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1.
Nature ; 618(7963): 102-109, 2023 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-37225985

RESUMO

Parasitic nematodes are a major threat to global food security, particularly as the world amasses 10 billion people amid limited arable land1-4. Most traditional nematicides have been banned owing to poor nematode selectivity, leaving farmers with inadequate means of pest control4-12. Here we use the model nematode Caenorhabditis elegans to identify a family of selective imidazothiazole nematicides, called selectivins, that undergo cytochrome-p450-mediated bioactivation in nematodes. At low parts-per-million concentrations, selectivins perform comparably well with commercial nematicides to control root infection by Meloidogyne incognita, a highly destructive plant-parasitic nematode. Tests against numerous phylogenetically diverse non-target systems demonstrate that selectivins are more nematode-selective than most marketed nematicides. Selectivins are first-in-class bioactivated nematode controls that provide efficacy and nematode selectivity.


Assuntos
Antinematódeos , Tylenchoidea , Animais , Humanos , Antinematódeos/química , Antinematódeos/metabolismo , Antinematódeos/farmacologia , Caenorhabditis elegans/efeitos dos fármacos , Caenorhabditis elegans/metabolismo , Tylenchoidea/efeitos dos fármacos , Tylenchoidea/metabolismo , Tiazóis/química , Tiazóis/metabolismo , Tiazóis/farmacologia , Sistema Enzimático do Citocromo P-450/efeitos dos fármacos , Raízes de Plantas/efeitos dos fármacos , Raízes de Plantas/parasitologia , Doenças das Plantas , Especificidade da Espécie , Especificidade por Substrato
2.
Molecules ; 29(2)2024 Jan 16.
Artigo em Inglês | MEDLINE | ID: mdl-38257350

RESUMO

In the search for new alternative biocontrol strategies, phytopathogenic fungi could represent a new frontier for weed management. In this respect, as part of our ongoing work aiming at using fungal pathogens as an alternative to common herbicides, the foliar pathogen Nigrospora sphaerica has been evaluated to control buffelgrass (Cenchrus ciliaris). In particular, in this work, the isolation and structural elucidation of two new biosynthetically related metabolites, named nigrosphaeritriol (3-(hydroxymethyl)-2-methylpentane-1,4-diol) and nigrosphaerilactol (3-(1-hydroxyethyl)-4-methyltetrahydrofuran-2-ol), from the phytotoxic culture filtrate extract were described, along with the identification of several known metabolites. Moreover, the absolute stereochemistry of (3R,4S,5S)-nigrosphaerilactone, previously reported as (3S,4R,5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, was determined for the first time by X-ray diffraction analysis. Considering their structural relationship, the determination of the absolute stereochemistry of nigrosphaerilactone allowed us to hypothesize the absolute stereochemistry of nigrosphaeritriol and nigrosphaerilactol.


Assuntos
Ascomicetos , Cenchrus , Plantas Daninhas , Cristalografia por Raios X
3.
Am J Bot ; 107(6): 864-875, 2020 06.
Artigo em Inglês | MEDLINE | ID: mdl-32462674

RESUMO

PREMISE: Adaptive seed dispersal mechanisms are fundamental to plant fitness, but dispersal advantage is scale-dependent. We tested the hypothesis that informed dispersal in response to an environmental cue enables dispersal by wind on a local scale for Astragalus holmgreniorum, a desert species restricted to swales and wash skirts with overland flow, but prevents longer-distance dispersal by water into unfavorable wash habitats. METHODS: Pod biomechanics in A. holmgreniorum lead to major shape modifications with changes in moisture content. We performed laboratory experiments to examine the interaction of pod shape with wind and water, and conducted field experiments in A. holmgreniorum habitat evaluating the roles of wind, water, and seed predators on dispersal. RESULTS: Dry pods exhibit a flattened crescent shape with partial dehiscence that facilitated wind dispersal by ground tumbling and seed scattering in laboratory experiments. Rain simulation experiments showed that even small precipitation events returned wetted pods to their cylindrical shape and opened the dorsal suture, exposing the seeds. In the field experiments, dry pods were moved locally by wind, whereas rain caused pod opening and washing out of seeds in place. Seed predators had minimal effect on pod movement. CONCLUSIONS: Astragalus holmgreniorum exhibits pod structural remodeling in response to environmental change in a striking and novel demonstration of informed dispersal. Wind-driven movement of dry pods facilitates local seed dispersal, but rain causes pods to open and release seeds, ensuring that they are not transported out of suitable habitats and into active washes where they would be lost from the seed bank.


Assuntos
Astrágalo , Dispersão de Sementes , Ecologia , Ecossistema , Sementes , Navios
4.
Chirality ; 32(10): 1234-1242, 2020 10.
Artigo em Inglês | MEDLINE | ID: mdl-32691474

RESUMO

The fungal pathogen Pyricularia grisea has been studied to evaluate its production of phytotoxins for the biocontrol of the buffelgrass (Cenchrus ciliaris L.) weed. A first investigation allowed to isolate several new and known phytotoxic metabolites. However, the further investigation on the organic extract obtained from the fungus liquid culture showed the presence of other metabolites possibly contributing to its phytotoxicity. Thus, four known metabolites were isolated and identified by spectroscopic (nuclear magnetic resonance [NMR] and high-resolution electrospray ionization mass spectrometry [HRESIMS]) methods as dihydropyriculol (1), epi-dihydropyriculol (2), 3-methoxy-6,8-dihydroxy-3-methyl-3,4-dihydroisocoumarin (3), and (R)-mevalonolactone (4). The absolute configuration of 1-3 was determined for the first time by a computational analysis of their electronic circular dichroism (ECD) spectra. When the isolated compounds were bioassayed at a concentration of 5 × 10-3 M in a buffelgrass coleoptile and radicle elongation test no toxicity was detected. On the contrary, compounds 1 and 3 showed a significant stimulating effect of radical elongation. Furthermore, the difference in growth stimulation between 1 and its epimer 2 highlights the tight relationship between absolute configuration and biological activity of these fungal metabolites.


Assuntos
Cenchrus/microbiologia , Pyricularia grisea/metabolismo , Bioensaio , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Estrutura Molecular , Espectroscopia de Prótons por Ressonância Magnética , Espectrometria de Massas por Ionização por Electrospray , Estereoisomerismo
5.
Plant Dis ; 104(11): 2979-2985, 2020 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-32924874

RESUMO

Chia (Salvia hispanica L.) seeds are used for food, drinks, oil, and animal feed, and all plant parts are employed in traditional medicine. The growing demand for the seed has created a need for improved disease management. Plant-parasitic nematodes have been found on other Salvia spp., but none have been reported from S. hispanica. Chia has also not been tested for production of compounds active against these nematodes. Therefore, aqueous extracts from shoots and roots of six chia lines, Brad's Organic, Cono, E2, G3, G5, and W13.1, were tested in laboratory assays. Some concentrations of all extracts were nematotoxic, killing about one-third of Meloidogyne incognita (Kofoid & White) Chitwood second-stage juveniles (J2s) in shoot extracts and up to nearly half of J2s in root extracts. Hatch was generally not affected by the extracts. In greenhouse trials, all six chia lines were hosts of M. incognita. Chia line G3 had approximately two times or more eggs per gram of root than Brad's Organic or Cono. When cucumber seedlings were transplanted into soil amended with chopped chia shoots (2.3 or 2.5% weight of fresh shoots/weight of dry soil), galling and egg production on cucumber roots were not suppressed. To our knowledge, this is the first report that chia is a host to M. incognita (or any phytoparasitic nematode) and that chia shoots and roots produce compounds active against a nematode.


Assuntos
Cucumis sativus , Tylenchida , Tylenchoidea , Animais , Extratos Vegetais/farmacologia , Sementes
6.
J Nematol ; 52: 1-16, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32722901

RESUMO

Festulolium hybrids are forage grasses used worldwide in temperate climates. They are associated with the fungal endophyte Epichloë uncinata, which aids in nutrient uptake, drought tolerance, and production of metabolites that protect against parasites and herbivores. Epichloë uncinata produces loline alkaloids, which can deter insect pests. Festulolium has not been widely studied for susceptibility to plant-parasitic nematodes, so Festulolium lines, with and without fungal endophytes, were tested in the greenhouse for host status to the root-knot nematode Meloidogyne incognita. All were poor hosts, regardless of line or endophyte status. Pepper seedlings planted into soil following removal of the Festulolium plants were infected by nematodes, likely because of surviving nematodes from the original inoculation combined with some reproduction on Festulolium. Lolines were found in shoots and roots of all endophyte-associated lines, and some types of lolines in roots increased after nematode infection. Methanolic extracts from roots and shoots of a tested Festulolium line did not inhibit egg hatch, but killed nearly a third of second-stage juveniles whether an endophyte was present or not. Further studies would indicate whether these Festulolium lines aid in suppressing field populations of M. incognita.Festulolium hybrids are forage grasses used worldwide in temperate climates. They are associated with the fungal endophyte Epichloë uncinata, which aids in nutrient uptake, drought tolerance, and production of metabolites that protect against parasites and herbivores. Epichloë uncinata produces loline alkaloids, which can deter insect pests. Festulolium has not been widely studied for susceptibility to plant-parasitic nematodes, so Festulolium lines, with and without fungal endophytes, were tested in the greenhouse for host status to the root-knot nematode Meloidogyne incognita. All were poor hosts, regardless of line or endophyte status. Pepper seedlings planted into soil following removal of the Festulolium plants were infected by nematodes, likely because of surviving nematodes from the original inoculation combined with some reproduction on Festulolium. Lolines were found in shoots and roots of all endophyte-associated lines, and some types of lolines in roots increased after nematode infection. Methanolic extracts from roots and shoots of a tested Festulolium line did not inhibit egg hatch, but killed nearly a third of second-stage juveniles whether an endophyte was present or not. Further studies would indicate whether these Festulolium lines aid in suppressing field populations of M. incognita.

7.
J Exp Bot ; 70(19): 5487-5494, 2019 10 15.
Artigo em Inglês | MEDLINE | ID: mdl-31257433

RESUMO

Pyrenophoric acid (P-Acid), P-Acid B, and P-Acid C are three phytotoxic sesquiterpenoids produced by the ascomycete seed pathogen Pyrenophora semeniperda, a fungus proposed as a mycoherbicide for biocontrol of cheatgrass, an extremely invasive weed. When tested in cheatgrass bioassays, these metabolites were able to delay seed germination, with P-Acid B being the most active compound. Here, we have investigated the cross-kingdom activity of P-Acid B and its mode of action, and found that it activates the abscisic acid (ABA) signaling pathway in order to inhibit seedling establishment. P-Acid B inhibits seedling establishment in wild-type Arabidopsis thaliana, while several mutants affected in the early perception as well as in downstream ABA signaling components were insensitive to the fungal compound. However, in spite of structural similarities between ABA and P-Acid B, the latter is not able to activate the PYR/PYL family of ABA receptors. Instead, we have found that P-Acid B uses the ABA biosynthesis pathway at the level of alcohol dehydrogenase ABA2 to reduce seedling establishment. We propose that the fungus P. semeniperda manipulates plant ABA biosynthesis as a strategy to reduce seed germination, increasing its ability to cause seed mortality and thereby increase its fitness through higher reproductive success.


Assuntos
Ácido Abscísico/metabolismo , Arabidopsis/crescimento & desenvolvimento , Ascomicetos/fisiologia , Vias Biossintéticas , Germinação , Sesquiterpenos/metabolismo , Arabidopsis/microbiologia
8.
Plant Dis ; 103(9): 2191-2198, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31293210

RESUMO

Tea-oil camellia (Camellia oleifera) is grown for tea seed oil production, with tea seed cake produced as a byproduct. Rather than disposing of the cake, agricultural uses increase the value of oil production. Constituents of C. oleifera are also utilized for traditional Chinese medicine, as are compounds produced by tree peony roots. Consequently, the unused C. oleifera cake, and stems from two tree peony species, Paeonia rockii and Paeonia suffruticosa, were studied for compounds antagonistic to soybean cyst nematode (Heterodera glycines) and root-knot nematode (Meloidogyne incognita). Extracts from C. oleifera cake and P. rockii stems suppressed hatch and were nematotoxic to second-stage juveniles (J2) of both nematode species. P. rockii extracts were more effective than P. suffruticosa extracts for decreasing M. incognita hatch and J2 viability. In greenhouse trials with soybean (Glycine max 'Essex'), powdered C. oleifera cake applied as a soil amendment suppressed H. glycines cysts/g root by up to 66% compared with nonamended controls. These results indicate that the extracts and cake contain compounds active against H. glycines and M. incognita, with activity varying between the two Paeonia species. C. oleifera tea seed cake, and constituents of the cake or of P. rockii, are candidates for further studies on management of these nematodes.


Assuntos
Camellia , Paeonia , Extratos Vegetais , Tylenchoidea , Animais , Antinematódeos/farmacologia , Camellia/química , Paeonia/química , Extratos Vegetais/farmacologia , Sementes/química , Tylenchoidea/efeitos dos fármacos
9.
Molecules ; 24(15)2019 Jul 31.
Artigo em Inglês | MEDLINE | ID: mdl-31370299

RESUMO

Radicinin (1), is a fungal dihydropyranopyran-4,5-dione isolated together with some analogues, namely 3-epi-radicinin, radicinol, 3-epi-radicinol, and cochliotoxin (2-5), from the culture filtrates of the fungus Cochliobolus australiensis, a foliar pathogen of buffelgrass (Cenchrus ciliaris), an invasive weed in North America. Among the different metabolites 1 showed target-specific activity against the host plant and no toxicity on zebrafish embryos, promoting its potential use to develop a natural bioherbicide formulation to manage buffelgrass. These data and the peculiar structural feature of 1 suggested to carry out a structure-activity relationship study, preparing some key hemisynthetic derivatives and to test their phytotoxicity. In particular, p-bromobenzoyl, 5-azidopentanoyl, stearoyl, mesyl and acetyl esters of radicinin were semisynthesized as well as the monoacetyl ester of 3-epi-radicinin, the diacetyl esters of radicinol and its 3 epimer, and two hexa-hydro derivatives of radicinin. The spectroscopic characterization and the activity by leaf puncture bioassay against buffelgrass of all the derivatives is reported. Most of the compounds showed phytotoxicity but none of them had comparable or higher activity than radicinin. Thus, the presence of an α,ß unsaturated carbonyl group at C-4, as well as, the presence of a free secondary hydroxyl group at C-3 and the stereochemistry of the same carbon proved to be the essential feature for activity.


Assuntos
Cenchrus/efeitos dos fármacos , Plantas Daninhas/efeitos dos fármacos , Pironas/química , Relação Estrutura-Atividade , Alcaloides/química , Alcaloides/farmacologia , Ascomicetos/química , Cenchrus/crescimento & desenvolvimento , Fungos Mitospóricos/química , Estrutura Molecular , América do Norte , Plantas Daninhas/crescimento & desenvolvimento , Pironas/farmacologia , Toxinas Biológicas/química , Toxinas Biológicas/farmacologia
10.
Molecules ; 24(6)2019 Mar 19.
Artigo em Inglês | MEDLINE | ID: mdl-30893868

RESUMO

The fungal pathogens Cochliobolus australiensis and Pyricularia grisea have recently been isolated from diseased leaves of buffelgrass (Cenchrus ciliaris) in its North American range, and their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides against this invasive weed was investigated. Fourteen secondary metabolites obtained from in vitro cultures of these two pathogens were tested by leaf puncture assay on the host plant at different concentrations. Radicinin and (10S, 11S)-epi-pyriculol proved to be the most promising compounds. Thus, their phytotoxic activity was also evaluated on non-host indigenous plants. Radicinin demonstrated high target-specific toxicity on buffelgrass, low toxicity to native plants, and no teratogenic, sub-lethal, or lethal effects on zebrafish (Brachydanio rerio) embryos. It is now under consideration for the development of a target-specific bioherbicide to be used against buffelgrass in natural systems where synthetic herbicides cause excessive damage to native plants.


Assuntos
Cenchrus/efeitos dos fármacos , Herbicidas/imunologia , Herbicidas/farmacologia , Pironas/farmacologia , Animais , Benzaldeídos/farmacologia , Embrião não Mamífero/efeitos dos fármacos , Álcoois Graxos/farmacologia , Peixe-Zebra
11.
Molecules ; 23(7)2018 Jul 16.
Artigo em Inglês | MEDLINE | ID: mdl-30012966

RESUMO

A fungal pathogen soon to be described as Rutstroemia capillus-albis (Rutstroemiaceae, Helotiales, Leotiomycetes) has been identified as the causal agent of 'bleach blonde syndrome' on the invasive annual grass weed Bromus tectorum (cheatgrass) in western North America. This apparently common but previously undescribed disease causes premature senescence and sterility, but does not affect seed germination or seedling emergence and growth. This study investigated whether the new species produces phytotoxins that could be implicated in pathogenesis. The compounds 9-O-methylfusarubin, 9-O-methylbostrycoidin, 5-O-methylnectriafurone, trans-methyl-p-coumarate and terpestacin were isolated from the solid culture of this fungus. The undescribed absolute stereochemistry at C-3 of 9-O-methylfusarubin and at C-1' of 5-O-methylnectriafurone were assigned by applying electronic and vibrational circular dichroism (ECD and VCD) combined with computational methods and the advanced Mosher's method, respectively. The first three listed compounds are naphtoquinone pigments, while terpestacin is a sesterterpene, and trans-methyl-p-coumarate could be the product of an unusual fungal phenylpropanoid biosynthesis pathway. In a juvenile plant immersion bioassay, both 9-O-methylfusarubin and terpestacin proved to be highly toxic at 10-4 M, causing wilting and plant death within 10 days. This finding suggests that these two compounds could play a role in pathogenesis on B. tectorum.


Assuntos
Ascomicetos , Bromus/microbiologia , Doenças das Plantas/microbiologia , Ascomicetos/química , Ascomicetos/isolamento & purificação , Ascomicetos/metabolismo , Compostos Bicíclicos com Pontes/química , Compostos Bicíclicos com Pontes/metabolismo , Quinonas/química , Quinonas/metabolismo
12.
J Nematol ; 50(2): 147-162, 2018 Sep 03.
Artigo em Inglês | MEDLINE | ID: mdl-30451435

RESUMO

Vetiver, a nonhost grass for certain nematodes, was studied for the production of compounds active against the southern root-knot nematode, Meloidogyne incognita . In laboratory assays studying the effects on second-stage juvenile (J2) activity and viability, crude vetiver root and shoot extracts were nematotoxic, resulting in 40% to 70% J2 mortality, and were also repellent to J2. Vetiver oil did not exhibit activity against J2 in these assays. Gas chromatography-mass spectrometry analyses of three crude vetiver root ethanol extracts and a commercial vetiver oil determined that two of the major components in each sample were the sesquiterpene acid 3,3,8,8-tetramethyltricyclo[5.1.0.0(2,4)]oct-5-ene-5-propanoic acid and the sesquiterpene alcohol 6-isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-2-ol. The acid was present in higher amounts in the extracts than in the oil. These studies demonstrating nematotoxicity and repellency of vetiver-derived compounds to M. incognita suggest that plant chemistry plays a role in the nonhost status of vetiver to root-knot nematodes, and that the chemical constituents of vetiver may be useful for suppressing nematode populations in the soil.

13.
Am J Bot ; 104(6): 879-890, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28634255

RESUMO

PREMISE OF THE STUDY: Invasive species are often initially restricted to a narrow range and may then expand through any of multiple mechanisms including phenotypic plasticity, in situ evolution, or selection on traits preadapted for new habitats. Our study used population genetics to explore possible processes by which the highly selfing invasive annual grass Bromus tectorum has expanded into montane environments. METHODS: We used 69 single nucleotide polymorphic (SNP) markers to genotype ca. 20 individuals from each of 38 montane cheatgrass populations from throughout the Intermountain West and to identify characteristic SNP haplotypes and examine their distribution. KEY RESULTS: Five invariant SNP haplotypes were dominant in montane cheatgrass populations, making up 59% of genotyped individuals, with each haplotype present in 12 to 21 populations. Four of these were absent or present at low frequency in low elevation populations, while the fifth was also sometimes dominant at low elevation. Sixteen haplotypes made up 78% of all genotyped individuals. These haplotypes were distributed across several haplogroups within the clade that also includes most sagebrush steppe lineages. CONCLUSIONS: The wide geographic distribution of several common haplotypes almost completely restricted to montane habitats suggests that dominant lineages in montane populations may possess adaptive syndromes that are preserved through reduced outcrossing rates or negative selection on outcrossed progeny. However, conclusive evidence of such local adaptation requires reciprocal seeding experiments and further characterization of adaptive traits and breeding system characteristics. Other lineages have likely risen to dominance in montane populations through selectively neutral processes.


Assuntos
Bromus/genética , Genética Populacional , Espécies Introduzidas , Ecossistema , Haplótipos , América do Norte , Polimorfismo de Nucleotídeo Único
14.
J Nat Prod ; 80(10): 2771-2777, 2017 10 27.
Artigo em Inglês | MEDLINE | ID: mdl-29039952

RESUMO

The fungal pathogen Cochliobolus australiensis isolated from infected leaves of the invasive weed buffelgrass (Pennisetum ciliare) was grown in vitro to evaluate its ability to produce phytotoxic metabolites that could potentially be used as natural herbicides against this weed. Two new tetrasubstituted 3-chromanonacrylic acids, named chloromonilinic acids C (1) and D (2), were isolated from the liquid cultures of C. australiensis, together with the known chloromonilinic acid B. Chloromonilinic acids C and D were characterized by spectroscopic and chemical methods as (E)-3-chloro-3-[(5-hydroxy-3-(1-hydroxy-2-methoxy-2-oxoethyl)-7-methyl-4-oxo-4H-chromen-2-yl)]acrylic acid and (Z)-3-chloro-3-[(5-hydroxy-3-(2-methoxy-2-oxoethyl)-7-methyl-4-oxo-4H-chromen-2-yl)]acrylic acid, respectively. The stereochemistry of chloromonilinic acids C and D was determined using a combination of spectroscopic and computational methods, including electronic circular dichroism. The fungus produced these compounds in two different liquid media together with cochliotoxin, radicinin, radicinol, and their 3-epimers. The radicinin-related compounds were also produced when the fungus was grown in wheat seed solid culture, but chloromonilinic acids were not found in the solid culture organic extract. All three chloromonilinic acids were toxic to buffelgrass in a seedling elongation bioassay, with significantly delayed germination and dramatically reduced radicle growth, especially at a concentration of 5 × 10-3 M.


Assuntos
Ascomicetos/química , Benzopiranos/isolamento & purificação , Benzopiranos/farmacologia , Herbicidas/farmacologia , Alcaloides/metabolismo , Benzopiranos/química , Cenchrus , Germinação , Herbicidas/química , Herbicidas/isolamento & purificação , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/microbiologia , Pironas/química , Sementes/metabolismo , Texas , Triticum/microbiologia
15.
J Nat Prod ; 80(5): 1241-1247, 2017 05 26.
Artigo em Inglês | MEDLINE | ID: mdl-28422495

RESUMO

Buffelgrass (Pennisetum ciliare or Cenchrus ciliaris) is a perennial grass that has become highly invasive in the Sonoran Desert of southern Arizona. In the search for novel control strategies against this weed, strains of the foliar fungal pathogen Cochliobolus australiensis from buffelgrass have been screened for their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides in an integrated pest management strategy. A new phytotoxin, named cochliotoxin, was isolated from liquid culture of this fungus together with radicinin, radicinol, and their 3-epimers. Cochliotoxin was characterized, essentially by spectroscopic methods, as 3-hydroxy-2-methyl-7-(3-methyloxiranyl)-2,3-dihydropyrano[4,3-b]pyran-4,5-dione. Its relative stereochemistry was assigned by 1H NMR techniques, while the absolute configuration (2S,3S) was determined applying the advanced Mosher's method by esterification of its hydroxy group at C-3. When bioassayed in a buffelgrass coleoptile elongation test and by leaf puncture bioassay against the host weed and two nontarget grasses, cochliotoxin showed strong phytotoxicity. In the same tests, radicinin and 3-epi-radicinin also showed phytotoxic activity, while radicinol and 3-epi-radicinol were largely inactive. All five compounds were more active in leaf puncture bioassays on buffelgrass than on the nontarget grass tanglehead (Heteropogon contortus), while the nontarget grass Arizona cottontop (Digitaria californica) was more sensitive to radicinin and 3-epi-radicinin. Cochliotoxin at low concentration was significantly more active on buffelgrass than on either native grass, but the difference was small.


Assuntos
Ascomicetos/química , Cenchrus/química , Herbicidas/isolamento & purificação , Herbicidas/farmacologia , Fungos Mitospóricos/isolamento & purificação , Micotoxinas/isolamento & purificação , Micotoxinas/farmacologia , Folhas de Planta/química , Poaceae/química , Pironas/química , Pironas/isolamento & purificação , Pironas/farmacologia , Arizona , Ascomicetos/isolamento & purificação , Herbicidas/química , Fungos Mitospóricos/química , Estrutura Molecular , Micotoxinas/química
16.
Chirality ; 29(11): 726-736, 2017 11.
Artigo em Inglês | MEDLINE | ID: mdl-28902437

RESUMO

Pyricularia grisea has been identified as a foliar pathogen on buffelgrass (Cenchrus ciliaris) in North America and was studied as a potential source of phytotoxins for buffelgrass control. Two monosubstituted hex-4-ene-2,3-diols, named pyriculins A and B, were isolated from its culture filtrate organic extract together with (10S,11S)-(-)-epipyriculol, trans-3,4-dihydro-3,4,8-trihydroxy-1(2H)-napthalenone, and (4S)-(+)-isosclerone. Pyriculins A and B were characterized by spectroscopic (essentially nuclear magnetic resonance [NMR], High-resolution electrospray ionization mass spectrometry [HRESIMS]) and chemical methods such as (4E)-1-(4-hydroxy-1,3-dihydroisobenzofuran-1-yl)hex-4-ene-2,3-diols. The relative and absolute configuration of these compounds was determined by a combination of spectroscopic (NMR, electronic circular dichroism [ECD]) and computational tools. When bioassayed in a buffelgrass coleoptile and radicle elongation test, (10S,11S)-(-)-epipyriculol proved to be the most toxic compound. Seed germination was much reduced and slowed with respect to the control and radicles failed to elongate. All five compounds delayed germination, but only (10S,11S)-(-)-epipyriculol was able to prevent radicle development of buffelgrass seedlings. It had no effect on coleoptile elongation, while the other four compounds caused significantly increased coleoptile development relative to the control.


Assuntos
Cenchrus/microbiologia , Glicóis/química , Glicóis/metabolismo , Pyricularia grisea/metabolismo , Glicóis/toxicidade , Pyricularia grisea/fisiologia
17.
Echocardiography ; 33(3): 406-15, 2016 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-26498324

RESUMO

BACKGROUND: Trastuzumab has substantially improved overall survival and reduced the risk of disease recurrence in patients with human epidermal growth factor receptor type II (HER-II)-positive breast cancer. However, this benefit may be at the increased risk of cardiotoxicity. We aimed to explore the early subclinical left and right ventricular as well as atrial dysfunction, in trastuzumab-treated patients with HER-II-positive breast cancer, using velocity vector imaging. METHODS: Echocardiography images were acquired in 50 patients with HER-II-positive breast cancer undergoing trastuzumab therapy. All patients had baseline and 3-6 months and 12-15 months of follow-up echocardiograms after initiation of trastuzumab therapy. Subendocardial borders of all the cardiac chambers were traced from the apical views to obtain volumetric and deformation indices. RESULTS: Mean age was 60 ± 13 years. Left ventricular (LV) ejection fraction as well as conventional indices of right ventricular (RV) function did not change with trastuzumab. The RV peak systolic global longitudinal strain (GLε) significantly decreased (-24.53 ± 6.03 vs. -21.28 ± 5.11 vs. -21.84 ± 5.15, baseline vs. first and second follow-ups, P = 0.01). LV peak systolic GLε was reduced by 1.19 at early follow-up (P < 0.05). Left atrial reservoir and booster pump functions as well as right atrial reservoir function were reduced through follow-up as well. CONCLUSIONS: The RV exhibited greater change in strain after trastuzumab treatment when compared to the LV. Atria function was reduced by trastuzumab as well. The repercussion of these findings and their potential implication will warrant further study.


Assuntos
Neoplasias da Mama/tratamento farmacológico , Ecocardiografia/métodos , Trastuzumab/administração & dosagem , Trastuzumab/efeitos adversos , Disfunção Ventricular/induzido quimicamente , Disfunção Ventricular/diagnóstico por imagem , Adulto , Idoso , Idoso de 80 Anos ou mais , Antineoplásicos/administração & dosagem , Antineoplásicos/efeitos adversos , Neoplasias da Mama/diagnóstico por imagem , Neoplasias da Mama/metabolismo , Feminino , Átrios do Coração/diagnóstico por imagem , Átrios do Coração/efeitos dos fármacos , Humanos , Aumento da Imagem/métodos , Interpretação de Imagem Assistida por Computador/métodos , Pessoa de Meia-Idade , Receptor ErbB-2/metabolismo , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Volume Sistólico/efeitos dos fármacos , Resultado do Tratamento
18.
Chem Biodivers ; 13(9): 1165-1177, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27450661

RESUMO

In our continuing effort to discover natural product-based pest management agents, derivatives of 3,5-dimethoxystilbene were synthesized yielding 27 new and six known compounds. Compounds 11 and 12 showed strong Aedes aegypti larvicidal activity (LC50 45.31 and 49.93 µm, respectively). Furthermore, 11 and 12 exhibited high effectiveness against larvae of pesticide-susceptible and pyrethroid-resistant strains of Ae. aegypti; activity against the adult mosquitoes was low. Compounds 6f, 6g, and 6i at either 83.3 or 166.7 µg/ml reduced the mobility of second-stage juveniles (J2) of the root-knot nematode (Meloidogyne incognita) that hatched from eggs immersed in the test compounds for 7 days. However, there was little or no effect on J2 placed directly into these compounds, and none of the analogs suppressed M. incognita egg hatch. The compounds were tested for inhibition of some agriculturally important fungi; 6a, 7a, and 7e demonstrated strong inhibition of Colletotrichum species. Activity of the stilbenes against some human pathogens was also explored; 11, 12, and 16 showed moderate inhibitory activity against Cryptococcus neoformans, Staphylococcus aureus, methicillin-resistant S. aureus, and Mycobacterium intracellulare. Except for 11 and 12, which were active against mosquito larvae and some human pathogens, no single analog demonstrated activity in all the tests, indicating specific activities. Synthesis of the analogs and structure-activity relationships are discussed.


Assuntos
Aedes/efeitos dos fármacos , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Inseticidas/farmacologia , Estilbenos/farmacologia , Animais , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/síntese química , Antifúngicos/química , Bactérias/efeitos dos fármacos , Relação Dose-Resposta a Droga , Fungos/efeitos dos fármacos , Inseticidas/síntese química , Inseticidas/química , Larva/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Estilbenos/síntese química , Estilbenos/química , Relação Estrutura-Atividade
19.
J Nematol ; 48(1): 43-53, 2016 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-27168652

RESUMO

Pseudomonas fluorescens isolates Clinto 1R, Wayne 1R, and Wood 1R, which produce the antibiotic 2,4-diacetylphloroglucinol (DAPG), can suppress soilborne diseases and promote plant growth. Consequently, these beneficial bacterial isolates were tested on watermelon plants for suppression of Meloidogyne incognita (root-knot nematode: RKN) and Fusarium oxysporum f. sp. niveum (Fon). In a greenhouse trial, Wayne 1R root dip suppressed numbers of RKN eggs per gram root on 'Charleston Gray' watermelon by 28.9%. However, in studies focused on 'Sugar Baby' watermelon, which is commercially grown in Maryland, a Wayne 1R root dip did not inhibit RKN reproduction or plant death caused by Fon. When all three isolates were applied as seed coats, plant stand in the greenhouse was reduced up to 60% in treatments that included Fon ± P. fluorescens, and eggs per gram root did not differ among treatments. In a microplot trial with Clinto 1R and Wayne 1R root dips, inoculation with P. fluorescens and/or Fon resulted in shorter vine lengths than treatment with either P. fluorescens isolate plus RKN. Root weights, galling indices, eggs per gram root, and second-stage juvenile (J2) numbers in soil were similar among all RKN-inoculated treatments, and fruit production was not affected by treatment. Plant death was high in all treatments. These studies demonstrated that the tested P. fluorescens isolates resulted in some inhibition of vine growth in the field, and were not effective for enhancing plant vigor or suppressing RKN or Fon on watermelon.

20.
Am J Bot ; 102(10): 1666-75, 2015 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-26451036

RESUMO

PREMISE OF THE STUDY: The evolutionary drivers and proximal regulators of mast-seeding are well understood for species of mesic environments, but how these regulators interact with high spatial and interannual variability in growing-season precipitation for a masting species in a desert environment has never been examined. METHOD: We followed flowering and seed production in 16 populations of the North American desert shrub blackbrush (Coleogyne ramosissima) from contrasting environments across its range over an 11-year period to determine patterns of interannual reproductive output variation. KEY RESULT: Patterns of reproductive output in blackbrush did not track current growing season precipitation, but instead were regulated by prior-year weather cues. The strength of the response to the masting cue depended on habitat quality, with higher mean reproductive output, shorter intervals between years of high seed production, and lower CVp at more favorable sites. Wind pollination efficiency was demonstrated to be an important evolutionary driver of masting in blackbrush, and satiation of heteromyid seed predator-dispersers was supported as an evolutionary driver based on earlier studies. CONCLUSIONS: Both the evolutionary drivers and proximal regulators of masting in blackbrush are similar to those demonstrated for masting species of mesic environments. Relatively low synchrony across populations in response to regional masting cues occurs at least partly because prior-year environmental cues can trigger masting efforts in years with resource limitation due to suboptimal precipitation, especially in more xeric low-elevation habitats.


Assuntos
Ecossistema , Rosaceae/fisiologia , Sementes/crescimento & desenvolvimento , Evolução Biológica , Flores/crescimento & desenvolvimento , Nevada , Rosaceae/crescimento & desenvolvimento , Estações do Ano , Utah
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