ABSTRACT
Lamiaceae is one of the largest families of angiosperms and is classified into 12 subfamilies that are composed of 295 genera and 7775 species. It presents a variety of secondary metabolites such as diterpenes that are commonly found in their species, and some of them are known to be chemotaxonomic markers. The aim of this work was to construct a database of diterpenes and to use it to perform a chemotaxonomic analysis among the subfamilies of Lamiaceae, using molecular descriptors and self-organizing maps (SOMs). The 4115 different diterpenes corresponding to 6386 botanical occurrences, which are distributed in eight subfamilies, 66 genera, 639 different species and 4880 geographical locations, were added to SistematX. Molecular descriptors of diterpenes and their respective botanical occurrences were used to generate the SOMs. In all obtained maps, a match rate higher than 80% was observed, demonstrating a separation of the Lamiaceae subfamilies, corroborating with the morphological and molecular data proposed by Li et al. Therefore, through this chemotaxonomic study, we can predict the localization of a diterpene in a subfamily and assist in the search for secondary metabolites with specific structural characteristics, such as compounds with potential biological activity.
Subject(s)
Bioprospecting , Diterpenes/classification , Lamiaceae/classification , Algorithms , Databases as Topic , Diterpenes/chemistry , Machine Learning , PhylogenyABSTRACT
Our extended chemical investigation of the crude MeOH-CHCl3 extract of the gorgonian octocoral Briareum polyanthes from Puerto Rico has led to the isolation of three eunicellin-type diterpenoids, 1-3, along with five (4-8) diterpenoids of the asbestinane-type and one (9) of the briarane-type of polycyclized diterpenes. The structures and relative stereochemistry of the new compounds 1-9 were established on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HMBC, NOESY). The biological activity of these compounds against pathogenic microbes responsible for various human infectious diseases was investigated. In addition, new data recorded for four known asbestinin diterpenes also isolated during this investigation and further analysis through chemical reactions have prompted us to revise our original structural assignments for these compounds.
Subject(s)
Anthozoa/chemistry , Antimalarials , Antiviral Agents , Diterpenes , Herpesvirus 4, Human/drug effects , Plasmodium falciparum/drug effects , Animals , Antimalarials/chemistry , Antimalarials/classification , Antimalarials/isolation & purification , Antimalarials/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/classification , Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Chloroquine/pharmacology , Diterpenes/chemistry , Diterpenes/classification , Diterpenes/isolation & purification , Diterpenes/pharmacology , Drug Resistance , Humans , Molecular Structure , Puerto RicoABSTRACT
Two new diterpenes of the ent-trachylobane type were isolated from the stems of Xylopia langsdorffiana, ent-7alpha-acetoxytrachyloban-18-oic acid (1) and ent-7alpha-hydroxytrachyloban-18-oic acid (2). The structures of these isolates were deduced by spectroscopic data interpretation. X-ray crystallography of 1 was used to confirm its structure. The cytotoxic activity of 1 against V79 fibroblasts and rat hepatocytes was investigated.
Subject(s)
Annonaceae/chemistry , Diterpenes , Plants, Medicinal/chemistry , Animals , Brazil , Crystallography, X-Ray , Diterpenes/chemistry , Diterpenes/classification , Diterpenes/isolation & purification , Diterpenes/pharmacology , Fibroblasts/drug effects , Hepatocytes/drug effects , Male , Molecular Conformation , Molecular Structure , Plant Stems/chemistry , Rats , Rats, WistarABSTRACT
This paper describes a new computer approach for chemotaxonomic studies. The methodology employed enables the search for chemical substructures as taxonomic descriptors using an expert system built with plant natural products. The operation of the system was tested with diterpenes as taxonomic markers in Lamiaceae.