34, 763–770. DOI: 10.1021/jf00070a043.
   Web of Science ®Google Scholar
• Lutz, A.; Kammhuber, K.; Seigner, E. New Trend in Hop Breeding at the Hop Research Center Huell. Brew. Sci. 2012, 65, 24–32.
   Google Scholar
• Peacock, V. E.; Deinzer, M. L.; Likens, S. T.; Nickerson, G. B.; McGill, L. A. Floral Hop Aroma in Beer. J. Agric. Food Chem. 1981, 29, 1265–1269. DOI: 10.1021/jf00108a041.
   Web of Science ®Google Scholar
• Schmidt, C.; Biendl, M. Headspace Trap GC-MS Analysis of Hop Aroma Compounds in Beer. Brew. Sci 2016, 69, 9–15.
   Web of Science ®Google Scholar
• Seaton, J. C. The Refinement of Hop Flavor by Yeast Action. Proc. 17th Convent. Inst. Australia New Zealand Sec. 1982, 117–124.
   Google Scholar
• Sharp, D. C.; Townsend, M. S.; Qian, Y.; Shellhammer, T. H. Effect of Harvest Maturity on the Chemical Composition of Cascade and Willamette Hops. J. Am. Soc. Brew. Chem. 2014, 72, 231–238. DOI: 10.1094/ASBCJ-2014-1002-01.
   Web of Science ®Google Scholar
• Sharp, D. C.; Steensels, J.; Shellhammer, T. H. The Effect of Hopping Regime, Cultivar and β-Glucosidase Activity on Monoterpene Alcohol Concentrations in Wort and Beer. J. Inst. Brew. 2017, 123, 185–191. DOI: 10.1002/jib.418.
   Web of Science ®Google Scholar
• Sharp, D. C.; Vollmer, D. M.; Qian, Y.; Shellhammer, T. H. Examination of Glycoside Hydrolysis Methods for the Determination of Terpenyl Glycoside Contents of Different Hop Cultivars. J. Am. Soc. Brew. Chem. 2017, 75, 101–108. DOI: 10.1094/ASBCJ-2017-2071-01.
   Web of Science ®Google Scholar
• Steinhaus, M.; Schieberle, P. Transfer of the Potent Hop Odorants Linalool, Geraniol and 4-Methyl-4-Sulfanyl-2-Pentanone from Hops into Beer. Proc. Eur. Brew. Conv. Congr. Venice., Fachverlag Hans Carl: Nürnberg, Germany, pp 1004–10112007.
   Google Scholar
• Steinhaus, M.; Wilhelm, W.; Schieberle, P. Comparison of the Most Odour-Active Volatiles in Different Hop Varieties by Application of a Comparative Aroma Extract Dilution Analysis. Eur. Food Res. Technol. 2007, 226, 45–55. DOI: 10.1007/s00217-006-0507-6.
   Web of Science ®Google Scholar
• Steyer, D.; Clayeux, C.; Laugel, B. Characterization of the Terpenoids Composition of Beers Made with the French Hop Varieties: Strisselspalt, Aramis, Triskel and Bouclier. Brew. Sci. 2013, 66, 192–197.
   Google Scholar
• Sharp, D. C.; Qian, Y. P.; Shellhammer, G.; Shellhammer, T. H. Contributions of Select Hopping Regimes to the Terpenoid Content and Hop Aroma Profile of Ale and Lager Beers. J. Am. Soc. Brew. Chem. 2017, 75, 93–100. DOI: 10.1094/ASBCJ-2017-2144-01.
   Web of Science ®Google Scholar
• Sharp, D. C.; Qian, Y. P.; Clawson, J. C.; Shellhammer, T. H. An Exploratory Study toward Describing Hop Aroma in Beer Made with American and European Hop Cultivars. Brew. Sci. 2016, 69, 112–122.
   Web of Science ®Google Scholar
• Takoi, K.; Itoga, Y.; Koie, K.; Takayanagi, J.; Kaneko, T.; Watanabe, T.; Matsumoto, I.; Nomura, M. Systematic Analysis of Behavior of Hop-Derived Monoterpene Alcohols during Fermentation and New Classification of Geraniol-Rich Flavor Hops. Brew. Sci. 2017, 70, 177–186.
   Web of Science ®Google Scholar
• Takoi, K.; Itoga, Y.; Koie, K.; Kosugi, T.; Shimase, M.; Katayama, K.; Nakayama, Y.; Watari, J. Contribution of Geraniol Metabolism to Citrus Flavour of Beer: Synergy of Geraniol and β-Citronellol under Coexistence with Excess Linalool. J. Inst. Brew. 2010, 116, 251–260. DOI: 10.1002/j.2050-0416.2010.tb00428.x.
   Web of Science ®Google Scholar
• Kishimoto, T.; Wanikawa, A.; Kagami, N.; Kawatsura, K. Analysis of Hop-Derived Terpenoids in Beer and Evaluation of Their Behavior Using the Stir Bar-Sorptive Extraction Method with GC-MS. J. Agric. Food Chem. 2005, 53, 4701–4707. DOI: 10.1021/jf050072f.
   PubMed Web of Science ®Google Scholar
• Kirkpatrick, K.; Shellhammer, T. Evidence of Dextrin Hydrolyzing Enzymes in Cascade Hops (Humulus lupulus). J. Agric. Food Chem. 2018, 66, 9121–9126. DOI: 10.1021/acs.jafc.8b03563.
   PubMed Web of Science ®Google Scholar
• Cocuzza, S.; Zarnkow, M.; Stallforth, A.; Peifer, F.; Jacob, F. The Impact of Dry Hopping on Selected Physical and Chemical Attributes of Beer. Brew. Sci. 2019, 72, 118–124.
   Web of Science ®Google Scholar
• Tsuchiya, Y.; Ota, T.; Yoshimoto, H.; Kobayashi, O.; Inadome, H. Effect on Fermentation of Adding Hops to the Fermentation Tank. Brewing Summit. 2018, A-127.
   Google Scholar
• Takoi, K.; Itoga, Y.; Takayanagi, J.; Matsumoto, I.; Nakayama, Y. Control of Hop Aroma Impression of Beer with Blend-Hopping Using Geraniol-Rich Hop and New Hypothesis of Synergy among Hop-Derived Flavour Compounds. Brew. Sci. 2016, 69, 85–93.
   Web of Science ®Google Scholar
• Kishimoto, T.; Kobayashi, M.; Yako, N.; Iida, A.; Wanikawa, A. Comparison of 4-Mercapto-4-Methylpentan-2-One Contents in Hop Cultivars from Different Growing Regions. J. Agric. Food Chem. 2008, 56, 1051–1057. DOI: 10.1021/jf072173e.
   PubMed Web of Science ®Google Scholar
• Kankolongo Cibaka, M. L.; Decourriere, L.; Lorenzo-Alonso, C. J.; Bodart, E.; Robiette, R.; Collin, S. 3-Sulfanyl-4-Methylpentan-1-ol in Dry-Hopped Beers: First Evidence of Glutathione S-Conjugates in Hop (Humulus lupulus L.). J. Agric. Food Chem. 2016, 64, 8572–8582. DOI: 10.1021/acs.jafc.6b03788.
   Web of Science ®Google Scholar
• Hanke, S. Linalool: A Key Contributor to Hop Aroma. MBAA Global Emerging Issues, 2009. https://www.mbaa.com/brewresources/Documents/Linalool.pdf.
   Google Scholar
• Kaltner, D.; Steinhaus, M.; Mitter, W.; Biendl, M.; Schieberle, P. (R)-Linalool as Key Flavour for Hop Aroma in Beer and Its Behaviour during Beer Staling. Brew. Sci. 2003, 56, 192–196.
   Google Scholar
• Smadja, J.; Rondeau, P.; Sing, A. S. C. Volatile Constituents of Five Citrus Petitgrain Essential Oils from Reunion. Flavour Fragr. J. 2005, 20, 399–402. DOI: 10.1002/ffj.1438.
   Web of Science ®Google Scholar
• Eri, S.; Khoo, B. K.; Lech, J.; Hartman, T. G. Direct Thermal Desorption-Gas Chromatography and Gas Chromatography-Mass Spectrometry Profiling of Hop (Humulus lupulus L.) Essential Oils in Support of Varietal Characterization. J. Agric. Food Chem. 2000, 48, 1140–1149. DOI: 10.1021/jf9911850.
   PubMed Web of Science ®Google Scholar
• Nance, M. R.; Setzer, W. N. Volatile Components of Aroma Hops (Humulus lupulus L.) Commonly Used in Beer Brewing. J. Brew. Distill. 2011, 2, 16–22.
   Google Scholar
• Gancel, A. L.; Ollitrault, P.; Froelicher, Y.; Tomi, F.; Jacquemond, C.; Luro, F.; Brillouet, J. M. Leaf Volatile Compounds of Six Citrus Somatic Allotetraploid Hybrids Originating from Various Combinations of Lime, Lemon, Citron, Sweet Orange, and Grapefruit. J. Agric. Food Chem. 2005, 53, 2224–2230. DOI: 10.1021/jf048315b.
   PubMed Web of Science ®Google Scholar
• Van Opstaele, F.; Praet, T.; Aerts, G.; De Cooman, L. Characterization of Novel Single-Variety Oxygenated Sesquiterpenoid Hop Oil Fractions Via Headspace Solid-Phase Microextraction and Gas Chromatography-Mass Spectrometry/Olfactometry. J. Agric. Food Chem. 2013, 61, 10555–10564. DOI: 10.1021/jf402496t.
   PubMed Web of Science ®Google Scholar
• Sant'Anna, B. M. P.; Fontes, S. P.; Pinto, A. C.; Rezende, C. M. Characterization of Woody Odorant Contributors in Copaiba Oil (Copaifera multijuga Hayne). J. Braz. Chem. Soc. 2007, 18, 984–989. DOI: 10.1590/S0103-50532007000500016.
   Web of Science ®Google Scholar
• Deinzer, M.; Yang, X. Hop Aroma: character Impact Compounds Found in Beer, Methods of Formation of Individual Compounds. In EBC Monograph XXII. Symposium on Hops, Zoeterwoude, the Netherlands, Getränke-Fachverlag Hans Carl: Nürnberg, Germany, 1994; pp 181–197.
   Google Scholar
• Fukuoka, Y.; Kowaka, M. Identification of Compounds Imparting Hoppy Flavour to Beer. Rep. Res. Lab. Kirin Brew. Co. 1983, 26, 31–36.
   Google Scholar
• Goiris, K.; Ridder, M.; Rouck, G.; Boeykens, A.; Opstaele, F.; Aerts, G.; Cooman, L.; Keukeleire, D. The Oxygenated Sesquiterpenoid Fraction of Hops in Relation to the Spicy Hop Character of Beer. J. Inst. Brew. 2002, 108, 86–93. DOI: 10.1002/j.2050-0416.2002.tb00129.x.
   Web of Science ®Google Scholar
• Sanchez, N. B.; Lederer, C. L.; Nickerson, G. B.; Libbey, L. M.; McDaniel, M. R. Sensory and Analytical Evaluation of Hop Oil Oxygenated Fractions. In Developments in Food Science; Charalambous, G., Ed.; Elsevier Science: Amsterdam, 1992, pp 371–402.
   Google Scholar
• Neiens, S. D.; Steinhaus, M. Odor-Active Compounds in the Special Flavor Hops Huell Melon and Polaris. J. Agric. Food Chem. 2018, 66, 1452–1460. DOI: 10.1021/acs.jafc.7b05859.
   Web of Science ®Google Scholar
• Takoi, K.; Itoga, Y.; Koie, K.; Takayanagi, J.; Kaneko, T.; Watanabe, T.; Matsumoto, I.; Nomura, M. Behaviour of Hop-Derived Branched-Chain Esters during Fermentation and Unique Characteristics of Huell Melon and Ekuanot (HBC366) Hops. Brew. Sci. 2018, 71, 100–109.
   Web of Science ®Google Scholar
• Kishimoto, T.; Wanikawa, A.; Kono, K.; Aoki, K. Odorants Comprising Hop Aroma of Beer: hop-Derived Odorants Increased in the Beer Hopped with Aged Hops. Proc. Eur. Brew. Conv. Congr.,Venice, Italy, pp 226–235, 2007.
   Google Scholar
• 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. DOI: 10.1016/j.jbiosc.2018.03.015.
   PubMed Web of Science ®Google Scholar