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1.
China Journal of Chinese Materia Medica ; (24): 4253-4260, 2023.
Article in Chinese | WPRIM | ID: wpr-1008622

ABSTRACT

This study aims to establish a method for the simultaneous determination of 7 active components in Dracocephalum tanguticum and to evaluate the quality of medicinal materials from different habitats. The method was established with high performance liquid chromatography(HPLC) and the gradient elution was performed with the mobile phase of acetonitrile-methanol-0.2% phosphoric acid solution at a column temperature of 35 ℃, an injection volume of 15 μL, and a flow rate of 0.6 mL·min~(-1). The detection wavelength was set as 215 nm. With rosmarinic acid as the internal reference, the relative correction factors and the content of other 6 components were calculated. The results were compared with those obtained with the external standard method. The results showed that the samples from Huangzhong county, Qinghai province had the best quality, with the highest content of p-hydroxybenzoic acid, cosmosiin, rosmarinic acid, oleanolic acid, and ursolic acid(9.29, 12.14, 6.02, 3.11, 17.67 mg·g~(-1) respectively). The samples from Chaya county, Tibet autonomous region ranked the second, with the highest content of betulin and betulinic acid(15.53, 7.17 mg·g~(-1), respectively). The method is accurate, reliable, and repeatable and suitable for the simultaneous determination of multiple components in D. tanguticum. The content of functional components varied in the samples from different producing areas and can be used as the indicator for the quality evaluation of medicinal materials.


Subject(s)
Cinnamates , Drugs, Chinese Herbal/analysis , Lamiaceae , Chromatography, High Pressure Liquid/methods , Rosmarinic Acid
2.
China Journal of Chinese Materia Medica ; (24): 4130-4136, 2023.
Article in Chinese | WPRIM | ID: wpr-1008609

ABSTRACT

Twelve compounds were isolated from Liquidambaris Resina by silica gel column chromatography and thin layer chromatography. Their structures were identified on the basis of spectral data, electron capture detector data, and physicochemical properties as(2'R, 3'R)-2',3'-dihydroxy-hydrocinnamyl-(E)-cinnamate(1),(E)-cinnamyl-(E)-cinnamate(2), cinnamic acid(3), 28-norlup-20(29)-en-3-one-17β-hydroperoxide(4), erythrodiol(5), 13β,28-epoxy-30-hydroxyolean-1-en-3-one(6),(3β)-olean-12-ene-3,23-diol(7), 2α,3α-dihydroxy-olean-12-en-28-oic acid(8), 28-hydroxyolean-12-en-3-one(9), 3-epi-oleanolic acid(10), 3-oxo-oleanolic acid(11), and hederagenin(12). Compound 1 was a new cinnamic acid ester derivative and compounds 2-4,6-8, and 12 were isolated from Liquidambaris Resina for the first time. Compounds 4, 5, 10, and 12 exerted inhibitory effects on the proliferation of human umbilical vein endothelial cells(HUVEC) with the IC_(50) values of(17.43±2.17),(35.32±0.61),(27.50±0.80), and(46.30±0.30) μmol·L~(-1), respectively.


Subject(s)
Humans , Oleanolic Acid , Endothelial Cells , Esters , Cinnamates , Triterpenes/chemistry , Molecular Structure
3.
Int. j. morphol ; 40(1): 157-167, feb. 2022. ilus, tab
Article in English | LILACS | ID: biblio-1385584

ABSTRACT

SUMMARY: Carbon tetrachloride (CCl4) is a manufactured chemical and does not occur naturally in the environment. CCl4 is a clear liquid that evaporates very easily. It has a sweet odor. CCl4 is toxic to the mammalian liver and is hepatocarcinogenic in both rats and mice. Rosemary (Rosmarinus Officinalis) is commonly used as a spice and flavoring agent in food processing. It is known for its antioxidant properties. The present study aims to investigate the antioxidant activity of rosmarinic acid (RA) on CCl4-induced liver toxicity in adult male albino rats. Forty adult male albino rats were divided into 4 groups with 10 rats in each group. Group I (control group). Group II animals received RA at a dose of 50 mg/kg/day by oral gavage for 4 weeks. Group III animals received CCl4 intraperitoneally at a dose of 3ml/kg twice weekly for 4 weeks. Group IV animals received CCl4 Plus RA. At the end of the experiment, liver specimens are processed for histological, immunohistochemical, EM and biochemical studies. Administration of RA deceased the elevated serum liver enzymes (AST, ALT, and ALP), elevated MDA level and immunoexpression of the proapoptotic protein (Bax) induced by CCl4. It increased reduced glutathione (GSH), glutathione peroxidase (GSH-Px), superoxide dismutase (SOD), and immunoexpression of the antiapoptotic protein (Bcl2). It also improved the histological and ultrastructural changes induced by CCl4. It appears that Rosmarinic acid has protective effects against CCl4-induced hepatotoxicity as indicated by biochemical, histological, immunohistochemical and ultrastructural results.


RESUMEN: El tetracloruro de carbono (CCl4) es un producto químico fabricado y no se encuentra de forma natural en el medio ambiente. CCl4 es un líquido transparente que se evapora fácilmente; tiene un olor dulce. CCl4 es tóxico para el hígado de los mamíferos y es hepatocarcinogénico tanto en ratas como en ratones. El romero (Rosmarinus officinalis) se usa comúnmente como condimento y agente aromatizante en el procesamiento de alimentos. Es conocido por sus propiedades antioxidantes. El presente estudio tuvo como objetivo investigar la actividad antioxidante del ácido rosmarínico (RA) sobre la toxicidad hepática inducida por CCl4 en ratas albinas macho adultas. Se dividieron cuarenta ratas albinas macho adultas en 4 grupos con 10 ratas en cada grupo. Grupo I (grupo control). Los animales del grupo II recibieron AR a una dosis de 50 mg / kg / día por sonda oral durante 4 semanas. Los animales del grupo III recibieron CCl4 por vía intraperitoneal a una dosis de 3 ml / kg dos veces por semana durante 4 semanas. Los animales del grupo IV recibieron CCl4 Plus RA. Al final del experimento, las muestras de hígado se procesaron para estudios histológicos, inmunohistoquímicos, EM y bioquímicos. La administración de AR eliminó las enzimas hepáticas séricas elevadas (AST, ALT y ALP), el nivel elevado de MDA y la inmunoexpresión de la proteína proapoptótica (Bax) inducida por CCl4. Aumentó el glutatión reducido (GSH), glutatión peroxidasa (GSH-Px), la superóxido dismutasa (SOD) y la inmunoexpresión de la proteína antiapoptótica (Bcl2). También mejoró los cambios histológicos y ultraestructurales inducidos por CCl4. El ácido rosmarínico puede tener efectos protectores contra la hepatotoxicidad inducida por CCl4, tal como lo indican los resultados bioquímicos, histológicos, inmunohistoquímicos y ultraestructurales.


Subject(s)
Animals , Male , Mice , Carbon Tetrachloride/toxicity , Cinnamates/administration & dosage , Depsides/administration & dosage , Chemical and Drug Induced Liver Injury/drug therapy , Antioxidants/administration & dosage , Superoxide Dismutase/analysis , Immunohistochemistry , Cinnamates/pharmacology , Oxidative Stress/drug effects , Microscopy, Electron, Transmission , Depsides/pharmacology , Glutathione Peroxidase/analysis , Malondialdehyde/analysis , Antioxidants/pharmacology
4.
China Journal of Chinese Materia Medica ; (24): 944-950, 2021.
Article in Chinese | WPRIM | ID: wpr-878960

ABSTRACT

Two new sucrose cinnamates(1 and 2) along with nine known compounds(3-11) were isolated from ethanol extract of Polygonum lapathifolium var. salicifolium by silica gel column chromatography, ODS column chromatography and semi-preparative HPLC. Their structures were elucidated by extensive spectroscopic methods including 1 D-and 2 D-NMR experiments, as well as HR-ESI-MS analysis. Eleven compounds(7 sucrose cinnamates, 3 phenylpropanoids and 1 lactone) were obtained and their structures were identified as(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside(1),(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-(6-O-acetyl)-α-D-glucopyranoside(2),(3-O-feruloyl)-β-D-fructofuranosyl-(2→1)-(6-O-p-coumaroyl)-α-D-glucopyranoside(3), hydropiperoside(4), vanicoside C(5),(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-(6-O-feruloyl)-α-D-glucopyranoside(6), vanicoside B(7),trans-p-hydroxycinnamic acid methyl ester(8), trans-p-hydroxycinnamic acid ethyl ester(9), methyl ferulate(10) and dimethoxydimethylphthalide(11), respectively. Compounds 1 and 2 were two new sucrose cinnamates, and compounds 1-11 were isolated from this plant for the first time. The antioxidant activities of the isolated compounds 1-9 were investigated by an oxygen radical absorbance capacity(ORAC) assay, and all nine compounds were found to show strong antioxidant activities. Among them, compound 6(10 μmol·L~(-1)) was the supreme one in antioxidant activities, with its ORAC value equivalent to(1.60±0.05) times of 50 μmol·L~(-1) Trolox.


Subject(s)
Antioxidants , Cinnamates , Esters , Molecular Structure , Polygonum , Sucrose
5.
China Journal of Chinese Materia Medica ; (24): 86-93, 2021.
Article in Chinese | WPRIM | ID: wpr-878915

ABSTRACT

Caffeic acid and its oligomers are the main water-soluble active constituents of the traditional Chinese medicine(TCM) Arnebiae Radix. These compounds possess multiple biological activities such as antimicrobial, antioxidant, cardiovascular protective, liver protective, anti-liver fibrosis, antiviral and anticancer activities. The phenylpropanoid pathway in plants is responsible for the biosynthesis of caffeic acid and its oligomers. Glycosylation can change phenylpropanoid solubility, stability and toxic potential, as well as influencing compartmentalization and biological activity. In view of the important role played by de-glycosylation in the regulation of phenylpropanoid homeostasis, the biosynthesis of caffeic acid and its oligomers are supposed to be under the control of relative UDP-glycosyltransferases(UGTs). Through the data mining of Arnebia euchroma transcriptome, we cloned 15 full-length putative UGT genes. After recombinant expression using the prokaryotic system, the crude enzyme solution of the putative UGTs was examined for the glycosylation activities towards caffeic acid and rosmarinic acid in vitro. AeUGT_01, AeUGT_02, AeUGT_03, AeUGT_04 and AeUGT_10 were able to glycosylate caffeic acid and/or rosmarinic acid resulting in different mono-and/or di-glycosylated products in the UPLC-MS analyses. The characterized UGTs were distantly related to each other and divided into different clades of the phylogenetic tree. Based on the observation that each characterized UGT exhibited substrate or catalytic similarity with the members in their own clade, we supposed the glycosylation abilities towards caffeic acid and/or rosmarinic acid were evolved independently in different clades. The identification of caffeic acid and rosmarinic acid UGTs from A. euchroma could lead to deeper understanding of the caffeic acid oligomers biosynthesis and its regulation. Furthermore, these UGTs might be used for regiospecific glycosylation of caffeic acid and rosmarinic acid to produce bioactive compounds for potential therapeutic applications.


Subject(s)
Boraginaceae/genetics , Caffeic Acids , Chromatography, Liquid , Cinnamates , Cloning, Molecular , Depsides , Glycosyltransferases/genetics , Phylogeny , Tandem Mass Spectrometry
6.
Rev. bras. parasitol. vet ; 30(3): e009221, 2021. tab, graf
Article in English | LILACS, VETINDEX | ID: biblio-1341182

ABSTRACT

Abstract This study aimed to chemically characterize the essential oils (EOs) of Cinnamomum zeylanicum (cinnamon) and Eremanthus erythropappus (candeia) and evaluate their acaricidal activity, together with that of their major compounds and cinnamyl acetate derivative, against Rhipicephalus microplus. Essential oil compounds were identified through gas chromatography. The larval packet test (LPT) at concentrations ranging from 0.31 to 10.0 mg/mL and the adult immersion test (AIT) at concentrations between 2.5 and 60.0 mg/mL were performed. (E)-cinnamaldehyde and α-bisabolol were the major compounds in cinnamon (86.93%) and candeia (78.41%) EOs, respectively. In the LPT, the EOs of cinnamon and candeia and the compounds (E)-cinnamaldehyde, α-bisabolol and cinnamyl acetate resulted in 100% mortality at concentrations of 2.5, 2.5, 5.0, 10.0 and 10.0 mg/mL respectively. In the AIT, percentage control values > 95% were observed for cinnamon and candeia EOs, (E)-cinnamaldehyde and α-bisabolol at the concentrations of 5.0, 60.0, 20.0, and 20.0 mg/mL, respectively, whereas cinnamyl acetate showed low activity. We conclude that EOs and their compounds showed high acaricidal activity, whereas the acetylated derivative of (E)-cinnamaldehyde presented less acaricidal activity on R. microplus engorged females.


Resumo Este estudo teve como objetivo caracterizar quimicamente os óleos essenciais (OE) de Cinnamomum zeylanicum (canela) e Eremanthus erythropappus (candeia) e avaliar sua atividade acaricida, juntamente com a de seus principais compostos e do derivado de acetato de cinamila, sobre Rhipicephalus microplus. Os compostos do óleo essencial foram identificados por cromatografia gasosa. Foram realizados o Teste de Pacote de Larvas (TPL), em concentrações variando de 0,31 a 10,0 mg/mL, e o Teste de Imersão de Adultos (TIA), em concentrações entre 2,5 e 60,0 mg/mL. (E)-cinnamaldeído e α-bisabolol foram os principais compostos nos OE da canela (86,93%) e da candeia (78,41%), respectivamente. No TPL, os OEs de canela e candeia, e os compostos (E)-cinnamaldeído, α-bisabolol e acetato de cinamila resultaram em 100% de mortalidade nas concentrações de 2,5, 2,5, 5,0, 10,0 e 10,0 mg/mL, respectivamente. No TIA, valores percentuais de controle >95% foram observados para OE de canela e candeia, (E)-cinnamaldeído e α-bisabolol nas concentrações de 5,0, 60,0, 20,0 e 20,0 mg/mL, respectivamente, enquanto o acetato de cinamila apresentou baixa atividade. Conclui-se que os OEs e seus compostos apresentaram alta atividade acaricida, enquanto o derivado acetilado do (E)-cinnamaldeído apresentou menor atividade acaricida em fêmeas ingurgitadas de R. microplus.


Subject(s)
Animals , Oils, Volatile/pharmacology , Rhipicephalus , Acaricides/pharmacology , Cinnamates , Cinnamomum zeylanicum , Larva
7.
Arq. bras. oftalmol ; 83(4): 305-311, July-Aug. 2020. graf
Article in English | LILACS | ID: biblio-1131600

ABSTRACT

ABSTRACT Purpose: Collagen deposition and myofibroblast differentiation are critical factors related to excessive scarring in ocular surgeries. This study evaluated the anti-fibrotic activity of rosmarinic acid on rabbit Tenon's capsule fibroblasts stimulated with transforming growth factor- β2. Methods: Primary cultures of rabbit Tenon's capsule fibroblasts were treated with various concentrations of rosmarinic acid for 12 h, in the presence and absence of transforming growth factor-β2. After 48 h, the proliferation index of rabbit Tenon's capsule fibroblasts and the differentiation of myofibroblasts were investigated through immunofluorescence staining for proliferating cell nuclear antigen and alpha smooth muscle actin. An automated cell counter and colorimetric metabolic activity assay were used to evaluate cell number and viability. Collagen expression and production were determined by quantitative real-time polymerase chain reaction and hydroxyproline assay, respectively. Results: Unstimulated rabbit Tenon's capsule fibroblasts treated with any concentration of rosmarinic acid exhibited diminished collagen expression (p<0.01) but showed no differences in proliferation index. Transforming growth factor-β2 exposure induced myofibroblast differentiation and increased collagen production. Exposure to rosmarinic acid at 1.0 and 3.0 µM concentrations reduced the proliferation index (p<0.02), as well as the collagen expression and hydroxyproline content (p<0.05). Exposure to 3.0 µM rosmarinic acid reduced viability (p=0.035) in unstimulated rabbit Tenon's capsule fibroblasts and cell numbers (p=0.001) in both stimulated and unstimulated rabbit Tenon's capsule fibroblast cultures. Conclusions: Exposure to 1.0 µM rosmarinic acid was noncytotoxic and led to reduced collagen expression and proliferation of stimulated rabbit Tenon's capsule fibroblasts. These findings suggest that rosmarinic acid is a relatively non-injurious anti-fibrotic compound to rabbit Tenon's capsule fibroblasts, with potential application as an adjunctive agent in ocular procedures, particularly in glaucoma surgeries.


RESUMO Objetivo: A deposição de colágeno e a diferenciação de miofibroblastos são fatores chaves relacionados à cicatrização excessiva em cirurgias oculares. Este estudo avaliou a atividade anti-fibrótica do ácido rosmarínico nos fibroblastos da cápsula de Tenon de coelhos estimulados com o fator de crescimento transformador-β2. Métodos: Culturas primárias de fibroblastos da cápsula de Tenon de coelhos foram tratadas com várias concentrações de ácido rosmarínico por 12h, na presença e na ausência do fator de crescimento transformador-β2. Após 48h, o índice de proliferação dos fibroblastos da cápsula de Tenon de coelhos e a diferenciação dos miofibroblastos foram investigados por coloração por imunofluorescência para proliferação de antígeno nuclear celular e α-actina de músculo liso, respectivamente. Um contador automático de células e um ensaio de atividade metabólica colorimétrica foram utilizados para avaliar o número e a viabilidade das células. A expressão e produção do colágeno foram determinadas por reação quantitativa em cadeia da polimerase em tempo real e ensaio de hidroxiprolina, respectivamente. Resultados: Fibroblastos da cápsula de Tenon de coelhos não estimulados tratados com qualquer concentração de ácido rosmarínico exibiram diminuição de colágeno (p<0,01), mas não mostraram diferenças no índice de proliferação. A exposição ao fator de crescimento transformador-β2 induziu a diferenciação de miofibroblastos e aumentou a produção de colágeno. A exposição ao ácido rosmarínico nas concentrações de 1,0 e 3,0 µM reduziu o índice de proliferação (p<0,02), bem como a expressão de colágeno e a quantificação de hidroxiprolina (p<0.05). A exposição a 3,0 µM de ácido rosmarínico reduziu a viabilidade (p=0,035) de fibroblastos da cápsula de Tenon de coelhos não estimulados e o número de células (p=0,001) em culturas de fibroblastos da cápsula de Tenon de coelhos estimuladas e não estimuladas. Conclusões: A exposição ao ácido rosmarínico 1,0 µM foi não citotóxica e levou à expressão reduzida de colágeno e menor proliferação de fibroblastos da cápsula de Tenon estimulados pelo fator de crescimento transformador-β2. Esses achados sugerem que o ácido rosmarínico é um composto antifibrótico relativamente não lesivo aos fibroblastos da cápsula de Tenon de coelhos, com potencial aplicação como agente adjuvante em procedimentos oculares, particularmente em cirurgias de glaucoma.


Subject(s)
Animals , Tenon Capsule , Rabbits , Cells, Cultured , Glaucoma , Cinnamates , Depsides , Fibroblasts
8.
Journal of Southern Medical University ; (12): 1628-1633, 2020.
Article in Chinese | WPRIM | ID: wpr-880798

ABSTRACT

OBJECTIVE@#To evaluate the effect of rosmarinic acid (RA) on mitophagy and hypertrophy of cardiomyocytes exposed to high glucose (HG).@*METHODS@#Rat cardiomyocytes (H9c2) exposed to HG (25 mmol/L) were treated with 50 μmol/L RA or with both RA treatment and Parkin siRNA transfection, with the cells cultured in normal glucose (5.5 mmol/L) and HG as the controls. The expressions of PINK1, Parkin and LC3II/LC3I in the cells were detected by Western blotting. The formation of mitochondrial autophagosomes was observed by transmission electron microscope. Flow cytometry was employed to detect the level of reactive oxygen species (ROS) and apoptotic rate of the cells. The activities of respiratory chain complex enzymes were measured by spectrophotometry. Fluorescence enzyme labeling and @*RESULTS@#RA treatment significantly increased the expression levels of PINK1, Parkin and LC3-II/I (@*CONCLUSIONS@#RA can protect rat cardiomyocytes against oxidative stress injury and cardiomyocyte hypertrophy induced by HG by activating Parkin-mediated mitophagy.


Subject(s)
Animals , Rats , Cinnamates , Depsides , Glucose , Hypertrophy , Mitophagy , Myocytes, Cardiac , Protein Kinases , Reactive Oxygen Species , Ubiquitin-Protein Ligases/genetics
9.
Acta cir. bras ; 35(3): e202000304, 2020. tab, graf
Article in English | LILACS | ID: biblio-1130623

ABSTRACT

Abstract Purpose To investigate the protective effect of rosmarinic acid (RA) in ovarian ischemia/reperfusion injury using biochemical, histopathological, and immunohistochemical methods. Methods Wistar female rats (n = 32) were randomly divided into four groups: control, ischemia, ischemia-reperfusion, and ischemia-reperfusion with RA. Rosmarinic acid was given at a dose of 50 mg/kg by oral gavage three hours after reperfusion. Malondialdehyde (MDA) levels and glutathione peroxidase (GSH-Px) activities were determined in the ovary tissue homogenates for each rat. Results In the ischemia-reperfusion with RA group, the epithelial cells are regularly regulated at the periphery, and the degenerative changes in preantral and antral follicle cells are reduced. Follicle cells and cells in the corpus luteum showed a decrease in vascular endothelial growth factor (VEGF) expression, while VEGF demonstrated a positive reaction in vascular endothelial cells and stromal cells. The TNF-α expression due to the decreased degenerative effect and inflammation was positive in the macrophage cells. The expression of caspase-3 as an apoptosis change was negative in antral follicle cells and granular cells around the antral follicle. Conclusion Different doses of RA may be useful in preventing ischemic damage after vascularization, inflammation, and apoptotic development after ischemia/reperfusion.


Subject(s)
Animals , Female , Rats , Ovarian Diseases , Reperfusion Injury , Cinnamates , Vascular Endothelial Growth Factor A , Depsides , Ovarian Diseases/drug therapy , Torsion Abnormality/drug therapy , Cinnamates/therapeutic use , Cinnamates/pharmacology , Rats, Wistar , Endothelial Cells , Depsides/therapeutic use , Depsides/pharmacology , Inflammation , Malondialdehyde , Antioxidants
10.
Acta cir. bras ; 35(4): e202000406, 2020. tab, graf
Article in English | LILACS | ID: biblio-1130636

ABSTRACT

Abstract Purpose To investigate the role of Rosmarinic acid (RA) in the prevention of traumatic brain injury and the immunohistochemical analysis of IBA-1 and GFAP expressions. Methods Healthy male rats were randomly divided into 3 groups consisting of 10 rats. Groups were as follows; control group, traumatic brain injury (TBI) group, and TBI+RA group. After traumatic brain injury, blood samples were taken from the animals and analyzed with various biochemical markers. And then IBA-1 and GFAP expressions were evaluated immunohistochemically. Results Significant results were obtained in all biochemical parameters between groups. Immunohistochemical sections showed IBA-1 not only in microglia and macrophage activity but also in degenerative neurons in blood vessel endothelial cells. However, GFAP reaction and post-traumatic rosmarinic acid administration showed positive expression in astrocytes with regular structure around the blood vessel. Conclusion Rosmarinic acid in blood vessel endothelial cells showed that preserving the integrity of astrocytic structure in the blood brain barrier may be an important antioxidant.


Subject(s)
Animals , Male , Calcium-Binding Proteins/analysis , Cinnamates/pharmacology , Craniotomy/methods , Depsides/pharmacology , Brain Injuries, Traumatic/prevention & control , Glial Fibrillary Acidic Protein/analysis , Microfilament Proteins/analysis , Reference Values , Immunohistochemistry , Random Allocation , Astrocytes/drug effects , Reproducibility of Results , Rats, Sprague-Dawley , Neuroprotective Agents/pharmacology , Brain Injuries, Traumatic/surgery , Brain Injuries, Traumatic/pathology , Glutathione Peroxidase/analysis , Malondialdehyde/analysis
11.
Acta cir. bras ; 34(11): e201901102, Nov. 2019. tab, graf
Article in English | LILACS | ID: biblio-1054682

ABSTRACT

Abstract Purpose: To investigate the effect of Picroside II on testicular ischemia and reperfusion (l/R) injury and the underlying mechanism. Methods: Sprague-Dawley rats were randomly divided into 4 groups: sham operated group (Sham), Sham with Picroside II treatment group (Sham+ Pic II), l/R group (l/R) and l/R with Picroside II treatment group (I/R+ Pic II). l/R model was established by rotating the left testis 720° in a clock-wise direction for 4 hours. The histopathologic and spermatogenetic evaluation was performed. The apoptosis changes and the levels of HO-1 (heme oxygenase-1), MPO (myeloperoxidase), NOX (NADPH oxidase), SOD (superoxide dismutase), XO (xanthine oxidase) and NOS (nitric oxide synthase) were measured. Results: The seminiferous tubules were damaged in l/R rats, but Picroside II alleviated the changes induced by l/R. The increased level of apoptosis was decreased by Picroside II (P=0.01, 9.05±0.35 vs. 4.85±0.25). The activities of HO-1, MPO, NOX, XO and MDA content were increased and the SOD activity was decreased in l/R (P<0.05) and could be reversed by Picroside II (P=0.03, 405.5±7.5 vs. 304±17U/mgprot; P=0.02, 0.99±0.05 vs. 0.52±0.04 mgprot; P=0.01, 260+7 vs. 189±2 mgprot; P=0.04, 10.95+0.55 vs. 8.75+0.35 U/mgprot; P=0.045, 6.8+0.7 vs. 3.75+0.35 mgprot; P=0.04, 44.5+3.5 vs. 57.5+3.5 mgprot). Western blot showed that the expression of iNOS, nNOS and eNOS were increased in l/R (P<0.05); however, they were decreased after Picroside II treatment (P<0.05). Conclusion: Picroside II attenuated testicular I/R injury in rats mainly through suppressing apoptosis and oxidative stress through reduction of nitric oxide synthesis.


Subject(s)
Animals , Male , Testis/blood supply , Reperfusion Injury/prevention & control , Cinnamates/pharmacology , Apoptosis/drug effects , Oxidative Stress/drug effects , Iridoid Glucosides/pharmacology , Nitric Oxide/biosynthesis , Reperfusion Injury/metabolism , Reperfusion Injury/pathology , Random Allocation , Blotting, Western , Rats, Sprague-Dawley , Peroxidase/analysis , In Situ Nick-End Labeling , Heme Oxygenase-1/analysis , Malondialdehyde/analysis , NADP/analysis
12.
Bol. latinoam. Caribe plantas med. aromát ; 18(1): 58-70, ene. 2019. tab, ilus
Article in English | LILACS | ID: biblio-1007470

ABSTRACT

The aim of this study was to evaluate the concentration and chemical composition of the essential oil the leaves of basil cultivars and hybrids cultivated in different cropping seasons: dry season and rainy season. The variables evaluated were the content and composition of essential oils in the two seasons. The essential oil content ranged from 0.66% to 3.21% in the dry season and from 0.80% to 4.20% in the rainy season. The major compounds found among the genotypes were linalool, methyl chavicol, neral, geranial, eugenol, and methyl (E)- cinnamate, defining the formation of five groups in each season, classified in the following chemotypes: methyl chavicol (Group 1), citral (neral+geranial) (Group 2), methyl cinnamate (Group 3), linalool (Group 4), and intermediate linalool (Group 5). All the traits evaluated had heritability (h ) greater than 95% and high CVg/CVe ratio values. The cropping season affected the content and chemical compositions of basil essential oil.


El objetivo de este estudio fue evaluar la concentración y composición química del aceite esencial las hojas de cultivares de albahaca e híbridos cultivados en diferentes temporadas de cultivo: estación seca y estación lluviosa. Las variables evaluadas fueron la contenido y la composición de los aceites esenciales en las dos estaciones. La contenido de aceite esencial varió de 0.66% a 3.21% en la estación seca y de 0.80% a 4.20% en la estación lluviosa. Los principales compuestos encontrados entre los genotipos fueron linalool, metilchavicol, neral, geranial, eugenol y metil (E)-cinamato, definiendo la formación de cinco grupos en cada estación, clasificados en los siguientes quimiotipos: metil chavicol (Grupo 1), citral (neral + geranial) (Grupo 2), cinamato de metilo (Grupo 3), linalool (Grupo 4) y linalol intermedio (Grupo 5). Todos los rasgos evaluados mostraron una heredabilidad (h ) mayor que el 95% y altos valores de relación CVg/CVe. La temporada de cultivo afectó la contenido y las composiciones químicas del aceite esencial de albahaca.


Subject(s)
Seasons , Oils, Volatile/chemistry , Plant Leaves/chemistry , Ocimum basilicum , Eugenol/analysis , Cinnamates/analysis , Monoterpenes/analysis , Anisoles/analysis
13.
China Journal of Chinese Materia Medica ; (24): 4704-4712, 2019.
Article in Chinese | WPRIM | ID: wpr-1008249

ABSTRACT

Rosmarinic acid,a hydrosoluble polyphenolic hydroxyl compound,is the active ingredient in such traditional Chinese medicines as Menthae Haplocalycis Herba,Salviae Miltiorrhizae Radix et Rhizoma,Rosemary,Perillae Folium. Because of its good anti-inflammatory,anti-oxidant and anti-tumor effects,it is widely used in food,medicine and other fields. However,the metabolic process and metabolites of rosmarinic acid in vivo have not been completely defined. In this study,an efficient method of ultra-high performance liquid chromatography combined with linear ion trap-Orbitrap(UHPLC-LTQ-Orbitrap) mass spectrometer was used to analyze the metabolites in vivo of rosmarinic acid in rats. Plasma,urine and feces samples were collected after oral administration of rosmarinic acid. After biological samples were processed by solid phase extraction,Acquity UPLC  BEH C18 column(2. 1 mm × 100 mm,1. 7 μm) was used with 0. 1% formic acid(A)-acetonitrile(B) solution as the mobile phase at the speed of 0. 30 m L·min-1 and temperature of 35 ℃ under gradient conditions. The plasma,urine,feces and the blank samples were then analyzed by ESI-LTQ-Orbitrap under both negative and positive ion modes. Based on the accurate mass measurement(<5),MS/MS fragmentation patterns,standards and literatures,a total of 36 metabolites were screened out and identified in the biological samples collected from rats after intragastric administration. Three were identified 3 from rat plasma,31 from urine,and 7 from feces. The main metabolic pathways of rosmarinic acid in rats can be divided into five parts. Rosmarinic acid were first decomposed into small molecules,such as trans-caffeic acid,coumaric acid,m-hydroxybenzoic acid and Danshensu,which were followed by sulfation,methylation,glucuronic acid conjugation and glucose conjugation. The results showed that UHPLC-LTQ-Orbitrap mass spectrometer could be used to analyze the metabolism of rosmarinic acid in rats,and provide reference for further studies on toxicology,pharmacodynamics and secondary development of Chinese medicine.


Subject(s)
Animals , Rats , Chromatography, High Pressure Liquid , Cinnamates/metabolism , Depsides/metabolism , Drugs, Chinese Herbal/metabolism , Tandem Mass Spectrometry , Rosmarinic Acid
14.
Rev. Soc. Bras. Med. Trop ; 51(6): 849-853, Nov.-Dec. 2018. tab, graf
Article in English | LILACS | ID: biblio-1041494

ABSTRACT

Abstract INTRODUCTION Leishmaniasis, Chagas disease, and malaria cause morbidity globally. The drugs currently used for treatment have limitations. Activity of cinnamic acid analogs against Leishmania spp., Trypanosoma cruzi, and Plasmodium falciparum was evaluated in the interest of identifying new antiprotozoal compounds. METHODS In vitro effects of analogs against L. braziliensis, L. infantum chagasi, T. cruzi, and P. falciparum, and hemolytic and cytotoxic activities on NCTC 929 were determined. RESULTS Three analogs showed leishmanicidal and tripanocidal activity. No antiplasmodial, hemolytic, or cytotoxic activity was observed. CONCLUSIONS Antiprotozoal activity of analogs against L. infantum braziliensis, L. infantum chagasi, and T. cruzi was demonstrated.


Subject(s)
Plasmodium falciparum/drug effects , Trypanosoma cruzi/drug effects , Cinnamates/pharmacology , Leishmania/drug effects , Antiprotozoal Agents/pharmacology , Cinnamates/chemistry , Parasitic Sensitivity Tests , Antiprotozoal Agents/chemistry
15.
China Journal of Chinese Materia Medica ; (24): 3962-3969, 2018.
Article in Chinese | WPRIM | ID: wpr-775391

ABSTRACT

To establish the high performance liquid chromatography (HPLC) fingerprint for Digeda-4 decoction (DGD-4D), determine the contents of aesculetin, geniposide, picroside Ⅰ, picroside Ⅱ and ellagicacid in DGD-4D, and provide the scientific foundation for quality control of DGD-4D. The analysis was performed on Diamonsil(2) C₁₈ (4.6 mm×250 mm,5 μm) column, with methanol-0.1% phosphoric acid aqueous solution as mobile phase for gradient elution. The flow rate was 1.0 mL·min⁻¹; injection size was 10 μL; temperature was maintained at 30 °C, and the detection wavelength was set at 254 nm. The common mode of DGD-4D HPLC fingerprint was established, and the hidden information was analyzed by Chemometrics. Chromatographic peaks for DGD-4D were identified by HPLC and quantitative analysis was conducted for characteristic peaks. There were 17 common peaks in the fingerprints and the similarity of the fingerprints was over 0.9 in all 15 batches. The samples were broadly divided into four kinds by principal component analysis and clustering analysis. Four marker compounds were verified by partial least squares discriminant analysis, and No. 9, 12 and 14 peaks were identified as geniposide, picroside Ⅱ, and picroside Ⅰ respectively. The average recoveries were in the range of 95.91%-97.31%. The HPLC fingerprint method for content determination is reliable, accurate, rapid, simple, and reproducible, and can be used as one of the effective methods to control the quality of DGD-4D.


Subject(s)
Chromatography, High Pressure Liquid , Cinnamates , Drugs, Chinese Herbal , Reference Standards , Iridoid Glucosides , Iridoids , Methanol , Principal Component Analysis , Quality Control
16.
Bol. latinoam. Caribe plantas med. aromát ; 16(4): 385-397, jul. 2017. ilus, tab
Article in English | LILACS | ID: biblio-882137

ABSTRACT

Myrcianthes is a Myrtaceous genus of flowering plants of about 30 to 40 species, distributed in the American continent. The aim of this work was to study the chemical composition of the foliar essential oil from M. fragrans growing wild in central Costa Rica. The essential oil was obtained through the steam distillation process in a Clevenger type apparatus. The chemical composition of the oil was performed by capillary gas chromatography with a flame detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS) using the retention indices on a DB-5 type capillary column in addition to mass spectral fragmentation patterns. A total of 98 compounds were identified, accounting for 98.8% of the total amount of the oil. The major constituents in the leaf oil were (E)-methyl cinnamate (39.6%), limonene (34.6%), α-pinene (6.8%), and linalool (6.8%). This is the first report of (E)-methyl cinnamate occurring in oils of this plant genus. These findings appear to suggest a new chemotype of M. fragrans.


Myrcianthes (Myrtaceae) consta de 30 a 40 especies, distribuidas en el continente americano. El objetivo del presente trabajo consistió en identificar la composición química del aceite esencial contenido en las hojas de M. fragrans, planta que crece en forma silvestre en el Valle Central de Costa Rica. La extracción del aceite se efectuó mediante el método de hidrodestilación usando un equipo de Clevenger modificado. La composición química del aceite se analizó mediante las técnicas de cromatografía gaseoso-líquida con detector de ionización de llama (GC-FID) y de cromatografía gaseoso-líquida acoplada a un detector de masas (GC-MS). Se utilizaron índices de retención obtenidos en una columna capilar tipo DB-5 y se compararon con los patrones de iones de fragmentación de masas. Se identificaron en total 98 compuestos, correspondientes a un 98.8% de los constituyentes totales. Los componentes mayoritarios del aceite resultaron ser (E)-cinamato de metilo (39.6%), limoneno (34.6%), α-pineno (6.8%) y linalol (6.8%). Este es el primer informe de la aparición de (E)-cinamato de metilo en aceite de hojas de este género de plantas. Los datos obtenidos parecen sugerir un nuevo quimiotipo de M. fragrans.


Subject(s)
Cinnamates/analysis , Myrtaceae/chemistry , Oils, Volatile/chemistry , Plant Leaves/chemistry , Terpenes/analysis , Chromatography, Gas/methods , Costa Rica , Cyclohexanes/analysis
17.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 917-927, 2017.
Article in English | WPRIM | ID: wpr-812040

ABSTRACT

Salvia miltiorrhiza is a medicinal plant widely used in the treatment of cardiovascular and cerebrovascular diseases. Hydrophilic phenolic acids, including rosmarinic acid (RA) and lithospermic acid B (LAB), are its primary medicinal ingredients. However, the biosynthetic pathway of RA and LAB in S. miltiorrhiza is still poorly understood. In the present study, we accomplished the isolation and characterization of a novel S. miltiorrhiza Hydroxyphenylpyruvate reductase (HPPR) gene, SmHPPR, which plays an important role in the biosynthesis of RA. SmHPPR contained a putative catalytic domain and a NAD(P)H-binding motif. The recombinant SmHPPR enzyme exhibited high HPPR activity, converting 4-hydroxyphenylpyruvic acid (pHPP) to 4-hydroxyphenyllactic acid (pHPL), and exhibited the highest affinity for substrate 4-hydroxyphenylpyruvate. SmHPPR expression could be induced by various treatments, including SA, GA, MeJA and Ag, and the changes in SmHPPR activity were correlated well with hydrophilic phenolic acid accumulation. SmHPPR was localized in cytoplasm, most likely close to the cytosolic NADPH-dependent hydroxypyruvate reductase active in photorespiration. In addition, the transgenic S. miltiorrhiza hairy roots overexpressing SmHPPR exhibited up to 10-fold increases in the products of hydrophilic phenolic acid pathway. In conclusion, our findings provide a new insight into the synthesis of active pharmaceutical compounds at molecular level.


Subject(s)
Amino Acid Sequence , Benzofurans , Biosynthetic Pathways , Genetics , Cinnamates , Depsides , Gene Expression Regulation, Plant , Genetics , Oxidoreductases , Genetics , Phenylpropionates , Metabolism , Phenylpyruvic Acids , Metabolism , Phylogeny , Plant Proteins , Genetics , Metabolism , Plant Roots , Chemistry , Genetics , Metabolism , Plants, Genetically Modified , Recombinant Proteins , Salvia miltiorrhiza , Chemistry , Genetics , Metabolism , Sequence Alignment
18.
Braz. j. med. biol. res ; 50(12): e6145, 2017. tab, graf
Article in English | LILACS | ID: biblio-888968

ABSTRACT

Chronic systemic inflammation and repetitive damage of vascular endothelia by incompatible dialysis system are probable causes of cardiovascular disease in patients on dialysis. The present study aimed to assess in vitro biocompatibility and anti-inflammatory effect of hemodialysis fluid supplemented with rosmarinic acid (RA) using human umbilical vein endothelial cells (HUVEC). HUVECs (5×106 cells/mL) were pre-exposed to 1 μg/mL of lipopolysaccharides (LPS) and incubated with RA-supplemented hemodialysis fluid (HDF). Cytotoxicity was assessed qualitatively by morphologic assessment and quantitatively by MTT assay. Expressions of proinflammatory mediators were assessed using quantitative real-time PCR and production of NO was quantified. Phosphorylation of AKT and nuclear localization of nuclear factor kappa B (NF-κB) were examined using western blotting. Exposure of HUVECs to RA-supplemented HDF had no influence on morphology and viability. Inhibition of proinflammatory mediator production in HUVECs by RA supplementation to HDF was significant in a dose-dependent manner. Exposure to RA-supplemented HDF resulted in a decrease in nitric oxide synthase expression and reduction of NO production in LPS-stimulated HUVECs. RA supplementation of HDF suppressed Akt activation in LPS-stimulated HUVECs. In addition, the level of cellular IκB was increased in parallel to a reduced nuclear translocation of NF-κB in LPS-induced endothelial cells. Our results suggest that RA-supplemented HDF is biocompatible and significantly suppressed inflammation induced in endothelial cells. In this respect, the use of HDF supplemented with RA could alleviate inflammation and improve long-term treatment of patients with renal failure on dialysis. Further clinical studies are required to confirm the effects.


Subject(s)
Humans , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Biocompatible Materials/pharmacology , Cinnamates/pharmacology , Depsides/pharmacology , Hemodialysis Solutions/pharmacology , Human Umbilical Vein Endothelial Cells/drug effects , Inflammation/drug therapy , Analysis of Variance , Cell Survival/drug effects , Cells, Cultured , Cytokines/analysis , Cytokines/drug effects , Formazans , Hemodialysis Solutions/chemistry , Human Umbilical Vein Endothelial Cells/metabolism , Immunoblotting , Inflammation/metabolism , Lipopolysaccharides , NF-kappa B/analysis , Nitric Oxide/analysis , Phosphorylation , Real-Time Polymerase Chain Reaction , Reproducibility of Results , Tetrazolium Salts
19.
Journal of Breast Cancer ; : 358-371, 2016.
Article in English | WPRIM | ID: wpr-28543

ABSTRACT

PURPOSE: The protein kinase C (PKC) family of serine-threonine kinases plays an important role in cancer cell progression. Thus, molecules that target PKC have potential as anticancer agents. The current study aims to understand the treatment of breast cancer cells with alkyl cinnamates. We have also explored the mechanistic details of their anticancer action and the underlying molecular signaling. METHODS: 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay was performed to measure the viability of MDAMB-231 breast cancer cells to assess the anticancer activity of these compounds. In addition, flow cytometry was performed to study the effect of alkyl cinnamates on the cell cycle and apoptosis. Immunoblotting and immunofluorescence techniques were performed to study PKC translocation, cytochrome c release, and modulation of the mitochondrial membrane potential in breast cancer cells targeted with alkyl cinnamates. RESULTS: The PKC agonist DM-2-8 translocated 16.6%±1.7% PKCα from cytosol to the plasma membrane and showed excellent anticancer activity with an half maximal inhibitory concentration (IC50) of 4.13±0.27 µg/mL against cancer cells. The treated cells had an abnormal morphology and exhibited cell cycle defects with G2/M arrest and reduced S phase. Cancer cells treated with DM-2-3, DM-2-4, or DM-2-8 underwent apoptosis as the major pathway of cell death, further confirmed by genomic DNA fragmentation. Furthermore, the mitochondrial membrane potential was perturbed, indicating involvement of the mitochondrial pathway of apoptosis. Immunolocalization studies revealed cytochrome c release from mitochondria to cytosol. Cancer cells treated with DM-2-8 and curcumin showed activation of caspase-9 and caspase-3 as downstream molecular components of the apoptotic pathway. Alkyl cinnamates also caused oxidative stress, which regulates the apoptotic machinery (DNA fragmentation), cell death, and morphological abnormalities in cancer cells. CONCLUSION: Alkyl cinnamates specifically target cancer cells through induction of PKC translocation and the mitochondrial pathway of apoptosis, and could be promising anticancer drugs.


Subject(s)
Humans , Antineoplastic Agents , Apoptosis , Breast Neoplasms , Breast , Caspase 3 , Caspase 9 , Caspases , Cell Cycle , Cell Death , Cell Membrane , Cinnamates , Curcumin , Cytochromes c , Cytosol , DNA Fragmentation , Flow Cytometry , Fluorescent Antibody Technique , Immunoblotting , Membrane Potential, Mitochondrial , Mitochondria , Oxidative Stress , Protein Kinase C , Protein Kinases , Protein Serine-Threonine Kinases , S Phase
20.
Chinese Journal of Integrated Traditional and Western Medicine ; (12): 437-444, 2016.
Article in Chinese | WPRIM | ID: wpr-328284

ABSTRACT

<p><b>OBJECTIVE</b>To explore the neuroprotective effect and mechanism of picroside II on extracellular regulated protein kinases1/2 (ERK1/2) signal transduction pathway in cerebral ischemia injuryrats. METHODS The middle cerebral artery occlusion (MCAO) model was established by inserting a monofilament into middle cerebral artery. Totally 96 successfully modeled Wistar rats were divided into the modelgroup, the treatment (picroside II) group, the Lipopolysachcaride (LPS) group, and the U0126 group according to random digit table. Each group was further divided into 3 subgroups, i.e. 6, 12, and 24 h sub-groups. Picroside II (20 mg/kg) was peritoneally injected to rats in the treatment group 2 h after ischemia.LPS (20 mg/kg) and Picroside II (20 mg/kg) were peritoneally injected to rats in the LPS group 2 h after ischemia. U0126-EtOH (20 mg/kg)and Picroside II (20 mg/kg) were peritoneally injected to rats in the U0126group 2 h after ischemia. Equal volume of normal saline was peritoneally injected to rats in the control groupand the model group. The neurobehavioral function was evaluated by modified neurological severity score(mNSS) test. The structure of neurons was observed using hematoxylin-eosinstaining (HE) staining. Theapoptotic cells were detected using terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) assay. The expression of phosphorylated extracellular signal-regulated protein kinase1,2 (pERK1,2) in cortex was detected using immunohistochemistry (IHC) and Western blot.</p><p><b>RESULTS</b>After cerebral ischemia injury neurological impairment score increased, the damage of neuron in the cortical area was aggravated, apoptotic cells increased in the model group as time went by. The expression of pERK1/2 increased more significantly in the model group than in the control group (P <0.05). The damage of neuron in the cortical area was milder, while apoptotic cells decreased, the expression of pERK1f2 obviously decreased more in the treatment group and the U0126 group (P < 0.05). The early damage of neuron in the cortical area was more severe, apoptotic cells and the expression of pERK12 were comparatively higher in early stage of the LPS group, but the expression of pERK1/2 was somewhat decreased in late stage.</p><p><b>CONCLUSIONS</b>Activating ERK12 pathway could mediate apoptosis and inflammatory reactions of neurons after cerebral ischemia injury. Picroside II could protect the nerve system possibly through reducing activation of ERKI2 pathway, inhibiting apoptosis of neurons and inflammation reaction.</p>


Subject(s)
Animals , Rats , Apoptosis , Brain Ischemia , Drug Therapy , Cinnamates , Pharmacology , Infarction, Middle Cerebral Artery , Drug Therapy , Iridoid Glucosides , Pharmacology , MAP Kinase Signaling System , Neurons , Pathology , Neuroprotective Agents , Pharmacology , Random Allocation , Rats, Wistar
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