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Research Article

Investigation of Stereoisomer Distribution and Thermochemical Conversion of Eight Terpene Alcohols Derived from Different Varieties of Chinese Hops (Humulus lupulus L.)

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Pages 185-194 | Received 28 Aug 2019, Accepted 02 Mar 2020, Published online: 07 Apr 2020

Literature cited

  • Tkachev, A. V. Chirospecific Analysis of Volatile Plant Substances. Usp. Khim. 2007, 76, 1014–1033.
  • Bonaccorsi, I.; Sciarrone, D.; Cotroneo, A.; Mondello, L.; Dugo, P.; Dugo, G. Enantiomeric Distribution of Key Volatile Components in Citrus Essential Oils. Rev. Bras. Farmacogn. 2011, 21, 841–849. DOI: 10.1590/S0102-695X2011005000123.
  • Steinhaus, M.; Fritsch, H. T.; Schieberle, P. Quantitation of (R)-and (S)-Linalool in Beer Using Solid Phase Microextraction (SPME) in Combination with a Stable Isotope Dilution Assay (SIDA). J. Agric. Food Chem. 2003, 51, 7100–7105.
  • Bonnländer, B.; Cappuccio, R.; Liverani, F. S.; Winterhalter, P. Analysis of Enantiomeric Linalool Ratio in Green and Roasted Coffee. Flavour Fragr. J. 2006, 21, 637–641. DOI: 10.1002/ffj.1633.
  • Yang, T.; Zhu, Y.; Shao, C.; Zhang, Y.; Shi, J.; Lv, H.; Lin, Z. Enantiomeric Analysis of Linalool in Teas Using Headspace Solid-Phase Microextraction with Chiral Gas Chromatography. Ind. Crop. Prod. 2016, 83, 17–23. DOI: 10.1016/j.indcrop.2015.12.025.
  • Bernreuther, A.; Bank, J.; Krammer, G.; Schreier, P. Multidimensional Gas Chromatography/Mass Spectrometry: A Powerful Tool for the Direct Chiral Evaluation of Aroma Compounds in Plant Tissues I. 5-Alkanolides in Fruits. Phytochem. Anal. 1991, 2, 43–47. DOI: 10.1002/pca.2800020109.
  • Almaguer, C.; Schönberger, C.; Gastl, M.; Arendt, E. K.; Becker, T. Humulus lupulus - A Story that Begs to Be Told. A Review. J. Inst. Brew. 2014, 120, 289–314.
  • Killeen, D. P.; Watkins, O. C.; Sansom, C. E.; Andersen, D. H.; Gordon, K. C.; Perry, N. B. Fast Sampling, Analyses and Chemometrics for Plant Breeding: Bitter Acids, Xanthohumol and Terpenes in Lupulin Glands of Hops (Humulus lupulus). Phytochem. Anal. 2017, 28, 50–57.
  • Liu, Z.; Wang, L.; Liu, Y. Rapid Differentiation of Chinese Hop Varieties (Humulus lupulus) Using Volatile Fingerprinting by HS-SPME-GC-MS Combined with Multivariate Statistical Analysis. J. Sci. Food Agric. 2018, 98, 3758–3766.
  • 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.
  • Praet, T.; Van, O. F.; Steenackers, B.; De, B. J.; De, V. D.; Aerts, G.; De, C. L. Changes in the Hop-Derived Volatile Profile upon Lab Scale Boiling. Food Res. Int. 2015, 75, 1–10. DOI: 10.1016/j.foodres.2015.05.022.
  • Fritsch, H. T.; Schieberle, P. Identification Based on Quantitative Measurements and Aroma Recombination of the Character Impact Odorants in a Bavarian Pilsner-Type Beer. J. Agric. Food Chem. 2005, 53, 7544–7551. DOI: 10.1021/jf051167k.
  • Kaltner, D.; Willi, M. Changes in Hop Derived Compounds During Beer Production and Ageing. Hop Flavor and Aroma-Proceedings of the 1st International Brewers Symposium; Shellhammer, T. H., Ed.; Master Brewers Association of the Americas: St. Paul, MN, 2009.
  • Smith, R. J.; Mahiou, B.; Deinzer, M. L. Hydrolysis Products of Humulene Diepoxide A. Tetrahedron 1991, 47, 933–940. DOI: 10.1016/S0040-4020(01)80933-9.
  • Yang, X.; Lederer, C.; McDaniel, M.; Deinzer, M. Hydrolysis Products of Caryophyllene Oxide in Hops and Beer. J. Agric. Food Chem. 1993, 41, 2082–2085. DOI: 10.1021/jf00035a049.
  • Mateo, J. J.; Jimenez, M. Monoterpenes in Grape Juice and Wines. J. Chromatogr. A 2000, 881, 557–567. DOI: 10.1016/s0021-9673(99)01342-4.
  • Ribéreau-Gayon, P.; Glories, Y.; Maujean, A.; Dubourdieu, D., Eds. Handbook of Enology, Volume 2: The Chemistry of Wine-Stabilization and Treatments (Vol. 2). Wiley: Chichester, 2006.
  • Pažitná, A.; Džúrová, J.; Špánik, I. Enantiomer Distribution of Major Chiral Volatile Organic Compounds in Selected Types of Herbal Honeys. Chirality 2014, 26, 670–674. DOI: 10.1002/chir.22364.
  • Špánik, I.; Pažitná, A.; Šiška, P.; Szolcsányi, P. The Determination of Botanical Origin of Honeys Based on Enantiomer Distribution of Chiral Volatile Organic Compounds. Food Chem. 2014, 158, 497–503. DOI: 10.1016/j.foodchem.2014.02.129.
  • Rettberg, N.; Thörner, S.; Garbe, L. Bugging Hop Analysis - On the Isomerization and Oxidation of Terpene Alcohols during Steam Distillation. BrewingScience 2012, 65, 112–117.
  • Pickett, J.; Coates, J.; Sharpe, F. R. Distortion of Essential Oil Composition during Isolation by Steam Distillation. Chem. Ind. 1975, 13, 571–572.
  • Dieckmann, R. H.; Palamand, S. R. Autoxidation of Some Constituents of Hops. I. Monoterpene Hydrocarbon, Myrcene. J. Agric. Food Chem. 1974, 22, 498–503. DOI: 10.1021/jf60193a033.
  • Hagvall, L.; Bäcktorp, C.; Svensson, S.; Nyman, G.; Börje, A.; Karlberg, A. T. Fragrance Compound Geraniol Forms Contact Allergens on Air Exposure. Identification and Quantification of Oxidation Products and Effect on Skin Sensitization. Chem. Res. Toxicol. 2007, 20, 807–814. DOI: 10.1021/tx700017v.
  • Sköld, M.; Börje, A.; Harambasic, E.; Karlberg, A. T. Contact Allergens Formed on Air Exposure of Linalool. Identification and Quantification of Primary and Secondary Oxidation Products and the Effect on Skin Sensitization. Chem. Res. Toxicol. 2004, 17, 1697–1705. DOI: 10.1021/tx049831z.
  • Ramirez, G.; Lubbers, S.; Charpentier, C.; Feuillat, M.; Voilley, A.; Chassagne, D. Aroma Compound Sorption by Oak Wood in a Model Wine. J. Agric. Food Chem. 2001, 49, 3893–3897. DOI: 10.1021/jf001334a.
  • Ohta, T.; Morimitsu, Y.; Sameshima, Y.; Samuta, T.; Ohba, T. Transformation from Geraniol, Nerol and Their Glucosides into Linalool and α-Terpineol during Shochu Distillation. J. Ferment. Bioeng. 1991, 72, 347–351. DOI: 10.1016/0922-338X(91)90085-U.
  • Demyttenaere, J. C. R.; Herrera, M. D. C.; Kimpe, N. D. Biotransformation of Geraniol, Nerol and Citral by Sporulated Surface Cultures of Aspergillus niger and Penicillium sp. Phytochemistry 2000, 55, 363–373. DOI: 10.1016/S0031-9422(00)00330-7.
  • Pedersen, D. S.; Capone, D. L.; Skouroumounis, G. K.; Pollnitz, A. P.; Sefton, M. A. Quantitative Analysis of Geraniol, Nerol, Linalool, and α-Terpineol in Wine. Anal. Bioanal. Chem. 2003, 375, 517–522. DOI: 10.1007/s00216-002-1716-x.
  • Gil-Av, E.; Feibush, B.; Charles-Sigler, R. Separation of Enantiomers by Gas Liquid Chromatography with an Optically Active Stationary Phase. Tetrahedron Lett. 1966, 7, 1009–1015. DOI: 10.1016/S0040-4039(00)70231-0.
  • Kościelski, T.; Sybilska, D.; Jurczak, J. Separation of α- and β-Pinene into Enantiomers in Gas-Liquid Chromatography Systems via α-Cyclodextrin Inclusion Complexes. J. Chromatogr. A 1983, 280, 131–134. DOI: 10.1016/S0021-9673(00)91547-4.
  • Liu, Z.; Wang, L.; Liu, Y. Analyzing Differences in Freshness of SA-1 Hops by Headspace Solid-Phase Microextraction Gas Chromatography-Mass Spectrometry Combined with Chemometrics. J. Am. Soc. Brew. Chem. 2017, 75, 193–200. DOI: 10.1094/ASBCJ-2017-3238-01.
  • 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.
  • King, A.; Richard, D. J. Biotransformation of Monoterpene Alcohols by Saccharomyces cerevisiae, Torulaspora delbrueckii and Kluyveromyces lactis. Yeast 2000, 16, 499–506. DOI: 10.1002/(SICI)1097-0061(200004)16:6<499::AID-YEA548>3.0.CO;2-E.
  • 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.
  • Takoi, K.; Itoga, Y.; Takayanagi, J.; Kosugi, T.; Shioi, T.; Nakamura, T.; Watari, J. Screening of Geraniol-Rich Flavor Hop and Interesting Behavior of Beta-Citronellol during Fermentation under Various Hop-Addition Timings. J. Am. Soc. Brew. Chem. 2014, 71, 22–29.
  • Srivastava, P.; Wagh, R. S.; Naik, D. G. γ-Irradiation: A Simple Route for Isomerization of Geraniol into Nerol and Linalool. Radiochemistry 2010, 52, 561–564. DOI: 10.1134/S1066362210050206.
  • Vaudano, E.; Moruno, E. G.; Stefano, R. Modulation of Geraniol Metabolism during Alcohol Fermentation. J. Inst. Brew. 2004, 110, 213–219. DOI: 10.1002/j.2050-0416.2004.tb00205.x.
  • Lin, C.-Y.; Chen, Y.-J.; Cheng, S.-S.; Chang, S.-T. Rapid Differentiation of Three Chamaecyparis Species (Cupressaceae) Grown in Taiwan Using Solid-Phase Microextraction–Gas Chromatography/Mass Spectrometry, Cluster Analysis, and Principal Component Analysis. J. Agric. Food Chem. 2011, 59, 10854–10859. DOI: 10.1021/jf203286j.
  • Choi, H. Characteristic Odor Components of Kumquat (Fortunella japonica Swingle) Peel Oil. J. Agric. Food Chem. 2005, 53, 1642–1647. DOI: 10.1021/jf040324x.
  • Coelho, E.; Perestrelo, R.; Neng, N. R.; Câmara, J. S.; Coimbra, M. A.; Nogueira, J. M. F.; Rocha, S. M. Optimisation of Stir Bar Sorptive Extraction and Liquid Desorption Combined with Large Volume Injection-Gas Chromatography-Quadrupole Mass Spectrometry for the Determination of Volatile Compounds in Wines. Anal. Chim. Acta 2008, 624, 79–89. DOI: 10.1016/j.aca.2008.06.032.
  • Demyttenaere, J.; Vanoverschelde, J.; De, K. Biotransformation of (R)-(+)- and (S)-(-)-Citronellol by Aspergillus sp. and Penicillium sp., and the Use of Solid-Phase Microextraction for Screening. J. Chromatogr. A 2004, 1027, 137–146. DOI: 10.1016/j.chroma.2003.08.090.
  • Van Gemert, L. J. Odour Thresholds. Compilations of Odour Threshold Values in Air, Water and Other Media. Oliemans, Punter & Partners BV: Utrecht, 2003.
  • Hanke, S.; Herrmann, M.; Rückerl, J.; Schönberger, C.; Back, W. Hop Volatile Compounds (Part II): Transfer Rates of Hop Compounds from Hop Pellets to Wort and Beer. BrewingScience 2008, 61, 140–147.
  • Meng, J.-F.; Xu, T.-F.; Song, C.-Z.; Yu, Y.; Hu, F.; Zhang, L.; Zhang, Z.-W.; Xi, Z.-M. Melatonin Treatment of Pre-Veraison Grape Berries to Increase Size and Synchronicity of Berries and Modify Wine Aroma Components. Food. Chem. 2015, 185, 127–134. DOI: 10.1016/j.foodchem.2015.03.140.
  • Ohloff, G.; Klein, E. Die Absolute Konfiguration Des Linalools Durch Verknüpfung Mit Dem Pinansystem. Tetrahedron 1962, 18, 37–42. DOI: 10.1016/0040-4020(62)80021-0.
  • Padrayuttawat, A.; Yoshizawa, T.; Tamura, H.; Tokunaga, T. Optical Isomers and Odor Thresholds of Volatile Constituents in Citrus Sudachi. Food. Sci. Technol. Res. 2009, 3, 402–408. DOI: 10.3136/fsti9596t9798.3.402.
  • Peinado, R.; Moreno, J.; Bueno, J.; Moreno, J.; Mauricio, J. Comparative Study of Aromatic Compounds in Two Young White Wines Subjected to Pre-Fermentative Cryomaceration. Food Chem. 2004, 84, 585–590. DOI: 10.1016/S0308-8146(03)00282-6.
  • Perestrelo, R.; Fernandes, A.; Albuquerque, F.; Marques, J.; Câmara, J. Analytical Characterization of the Aroma of Tinta Negra Mole Red Wine: Identification of the Main Odorants Compounds. Anal. Chim. Acta 2006, 563, 154–164. DOI: 10.1016/j.aca.2005.10.023.

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