Structure–odour relationships reviewed in the postgenomic era

This review reports on the knowledge about odourant–olfactory receptor interactions and their projection within the field of structure–odour relationships (SOR). We provide a list of agonists and odour spaces associated with deorphanized human olfactory receptors. The link between olfactory receptor responses, differential perception and subtleties within odour families is discussed. Copyright © 2015 John Wiley & Sons, Ltd.

[1]  D. D. Hunter,et al.  An Olfactory Sensory Neuron Line, Odora, Properly Targets Olfactory Proteins and Responds to Odorants , 1999, The Journal of Neuroscience.

[2]  A. Plotto,et al.  Characterization of Changes in ‘Gala’ Apple Aroma during Storage Using Osme Analysis, a Gas Chromatography–Olfactometry Technique , 2000 .

[3]  C. Wysocki,et al.  A genome-wide study on the perception of the odorants androstenone and galaxolide. , 2012, Chemical senses.

[4]  Tai Hyun Park,et al.  Enhancement of odorant detection sensitivity by the expression of odorant-binding protein. , 2008, Biosensors & bioelectronics.

[5]  Wenlai Fan,et al.  Headspace solid phase microextraction and gas chromatography-olfactometry dilution analysis of young and aged Chinese "Yanghe Daqu" liquors. , 2005, Journal of agricultural and food chemistry.

[6]  A. Stoyanova,et al.  Composition, quality control, and antimicrobial activity of the essential oil of long-time stored dill (Anethum graveolens L.) seeds from Bulgaria. , 2003, Journal of agricultural and food chemistry.

[7]  F. Heredia,et al.  Volatile components of Zalema white wines , 2007 .

[8]  C. Prost,et al.  Characterization of aroma-active compounds in rainbow trout (Oncorhynchus mykiss) eliciting an off-odor. , 2006, Journal of agricultural and food chemistry.

[9]  Chuong B. Do,et al.  A genetic variant near olfactory receptor genes influences cilantro preference , 2012, Flavour.

[10]  I. Simon,et al.  Allelic inactivation regulates olfactory receptor gene expression , 1994, Cell.

[11]  S. Schiffmann,et al.  Expression of members of the putative olfactory receptor gene family in mammalian germ cells , 1992, Nature.

[12]  B. Ache,et al.  Phosphoinositide 3-Kinase-Dependent Antagonism in Mammalian Olfactory Receptor Neurons , 2011, The Journal of Neuroscience.

[13]  A. Bouseta,et al.  Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis. , 2005, Journal of agricultural and food chemistry.

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

[15]  Jérôme Golebiowski,et al.  StructureOdor Relationships of Semisynthetic β‐Santalol Analogs , 2014, Chemistry & biodiversity.

[16]  Hanns Hatt,et al.  A specific heat shock protein enhances the expression of mammalian olfactory receptor proteins. , 2006, Chemical senses.

[17]  Nagarajan Vaidehi,et al.  Test of the Binding Threshold Hypothesis for olfactory receptors: Explanation of the differential binding of ketones to the mouse and human orthologs of olfactory receptor 912‐93 , 2005, Protein science : a publication of the Protein Society.

[18]  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.

[19]  H. Débat,et al.  Identification of human olfactory cleft mucus proteins using proteomic analysis. , 2007, Journal of proteome research.

[20]  Maurice Chastrette,et al.  Structure-Odor Relationships: Using Neural Networks in the Estimation of Camphoraceous or Fruity Odors and Olfactory Thresholds of Aliphatic Alcohols , 1996, J. Chem. Inf. Comput. Sci..

[21]  G. Gisselmann,et al.  Functional expression and characterization of a Drosophila odorant receptor in a heterologous cell system , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[22]  Gerhard Buchbauer,et al.  Solid phase microextraction/gas chromatographic and olfactory analysis of the scent and fixative properties of the essential oil of Rosa damascena L. from China , 2005 .

[23]  Yaowapa Lorjaroenphon,et al.  Characterization of typical potent odorants in cola-flavored carbonated beverages by aroma extract dilution analysis. , 2015, Journal of agricultural and food chemistry.

[24]  P. Duchamp-Viret,et al.  Interactions of odorants with olfactory receptors and receptor neurons match the perceptual dynamics observed for woody and fruity odorant mixtures , 2012, The European journal of neuroscience.

[25]  J. Hirono,et al.  Relationship between peripheral receptor code and perceived odor quality. , 2008, Chemical senses.

[26]  M. Rychlik,et al.  Impact of estragole and other odorants on the flavour of anise and tarragon , 2007 .

[27]  Zhishang Zhou,et al.  Prominent Roles for Odorant Receptor Coding Sequences in Allelic Exclusion , 2007, Cell.

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

[29]  G. Sicard,et al.  Odorant Metabolism Catalyzed by Olfactory Mucosal Enzymes Influences Peripheral Olfactory Responses in Rats , 2013, PloS one.

[30]  William A. Goddard,et al.  How broadly tuned olfactory receptors equally recognize their agonists. Human OR1G1 as a test case , 2012, Cellular and Molecular Life Sciences.

[31]  T. Abaffy,et al.  Discovery of Novel Ligands for Mouse Olfactory Receptor MOR42-3 Using an In Silico Screening Approach and In Vitro Validation , 2014, PloS one.

[32]  Karine Badonnel,et al.  On a chip demonstration of a functional role for Odorant Binding Protein in the preservation of olfactory receptor activity at high odorant concentration. , 2008, Lab on a chip.

[33]  R. Rouseff,et al.  Identification of new strawberry sulfur volatiles and changes during maturation. , 2011, Journal of agricultural and food chemistry.

[34]  Marc Spehr,et al.  β-Arrestin2-Mediated Internalization of Mammalian Odorant Receptors , 2006, The Journal of Neuroscience.

[35]  M. Madruga,et al.  Determination of some water-soluble aroma precursors in goat meat and their enrolment on flavour profile of goat meat , 2010 .

[36]  Hanns Hatt,et al.  Specificity and Sensitivity of a Human Olfactory Receptor Functionally Expressed in Human Embryonic Kidney 293 Cells andXenopus Laevis Oocytes , 1999, The Journal of Neuroscience.

[37]  L. Briand,et al.  Odorant‐Binding Proteins and Xenobiotic Metabolizing Enzymes: Implications in Olfactory Perireceptor Events , 2013, Anatomical record.

[38]  T. Bonhoeffer,et al.  Tuning and Topography in an Odor Map on the Rat Olfactory Bulb , 2001, The Journal of Neuroscience.

[39]  C. D. de March,et al.  A computational microscope focused on the sense of smell. , 2014, Biochimie.

[40]  H. Matsunami,et al.  QM/MM model of the mouse olfactory receptor MOR244-3 validated by site-directed mutagenesis experiments. , 2014, Biophysical journal.

[41]  G. Gisselmann,et al.  Expression Profile of Ectopic Olfactory Receptors Determined by Deep Sequencing , 2013, PloS one.

[42]  M. Díaz-Maroto,et al.  Aroma‐active compounds of American, French, Hungarian and Russian oak woods, studied by GC–MS and GC–O , 2008 .

[43]  Harumi Saito,et al.  RTP Family Members Induce Functional Expression of Mammalian Odorant Receptors , 2004, Cell.

[44]  M. Chastrette,et al.  A multidimensional statistical study of similarities between 74 notes used in perfumery , 1988 .

[45]  C. Finn,et al.  Impact of growing environment on chickasaw blackberry (Rubus L.) aroma evaluated by gas chromatography olfactometry dilution analysis. , 2005, Journal of agricultural and food chemistry.

[46]  D. Häussinger,et al.  Monoterpene (-)-citronellal affects hepatocarcinoma cell signaling via an olfactory receptor. , 2015, Archives of biochemistry and biophysics.

[47]  E. Polak.  Mutiple profile-multiple receptor site model for vertebrate olfaction. , 1973, Journal of theoretical biology.

[48]  P. Kraft,et al.  Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants , 2004 .

[49]  Peter Schieberle,et al.  Nature's chemical signatures in human olfaction: a foodborne perspective for future biotechnology. , 2014, Angewandte Chemie.

[50]  R. Rouseff,et al.  Gas chromatographic-olfactometric characterization of aroma active compounds in sun-dried and vacuum-dried tarhana , 2004 .

[51]  Hyang-Sook Choi,et al.  Character impact odorants of Citrus Hallabong [(C. unshiu Marcov x C. sinensis Osbeck) x C. reticulata Blanco] cold-pressed peel oil. , 2003, Journal of agricultural and food chemistry.

[52]  Patrick Etiévant,et al.  Functional characterization of two human olfactory receptors expressed in the baculovirus Sf9 insect cell system. , 2005, Chemical senses.

[53]  Synthesis and odour properties of floral smelling compounds , 1996, International journal of cosmetic science.

[54]  Huanlu Song,et al.  Formation mechanism of volatile and non-volatile compounds in peptide–xylose Maillard reaction , 2013 .

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

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

[57]  Pedro A. F. Galante,et al.  Identification of agonists for a group of human odorant receptors , 2015, Front. Pharmacol..

[58]  C. Olsen,et al.  Aroma changes during black currant (Ribes nigrum L.) nectar processing , 1998 .

[59]  Ramón Aparicio,et al.  Comparative study of virgin olive oil sensory defects , 2005 .

[60]  Kazushige Touhara,et al.  Extreme expansion of the olfactory receptor gene repertoire in African elephants and evolutionary dynamics of orthologous gene groups in 13 placental mammals , 2014, Genome research.

[61]  M. Petersen,et al.  Comparison of isolation methods for the determination of important aroma compounds in black currant (Ribes nigrum L.) juice, using nasal impact frequency profiling. , 2004, Journal of agricultural and food chemistry.

[62]  C. Sung,et al.  Phenylethyl alcohol (PEA) application slows fungal growth and maintains aroma in strawberry , 2007 .

[63]  S. Lomvardas,et al.  Stochastic gene expression in mammals: lessons from olfaction. , 2013, Trends in cell biology.

[64]  Rafi Haddad,et al.  A broadly tuned mouse odorant receptor that detects nitrotoluenes , 2012, Journal of neurochemistry.

[65]  Hitoshi Sakano,et al.  Olfactory Receptor and Neural Pathway Responsible for Highly Selective Sensing of Musk Odors , 2014, Neuron.

[66]  H. Breer,et al.  Cloning and expression of odorant receptors , 1993, Nature.

[67]  K. Kristiansen,et al.  Identification of Odorant-Receptor Interactions by Global Mapping of the Human Odorome , 2014, PloS one.

[68]  K. Gerwert,et al.  Prediction of a ligand-binding niche within a human olfactory receptor by combining site-directed mutagenesis with dynamic homology modeling. , 2012, Angewandte Chemie.

[69]  Relationship between sensory attributes of bakasang (a traditional Indonesian fermented fish product) and its physicochemical properties , 2011, Fisheries Science.

[70]  L. Grossman,et al.  Current relaxation of selection on the human genome: tolerance of deleterious mutations on olfactory receptors. , 2013, Molecular phylogenetics and evolution.

[71]  J. Berdagué,et al.  Novel multi-gas chromatography-olfactometry device and software for the identification of odour-active compounds. , 2007, Journal of chromatography. A.

[72]  A. Malhotra,et al.  The Molecular Basis for Ligand Specificity in a Mouse Olfactory Receptor , 2007, Journal of Biological Chemistry.

[73]  Philip Curran,et al.  Chemical composition and sensory profile of pomelo (Citrus grandis (L.) Osbeck) juice. , 2012, Food chemistry.

[74]  E. Leitner,et al.  Chemical and sensory characterisation of aroma of Viburnum opulus fruits by solid phase microextraction-gas chromatography-olfactometry , 2012 .

[75]  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.

[76]  R. Stevens,et al.  Expression and Purification of the Saccharomyces cerevisiae α-Factor Receptor (Ste2p), a 7-Transmembrane-segment G Protein-coupled Receptor* , 1997, The Journal of Biological Chemistry.

[77]  Lars Kunz,et al.  Enterochromaffin cells of the human gut: sensors for spices and odorants. , 2007, Gastroenterology.

[78]  B. Olofsson,et al.  Alkylpyrazines, volatiles formed in the Maillard reaction. II. Sensory properties of five alkylpyrazines , 1986 .

[79]  Maxime Tarabichi,et al.  Profiling of Olfactory Receptor Gene Expression in Whole Human Olfactory Mucosa , 2014, PloS one.

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

[81]  Sarah E. Repicky,et al.  Determinants of Zinc Potentiation on the α4 Subunit of Neuronal Nicotinic Receptors , 2006, Molecular Pharmacology.

[82]  S. Hoff,et al.  Characterization of volatile organic compounds and odorants associated with swine barn particulate matter using solid-phase microextraction and gas chromatography-mass spectrometry-olfactometry. , 2006, Journal of chromatography. A.

[83]  J. Reisert.  Origin of basal activity in mammalian olfactory receptor neurons , 2010, The Journal of general physiology.

[84]  Makiko Suwa,et al.  Structural Basis for a Broad But Selective Ligand Spectrum of a Mouse Olfactory Receptor: Mapping the Odorant-Binding Site , 2005, The Journal of Neuroscience.

[85]  J. Thorner,et al.  Control of yeast mating signal transduction by a mammalian beta 2-adrenergic receptor and Gs alpha subunit. , 1990, Science.

[86]  Karen J. Rossiter,et al.  Structure−Odor Relationships , 1996 .

[87]  J. Mainland,et al.  The prevalence of androstenone anosmia. , 2003, Chemical senses.

[88]  T. Singh,et al.  Odour-active compounds of Jinhua ham , 2008 .

[89]  H. Guth,et al.  Identification of Character Impact Odorants of Different White Wine Varieties , 1997 .

[90]  U. Ravid,et al.  New syntheses in dihydrojasmone series , 1974 .

[91]  P. Blache,et al.  Cloning and tissue distribution of a new rat olfactory receptor-like (OL2). , 1998, Biochemical and biophysical research communications.

[92]  M. Pfaffl,et al.  Class I odorant receptors, TAS1R and TAS2R taste receptors, are markers for subpopulations of circulating leukocytes , 2015, Journal of leukocyte biology.

[93]  Y. Niimura,et al.  Degeneration of olfactory receptor gene repertories in primates: no direct link to full trichromatic vision. , 2010, Molecular biology and evolution.

[94]  D. Enders,et al.  First asymmetric synthesis of both enantiomers of Tropional® and their olfactory evaluation , 2004 .

[95]  M. F. Furnols,et al.  Impact of consumer's sensitivity to androstenone on acceptability of meat from entire male pigs in three European countries: France, Spain and United Kingdom. , 2012, Meat science.

[96]  U. Kaupp,et al.  The CatSper channel: a polymodal chemosensor in human sperm , 2012, The EMBO journal.

[97]  Horst Vogel,et al.  Large-scale production and study of a synthetic G protein-coupled receptor: Human olfactory receptor 17-4 , 2009, Proceedings of the National Academy of Sciences.

[98]  S. Bieri,et al.  Olfactory receptor neuron profiling using sandalwood odorants. , 2004, Chemical senses.

[99]  S. Foster,et al.  Extrasensory perception: odorant and taste receptors beyond the nose and mouth. , 2014, Pharmacology & therapeutics.

[100]  L. C. Katz,et al.  Optical Imaging of Odorant Representations in the Mammalian Olfactory Bulb , 1999, Neuron.

[101]  L. Pannell,et al.  Identification of human nasal mucous proteins using proteomics , 2005, Proteomics.

[102]  Doron Lancet,et al.  Prediction of the odorant binding site of olfactory receptor proteins by human–mouse comparisons , 2004, Protein science : a publication of the Protein Society.

[103]  J. Gordon,et al.  Olfactory receptor responding to gut microbiota-derived signals plays a role in renin secretion and blood pressure regulation , 2013, Proceedings of the National Academy of Sciences.

[104]  A. Macleod,et al.  Volatile flavor components of sapodilla fruit (Achras sapota L) , 1982 .

[105]  Jordi Ballester,et al.  Selection of potential impact odorants and sensory validation of their importance in typical chardonnay wines. , 2006, Journal of agricultural and food chemistry.

[106]  D. T. Stanton,et al.  Understanding the underlying dimensions in perfumers’ odor perception space as a basis for developing meaningful odor maps , 2009, Attention, perception & psychophysics.

[107]  C. Wysocki,et al.  Genetic analysis of chemosensory traits in human twins. , 2012, Chemical senses.

[108]  H. Michel,et al.  Heterologous expression of the human D2S dopamine receptor in protease-deficient Saccharomyces cerevisiae strains. , 1994, European journal of biochemistry.

[109]  M. Niv,et al.  Aldehyde Recognition and Discrimination by Mammalian Odorant Receptors via Functional Group-Specific Hydration Chemistry , 2014, ACS chemical biology.

[110]  A. Buettner,et al.  Characterisation of odour‐active compounds in lupin flour , 2009 .

[111]  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.

[112]  Alan Carleton,et al.  Dense representation of natural odorants in the mouse olfactory bulb , 2012, Nature Neuroscience.

[113]  Torsten Schwede,et al.  The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket. , 2011, Biochemistry.

[114]  Marie-Annick Persuy,et al.  Functional expression of olfactory receptors in yeast and development of a bioassay for odorant screening , 2005, The FEBS journal.

[115]  A. Api,et al.  Fragrance material review on piperonyl acetate. , 2012, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[116]  Doron Lancet,et al.  The olfactory receptor gene superfamily: data mining, classification, and nomenclature , 2000, Mammalian Genome.

[117]  Tatjana Abaffy,et al.  Functional analysis of a mammalian odorant receptor subfamily , 2006, Journal of neurochemistry.

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

[119]  T. Getchell,et al.  Perireceptor and receptor events in vertebrate olfaction , 1984, Progress in Neurobiology.

[120]  C. Prost,et al.  Comparison of odor-active volatile compounds of fresh and smoked salmon. , 2006, Journal of agricultural and food chemistry.

[121]  A. Duchamp,et al.  ODOR DISCRIMINATION BY FROG OLFACTORY RECEPTORS , 1974 .

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

[123]  H. Matsuda,et al.  Olfactory study on optically active citronellyl derivatives , 2004 .

[124]  Z. Peterlin,et al.  The state of the art of odorant receptor deorphanization: A report from the orphanage , 2014, The Journal of general physiology.

[125]  T. Lovric,et al.  Characterization of odor-active compounds in Croatian Rhine Riesling wine, subregion Zagorje , 2006 .

[126]  L. J. Gemert,et al.  Sensory properties of optical isomers , 1993 .

[127]  Ji Hee Ha,et al.  Chemical sensing of DNT by engineered olfactory yeast strain. , 2007, Nature chemical biology.

[128]  M. Medina,et al.  Aroma series as fingerprints for biological ageing in fino sherry‐type wines , 2007 .

[129]  P. Schieberle,et al.  Differences in key odorants of handmade juice of yellow-flesh peaches (Prunus persica L.) induced by the workup procedure. , 1999, Journal of agricultural and food chemistry.

[130]  E. Mehinagic,et al.  Characterization of odor-active volatiles in apples: influence of cultivars and maturity stage. , 2006, Journal of agricultural and food chemistry.

[131]  J. Mainland,et al.  Functional Evolution of Mammalian Odorant Receptors , 2012, PLoS genetics.

[132]  M. Sawamura,et al.  Characteristic odour components of bergamot (Citrus bergamia Risso) essential oil , 2006 .

[133]  J. Amoore,et al.  Sensory Analysis of Odor Qualities in Terms of the Stereochemical Theory , 1966 .

[134]  Elisabeth Guichard,et al.  Relationships between molecular structure and perceived odor quality of ligands for a human olfactory receptor. , 2008, Chemical senses.

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

[136]  M. Miyazawa,et al.  Identification of the main aroma compounds in dried seeds of Brassica hirta , 2006, Journal of Natural Medicines.

[137]  T. Park,et al.  Specificity of odorant-binding proteins: a factor influencing the sensitivity of olfactory receptor-based biosensors , 2010, Bioprocess and biosystems engineering.

[138]  D. Dubourdieu,et al.  Characterization of key-aroma compounds of botrytized wines, influence of grape botrytization , 2007 .

[139]  Manuel Zarzo,et al.  What is a Fresh Scent in Perfumery? Perceptual Freshness is Correlated with Substantivity , 2012, Sensors.

[140]  NaNa Kang,et al.  Olfactory receptors in non-chemosensory tissues , 2012, BMB reports.

[141]  H. Tamura,et al.  Evaluation of odour‐active compounds in roasted shrimp (Sergia lucens Hansen) by aroma extract dilution analysis , 2005 .

[142]  Hanyi Zhuang,et al.  Evaluating cell-surface expression and measuring activation of mammalian odorant receptors in heterologous cells , 2008, Nature Protocols.

[143]  J. Wess,et al.  Functional expression of M1, M3 and M5 muscarinic acetylcholine receptors in yeast , 2001, Journal of neurochemistry.

[144]  H. Hatt,et al.  Prediction of perception: probing the hOR17-4 olfactory receptor model with silicon analogues of bourgeonal and lilial. , 2007, Angewandte Chemie.

[145]  P. Marriott,et al.  Identification of character-impact odorants in coriander and wild coriander leaves using gas chromatography-olfactometry (GCO) and comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC x GC-TOFMS). , 2005, Journal of separation science.

[146]  Jérôme Golebiowski,et al.  Discrimination between olfactory receptor agonists and non-agonists. , 2014, Chemistry.

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

[148]  C. Osorio,et al.  Characterization of odor-active volatiles in champa (Campomanesia lineatifolia R. and P.). , 2006, Journal of agricultural and food chemistry.

[149]  T Kobayakawa,et al.  Differences in perception of everyday odors: a Japanese-German cross-cultural study. , 1998, Chemical senses.

[150]  J. Schwartz,et al.  Cloning of OL1, a putative olfactory receptor and its expression in the developing rat heart. , 1995, Receptors & channels.

[151]  T. Kishimoto,et al.  Comparison of the odor-active compounds in unhopped beer and beers hopped with different hop varieties. , 2006, Journal of agricultural and food chemistry.

[152]  K. Touhara,et al.  An odorant derivative as an antagonist for an olfactory receptor. , 2004, Chemical senses.

[153]  H. Kataoka,et al.  Odorant response assays for a heterologously expressed olfactory receptor. , 2003, Biochemical and biophysical research communications.

[154]  F. Ivy Carroll,et al.  Varenicline Is a Partial Agonist at α4β2 and a Full Agonist at α7 Neuronal Nicotinic Receptors , 2006, Molecular Pharmacology.

[155]  J. R. Erickson,et al.  Edg-2/Vzg-1 Couples to the Yeast Pheromone Response Pathway Selectively in Response to Lysophosphatidic Acid* , 1998, The Journal of Biological Chemistry.

[156]  Maria Aparecida Azevedo Pereira da Silva,et al.  Assessment of aroma impact compounds in a cashew apple-based alcoholic beverage by GC-MS and GC-olfactometry , 2006 .

[157]  R. Rouseff,et al.  Determination of the role of valencene in orange oil as a direct contributor to aroma quality , 2005 .

[158]  B. Siegmund,et al.  Odor thresholds of microbially induced off-flavor compounds in apple juice. , 2006, Journal of agricultural and food chemistry.

[159]  D. Ulrich,et al.  Identification of potent odorants in different cultivars of snake fruit [Salacca zalacca (Gaert.) Voss] using gas chromatography-olfactometry. , 2005, Journal of agricultural and food chemistry.

[160]  David Harel,et al.  A metric for odorant comparison , 2008, Nature Methods.

[161]  F. Duke,et al.  Excretion and Perception of a Characteristic Odor in Urine after Asparagus Ingestion: a Psychophysical and Genetic Study , 2010, Chemical senses.

[162]  B. Ozenberger,et al.  Functional coupling of a mammalian somatostatin receptor to the yeast pheromone response pathway , 1995, Molecular and cellular biology.

[163]  P. Pelosi,et al.  Affinities of nutty and green-smelling pyrazines and thiazoles to odorant-binding proteins, in relation with their lipophilicity. , 1995, Chemical senses.

[164]  Yoshimasa Takahashi,et al.  Extended studies of the automated odor-sensing system based on plural semiconductor gas sensors with computerized pattern recognition techniques , 1988 .

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

[166]  Didier Grandjean,et al.  Affective dimensions of odor perception: a comparison between Swiss, British, and Singaporean populations. , 2011, Emotion.

[167]  L. Mondello,et al.  Odour fingerprint acquisition by means of comprehensive two-dimensional gas chromatography-olfactometry and comprehensive two-dimensional gas chromatography/mass spectrometry. , 2007, Journal of chromatography. A.

[168]  U. Kaupp,et al.  The CatSper channel mediates progesterone-induced Ca2+ influx in human sperm , 2011, Nature.

[169]  R. Boulanger,et al.  Impact of “ecological” post-harvest processing on the volatile fraction of coffee beans: I. Green coffee , 2007 .

[170]  Jacques Demaille,et al.  Porcine odorant-binding protein selectively binds to a human olfactory receptor. , 2002, Chemical senses.

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

[172]  E. Isacoff,et al.  Functional Identification of a Goldfish Odorant Receptor , 1999, Neuron.

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

[174]  Satoru Mihara,et al.  Olfactive properties of alkylpyrazines and 3-substituted 2-alkylpyrazines , 1988 .

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

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

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

[178]  D. Trotier,et al.  Odor similarities in structurally related odorants , 1978 .

[179]  J. Mainland,et al.  Genetic Variation of an Odorant Receptor OR7D4 and Sensory Perception of Cooked Meat Containing Androstenone , 2012, PloS one.

[180]  Gilles Sicard,et al.  Comparing the Information Content of Two Large Olfactory Databases , 2006, J. Chem. Inf. Model..

[181]  T. Smart,et al.  HEK293 cell line: a vehicle for the expression of recombinant proteins. , 2005, Journal of pharmacological and toxicological methods.

[182]  F. Jacobsen,et al.  A synthetic sandalwood odorant induces wound-healing processes in human keratinocytes via the olfactory receptor OR2AT4. , 2014, The Journal of investigative dermatology.

[183]  P. Courcoux,et al.  Effect of Storage Time on Raw Sardine (Sardina pilchardus) Flavor and Aroma Quality , 2006 .

[184]  Patrick Breheny,et al.  In Vivo Identification of Eugenol-Responsive and Muscone-Responsive Mouse Odorant Receptors , 2014, The Journal of Neuroscience.

[185]  K. Mikoshiba,et al.  Functional expression of a mammalian odorant receptor. , 1998, Science.

[186]  A. Narula.  The Search for New Fragrance Ingredients for Functional Perfumery , 2004, Chemistry & biodiversity.