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1.
J Agric Food Chem ; 72(14): 7919-7932, 2024 Apr 10.
Artículo en Inglés | MEDLINE | ID: mdl-38554092

RESUMEN

Nine caffeoyl derivatives (1-9), including two new dicaffeoyl glycosides, brevicaudatosides A and B (1 and 2), and six flavonoids (10-15), were identified from overground Clematis brevicaudata DC. Compounds 1 and 13 exhibited significant oral toxicities against Acyrthosiphon pisum Harris with LC50 (half-lethal concentration) values of 0.12 and 0.28 mM, respectively. Meanwhile, compounds 1, 8, 10, 13, and 15 showed remarkable repellent effects against A. pisum with the repellent indexes valued at 1.00 under 50-200 µg/mL at 24 h. Compounds 1 and 8 also displayed moderate antifeedant activities against Plutella xylostella L. The shrunken bodies, especially for wizened cauda, and the ultrastructural damages of microvilli, mitochondrion, nucleus, and endoplasmic reticulum in midgut were toxic symptoms of A. pisum caused by 1 and 13. The inhibition of Chitinase was the main reason for their potent insecticidal activities. This study provided valuable pieces of evidence for the high value-added application of caffeoyl and flavonoid derivatives from C. brevicaudata as novel plant-origin biopesticides for crop protection.


Asunto(s)
Productos Biológicos , Clematis , Insecticidas , Mariposas Nocturnas , Animales , Insecticidas/farmacología , Insecticidas/química , Clematis/química , Flavonoides/farmacología , Productos Biológicos/farmacología , Protección de Cultivos
2.
J Agric Food Chem ; 72(9): 4596-4609, 2024 Mar 06.
Artículo en Inglés | MEDLINE | ID: mdl-38385330

RESUMEN

To discover new botanical products-based insecticide candidates, 14 triterpenoid saponins (1-14) including four new ones, obscurosides A-D (1-4), were isolated from Clematis obscura Maxim as potential agrochemicals against Acyrthosiphon pisum Harris and Plutella xylostella (L.). Compounds 1-3 were characterized by a rare ribose substitution at C-3, and 4 was a bidesmoside glycosylated at the rare C-23 and C-28 positions of the oleanane aglycone. Compounds 10 (median antifeeding concentration, AFC50 = 1.10 mg/mL; half-lethal concentration, LC50 = 1.21 mg/mL) and 13 (AFC50 = 1.09 mg/mL, LC50 = 1.37 mg/mL) showed significant insecticidal activities against third larvae of P. xylostella at 72 h. All saponins displayed antifeedant activities against A. pisum with the deterrence index of 0.20-1.00 at 400 µg/mL. Compound 8 showed optimal oral toxicity (LC50 = 50.09 µg/mL) against A. pisum, followed by compounds 1, 5-7, 9, and 14 (LC50 = 90.21-179.25 µg/mL) at 72 h. The shrinkage of the cuticle and the destruction of intestinal structures of microvilli, nucleus, endoplasmic reticulum, and mitochondria were toxic symptoms of 8-treated A. pisum. The significantly declined Chitinase activity in 8-treated A. pisum with an inhibition rate of 79.1% at LC70 (70% lethal concentration) could be the main reason for its significant oral toxicities. Molecular docking revealed favorable affinities of compounds 1 and 8 with group I Chitinase OfChtI (Group I Chitinase from Ostrinia furnacalis) through conventional hydrogen bonds and alkey/π-alkey interactions by different patterns. These results will provide valuable information for the development of novel botanical pesticides for the management of insect pests, especially against A. pisum.


Asunto(s)
Áfidos , Quitinasas , Clematis , Insecticidas , Mariposas Nocturnas , Saponinas , Animales , Insecticidas/química , Saponinas/química , Clematis/química , Pisum sativum , Simulación del Acoplamiento Molecular , Larva
3.
J Agric Food Chem ; 72(5): 2624-2633, 2024 Feb 07.
Artículo en Inglés | MEDLINE | ID: mdl-38277222

RESUMEN

Pseudomonas syringae pv. actinidiae (Psa) is a significant pathogenic bacterium affecting the kiwifruit industry. This study investigated the target sites of streptothricin-F (ST-F), produced by Streptomyces lavendulae gCLA4. The inhibition of ST-F on Psa was examined by the microscopic structural differences of Psa before and after treatment with ST-F, as well as the interaction between ST-F and cell division-related proteins. The results revealed filamentation of Psa after ST-F treatment, and fluorescence microscopy showed that ST-F inhibited the formation of the Z-ring composed of FtsZ protein. In vitro experiments and molecular docking demonstrated that ST-F can bind to FtsZ with a binding energy of 0.4 µM and inhibit FtsZ's GTP-dependent polymerization reaction. In addition, ST-F does not exert inhibitory effects on cell division in Psa strains overexpressing ftsZ. In conclusion, FtsZ is one of the target sites for ST-F inhibition of Psa, highlighting its potential as a therapeutic target for controlling Psa-induced kiwifruit bacterial canker.


Asunto(s)
Actinidia , Estreptotricinas , Estreptotricinas/farmacología , Pseudomonas syringae , Simulación del Acoplamiento Molecular , Enfermedades de las Plantas/microbiología , Actinidia/microbiología
4.
ACS Appl Bio Mater ; 7(1): 297-305, 2024 Jan 15.
Artículo en Inglés | MEDLINE | ID: mdl-38103174

RESUMEN

Iron oxide nanoparticles (Fe3O4 NPs) have been reported to be a promising agent for cancer therapy due to their outstanding ability in catalyzing the Fenton reaction and causing peroxidation. Generally, particles with size of hundreds of nanometers exhibit enhanced accumulation in tumor due to the enhanced permeation and retention effect. However, the large size hinders penetration within the dense collagen matrix. Here, we propose a multistage system to realize pH-responsive size switch for efficient drug delivery. In this system, ultrasmall Fe3O4 (∼4 nm) NPs are simultaneously modified with hydrophilic mPEG and hydrophobic N,N-dibutylethylenediamine (DBE) to form pH-responsive self-assembled iron oxide aggregations (SIOA). In the acidic tumor microenvironment, the protonation of DBE makes it transit from the hydrophobic to hydrophilic state, causing the disassembly of the SIOA and the release of loaded doxorubicin. The multistage Fe3O4 NPs demonstrate enhanced accumulation and efficient diffusion within the tumor, holding a promise for drug delivery and cancer therapy.


Asunto(s)
Doxorrubicina , Compuestos Férricos , Neoplasias , Humanos , Doxorrubicina/química , Neoplasias/tratamiento farmacológico , Neoplasias/patología , Sistemas de Liberación de Medicamentos , Microambiente Tumoral
5.
Aquat Toxicol ; 265: 106763, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37980848

RESUMEN

Microcystins (MCs) are biologically active cyclic heptapeptide compounds released by cyanobacteria in water bodies, and MC-LR is one of the most widespread and toxic isoforms. It frequently poses a serious threat to Penaeus vannamei aquaculture. Our previous study revealed that the supplementation of Lactobacillus plantarum Ep-M17 has a probiotic effect on P. vannamei health and whether Ep-M17 can alleviate the stressful effects of MC-LR on shrimp remains unclear. Therefore, in the present work, shrimp were fed MC-LR alone or combined with Ep-M17 for six weeks, and then evaluated the effects on histology, enzyme activity, gene expression, and intestinal flora. The results showed that MC-LR stress lead to slow growth and reduced survival rates in shrimp. However, feeding Ep-M17 significantly increased both the growth rate and survival rate. Meanwhile, MC-LR stress caused severe tissue damage in the hepatopancreas and intestines of shrimp, but Ep-M17 significantly reduced the toxic effects and protected the integrity of these tissues. Additionally, Ep-M17 significantly enhanced the activities of antioxidant enzymes and digestive enzymes, and induced higher expression of immune-related genes, thereby promoting the digestive and immune responses in shrimp. Furthermore, MC-LR stress disrupted the intestinal flora in shrimp intestines, while the use of Ep-M17 significantly increased the abundance of immune- and metabolism-related bacteria and inhibited the growth of pathogenic bacteria to maintain intestinal flora balance and intestinal health. In conclusion, our results indicate that Ep-M17 can reduce the toxic effect of MC-LR on shrimp and has a positive function in the prevention and control of shrimp diseases caused by MC-LR.


Asunto(s)
Cianobacterias , Microbioma Gastrointestinal , Lactobacillus plantarum , Penaeidae , Contaminantes Químicos del Agua , Animales , Lactobacillus plantarum/metabolismo , Microcistinas/toxicidad , Microcistinas/metabolismo , Penaeidae/fisiología , Contaminantes Químicos del Agua/toxicidad , Cianobacterias/metabolismo
6.
Pest Manag Sci ; 79(11): 4357-4366, 2023 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-37417001

RESUMEN

BACKGROUND: Kiwifruit bacterial canker (KBC) caused by Pseudomonas syringae pv. actinidiae (Psa) is the main limiting factor in the kiwifruit industry. This study aimed to identify bacterial strains with antagonistic activity against Psa, analyze antagonistically active substances and provide a new basis for the biological control of KBC. RESULTS: A total of 142 microorganisms were isolated from the rhizosphere soil of asymptomatic kiwifruit. Among them, an antagonistic bacterial strain was identified as Paenibacillus polymyxa YLC1 by 16S rRNA sequencing. KBC control by strain YLC1 (85.4%) was comparable to copper hydroxide treatment (81.8%) under laboratory conditions and field testing. Active substances of strain YLC1 were identified by genetic sequence analysis using antiSMASH. Six biosynthetic active compound gene clusters were identified as encoding ester peptide synthesis, such as polymyxins. An active fraction was purified and identified as polymyxin B1 using chromatography, hydrogen nuclear magnetic resonance (NMR), and liquid chromatography-mass spectrometry. In addition, polymyxin B1 also was found significantly to suppress the expression of T3SS-related genes, but did not affect the growth of Psa at low concentrations. CONCLUSION: In this study, a biocontrol strain P. polymyxa YLC1 obtained from kiwifruit rhizosphere soil exhibited excellent control effects on KBC in vitro and in field tests. Its active compound was identified as polymyxin B1, which inhibits a variety of pathogenic bacteria. We conclude that P. polymyxa YLC1 is a biocontrol strain with excellent prospects for development and application. © 2023 Society of Chemical Industry.

7.
J Nat Prod ; 86(7): 1855-1861, 2023 07 28.
Artículo en Inglés | MEDLINE | ID: mdl-37368408

RESUMEN

Two new caulamidines C (2) and D (4) and three isocaulamidines B, C, and D (1, 3, and 5) along with the known compound caulamidine B (6) were isolated from the marine ascidian Polyandrocarpa sp. Their structures were elucidated by analysis of nuclear magnetic resonance (NMR) and electronic circular dichroism (ECD) data. Isocaulamidines have an altered pattern of N-methyl substitution (N-15 vs N-13 in the caulamidines) with a concomitant double-bond rearrangement to provide a new C-14/N-13 imine functionality. Caulamidine C (2) and isocaulamidine C (3) are the first members of this alkaloid family with two chlorine substituents in the core 6H-2,6-naphthyridine ring system.


Asunto(s)
Alcaloides , Antineoplásicos , Urocordados , Animales , Urocordados/química , Alcaloides/farmacología , Alcaloides/química , Espectroscopía de Resonancia Magnética , Imagen por Resonancia Magnética , Estructura Molecular
8.
Pest Manag Sci ; 79(1): 55-67, 2023 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-36067067

RESUMEN

BACKGROUND: Acyrthosiphon pisum Harris is the most destructive pest worldwide because of its ability to feed on plants directly and transmit plant viruses as a vector. This study aims to identify triterpenoid saponins from Oxytropis hirta Bunge as biopesticides to control aphids. RESULTS: Three new azukisapogenol triterpenoid saponins (1-3), a new pinoresinol lignan glycoside (8), and four known saponins (4-7) were identified from the root of O. hirta. Compounds 4-7 displayed significant aphicidal activities against A. pisum with oral toxicities (LC50  = 51.10-147.43 µg/mL, 72 h), deterrent effects (deterrence index = 1.00, 100-200 µg/mL, 24 h), and aphid reproduction inhibitory effects (inhibition rates = 75.91-86.73%, 400 µg/mL, 24 h), respectively. The carboxyl groups at C-3 GlcA and C-30 were functional groups for their aphicidal activities. The toxic symptoms caused by the optimal 5 involved insect body-color changes from light green to dark or gray-green, and then brown until death. The intestinal cavity, apical microvilli, nuclei, mitochondria, and electron dense granules in the midgut tissues of A. pisum were the target sites showing aphicidal activity. The suppression of pepsin and α-amylase, and the activation of lipase and trypsin could be the signs of organelle damage in the midgut tissues. CONCLUSION: Azukisapogenol triterpenoid saponins from O. hirta could be used as biopesticides to control aphids for their multiple efficacies, including oral toxicity, deterrent activity, and reproduction inhibitory activity. The toxic symptoms involved insect body-color changes. Midgut tissues and their related enzymes were the targets for saponins showing aphicidal activities. © 2022 Society of Chemical Industry.


Asunto(s)
Áfidos , Oxytropis , Saponinas , Animales , Áfidos/efectos de los fármacos , Oxytropis/química , Triterpenos/química , Saponinas/química , Saponinas/farmacología , Insecticidas/química , Insecticidas/farmacología
9.
ACS Appl Mater Interfaces ; 14(45): 50499-50506, 2022 Nov 16.
Artículo en Inglés | MEDLINE | ID: mdl-36397312

RESUMEN

Type 2 diabetes mellitus (T2DM) is a chronic metabolic disease characterized by low-grade inflammation and insulin resistance. In this process, innate immune cells play a crucial role in recognizing the stimuli (free fatty acid, lipopolysaccharide, and cytokines) and mediating the inflammatory response, contributing to the development of T2DM. Neutralizing inflammatory cytokines and blocking the inflammation cascade provide great potential for the treatment of T2DM. Here, we applied a macrophage membrane as a bait, which could specifically recognize and bind the stimuli, to encapsulate nanoparticles and capture the stimuli, further preventing inflammation. The in vivo experiment results suggest that the nanoparticles could reduce the production of proinflammatory cytokines, decrease insulin resistance, and realize significant therapeutic effects for T2DM. A potential strategy is thus offered for blocking immune response, holding a wide application in metabolic and autoimmune diseases.


Asunto(s)
Diabetes Mellitus Tipo 2 , Resistencia a la Insulina , Nanopartículas , Humanos , Diabetes Mellitus Tipo 2/tratamiento farmacológico , Diabetes Mellitus Tipo 2/prevención & control , Resistencia a la Insulina/fisiología , Macrófagos/metabolismo , Inflamación/metabolismo , Citocinas/metabolismo , Nanopartículas/uso terapéutico
10.
J Nat Prod ; 85(5): 1419-1427, 2022 05 27.
Artículo en Inglés | MEDLINE | ID: mdl-35465663

RESUMEN

Chemical investigation of the marine hydroid Dentitheca habereri led to the identification of eight new diacylated zoanthoxanthin alkaloids, named dentithecamides A-H (1-8), along with three previously reported analogues, zoamides B-D (9-11). The structures of compounds 1-11 were elucidated by spectroscopic and spectrometric analyses, including IR, HRESIMS, and NMR experiments, and by comparison with literature data. Compounds 1-11 are the first zoanthoxanthin alkaloids to be reported from a hydroid. Dentithecamides A (1) and B (2) along with zoamides B-D (9-11), which all share a conformationally mobile cycloheptadiene core, inhibited PAX3-FOXO1 regulated transcriptional activity and thus provided a structural framework for the potential development of more potent PAX3-FOXO1 inhibitors.


Asunto(s)
Alcaloides , Imidazoles , Alcaloides/química
11.
ACS Appl Bio Mater ; 5(4): 1692-1699, 2022 04 18.
Artículo en Inglés | MEDLINE | ID: mdl-35297253

RESUMEN

Iron oxide nanoparticles can induce cell death due to the ferroptosis mechanism, showing a great potential for cancer therapy. Here, we synthesized different-sized iron oxide nanoparticles (2-100 nm) to investigate their antitumor effect and toxicity mechanism. It was found that ultrasmall nanoparticles (< ∼5 nm) could accumulate in nucleus and were more efficient in triggering the generation of •OH than larger nanoparticles due to the quicker release of Fe2+, thus exhibiting more remarkable cytotoxicity. Nevertheless, 10 nm iron oxide nanoparticles group displayed the best antitumor effect in vivo. We studied the in vivo and intratumoral biodistribution of the nanoparticles and found that the therapeutic effects were related to both the tumoral accumulation and intratumoral distribution of nanoparticles. This work indicates the appropriate size of Fe3O4 NPs for cancer treatment and illustrates the possible factors that influence the therapeutic effect, suggesting the great potential of iron oxide in clinical application.


Asunto(s)
Ferroptosis , Nanopartículas , Neoplasias , Muerte Celular , Humanos , Nanopartículas/uso terapéutico , Neoplasias/tratamiento farmacológico , Distribución Tisular
12.
Plant Dis ; 106(9): 2462-2469, 2022 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-35196100

RESUMEN

Valsa mali, the causal agent of apple Valsa canker, produces several phytotoxic metabolites to promote infection. Bioassay and 1H nuclear magnetic resonance (NMR)-guided isolation from the culture filtrate of V. mali strain 03-8 led to the identification of seven compounds including three unreported ones, ethyl phloretate (1), ethyl p-coumarate (2), and 1-p-hydroxybenzoyl glycerol (3). Compounds 1 and 2 produced significant phytotoxicity, with average lesion areas of 6.22 and 3.74 mm2, along with 2.96 and 3.47 mm2 at 1 mg/ml on mature and tissue-cultured apple leaves, respectively, whereas compound 3 did not cause any symptoms on host plants. The necrotic lesion area of compounds 1 and 2 on tobacco leaves was 52.65 and 48.28 mm2, respectively, compared with the negative control (0.46 mm2) at 1 mg/ml. At the same concentration, compounds 1 and 2 showed no significant influence on the germination rate of lettuce seeds while significantly decreasing the root length of lettuce seedlings to 6.74 and 4.67 mm, respectively, compared with that treated with sterile distilled water (22.01 mm). The discovery indicated that compounds 1 and 2 could be considered as non-host-specific toxins. Furthermore, compounds 1 and 2 could cause cell shrinkage, organelle damage, plasmolysis, and eventually ruptured protoplasmic membranes with cell death for their phytotoxicity in the host plants under optical microscopy and transmission electron microscopy. The results shed light on the mechanism for toxins 1 and 2 in V. mali-infected plants at the macroscopic and cellular levels.


Asunto(s)
Ascomicetos , Malus , Ascomicetos/metabolismo , Germinación , Enfermedades de las Plantas
13.
Pest Manag Sci ; 77(11): 5268-5277, 2021 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34310837

RESUMEN

BACKGROUND: Tobacco mosaic virus (TMV) is a disreputable plant pathogen that causes a decline in the quality and yield of various economic crops. Natural products are important potential sources of biopesticides to control TMV. This study focuses on the discovery of anti-TMV active flavonoid glycosides and their mode of action on TMV particles from Clematis lasiandra Maxim. RESULTS: A new benzoyl acylated flavonoid glycoside, kaempferol 3-O-(2''-benzoyl)-ß-d-glucopyranosyl-7-O-α-l-rhamnopyranoside (1), and nine known flavonoids (2-10) were identified first from C. lasiandra. The hydroxyl group at C-7, E-p-coumarate at C-6'' in the Glc of C-6, and the glucuronic acid at C-3 were functional groups for the antiviral flavonoid glycosides. Flavonoids 2, 5, and 6 showed higher inactivation efficacies of 64.62% to 82.54% compared with ningnanmycin at 500 µg ml-1 . The protective and curative efficacies for 2 and 5 were 57.44-59.00% and 41.17-43.92% at 500 µg ml-1 , respectively. Compound 5 showed higher TMV systemic resistance with control efficacies of 41.64%, 36.56% and 27.62% at concentrations of 500, 250 and 125 µg ml-1 compared with ningnanmycin in K326 tobaccos, respectively. Compound 5 can directly fracture TMV particles into small fragments combining with the fusion phenomena, and TMV-CP was an important target for 5 to break TMV particles. CONCLUSION: Flavonoid glycosides from C. lasiandra showed potent antiviral activities against TMV with multiple modes of action including inactivation, protective and curative effects, and inducing systemic resistance. TMV-CP was an important target for active flavonoid glycosides to fracture TMV particles. The results provided evidence that flavonoid glycosides from C. lasiandra have the potential to control TMV.


Asunto(s)
Clematis , Virus del Mosaico del Tabaco , Antivirales/farmacología , Flavonoides/farmacología , Glicósidos/farmacología , Virión
14.
Pest Manag Sci ; 77(1): 455-463, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-32776383

RESUMEN

BACKGROUND: The diamondback moth, Plutella xylostella (L.) (Lepidoptera: Plutellidae), is a global insect pest of crops, leading to a reduction of agricultural products in productivity and quality. Plant saponins are rich sources for the discovery of candidates to control insect pests. This study focused on discovery of triterpenoid saponins from Clematis aethusifolia Turcz and evaluation of their antifeedant, insecticidal and insect growth inhibitory activities against the 3rd instar larvae of P. xylostella. RESULTS: Seven triterpenoid saponins (1-7) were isolated for the first time from the n-BuOH extract of C. aethusifolia. Monodesmosides 1, 2, and 5 with a free 28-COOH group showed much higher antifeedant activity (DC50 were 733.67-844.77 µg mL-1 at 24 h, and 737.19-748.28 µg mL-1 at 48 h) than bidesmosides 3-4 and 6-7 (DC50 were 1284.35-2053.98 µg mL-1 at 24 h, and 1183.72-1990.96 µg mL-1 at 48 h). Similarly, monodesmosides 1, 2, and 5 (LC50 were 1462.78-1785.96 µg mL-1 ) showed stronger insecticidal activity than bidesmosides 3-4 and 6-7 (LC50 were 2219.22-3050.51 µg mL-1 ) against P. xylostella at 72 h. These results suggest the 28-COOH group is an important functional group for their antifeedant and insecticidal activity. Besides, monodesmosides 1, 2, and 5 showed insect growth inhibitory activity against P. xylostella through reduction of larval growth and percentage of pupation, associated with prolongation of larval and pupal stages. CONCLUSION: The present results provide evidence that triterpenoid saponins from C. aethusifolia, particularly those monodesmosidic saponins with a free 28-COOH group, have the potential to be developed as pesticides to control P. xylostella.


Asunto(s)
Clematis , Insecticidas , Mariposas Nocturnas , Saponinas , Triterpenos , Animales , Insectos , Insecticidas/farmacología , Larva , Saponinas/farmacología
15.
Pestic Biochem Physiol ; 171: 104697, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-33357538

RESUMEN

Glycoprotein (GP)-1 is a glycoprotein elicitor with antiviral activity found in Streptomyces kanasensis zx01. GP-1 can induce programmed cell death (PCD) in vitro; however, the underlying mechanism is unclear. In the present study, we demonstrated that GP-1 induced PCD in tobacco suspension cells, which was modulated by hydrogen peroxide (H2O2). GP-1 participated in and modulated biologically relevant signaling in plant cells. GP-1 induced tobacco cell death in a dose- and time-dependent manner; affected the expression of BRI1-associated receptor kinase 1 (BAK1) and the accumulation of salicylic acid (SA), which are related to PCD; and enzymatic activities and mitochondrial functions. In conclusion, GP-1-induced PCD in tobacco may be mediated by H2O2 which alters BAK1 and SA levels, as well as mitochondrial and gene function. This cell signal cascade played an important role in the process of GP-1 induced plant disease resistance.


Asunto(s)
Peróxido de Hidrógeno , Nicotiana , Apoptosis , Glicoproteínas , Streptomyces
16.
ACS Omega ; 5(31): 19661-19666, 2020 Aug 11.
Artículo en Inglés | MEDLINE | ID: mdl-32803061

RESUMEN

Four new 8-O-4' neolignans, characterized at methoxy or ethoxy groups substituted at C-7, namely, (±) lasiandranins A-D (1-4), and two known analogs (±) pinnatifidanin BV (5) and (±) pinnatifidanin BVI (6) were isolated from the whole plants of Clematis lasiandra Maxim. The structures of 1-6 were determined by spectroscopic methods including 1D, 2D NMR, ECD, and HRESIMS analysis. Compounds 1 and 5 were determined as erythro configuration, while 2-4 and 6 were determined as threo configuration based on the chemical shift difference of H-9a and H-9b in CD3OD. The 8-O-4' neolignans were found from the genus Clematis for the first time. Compounds 1-6 were evaluated for their antibacterial activity against three plant pathogenic bacteria Pseudomonas syringae pv. actinidiae, Ralstonia solanacearum, and Erwinia carotovora by agar and broth dilution methods. Compounds 1-6 showed potent antibacterial activity against R. solanacearum with MIC values of 25-50 µg/mL and relatively lower activity against P. syringae pv. actinidiae with MIC values of 50-100 µg/mL, while they were inactive to E. carotovora.

17.
Pest Manag Sci ; 76(7): 2360-2367, 2020 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-32020760

RESUMEN

BACKGROUND: Botanical pesticide plays an essential role in the control of agricultural pests. Corydalis curviflora Maxim. is used as a cholagogue and larvicide in the rural areas of Northwest China. In this study, our objective was to identify the insect active ingredients of C. curviflora extract. RESULTS: Bioassay-guided isolation of the high active fraction led to the identification of two novel N-demethyl hexahydrobenzophenanthridine-type alkaloids, Curviflorain A (1) and Curviflorain B (2), together with nine known alkaloids, ambiguanine A (3), ambiguanine B (4), ambiguanine C (5), 6-acetylambinine (6), 1,1-dimethyl-6-methoxy-7-hydroxyl-1,2,3,4-tetrahydroisoquinoline (7), hendersine B (8), coryximine (9), isochotensine (10) and corysolidine (11). Compounds 1, 2, and 6 showed promising activity to the larvae of Culex pipiens pallens Coq. and Aedes albopictus Skuse. These compounds were also tested against the insect pests, Mythimna separata walker. and Schizaphis graminum Rondani. CONCLUSION: These findings provide a better understanding of the insecticidal activity of C. curviflora extract and the active compounds. This has the potential to lead to a more effective botanical insecticide.


Asunto(s)
Corydalis , Aedes , Alcaloides , Animales , China , Culex , Insecticidas , Larva
18.
Neural Regen Res ; 15(2): 293-301, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-31552902

RESUMEN

The histone deacetylase inhibitor, trichostatin A, is used to treat Alzheimer's disease and can improve learning and memory but its underlying mechanism of action is unknown. To determine whether the therapeutic effect of trichostatin A on Alzheimer's disease is associated with the nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like epichlorohydrin-related protein-1 (Keap1) signaling pathway, amyloid ß-peptide 25-35 (Aß25-35) was used to induce Alzheimer's disease-like pathological changes in SH-SY5Y neuroblastoma cells. Cells were then treated with trichostatin A. The effects of trichostatin A on the expression of Keap1 and Nrf2 were detected by real-time quantitative polymerase chain reaction, western blot assays and immunofluorescence. Total antioxidant capacity and autophagy activity were evaluated by total antioxidant capacity assay kit and light chain 3-I/II levels, respectively. We found that trichostatin A increased cell viability and Nrf2 expression, and decreased Keap1 expression in SH-SY5Y cells. Furthermore, trichostatin A increased the expression of Nrf2-related target genes, such as superoxide dismutase, NAD(P)H quinone dehydrogenase 1 and glutathione S-transferase, thereby increasing the total antioxidant capacity of SH-SY5Y cells and inhibiting amyloid ß-peptide-induced autophagy. Knockdown of Keap1 in SH-SY5Y cells further increased trichostatin A-induced Nrf2 expression. These results indicate that the therapeutic effect of trichostatin A on Alzheimer's disease is associated with the Keap1-Nrf2 pathway. The mechanism for this action may be that trichostatin A increases cell viability and the antioxidant capacity of SH-SY5Y cells by alleviating Keap1-mediated inhibition Nrf2 signaling, thereby alleviating amyloid ß-peptide-induced cell damage.

19.
PLoS One ; 14(7): e0218513, 2019.
Artículo en Inglés | MEDLINE | ID: mdl-31265452

RESUMEN

Mung bean (Vigna radiata), an important legume crop, has the property of desiccation tolerance (DT), which is lost in the final stage of germination (preimbibition, 18 h-24 h). We compared parameters related to the programmed cell death (PCD) of mung bean seeds before and after dehydration at different imbibition stages through various detection methods. The results of Evans blue and TTC staining methods showed that the dehydration process could lead to cell death. The results of optical and subcellular morphology showed that PCD occurred after dehydration. The destruction of DNA integrity and the activity changes in caspase and total nuclease in mung bean seeds after dehydration treatment indicated that the loss of desiccation tolerance was related to PCD. Dehydration resulted in the destruction of the mitochondrial structure, reversal of the membrane potential, and the entrance of cytochrome C into the cytoplasm. These processes all indicate that the mitochondrial apoptosis pathway was the main form of dehydration-induced PCD. The results of cytoplasmic Ca2+ concentration showed that Ca2+ signaling also played a role in inducing PCD, with the upstream signal being dehydration-induced changes in water potential and the downstream signal being the ROS and mitochondrial PT channel, according to the order in which these signals happened. The mitochondrial apoptosis pathway can be considered the main mechanism of dehydration-induced PCD based on our analysis of the sequence of major events in PCD. The main processes include dehydration induction, changes in Ca2+ and mitochondrial respiratory electron transport, the reversal of mitochondrial membrane potential induced by ROS and Ca2+, and the transmission and execution of PCD downstream signals induced by cytochrome C release.


Asunto(s)
Apoptosis , Señalización del Calcio , Resistencia a la Enfermedad , Potencial de la Membrana Mitocondrial , Mitocondrias/metabolismo , Semillas/metabolismo , Vigna/metabolismo , ADN de Plantas/metabolismo , Deshidratación , Desecación , Mitocondrias/genética , Consumo de Oxígeno , Especies Reactivas de Oxígeno/metabolismo , Semillas/genética , Vigna/genética
20.
Org Lett ; 21(12): 4750-4753, 2019 06 21.
Artículo en Inglés | MEDLINE | ID: mdl-31150264

RESUMEN

Spirodactylone (1), a hexacyclic indolizidone alkaloid possessing a novel spiro ring system, was isolated from the marine sponge Dactylia sp. The structure was elucidated by extensive spectroscopic methods including application of the LR-HSQMBC NMR pulse sequence. Oxidative cyclization of denigrin B (2), an aryl-substituted 2-oxo-pyrroline derivative that was also isolated from the sponge extract, provided material identical to spirodactylone (1). This confirmed the assigned structure and provides insight into the probable biogenesis of 1.


Asunto(s)
Alcaloides/química , Indolizinas/química , Compuestos Policíclicos/química , Poríferos/química , Pirroles/química , Alcaloides/metabolismo , Animales , Ciclización , Indolizinas/síntesis química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Oxidación-Reducción , Compuestos Policíclicos/síntesis química , Poríferos/metabolismo , Pirroles/metabolismo
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