Genuine Geruchssignaturen der Natur – Perspektiven aus der Lebensmittelchemie für die Biotechnologie

Die Geruchsqualitaten naturlicher Duftobjekte werden durch die geruchsstoffinduzierten Aktivierungsmuster olfaktorischer Rezeptoren definiert. Die Meta-Analyse in diesem Aufsatz zeigt, dass von den bislang ca. 10 000 in Lebensmitteln identifizierten fluchtigen Verbindungen nur ca. 230 zu den genuinen Schlusselgeruchsstoffen zahlen und der typische Geruch von Lebensmitteln durch das charakteristische Verhaltnis von nur 3–40 dieser Verbindungen kodiert wird. Dies lasst auf eine Coevolution naturlicher Geruchsstoffmolekule unserer Nahrung und der etwa 400 humanen Geruchsrezeptorproteine schliesen. Der Aufsatz gibt einen Uberblick uber die genuinen Signaturen naturlicher Geruchsobjekte und die chemische Geruchskodierung von mehr als 220 Lebensmitteln. Es werden biotechnologische Perspektiven fur die Herstellung biomimetischer Rekombinate diskutiert, mit denen erstmals die authentische Rekonstruktion naturlicher Geruchssignaturen zur Verwendung in Aromen und Parfums, biomedizinischen Applikationen, virtuellen Umgebungen oder humanoiden bioelektronischen Nasen moglich wird.

[1]  Andreas Schmid,et al.  The production of fine chemicals by biotransformations. , 2002, Current opinion in biotechnology.

[2]  Anne Didier,et al.  Humans and Mice Express Similar Olfactory Preferences , 2009, PloS one.

[3]  Nathanael Weill Chemogenomic approaches for the exploration of GPCR space. , 2011, Current topics in medicinal chemistry.

[4]  Alois Jungbauer,et al.  Continuous downstream processing of biopharmaceuticals. , 2013, Trends in biotechnology.

[5]  Tai Hyun Park,et al.  Bioelectronic nose with high sensitivity and selectivity using chemically functionalized carbon nanotube combined with human olfactory receptor. , 2012, Journal of biotechnology.

[6]  P. Schieberle,et al.  Flavor contribution and formation of the intense roast-smelling odorants 2-propionyl-1-pyrroline and 2-propionyltetrahydropyridine in Maillard-type reactions , 1998 .

[7]  B. Chiarelli,et al.  Volatile Signals During Pregnancy: A Possible Chemical Basis for Mother–Infant Recognition , 2008, Journal of Chemical Ecology.

[8]  M. Rothe,et al.  Aromastoffe des Brotes , 1963 .

[9]  D. Sell,et al.  Applied biocatalysis for the synthesis of natural flavour compounds – current industrial processes and future prospects , 2004, Biotechnology Letters.

[10]  Alphus D. Wilson,et al.  Applications and Advances in Electronic-Nose Technologies , 2009, Sensors.

[11]  P. Schieberle,et al.  Comparison of the most odor-active compounds in fresh and dried hop cones (Humulus lupulus L. variety spalter select) based on GC-olfactometry and odor dilution techniques. , 2000, Journal of agricultural and food chemistry.

[12]  S. Gravina,et al.  Human Biology of Taste , 2013, Annals of Saudi medicine.

[13]  I. Blank,et al.  Formation of odorants in Maillard model systems based on l-proline as affected by pH. , 2003, Journal of agricultural and food chemistry.

[14]  J. Schrader Microbial Flavour Production , 2007 .

[15]  P. Schieberle,et al.  Compound identification: a Journal of Agricultural and Food Chemistry perspective. , 2007, Journal of agricultural and food chemistry.

[16]  Paul N. Devine,et al.  Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture , 2010, Science.

[17]  C. Sheridan A taste of the future , 2004, Nature Biotechnology.

[18]  F. Priest,et al.  Composition of peats used in the preparation of malt for scotch whisky productioninfluence of geographical source and extraction depth. , 2009, Journal of agricultural and food chemistry.

[19]  Benoist Schaal,et al.  Human newborns prefer human milk: conspecific milk odor is attractive without postnatal exposure. , 2005, Child development.

[20]  W. Grosch Determination of potent odourants in foods by aroma extract dilution analysis (AEDA) and calculation of odour activity values (OAVs) , 1994 .

[21]  Linda B. Buck,et al.  A second class of chemosensory receptors in the olfactory epithelium , 2006, Nature.

[22]  W. Grosch,et al.  Sensory study on the character impact odorants of roasted arabica coffee. , 1999, Journal of agricultural and food chemistry.

[23]  Y. Pilpel,et al.  Mouse-human orthology relationships in an olfactory receptor gene cluster. , 2001, Genomics.

[24]  R. Khan,et al.  Perceptual convergence of multi-component mixtures in olfaction implies an olfactory white , 2012, Proceedings of the National Academy of Sciences.

[25]  A. Buettner A selective and sensitive approach to characterize odour‐active and volatile constituents in small‐scale human milk samples , 2007 .

[26]  The formation of wine lactone from grape-derived secondary metabolites. , 2011, Journal of agricultural and food chemistry.

[27]  N. Magan,et al.  Electronic noses and disease diagnostics , 2004, Nature Reviews Microbiology.

[28]  A. D. Wilson,et al.  Review of electronic-nose technologies and algorithms to detect hazardous chemicals in the environment , 2012 .

[29]  J. Pronk,et al.  The Ehrlich Pathway for Fusel Alcohol Production: a Century of Research on Saccharomyces cerevisiae Metabolism , 2008, Applied and Environmental Microbiology.

[30]  Tai Hyun Park,et al.  Recent advances in electronic and bioelectronic noses and their biomedical applications. , 2011, Enzyme and microbial technology.

[31]  I. Gaillard,et al.  Amino-acid changes acquired during evolution by olfactory receptor 912-93 modify the specificity of odorant recognition. , 2004, Human molecular genetics.

[32]  Jeffrey A. Riffell,et al.  Identification of a Testicular Odorant Receptor Mediating Human Sperm Chemotaxis , 2003, Science.

[33]  W. Meyerhof,et al.  The human vomeronasal type‐1 receptor family—detection of volatiles and cAMP signaling in HeLa/Olf cells , 2008, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[34]  Yusuf Chisti,et al.  Biotechnology-a sustainable alternative for chemical industry. , 2005, Biotechnology advances.

[35]  Stefan Krahulec,et al.  Harnessing Candida tenuis and Pichia stipitis in whole‐cell bioreductions of o‐chloroacetophenone: Stereoselectivity, cell activity, in situ substrate supply and product removal , 2013, Biotechnology journal.

[36]  R. Reed,et al.  Signal transduction in olfactory neurons , 1991, The Journal of Steroid Biochemistry and Molecular Biology.

[37]  Donald A Wilson,et al.  Olfactory perceptual stability and discrimination , 2008, Nature Neuroscience.

[38]  P. Schieberle,et al.  Reconstitution of the flavor signature of Dornfelder red wine on the basis of the natural concentrations of its key aroma and taste compounds. , 2011, Journal of agricultural and food chemistry.

[39]  Paul Richard,et al.  Using Olfactive Virtual Environments for Learning Organic Molecules , 2006, Edutainment.

[40]  J. Rehfeld,et al.  Appetite suppression through smelling of dark chocolate correlates with changes in ghrelin in young women , 2010, Regulatory Peptides.

[41]  K. Mori,et al.  Odorant Category Profile Selectivity of Olfactory Cortex Neurons , 2007, The Journal of Neuroscience.

[42]  Terry E. Acree,et al.  A Procedure for the Sensory Analysis of Gas Chromatographic Effluents , 1984 .

[43]  P. Schieberle,et al.  Evaluation of aroma differences between hand-squeezed juices from Valencia late and Navel oranges by quantitation of key odorants and flavor reconstitution experiments. , 2001, Journal of agricultural and food chemistry.

[44]  Donald A. Wilson,et al.  Odour Perception: An Object-Recognition Approach , 2007, Perception.

[45]  I. Blank Sensory Relevance of Volatile Organic Sulfur Compounds in Food , 2002 .

[46]  C. Ross,et al.  Wine matrix compounds affect perception of wine aromas. , 2013, Annual review of food science and technology.

[47]  D. Schneider Elektrophysiologische Untersuchungen von Chemo- und Mechanorezeptoren der Antenne des Seidenspinners Bombyx mori L. , 2004, Zeitschrift für vergleichende Physiologie.

[48]  R. Petit,et al.  Variation in wood volatile compounds in a mixed oak stand: strong species and spatial differentiation in whisky-lactone content , 2007, Annals of Forest Science.

[49]  P. Schieberle,et al.  Quantitative analysis of aroma compounds in wheat and rye bread crusts using a stable isotope dilution assay , 1987 .

[50]  Hiroshi Ishida,et al.  Smelling Screen: Development and Evaluation of an Olfactory Display System for Presenting a Virtual Odor Source , 2013, IEEE Transactions on Visualization and Computer Graphics.

[51]  Gustavo Glusman,et al.  The complete human olfactory subgenome. , 2001, Genome research.

[52]  R. Berger Biotechnology of flavours—the next generation , 2009, Biotechnology Letters.

[53]  Hiroshi Kataoka,et al.  Olfactory receptor antagonism between odorants , 2004, The EMBO journal.

[54]  R. Triqui,et al.  Freshness assessments of Moroccan sardine (Sardina pilchardus): comparison of overall sensory changes to instrumentally determined volatiles. , 2003, Journal of agricultural and food chemistry.

[55]  Y. Gounaris Biotechnology for the production of essential oils, flavours and volatile isolates. A review.†‡ , 2010 .

[56]  R. Rouseff,et al.  Comparison of aroma volatiles in commercial Merlot and Cabernet Sauvignon wines using gas chromatography-olfactometry and gas chromatography-mass spectrometry. , 2006, Journal of agricultural and food chemistry.

[57]  Hanns Hatt,et al.  Molecular and Cellular Basis of Human Olfaction , 2004, Chemistry & biodiversity.

[58]  Dan D. Stettler,et al.  Representations of Odor in the Piriform Cortex , 2009, Neuron.

[59]  W. Grosch Gas Chromatography—Olfactometry of Aroma Compounds , 2007 .

[60]  Yoshihito Niimura,et al.  Olfactory Receptor Multigene Family in Vertebrates: From the Viewpoint of Evolutionary Genomics , 2012, Current genomics.

[61]  M. V. Filho,et al.  Methanol-based industrial biotechnology: current status and future perspectives of methylotrophic bacteria. , 2009, Trends in biotechnology.

[62]  G. Sicard,et al.  Perceptual blending in odor mixtures depends on the nature of odorants and human olfactory expertise. , 2012, Chemical senses.

[63]  E. Sugawara,et al.  Diversity of odor-active compounds from local cultivars and wild accessions of Iwateyamanashi (Pyrus ussuriensis var. aromatica) revealed by Aroma Extract Dilution Analysis (AEDA) , 2013, Breeding science.

[64]  John-Dylan Haynes,et al.  Odor quality coding and categorization in human posterior piriform cortex , 2009, Nature Neuroscience.

[65]  Congjun Li,et al.  AKT/eNOS signaling module functions as a potential feedback loop in the growth hormone signaling pathway , 2009, Journal of molecular signaling.

[66]  Terry E. Acree,et al.  Peer Reviewed: GC/Olfactometry GC With a Sense of Smell , 1997 .

[67]  P. Dürr,et al.  THE CONTRIBUTION OF SOME VOLATILES TO THE SENSORY QUALITY OF APPLE AND ORANGE JUICE ODOUR , 1981 .

[68]  Jasmine L. Gallaher,et al.  Computational Design of an Enzyme Catalyst for a Stereoselective Bimolecular Diels-Alder Reaction , 2010, Science.

[69]  G. Blancher,et al.  Multimodal sensory integration during sequential eating--linking chewing activity, aroma release, and aroma perception over time. , 2012, Chemical senses.

[70]  J. Mattes,et al.  Sensomics analysis of taste compounds in balsamic vinegar and discovery of 5-acetoxymethyl-2-furaldehyde as a novel sweet taste modulator. , 2012, Journal of agricultural and food chemistry.

[71]  W. Grosch,et al.  Fishy and hay-like off-flavours of dry spinach , 1998 .

[72]  J. Moorhouse,et al.  Method for Use in Studies of Insect Chemical Communication , 1969, Nature.

[73]  D. G. Laing,et al.  Perception of components in binary odour mixtures , 1983 .

[74]  Arnold L. Demain,et al.  REVIEWS: The business of biotechnology , 2007 .

[75]  M. Behrens,et al.  The molecular receptive ranges of human TAS2R bitter taste receptors. , 2010, Chemical senses.

[76]  K. Krogerus,et al.  125th Anniversary Review: Diacetyl and its control during brewery fermentation , 2013 .

[77]  Tsviya Olender,et al.  Personal receptor repertoires: olfaction as a model , 2012, BMC Genomics.

[78]  D. Dubourdieu,et al.  A New Type of Flavor Precursors in Vitis vinifera L. cv. Sauvignon Blanc: S-Cysteine Conjugates , 1998 .

[79]  H. Bouwmeester Engineering the essence of plants , 2006, Nature Biotechnology.

[80]  P. Schieberle,et al.  Evaluation of the character impact odorants in fresh strawberry juice by quantitative measurements and sensory studies on model mixtures , 1997 .

[81]  K. Cadwallader,et al.  Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey. , 2002, Journal of agricultural and food chemistry.

[82]  Kea-Tiong Tang,et al.  Towards a Chemiresistive Sensor-Integrated Electronic Nose: A Review , 2013, Sensors.

[83]  H. Takeuchi,et al.  Structural determination of vanillin, isovanillin and ethylvanillin by means of gas electron diffraction and theoretical calculations , 2006 .

[84]  P. Kraft,et al.  Allerlei Trends: die neuesten Entwicklungen in der Riechstoffchemie , 2000 .

[85]  A. Dewan,et al.  Non-redundant coding of aversive odours in the main olfactory pathway , 2013, Nature.

[86]  R. Hudson,et al.  From molecule to mind: the role of experience in shaping olfactory function , 1999, Journal of Comparative Physiology A.

[87]  P. Schieberle,et al.  Identification of the key odorants in processed ribose/cysteine Maillard mixtures by instrumental analysis and sensory studies , 1996 .

[88]  Tomoko Takahashi,et al.  Deorphanization of Dresden G Protein-Coupled Receptor for an Odorant Receptor , 2007, Journal of receptor and signal transduction research.

[89]  D. Guadagni,et al.  Aroma components of olive oil , 1973 .

[90]  Imre Blank,et al.  Potent odorants of the roasted powder and brew of Arabica coffee , 1992 .

[91]  J. Giovannoni Breeding new life into plant metabolism , 2006, Nature Biotechnology.

[92]  Bastian Blombach,et al.  Bio-based production of organic acids with Corynebacterium glutamicum , 2012, Microbial biotechnology.

[93]  B. Hauer,et al.  Rational Design of Pseudozyma antarctica Lipase B Yielding a General Esterification Catalyst , 2010, Chembiochem : a European journal of chemical biology.

[94]  Horst Vogel,et al.  Characterization of an extended receptive ligand repertoire of the human olfactory receptor OR17‐40 comprising structurally related compounds , 2006, Journal of neurochemistry.

[95]  W. Schwab Genetic Engineering of Plants and Microbial Cells for Flavour Production , 2007 .

[96]  N. Ryba,et al.  Common Sense about Taste: From Mammals to Insects , 2009, Cell.

[97]  S. Vaglio,et al.  Chemical communication and mother-infant recognition , 2009, Communicative & integrative biology.

[98]  P. Schieberle New Developments in Methods for Analysis of Volatile Flavor Compounds and their Precursors , 1995 .

[99]  Gisbert Schneider,et al.  Predicting olfactory receptor neuron responses from odorant structure , 2007, Chemistry Central journal.

[100]  T. Thomas-Danguin,et al.  Just noticeable differences in component concentrations modify the odor quality of a blending mixture. , 2008, Chemical senses.

[101]  T. Hofmann,et al.  Quantitative reconstruction of the nonvolatile sensometabolome of a red wine. , 2008, Journal of agricultural and food chemistry.

[102]  W. Schwab Natural 4-Hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol®) , 2013, Molecules.

[103]  Hiroshi Kataoka,et al.  Molecular Bases of Odor Discrimination: Reconstitution of Olfactory Receptors that Recognize Overlapping Sets of Odorants , 2001, The Journal of Neuroscience.

[104]  B. Feringa,et al.  Combining Designer Cells and Click Chemistry for a One-Pot Four-Step Preparation of Enantiopure β-Hydroxytriazoles , 2010 .

[105]  Andreas Keller,et al.  The Missense of Smell: Functional Variability in the Human Odorant Receptor Repertoire , 2013, Nature Neuroscience.

[106]  P. Schieberle,et al.  Characterization of the key aroma compounds in an american bourbon whisky by quantitative measurements, aroma recombination, and omission studies. , 2008, Journal of agricultural and food chemistry.

[107]  Werner Grosch,et al.  Structure-odour-activity relationships of alkylpyrazines , 1999 .

[108]  J. Frijters A critical analysis of the odour unit number and its use , 1978 .

[109]  Relationship between the differential adsorption of odorants by the olfactory mucus and their perception in mixtures , 1988 .

[110]  Donald A Wilson,et al.  Separate encoding of identity and similarity of complex familiar odors in piriform cortex , 2006, Proceedings of the National Academy of Sciences.

[111]  Peter Bliss,et al.  The Chemical Interactions Underlying Tomato Flavor Preferences , 2012, Current Biology.

[112]  J. Mainland,et al.  Genetic variation in the odorant receptor OR2J3 is associated with the ability to detect the "grassy" smelling odor, cis-3-hexen-1-ol. , 2012, Chemical senses.

[113]  G H FULLER,et al.  THE GAS CHROMATOGRAPH WITH HUMAN SENSOR: PERFUMER MODEL , 1964, Annals of the New York Academy of Sciences.

[114]  B. Schaal,et al.  Maternal and Paternal Perception of Individual Odor Signatures in Human Amniotic Fluid – Potential Role in Early Bonding? , 1998, Neonatology.

[115]  H. Zorn,et al.  Insect-derived enzymes: a treasure for industrial biotechnology and food biotechnology. , 2013, Advances in biochemical engineering/biotechnology.

[116]  Oh Seok Kwon,et al.  Polypyrrole nanotubes conjugated with human olfactory receptors: high-performance transducers for FET-type bioelectronic noses. , 2009, Angewandte Chemie.

[117]  W. Grosch Evaluation of the key odorants of foods by dilution experiments, aroma models and omission. , 2001, Chemical senses.

[118]  C. Galizia,et al.  Weaker Ligands Can Dominate an Odor Blend due to Syntopic Interactions , 2013, Chemical senses.

[119]  A. Mosandl,et al.  Mechanism of wine lactone formation: demonstration of stereoselective cyclization and 1,3-hydride shift. , 2006, Journal of agricultural and food chemistry.

[120]  N. Stroebele,et al.  Effect of ambience on food intake and food choice. , 2004, Nutrition.

[121]  M. Sefton,et al.  The effects of size, temperature and air contact on the outcome of heating oak fragments , 2005 .

[122]  Klaus Willecke,et al.  Identification of Specific Ligands for Orphan Olfactory Receptors , 2005, Journal of Biological Chemistry.

[123]  Jian-He Xu,et al.  New opportunities for biocatalysis: driving the synthesis of chiral chemicals. , 2011, Current opinion in biotechnology.

[124]  P. Lennie,et al.  The machinery of colour vision , 2007, Nature Reviews Neuroscience.

[125]  K. Shinohara,et al.  The calming effect of a maternal breast milk odor on the human newborn infant , 2009, Neuroscience Research.

[126]  Takashi Tanaka,et al.  Whisky lactone precursors from the wood of Platycarya strobilacea , 1996 .

[127]  A. Keller,et al.  Humans Can Discriminate More than 1 Trillion Olfactory Stimuli , 2014, Science.

[128]  P. Schieberle,et al.  Sensomics analysis of key hazelnut odorants (Corylus avellana L. 'Tonda Gentile') using comprehensive two-dimensional gas chromatography in combination with time-of-flight mass spectrometry (GC×GC-TOF-MS). , 2013, Journal of agricultural and food chemistry.

[129]  M. Wüst,et al.  Stereoselective formation of the varietal aroma compound rose oxide during alcoholic fermentation. , 2008, Journal of agricultural and food chemistry.

[130]  D. Krautwurst,et al.  A hit map-based statistical method to predict best ligands for orphan olfactory receptors: natural key odorants versus "lock picks". , 2013, Methods in molecular biology.

[131]  Yan Xu,et al.  Ferulic Acid Release and 4‐Vinylguaiacol Formation during Chinese Rice Wine Brewing and Fermentation , 2010 .

[132]  D. G. Laing,et al.  The capacity of humans to identify odors in mixtures , 1989, Physiology & Behavior.

[133]  M. Crabbe,et al.  The Maillard reaction in foods and medicine , 1998 .

[134]  Peter Schieberle,et al.  Identification based on quantitative measurements and aroma recombination of the character impact odorants in a Bavarian Pilsner-type beer. , 2005, Journal of agricultural and food chemistry.

[135]  Cori Bargmann Comparative chemosensation from receptors to ecology , 2006, Nature.

[136]  D. G. Laing,et al.  The analysis of odor mixtures by humans: evidence for a configurational process , 2001, Physiology & Behavior.

[137]  J. Mainland,et al.  Odor Coding by a Mammalian Receptor Repertoire , 2009, Science Signaling.

[138]  Andréi Prida,et al.  Impact of Oak-Derived Compounds on the Olfactory Perception of Barrel-Aged Wines , 2010, American Journal of Enology and Viticulture.

[139]  K. Cadwallader,et al.  Convenient synthesis of stable deuterium-labeled alkylpyrazines for use in stable isotope dilution assays. , 2013, Journal of agricultural and food chemistry.

[140]  M. Jones-Gotman,et al.  The human brain distinguishes between single odorants and binary mixtures. , 2009, Cerebral cortex.

[141]  Roland Wohlgemuth,et al.  Biocatalysis--key to sustainable industrial chemistry. , 2010, Current opinion in biotechnology.

[142]  Z. Peterlin,et al.  Pharmacology of mammalian olfactory receptors. , 2013, Methods in molecular biology.

[143]  Masatoshi Nei,et al.  The evolution of animal chemosensory receptor gene repertoires: roles of chance and necessity , 2008, Nature Reviews Genetics.

[144]  T. Thomas-Danguin,et al.  Elemental and configural processing of odour mixtures in the newborn rabbit , 2009, Journal of Experimental Biology.

[145]  S. Liberles,et al.  Trace Amine‐associated Receptors Are Olfactory Receptors in Vertebrates , 2009, Annals of the New York Academy of Sciences.

[146]  Charles Spence,et al.  Multisensory Presence in Virtual Reality: Possibilities & Limitations. , 2011 .

[147]  J. Rospars,et al.  Competitive and Noncompetitive Odorant Interactions in the Early Neural Coding of Odorant Mixtures , 2008, The Journal of Neuroscience.

[148]  Philip Kraft,et al.  Odds and Trends: Recent Developments in the Chemistry of Odorants , 2000 .

[149]  R. Stubbs,et al.  Energy density, diet composition and palatability: influences on overall food energy intake in humans , 2004, Physiology & Behavior.

[150]  John R. Piggott,et al.  Origins of Flavour in Whiskies and a Revised Flavour Wheel: a Review , 2001 .

[151]  Gilles Laurent,et al.  Olfactory network dynamics and the coding of multidimensional signals , 2002, Nature Reviews Neuroscience.

[152]  M. Kleerebezem,et al.  Lactococcus lactis as a Cell Factory for High-Level Diacetyl Production , 2000, Applied and Environmental Microbiology.

[153]  C. Nederkoorn,et al.  Sensory-specific satiety is unaffected by manipulations of flavour intensity , 2009, Physiology & Behavior.

[154]  T. Davidek,et al.  Basic Chemistry and Process Conditions for Reaction Flavours with Particular Focus on Maillard‐Type Reactions , 2010 .

[155]  W. D. Murray,et al.  Microbiological and Enzymatic Production of Flavor and Fragrance Chemicals , 1989 .

[156]  T. Hofmann,et al.  Quantitative studies and taste re-engineering experiments toward the decoding of the nonvolatile sensometabolome of Gouda cheese. , 2008, Journal of agricultural and food chemistry.

[157]  R. Stevenson REVIEW An Initial Evaluation of the Functions of Human Olfaction , 2022 .

[158]  P. Schieberle,et al.  Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses. , 1998, Die Nahrung.

[159]  C. Derby,et al.  Generalization among related complex odorant mixtures and their components: Analysis of olfactory perception in the spiny lobster , 1996, Physiology & Behavior.

[160]  F. Priest,et al.  Decarboxylation of Substituted Cinnamic Acids by Lactic Acid Bacteria Isolated during Malt Whisky Fermentation , 2000, Applied and Environmental Microbiology.

[161]  Werner Grosch,et al.  Detection of potent odorants in foods by aroma extract dilution analysis , 1993 .

[162]  S. Kays,et al.  Analytically Directed Flavor Selection in Breeding Food Crops , 2003 .

[163]  J. Gottfried Central mechanisms of odour object perception , 2010, Nature Reviews Neuroscience.

[164]  Zhimin Huang,et al.  Crucial role of copper in detection of metal-coordinating odorants , 2012, Proceedings of the National Academy of Sciences.

[165]  Andreas Stephan,et al.  Comprehensive sensomics analysis of hop-derived bitter compounds during storage of beer. , 2011, Journal of agricultural and food chemistry.

[166]  I. S. Pretorius,et al.  Yeast and its Importance to Wine Aroma - A Review , 2019, South African Journal of Enology & Viticulture.

[167]  C. de Graaf,et al.  Sensory-specific satiety in obese and normal-weight women. , 2004, The American journal of clinical nutrition.

[168]  R. Ulber,et al.  Downstream processing in marine biotechnology. , 2005, Advances in biochemical engineering/biotechnology.

[169]  R. Axel,et al.  A novel family of genes encoding putative pheromone receptors in mammals , 1995, Cell.

[170]  P. Schieberle,et al.  2-Oxopropanal, Hydroxy-2-propanone, and 1-PyrrolineImportant Intermediates in the Generation of the Roast-Smelling Food Flavor Compounds 2-Acetyl-1-pyrroline and 2-Acetyltetrahydropyridine , 1998 .

[171]  P. Schieberle,et al.  Evaluation of key aroma compounds in hand-squeezed grapefruit juice (Citrus paradisi Macfayden) by quantitation and flavor reconstitution experiments. , 2001, Journal of agricultural and food chemistry.

[172]  David G. Laing Perceptual odour interactions and objective mixture analysis , 1994 .

[173]  Dietmar Krautwurst,et al.  Structural determinants of odorant recognition by the human olfactory receptors OR1A1 and OR1A2. , 2007, Journal of structural biology.

[174]  Loïc Briand,et al.  Comparison of odorant specificity of two human olfactory receptors from different phylogenetic classes and evidence for antagonism. , 2005, Chemical senses.

[175]  Michelle K. Beresford,et al.  A Mendelian Trait for Olfactory Sensitivity Affects Odor Experience and Food Selection , 2013, Current Biology.

[176]  E. Boido,et al.  Production of fermentation aroma compounds by Saccharomyces cerevisiae wine yeasts: effects of yeast assimilable nitrogen on two model strains. , 2008, FEMS yeast research.

[177]  M. Spehr,et al.  Odorant–Receptor Interactions and Odor Percept: A Chemical Perspective , 2008, Chemistry & biodiversity.

[178]  R. Rouseff,et al.  Pathways of 4-vinylguaiacol formation from ferulic acid in model solutions of orange juice , 1992 .

[179]  Yehudit Hasin,et al.  Genetic Elucidation of Human Hyperosmia to Isovaleric Acid , 2007, PLoS biology.

[180]  W. Grosch,et al.  Key odorants of french fries , 1998 .

[181]  E. Lavin,et al.  Odorants in breast milk. , 2003, Archives of pediatrics & adolescent medicine.

[182]  A comparison of taste test ratings, repeated consumption, and postconsumption ratings of different strengths of iced tea , 1995 .

[183]  R. Rouseff,et al.  Aroma composition changes in early season grapefruit juice produced from thermal concentration. , 2002, Journal of agricultural and food chemistry.

[184]  P. Schieberle,et al.  Character Impact Odour Compounds of Different Kinds of Butter , 1993 .

[185]  J. Keasling,et al.  Engineering a mevalonate pathway in Escherichia coli for production of terpenoids , 2003, Nature Biotechnology.

[186]  L. Vosshall,et al.  Genetic variation in a human odorant receptor alters odour perception , 2007, Nature.

[187]  P. Walla,et al.  Sensory-specific satiety with simple foods in humans: no influence of BMI? , 2007, International Journal of Obesity.

[188]  N. Issa,et al.  Glomerular activation patterns and the perception of odor mixtures , 2008, The European journal of neuroscience.

[189]  H. Schiöth,et al.  G protein-coupled receptor deorphanizations. , 2013, Annual review of pharmacology and toxicology.

[190]  Dietmar Krautwurst,et al.  Human Olfactory Receptor Families and Their Odorants , 2008, Chemistry & biodiversity.

[191]  B. Schäfer Menthol: Minze versus Tagasako-Prozess , 2013 .

[192]  R. Khan,et al.  Predicting Odor Pleasantness from Odorant Structure: Pleasantness as a Reflection of the Physical World , 2007, The Journal of Neuroscience.

[193]  B. Vanderhaegen,et al.  Ferulic acid release and 4-vinylguaiacol formation during brewing and fermentation: indications for feruloyl esterase activity in Saccharomyces cerevisiae. , 2004, Journal of agricultural and food chemistry.

[194]  A. A. Birkbeck Challenges in the Synthesis of Natural and Non‐Natural Volatiles , 2010 .

[195]  P. Fernández-Zurbano,et al.  Modeling quality of premium spanish red wines from gas chromatography-olfactometry data. , 2009, Journal of agricultural and food chemistry.

[196]  M. Bensafi,et al.  Physicochemical influence on odor hedonics , 2011 .

[197]  R. Axel,et al.  A novel multigene family may encode odorant receptors: A molecular basis for odor recognition , 1991, Cell.

[198]  S. Akutagawa Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (–)-menthol by Rh–BINAP catalysts , 1997 .

[199]  Peter Schieberle,et al.  Odor-Active Constituents in Fresh Pineapple (Ananas comosus [L.] Merr.) by Quantitative and Sensory Evaluation , 2005, Bioscience, biotechnology, and biochemistry.

[200]  P. Schieberle,et al.  Correlation between the Concentrations of Two Oak Derived Key Odorants and the Intensity of a Woody-“Barrique-Type” Odor Note in Different Red Wines , 2011 .

[201]  M. Giurfa,et al.  Antennal lobe processing increases separability of odor mixture representations in the honeybee. , 2010, Journal of neurophysiology.

[202]  T. Thomas-Danguin,et al.  Proportion of Odorants Impacts the Configural versus Elemental Perception of a Binary Blending Mixture in Newborn Rabbits , 2011 .

[203]  D. Reed,et al.  Genetics of taste and smell: poisons and pleasures. , 2010, Progress in molecular biology and translational science.

[204]  Maik Behrens,et al.  Moleküle und biologische Mechanismen des Süß‐ und Umamigeschmacks , 2011 .

[205]  A. Demain History of Industrial Biotechnology , 2010 .

[206]  I. Pretorius,et al.  The Development of Yeast Strains as Tools for Adjusting the Flavor of Fermented Beverages to Market Specifications , 2009 .

[207]  M. Miyazawa,et al.  Aroma evaluation of gamazumi (Viburnum dilatatum) by aroma extract dilution analysis and odour activity value. , 2012, Phytochemical analysis : PCA.

[208]  P. Schieberle,et al.  Evaluation of Key Odorants in Milk Chocolate and Cocoa Mass by Aroma Extract Dilution Analyses , 1997 .

[209]  M. Behrens,et al.  Sweet and umami taste: natural products, their chemosensory targets, and beyond. , 2011, Angewandte Chemie.

[210]  Masatoshi Nei,et al.  Evolutionary dynamics of olfactory receptor genes in fishes and tetrapods , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[211]  H. Guth Quantitation and Sensory Studies of Character Impact Odorants of Different White Wine Varieties , 1997 .

[212]  Yoshihito Niimura,et al.  Evolutionary dynamics of olfactory receptor genes in chordates: interaction between environments and genomic contents , 2009, Human Genomics.

[213]  L. Buck,et al.  Combinatorial Receptor Codes for Odors , 1999, Cell.

[214]  Bernhard Hauer,et al.  Recent progress in industrial biocatalysis. , 2011, Current opinion in chemical biology.

[215]  C. Guyot-Declerck,et al.  Investigation of the beta-damascenone level in fresh and aged commercial beers. , 2002, Journal of agricultural and food chemistry.

[216]  I. Rodriguez,et al.  A putative pheromone receptor gene expressed in human olfactory mucosa , 2000, Nature Genetics.

[217]  T. Michael,et al.  The tomato genome fleshed out , 2012, Nature Biotechnology.

[218]  H. Zorn,et al.  Fungal secretomes—nature’s toolbox for white biotechnology , 2008, Applied Microbiology and Biotechnology.