Identification of new glycosidic terpenols and norisoprenoids (aroma precursors) in C. arabica L. green coffee by using a high-resolution mass spectrometry database developed in grape metabolomics

Current Research in Food Science - Tập 5 - Trang 336-344 - 2022
Mirko De Rosso1, Valentina Lonzarich2, Luciano Navarini3, Riccardo Flamini1
1Council for Agricultural Research and Economics – Viticulture & Oenology (CREA-VE), Viale XXVIII Aprile 26, 31015 Conegliano, TV, Italy
2Aromalab, Illycaffè S.p.A., AREA Science Park, Padriciano 99, 34149 Trieste, Italy
3illycaffè S.p.A., Via Flavia 110, 34147 Trieste, Italy

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Tài liệu tham khảo

Akiyama, 2008, Compounds of freshly brewed arabica coffees and studies on a characteristic aroma compound of Ethiopian coffee, J. Food Sci., 73, 335, 10.1111/j.1750-3841.2008.00752.x

Alonso-Salces, 2009, Rapid Commun. Mass Spectrom., 23, 363, 10.1002/rcm.3884

Alonso-Salces, 2009, Botanical and geographical characterization of green coffee (Coffea arabica and Coffea canephora): chemometric evaluation of phenolic and methylxanthine contents, J. Agric. Food Chem., 57, 4224, 10.1021/jf8037117

Baeza, 2016, Exhaustive qualitative LC-DAD-MSn analysis of arabica green coffee beans: cinnamoyl-glycosides and cinnamoylshikimic acids as new polyphenols in green coffee, J. Agric. Food Chem., 64, 9663, 10.1021/acs.jafc.6b04022

Bonnlaender, 2004, Analysis of enantiomeric linalool ratio in green and roasted coffee, J. Flavour Fragrance, 21, 637, 10.1002/ffj.1633

Caffrey, 2020, Direct analysis of glycosidic aroma precursors containing multiple aglycone classes in vitis vinifera berries, J. Agric. Food Chem., 68, 3817, 10.1021/acs.jafc.9b08323

Cantergiani, 2001, Characterisation of the aroma of green Mexican coffee and identification of mouldy/earthy defect, Eur. Food Res. Technol., 212, 648, 10.1007/s002170100305

2001

Czerny, 2000, Potent odorants of raw arabica coffee. Their changes during roasting, J. Agric. Food Chem., 48, 868, 10.1021/jf990609n

D'Ambrosio, 2019, Advances in the dereplication of aroma precursors from grape juice by pretreatment with lead acetate and combined HILIC- and RP-HPLC methods, Foods, 8, 1

Degenhardt, 2006, Carotenoids as flavour precursors in coffee, Dev. Food Sci., 43, 379, 10.1016/S0167-4501(06)80090-7

Delcroix, 1994, Glycosidase activities of three enological yeast strains during winemaking: effect on the terpenol content of Muscat wine, Am. J. Enol. Vitic., 45, 291, 10.5344/ajev.1994.45.3.291

Del Terra, 2013, Functional characterization of three Coffea arabica L. monoterpene synthases: insights into the enzymatic machinery of coffee aroma, Phytochemistry, 89, 6, 10.1016/j.phytochem.2013.01.005

Di Stefano, 1992, Transformation of nerol and geraniol induced by yeasts, Rivista di Viticoltura ed Enologia, 45, 43

Flament, 2002

Flamini, 2018, Combining LC-MS/MS approaches to study monoterpene glycosides (aroma precursors) in grape, J. Mass Spectrom., 53, 792, 10.1002/jms.4212

Flamini, 2010

Flamini, 2013, An innovative approach to grape metabolomics: stilbene profiling by suspect screening analysis, Metabolomics, 9, 1243, 10.1007/s11306-013-0530-0

Flamini, 2014, Profiling of grape monoterpene glycosides (aroma precursors) by ultra-liquid chromatography-high resolution mass spectrometry (UHPLC/QTOF), J. Mass Spectrom., 49, 1214, 10.1002/jms.3441

Godshaw, 2019, Changes in glycosylation patterns of monoterpenes during grape berry maturation in six cultivars of Vitis vinifera, Food Chem., 297, 1

Hattori, 2004, Formation mechanism of 2,6-dimethyl-2,6-octadienes from thermal decomposition of linalyl-β-D-glucopyranoside, Biosci. Biotechnol. Biochem., 68, 2656, 10.1271/bbb.68.2656

Ida, 2021, Isolation and characterization of linalool UDP-Glc glycosyltransferases from Coffea arabica

Ilc, 2016, Meta-analysis of the core aroma components of grape and wine aroma, Front. Plant Sci., 7, 10.3389/fpls.2016.01472

Iwasa, 2015, Identification of 3-methylbutanoyl glycosides in green Coffea arabica beans as causative determinants for the quality of coffee flavors, J. Agric. Food Chem., 63, 3742, 10.1021/jf5054047

Jaiswal, 2014, Identification and characterization of the phenolic glycosides of Lagenaria siceraria stand. (Bottle Gourd) fruit by liquid Chromatography−Tandem mass spectrometry, J. Agric. Food Chem., 62, 1261, 10.1021/jf4053989

Maicas, 2005, Hydrolysis of terpenyl glycosides in grape juice and other fruit juices: a review, Appl. Microbiol. Biotechnol., 67, 322, 10.1007/s00253-004-1806-0

Marlatt, 1992, Studies of aroma constituents bound as glycosides in tomato, J. Agric. Food Chem., 40, 249, 10.1021/jf00014a016

Mateo, 2000, Monoterpenes in grape juice and wines, J. Chromatogr. A, 881, 557, 10.1016/S0021-9673(99)01342-4

Mayer, 1999, Influence of provenance and roast degree on the composition of potent odorants in Arabica coffees, Eur. Food Res. Technol., 209, 242, 10.1007/s002170050487

Nakahara, 2016

Saw, 2015, A comparative study of the volatile constituents of southeast Asian Coffea arabica, Coffea liberica and Coffea robusta green beans and their antioxidant activities, J. Essent. Oil Bearing Plants, TEOP, 18, 64, 10.1080/0972060X.2014.977580

Scalbert, 2009, Mass spectrometry-based metabolomics: limitations and recommendations for future progress with particular focus on nutrition research, Metabolomics, 5, 435, 10.1007/s11306-009-0168-0

Sefton, 2011, Occurrence, sensory impact, formation, and fate of damascenone in grapes, wines, and other foods and beverages, J. Agric. Food Chem., 59, 9717, 10.1021/jf201450q

Sharp, 2017, Examination of glycoside hydrolysis methods for the determination of terpenyl glycoside contents of different hop cultivars, J. Am. Soc. Brew. Chem., 75, 101

Simkin, 2010, Carotenoid profiling and the expression of carotenoid biosynthetic genes in developing coffee grain, Plant Physiol. Biochem., 48, 434, 10.1016/j.plaphy.2010.02.007

Skouroumounis, 2002, The formation of β-damascenone in wine, 241

Skouroumounis, 2000, Acid-catalyzed hydrolysis of alcohols and their β-D-glucopyranosides, J. Agric. Food Chem., 48, 2033, 10.1021/jf9904970

Song, 2020, Profiling terpene glycosides from ecolly, cabernet gernischet, and muscat hamburg grapes by ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry, J. Food Sci., 85, 2032, 10.1111/1750-3841.15167

Stredansky, 2018, Rapid sucrose monitoring in green coffee samples using multienzymatic biosensor, Food Chem., 254, 8, 10.1016/j.foodchem.2018.01.171

Versini, 2002, Formation of 1,6,6-trimethyl-1,2-dihydronaphtalene and other norisoprenoids in wine: considerations on the kinetics, 285

Weckerle, 2002, 3-Methylbutanoyl and 3-methylbut-2-enoyl disaccharides from green coffee beans (Coffea arabica), Phytochemistry, 60, 409, 10.1016/S0031-9422(02)00042-0

Weckerle, 2003, Linalool disaccharides as flavour precursors from green coffee beans (Coffea arabica), Eur. Food Res. Technol., 216, 6, 10.1007/s00217-002-0614-y

Wei, 2021, Comparative analysis of glycosidic aroma compound profiling in three vitis vinifera varieties by using ultra-high-performance liquid chromatography quadrupole-time-of-flight mass spectrometry, Front. Plant Sci., 12, 10.3389/fpls.2021.694979

Williams, 1982, Use of C18 reversed-phase liquid chromatography for the isolation of monoterpene glycosydes and nor-isoprenoid precursors from grape juices and wines, J. Chromatogr. A, 235, 471, 10.1016/S0021-9673(00)85911-7

Wirth, 2001, Volatile compounds released by enzymatic hydrolysis of glycoconjugates of leaves and grape berries from Vitis vinifera Muscat of Alexandria and Shiraz cultivars, J. Agric. Food Chem., 49, 2917, 10.1021/jf001398l

Xie, 2012, Investigation on pyrolysis behavior and decomposition compounds of three synthesized glycosidically bond flavor precursors, Thermochim. Acta, 532, 2, 10.1016/j.tca.2011.08.019

Yang, 2013, Recent studies of the volatile compounds in tea, Food Res. Int., 53, 585, 10.1016/j.foodres.2013.02.011

Yener, 2015, Tracing coffee origin by direct injection headspace analysis with PTR/SRI-MS, Food Res. Int., 69, 235, 10.1016/j.foodres.2014.12.046