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1.
Bioorg Chem ; 148: 107480, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38772291

RESUMEN

A novel series of erythrina derivatives as PARP-1/FTase inhibitors were synthesized, and evaluated for their biological activities. Compound T9 had excellent inhibitory effects on cell viability (A549: IC50 = 1.74 µM; A549/5-Fu: IC50 = 1.03 µM) and in vitro enzyme activities (PARP-1: IC50 = 0.40 µM; FTase: IC50 = 0.067 µM). Molecular docking and point mutation assays demonstrated the interaction of compound T9 with key amino acid residues. The compound T9 exhibited potent anti-proliferation and anti-migration capabilities against A549 and A549/5-Fu cells. PCR array and western blot results showed that compound T9 could effectively inhibit EMT-related proteins in A549 and A549/5-Fu cells, thereby inhibiting the development of lung cancer. Importantly, compound T9 could significantly inhibit tumor growth in the A549 xenograft tumor model (TGI = 65.3 %). In conclusion, this study was the first presentation of the concept of dual-target inhibitors of the PARP-1/FTase enzymes. It also provides the basis for further research and development of novel PARP-1/FTase inhibitors.


Asunto(s)
Antineoplásicos , Proliferación Celular , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Transición Epitelial-Mesenquimal , Erythrina , Neoplasias Pulmonares , Poli(ADP-Ribosa) Polimerasa-1 , Humanos , Poli(ADP-Ribosa) Polimerasa-1/antagonistas & inhibidores , Poli(ADP-Ribosa) Polimerasa-1/metabolismo , Neoplasias Pulmonares/tratamiento farmacológico , Neoplasias Pulmonares/patología , Proliferación Celular/efectos de los fármacos , Transición Epitelial-Mesenquimal/efectos de los fármacos , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Relación Estructura-Actividad , Erythrina/química , Animales , Estructura Molecular , Ratones , Simulación del Acoplamiento Molecular , Inhibidores de Poli(ADP-Ribosa) Polimerasas/farmacología , Inhibidores de Poli(ADP-Ribosa) Polimerasas/química , Inhibidores de Poli(ADP-Ribosa) Polimerasas/síntesis química , Ratones Desnudos , Neoplasias Experimentales/tratamiento farmacológico , Neoplasias Experimentales/patología , Neoplasias Experimentales/metabolismo , Supervivencia Celular/efectos de los fármacos , Ratones Endogámicos BALB C , Movimiento Celular/efectos de los fármacos
2.
Microb Pathog ; 190: 106635, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38579934

RESUMEN

The plant Erythrina indica comes under Fabaceae family, mainly used for used in traditional medicine as nervine sedative, antiepileptic, antiasthmatic, collyrium in opthalmia, antiseptic. Current study focused synthesize of silver nanoparticles (AgNPs) by E. indica leaf ethanol extract. The green-synthesized AgNPs underwent characterization using multiple analytical techniques, including UV-visible, FTIR, DLS, SEM, TEM, XRD, and EDX, and estimation of their antioxidant activity and antimicrobial activity. Phytochemical analysis identified alkaloids, tannins, saponins, flavonoids, and phenols as secondary metabolites. The Total Phenol Content (TPC) was determined to be 237.35 ± 2.02 mg GAE-1, indicating a substantial presence of phenolic compounds. The presence of AgNPs was verified through UV-Visible analysis at 420 nm, and FT-IR revealed characteristic phenolic functional groups. DLS analysis indicated a narrow size distribution (polydispersity index - PDI: 3.47%), with SEM revealing spherical AgNPs of approximately 20 nm. TEM showed homogeneous, highly polycrystalline AgNPs with lattice spacing at 0.297. XRD analysis demonstrated crystallinity and purity, with distinct reflection peaks corresponding to miller indices of JCPDS card no. 01 087 1473. In vitro, AgNPs exhibited robust antioxidant activity like; DPPH, ABTS, and H2O2, surpassing E. indica-assisted synthesis. ABTS assay indicated higher antioxidant activity (81.94 ± 0.05%) for AgNPs at 734 nm, while E. indica extraction showed 39.67 ± 0.07%. At 532 nm, both E. indica extraction (57.71 ± 0.11%) and AgNPs (37.41 ± 0.17%) exhibited H2O2 scavenging. Furthermore, AgNPs displayed significant antimicrobial properties, inhibiting Staphylococcus aureus (15.7 ± 0.12 mm) and Candida albicans (10.7 ± 0.17 mm) byfor the concentration of 80 µg/mL. Through the characterizations underscore of the potential of Erythrina indica-synthesized AgNPs, rich in polyphenolic compounds, for pharmacological, medical, biological applications and antipyretic properties.


Asunto(s)
Antiinfecciosos , Antioxidantes , Erythrina , Nanopartículas del Metal , Pruebas de Sensibilidad Microbiana , Fitoquímicos , Extractos Vegetales , Hojas de la Planta , Plata , Plata/química , Plata/farmacología , Antioxidantes/farmacología , Antioxidantes/química , Nanopartículas del Metal/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Erythrina/química , Antiinfecciosos/farmacología , Antiinfecciosos/química , Hojas de la Planta/química , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Espectroscopía Infrarroja por Transformada de Fourier , Fenoles/química , Fenoles/farmacología , Difracción de Rayos X , Flavonoides/química , Flavonoides/farmacología , Flavonoides/análisis , Tecnología Química Verde , Candida albicans/efectos de los fármacos , Taninos/farmacología , Taninos/química
3.
J Asian Nat Prod Res ; 26(3): 394-398, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-37342004

RESUMEN

A new C22 polyacetylene, erysectol A (1), and seven isoprenylated pterocarpans, phaseollin (2), phaseollidin (3), cristacarpin (4), (3'R)-erythribyssin D/(3'S)-erythribyssin D (5a/5b) and dolichina A/dolichina B (6a/6b) were isolated from the twigs and leaves of Erythrina subumbrans. Their structures were determined based on their NMR spectral data. Except for 2-4, all the other compounds were isolated from this plant for the first time. Erysectol A was the first reported C22 polyacetylene from plants. Polyacetylene was isolated from Erythrina plants for the first time.


Asunto(s)
Erythrina , Pterocarpanos , Pterocarpanos/química , Erythrina/química
4.
Biomed Chromatogr ; 38(3): e5810, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38146195

RESUMEN

Erythrina bidwillii Lindl., Leguminosae, constitutes a valuable crop for horticulture and medicine; however, it is rarely investigated. Menopause is a crucial transitional period in women's health. Women worldwide consider the use of phytoestrogens as a safe hormone replacement therapy to alleviate detrimental menopausal symptoms. Thus, the discovery of novel phytoestrogens is highly demanded. The present study aimed to investigate, for the first time, the metabolomic profile and the estrogenic potential of E. bidwillii Lindl. leaf. Ultra-performance liquid chromatography-electrospray ionization-tandem mass spectrometry and gas chromatography-mass spectrometry metabolite profiling revealed the prevalence of alkaloids, flavonoids, isoflavonoids and fatty acids. Additionally, five erythrinan alkaloids, cristanine A (1), 8-oxoerythraline (2), (+)-erythrinine (3), (+)-erythraline (4) and 8-oxoerythrinine (5), along with the isoflavonoid genistin (6), were isolated. Erythrina bidwillii leaf extract exhibited significant in vivo estrogenic, anti-osteoporotic, anti-hyperlipidemic, hepatoprotective, and nephroprotective activities, utilizing ovariectomized rat model. Moreover, ethyl acetate and hexane fractions possessed significant in vitro estrogeic potential on MCF-7 cell lines. An in silico study of the isolated metabolites revealed that (+)-erythrinine (3) and 8-oxoerythrinine (5) exhibited the highest affinity for ERα and ERß, respectively, modeling them as potential estrogenic lead metabolites. Therefore, E. bidwillii leaf could be employed as promising hormone replacement therapy for postmenopausal women after thorough clinical trials.


Asunto(s)
Alcaloides , Erythrina , Femenino , Humanos , Ratas , Animales , Fitoestrógenos/química , Erythrina/química , Alcaloides/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Células MCF-7
5.
Chem Biodivers ; 20(7): e202300200, 2023 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-37329524

RESUMEN

Alzheimer's disease (AD) is a major health problem. Cholinergic transmission is greatly affected in AD. Phytochemical investigation of the alkaloid rich fraction (AF) of Erythrina corallodendron L leaves resulted in isolation of five known alkaloids: erysodine, erythrinine, 8-oxoerythrinine, erysovine N-oxide and erythrinine N-oxide. In this study, eysovine N-oxide was reported for the second time in nature. AF was assayed for cholinesterase inhibition at the concentration of 100 µg mL-1 . AF showed a higher percent inhibition for butyrylcholinesterase enzyme (BuChE) (83.28 %) compared to acetylcholinesterase enzyme (AChE) (64.64 %). The isolated alkaloids were also assayed for their anti-BuChE effect. In-silico docking study was done for the isolated compounds at the binding sites of AChE and BuChE to determine their binding pattern and interactions, also molecular dynamics were estimated for the compound displaying the best fit for AChE and BuChE. In addition, ADME parameters and toxicity were predicted for the isolated alkaloids compared to donepezil.


Asunto(s)
Alcaloides , Enfermedad de Alzheimer , Erythrina , Humanos , Butirilcolinesterasa/metabolismo , Acetilcolinesterasa/metabolismo , Erythrina/química , Enfermedad de Alzheimer/tratamiento farmacológico , Inhibidores de la Colinesterasa/farmacología , Inhibidores de la Colinesterasa/química , Alcaloides/química , Óxidos , Simulación del Acoplamiento Molecular
6.
J Nat Prod ; 86(4): 759-766, 2023 04 28.
Artículo en Inglés | MEDLINE | ID: mdl-36938984

RESUMEN

The roots of Erythrina lysistemon, growing in Egypt, yielded 24 flavonoid compounds, including 17 pterocarpans, two isoflavanones, one flavanone, two isoflavans, one 2-arylbenzofuran, and an isoflava-3-ene. Nine pterocarpans have not been reported previously (7-9, 11-14, 19, and 20), and 11 are reported here for the first time from this species. Structures were established using HRESIMS, NMR, and circular dichroism techniques. Selected compounds were tested for their ability to block the growth of human retinal endothelial cells and antiangiogenic activity in vitro. The isoflavonoids 5 and 6, and the pterocarpans 1, 2, 4, 20, and 22 demonstrated selective antiproliferative activities on endothelial cells compared to a nonendothelial cell type, with concentration-dependent antiangiogenic effects in vitro against HRECs, a cell type relevant to neovascular eye diseases.


Asunto(s)
Erythrina , Pterocarpanos , Humanos , Flavonoides/farmacología , Erythrina/química , Pterocarpanos/farmacología , Pterocarpanos/química , Células Endoteliales/metabolismo , Extractos Vegetales/farmacología
7.
J Sep Sci ; 46(12): e2200800, 2023 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-36715692

RESUMEN

Plants in the genus Erythrina is a potential source of chemical constituents, one of which is flavonoids, which have diverse bioactivities. To date, literature on the flavonoids from the genus Erythrina has only highlighted the phytochemical aspects, so this review article will discuss isolation techniques and strategies for the first time. More than 420 flavonoids have been reported in the Erythrina genus, which are grouped into 17 categories. These flavonoid compounds were obtained through isolation techniques and strategies using polar, semi-polar, and non-polar solvents. Various chromatographic techniques have been developed to isolate flavonoids using column flash chromatography, quick column chromatography, centrifugally accelerated thin-layer chromatography, radial chromatography, medium-pressure column chromatography, semi-preparative high-performance liquid chromatography, and preparative high-performance liquid chromatography. Chromatographic processes for isolating flavonoids can be optimized using multivariate statistical applications such as response surface methodology with central composite design, Box-Behnken design, Doehlert design, and mixture design.


Asunto(s)
Erythrina , Flavonoides , Flavonoides/análisis , Erythrina/química , Cromatografía Líquida de Alta Presión , Extractos Vegetales/química , Cromatografía en Capa Delgada
8.
Fitoterapia ; 166: 105408, 2023 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-36586624

RESUMEN

Thirteen undescribed dimeric Erythrina alkaloids, named as erythrivarines A1-A13, were isolated from the barks of Erythrina variegata L. and. Their structures were determined on the basis of NMR, UV and mass spectral analyses. Dimeric Erythrina alkaloid with a C-8/8' linkage in erythrivarine A1 was not yet reported. Representative dimers from titled plant were used to prove their occurrence as natural products by LC - MS detection. Additionally, simultaneous investigation enabled us to propose the natural property of seemingly artificial Erythrina alkaloid with acetonyl group.


Asunto(s)
Alcaloides , Erythrina , Indolizinas , Erythrina/química , Estructura Molecular , Alcaloides/química , Extractos Vegetales/química , Espectrometría de Masas
9.
Phytochemistry ; 206: 113550, 2023 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-36481312

RESUMEN

A chemical investigation of the twigs and leaves of Erythrina subumbrans led to the isolation and structural elucidation of three coumaronochromones, erythrinasubumbrin A and (±)-erythrinasubumbrin B, five prenylated flavanones, (±)-erythrinasubumbrin C and erythrinasubumbrins D-F, and two prenylated isoflavones, (±)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone, in addition to 18 known analogues. Two extra cinnamylphenols previously only known as commercial synthetic products were also isolated and elucidated from a natural source for the first time, and assigned the trivial names erythrinasubumbrins G and H. Their structures were characterized by detailed analysis of spectroscopic data, including HRESIMS and 2D NMR. The absolute configurations of the previously undescribed isolates and the known coumaronochromone lupinol C were determined by specific rotation and electronic circular dichroism (ECD) data. All the isolates were evaluated for their inhibitory activities on protein tyrosine phosphatase 1 B (PTP1B) and nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells as well as their cytotoxicity against the HCT116 cell line. The pair of enantiomers, (+)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone and (-)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone, and the known compounds lupinol C, 4'-O-methyl-8-prenylnaringenin, glepidotin B, shuterin, parvisoflavones A, luteone, lupiwighteone, 2,3-dehydrokievitone, 6,8-diprenylgenistein, angustone A, and 2'-O-demethylbidwillol B exhibited different levels of PTP1B inhibitory activities with IC50 values ranging from 3.21 to 19.17 µM, while erythrinasubumbrin A, (-)-erythrinasubumbrin B, (+)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone, (-)-5,4'-dihydroxy-[4,5-cis-4-ethoxy-5-hydroxy-6,6-dimethyl-4,5-dihydropyrano (2,3:7,6)]-isoflavone, and the known compounds lupinol C, 8-prenylnaringenin, macatrichocarpin A, alpinumisoflavone, and 2'-O-demethylbidwillol B substantially inhibited NO production in BV-2 microglial cells. In addition, 8-prenylnaringenin showed weak cytotoxicity with an IC50 value of 9.13 µM. This is the first report of PTP1B inhibitory activity for a coumaronochromone.


Asunto(s)
Erythrina , Flavanonas , Isoflavonas , Óxido Nítrico , Erythrina/química , Estructura Molecular , Monoéster Fosfórico Hidrolasas , Isoflavonas/farmacología , Flavanonas/química
10.
Nutrients ; 14(24)2022 Dec 09.
Artículo en Inglés | MEDLINE | ID: mdl-36558415

RESUMEN

The estimated and concerning rise in world population over the next few years and the consequent increase in food demand will lead to a deterioration in global food security. To avoid or reduce this world crisis, informed and empowered consumers are turning to sustainable and nutrient-rich foods that substitute animal products, also reducing their associated environmental impact. Moreover, due to the demonstrated influence of diet on the risk of high incidence and mortality of noncommunicable diseases, the current established food pattern is focused on the consumption of foods that have functionality for health. Among these new foods, traditional and underutilized plants are gaining interest as alternative protein sources providing nutritional and biological properties. In this work, the potential of Erythrina edulis (chachafruto) proteins as a source of multifunctional peptides after transit through the gastrointestinal tract has been demonstrated, with antioxidant and immunostimulating effects in both biochemical assays and cell culture. While low molecular weight peptides released during the digestive process were found to be responsible for protection against oxidative stress mediated by their radical scavenging activity, high molecular weight peptides exerted immunostimulating effects by upregulation of immunoresponse-associated biomarkers. The findings of this study support the promising role of chachafruto proteins as a new antioxidant and immunostimulatory ingredient for functional foods and nutraceuticals.


Asunto(s)
Erythrina , Animales , Erythrina/química , Erythrina/metabolismo , Antioxidantes/metabolismo , Péptidos/química , Proteínas , Digestión
11.
Yakugaku Zasshi ; 142(9): 977-991, 2022.
Artículo en Japonés | MEDLINE | ID: mdl-36047225

RESUMEN

Studies on the isolation and molecular mechanisms of phytochemicals with anti-tumor or anti-inflammatory properties are important to developing new drugs for cancer and neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease. In the course of a study to screen bioactive isoflavones from Erythrina poeppigiana (Leguminosae), we isolated an isoflavone with potent apoptosis-inducing activity against human leukemia HL-60 cells. It was designated erypoegin K. The studies demonstrated an enantiomer, (S)-erypoegin K, displayed selective cytotoxic activity, was a novel inhibitor of topoisomerase II, and possessed anti-tumor activity both in vitro and in vivo. We identified other apoptosis-inducing isoflavones with the ability to inhibit glyoxalase I. Dimeric acridone alkaloids, carbazole alkaloids, and coumarin and quinoline derivatives-all obtained mainly from plants in the family Rutaceae-induced apoptosis of HL-60 cells via the production of reactive oxygen species and mitochondrial dysfunction. We also identified terpenoid coumarins, carbazole quinones, rotenoid derivatives, and quinolone alkaloids with anti-inflammatory activities. These compounds reduced nitric oxide (NO) production from RAW264.7 macrophage cells stimulated with lipopolysaccharides and interferon-γ. Some of the compounds displayed neuroprotective activity by reducing NO production. This review primarily describes our recent studies on erypoegin K, and other compounds with apoptosis-inducing and anti-inflammatory activities.


Asunto(s)
Alcaloides , Erythrina , Isoflavonas , Carbazoles , Erythrina/química , Humanos , Isoflavonas/química , Isoflavonas/farmacología , Fitoquímicos/farmacología
12.
Molecules ; 27(18)2022 Sep 15.
Artículo en Inglés | MEDLINE | ID: mdl-36144753

RESUMEN

Flavonoids are a secondary metabolite group with various bioactivities, such as antioxidants. They are rich in the genus Erythrina, such as Erythrina crista-galli. This research aims to isolate and characterize flavonoids from the twigs of E. crista-galli and determine their antioxidant properties through in silico and in vitro assays. The ethyl acetate extract of E. crista-galli twigs were separated by column chromatography and characterized using spectroscopic methods. Density functional theory (DFT) calculations were performed on the isolated flavonoids and the reference compounds (ascorbic acid and quercetin) to obtain global descriptive parameters and a donor-acceptor map (DAM). We successfully isolated lupinifolin (1) and citflavanone (2) for the first time from E. crista-galli, along with lonchocarpol A (3), which has been discovered previously. The DAM suggests that these flavanones are good antiradicals with effective electron donors. However, they tend to be electron acceptors in methanol. The frontier molecular orbital analysis implies that lupinifolin (1) is a better antiradical than the other flavanones. The DPPH assays show that lupinifolin (1) has the highest antioxidant (antiradical) activity, with an IC50 value of 128.64 ppm. The in silico studies showed similar trends to the in vitro assays using the DPPH method.


Asunto(s)
Erythrina , Flavanonas , Antioxidantes/metabolismo , Antioxidantes/farmacología , Ácido Ascórbico/metabolismo , Erythrina/química , Flavanonas/metabolismo , Flavanonas/farmacología , Flavonoides/química , Metanol/metabolismo , Extractos Vegetales/química , Quercetina/metabolismo
13.
Molecules ; 27(8)2022 Apr 16.
Artículo en Inglés | MEDLINE | ID: mdl-35458781

RESUMEN

Although Erythrina senegalensis is a plant widely used in traditional medicine in sub-Saharan Africa, its biological properties have been poorly investigated to date. We first characterized by conventional reactions the composition of several stem bark extracts and evaluated in acellular and cellular assays their pro- or antioxidant properties supported by their high phenolic and flavonoid content, particularly with the methanolic extract. The pro- or antioxidant effects observed did not correlate with their IC50 concentrations against five cancer cell lines determined by MTT assay. Indeed, the CH2Cl2 extract and its ethyl acetate (EtOAc) subfraction appeared more potent although they harbored lower pro- or antioxidant effects. Nevertheless, at equipotent concentration, both extracts induced ER- and mitochondria-derived vacuoles observed by fluorescent microscopy that further led to non-apoptotic cell death. LC coupled to high resolution MS investigations have been performed to identify chemical compounds of the extracts. These investigations highlighted the presence of compounds formerly isolated from E. senegalensis including senegalensein that could be retrieved only in the EtOAc subfraction but also thirteen other compounds, such as 16:3-Glc-stigmasterol and hexadecanoic acid, whose anticancer properties have been previously reported. Nineteen other compounds remain to be identified. In conclusion, E. senegalensis appeared rich in compounds with antioxidant and anticancer properties, supporting its use in traditional practice and its status as a species of interest for further investigations in anticancer drug research.


Asunto(s)
Antioxidantes , Erythrina , Antioxidantes/química , Antioxidantes/farmacología , Erythrina/química , Flavonoides/farmacología , Fenoles , Extractos Vegetales/química , Extractos Vegetales/farmacología
14.
Phytochemistry ; 198: 113160, 2022 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-35292327

RESUMEN

Ten dimeric and two monomeric Erythrina alkaloids, all of them are undescribed, were isolated from the bark of Erythrina variegata L. and named as erythrivarines O-Z. Their structures were determined on the basis of NMR and UV-spectroscopy and mass spectrometry. Dimeric Erythrina alkaloids with a C-10/11' linkage in erythrivarine O and a C-7/10' connectivity in erythrivarines P-U are not yet reported. The two identified monomeric alkaloids may be the precursors of the described dimeric derivatives. These co-occurring dimeric and monomeric alkaloids enabled us to propose a possible biosynthetic pathway leading to these dimers. Their effects of preventing hearing loss were additionally evaluated and erythrivarine T showed as a potential protector of the House Ear Institute-Organ of Corti 1 (HEI-OC-1) cells against neomycin.


Asunto(s)
Alcaloides , Erythrina , Alcaloides/química , Alcaloides/farmacología , Erythrina/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masas
15.
J Asian Nat Prod Res ; 24(5): 457-467, 2022 May.
Artículo en Inglés | MEDLINE | ID: mdl-35023423

RESUMEN

Five new Erythrina alkaloids and five known E. alkaloids were isolated from a 95% ethanol extract of the stems of Erythrina corallodendron L. Their chemical structures were elucidated by UV, IR, HRESIMS, NMR and X-ray. Furthermore, the analgesic activities of E. alkaloids 1, 2 and 6 were evaluated by using an acetic acid-induced writhing test in mice, and their writhing inhibition rates were 67.9%, 64.6% and 70.3% at doses of 20 mg/kg, respectively.


Asunto(s)
Alcaloides , Erythrina , Alcaloides/química , Alcaloides/farmacología , Animales , Erythrina/química , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Extractos Vegetales/química
16.
Nat Prod Res ; 36(19): 4886-4891, 2022 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-33813975

RESUMEN

(±) Erysectin A (1), a new isoprenylated isoflavone with a rare acetonyl group, along with 15 known compounds including eight isoprenylated isoflavones (2-9), two isoprenylated flavanones (10-11), three flavanones (12-14), a flavone (15), and a chalcone (16), was isolated from the twigs and leaves of Erythrina secundiflora Hassk. Their structures were identified based on their 1 D and 2 D NMR spectral data. All the compounds were isolated from this plant for the first time. Compound 1 showed moderate cytotoxicity on several cancer cell lines.[Formula: see text].


Asunto(s)
Chalconas , Erythrina , Flavanonas , Flavonas , Isoflavonas , Erythrina/química , Flavanonas/química , Flavonas/química , Isoflavonas/química , Isoflavonas/farmacología , Estructura Molecular
17.
Biomed Pharmacother ; 144: 112198, 2021 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-34656058

RESUMEN

Erythrina poeppigiana belongs to Fabaceae family (subfamily Papillionoideae) and is commonly found in tropical and subtropical regions in Brazil. Herein, we described the purification and characterization of a new Kunitz-type inhibitor, obtained from E. poeppigiana seeds (EpTI). EpTI is composed by three isoforms of identical amino-terminal sequences with a molecular weight ranging from 17 to 20 kDa. The physicochemical features showed by EpTI are common to Kunitz inhibitors, including the dissociation constant (13.1 nM), stability against thermal (37-100 °C) and pH (2-10) ranging, and the presence of disulfide bonds stabilizing its reactive site. Furthermore, we investigated the antimicrobial, anti-adhesion, and anti-biofilm properties of EpTI against Gram-positive and negative bacteria. The inhibitor showed antimicrobial activity with a minimum inhibitory concentration (MIC, 5-10 µM) and minimum bactericidal concentration (MBC) of 10 µM for Enterobacter aerogenes, Enterobacter cloacae, Klebsiella pneumoniae, Staphylococcus aureus, and Staphylococcus haemolyticus. The combination of EpTI with ciprofloxacin showed a marked synergistic effect, reducing the antibiotic concentration by 150%. The increase in crystal violet uptake for S. aureus and K. pneumoniae strains was approximately 30% and 50%, respectively, suggesting that the bacteria plasma membrane is targeted by EpTI. Treatment with EpTI at 1x and 10 x MIC significantly reduced the biofilm formation and prompted the disruption of a mature biofilm. At MIC/2, EpTI decreased the bacterial adhesion to polystyrene surface within 2 h. Finally, EpTI showed low toxicity in animal model Galleria mellonella. Given its antimicrobial and anti-biofilm properties, the EpTI sequence might be used to design novel drug prototypes.


Asunto(s)
Antibacterianos/farmacología , Bacterias/efectos de los fármacos , Biopelículas/efectos de los fármacos , Erythrina , Extractos Vegetales/farmacología , Inhibidores de Tripsina/farmacología , Animales , Antibacterianos/aislamiento & purificación , Antibacterianos/toxicidad , Bacterias/crecimiento & desarrollo , Biopelículas/crecimiento & desarrollo , Ciprofloxacina/farmacología , Sinergismo Farmacológico , Erythrina/química , Pruebas de Sensibilidad Microbiana , Mariposas Nocturnas/efectos de los fármacos , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Semillas , Inhibidores de Tripsina/aislamiento & purificación , Inhibidores de Tripsina/toxicidad
18.
J Pharm Pharmacol ; 73(1): 93-97, 2021 Mar 01.
Artículo en Inglés | MEDLINE | ID: mdl-33791806

RESUMEN

OBJECTIVES: The erythrinan alkaloids erythravine and 11α-hydroxy-erythravine from Erythrina verna (Vell.) have been extensively investigated for their anxiolytic and anticonvulsant effects. Both are structurally similar to the erythrartine that also exhibit anxiolytic effects, but there is no report on its anticonvulsant potential. Since some anxiolytic drugs can be useful in the management of epileptic seizures, we investigated whether erythrartine could prevent seizures induced by different chemoconvulsants. METHODS: Experiments were performed using different concentrations of erythrartine injected via intracerebroventricular in rats submitted to pilocarpine, kainic acid, pentylenetetrazol or picrotoxin-induced seizures. Moreover, the rotarod test was performed to verify the effects of erythrartine on animal motor coordination. RESULTS: Our data showed for the first time that erythrartine prevented the occurrence of seizures induced by all of the chemoconvulsants tested and did not affect locomotor performance neither produced sedative effect on animals. CONCLUSION: Obtained results validate the ethnopharmacological significance of E. verna and provide new information on erythrartine, another erythrinian alkaloid of biotechnological and medicinal interest.


Asunto(s)
Alcaloides/uso terapéutico , Anticonvulsivantes/uso terapéutico , Erythrina/química , Fitoterapia , Extractos Vegetales/uso terapéutico , Convulsiones/prevención & control , Alcaloides/farmacología , Animales , Ansiolíticos/farmacología , Ansiolíticos/uso terapéutico , Anticonvulsivantes/farmacología , Convulsivantes , Modelos Animales de Enfermedad , Epilepsia/tratamiento farmacológico , Masculino , Extractos Vegetales/farmacología , Ratas Wistar , Convulsiones/inducido químicamente
19.
Bioorg Med Chem ; 30: 115904, 2021 01 15.
Artículo en Inglés | MEDLINE | ID: mdl-33341500

RESUMEN

Erypoegin K, an isoflavone isolated from the stem bark of Erythrina poeppigiana, has a single chiral carbon in its structure and exists naturally as a racemic mixture. Our previous study showed (S)-erypoegin K selectively exhibits potent anti-proliferative and apoptosis-inducing activity against human leukemia HL-60 cells. To identify the target molecule of (S)-erypoegin K, we employed the human cancer cell panel analysis (termed JFCR39) coupled with a drug sensitivity database of pharmacologically well-characterized drugs for comparison using the COMPARE algorithm. (S)-erypoegin K exhibited a similar profile to that of etoposide, suggesting the molecular target for erypoegin K may be topoisomerase II (Topo II). Subsequent experiments using purified human Topo IIα established that the (S)-isomer selectively stabilizes the cleavage complex composed of double-stranded plasmid DNA and the enzyme. Moreover, (S)-erypoegin K inhibited decatenation of kinetoplast DNA. Molecular docking studies clearly indicated specific binding of the (S)-isomer to the active site of Topo IIα involving hydrogen bonds that help stabilize the cleavage complex. (S)-erypoegin K displayed potent cytotoxic activity against two human gastric cancer cells GCIY and MKN-1 with IC50 values of 0.270 and 0.327 µM, respectively, and induced enzyme activities of caspase 3 and 9. Cell cycle analysis showed marked cell cycle arrest at G2 phase in both cell lines. (S)-erypoegin K also displayed significant antitumor activity toward GCIY xenografted mice. The present study suggests (S)-erypoegin K acts as a Topo II inhibitor to block the G2/M transition of cancer cells.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , ADN-Topoisomerasas de Tipo II/metabolismo , Erythrina/química , Neoplasias Gástricas/tratamiento farmacológico , Inhibidores de Topoisomerasa II/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Puntos de Control de la Fase G2 del Ciclo Celular/efectos de los fármacos , Humanos , Simulación del Acoplamiento Molecular , Estructura Molecular , Neoplasias Gástricas/metabolismo , Neoplasias Gástricas/patología , Relación Estructura-Actividad , Inhibidores de Topoisomerasa II/química , Inhibidores de Topoisomerasa II/aislamiento & purificación , Células Tumorales Cultivadas
20.
Artículo en Inglés | MEDLINE | ID: mdl-32516097

RESUMEN

BACKGROUND: Genus Erythrina belongs to family Fabaceae, which is widely distributed in tropical and subtropical areas. It has been used in both traditional herbal medicines and pharmacological applications. Original research articles and publications on the overview of alkaloids related to this genus are available, but a supportive systematic review account which highlighted phytochemical aspects of other types of secondary metabolites is currently insufficient. OBJECTIVE: With the utilization of data and information from SCI-Finder, Google Scholar, the Web of Science, Scopus, Science Direct, PubMed, Chemical Abstracts, ACS journals, Springer, Taylor Francis, Bentham Science and IOP Science, the reliable material sources of this systematic review paper were obtained from the literature published from the 1980s to now. CONCLUSION: A vast amount of data showed that the non-alkaloidal secondary metabolites were obtained from genus Erythrina with various classes of chemical structures. Herein, approximately five hundred constituents were isolated, comprising flavonoids, terpenoids, saponins, phytosterols, phenols, arylbenzofurans, coumarins, alcohols, ceramides, mono-sugars and fatty acid derivatives. In agreement with the previous phytochemical reports on the plants of the family Fabaceae, flavonoids reached a high amount in the plants of genus Erythrina. Numerous biological activity investigations such as anti-bacteria, anti-cancer, anti-virus using isolated compounds from Erythrina species suggested that secondary metabolites of Erythrina plants are now becoming the promising agents for drug developments.


Asunto(s)
Erythrina/química , Flavonoides/química , Fitoquímicos/química , Extractos Vegetales/química , Plantas Medicinales/química , Ácidos Grasos/química , Flavonoides/farmacología , Humanos , Estructura Molecular , Fitoquímicos/farmacología , Fitosteroles/química , Fitoterapia , Extractos Vegetales/farmacología , Saponinas/química , Metabolismo Secundario , Terpenos/química
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