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1.
J Chem Ecol ; 46(9): 871-880, 2020 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-32691372

RESUMEN

Weeds have been a major threat in agriculture for several generations as they lead to decreases in productivity and cause significant economic losses. Parasitic plants are a specific type of weed causing losses in crops of great relevance. A new strategy has emerged in the fight against parasitic plants, which is called 'suicidal germination' or the 'honey-pot strategy'. Regarding the problem of weed control from an ecological point of view, it is interesting to investigate new natural compounds with allelopathic activity with the aim of developing new natural herbicides that can inhibit the growth of weeds without damaging the environment. Safflower crops have been affected by parasitic plants and weeds and, as a consequence, the secondary metabolites exuded by safflower roots have been studied. The sesquiterpene lactone dehydrocostuslactone was isolated and characterised, and the structurally related costunolide was identified by UHPLC-MS/MS in safflower root exudates. These sesquiterpene lactones have been shown to stimulate germination of Phelipanche ramosa and Orobanche cumana seeds. In addition, these compounds were phytotoxic on three important weeds in agriculture, namely Lolium perenne, Lolium rigidum and Echinochloa crus-galli. The exudation of the strigolactones solanacol and fabacyl acetate have also been confirmed by UHPLC-MS/MS. The study reported here contributes to our knowledge of the ecological role played by some secondary metabolites. Moreover, this knowledge could help identify new models for the development of future agrochemicals based on natural products.


Asunto(s)
Carthamus tinctorius/parasitología , Germinación/efectos de los fármacos , Raíces de Plantas/parasitología , Malezas/efectos de los fármacos , Control de Malezas/métodos , Alelopatía , Cromatografía Liquida , Lactonas/aislamiento & purificación , Lactonas/farmacología , Lolium/efectos de los fármacos , Lolium/crecimiento & desarrollo , Orobanche/efectos de los fármacos , Orobanche/crecimiento & desarrollo , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Exudados de Plantas/aislamiento & purificación , Exudados de Plantas/farmacología , Raíces de Plantas/química , Semillas/efectos de los fármacos , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Espectrometría de Masas en Tándem
2.
Molecules ; 24(19)2019 Sep 25.
Artículo en Inglés | MEDLINE | ID: mdl-31557920

RESUMEN

A new sesquiterpenoid belonging to the subgroup seco-eudesmanolides and named inuloxin E was isolated from Dittrichia viscosa, together with the already known sesquiterpenoids inuloxins A-D and α-costic acid. Inuloxin E was characterized by spectroscopic data (essentially NMR and ESI MS) as 3-methylene-6-(1-methyl-4-oxo-pentyl)-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one. Its relative configuration was determined by comparison with the closely related inuloxin D and chemical conversion of inuloxin E into inuloxin D and by the observed significant correlation in the NOESY spectrum. Both inuloxins D and E induced germination of the parasitic weed Orobanche cumana, but were inactive on the seeds of Orobanche minor and Phelipanche ramosa. The germination activity of some hemisynthetic esters of inuloxin D was also investigated.


Asunto(s)
Asteraceae/química , Orobanche/efectos de los fármacos , Orobanche/crecimiento & desarrollo , Extractos Vegetales/farmacología , Sesquiterpenos/farmacología , Germinación/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Semillas/efectos de los fármacos , Sesquiterpenos/química
3.
J Agric Food Chem ; 62(43): 10485-92, 2014 Oct 29.
Artículo en Inglés | MEDLINE | ID: mdl-25272312

RESUMEN

Orobanche and Phelipanche species (the broomrapes) are root parasitic plants, some of which cause heavy yield losses on important crops. The development of herbicides based on natural metabolites from microbial and plant origin, targeting early stages on parasitic plant development, might contribute to the reduction of broomrape seed bank in agricultural soils. Therefore, the effect of metabolites belonging to different classes of natural compounds on broomrape seed germination and radicle development was assayed in vitro. Among the metabolites tested, epi-sphaeropsidone, cyclopaldic acid, and those belonging to the sesquiterpene class induced broomrape germination in a species-specific manner. epi-Epoformin, sphaeropsidin A, and cytochalasans inhibited germination of GR24-treated broomrape seeds. The growth of broomrape radicle was strongly inhibited by sphaeropsidin A and compounds belonging to cyclohexene epoxide and cytochalasan classes. Broomrape radicles treated with epi-sphaeropsidone developed a layer of papillae while radicles treated with cytochalasans or with sphaeropsidin A turned necrotic. These findings allow new lead natural herbicides for the management of parasitic weeds to be identified.


Asunto(s)
Hongos/química , Germinación/efectos de los fármacos , Herbicidas/farmacología , Orobanche/efectos de los fármacos , Extractos Vegetales/farmacología , Malezas/crecimiento & desarrollo , Plantas/química , Herbicidas/química , Herbicidas/aislamiento & purificación , Orobanche/crecimiento & desarrollo , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Malezas/efectos de los fármacos , Semillas/efectos de los fármacos , Semillas/crecimiento & desarrollo
4.
J Agric Food Chem ; 61(44): 10481-7, 2013 Nov 06.
Artículo en Inglés | MEDLINE | ID: mdl-24117219

RESUMEN

Orobanche cumana is a serious threat for cultivation of sunflower in Europe and Asia. Germination of the parasite is induced by metabolites released from the host root system. The first germination stimulant from sunflower root exudate was recently identified as dehydrocostus lactone, a sesquiterpene lactone. Bioassay-guided fractionation of root exudates now showed the release of additional sesquiterpene lactones. Besides dehydrocostus lactone, costunolide, tomentosin, and 8-epixanthatin were purified and identified spectroscopically. All four compounds induced germination of O. cumana at nano- to micromolar concentrations. Costunolide and dehydrocostus lactone concentrations above 1 µM reduced the activity, and application of 100 µM inhibited germination irreversibly. Seeds of Phelipanche ramosa could not be induced with costunolide. O. cumana seeds also germinated with GR24, a synthetic strigolactone. No bioactive fraction of sunflower contained compounds of this type. This supports previous findings that sesquiterpene lactones instead of strigolactones trigger the sunflower/O. cumana interaction.


Asunto(s)
Germinación/efectos de los fármacos , Helianthus/química , Lactonas/farmacología , Orobanche/efectos de los fármacos , Extractos Vegetales/farmacología , Exudados de Plantas/química , Semillas/crecimiento & desarrollo , Sesquiterpenos/farmacología , Orobanche/crecimiento & desarrollo , Raíces de Plantas/química , Semillas/efectos de los fármacos
5.
J Agric Food Chem ; 61(41): 9797-803, 2013 Oct 16.
Artículo en Inglés | MEDLINE | ID: mdl-24044614

RESUMEN

Orobanche crenata is a parasitic weed that causes severe yield losses in important grain and forage legume crops. Cereals have been reported to inhibit O. crenata parasitism when grown intercropped with susceptible legumes, but the responsible metabolites have not been identified. A number of metabolites have been reported in cereals that have allelopathic properties against weeds, pests, and pathogens. We tested the effect of several allelochemicals identified in cereals on O. crenata seed germination and radicle development. We found that 2-benzoxazolinone, its derivative 6-chloroacetyl-2-benzoxazolinone, and scopoletin significantly inhibited O. crenata seed germination. Benzoxazolinones, l-tryptophan, and coumalic acid caused the stronger inhibition of radicle growth. Also, other metabolites reduced radicle length, this inhibition being dose-dependent. Only scopoletin caused cell necrotic-like darkening in the young radicles. Prospects for their application to parasitic weed management are discussed.


Asunto(s)
Alelopatía , Grano Comestible/química , Orobanche/efectos de los fármacos , Feromonas/farmacología , Extractos Vegetales/farmacología , Malezas/efectos de los fármacos , Semillas/crecimiento & desarrollo , Grano Comestible/metabolismo , Germinación/efectos de los fármacos , Orobanche/crecimiento & desarrollo , Feromonas/metabolismo , Extractos Vegetales/metabolismo , Malezas/crecimiento & desarrollo , Semillas/efectos de los fármacos , Control de Malezas
6.
PLoS One ; 8(3): e59715, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-23544089

RESUMEN

Sunflower broomrape is a noxious parasitic weed which has caused severe damage to crop ecosystems. Trap crops can release a mixture of allelochemicals to induce the germination of sunflower broomrape. We studied the allelopathic effects of soybean on sunflower broomrape. Fourteen common soybean cultivars were grown in pots. Samples were collected from soybean plants and rhizosphere soil at five growth stages (V1, V3, V5, R2, and R4). The allelopathic effects of soybean reached highest at the V3 stage. Methanolic extracts of soybean roots induced higher broomrape germination than methanolic extracts of stems or leaves. The germination rates induced by root extracts (10-fold dilution) were positively correlated with germination rates induced by stem (10-fold dilution) and leaf extracts (10-fold dilution). The broomrape germination rates induced by root extracts were also positively correlated with soybean nodule diameter and dry weight. The results indicated that soybeans could induce sunflower broomrape germination. We conclude that soybean has the potential to be used as a trap crop for sunflower broomrape.


Asunto(s)
Ecotipo , Germinación/fisiología , Glycine max/fisiología , Orobanche/crecimiento & desarrollo , Germinación/efectos de los fármacos , Orobanche/efectos de los fármacos , Extractos Vegetales/farmacología , Hojas de la Planta/química , Rizosfera , Suelo , Glycine max/efectos de los fármacos
7.
Sci China Life Sci ; 55(3): 250-60, 2012 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-22527522

RESUMEN

The co-evolution of Orobanche spp. and their hosts within the same environment has resulted in a high degree of adaptation and effective parasitism whereby the host releases parasite germination stimulants, which are likely to be unstable in the soil. Our objective was to investigate whether extracts from non-host plants, specifically, Chinese medicinal plants, could stimulate germination of Orobanche spp. Samples of 606 Chinese medicinal herb species were extracted with deionized water and methanol. The extracts were used to induce germination of three Orobanche species; Orobanche minor, Orobanche cumana, and Orobanche aegyptiaca. O. minor exhibited a wide range of germination responses to the various herbal extracts. O. cumana and O. aegyptiaca exhibited an intermediate germination response to the herbal extracts. O. minor, which has a narrow host spectrum, showed higher germination rates in response to different herbal extracts compared with those of O. cumana and O. aegyptiaca, which have a broader host spectrum. Methanolic extracts of many Chinese herbal species effectively stimulated seed germination among the Orobanche spp., even though they were not the typical hosts. The effective herbs represent interesting examples of potential trap crops. Different countries can also screen extracts from indigenous herbaceous plants for their ability to induce germination of Orobanche spp. seeds. The use of such species as trap plants could diminish the global soil seed bank of Orobanche.


Asunto(s)
Medicina Tradicional China/métodos , Orobanche/efectos de los fármacos , Plantas Medicinales/metabolismo , Germinación/efectos de los fármacos , Metanol/química , Fenómenos Fisiológicos de las Plantas , Raíces de Plantas/efectos de los fármacos , Plantas/efectos de los fármacos , Semillas/metabolismo , Suelo , Agua/química
8.
Commun Agric Appl Biol Sci ; 69(3): 49-52, 2004.
Artículo en Inglés | MEDLINE | ID: mdl-15759394

RESUMEN

Various types of broomrape (Orobanche cermua), such as parasitic weeds, live on the roots of many important crops. Different methods may be advised to eradicate this parasite. But the seed size is so tiny with high stability in the soil and having strong connection with the host, it is very difficult to eradicate this parasite and there is no useful and economic method has not been suggested in this regard yet. The seeds of all types of broomrape germinate in the soil only when they are exposed to the secretions of the host's roots, therefore, providing special combinations that cause the parasite's seeds germinate in the absence of the host, can be an effective way in controlling this parasite. The effect of the tobacco root's extract and the synthetic combinations as well as their mixtures with different concentrations on the germination of the seeds of Orobanche cermua Loefi were tested to introduce an effective combination that can be used in controlling this parasite. This experiment includes 28 treatments in three replications. The tobacco root's extract was derived from the tobacco roots planted in pots containing Perlit in different stages and were prepared in different concentrations. Synthetic combinations (including combinations 1, 2 and 3) were also prepared with concentration of 1, 2 and 3 parts per million (ppm), then these combinations were tested as treatments on Broomrape's seeds. At the end of experiment, it was concluded that all the combinations used in different concentrations in this experiment significantly differ from the control treatment in their effects in causing the Broomrape's seeds germinate. Among all the combinations examined, the following were the most effective ones in the process of the germination of the Broomrape's seeds: 1. combination 2 with the concentration of one part per million, 2. combination 2 with the concentration of two parts per million, and 3 tobacco root's extract in the third stage.


Asunto(s)
Germinación/efectos de los fármacos , Nicotiana , Orobanche/fisiología , Extractos Vegetales/farmacología , Raíces de Plantas , Semillas/fisiología , Relación Dosis-Respuesta a Droga , Flores/crecimiento & desarrollo , Orobanche/efectos de los fármacos , Semillas/efectos de los fármacos , Nicotiana/crecimiento & desarrollo
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