Automatic structure elucidation through data base search and 2D NMR spectral analysis

Natural Product Communications

Volumn 1, Issue 1, 2006, Pages 57-64

  Nuzillard, Jean Marc ^a   De Paulo Emerenciano, Vicente ^b  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

2D NMR; Chemical databases; Expert systems; LSD; SISTEMAT; Structure elucidation

Indexed keywords

EID: 84900462273     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0600100111     Document Type: Article

References (43)

1. Carhart RE, Smith DH, Gray NAB, Nourse JG, Djerassi C. (1981) GENOA: A Computer Program for Structure Elucidation Utilizing Overlapping and alternative Substructures. Journal of Organic Chemistry, 46, 1708-1718.
2. Dubois JE, Carabedian M, Dagane I. (1984) Computer-aided elucidation of structures by carbon-13 nuclear magnetic resonance. Analytica Chimica Acta, 158, 217-233.
3. Carabedian M, Dagane I, Dubois JE. (1988) Elucidation by Progressive Intersection of Substructures from Carbon-13 Nuclear Magnetic Resonance. Analytical Chemistry, 60, 2186-2192.
4. Shelley CA, Munk ME. (1981) . CASE, a computer model of the structure elucidation process. Analytica Chimica Acta, 133, 507-516.
5. Christie BD, Munk ME. (1991) The Role of Two-dimensional Nuclear Magnetic Resonance Spectroscopy in Computer-Enhanced Structure Elucidation. Journal of the American Chemical Society, 113, 3750-3757.
6. Bremser W, Grzonka M. (1991) SpecInfo-A Multidimensional Spectroscopic Interpretation System. Mikrochimica Acta, 2, 483-491.
7. Will M, Fachinger W, Richert JR. (1996) Fully Automated Structure Elucidation - A Spectrocopist's Dream Comes True. Journal of Chemical Information and Computer Science, 36, 221-227.
8. Funatsu K, Miyabayashi N, Sasaki S. (1988) Further development of structure generation in the Automated Structure Elucidation System CHEMICS. Journal of Chemical Information and Computer Science, 28, 18-28.
9. Funatsu K, Susuta Y, Sasaki S. (1989) Introduction of Two-Dimensional NMR Spectral Infornation to an Automated Structure Elucidation System, CHEMICS. Journal of Chemical Information and Computer Science, 29, 6-11.
10. Peng C, Yuan S, Zheng C, Hui Y. (1994) Efficient Application of 2D NMR Correlation Information in Computer-Assisted Structure Elucidation of Complex Natural Products. Journal of Chemical Information and Computer Science, 34, 805-813
11. Lindel T, Junker J, Köck M. (1997) Cocon: From NMR Correlation Data to Molecular Constitutions. Journal of Molecular Modeling, 3, 364-368.
12. Elyashberg ME, Blinov KA, Williams AJ, Martirosian ER, Molodtsov SG. (2002) Application of a New Expert System for the Structure Elucidation of Natural Products from Their 1D and 2D NMR Data. Journal of Natural Products, 65, 693-703.
13. Steinbeck C. (1996) A program for Structure Elucidation from NMR Correlation Experiments. Angewandte Chemie International Edition in English, 35, 1984-1986.
14. Jaspers M. (1999) Computer assisted structure elucidation of natural products using two-dimensional NMR spectroscopy. Natural Product Reports 16, 241-248.
15. Steinbeck C. (2004) Recent developments in automated structure elucidation of natural products. Natural Product Reports, 21, 512-518.
16. Nuzillard J-M, Naanaa W, Pimont S, (1995) Applying the Constraint Satisfaction Problem Paradigm to Structure Generation. Journal of Chemical Information and Computer Science, 35, 1068-1073.
17. Nuzillard J-M. (2003) Automatic Structure Determination of Organic Molecules: Principle and Implementation of the LSD Program. Chinese Journal of Chemistry, 21, 1263-1267
18. Ley SV, Doherty K, Massiot G, Nuzillard J-M, (1994) " Connectivist" Approach to Organic Structure Determination. LSDProgram Assisted NMR Analysis of the Insect Antifeedant Azadirachtin. Tetrahedron, 50, 12267-12280.
19. Alvarenga SAV, Gastmans JP, Rodrigues GV, Emerenciano VP. (2001) A computer-assisted approach for chemotaxonomic studies - Diterpenes in Lamiaceae. Phytochemistry, 56, 583-595.
20. Emerenciano VP, Alvarenga SAV, Rodrigues GV, Ferreira MJP.(2005) A general survey and some taxonomic implications of diterpenes in the Asteraceae. Journal of The Linnean Society, 147, 291-308.
21. Emerenciano VP, Alvarenga SAV, Gastmans JP, Rodrigues GV, Ferreira MJP.(2003) SISTAX - An Intelligent tool in recovering information on natural products. Journal of Brazilian Chemical Society, 14, 369-374.
22. Gastmans JP, Zurita JC, Emerenciano VP. (1989) Prévision des Spectres de 13C par Ordinateur. Le Problème de La Codification. Analytica Chimica Acta, 217, 85-100.
23. Gastmans JP, Lopes MN, Furlan M, Emerenciano, VP.(1990) L' étude des signaux de 13C par microordinateur : un programme simple et rapide. Computers & Chemistry, 14, 75-78.
24. Emerenciano VP, Ferreira MJP, Rodrigues GV. (2004). Application of a new program, H1MACH, for predicition of iridoids skeletons. Spectroscopy Letters, 37, 587-605.
25. Ferreira MJP, Rodrigues GV, Emerenciano, VP.(2001) . Monoreg - An expert system for structural elucidation of monoterpenes. Canadian Journal of Chemistry, 79, 1915-1925.
26. Ferreira MJP, Oliveira FC, Alvarenga SAV, Macari PAT, Rodrigues GV, Emerenciano VP. (2002) Automatic Identification by 13C NMR of substituents bonded in natural products skeletons. Computers and Chemistry, 26, 601-632.
27. Ferreira MJP, Rodrigues GV, Emerenciano VP. (2001) Automatic identification of terpenoid skeletons through 13C NMR data disfunctionalization. Analytica Chimica Acta, 429, 151-170.
28. Fromanteau DL, Gastmans JP, Vestri SA, Emerenciano VP, Borges JHG. (1993) A Constraint Generator In Structural Determination By Microcomputer. Computer and Chemistry, 17, 369-378.
29. Oliveira FC, Ferreira MJP, Núñez CV, Rodrigues GV, Emerenciano VP. (2000). 13C NMR spectroscopy of eudesmane sesquiterpenes. Progress in NMR Spectroscopy, 37, 1-45.
30. Vestri SA., Gastmans JP, Rodrigues GV, Emerenciano, VP. (1997) Ditregra - An Auxiliary Program for Structural Determination of Diterpenes. Spectroscopy, 13, 227-249.
31. Macari PAT, Gastmans JP, Rodrigues GV, Emerenciano, VP. (1994) An Expert System for Structure Elucidation of Triterpenes. Spectroscopy, 12, 139-167.
32. Rufino AR. (2005) Using Computers for the Structural Elucidation of Alkaloids (in Portuguese). São Paulo University, São Paulo, Brazil.
33. Emerenciano VP, Melo DL, Rodrigues GV, Gastmans JP. (1997) Application of artificial intelligence in organic chemistry. Part XIX. Pattern recognition and structural determination of flavonoids using 13C NMR spectra. Spectroscopy, 13, 181-190.
34. Ferreira MJP, Costantin MB, Sartorelli P, Rodrigues GV, Limberger R, Henriques AT, Kato MJ, Emerenciano VP. (2001) Computer-aided method for identification of components in essential oils by 13C NMR spectroscopy. Analytica Chimica Acta, 447, 125-134.
35. Oliveira PM, Ferreira AA, Silveira D, Alves RB, Rodrigues GV, Emerenciano VP, Raslan DS. (2005) Diterpenoids from the aerial parts of Plectranthus ornatus. Journal of Natural Products, 68, 588-591.
36. Ferreira MJP. (2003) Spectral analysis, structure generation and prediction of 13C NMR spectra (in Portuguese). Doctoral Thesis. São Paulo University, Sao Paulo, Brazil.
37. Rodrigues MM, Rojas MCG, Nathan PJ. (2002) Quirogane, Prenopsane, and Patzcuarane Skeletons Obtained by Photochemically Induced Molecular Rearrangements of Longipinene Derivatives. Journal of Natural Products, 65, 1398-1411
38. Kinoshita T, Itaki N, Hikita M, Aoyagi Y, Hitotsuyanagi Y, Takeya K. (2005) The Isolation and Structre Elucidation of a New Sesquiterpene lactone from the Poisonous Plant Coriaria japonica (Coriariaceae). Chemical and Pharmaceutical Bulletin 53, 1040-1042
39. Harding WW, Tidgewell K, Schmidt M, Shah K, Dersch CM, Snyder J, Parrish D, Deschamps JR, Rothman RB, Prisinzano TE. (2005) Salvinicins A and B, New Neoclerodane Diterpenes from Salvia divinorum. Organic Letters, 7, 3017-3020.
40. Jin P, Deng Z, Pei Y, Fu H, Li J, Van Ofwegen L, Proksch P, Lin W. (2005) Polyhydroxylated steroids from the soft coral Sinularia dissecta. Steroids, 70, 487-493.
41. Zuleta LMC, Cavalheiro AJ, Silva DHS, Furlan M, Young MCM, Albuquerque S, Castro-Gamboa I, Bolzani VS (2005) seco- Iridoids from Calycophyllum spruceanum (Rubiaceae). Phytochemistry, 64, 549-553.
42. Xie WD, Zhang Q, Li PL, Jia ZJ. (2005) Two triterpenoids and other constituents form Petasites tricholobus. Phytochemistry, 66, 2340-2345.
43. Meiler J, Maier W, Will M, Meusinger R. (2002) Using neural networks for 13C NMR shift prediction - comparison with traditional methods. Journal of Magnetic Resonance, 157, 242-252.