Labdane dimers from Xylopia aromatica

From the stem bark of Xylopia aromatica (Annonaceae), have been isolated two new labdane dimers as their methyl esters, together with the known compounds ent-labda-8(17),13(16),14-trien-18-oic acid, sitosterol and stigmasterol. The structures of the dimers were elucidated on the basis of detailed spectroscopic analyses. (C) 1999 Elsevier B.V. Ltd. All rights reserved

A general survey and some taxonomic implications of diterpenes in the Asteraceae

This paper provides a general survey of the occurrence of diterpenes in the Asteraceae. Data on 4351 botanical occurrences were obtained from the literature. These were grouped by skeleton for each genus. Then, the genera were grouped by subtribes, which, in turn, were gathered in tribes, followed by subfamilies. In spite of the low number of species containing diterpenes, it was possible to describe some structural features of these compounds, i.e. The skeletal types in various taxa and the positions in some skeletons that are always oxidized or never undergo oxidation in some genera. Thus, it was verified that: in the subfamily Cichorioideae, only a few of the studied species possess diterpenes, wherein kaurane is the most frequent diterpene skeleton. In the Asteroideae, the presence of diterpenes is much greater than that in the Cichorioideae and Carduoideae. At tribal taxonomic level, for example, the Astereae produce labdanes and clerodanes; Heliantheae and Eupatorieae produce kauranes and labdanes, respectively; and Calenduleae produce pimaranes. Some taxonomic implications are presented. (c) 2005 the Linnean Society of London

Chemosystematic studies of natural compounds isolated from Asteraceae: characterization of tribes by principal component analysis

This work describes an application of principal component analysis (PCA) on a database of secondary metabolites from the Asteraceae family. The numbers of occurrences of metabolites in 11 chemical classes for the different vibes of the family were used as variables, PCA allows the identification of chemical classes that contribute most to the subgroups classification within the family. Relationships between chemical composition and botanical classification were made. (C) 2001 Elsevier B.V. B.V. All rights reserved

NATURAL PRODUCT SUBSTITUTION PATTERN AND SKELETAL RECOGNITION METHOD

This work describes a methodology for identification of skeletal types of diterpenes based on data base with 1500 compounds isolated from Asteraceae. One program named BOTOCSYS was built with the codification of the compounds and their botanical sources. An example of identification of a new substance is given

Prediction of occurrences of diverse chemical classes in the Asteraceae through artificial neural networks

The training and the application of a neural network system for the prediction of occurrences of secondary metabolites belonging to diverse chemical classes in the Asteraceae is described. From a database containing about 604 genera and 28,000 occurrences of secondary metabolites in the plant family, information was collected encompassing nine chemical classes and their respective occurrences for training of a multi-layer net using the back-propagation algorithm. The net supplied as output the presence or absence of the chemical classes as well as the number of compounds isolated from each taxon. The results provided by the net from the presence or absence of a chemical class showed a 89% hit rate; by excluding triterpenes from the analysis, only 5% of the genera studied exhibited errors greater than 10%. Copyright (C) 2004 John Wiley Sons, Ltd

Automatic identification by C-13 NMR of substituent groups bonded in natural product skeletons

The aim of this paper is to present a procedure that utilizes C-13 NMR for identification of substituent groups which are bonded to carbon skeletons of natural products. For so much was developed a new version of the program (MACRONO), that presents a database with 161 substituent types found in the most varied terpenoids. This new version was widely tested in the identification of the substituents of 60 compounds that, after removal of the signals that did not belong to the carbon skeleton, served to test the prediction of skeletons by using other programs of the expert system (SISTEMAT). (C) 2002 Elsevier B.V. Ltd. All rights reserved