Quantitative structure–activity relationships to predict sweet and non-sweet tastes

Theoretical Chemistry Accounts

Volumn 135, Issue 3, 2016, Pages 1-13

  Rojas, Cristian ^a,b   Ballabio, Davide ^c   Consonni, Viviana ^c   Tripaldi, Piercosimo ^b   Mauri, Andrea ^c   Todeschini, Roberto ^c  

^a INSTITUTO DE INVESTIGACIONES FISICOQUÍMICAS TEÓRICAS Y APLICADAS INIFTA   (Argentina)

^b UNIVERSIDAD DEL AZUAY   (Ecuador)

^c UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

Classification; k Nearest neighbors; QSAR; Sweetness

Indexed keywords

EID: 84959324876     PISSN: 1432881X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00214-016-1812-1     Document Type: Article

References (87)

1. Shallenberger RS (1993) Taste chemistry. Springer Science & Business Media, Berlin
2. Hugot E, Jenkins GH (1972) Handbook of cane sugar engineering, vol 114. Elsevier, Philadelphia
3. Asadi M (2006) Beet-sugar handbook. Wiley, NewYork
4. Birch GG (1999) Modulation of sweet taste. BioFactors 9(1):73–80
5. deMan JM (1999) Principles of food chemistry, 3rd edn. Berlin, Springer
6. Oertly E, Myers RG (1919) A new theory relating constitution to taste. Simple relations between the constitution of aliphatic compounds and their sweet taste. J Am Chem Soc 41(6):855–867
7. Shallenberger RS, Acree TE (1967) Molecular theory of sweet taste. Nature 216:480–482
8. Kier LB (1972) A molecular theory of sweet taste. J Pharm Sci 61(9):1394–1397
9. Nofre C, Tinti J-M (1996) Sweetness reception in man: the multipoint attachment theory. Food Chem 56(3):263–274
10. Ellis JW (1995) Overview of sweeteners. J Chem Educ 72(8):671
11. Katritzky AR, Lobanov VS, Karelson M (1995) QSPR: the correlation and quantitative prediction of chemical and physical properties from structure. Chem Soc Rev 24:279–287
12. Trinajstic N (1992) Chemical graph theory. CRC Press, Boca Raton
13. Diudea MV (2001) QSPR/QSAR studies by molecular descriptors. Nova Science Publishers, New York
14. Todeschini R, Consonni V (2009) Molecular descriptors for chemoinformatics, vol 2. Wiley-VCH, Weinheim
15. Iwamura H (1980) Structure-taste relationship of perillartine and nitro-and cyanoaniline derivatives. J Med Chem 23(3):308–312
16. van der Wel H, van der Heijden A, Peer H (1987) Sweeteners. Food Rev Int 3(3):193–268
17. Kier LB (1980) Molecular structure influencing either a sweet or bitter taste among aldoximes. J Pharm Sci 69(4):416–419
18. Takahashi Y, Miyashita Y, Tanaka Y, Abe H, Sasaki S (1982) A consideration for structure-taste correlations of perillartines using pattern-recognition techniques. J Med Chem 25(10):1245–1248
19. Takahashi Y, Abe H, Miyashita Y, Tanaka Y, Hayasaka H, Sasaki SI (1984) Discriminative structural analysis using pattern recognition techniques in the structure-taste problem of perillartines. J Pharm Sci 73(6):737–741
20. Miyashita Y, Takahashi Y, Takayama C, Ohkubo T, Funatsu K, Sasaki S-I (1986) Computer-assisted structure/taste studies on sulfamates by pattern recognition methods. Anal Chim Acta 184:143–149
21. Miyashita Y, Takahashi Y, Takayama C, Sumi K, Nakatsuka K, Ohkubo T, Abe H, Sasaki S (1986) Structure-taste correlation of L-aspartyl dipeptides using the SIMCA method. J Med Chem 29(6):906–912
22. Okuyama T, Miyashita Y, Kanaya S, Katsumi H, S-i Sasaki, Randić M (1988) Computer assisted structure-taste studies on sulfamates by pattern recognition method using graph theoretical invariants. J Comput Chem 9(6):636–646
23. −) sweeteners-the role of R. J Pharm Sci 70(8):933–935
24. Spillane WJ, McGlinchey G, Muircheartaigh IÓ, Benson GA (1983) Structure-activity studies on sulfamate sweetners III: structure-taste relationships for heterosulfamates. J Pharm Sci 72(8):852–856
25. −) sweeteners. J Chem Soc, Perkin Trans 2(7):741–746
26. −). Phosphorus Sulfur Silicon Relat Elem 59(1–4):255–258
27. Spillane WJ, Sheahan MB, Ryder CA (1993) Synthesis and taste properties of sodium disubstituted phenylsulfamates. Structure-taste relationships for sweet and bitter/sweet sulfamates. Food Chem 47(4):363–369
28. 3Na: distinction between sweet, sweet-bitter, and bitter molecules. J Agric Food Chem 46(8):3016–3026
29. Spillane WJ, Ryder CA, Curran PJ, Wall SN, Kelly LM, Feeney BG, Newell J (2000) Development of structure-taste relationships for sweet and non-sweet heterosulfamates. J Chem Soc Perkin Trans 2(7):1369–1374
30. Spillane WJ, Feeney BG, Coyle CM (2002) Further studies on the synthesis and tastes of monosubstituted benzenesulfamates. A semi-quantitative structure-taste relationship for the meta-compounds. Food Chem 79(1):15–22
31. Spillane WJ, Kelly LM, Feeney BG, Drew MG, Hattotuwagama CK (2003) Synthesis of heterosulfamates. Search for structure-taste relationships. Arkivoc 7:297–309
32. Kelly DP, Spillane WJ, Newell J (2005) Development of structure-taste relationships for monosubstituted phenylsulfamate sweeteners using classification and regression tree (CART) analysis. J Agric Food Chem 53(17):6750–6758
33. Spillane WJ, Kelly DP, Curran PJ, Feeney BG (2006) Structure-taste relationships for disubstituted phenylsulfamate tastants using classification and regression tree (CART) Analysis. J Agric Food Chem 54(16):5996–6004
34. Spillane WJ, Coyle CM, Feeney BG, Thompson EF (2009) Development of structure-taste relationships for thiazolyl-, benzothiazolyl-, and thiadiazolylsulfamates. J Agric Food Chem 57(12):5486–5493
35. Spillane WJ (1993) Structure taste studies of sulphamates. In: Mathlouthi M, Kanters JA, Birch GG (eds) Sweet-taste chemoreception. Elsevier Science Publishers, Philadelphia, p 283
36. Spillane WJ, Ryder CA, Walsh MR, Curran PJ, Concagh DG, Wall SN (1996) Sulfamate sweeteners. Food Chem 56(3):255–261
37. Walters DE (2006) Analysing and predicting properties of sweet-tasting compounds. In: Spillane WJ (ed) Optimising sweet taste in foods. pp 283–291
38. Rojas C, Duchowicz PR, Pis Diez R, Tripaldi P (2016) Applications of quantitative structure-relative sweetness relationships in food chemistry. In: Mercader AG, Duchowicz PR, Sivakumar PM (eds) Chemometrics applications and research: QSAR in medicinal chemistry. CRC Press, Taylor & Francis Group, pp 317–339
39. van der Heijden A (1997) Historical overview on structure-activity relationships among sweeteners. Pure Appl Chem 69(4):667–674
40. Spillane W, Malaubier J-B (2014) Sulfamic acid and its N-and O-substituted derivatives. Chem Rev 114(4):2507–2586
41. Organisation for Economic Co-operation and Development (2007) Guidance document on the validation of (quantitative)structure-activity relationships [(Q)SAR] models. OECD Publishing, Paris
42. Arnoldi A, Bassoli A, Borgonovo G, Drew MG, Merlini L, Morini G (1998) Sweet isovanillyl derivatives: synthesis and structure-taste relationships of conformationally restricted analogues. J Agric Food Chem 46(10):4002–4010
43. Arnoldi A, Bassoli A, Borgonovo G, Merlini L (1995) Synthesis and sweet taste of optically active (−)-haematoxylin and of some (±)-haematoxylin derivatives. J Chem Soc Perkin Trans 1(19):2447–2453
44. Arnoldi A, Bassoli A, Borgonovo G, Merlini L, Morini G (1997) Synthesis and structure-activity relationships of sweet 2-benzoylbenzoic acid derivatives. J Agric Food Chem 45(6):2047–2054
45. Arnoldi A, Bassoli A, Merlini L (1996) Progress in isovanillyl sweet compounds. Food Chem 56(3):247–253
46. Arnoldi A, Bassoli A, Merlini L, Ragg E (1991) Isovanillyl sweeteners. Synthesis, conformational analysis, and structure-activity relationship of some sweet oxygen heterocycles. J Chem Soc Perkin Trans 2(9):1399–1406
47. Arnoldi A, Bassoli A, Merlini L, Ragg E (1993) Isovanillyl sweeteners. Synthesis and sweet taste of sulfur heterocycles. J Chem Soc Perkin Trans 1(12):1359–1366
48. Bassoli A, Borgonovo G, Drew MG, Merlini L (2000) Enantiodifferentiation in taste perception of isovanillic derivatives. Tetrahedron Asymmetry 11(15):3177–3186
49. Bassoli A, Drew MGB, Hattotuwagama CK, Merlini L, Morini G, Wilden GRH (2001) Quantitative structure-activity relationships of sweet isovanillyl derivatives. Quant Struct-Act Relat 20(1):3–16
50. Belitz H-D, Grosch W, Schieberle P (2009) Food chemistry, 4th edn. Springer-Verlag, Heidelberg
51. Nanayakkara NPD, Hussain RA, Pezzuto JM, Soejarto DD, Kinghorn AD (1988) An intensely sweet dihydroflavonol derivative based on a natural product lead compound. J Med Chem 31(6):1250–1253
52. O’Brien-Nabors L (2001) Alternative sweeteners, 3rd edn. New York, Marcel Dekker Inc
53. Yamato M, Hashigaki K (1979) Chemical structure and sweet taste of isocoumarins and related compounds. Chem Senses 4(1):35–47
54. Yang X, Chong Y, Yan A, Chen J (2011) In-silico prediction of sweetness of sugars and sweeteners. Food Chem 128(3):653–658
55. Zhong M, Chong Y, Nie X, Yan A, Yuan Q (2013) Prediction of sweetness by multilinear regression analysis and support vector machine. J Food Sci 78(9):S1445–S1450
56. Paulus K, Reisch AM (1980) The influence of temperature on the threshold values of primary tastes. Chem Senses 5(1):11–21
57. Open Babel, Open Babel: The Open Source Chemistry Toolbox. http://openbabel.org/
58. Berthold M, Cebron N, Dill F, Gabriel T, Kötter T, Meinl T, Ohl P, Sieb C, Thiel K, Wiswedel B (2008) KNIME: the konstanz information miner. In: Preisach C, Burkhardt H, Schmidt-Thieme L, Decker R (eds) Data analysis, machine learning and applications. Studies in classification, data analysis, and knowledge organization. Springer, Berlin Heidelberg, pp 319–326
59. Hypercube, Inc., HyperChem. http://www.hyper.com
60. TALETE, srl., Dragon (version 6) (2015). Software for Molecular Descriptor Calculation, http://www.talete.mi.it/
61. Pearlman RS (1993) 3D molecular structures: generation and use in 3D searching. In: Kubinyi H (ed) 3D QSAR in drug design. Theory and applications, Springer Science & Business Media, pp 41–79
62. Doweyko AM (2004) 3D-QSAR illusions. J Comput Aided Mol Des 18(7–9):587–596
63. Hechinger M, Leonhard K, Marquardt W (2012) What is wrong with quantitative structure-property relations models based on three-dimensional descriptors? J Chem Inf Model 52(8):1984–1993
64. Kowalski B, Bender C (1972) k-Nearest neighbor classification rule (pattern recognition) applied to nuclear magnetic resonance spectral interpretation. Anal Chem 44(8):1405–1411
65. Ballabio D, Consonni V, Mauri A, Claeys-Bruno M, Sergent M, Todeschini R (2014) A novel variable reduction method adapted from space-filling designs. Chemometr Intell Lab Syst 136:147–154
66. Leardi R, Gonzalez AL (1998) Genetic algorithms applied to feature selection in PLS regression: how and when to use them. Chemometr Intell Lab Syst 41(2):195–207
67. Ballabio D, Consonni V (2013) Classification tools in chemistry. Part 1: linear models. PLS-DA. Anal Methods 5(16):3790–3798
68. Wold S, Esbensen K, Geladi P (1987) Principal component analysis. Chemometr Intell Lab Syst 2(1):37–52
69. Jolliffe IT (1986) Principal component analysis. Springer Science + Business Media, Berlin
70. Krzanowski W (1988) Principles of multivariate analysis: a user’s perspective. Oxford University Press, Oxford
71. Bro R, Smilde AK (2014) Principal component analysis. Anal Methods 6(9):2812–2831
72. Sahigara F, Mansouri K, Ballabio D, Mauri A, Consonni V, Todeschini R (2012) Comparison of different approaches to define the applicability domain of QSAR models. Molecules 17(5):4791–4810
73. Sahigara F, Ballabio D, Todeschini R, Consonni V (2013) Defining a novel k-nearest neighbours approach to assess the applicability domain of a QSAR model for reliable predictions. J Cheminfor 5:27
74. Cassotti M, Consonni V, Mauri A, Ballabio D (2014) Validation and extension of a similarity-based approach for prediction of acute aquatic toxicity towards Daphnia magna. SAR QSAR Environ Res 25(12):1013–1036
75. Cassotti M, Ballabio D, Consonni V, Mauri A, Tetko IV, Todeschini R (2014) Prediction of acute aquatic toxicity toward Daphnia magna by using the GA-kNN method. Altern Lab Anim 42:31–41
76. Cassotti M, Ballabio D, Todeschini R, Consonni V (2015) A similarity-based QSAR model for predicting acute toxicity towards the fathead minnow (Pimephales promelas). SAR QSAR Environ Res 26(3):217–243
77. Ballabio D (2015) A MATLAB toolbox for principal component analysis and unsupervised exploration of data structure. Chemometr Intell Lab Syst 149:1–9
78. MathWorks: Natick, MatLab (version 7.13.0.564) (2011). http://www.mathworks.com
79. Carhart RE, Smith DH, Venkataraghavan R (1985) Atom pairs as molecular features in structure-activity studies: definition and applications. J Chem Inf Comput Sci 25(2):64–73
80. Birch GG, Karim R, Lopez A (1994) Novel aspects of structure-activity relationships in sweet taste chemoreception. Food Qual Prefer 5(1):87–93
81. Rojas C, Tripaldi P, Duchowicz PR (2016) A new QSPR study on relative sweetness. Int J Quant Struct Prop Relatsh 1(1):76–90
82. Ghose AK, Viswanadhan VN, Wendoloski JJ (1998) Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: an analysis of ALOGP and CLOGP methods. J Phys Chem A 102(21):3762–3772
83. Baek N-I, Chung M-S, Shamon L, Kardono LBS, Tsauri S, Padmawinata K, Pezzuto JM, Soejarto DD, Kinghorn AD (1993) Selligueain A, a novel highly sweet proanthocyanidin from the rhizomes of Selliguea feei. J Nat Prod 56(9):1532–1538
84. Birch GG (1987) Sweetness and sweeteners. Endeavour 11(1):21–24
85. Birch G, Mylvaganam A (1976) Evidence for the proximity of sweet and bitter receptor sites. Nature 260:632–634
86. van der Heijden A, van der Wel H, Peer HG (1985) Structure-activity relationships in sweeteners. I. Nitroanilines, sulphamates, oximes, isocoumarins and dipeptides. Chem Senses 10(1):57–72
87. Katritzky AR, Petrukhin R, Perumal S, Karelson M, Prakash I, Desai N (2002) A QSPR study of sweetness potency using the CODESSA program. Croat Chem Acta 75(2):475–502