Self-organizing maps of molecular descriptors for sesquiterpene lactones and their application to the chemotaxonomy of the Asteraceae family

Molecules

Volumn 17, Issue 4, 2012, Pages 4684-4702

  Scotti, Marcus T ^a   Emerenciano, Vicente ^b   Ferreira, Marcelo J P ^c   Scotti, Luciana ^a   Stefani, Ricardo ^d   Da Silva, Marcelo S ^a   Mendonça Jr , Francisco Jaime B ^e  

^a FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c MACKENZIE PRESBYTERIAN UNIVERSITY   (Brazil)

^d FEDERAL UNIVERSITY OF MATO GROSSO   (Brazil)

^e STATE UNIVERSITY OF PARAÍBA   (Brazil)

Author keywords

Astearaceae; Chemotaxonomy; Sesquiterpene lactones

Indexed keywords

LACTONE; SESQUITERPENE;

ARTICLE; ASTERACEAE; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; GENETICS; OXIDATION REDUCTION REACTION; PHYLOGENY;

ASTERACEAE; LACTONES; MODELS, MOLECULAR; OXIDATION-REDUCTION; PHYLOGENY; SESQUITERPENES;

EID: 84860253170     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17044684     Document Type: Article

References (56)

1. Seaman, F.C. Sesquiterpene lactones as taxonomic characters in the Asteraceae. Bot. Rev. 1982, 48, 123-551.
2. Zdero, C.; Bohlmann, F. Systematics and evolution within the Compositae, seen with the eyes of a chemist. Plant. Syst. Evol. 1990, 171, 1-14.
3. Harborne, J.B.; Mabry, T.J.; Mabry, H. The Flavonoids; Champman & Hall: London, UK, 1975.
4. Bohm, B.A.; Stuessy, T.F. Flavonoids of the Sunflower Family; Springer-Wien: New York, NY, USA, 2001.
5. Proksch, P.; Rodriguez, E. Chromenes and benzofuranes of the Asteraceae, their chemistry and biological significance. Phytochemistry 1983, 22, 2335-2348.
6. Murrray, R.D.H. The Natural Coumarins. Occurrence, Chemistry and Biochemistry; John Wiley & Sons: New York, NY, USA, 1982.
7. Seaman, F.; Bohlmann, F.; Zdero, C.; Mabry, T.J. Diterpenes of Flowering Plants-Compositae (Asteraceae); Springer-Verlag: New York, NY, USA, 1990.
8. Macari, P.A.T.; Gastmans, J.P.; Rodriguez, G.V.; Emerenciano, V.P. An expert system for structure elucidation of triterpenes. Spectrosc-Int. J. 1994, 12, 139-166.
9. Heywood, V.H.; Harborne, J.B.; Turner, B.L. The Biology and Chemistry of the Compositae I and II; Academic Press: New York, NY, USA, 1977.
10. Bremer, K.; Jansen, R.K.; Karis, P.O.; Kallersjo, M.; Keeley, S.C.; Kim, K.J.; Michaels, H.J.; Palmer, J.D.; Wallace, R.S. A review of the phylogeny and classification of Asteraceae. Nord. J. Bot. 1992, 12, 141-148.
11. Hind, D.J.N.; Beentje, H.J. Compositae: Systematics. Proceedings of the International Compositae Conference I and II; Royal Botanic Gardens: Kew, Australia, 1994.
12. Cassini, H. Tableau exprimant les affinities des tribus naturelles de famile des Synanthérées. In Dictionnaire des Sciences Naturelles III; Cuvier, G. Ed.; Le Normant: Paris, France, 1816.
13. Bentham, G. Notes on the classification, history, and geographical distribution of the Compositae. J. Linn. Soc. Bot. 1873, 13, 335-557.
14. Hoffman, O. Compositae. In Die Natiirlichen Pflanzenfamilien; Engler, A., Prantl, K., Eds.; Engelmann: Leipzig, Germany, 1890.
15. Carlquist, S. Tribal interrelationships and phylogeny of the Asteraceae. Aliso 1976, 8, 465-492.
16. Wagenitz, G. Systematics and phylogeny of the Compositae (Asteraceae). Plant. Syst. Evol. 1976, 125, 29-46.
17. Bremer, K. Tribal interrelationships of the Asteraceae. Cladistics 1987, 3, 210-253.
18. Bremer, K. Major clades and grades of the Asteraceae. In Compositae: Systematics; Royal Botanic Garden: Kew, Australia, 1996.
19. Funk, V.; Bayer, R.J.; Keeley, S.; Chan, R.; Watson, L.; Gemeinholzer, B.; Schilling, E.; Panero, J.L.; Baldwin, B.G.; Garcia-Jacas, N.; Susanna, A.; Jansen, R.K. Everywhere but Antarctica: Using a supertree to understand the diversity and distribution of the Compositae. Biol. Skr. 2005, 55, 343-374.
20. Geissman, T.A.; Crout, D.H.G. Organic Chemistry of Secondary Plant Metabolism; Freeman Cooper & Company: San Francisco, CA, USA, 1969.
21. Harborne, J.B. Ecological Biochemistry; Academic Press: London, UK, 1988.
22. Emerenciano, V.P.; Ferreira, M.J.P.; Branco, M.D.; Dubois, J.E. The applications of Bayes theorem in natural products as a guide for skeletons identifications. Chemometr. Intell. Lab. 1998, 40, 83-92.
23. Emerenciano, V.P.; Rodrigues, G.V.; Alvarenga, S.A.V.; Macari, P.A.T.; Kaplan, M.A.C. A new methods for grouping chemotaxonomic parameters. Quím. Nova. 1998, 21, 125-129.
24. Calabria, L.M.; Emerenciano, V.P.; Ferreira, M.J.P.; Scotti, M.T.; Mabry, T.J. A phylogenetic analysis of tribes of the Asteraceae based on phytochemical data. Nat. Prod. Commun. 2007, 2, 277-285.
25. Emerenciano, V.P.; Cabrol-Bass, D.; Ferreira, M.J.P.; Alvarenga, S.A.; Brant, A.J.C.; Scotti, M.T.; Barbosa, K.O. Chemical evolution in the Asteraceae. The Oxidation-Reduction mechanism and production of secondary metabolites. Nat. Prod. Commun. 2006, 1, 495-507.
26. Talete, S.R.L. DRAGON for Windows (Software for Molecular Descriptor Calculations).Version 6.0, 2011. Available online: http://www.talete.mi.it (accessed on 30 May 2011).
27. Zupan, J.; Gasteiger, J. Neural Networks in Chemistry and Drug Design, 2nd ed.; Wiley-VCH: Weinheim, Germany, 1999.
28. Kohonen, T. Self-Organizing Maps, 1st ed.; Springer: Berlin, Germany, 2001.
29. Da Costa, F.B.; Terfloth, L.; Gasteiger, J. Sesquiterpene lactone-based classification of three Asteraceae tribes: A study based on self-organizing neural networks applied to chemo systematics. Phytochemistry 2005, 66, 345-353.
30. Hristozov, D.; Da Costa, F.B.; Gasteiger, J. Sesquiterpene lactones-based classification of the family Asteraceae using neural networks and k-nearest neighbors. J. Chem. Inf. Model. 2007, 47, 9-19.
31. Todeschini, R.; Consonni, V. Molecular Descriptors for Chemoinformatics; Wiley-VCH: Weinheim, Germany, 2009.
32. Lindenmeyer, M.T.; Hrenn, A.; Kern, C.; Castro, V.; Murillo, R.; Muller, S.; Schulte-Mönting, J.; Siedle, B.; Merfort, I. Sesquiterpene lactones as inhibitors of IL-8 expression in HeLa cells. Bioorgan. Med. Chem. 2006, 14, 2487-2497.
33. Wagner, S.; Hofmann, A.; Siedle, B.; Terfloth, L.; Merfort, I.; Gasteiger, J. Development of a structural model for NF-kappa B inhibition of sesquiterpene lactones using self-organizing neural networks. J. Med. Chem. 2006, 49, 2241-2252.
34. Scotti, L.; Scotti, M.T.; Ishiki, H.M.; Ferreira M.J.P.; Emerenciano, V.P.; Menezes, C.M.D.; Ferreira, E.I. Quantitative elucidation of the structure-bitterness relationship of cynaropicrin and grosheimin derivatives. Food Chem. 2007, 105, 77-83.
35. Scotti M.T.; Fernandes, M.B.; Ferreira, M.J.P.; Emerenciano, V.P. Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity. Bioorg. Med. Chem. 2007, 15, 2927-2934.
36. Fernandes, M.B.; Scotti, M.T.; Ferreira, M.J.P.; Emerenciano, V.P. Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones. Eur. J. Med. Chem. 2008, 43, 2197-2205.
37. Schmidt, T.J.; Nour, A.M.M.; Khalid, S.A.; Kaiser, M.; Brun, R. Quantitative Structure-Antiprotozoal Activity Relationships of Sesquiterpene Lactones. Molecules 2009, 14, 2062-2076.
38. Paukku, Y.; Rasulev, B.; Syrov, V.; Khushbaktova, Z.; Leszczynski, J. Structure-Hepatoprotective Activity Relationship Study of Sesquiterpene Lactones: A QSAR Analysis. Int. J. Quantum. Chem. 2009, 109, 17-27.
39. Fernandes, M.B.; Rossini, M.; Stefani, R.; Tavares, L.; Emerenciano, V.D.; Scotti, L.; Scotti, M.T. Volsurf Descriptors to Analyse Anti-HCV and Cytotoxic Activities of Sesquiterpene Lactones from Asteraceae Family. Lett. Drug Des Discov. 2011, 8, 44-58.
40. Larsson, J.; Gottfries, J.; Bohlin, L.; Backlund, A. Expanding the ChemGPS Chemical Space with Natural Products. J. Nat. Prod. 2005, 68, 985-991.
41. Gastmans, J.P.; Furlan, M.; Lopes, M.N.; Borges, J.H.G.; Emerenciano, V.P. A inteliĝncia artificial aplicada à química de produtos naturais. O programa Sistemat. Parte I-Bases Teóricas. Quím. Nova 1990, 13, 10-15.
42. Gasteiger, J.; Sadowski, J.; Schuur, J.; Selzer, P.; Steinhauer, L.; Steinhauer, V. Chemical information in 3D space. J. Chem. Inf. Comput. Sci. 1996, 36, 1030-1037.
43. Hyperchem Program Release 8.0 for Windows. Hybercube, Inc.: Gainesville, FL, USA, 2009.
44. Dewar, M.J.S.E.; Zoebisch, G.; Healy, E.F.; Stewart J.J.P. AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
45. Leach, A.R. Molecular Modelling: Principles and Applications; Prentice Hall: London, UK, 2001.
46. Moran, P.A.P. Notes on Continuous Stochastic Phenomena. Biometrika 1950, 37, 17-23.
47. Moreau, G.; Broto, P. The auto-correlation of a topological-structure-A new molecular descriptor. New. J. Chem. 1980, 4, 359-360.
48. Diudea, M.V.; Horvath, D.; Graovac, A. Molecular Topology. 15. 3D Distance Matrices and Related Topological Indexes. J. Chem. Inf. Comput. Sci. 1995, 35, 129-135.
49. Balaban, A.T. From chemical topology to 3D geometry. J. Chem. Inf. Comput. Sci. 1997, 37, 645-650.
50. Todeschini, R.; Gramatica, P. 3D-modelling and prediction by WHIM descriptors. 5. Theory development and chemical meaning of WHIM descriptors. Quant. Struct-act. Rel. 1997, 16, 113-119.
51. Todeschini, R.; Gramatica, P. 3D-modelling and prediction by WHIM descriptors. 6. Application of WHIM descriptors in QSAR studies P. Quant. Struct-act. Rel.1997, 16, 120-125.
52. Talete, S.R.L. Mobydigs Academic version-Version 1.1, 2010. Available online: http://www.talete.mi.it (accessed on 30 May 2011).
53. Todeschini, R.; Mauri, A.; Pavan, M. MobyDigs: Sofwtare for Regression and Classification Models by Genetic Algorithms. In Nature-Inspired Methods in Chemometrics: Genetic Algorithms and Artificial Neural Networks; Leardi, R., Eds.; Elsevier: Genova, Italy, 2004.
54. Mathworks Inc. 2004. Available online: http://www.mathworks.com (accessed on 30 May 2011).
55. Vesanto, J.; Himberg, J.; Alhoniemi, E.; Parhankangas, J. SOM Toolbox for Matlab 5, 2005. Available online: http://www.cis.hut.fi/projects/somtoolbox (accessed on 30 May 2011).
56. Vesanto, J.; Alhoniemi, E.; Himberg, J.; Kiviluoto, K.; Parviainen, J. Self-Organizing Map for Data Mining in MATLAB: the SOM Toolbox. Simulation News Europe 1999, 25, 54.