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1.
Chem Biodivers ; 18(12): e2100701, 2021 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-34622554

RESUMEN

The chemical profile and allelopathic action of the volatiles produced by Artemisia selengensis were studied. Artemisia selengensis was found to release volatile chemicals to the environment to influence other plants' growth, which suppressed the root length of Amaranthus retroflexus and Poa annua by 50.46 % and 87.83 % under 80 g/1.5 L treatment, respectively. GC/MS analysis led to the identification of 41 compounds (by hydrodistillation, HD) and 48 compounds (by headspace solid-phase microextraction, HS-SPME), with eucalyptol (15.45 % by HD and 28.09 % by HS-SPME) being detected as the most abundant constituent. The essential oil (EO) of A. selengensis completely inhibited the seed germination of A. retroflexus and P. annua at 1 mg/mL and 0.5 mg/mL, respectively. However, eucalyptol displayed much weaker activity compared with the EO, indicating that other less abundant constituents might contribute significantly to the EO's activity. Our study is the first report on the phytotoxicity of A. selengensis EO, suggesting that A. selengensis might release allelopathic volatile agents into the environment that negatively affect other plants' development so as to facilitate its own dominance; the potential value of utilizing A. selengensis EO as an environmentally friendly herbicide is also discussed.


Asunto(s)
Amaranthus/efectos de los fármacos , Artemisia/química , Desarrollo de la Planta/efectos de los fármacos , Raíces de Plantas/efectos de los fármacos , Poa/efectos de los fármacos , Compuestos Orgánicos Volátiles/farmacología , Amaranthus/crecimiento & desarrollo , Poa/crecimiento & desarrollo , Compuestos Orgánicos Volátiles/química , Compuestos Orgánicos Volátiles/aislamiento & purificación
2.
Chem Biodivers ; 18(12): e2100679, 2021 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-34651409

RESUMEN

Pomelo seeds (PS) are important by-product of pomelo fruits (Citrus grandis Osbeck). The value-added utilization of PS remains highly challenged. This study aimed to investigate the utilization potential of PS as natural antioxidant, antibacterial, herbicidal agents, and their functional components. The ethanolic extract (EE) of PS and its four fractions as PEE (petroleum ether extract), AcOEtE (ethyl acetate extract), BTE (butanol extract), and WE (water extract), were prepared and biologically evaluated. BTE exhibited the best antioxidant activity among all these extracts, in both ABTS (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt) and FRAP (ferric reducing antioxidant power) assays. AcOEtE was superior to other extracts in herbicidal assay against both Festuca elata Keng (IC50 of 0.48 mg mL-1 ) and Amaranthus retroflexus L. (IC50 of 0.94 mg mL-1 ). Meanwhile, both AcOEtE and BTE demonstrated inhibitory effects against Bacillus subtilis, Escherichia coli, and Xanthomonas citri subsp. citri, with MIC ranging 2.5-5.0 mg mL-1 . Furthermore, the primary chemical components involving naringin, deacetylnomilin, limonin, nomilin, and obacunone, were quantified in all these extracts. PCA (principal component analysis) suggested that naringin might highly contribute to the antioxidant activity of PS, and the herbicidal activity should be ascribed to limonoids. This study successfully identified AcOEtE and BTE as naturally occurring antioxidant, antibacterial, and herbicidal agents, showing application potential in food and cosmetics industries, and organic farming agriculture.


Asunto(s)
Antibacterianos/farmacología , Antioxidantes/farmacología , Citrus/química , Herbicidas/farmacología , Extractos Vegetales/farmacología , Semillas/química , Amaranthus/efectos de los fármacos , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Bacillus subtilis/efectos de los fármacos , Benzotiazoles/antagonistas & inhibidores , Escherichia coli/efectos de los fármacos , Festuca/efectos de los fármacos , Herbicidas/química , Herbicidas/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Ácidos Sulfónicos/antagonistas & inhibidores , Xanthomonas/efectos de los fármacos
3.
Chem Biodivers ; 17(4): e2000043, 2020 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-32112467

RESUMEN

Alternariol and altenuisol were isolated as the major phytotoxins produced by an Alternaria sp. pathogenic fungus of the invasive weed Xanthium italicum. Altenuisol exhibited stronger phytotoxic effect compared with alternariol. At 10 µg/mL, alternariol and altenuisol promoted root growth of the monocot plant Pennisetum alopecuroides by 11.1 % and 75.2 %, respectively, however, inhibitory activity was triggered by the increase of concentration, with root elongation being suppressed by 35.5 % and 52.0 % with alternariol and altenuisol at 1000 µg/mL, respectively. Alternariol slightly inhibited root length of the dicot plant Medicago sativa at 10-1000 µg/mL, whereas altenuisol stimulated root growth by 51.0 % at 10 µg/mL and inhibited root length by 43.4 % at 200 µg/mL. Alternariol and altenuisol did not exert strong regulatory activity on another dicot plant, Amaranthus retroflexus, when tested concentration was low, however, when the concentration reached 1000 µg/mL, they reduced root length by 68.1 % and 51.0 %, respectively. Alternariol and altenuisol exerted similar effect on shoot growth of three tested plants but to a lesser extent. It is noteworthy to mention that this is the first report on the phytotoxicity of altenuisol.


Asunto(s)
Alternaria/química , Micotoxinas/química , Xanthium/microbiología , Alternaria/aislamiento & purificación , Alternaria/metabolismo , Amaranthus/efectos de los fármacos , Amaranthus/crecimiento & desarrollo , Especies Introducidas , Lactonas/química , Lactonas/aislamiento & purificación , Lactonas/farmacología , Micotoxinas/aislamiento & purificación , Micotoxinas/farmacología , Pennisetum/efectos de los fármacos , Pennisetum/crecimiento & desarrollo , Raíces de Plantas/efectos de los fármacos , Raíces de Plantas/crecimiento & desarrollo , Brotes de la Planta/efectos de los fármacos , Brotes de la Planta/crecimiento & desarrollo , Brotes de la Planta/fisiología
4.
J Sci Food Agric ; 100(3): 1185-1194, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-31680262

RESUMEN

BACKGROUND: Ludwigia hyssopifolia (G. Don) Exell, one of the problem weeds in some rice-producing countries, was studied to determine its allelopathic potential based on the effects of aqueous extracts of its tissues (leaves, roots and stem) on seedling growth of selected weeds and rice. The major phenolic compound of its leaves was also isolated and characterized. RESULTS: L. hyssopifolia aqueous leaf extract showed significant inhibition of shoot growth and biomass accumulation of weeds (Amaranthus spinosus L., Dactyloctenium aegyptium L., Cyperus iria L.) while maintaining less adverse effects on rice (crop) compared to other aqueous extracts of roots and stem. Phytochemical screening showed that phenols, tannins, flavonoids, terpenoids, saponins and coumarins are found in its leaf aqueous extract. The Folin-Ciocalteu method revealed that its leaves contain 26.66 ± 0.30 mg GAE g-1 leaf. The extract was then acid-hydrolyzed to liberate the phenolics (25 mg phenolics g-1 leaf). The major compound was isolated via preparative thin-layer chromatography using formic acid-ethyl acetate-n-hexane (0.05:4:6) solvent system. It had maximum UV absorption at 272 nm while its Fourier transform infrared spectrum revealed phenol, carboxylic acid and ether functionalities. This also had similar chromatographic mobility when run together with syringic acid in two-dimensional paper chromatography and thin-layer chromatography. CONCLUSIONS: L. hyssopifolia has potential allelopathic activity and its leaf aqueous extract showed the highest phytotoxic activity (P ≤ 0.05) indicating its potential as a bioherbicide. The most probable identity of the major phenolic compound is syringic acid. © 2019 Society of Chemical Industry.


Asunto(s)
Herbicidas/química , Onagraceae/química , Extractos Vegetales/química , Amaranthus/efectos de los fármacos , Amaranthus/crecimiento & desarrollo , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Herbicidas/aislamiento & purificación , Herbicidas/farmacología , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Hojas de la Planta/química , Malezas/efectos de los fármacos , Malezas/crecimiento & desarrollo , Taninos/química , Taninos/farmacología
5.
Molecules ; 24(24)2019 Dec 11.
Artículo en Inglés | MEDLINE | ID: mdl-31835831

RESUMEN

New herbicides based on natural products are claimed to address weed resistance and environmental concerns related to synthetic herbicides. In our previous studies, certain volatile organic compounds (VOCs) produced by Ulex europaeus and Cytisus scoparius were argued to be responsible for the phytotoxicity of both shrub species. Interactions among VOCs were hypothesized to explain the inconsistency between the effects of the identified pure compounds and those naturally emitted from fresh plant material. In this work, eugenol, verbenone, terpinen-4-ol, α-terpineol, and linalool were assayed as binary mixtures of Amaranthus retroflexus and Digitaria sanguinalis. Powerful synergistic inhibitory effects were revealed for germination and early growth. Only 3.1 ppm of verbenone was enough to inhibit A. retroflexus germination when paired to other VOCs. Eugenol was capable of exacerbating the effects of terpinen-4-ol on A. retroflexus, even though it was innocuous when acting alone at 12.5 ppm. The verbenone and linalool pair produced very significant synergistic effects in terms of D. sanguinalis germination. The synergistic effects were predominantly irreversible for D. sanguinalis, since seeds exposed to paired VOCs were unable to recover their germination capacity after removing the phytotoxins or produced damaged seedlings. Both shrub species have been revealed as sources of natural herbicide molecules, with promising synergistic modes of action that deserve to be studied in depth.


Asunto(s)
Cytisus/química , Herbicidas/farmacología , Ulex/química , Compuestos Orgánicos Volátiles/farmacología , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/farmacología , Amaranthus/efectos de los fármacos , Amaranthus/crecimiento & desarrollo , Monoterpenos Bicíclicos/química , Monoterpenos Bicíclicos/farmacología , Digitaria/efectos de los fármacos , Digitaria/crecimiento & desarrollo , Sinergismo Farmacológico , Eugenol/química , Eugenol/farmacología , Germinación/efectos de los fármacos , Herbicidas/química , Extractos Vegetales/química , Compuestos Orgánicos Volátiles/química
6.
Sci Rep ; 9(1): 12965, 2019 09 10.
Artículo en Inglés | MEDLINE | ID: mdl-31506442

RESUMEN

This study aimed at profiling the biological activities of Amaranthus caudatus cultivated on different soils in a glasshouse experiment. Five soil types namely; sandy clay loam, silty clay loam, clayey loam, loam and control (unfractionated soil) were experimentally formulated from primary particles of clay, sand and silt following the United State Department of Agriculture's (USDA) soil triangle technique. After harvesting at pre-flowering (61 days after planting), flowering (71 days after planting) and post-flowering (91 days after planting) stages, crude extracts were obtained with water and ethanol. Total flavonoids, phenolic and proanthocyanidin contents of the extracts, as well as their biological activities, were determined using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), 2,2 diphenyl-1-picrylhydrazyl ethanol (DPPH), nitric oxide and phosphomolybdate assays. It was observed that biological activity of A. caudatus varied with soil types, stages of maturity and solvents of extraction. The highest phytochemical yield was recorded in ethanolic extracts of clayey loam harvested prior to flowering and the same trend was replicated in the antioxidant properties of the plant. For optimal biological activity, it is recommended that clayey loam soil should be used for cultivation of A. caudatus and harvest should be made near flowering to capture high phytochemical yield from the species.


Asunto(s)
Amaranthus/crecimiento & desarrollo , Antioxidantes/farmacología , Arcilla/química , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Suelo/química , Amaranthus/efectos de los fármacos , Antioxidantes/química , Arcilla/clasificación , Fitoquímicos/química , Extractos Vegetales/química
7.
J Agric Food Chem ; 65(25): 5161-5172, 2017 Jun 28.
Artículo en Inglés | MEDLINE | ID: mdl-28605187

RESUMEN

Farmers of the Franca region in Brazil observed that Bidens sulphurea was able to eliminate the Panicum maximum weed, which infected coffee plantations, without affecting the crop. In an effort to determine if the inhibitory effects observed were due to the presence of phytotoxic compounds from leaves and roots, a biodirected isolation and spectroscopic characterization has been carried out. The leaf dichloromethane and root acetone extracts were the most active, and the former appeared to be more phytotoxic to the target species, including four weeds. A total of 26 compounds were isolated from leaves and roots, and four of them are described here for the first time. The major compounds in the leaf extract are the sesquiterpene lactones costunolide, reynosin, and santamarine, and these showed marked inhibition. Amaranthus viridis and Panicum maximum were the most sensitive species of the weeds tested. These three phytotoxic lactones were also evaluated on A. viridis and P. maximum under hydroponic conditions. A. viridis was the most affected species with the three lactones, and santamarine was the most phytotoxic compound on both. This is the first time that the phytotoxicity of sesquiterpene lactones has been evaluated on hydroponic culture. The work described here is a preliminary approach for the use of B. sulphurea for weed control in agriculture, both as a cover crop and by use of its components as natural herbicide leads.


Asunto(s)
Bidens/química , Herbicidas/toxicidad , Extractos Vegetales/toxicidad , Malezas/efectos de los fármacos , Amaranthus/efectos de los fármacos , Asteraceae/efectos de los fármacos , Brasil , Herbicidas/química , Herbicidas/aislamiento & purificación , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Raíces de Plantas/química , Control de Malezas
8.
Sci Rep ; 7: 44913, 2017 03 22.
Artículo en Inglés | MEDLINE | ID: mdl-28327669

RESUMEN

Gene flow is an important component in evolutionary biology; however, the role of gene flow in dispersal of herbicide-resistant alleles among weed populations is poorly understood. Field experiments were conducted at the University of Nebraska-Lincoln to quantify pollen-mediated gene flow (PMGF) from glyphosate-resistant (GR) to -susceptible (GS) common waterhemp using a concentric donor-receptor design. More than 130,000 common waterhemp plants were screened and 26,199 plants were confirmed resistant to glyphosate. Frequency of gene flow from all distances, directions, and years was estimated with a double exponential decay model using Generalized Nonlinear Model (package gnm) in R. PMGF declined by 50% at <3 m distance from the pollen source, whereas 90% reduction was found at 88 m (maximum) depending on the direction of the pollen-receptor blocks. Amplification of the target site gene, 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS), was identified as the mechanism of glyphosate resistance in parent biotype. The EPSPS gene amplification was heritable in common waterhemp and can be transferred via PMGF, and also correlated with glyphosate resistance in pseudo-F2 progeny. This is the first report of PMGF in GR common waterhemp and the results are critical in explaining the rapid dispersal of GR common waterhemp in Midwestern United States.


Asunto(s)
Amaranthus/efectos de los fármacos , Amaranthus/genética , Flujo Génico , Glicina/análogos & derivados , Resistencia a los Herbicidas/genética , Polen , Polinización , Glicina/farmacología , Herbicidas/farmacología , Patrón de Herencia , Modelos Teóricos , Fenotipo , Dispersión de las Plantas/genética , Malezas/genética , Glifosato
9.
Toxicol Ind Health ; 31(3): 247-54, 2015 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-23293131

RESUMEN

Laboratory experiments were performed to determine phytotoxic potentials of white top (Lepidium draba) methanol extracts (root, stem and leaf) on germination and early growth of corn (Zea mays) and redroot pigweed (Amaranthus retroflexus). Furthermore, the effects of different methanol extracts of L. draba on the phytohormone (indole-3-acetic acid (IAA), gibberellic acid (GA), abscisic acid (ABA) and zeatin) levels of corn and redroot pigweed were investigated. It was observed that all concentrations of methanol extracts of root, stem and leaf of L. draba inhibited germination, radicle and plumule elongation when compared with the respective controls. Besides this, the degree of inhibition was increased in concert with increasing concentrations of extracts used. On the other hand, phytohormone levels changed with the application of different extract concentrations. Comparing with the control, the GA levels significantly decreased while the ABA levels increased in all the application groups. Zeatin and IAA levels showed changes depending upon the applied extracts and concentrations.


Asunto(s)
Amaranthus/crecimiento & desarrollo , Germinación/efectos de los fármacos , Lepidium/toxicidad , Extractos Vegetales/toxicidad , Semillas/efectos de los fármacos , Semillas/crecimiento & desarrollo , Zea mays/crecimiento & desarrollo , Amaranthus/efectos de los fármacos , Lepidium/química , Extractos Vegetales/análisis , Reguladores del Crecimiento de las Plantas/farmacología , Hojas de la Planta/química , Raíces de Plantas/química , Tallos de la Planta/química , Zea mays/efectos de los fármacos
10.
J Hazard Mater ; 243: 212-22, 2012 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-23146354

RESUMEN

Carbon nanotubes (CNTs) are a novel nanomaterial with wide potential applications; however the adverse effects of CNTs following environmental exposure have recently received significant attention. Herein, we explore the systemic toxicity and potential influence of 0-1000 mg L(-1) the multi-walled CNTs on red spinach. The multi-walled CNTs exposed plants exhibited growth inhibition and cell death after 15 days of hydroponic culture. The multi-walled CNTs had adverse effects on root and leaf morphology, as observed by scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Raman spectroscopy detected the multi-walled CNTs in leaves. Biomarkers of nanoparticle toxicity, reactive oxygen species (ROS), and cell damage in the red spinach were greatly increased 15 days post-exposure to the multi-walled CNTs. These effects were reversed when the multi-walled CNTs were supplemented with ascorbic acid (AsA), suggesting a role of ROS in the multi-walled CNT-induced toxicity and that the primary mechanism of the multi-walled CNTs' toxicity is oxidative stress.


Asunto(s)
Amaranthus/efectos de los fármacos , Antioxidantes/farmacología , Ácido Ascórbico/farmacología , Nanotubos de Carbono/toxicidad , Amaranthus/crecimiento & desarrollo , Muerte Celular/efectos de los fármacos , Electrólitos/química , Azul de Evans , Hidroponía , Microscopía Electrónica de Rastreo , Microscopía Electrónica de Transmisión , Hojas de la Planta/efectos de los fármacos , Hojas de la Planta/crecimiento & desarrollo , Raíces de Plantas/efectos de los fármacos , Raíces de Plantas/crecimiento & desarrollo , Especies Reactivas de Oxígeno/química , Plantones/efectos de los fármacos , Plantones/crecimiento & desarrollo , Semillas , Espectrometría Raman
11.
Z Naturforsch C J Biosci ; 63(9-10): 639-43, 2008.
Artículo en Inglés | MEDLINE | ID: mdl-19040099

RESUMEN

In the context of the study on plant defensive compounds we have isolated the main alkaloid from Hippeastrum puniceum (Amaryllidaceae), 3-O-acetyl-narcissidine (1), and its biological activities tested against two divergent insect species and several plant species. 1 was isolated from the bioactive alkaloidal fraction of H. puniceum. Its chemical structure was established by spectroscopic analysis. The biological activity tests showed that 1 is an antifeedant against the polyphagous insect Spodoptera littoralis but not against the olyphage Leptinotarsa decemlineata. Furthermore, the root growth of Amaranthus hypochondriacus, Rottboellia cochinchinensis, Panicum maximum and Solanum lycopersicum was significantly affected by 1. These results suggest a plant protective role for H. puniceum alkaloids.


Asunto(s)
Alcaloides/química , Alcaloides de Amaryllidaceae/química , Compuestos Heterocíclicos de 4 o más Anillos/química , Compuestos Heterocíclicos de 4 o más Anillos/toxicidad , Insecticidas/química , Insecticidas/toxicidad , Liliaceae/química , Spodoptera/efectos de los fármacos , Aconitina/farmacología , Alcaloides/aislamiento & purificación , Amaranthus/efectos de los fármacos , Amaranthus/crecimiento & desarrollo , Alcaloides de Amaryllidaceae/aislamiento & purificación , Alcaloides de Amaryllidaceae/farmacología , Alcaloides de Amaryllidaceae/toxicidad , Animales , Compuestos Heterocíclicos de 4 o más Anillos/aislamiento & purificación , Insecticidas/aislamiento & purificación , Solanum lycopersicum/efectos de los fármacos , Solanum lycopersicum/crecimiento & desarrollo , Fisostigmina/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Raíces de Plantas/efectos de los fármacos , Raíces de Plantas/crecimiento & desarrollo , Plantas/efectos de los fármacos
12.
J Environ Biol ; 28(1): 63-6, 2007 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-17717987

RESUMEN

A study was undertaken to explore the phytotoxicity of volatile essential oil from Eucalyptus citriodora Hook. against some weeds viz. Bidens pilosa, Amaranthus viridis, Rumex nepalensis, and Leucaena leucocephala in order to assess its herbicidal activity. Dose-response studies conducted under laboratory conditions revealed that eucalypt oils (in concentration ranging from 0.0012 to 0.06%) greatly suppress the germination and seedling height of test weeds. At 0.06% eucalypt oil concentration, none of the seed of test weeds germinated. Among the weed species tested, A. viridis was found to be the most sensitive and its germination was completed inhibited even at 0.03%. Not only the germination and seedling growth, even the chlorophyll content and respiratory activity in leaves of emerged seedlings were severely affected. In A. viridis chlorophyll content and respiratory activity were reduced by over 51% and 71%, respectively, even at a very low concentration of 0.06%. These results indicated an adverse effect of eucalypt oils on the photosynthetic and energy metabolism of the test weeds. A strong negative correlation was observed between the observed effect and the concentration of eucalypt oil. Based on the study, it can be concluded that oil from E. citriodora possess strong inhibitory potential against weeds that could be exploited for weed management.


Asunto(s)
Eucalyptus/química , Germinación/efectos de los fármacos , Herbicidas/toxicidad , Aceites Volátiles/toxicidad , Aceites de Plantas/toxicidad , Amaranthus/efectos de los fármacos , Amaranthus/crecimiento & desarrollo , Amaranthus/metabolismo , Bidens/efectos de los fármacos , Bidens/crecimiento & desarrollo , Bidens/metabolismo , Respiración de la Célula/efectos de los fármacos , Clorofila/metabolismo , Fabaceae/efectos de los fármacos , Fabaceae/crecimiento & desarrollo , Fabaceae/metabolismo , Hojas de la Planta/efectos de los fármacos , Hojas de la Planta/metabolismo , Rumex/efectos de los fármacos , Rumex/crecimiento & desarrollo , Rumex/metabolismo , Plantones/efectos de los fármacos , Plantones/crecimiento & desarrollo
13.
J Agric Food Chem ; 53(16): 6276-80, 2005 Aug 10.
Artículo en Inglés | MEDLINE | ID: mdl-16076106

RESUMEN

A whole plant chloroform-methanol extract of the orchid Epidendrum rigidum inhibited radicle growth of Amaranthus hypochondriacus seedlings (IC50 = 300 microg/mL). Bioassay-guided fractionation furnished four phytotoxins, namely, gigantol (1), batatasin III (2), 2,3-dimethoxy-9,10-dihydrophenathrene-4,7-diol (9), and 3,4,9-trimethoxyphenanthrene-2,5-diol (11), along with the known flavonoids apigenin, vitexin, and isovetin and the triterterpenoids 24,24-dimethyl-9,19-cyclolanostane-25-en-3beta-ol (14) and 24-methyl-9,19-cyclolanostane-25-en-3beta-ol (15). Stilbenoids 1, 2, 9, and 11 inhibited radicle growth of A. hypochondriacus with IC50 values of 0.65, 0.1, 0.12, and 5.9 microM, respectively. Foliar application of gigantol (1) at 1 microM to 4 week old seedlings of A. hypochondriacus reduced shoot elongation by 69% and fresh weight accumulation by 54%. Bibenzyls 1 and 2, as well as synthetic analogues 4'-hydroxy-3,3',5-trimethoxybibenzyl (3), 3,3',4',5-tetramethoxybibenzyl (4), 3,4'-dihydroxy-5-methoxybibenzyl (5), 3'-O-methylbatatasin III (6), 3,3',5-trihydroxybibenzyl (7), and 3,4',5-trihydroxybibenzyl (8), were tested for phytotoxicity in axenic cultures of the small aquatic plant Lemna pausicostata. All bibenzyls derivatives except 7 and 8 inhibited growth and increased cellular leakage with IC50 values of 89.9-180 and 89.9-166 microM, respectively. The natural and synthetic bibenzyls showed marginal cytotoxicity on animal cells. The results suggest that orchid bibenzyls may be good lead compounds for the development of novel herbicidal agents.


Asunto(s)
Bibencilos/farmacología , Herbicidas/farmacología , Orchidaceae/química , Amaranthus/efectos de los fármacos , Araceae/efectos de los fármacos , Bibencilos/aislamiento & purificación , Fraccionamiento Químico , Guayacol/análogos & derivados , Guayacol/farmacología , Herbicidas/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Plantones/efectos de los fármacos , Estilbenos/farmacología
14.
J Nat Prod ; 68(6): 959-62, 2005 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-15974630

RESUMEN

Activity-directed fractionation of a CH(2)Cl(2)-MeOH (1:1) extract of Hofmeisteria schaffneri led to the isolation of a new phytotoxin characterized as 2'-(2' '-hydroxy-4' '-methylphenyl)-2'-oxoethyl acetate and designated the trivial name of hofmeisterin (1). In addition, the known compounds beta-carotene, euparin, and 3',4',4a',9a'-tetrahydro-6,7'-dimethylspiro[benzofuran-3(2H),2'-pyrano[2,3-b]benzofuran]-2,4a'-diol (2) were obtained. The identification of the isolates was accomplished by spectroscopic methods. The structure of 1 was unequivocally confirmed by synthesis. The methyl derivative 1a was also synthesized following the same strategy. Compounds 1 and 2 inhibited radicle growth of Amaranthus hypochondriacus (IC(50) = 3.2 x 10(-4) and 1.2 x 10(-5) M, respectively) and significantly inhibited activation of the calmodulin (CaM)-dependent enzyme cAMP phosphodiesterase (PDE) with IC(50) values of 4.4 and 4.22 microM, respectively.


Asunto(s)
3',5'-AMP Cíclico Fosfodiesterasas/antagonistas & inhibidores , Asteraceae/química , Inhibidores Enzimáticos/aislamiento & purificación , Fenoles/aislamiento & purificación , Plantas Medicinales/química , Amaranthus/efectos de los fármacos , Amaranthus/crecimiento & desarrollo , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Concentración 50 Inhibidora , México , Estructura Molecular , Fenoles/química , Fenoles/farmacología
15.
Heredity (Edinb) ; 94(1): 64-70, 2005 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-15316559

RESUMEN

Recent studies have confirmed that weedy Amaranthus species are capable of interspecific hybridization, and such hybridization may foster the evolution of herbicide resistance. However, the extent to which hybridization among these species occurs in nature is unknown. The purpose of this study was to determine the frequency under field conditions at which A. hybridus, a monoecious and predominantly self-pollinated species, would be pollinated by A. tuberculatus, a dioecious species. To do this, parents carrying different alleles at the ALS locus, which encodes a herbicide target site, were used. Male A. tuberculatus parents were homozygous for a dominant herbicide-insensitive allele, while A. hybridus parents were homozygous for a sensitive form. Hybrid progeny therefore could be detected via herbicide selection. Mean hybridization frequencies between 0.4 and 2.3% were obtained, depending on the proximity between parents (P=0.02). The robustness of the hybrid selection assay was verified using a molecular marker and DNA content analyses. Using these techniques, more than 99% of the progeny that survived the herbicide were confirmed to be hybrids. Frequencies obtained in this study were many times higher than the generally expected rate of mutation. Therefore, even minimal fertility in hybrid progeny would support the view that hybridization could play a role in adaptive evolution of weedy Amaranthus species.


Asunto(s)
Amaranthus/metabolismo , Fertilidad/genética , Genes de Plantas/fisiología , Hibridación Genética , Polen/fisiología , Selección Genética , Adaptación Fisiológica , Alelos , Amaranthus/efectos de los fármacos , Amaranthus/genética , Evolución Biológica , Quimera , ADN de Plantas/genética , ADN de Plantas/metabolismo , Genes Dominantes , Herbicidas/farmacología , Homocigoto , Mutación , Plantas Modificadas Genéticamente
16.
Z Naturforsch C J Biosci ; 59(11-12): 803-10, 2004.
Artículo en Inglés | MEDLINE | ID: mdl-15666538

RESUMEN

The sesquiterpene lactone glaucolide B (1), isolated from Vernonia fruticulosa (Asteraceae), was transformed into six lactones (2-7). The structures of the products were elucidated by spectroscopic analysis. A series of solutions of compounds 1-7, at 200 microM, were tested on the germination and on the root and shoot growth of the dicotyledons Physalis ixocarpa and Trifolium alexandrinum and of the monocotyledons Lolium multiflorum and Amaranthus hypochondriacus. Lactone 5 exhibited clear selectivity towards dicotyledonous species at 200 microM, with an average inhibition of 90% on the germination of P. ixocarpa. Lactones 1, 3 and 4 had a greater effect on root length of monocotyledonous species, inhibiting around 70% at 200 microM in L. multiflorum. It seems that the diol function is required in lactones 4-6 to increase the activity, the polarity in the molecule might be required to reach its target.


Asunto(s)
Lactonas/aislamiento & purificación , Extractos Vegetales/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Vernonia/química , Amaranthus/efectos de los fármacos , Germinación/efectos de los fármacos , Lactonas/química , Lactonas/farmacología , Lolium/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/aislamiento & purificación , Raíces de Plantas/efectos de los fármacos , Raíces de Plantas/crecimiento & desarrollo , Brotes de la Planta/efectos de los fármacos , Brotes de la Planta/crecimiento & desarrollo , Semillas/efectos de los fármacos , Semillas/fisiología , Sesquiterpenos/química , Trifolium/efectos de los fármacos
17.
Phytochemistry ; 64(1): 285-91, 2003 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-12946427

RESUMEN

Bioassay-directed fractionation of a CH(2)Cl(2)-MeOH (1:1) extract of the aerial parts of Flourensia cernua led to the isolation of three phytotoxic compounds, namely, dehydroflourensic acid (1), flourensadiol (2) and methyl orsellinate (3). Dehydroflourensic acid is a new natural product whose structure was established by spectral means. In addition, the known flavonoid ermanin and seven hitherto unknown gamma-lactones were obtained, these being tetracosan-4-olide, pentacosan-4-olide, hexacosan-4-olide, heptacosan-4-olide, octacosan-4-olide, nonacosan-4-olide, and triacontan-4-olide. Compounds 1-3 caused significant inhibition of radicle growth of Amaranthus hypochondriacus and Echinochloa crus-galli, interacted with bovine-brain calmodulin and inhibited the activation of the calmodulin-dependent enzyme cAMP phosphodiesterase.


Asunto(s)
Amaranthus/efectos de los fármacos , Asteraceae/química , Echinochloa/efectos de los fármacos , Inhibidores Enzimáticos/aislamiento & purificación , Inhibidores Enzimáticos/farmacología , 3',5'-AMP Cíclico Fosfodiesterasas/antagonistas & inhibidores , Amaranthus/crecimiento & desarrollo , Animales , Calmodulina/antagonistas & inhibidores , Bovinos , Fosfodiesterasas de Nucleótidos Cíclicos Tipo 1 , Echinochloa/crecimiento & desarrollo , Inhibidores Enzimáticos/química , Cromatografía de Gases y Espectrometría de Masas , Concentración 50 Inhibidora , Estructura Molecular , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Plantas Tóxicas/química
18.
Commun Agric Appl Biol Sci ; 68(4 Pt A): 373-80, 2003.
Artículo en Inglés | MEDLINE | ID: mdl-15149132

RESUMEN

Considering the effect of crop-weed competition the rate of weed growing, the competitiveness of the occurring weed species and the duration of competition are determining factors. Experiments were carried out on fields in order to collect data on the effect of early weed competition on maize, including the competition for nutrients and the possible rate of nutrient removal by weeds. From 7 sampling areas of the 9.2 ha field weeds and maize samples were collected 1 month after the sowing of maize. We determined the total numbers and the species numbers of weeds by plots. The removed plant species and maize were weighed then dried until the weight balance was reached. The samples were tested for N, P, K and Ca. Comparison was done with the weight and nutrient element content of maize plants taken from the treated, weed-free area. At the same time comparative analyses were made with the mass and nutrient contents of maize plants. There were 12 occurring weed species in this experiment. Based on the rate of weed cover the following species were dominant: Datum stramonium L., Cannabis sativa L., Amaranthus chlorostachis Willd., Chenopodium album L., Chenopodium hybridum L. Our experiments revealed that in the areas being likely to produce high weed populations and showing a considerable high nutrient removal by weeds, the competition between weed plants and maize occurs at an earlier stage of the vegetation period of maize than on fields with moderate weed populations. Weeds have utilised significant amount of nutrients which has been many fold of maize in case of unit area.


Asunto(s)
Productos Agrícolas/crecimiento & desarrollo , Herbicidas/farmacología , Zea mays/crecimiento & desarrollo , Amaranthus/efectos de los fármacos , Amaranthus/crecimiento & desarrollo , Calcio/análisis , Cannabis/efectos de los fármacos , Cannabis/crecimiento & desarrollo , Chenopodium/efectos de los fármacos , Chenopodium/crecimiento & desarrollo , Datura/efectos de los fármacos , Datura/crecimiento & desarrollo , Nitrógeno/análisis , Fósforo/análisis , Potasio/análisis
19.
Pest Manag Sci ; 58(12): 1254-8, 2002 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-12477000

RESUMEN

Abstract: Field investigations were carried out during 1999 and 2000 to identify effective chemical/ cultural methods of weed control in rose-scented geranium (Pelargonium spp). The treatments comprised pre-emergence applications of oxyfluorfen (0.15, 0.20 and 0.25 kg AI ha(-1)) and pendimethalin (0.50, 0.75 and 1.00kg AI ha(-1)), successive hand weeding, hoeing and mulching using spent of lemon grass (at 5 tonnes ha(-1)) 45 days after planting (DAP), three hand-weedings 30, 60 and 90 DAP, weed-free (frequent manual weeding) and weedy control. Broad-leaf weeds were more predominant than grass and sedge weeds, accounting for 85.8% weed density and 93.0% weed dry weight in 1999 and 77.2% weed density and 93.9% weed dry weight in 2000. Unrestricted weed growth significantly reduced geranium oil yield, by 61.6% and 70.6% in 1999 and 2000, respectively. Pre-emergence application of pendimethalin (0.75-1.00 kgAI ha(-1)) or oxyfluorfen (0.25 kg AI ha(-1)), successive hand-weeding, hoeing and mulching and three hand-weedings were highly effective in reducing weed density and dry weight and gave oil yield comparable to the weed-free check. Application of oxyfluorfen (0.15 or 0.20 kg AI ha(-1)) and pendimethalin (0.50 kg AI ha(-1)) were less effective in controlling the weed species in geranium. None of the herbicides impaired the quality of rose-scented geranium oil measured in terms of citronellol and geraniol content.


Asunto(s)
Herbicidas/toxicidad , Pelargonium/crecimiento & desarrollo , Aceites de Plantas/metabolismo , Plantas/efectos de los fármacos , Monoterpenos Acíclicos , Aizoaceae/efectos de los fármacos , Amaranthus/efectos de los fármacos , Compuestos de Anilina/administración & dosificación , Compuestos de Anilina/química , Compuestos de Anilina/toxicidad , Chenopodium/efectos de los fármacos , Cyperus/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Éteres Difenilos Halogenados , Herbicidas/administración & dosificación , Herbicidas/química , Melilotus/efectos de los fármacos , Monoterpenos/metabolismo , Pelargonium/metabolismo , Éteres Fenílicos/administración & dosificación , Éteres Fenílicos/química , Éteres Fenílicos/toxicidad , Poaceae/efectos de los fármacos , Terpenos/metabolismo
20.
Pest Manag Sci ; 58(9): 981-4, 2002 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-12233193

RESUMEN

Mesotrione is a new callistemone herbicide that inhibits the HPPD enzyme (p-hydroxyphenylpyruvate dioxygenase) and introduces a new naturally selective tool into weed-management programmes for use in maize. Mesotrione provides control of the major broad-leaved weeds, and it can be used in integrated weed-management programmes depending on the grower's preferred weed-control strategy. At post-emergence rates of 150 g AI ha-1 or less, mesotrione provides naturally selective control of key species that may show triazine resistance (TR), e.g. Chenopodium album L, Amaranthus species, Solanum nigrum L, as well as species of weed that show resistance to acetolactase synthase (ALS) inhibitors e.g. Xanthium strumarium L, Amaranthus spp and Sonchus spp. The data presented show that resistant and susceptible biotypes of these species with resistance to triazine herbicides, such as atrazine, simazine, terbutylazine and metribuzin, or ALS-inhibitor herbicides, such as imazethepyr, remain susceptible to mesotrione. These results confirm that there is no cross-resistance in biotypes with target site resistance to triazine or ALS-inhibiting herbicides. It is important that herbicide choice and rotation becomes an integral part of planning weed management, so as to minimise the risks of crop losses from weed competition, build-up of weed seed in the soil and the further development of weed resistance across a range of herbicide modes of action.


Asunto(s)
Ciclohexanonas/farmacología , Resistencia a Medicamentos , Herbicidas/farmacología , Magnoliopsida/efectos de los fármacos , Zea mays , Agricultura , Amaranthus/efectos de los fármacos , Chenopodium/efectos de los fármacos , Ciclohexanonas/toxicidad , Herbicidas/toxicidad , Solanum/efectos de los fármacos
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