New Improvements in Automatic Structure Elucidation Using the LSD (Logic for Structure Determination) and the SISTEMAT Expert Systems

This article describes the integration of the LSD (Logic for Structure Determination) and SISTEMAT expert systems that were both designed for the computer-assisted structure elucidation of small organic molecules. A first step has been achieved towards the linking of the SISTEMAT database with the LSD structure generator. The skeletal descriptions found by the SISTEMAT programs are now easily transferred to LSD as substructural constraints. Examples of the synergy between these expert systems are given for recently reported natural products.

[1]  Alejandro F. Barrero,et al.  Germacranolides from Centaurea melitensis. , 1989 .

[2]  M. Buděšínský,et al.  Carbon-13 NMR Spectra of Sesquiterpene Lactones , 1995 .

[3]  Helen Skaltsa,et al.  Minor sesquiterpene lactones from Centaurea pullata and their antimicrobial activity. , 2007, Journal of natural products.

[4]  Marcelo J. P. Ferreira,et al.  MONOREG - an expert system for structural elucidation of monoterpenes , 2001 .

[5]  J. P. Gastmans,et al.  Prevision des spectres de résonance magnétique nucléaire de 13C par intelligence artificielle: le problème de la codification , 1989 .

[6]  P. Vérité,et al.  An alkaloid, two conjugate sesquiterpenes and a phenylpropanoid from Pachypodanthium confine Engl. and Diels. , 2007, Phytochemistry.

[7]  Si Zhang,et al.  Xylocarpins A and B, two new mexicanolides from the seeds of a Chinese mangrove Xylocarpus granatum: NMR investigation in mixture , 2007, Magnetic resonance in chemistry : MRC.

[8]  Marcelo J. P. Ferreira,et al.  A program for terpenoid skeleton prediction based on botanical information , 2003 .

[9]  Joshua Lederberg,et al.  Applications of Artificial Intelligence for Organic Chemistry: The DENDRAL Project , 1980 .

[10]  Mara B. Costantin,et al.  Computer-Assisted Approach to Structural Elucidation of Lignans , 2008 .

[11]  Marcelo J. P. Ferreira,et al.  Automatic identification of terpenoid skeletons through 13C nuclear magnetic resonance data disfunctionalization , 2001 .

[12]  A Numata,et al.  Isolation and structures of schleicherastatins 1-7 and schleicheols 1 and 2 from the teak forest medicinal tree Schleichera oleosa. , 2000, Journal of natural products.

[13]  C. Steinbeck Recent developments in automated structure elucidation of natural products. , 2004, Natural product reports.

[14]  Antony J. Williams,et al.  Computer-assisted structure verification and elucidation tools in NMR-based structure elucidation , 2008 .

[15]  Jean-Marc Nuzillard,et al.  Automatic Structure Determination of Organic Molecules: Principle and Implementation of the LSD Program , 2010 .

[16]  Eamonn F. Healy,et al.  Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model , 1985 .

[17]  Eamonn F. Healy,et al.  Comments on a comparison of AM1 with the recently developed PM3 method , 1990 .

[18]  J. Nuzillard,et al.  Computer‐assisted elucidation of structures of natural products , 1992 .

[19]  Marcos Nogueira Eberlin,et al.  Iridoid glucosides from Randia spinosa (Rubiaceae). , 2003, Phytochemistry.

[20]  J. Meiler,et al.  Using neural networks for (13)c NMR chemical shift prediction-comparison with traditional methods. , 2002, Journal of magnetic resonance.

[21]  Denise L. G. Fromanteau,et al.  A Constraints Generator in Structural Determination by Microcomputer , 1993, Comput. Chem..

[22]  B. Bodo,et al.  Minor biflavonoids from Lophira alata leaves. , 2006, Journal of natural products.

[23]  Marcus Tullius Scotti,et al.  Computer-aided prediction of 125Te and 13C NMR chemical shifts of diorgano tellurides , 2007 .

[24]  Mara B. Costantin,et al.  Application of a New Program, H1MACH, for Prediction of Iridoid Skeletons , 2004 .

[25]  Vicente de Paulo Emerenciano,et al.  Automatic Identification by 13C NMR of Substituent Groups Bonded in Natural Product Skeletons , 2002, Comput. Chem..

[26]  J. Nuzillard,et al.  Logic for structure determination , 1991 .

[27]  Mohammed Hosny,et al.  Secoiridoid glucosides from Fraxinus oxycarba , 1998 .

[28]  J. Dubois,et al.  Elucidation by progressive intersection of ordered substructures from carbon-13 nuclear magnetic resonance , 1988 .

[29]  J. Matsoukas,et al.  Isolation, NMR studies, and biological activities of onopordopicrin from Centaurea sonchifolia. , 1992, Journal of natural products.

[30]  Marcel Jaspars Computer‐Assisted Structure Elucidation of Natural Products Using Two‐Dimensional NMR Spectroscopy , 1999 .

[31]  Hui Yang,et al.  Bioactive benzophenones from Garcinia xanthochymus fruits. , 2005, Journal of natural products.

[32]  Jean-Marc Nuzillard,et al.  NPC Natural Product Communications 2006 Vol . 0 Automatic Structure Elucidation through Data Base Search and 2 D NMR Spectral Analysis , 2006 .

[33]  Neil A. B. Gray,et al.  Computer-assisted structure elucidation , 1986 .