Phytotoxicity of Cardoon (Cynara cardunculus) Allelochemicals on Standard Target Species and Weeds

Cardoon (Cynara cardunculus L.) is a native plant to the Iberian Peninsula and the European Atlantic coast and invasive in American environments. Different solvents were used to perform cardoon extracts that were tested in phytotoxic bioassays. The ethyl acetate extract had the highest inhibitory activity so this was tested on the germination and growth of standard target species (lettuce, watercress, tomato, and onion) and weeds (barnyardgrass and brachiaria). The ethyl acetate extract was very active on root growth in both standard target species and weeds and it was therefore fractionated by chromatography. The spectroscopic data showed that the major compounds were sesquiterpene lactones. Aguerin B, grosheimin, and cynaropicrin were very active on etiolated wheat coleoptile, standard target species, and weed growth. The presence of these compounds explains the bioactivity of the ethyl acetate extract. The strong phytotoxicity of these compounds on important weeds shows the potential of these compounds as natural herbicide models

Incremental-Decremental Technique for Delineating Tunnels and Pockets in 3D Digital Images

In this paper, we combine two complementary techniques for computing homol- ogy: Incremental Algorithm for computing AT-models (which consist of an algebraic set of data that provide, in particular, homological information of the given object) is suitable for homology computation in cases in which new cells are added to the existing complex, whereas Decremental Algorithm for computing AT-models is more appropriated in the case that some cells are removed from the complex. Using these algorithms, we are able to de- scribe tunnels and pockets of a 3D digital image (given as a sequence of 2D digital images) in terms of sets of equivalent 1-cycles.Junta de Andalucía FQM-296Junta de Andalucía TIC-02268Ministerio de Educación y Ciencia MTM2006-0372

Influence of lipophilicity in O-acyl and O-alkyl derivatives of juglone and lawsone: a structure–activity relationship study in the search for natural herbicide models

Naphthoquinones are known for their broad range of biological activities. Given the increasing demands of consumers in relation to food quality and growing concerns about the impact of synthetic herbicides, it is necessary to search for newagrochemicals. Natural products and allelopathy provide newalternatives for the development of pesticides with lower toxicity and greater environmental compatibility. A structure–activity relationship to evaluate the effect of bioavailability was performed. A total of 44 O-acyl and O-alkyl derivatives of juglone and lawsone with different linear chain lengths were prepared. These compounds were tested on etiolated wheat coleoptiles, standard target species (STS) and four weeds, Echinochloa crus-galli L., Lolium rigidum Gaud., Lolium perenne L. and Avena fatua L. The results showed a strong influence of lipophilicity and, in most cases, the data fitted a logP-dependent quadratic mathematical model. The effects producedwere mostly stunting and necrosis caused by growth inhibition. The potential structure and activity behaviour is described

Absorption and Elimination of the Allelochemical MBOA by Weeds during Seedling Growth

6-Methoxy-2-benzoxazolinone (MBOA) is an allelochemical that is found in Poaceae and is generally associated with monocotyledon species. This compound is formed from the glycosylated form of 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (Gly-DIMBOA) by a two-stage degradation process. The MBOA detoxification capacity of two weed species, namely Echinochloa crus-galli and Lolium rigidum, and a resistant biotype of Lolium rigidum (SLR31) was studied both qualitatively and quantitatively. The product of metabolism is similar for both weed species. This finding indicates that these weeds probably metabolize xenobiotics by an identical route, since the product detected was the same in both cases. Kinetic studies on the absorption and translocation to the shoot showed differences in these processes depending on the species. The analysis of treated plants, which were subsequently transplanted to a growth medium without xenobiotic compound, showed that the weeds studied are capable of transmitting the previously absorbed compound to the medium by root exudation. The results show that this process is another defense mechanism of plants facing external threats

Sunflower Metabolites Involved in Resistance Mechanisms against Broomrape

Several strategies have been proposed to control parasitic plants and these include biological control, the use of herbicides, and suicidal germination or trap crops. In the case of sunflower, the most effective solution is genetic resistance. Nevertheless, the use of resistant cultivars is followed by the appearance of new and more virulent races of the parasite that overcome the existing sources of resistance. For this reason, it is necessary to increase our knowledge of the mechanisms involved in the resistant varieties. In this study, the presence of compounds involved in pre-attachment resistance mechanisms in sunflower varieties was analyzed. The production of stimulators of the germination of parasitic plant seeds and the concentration of the haustorial elongation inhibitor, scopoletin, were measured in exudates of resistant and susceptible sunflower varieties. It was found that dehydrocostuslactone and orobanchyl acetate are not involved in the resistance of the sunflower varieties studied. The results demonstrate that costunolide, heliolactone, and scopoletin are related to sunflower resistance. The sunflower varieties studied do not use all available options to fight parasitic plants. This could be one of the reasons that sunflower resistance is rapidly overcome by broomrape

Tectonoelins, new norlignans from a bioactive extract of Tectona grandis

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–C80 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

Synthesis of Bioactive Speciosins G and P from Hexagonia speciosa

The first total synthesis of speciosins P and G, previously isolated from Hexagonia speciosa, is reported. These compounds have been synthesized by Sonogashira coupling from readily available starting materials. Siccayne was also synthesized from the same starting material in two steps along with a number of other derivatives. The compounds were tested in the wheat coleoptile bioassay. The most active compound was the intermediate 18, followed by 29 and 17. The structural requirements for activity in these compounds are the presence of methoxy groups in the aromatic ring and a formyl or hydroxy group in the side chain

Synthesis of Vlasouliolides, a Pathway Towards Guaiane-Eudesmane C17/C15 Dimers by Photochemical and Michael Additions

Vladimiria souliei es una planta procedente de China que se aplica en medicina tradicional. Recientes estudios de aislamiento han llevado al descubrimiento de las vlasouliolidas, dímeros sesquiterpénicos naturales. Sin embargo, los rendimientos obtenidos del aislamiento han resultado ser realmente bajos (<0,01%) dificultando enormemente el estudio de estas moléculas. En este trabajo, proponemos una ruta sintética sencilla para obtener diferentes vlasouliolidas en buenos rendimientos a partir de deshidrocostuslactona y costunolido, lo que permitirá el estudio de su bioactividad a mayor escala

A Study on the Phytotoxic Potential of the Seasoning Herb Marjoram (Origanum majorana L.) Leaves

In the search of new alternatives for weed control, spices appear as an option with great potential. They are rich in bioactive natural products and edible, which might minimize toxicity hazard. Marjoram (Origanum majorana L.) is an aromatic herb that has been widely employed as a seasoning herb in Mediterranean countries. Although marjoram boasts a plethora of therapeutic properties (painkiller, antibiotic, treatment for intestinal disorders, etc.), the potential for its extracts for weed control is still to be more thoroughly explored. In order to determine their phytotoxic potential, marjoram leaves were subjected to different bioguided extraction processes, using water, ethyl acetate, acetone or methanol. The most active extract (acetone) was sequentially fractionated to identify its most active compounds. This fractionation led to the isolation and identification of 25 compounds that were classified as monoterpenes, diterpenes or flavonoids. Among them, a new compound named majoradiol and several compounds are described in marjoram for the first time. The phytotoxicity of the major compounds to etiolated wheat coleoptiles was compared against that of the commercial herbicide (Logran(R)), with similar or higher activity in some cases. These results confirm the extraordinary potential of the extracts from this edible plant to develop safer and more environmentally friendly herbicides

Strategies for the synthesis of canonical, non-canonical and analogues of strigolactones, and evaluation of their parasitic weed germination activity

Strigolactones (SLs) are natural products with promising applications as agrochemicals to prevent infestation with parasitic weeds due to their ability to trigger seed germination. However, their use is still limited because of the low yields in which they are isolated from natural sources. As such, numerous studies have led to strategies for obtaining them, and various structural analogues, by organic synthesis. These analogues have focused attention on the study of SLs, as some of them are easier to synthesize and possess enhanced properties, such as the level of bioactivity. This review provides an overview of the synthesis of SLs, subsequently focusing on the production of analogues with the canonical structure. The germinating activity of the compounds is also described herein, with positive effects on different species of the problematic genera Striga, Orobanche and Phelipanche having been found. The highly active analogue GR24 is currently the most widely studied in the literature, and relevant structural-activity relationships have been proposed as a result of the study of derivatives functionalized in different positions. Analogues based on other natural SLs such as strigol and orobanchol have also been developed, as have some novel canonical SLs derived from eudesmanolide or guaianolide sesquiterpene lactones. This review aims to provide useful information for the development of bioactive compounds applicable in new generation herbicides, in an attempt to employ similar compounds to those produced naturally in ecosystems that provoke effective herbicide effects at low concentrations.This work was supported by the ``Ministerio de Economi ' a, Industria y Competitividad'' (MINEICO), Spain, Project AGL2017-88-083-R