{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T21:12:02Z","timestamp":1761513122202,"version":"build-2065373602"},"reference-count":56,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2012,4,20]],"date-time":"2012-04-20T00:00:00Z","timestamp":1334880000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The Asteraceae, one of the largest families among angiosperms, is chemically characterised by the production of sesquiterpene lactones (SLs). A total of 1,111 SLs, which were extracted from 658 species, 161 genera, 63 subtribes and 15 tribes of Asteraceae, were represented and registered in two dimensions in the SISTEMATX, an in-house software system, and were associated with their botanical sources. The respective 11 block of descriptors: Constitutional, Functional groups, BCUT, Atom-centred, 2D autocorrelations, Topological, Geometrical, RDF, 3D-MoRSE, GETAWAY and WHIM were used as input data to separate the botanical occurrences through self-organising maps. Maps that were generated with each descriptor divided the Asteraceae tribes, with total index values between 66.7% and 83.6%. The analysis of the results shows evident similarities among the Heliantheae, Helenieae and Eupatorieae tribes as well as between the Anthemideae and Inuleae tribes. Those observations are in agreement with systematic classifications that were proposed by Bremer, which use mainly morphological and molecular data, therefore chemical markers partially corroborate with these classifications. The results demonstrate that the atom-centred and RDF descriptors can be used as a tool for taxonomic classification in low hierarchical levels, such as tribes. Descriptors obtained through fragments or by the two-dimensional representation of the SL structures were sufficient to obtain significant results, and better results were not achieved by using descriptors derived from three-dimensional representations of SLs. Such models based on physico-chemical properties can project new design SLs, similar structures from literature or even unreported structures in two-dimensional chemical space. Therefore, the generated SOMs can predict the most probable tribe where a biologically active molecule can be found according Bremer classification.<\/jats:p>","DOI":"10.3390\/molecules17044684","type":"journal-article","created":{"date-parts":[[2012,4,20]],"date-time":"2012-04-20T11:01:48Z","timestamp":1334919708000},"page":"4684-4702","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Self-Organizing Maps of Molecular Descriptors for Sesquiterpene Lactones and Their Application to the Chemotaxonomy of the Asteraceae Family"],"prefix":"10.3390","volume":"17","author":[{"given":"Marcus T.","family":"Scotti","sequence":"first","affiliation":[{"name":"Universidade Federal da Para\u00edba, Departamento de Engenharia e Meio Ambiente, Campus IV, 58297-000, Rio Tinto, PB, Brazil"}]},{"given":"Vicente","family":"Emerenciano","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of S\u00e3o Paulo, Postal Box 26777, S\u00e3o Paulo, 05513-970, Brazil"}]},{"given":"Marcelo J. P.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Universidade Presbiteriana Mackenzie, Cep 01302-907, S\u00e3o Paulo, Brazil"}]},{"given":"Luciana","family":"Scotti","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba, Centro de Biotecnologia, Campus I 50670-910, Jo\u00e3o Pessoa, PB, Brazil"}]},{"given":"Ricardo","family":"Stefani","sequence":"additional","affiliation":[{"name":"Universidade Federal de Mato Grosso, Instituto de Ci\u00eancias Exatas da Terra \u2013 ICET, Rodovia MT-100 Km 3,5, 78698-000, Pontal do Araguaia, MT, Brazil"}]},{"given":"Marcelo S.","family":"Da Silva","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba, Centro de Biotecnologia, Campus I 50670-910, Jo\u00e3o Pessoa, PB, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3588-833X","authenticated-orcid":false,"given":"Francisco Jaime B. Mendon\u00e7a","family":"Junior","sequence":"additional","affiliation":[{"name":"Universidade Estadual da Para\u00edba, Departamento de Ci\u00eancias Biol\u00f3gicas, Laborat\u00f3rio de S\u00edntese e Vetoriza\u00e7\u00e3o de Mol\u00e9culas, 58070-450, Jo\u00e3o Pessoa, PB, Brazil"}]}],"member":"1968","published-online":{"date-parts":[[2012,4,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1007\/BF02919190","article-title":"Sesquiterpene lactones as taxonomic characters in the Asteraceae","volume":"48","author":"Seaman","year":"1982","journal-title":"Bot. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/BF00940593","article-title":"Systematics and evolution within the Compositae, seen with the eyes of a chemist","volume":"171","author":"Zdero","year":"1990","journal-title":"Plant. Syst. Evol."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Harborne, J.B., Mabry, T.J., and Mabry, H. (1975). The Flavonoids, Champman & Hall.","DOI":"10.1007\/978-1-4899-2909-9"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Bohm, B.A., and Stuessy, T.F. (2001). Flavonoids of the Sunflower Family, Springer-Wien.","DOI":"10.1007\/978-3-7091-6181-4"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2335","DOI":"10.1016\/0031-9422(83)80118-6","article-title":"Chromenes and benzofuranes of the Asteraceae, their chemistry and biological significance","volume":"22","author":"Proksch","year":"1983","journal-title":"Phytochemistry"},{"key":"ref_6","unstructured":"Murrray, R.D.H. (1982). The Natural Coumarins. Occurrence,Chemistry and Biochemistry, John Wiley & Sons."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Seaman, F., Bohlmann, F., Zdero, C., and Mabry, T.J. (1990). Diterpenes of Flowering Plants\u2014Compositae (Asteraceae), Springer-Verlag.","DOI":"10.1007\/978-1-4612-3274-2"},{"key":"ref_8","first-page":"139","article-title":"An expert system for structure elucidation of triterpenes","volume":"12","author":"Macari","year":"1994","journal-title":"Spectrosc-Int. J."},{"key":"ref_9","unstructured":"Heywood, V.H., Harborne, J.B., and Turner, B.L. (1977). The Biology and Chemistry of the Compositae I and II, Academic Press."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1111\/j.1756-1051.1992.tb01281.x","article-title":"A review of the phylogeny and classification of Asteraceae","volume":"12","author":"Bremer","year":"1992","journal-title":"Nord. J. Bot."},{"key":"ref_11","unstructured":"Hind, D.J.N., and Beentje, H.J. Compositae: Systematics. Proceedings of the International Compositae Conference I and II."},{"key":"ref_12","unstructured":"Cuvier, G. (1816). Dictionnaire des Sciences Naturelles III, Le Normant."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1111\/j.1095-8339.1873.tb02575.x","article-title":"Notes on the classification, history, and geographical distribution of the Compositae","volume":"13","author":"Bentham","year":"1873","journal-title":"J. Linn. Soc. Bot."},{"key":"ref_14","unstructured":"Engler, A., and Prantl, K. (1890). Die Natiirlichen Pflanzenfamilien, Engelmann."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"465","DOI":"10.5642\/aliso.19760804.10","article-title":"Tribal interrelationships and phylogeny of the Asteraceae","volume":"8","author":"Carlquist","year":"1976","journal-title":"Aliso"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1007\/BF00986129","article-title":"Systematics and phylogeny of the Compositae (Asteraceae)","volume":"125","author":"Wagenitz","year":"1976","journal-title":"Plant. Syst. Evol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1111\/j.1096-0031.1987.tb00509.x","article-title":"Tribal interrelationships of the Asteraceae","volume":"3","author":"Bremer","year":"1987","journal-title":"Cladistics"},{"key":"ref_18","unstructured":"Bremer, K. (1996). Compositae: Systematics, Royal Botanic Garden."},{"key":"ref_19","first-page":"343","article-title":"Everywhere but Antarctica: Using a supertree to understand the diversity and distribution of the Compositae","volume":"55","author":"Funk","year":"2005","journal-title":"Biol. Skr."},{"key":"ref_20","unstructured":"Geissman, T.A., and Crout, D.H.G. (1969). Organic Chemistry of Secondary Plant Metabolism, Freeman Cooper & Company."},{"key":"ref_21","unstructured":"Harborne, J.B. (1988). Ecological Biochemistry, Academic Press."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/S0169-7439(97)00084-1","article-title":"The applications of Bayes theorem in natural products as a guide for skeletons identifications","volume":"40","author":"Emerenciano","year":"1998","journal-title":"Chemometr. Intell. Lab."},{"key":"ref_23","first-page":"125","article-title":"A new methods for grouping chemotaxonomic parameters","volume":"21","author":"Emerenciano","year":"1998","journal-title":"Qu\u00edm. Nova."},{"key":"ref_24","first-page":"277","article-title":"A phylogenetic analysis of tribes of the Asteraceae based on phytochemical data","volume":"2","author":"Calabria","year":"2007","journal-title":"Nat. Prod. Commun."},{"key":"ref_25","first-page":"495","article-title":"Chemical evolution in the Asteraceae. The Oxidation-Reduction mechanism and production of secondary metabolites","volume":"1","author":"Emerenciano","year":"2006","journal-title":"Nat. Prod. Commun."},{"key":"ref_26","unstructured":"Talete, S.R.L. DRAGON for Windows (Software for Molecular Descriptor Calculations).Version 6.0,. Available online:http:\/\/www.talete.mi.it."},{"key":"ref_27","unstructured":"Zupan, J., and Gasteiger, J. (1999). Neural Networks in Chemistry and Drug Design, Wiley-VCH. [2nd]."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Kohonen, T. (2001). Self-Organizing Maps, Springer. [1st].","DOI":"10.1007\/978-3-642-56927-2"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1016\/j.phytochem.2004.12.006","article-title":"Sesquiterpene lactone-based classification of three Asteraceae tribes: A study based on self-organizing neural networks applied to chemo systematics","volume":"66","author":"Terfloth","year":"2005","journal-title":"Phytochemistry"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1021\/ci060046x","article-title":"Sesquiterpene lactones-based classification of the family Asteraceae using neural networks and k-nearest neighbors","volume":"47","author":"Hristozov","year":"2007","journal-title":"J. Chem. Inf. Model."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Todeschini, R., and Consonni, V. (2009). Molecular Descriptors for Chemoinformatics, Wiley-VCH.","DOI":"10.1002\/9783527628766"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2487","DOI":"10.1016\/j.bmc.2005.11.027","article-title":"Sesquiterpene lactones as inhibitors of IL-8 expression in HeLa cells","volume":"14","author":"Lindenmeyer","year":"2006","journal-title":"Bioorgan. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2241","DOI":"10.1021\/jm051125n","article-title":"Development of a structural model for NF-kappa B inhibition of sesquiterpene lactones using self-organizing neural networks","volume":"49","author":"Wagner","year":"2006","journal-title":"J. Med. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.foodchem.2007.03.038","article-title":"Quantitative elucidation of the structure-bitterness relationship of cynaropicrin and grosheimin derivatives","volume":"105","author":"Scotti","year":"2007","journal-title":"Food Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2927","DOI":"10.1016\/j.bmc.2007.02.005","article-title":"Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity","volume":"15","author":"Scotti","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2197","DOI":"10.1016\/j.ejmech.2008.01.003","article-title":"Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones","volume":"43","author":"Fernandes","year":"2008","journal-title":"Eur. J. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2062","DOI":"10.3390\/molecules14062062","article-title":"Quantitative Structure - Antiprotozoal Activity Relationships of Sesquiterpene Lactones","volume":"14","author":"Schmidt","year":"2009","journal-title":"Molecules"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1002\/qua.21647","article-title":"Structure-Hepatoprotective Activity Relationship Study of Sesquiterpene Lactones: A QSAR Analysis","volume":"109","author":"Paukku","year":"2009","journal-title":"Int. J. Quantum. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"44","DOI":"10.2174\/157018011793663868","article-title":"Volsurf Descriptors to Analyse Anti-HCV and Cytotoxic Activities of Sesquiterpene Lactones from Asteraceae Family","volume":"8","author":"Fernandes","year":"2011","journal-title":"Lett. Drug Des Discov."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1021\/np049655u","article-title":"Expanding the ChemGPS Chemical Space with Natural Products","volume":"68","author":"Larsson","year":"2005","journal-title":"J. Nat. Prod."},{"key":"ref_41","first-page":"10","article-title":"A intelig\u00eancia artificial aplicada \u00e0 qu\u00edmica de produtos naturais. O programa Sistemat. Parte I - Bases Te\u00f3ricas","volume":"13","author":"Gastmans","year":"1990","journal-title":"Qu\u00edm. Nova"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1030","DOI":"10.1021\/ci960343+","article-title":"Chemical information in 3D space","volume":"36","author":"Gasteiger","year":"1996","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref_43","unstructured":"(Hyperchem Program Release 8.0 for Windows, 2009). Hyperchem Program Release 8.0 for Windows."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3902","DOI":"10.1021\/ja00299a024","article-title":"AM1: A new general purpose quantum mechanical molecular model","volume":"107","author":"Dewar","year":"1985","journal-title":"J. Am. Chem. Soc."},{"key":"ref_45","unstructured":"Leach, A.R. (2001). Molecular Modelling: Principles and Applications, Prentice Hall."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1093\/biomet\/37.1-2.17","article-title":"Notes on Continuous Stochastic Phenomena","volume":"37","author":"Moran","year":"1950","journal-title":"Biometrika"},{"key":"ref_47","first-page":"359","article-title":"The auto-correlation of a topological-structure\u2014A new molecular descriptor","volume":"4","author":"Moreau","year":"1980","journal-title":"New. J. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1021\/ci00023a019","article-title":"Molecular Topology. 15. 3D Distance Matrices and Related Topological Indexes","volume":"35","author":"Diudea","year":"1995","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1021\/ci960168x","article-title":"From chemical topology to 3D geometry","volume":"37","author":"Balaban","year":"1997","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1002\/qsar.19970160203","article-title":"3D-modelling and prediction by WHIM descriptors. 5. Theory development and chemical meaning of WHIM descriptors","volume":"16","author":"Todeschini","year":"1997","journal-title":"Quant. Struct-act. Rel."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1002\/qsar.19970160204","article-title":"3D-modelling and prediction by WHIM descriptors. 6. Application of WHIM descriptors in QSAR studies P","volume":"16","author":"Todeschini","year":"1997","journal-title":"Quant. Struct-act. Rel."},{"key":"ref_52","unstructured":"Talete, S.R.L. Mobydigs Academic version - Version 1.1. Available online:http:\/\/www.talete.mi.it."},{"key":"ref_53","unstructured":"Leardi, R. (2004). Nature-Inspired Methods in Chemometrics: Genetic Algorithms and Artificial Neural Networks, Elsevier."},{"key":"ref_54","unstructured":"Available online:http:\/\/www.mathworks.com."},{"key":"ref_55","unstructured":"Vesanto, J., Himberg, J., Alhoniemi, E., and Parhankangas, J. SOM Toolbox for Matlab 5. Available online:http:\/\/www.cis.hut.fi\/projects\/somtoolbox."},{"key":"ref_56","first-page":"54","article-title":"Self-Organizing Map for Data Mining in MATLAB: the SOM Toolbox","volume":"25","author":"Vesanto","year":"1999","journal-title":"Simulation News Europe"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/4\/4684\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:49:54Z","timestamp":1760219394000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/4\/4684"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,4,20]]},"references-count":56,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2012,4]]}},"alternative-id":["molecules17044684"],"URL":"https:\/\/doi.org\/10.3390\/molecules17044684","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2012,4,20]]}}}