Puerto Real, Spain
Puerto Real, Spain

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Arroyo E.,Grupo de Alelopatia | Chinchilla N.,Grupo de Alelopatia | Molinillo J.M.G.,Grupo de Alelopatia | Macias F.A.,Grupo de Alelopatia
Mutation Research - Genetic Toxicology and Environmental Mutagenesis | Year: 2010

Benzoxazinones (BAs) are natural products that are present in Gramineae and represent part of the plant defence system against pests. In recent years, sprouts of maize, wheat and rye have been used for the production of dietary supplements. We have investigated the potential genotoxic activities of a diverse range of synthetic derivatives of the most abundant natural BA, namely DIBOA (2,4-dihydroxy-1,4-benzoxazin-3-one), proposed for use as a potential herbicide. We have tested 18 synthetic BAs for potential effects in cultured HeLa cells. We found significantly higher micronucleus (MN) induction over the background level, with the solvent DMSO used as an internal control. Concentration-dependent effects were found between 1. nM and 20. nM for all the synthetic compounds studied. Immunostaining with an anticentromere antibody showed that >80% of MN induced gave a centromere-positive signal. Similarly, fluorescence in situ hybridization (FISH) analysis with alphoid centromere probes showed a positive hybridization signal, indicating that all compounds analyzed are aneugenic. Chemical modification of the N in the heterocyclic aromatic amine served us to suggest a relationship between the structure and the aneugenic effects of the compounds analyzed. Our findings indicate that benzoxazinoids could be potential genotoxins for human cells. © 2009 Elsevier B.V.


Watanabe Y.,Kagawa University | Novaes P.,Grupo de Alelopatia | Varela R.M.,Grupo de Alelopatia | Molinillo J.M.G.,Grupo de Alelopatia | And 2 more authors.
Chemistry and Biodiversity | Year: 2014

Onopordum acanthium L. (Asteraceae) is a plant native to southern Europe and southwestern Asia, but it is invasive in disturbed areas and agricultural fields around the world, causing many agronomic problems by interfering with crops or preventing animals from grazing on pastures. Allelopathy could be one of the reasons that this plant has spread over different continents. The aim of the present study was to bioprospect O. acanthium leaf extracts through the isolation and purification of allelopathic secondary metabolites with phytotoxicity to explain their invasive behavior. Phytotoxic activity was tested using etiolated wheat coleoptiles. The most active extract was selected to perform a bioassay-guided isolation of two flavonoids, pectolarigenin (1) and scutellarein 4-methyl ether (2), and two sesquiterpene lactones, elemanolide 11(13)-dehydromelitensin β-hydroxyisobutyrate (3) and acanthiolide (4). All compounds were isolated for the first time from O. acanthium, and acanthiolide (4) is described for the first time. Compound 3 strongly inhibited the growth of wheat coleoptiles and 1 showed an intermediate effect. The results indicate that these compounds could contribute to the invasion of O. acanthium in ecological systems and agricultural fields. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.


Lacret R.,Grupo de Alelopatia | Varela R.M.,Grupo de Alelopatia | Molinillo J.M.G.,Grupo de Alelopatia | Nogueiras C.,University of Habana | MacIas F.A.,Grupo de Alelopatia
Phytochemistry Letters | Year: 2012

A phytochemical study on the most bioactive extract from Tectona grandis led to the isolation of two new norlignans, tectonoelin A and tectonoelin B, together with ten known compounds. The structures of the compounds were determined by a combination of 1D and 2D NMR techniques. This is the first time that this type of compound (C8-C8′ linkage norlignans) has been isolated from a dicotyledon. The general bioactivities of the isolated compounds have been studied using etiolated wheat coleoptiles. The activities showed that the isolated lignans and norlignans should be part of the defence mechanisms of this plant. © 2012 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.


PubMed | Grupo de Alelopatia
Type: Journal Article | Journal: Mutation research | Year: 2010

Benzoxazinones (BAs) are natural products that are present in Gramineae and represent part of the plant defence system against pests. In recent years, sprouts of maize, wheat and rye have been used for the production of dietary supplements. We have investigated the potential genotoxic activities of a diverse range of synthetic derivatives of the most abundant natural BA, namely DIBOA (2,4-dihydroxy-1,4-benzoxazin-3-one), proposed for use as a potential herbicide. We have tested 18 synthetic BAs for potential effects in cultured HeLa cells. We found significantly higher micronucleus (MN) induction over the background level, with the solvent DMSO used as an internal control. Concentration-dependent effects were found between 1nM and 20nM for all the synthetic compounds studied. Immunostaining with an anticentromere antibody showed that >80% of MN induced gave a centromere-positive signal. Similarly, fluorescence in situ hybridization (FISH) analysis with alphoid centromere probes showed a positive hybridization signal, indicating that all compounds analyzed are aneugenic. Chemical modification of the N in the heterocyclic aromatic amine served us to suggest a relationship between the structure and the aneugenic effects of the compounds analyzed. Our findings indicate that benzoxazinoids could be potential genotoxins for human cells.

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