[en] The olfactory sense is the dominant sensory perception for many animals. When Richard Axel and Linda Buck received in 2004 the Nobel Prize for discovering the G-protein coupled receptors role in olfactory cells, it highlighted the importance of olfaction to scientific community. Several theories tried to explain how cells are able to distinguish such a wide variety of odorant molecules in a complex context in which enantiomers can result in completely different perceptions and structurally different molecules in the same one. Moreover, sex, age, cultural origin and individual differences contribute to odor perception variations that complicate the picture. Recent advances in olfaction theory will be presented and future trends in human olfaction like structure-based odor prediction or artificial sniffing will be discussed at the frontiers of chemistry, physiology, neurobiology and machine learning.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Genva, Manon ; Université de Liège - ULiège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Chimie des agro-biosystèmes
Kenne Kemene, Tierry ; Université de Liège - ULiège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Chimie des agro-biosystèmes
Deleu, Magali ; Université de Liège - ULiège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Chimie des agro-biosystèmes
Lins, Laurence ; Université de Liège - ULiège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Chimie des agro-biosystèmes
Fauconnier, Marie-Laure ; Université de Liège - ULiège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Chimie des agro-biosystèmes
Language :
English
Title :
Is it possible to predict the odor of a molecule on the basis of its structure?
Publication date :
20 June 2019
Journal title :
International Journal of Molecular Sciences
ISSN :
1661-6596
eISSN :
1422-0067
Publisher :
Multidisciplinary Digital Publishing Institute (MDPI), Switzerland
Depelteau, J.S.; Brenzinger, S.; Briegel, A. Bacterial and Archaeal Cell Structure. In Reference Module in Life Sciences; Elsevier: Amsterdam, The Netherlands, 2019.
Grabe, V.; Sachse, S. Fundamental principles of the olfactory code. Biosystems 2018, 164, 94-101.
Choi, N.-E.; Han, J.H. How Flavor Works—The Science of Taste and Aroma; John Wiley & Sons, Ltd.: Chichester, UK, 2015.
Padodara, R.J.; Jacob, N. Olfactory Sense in Different Animals. Indian J. Vet. Sci. 2014, 2, 1-14.
Calvo-Ochoa, E.; Byrd-Jacobs, C. The Olfactory System of Zebrafish as a Model for the Study of Neurotoxicity and Injury: Implications for Neuroplasticity and Disease. Int. J. Mol. Sci. 2019, 20, 1639.
Wang, Z.; Zhou, Y.; Luo, Y.; Zhang, J.; Zhai, Y.; Yang, D.; Zhang, Z.; Li, Y.; Storm, D.; Ma, R. Gene Expression Profiles of Main Olfactory Epithelium in Adenylyl Cyclase 3 Knockout Mice. Int. J. Mol. Sci. 2015, 16, 28320-28333.
Raji, J.I.; DeGennaro, M. Genetic analysis of mosquito detection of humans. Curr. Opin. Insect Sci. 2017, 20, 34-38.
Reed, D.R.; Knaapila, A. Genetics of Taste and Smell: Poisons and Pleasures. NIH Public Access 2010, 94, 213-240.
Vaglio, S. Chemical communication and mother-infant recognition. Commun. Integr. Biol. 2009, 2, 279-281.
Sparkes, A.C. Ethnography and the senses: Challenges and possibilities. Qual. Res. Sport Exerc. 2009, 1, 21-35.
Sarafoleanu, C.; Mella, C.; Georgescu, M.; Perederco, C. The importance of the olfactory sense in the human behavior and evolution. J. Med. Life 2009, 2, 196-198.
Ferdenzi, C.; Joussain, P.; Digard, B.; Luneau, L.; Djordjevic, J.; Bensafi, M. Individual Differences in Verbal and Non-Verbal Affective Responses to Smells: Influence of Odor Label Across Cultures. Chem. Senses 2016, 42, 37-46.
Hummel, T.; Kobal, G.; Gudziol, H.; Mackay-Sim, A. Normative data for the “Sniffin’ Sticks” including tests of odor identification, odor discrimination, and olfactory thresholds: An upgrade based on a group of more than 3,000 subjects. Eur. Arch. Oto-Rhino-Laryngology 2007, 264, 237-243.
Sorokowska, A.; Hummel, T. Polska wersja testu Sniffin’ Sticks—Adaptacja i normalizacja. Otolaryngol. Pol.2014, 68, 308-314.
Sorokowska, A.; Schriever, V.A.; Gudziol, V.; Hummel, C.; Hähner, A.; Iannilli, E.; Sinding, C.; Aziz, M.; Seo, H.S.; Negoias, S, et al. Changes of olfactory abilities in relation to age: Odor identification in more than 1400 people aged 4 to 80 years. Eur. Arch. Oto-Rhino-Laryngology 2015, 272, 1937-1944.
Sorokowski, P.; Karwowski, M.; Misiak, M.; Marczak, M.K.; Dziekan, M.; Hummel, T.; Sorokowska, A. Sex differences in human olfaction: A meta-analysis. Front. Psychol. 2019, 10, 242.
Buck, L.; Axel, R. A novel multigene family may encode odorant receptors: A molecular basis for odor recognition. Cell 1991, 65, 175-187.
Herrmann, A. The Chemistry and Biology of Volatiles; Herrmann, A., Ed.; John Wiley & Sons, Ltd.: Chichester, UK, 2010; p. 428.
De Gennaro, G.; Farella, G.; Marzocca, A.; Mazzone, A.; Tutino, M. Indoor and outdoor monitoring of volatile organic compounds in school buildings: Indicators based on health risk assessment to single out critical issues. Int. J. Environ. Res. Public Health 2013, 10, 6273-6291.
Yoshii, F. Structure-odor relations: A modern perspective. In Handbook of Olfaction and Gustation; Doty, R.L., Ed.; Taylor & Francis Group: Abingdon, UK, 2003; pp. 457-492.
Nara, K.; Saraiva, L.R.; Ye, X.; Buck, L.B. A Large-Scale Analysis of Odor Coding in the Olfactory Epithelium. J. Neurosci. 2011, 31, 9179-9191.
Dufossé, L.; Latrasse, A.; Spinnler, H.-E. Importance des lactones dans les arômes alimentaires. Sci des Aliment. 1994, 14, 17-50.
Goldstein, N. Getting to know the odor compounds. Biocycle 2002, 43, 42-44.
Buettner, A. Springer Handbook of Odor; Buettner, A., Ed.; Springer International Publishing: Cham, Switzerland, 2017.
Laing, D.G. Relationship between Molecular Structure, Concentration and Odor Qualities of Oxygenated Aliphatic Molecules. Chem. Senses 2003, 28, 57-69.
Poivet, E.; Tahirova, N.; Peterlin, Z.; Xu, L.; Zou, D.-J.; Acree, T.; Firestein, S. Functional odor classification through a medicinal chemistry approach. Sci. Adv. 2018, 4, eaao6086.
Zarzo, M. Effect of Functional Group and Carbon Chain Length on the Odor Detection Threshold of Aliphatic Compounds. Sensors 2012, 12, 4105-4112.
Nobuhara, A. Syntheses of Unsaturated Lactones. Agric. Biol. Chem. 1968, 32, 1016-1020.
Brookes, J.C.; Horsfield, A.P.; Stoneham, A.M. Odour character differences for enantiomers correlate with molecular flexibility. J. R. Soc. Interface 2009, 6, 75-86.
Boelens, M.H.; van Gemert, L.J. Volatile character-impact sulfur compounds and their sensory properties. Perfum. Flavorist 1993, 18, 29-39.
Meierhenrich, U.J.; Golebiowski, J.; Fernandez, X.; Cabrol-Bass, D. De la molécule à l’odeur: Les bases moléculaires des premières étapes de l’olfaction. L. Actual. Chim. 2005, 29-40.
Kraft, P.; Bajgrowicz, J.A.; Denis, C.; Frater, G. Odds and Trends: Recent Developments in the Chemistry of Odorants. Angew. Chemie Int. Ed. 2000, 39, 2980-3010.
Brenna, E.; Fuganti, C.; Serra, S. Enantioselective perception of chiral odorants. Tetrahedron: Asymmetry 2003, 14, 1-42.
Sell, C.S. On the unpredictability of odor. Angew. Chemie Int. Ed. 2006, 45, 6254-6261.
Ohloff, G.; Maurer, B.; Winter, B.; Giersch, W. Structural and Configurational Dependence of the Sensory Process in Steroids. Org. Biol. Chemie Chim. Org. Chim. Biol. 1983, 66, 192-217.
Su, C.-Y.; Menuz, K.; Carlson, J.R. Olfactory Perception: Receptors, Cells, and Circuits. Cell 2009, 139, 45-59.
Bonfils, P. Odorat: De l’aéroportage au cortex. Bull. Acad. Natl. Med. 2014, 198, 1109-1120.
Sela, L.; Sobel, N. Human olfaction: A constant state of change-blindness. Exp. Brain Res. 2010, 205, 13-29.
Maresh, A.; Rodriguez Gil, D.; Whitman, M.C.; Greer, C.A. Principles of glomerular organization in the human olfactory bulb—Implications for odor processing. PLoS ONE 2008, 3.
Herden, G. Some aspects of qualitative data analysis. Math. Soc. Sci. 1993, 26, 105-138.
Boelens, M.H.; Boelens, H.; Van Gemert, L.J. Sensory Properties of Optical Isomers. Perfum. Flavonist 1993, 18, 1.
Chastrette, M. Classification of Odors and Structure-Odor Relationships. In Olfaction, Taste, and Cognition; Rouby, C., Schaal, B., Dubois, D., Gervais, R., Holley, A., Eds.; Cambridge University Press: Cambridge, UK, 2009; pp. 100-116.
Ohloff, G.; Winter, B.; Fehr, C. Chemical Classification and Structure—Odour Relationships. In Perfumes; Springer Netherlands: Dordrecht, Netherlands, 1994; pp. 287-330.
Jordan, R.; Kollo, M.; Schaefer, A.T. Sniffing Fast: Paradoxical Effects on Odor Concentration Discrimination at the Levels of Olfactory Bulb Output and Behavior. Eneuro 2018, 5.
Wilkes, F.J.; Laing, D.G.; Hutchinson, I.; Jinks, A.L.; Monteleone, E. Temporal processing of olfactory stimuli during retronasal perception. Behav. Brain Res. 2009, 200, 68-75.
Nagashima, A.; Touhara, K. Enzymatic Conversion of Odorants in Nasal Mucus Affects Olfactory Glomerular Activation Patterns and Odor Perception. J. Neurosci. 2010, 30, 16391-16398.
Thiebaud, N.; da Silva, S.V.; Jakob, I.; Sicard, G.; Chevalier, J.; Ménétrier, F.; Berdeaux, O.; Artur, Y.; Heydel, J.M.; Le Bon, A.M. Odorant Metabolism Catalyzed by Olfactory Mucosal Enzymes Influences Peripheral Olfactory Responses in Rats. PLoS ONE 2013, 8, 34-56.
Tegoni, M.; Pelosi, P.; Vincent, F.; Spinelli, S.; Campanacci, V.; Grolli, S.; Ramoni, R.; Cambillau, C. Mammalian odorant binding proteins. Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 2000, 1482, 229-240.
Homma, R.; Lv, X.; Sato, T.; Imamura, F.; Zeng, S.; Nagayama, S. Narrowly Confined and Glomerulus-Specific Onset Latencies of Odor-Evoked Calcium Transients in the Juxtaglomerular Cells of the Mouse Main Olfactory Bulb. Eneuro 2019, 6.
Kay, L.M.; Sherman, S.M. An argument for an olfactory thalamus. Trends Neurosci. 2007, 30, 47-53.
Geramita, M.; Urban, N.N. Differences in Glomerular-Layer-Mediated Feedforward Inhibition onto Mitral and Tufted Cells Lead to Distinct Modes of Intensity Coding. J. Neurosci. 2017, 37, 1428-1438.
Bizer, A.; Parabucki, A.; Smear, M.; Munoz, A.E.; Shusterman, R.; Bala, A.D.S.; Morris, G. Odor concentration change coding in the olfactory bulb. Eneuro 2019, 6.
Jaubert, J.N.; Tapiero, C.; Dore, J.C. The field of odours: Toward a universal language for odour relationships. Perfum. Flavorist 1995, 20, 1-16.
David, S. Linguistic Expressions for Odors in French. In Olfaction, Taste, and Cognition; Rouby, C., Schaal, B., Dubois, D., Gervais, R., Holley, A., Eds.; Cambridge University Press: Cambridge, UK, 2009; pp. 82-99.
Block, E.; Jang, S.; Matsunami, H.; Sekharan, S.; Dethier, B.; Ertem, M.Z.; Gundala, S.; Pan, Y.; Li, S.; Li, Z, et al. Implausibility of the vibrational theory of olfaction. Proc. Natl. Acad. Sci. 2015, 112, 2766-2774.
Malcolm Dyson, G. The scientific basis of odour. J. Soc. Chem. Ind. 1938, 57, 647-651.
De Jong, H.G.B.S. G.G.. model for the stimulation of organ of smell. Proc. Acad. Sci. 1937, 40, 302-306.
Davies, J.T.; Taylor, F.H. A Model System for the Olfactory Membrane. Nature 1954, 174, 693-694.
Rosenberg, B.; Misra, T.N.; Switzer, R. Mechanism of Olfactory Transduction. Nature 1968, 217, 423-427.
Mozell, M.M. Evidence for a Chromatographic Model of Olfaction. J. Gen. Physiol. 2004, 56, 46-63.
Amoore, J.E. Specific anosmia and the concept of primary odors. Chem. Senses 1977, 2, 267-281.
Triller, A.; Boulden, E.A.; Churchill, A.; Hatt, H.; Englund, J.; Spehr, M.; Sell, C.S. Odorant-Receptor Interactions and Odor Percept: A Chemical Perspective. Chem. Biodivers. 2008, 5, 862-886.
Amoore, J.E. Stereochemical theory of olfaction. Nature 1963, 198, 271-272.
Silva Teixeira, C.S.; Cerqueira, N.M.F.S.A.; Silva Ferreira, A.C. Unravelling the Olfactory Sense: From the Gene to Odor Perception. Chem. Senses 2015, 41, 105-121.
DeMaria, S.; Ngai, J. The cell biology of smell. J. Cell Biol. 2010, 191, 443-452.
Block, E. Molecular Basis of Mammalian Odor Discrimination: A Status Report. J. Agric. Food Chem. 2018, 66, 13346-13366.
McGann, J.P. Poor human olfaction is a 19th-century myth. Science 2017, 356, eaam7263.
Malnic, B. Searching for the ligands of odorant receptors. Mol. Neurobiol. 2007, 35, 175-181.
De March, C.A.; Yu, Y.; Ni, M.J.; Adipietro, K.A.; Matsunami, H.; Ma, M.; Golebiowski, J. Conserved Residues Control Activation of Mammalian G Protein- Coupled Odorant Receptors. J. Am. Chem. Soc. 2015, 137, 8611-8616.
De March, C.A.; Kim, S.; Antonczak, S.; Goddard, W.A., III; Golebiowski, J. G protein-coupled odorant receptors: From sequence to structure. Protein Sci. 2015, 24, 1543-1548.
Baud, O.; Etter, S.; Spreafico, M.; Bordoli, L.; Schwede, T.; Vogel, H.; Pick, H. The Mouse Eugenol Odorant Receptor: Structural and Functional Plasticity of a Broadly Tuned Odorant Binding Pocket. Biochemistry2011, 50, 843-853.
Man, O.; Gilad, Y.; Lancet, D. Prediction of the odorant binding site of olfactory receptor proteins by human - mouse comparisons. Protein Sci. 2004, 13, 240-254.
Floriano, W.B.; Vaidehi, N.; Goddard, W.A. Making sense of olfaction through predictions of the 3-D structure and function of olfactory receptors. Chem. Senses 2004, 29, 269-290.
Mohrhardt, J.; Nagel, M.; Fleck, D.; Ben-Shaul, Y.; Spehr, M. Signal detection and coding in the accessory olfactory system. Chem. Senses 2018, 43, 667-695.
Brennan, P.A. Pheromones and Mammalian Behavior. In The Neurobiology of Olfaction; Menini, A., Ed.; CRC Press/Taylor & Francis: Abingdon, UK, 2010.
Gomez-Diaz, C.; Benton, R. The joy of sex pheromones. EMBO Rep. 2013, 14, 874-883.
Milardi, D.; Colussi, C.; Grande, G.; Vincenzoni, F.; Pierconti, F.; Mancini, F.; Baroni, S.; Castagnola, M.; Marana, R.; Pontecorvi, A. Olfactory receptors in semen and in the male tract: From proteome to proteins. Front. Endocrinol. 2018, 8, 379.
Olofsson, J.K.; Wilson, D.A. Human Olfaction: It Takes Two Villages. Curr. Biol. 2018, 28, 108-110.
Soudry, Y.; Lemogne, C.; Malinvaud, D.; Consoli, S.M.; Bonfils, P. Olfactory system and emotion: Common substrates. Eur. Ann. Otorhinolaryngol. Head Neck Dis. 2011, 128, 18-23.
Menashe, I.; Abaffy, T.; Hasin, Y.; Goshen, S.; Yahalom, V.; Luetje, C.W.; Lancet, D. Genetic Elucidation of Human Hyperosmia to Isovaleric Acid. PLoS Biol. 2007, 5.
Croy, I.; Olgun, S.; Mueller, L.; Schmidt, A.; Muench, M.; Hummel, C.; Gisselmann, G.; Hatt, H.; Hummel, T. Peripheral adaptive filtering in human olfaction? Three studies on prevalence and effects of olfactory training in specific anosmia in more than 1600 participants. Cortex 2015, 73, 180-187.
Trimmer, C.; Keller, A.; Murphy, N.R.; Snyder, L.L.; Willer, J.R.; Nagai, M.H.; Katsanis, N.; Vosshall, L.B.; Matsunami, H.; Mainland, J.D. Genetic variation across the human olfactory receptor repertoire alters odor perception. Proc. Natl. Acad. Sci. 2019, 16, 9475-9480.
Feng, G.; Zhou, W. Nostril-specific and structure-based olfactory learning of chiral discrimination in human adults. Elife 2019, 8, e41296.
Nagappan, P.G.; Subramaniam, S.; Wang, D.Y. Olfaction as a soldier-- a review of the physiology and its present and future use in the military. Mil. Med. Res. 2017, 4, 9.
Doty, R.L.; Kamath, V. The influences of age on olfaction: A review. Front. Psychol. 2014, 5, 1-20.
Persaud, K.; Dodd, G. Analysis of discrimination mechanisms in the mammalian olfactory system using a model nose. Nature 1982, 299, 352-355.
Pelosi, P.; Zhu, J.; Knoll, W. From Gas Sensors to Biomimetic Artificial Noses. Chemosensors 2018, 6, 32.
Gardner, J.W.; Bartlett, P.N. A brief history of electronic noses. Sens. Actuators B Chem. 1994, 18, 210-211.
Pelosi, P.; Zhu, J.; Knoll, W. Odorant-binding proteins as sensing elements for odour monitoring. Sensors2018, 18, 3248.
Comini, E.; Faglia, G.; Sberveglieri, G.; Pan, Z.; Wang, Z.L. Stable and highly sensitive gas sensors based on semiconducting oxide nanobelts. Appl. Phys. Lett. 2002, 81, 1869-1871.
Wilson, A.D. Review of Electronic-nose Technologies and Algorithms to Detect Hazardous Chemicals in the Environment. Procedia Technol. 2012, 1, 453-463.
Wojnowski, W.; Dymerski, T.; Gębicki, J.; Namieśnik, J. Electronic Noses in Medical Diagnostics. Curr. Med. Chem. 2019, 26, 197-215.
Loutfi, A.; Coradeschi, S.; Mani, G.K.; Shankar, P.; Rayappan, J.B.B. Electronic noses for food quality: A review. J. Food Eng. 2015, 144, 103-111.
Zou, G.; Xiao, Y.; Wang, M.; Zhang, H. Detection of bitterness and astringency of green tea with different taste by electronic nose and tongue. PLoS ONE 2018, 13, e0206517.
Long, Q.; Li, Z.; Han, B.; Gholam Hosseini, H.; Zhou, H.; Wang, S.; Luo, D. Discrimination of Two Cultivars of Alpinia Officinarum Hance Using an Electronic Nose and Gas Chromatography-Mass Spectrometry Coupled with Chemometrics. Sensors 2019, 19, 572.
Chastrette, M.; Cretin, D.; El Aïdi, C. Structure−Odor Relationships: Using Neural Networks in the Estimation of Camphoraceous or Fruity Odors and Olfactory Thresholds of Aliphatic Alcohols. J. Chem. Inf. Comput. Sci. 1996, 36, 108-113.
Cherqaoui, D.; Esseffar, M.; Villemin, D.; Cense, J.-M.; Chastrette, M.; Zakarya, D. Structure-musk odour relationship studies of tetralin and indan compounds using neural networks. New J. Chem. 1998, 22, 839-843.
Wailzer, B.; Klocker, J.; Buchbauer, G.; Ecker, G.; Wolschann, P. Prediction of the Aroma Quality and the Threshold Values of Some Pyrazines Using Artificial Neural Networks. J. Med. Chem. 2001, 44, 2805-2813.
Gabler, S.; Soelter, J.; Hussain, T.; Sachse, S.; Schmuker, M. Physicochemical vs. Vibrational Descriptors for Prediction of Odor Receptor Responses. Mol. Inform. 2013, 32, 855-865.
Lötsch, J.; Kringel, D.; Hummel, T. Machine Learning in Human Olfactory Research. Chem. Senses 2019, 44, 11-22.
Giacalone, D.; Degn, T.K.; Yang, N.; Liu, C.; Fisk, I.; Münchow, M. Common roasting defects in coffee: Aroma composition, sensory characterization and consumer perception. Food Qual. Prefer. 2019, 71, 463-474.
Sáenz-Navajas, M.-P.; Arias, I.; Ferrero-del-Teso, S.; Fernández-Zurbano, P.; Escudero, A.; Ferreira, V. Chemo-sensory approach for the identification of chemical compounds driving green character in red wines. Food Res. Int. 2018, 109, 138-148.