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1.
Acta Pharmaceutica Sinica B ; (6): 405-420, 2024.
Article in English | WPRIM | ID: wpr-1011237

ABSTRACT

Lignans are a powerful weapon for plants to resist stresses and have diverse bioactive functions to protect human health. Elucidating the mechanisms of stereoselective biosynthesis and response to stresses of lignans is important for the guidance of plant improvement. Here, we identified the complete pathway to stereoselectively synthesize antiviral (-)-lariciresinol glucosides in Isatis indigotica roots, which consists of three-step sequential stereoselective enzymes DIR1/2, PLR, and UGT71B2. DIR1 was further identified as the key gene in respoJanuary 2024nse to stresses and was able to trigger stress defenses by mediating the elevation in lignan content. Mechanistically, the phytohormone-responsive ERF transcription factor LTF1 colocalized with DIR1 in the cell periphery of the vascular regions in mature roots and helped resist biotic and abiotic stresses by directly regulating the expression of DIR1. These systematic results suggest that DIR1 as the first common step of the lignan pathway cooperates with PLR and UGT71B2 to stereoselectively synthesize (-)-lariciresinol derived antiviral lignans in I. indigotica roots and is also a part of the LTF1-mediated regulatory network to resist stresses. In conclusion, the LTF1-DIR1 module is an ideal engineering target to improve plant Defenses while increasing the content of valuable lignans in plants.

2.
Chinese Journal of Experimental Traditional Medical Formulae ; (24): 140-148, 2024.
Article in Chinese | WPRIM | ID: wpr-999170

ABSTRACT

ObjectiveTo investigate the protective effect of total lignans of Arctii Fructus on the retinal tissue in the rat model of type 2 diabetes mellitus. MethodWistar rats were randomized into normal, model, solvent, Shuangdan Mingmu Capsules (618 mg·kg-1), and low-, medium-, and high-dose (100, 200, 400 mg·kg-1, respectively) total lignans of Arctii Fructus groups, with 16 rats in each group. The rat model was established by streptozotocin (STZ) combined with a high-fat diet and administrated with corresponding drugs by gavage once a day for 14 weeks. At the 14th week, blood was sampled for the collection of serum from the abdominal aorta after anesthesia, and bilateral eyeballs were collected and frozen. Hematoxylin-eosin (HE) staining was used to observe the histopathological changes of the retinal tissue in rats. The pathological changes of retinal vascular network in rats were observed by retinal vascular tissue digestion and mounting The levels of vascular endothelial growth factor (VEGF), tumor necrosis factor-α (TNF-α), and intercellular adhesion molecule-1 (ICAM-1) in the serum were determined by the ELISA kit. ResultCompared with the normal group, the solvent group showed pathological changes in the retinal tissue, reduced retinal ganglion cells (P<0.01), and retinal thinning (P<0.01), decreased E/P value in retinal blood vessels (P<0.01), and elevated serum levels of VEGF, TNF-α, and ICAM-1 (P<0.01). Compared with the model group, the total lignans of Arctii Fructus increased the retinal ganglion cells (P<0.01), thickened the retina (P<0.01), and lowered the serum levels of VEGF, TNF-α, and ICAM-1 (P<0.05, P<0.01). ConclusionTotal lignans of Arctii Fructus may lower the VEGF, TNF-α, and ICAM-1 levels to protect the retina.

3.
Acta Pharmaceutica Sinica B ; (6): 3545-3560, 2023.
Article in English | WPRIM | ID: wpr-1011135

ABSTRACT

Nonalcoholic steatohepatitis (NASH) is a spectrum of chronic liver disease characterized by hepatic lipid metabolism disorder. Recent reports emphasized the contribution of triglyceride and diglyceride accumulation to NASH, while the other lipids associated with the NASH pathogenesis remained unexplored. The specific purpose of our study was to explore a novel pathogenesis and treatment strategy of NASH via profiling the metabolic characteristics of lipids. Herein, multi-omics techniques based on LC-Q-TOF/MS, LC-MS/MS and MS imaging were developed and used to screen the action targets related to NASH progress and treatment. A methionine and choline deficient (MCD) diet-induced mouse model of NASH was then constructed, and Schisandra lignans extract (SLE) was applied to alleviate hepatic damage by regulating the lipid metabolism-related enzymes CES2A and CYP4A14. Hepatic lipidomics indicated that MCD-diet led to aberrant accumulation of phosphatidylethanolamines (PEs), and SLE could significantly reduce the accumulation of intrahepatic PEs. Notably, exogenous PE (18:0/18:1) was proved to significantly aggravate the mitochondrial damage and hepatocyte apoptosis. Supplementing PE (18:0/18:1) also deteriorated the NASH progress by up regulating intrahepatic proinflammatory and fibrotic factors, while PE synthase inhibitor exerted a prominent hepatoprotective role. The current work provides new insights into the relationship between PE metabolism and the pathogenesis of NASH.

4.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 516-526, 2023.
Article in English | WPRIM | ID: wpr-982721

ABSTRACT

Lignans derived from Eucommia ulmoides Oliver (Eucommia lignans) inhibit the progression of inflammatory diseases, while their effect on the progression of diabetic nephropathy (DN) remained unclear. This work was designed to assess the function of Eucommia lignans in DN. The major constituents of Eucommia lignans were analyzed by UPLC-Q-TOF-MS/MS. The binding between Eucommia lignans and aldose reductase (AR) was predicted by molecular docking. Eucommia lignans (200, 100, and 50 mg·kg-1) were used in model animals to evaluate their renal function changes. Rat glomerular mesangial cells (HBZY-1) were transfected with sh-AR, sh-AMPK, and oe-AR in the presence of high glucose (HG) or HG combined with Eucommia lignans to evaluate whether Eucommia lignans affected HG-induced cell injury and mitochondrial dysfunction through the AR/Nrf2/HO-1/AMPK axis. Eucommia lignans significantly attenuated the progression of DN in vivo. Eucommia lignans notably reversed HG-induced upregulation of inflammatory cytokines and mitochondrial injury, while downregulating the levels of Cyto c, caspase 9, AR, and NOX4 in HBZY-1 cells. In contrast, HG-induced downregulation of Nrf2, HO-1 and p-AMPKα levels were abolished by Eucommia lignans. Meanwhile, knockdown of AR exerted similar therapeutic effect of Eucommia lignans on DN progression, and AR overexpression reversed the effect of Eucommia lignans. Eucommia lignans alleviated renal injury through the AR/Nrf2/HO-1/AMPK axis. Thus, these findings might provide evidence for the use of Eucommia lignans in treating DN.


Subject(s)
Animals , Rats , AMP-Activated Protein Kinases/genetics , Diabetes Mellitus , Diabetic Nephropathies/prevention & control , Eucommiaceae/metabolism , Lignans/therapeutic use , Molecular Docking Simulation , NF-E2-Related Factor 2/metabolism , Tandem Mass Spectrometry
5.
Chinese Herbal Medicines ; (4): 463-469, 2023.
Article in English | WPRIM | ID: wpr-982515

ABSTRACT

OBJECTIVE@#To investigate the chemical constituents from the leaves of Jatropha curcas and evaluate their inhibition on lipopolysaccharide (LPS)-activated BV-2 microglia cells.@*METHODS@#The n-BuOH extract of the leaves of J. curcas was isolated by macroporous adsorption resin, silica gel, ODS, column chromatography and semi-preparative HPLC. The structures of the compounds were identified by MS, NMR, ECD, and other spectroscopic methods. In addition, anti-neuroinflammatory effects of isolated compounds were evaluated by measuring the production of nitric oxide (NO) in over-activated BV-2 cells.@*RESULTS@#Seventeen compounds, including (7R,8S)-crataegifin A-4-O-β-D-glucopyranoside ( 1), (8R,8'R)-arctigenin ( 2), arctigenin-4'-O-β-D-glucopyranoside ( 3), (-)-syringaresinol ( 4), syringaresinol-4'-O-β-D-glucopyranoside ( 5), (-)-pinoresinol ( 6), pinoresinol-4'-O-β-D-glucopyranoside ( 7), buddlenol D ( 8), (2R,3R)-dihydroquercetin ( 9), (2S,3S)-epicatechin ( 10), (2R,3S)-catechin ( 11), isovitexin ( 12), naringenin-7-O-β-D-glucopyranoside ( 13), chamaejasmin ( 14), neochamaejasmin B ( 15), isoneochamaejasmin A ( 16), and tomentin-5-O-β-D-glucopyranoside ( 17) were isolated and identified. Compounds 2, 4 and 8 significantly inhibited the release of NO in BV-2 microglia activated by LPS, with IC50 values of 18.34, 29.33 and 26.30 μmol/L, respectively.@*CONCLUSION@#Compound 1 is a novel compound, and compounds 2, 3, 8, 14- 17 are isolated from Jatropha genus for the first time. In addition, the lignans significantly inhibited NO release and the inhibitory activity was decreased after glycosylation.

6.
China Journal of Chinese Materia Medica ; (24): 105-113, 2023.
Article in Chinese | WPRIM | ID: wpr-970506

ABSTRACT

The chemical constituents from the fruits of Morinda citrifolia were systematically explored by chromatographic fractionation methods including silica gel, octadecylsilyl(ODS) gel, Sephadex LH-20 gel, and preparative high performance liquid chromatography(pre-HPLC). The chemical structures of all isolated compounds were identified on the basis of their physicochemical properties, spectroscopic analyses, as well as the comparisons of their physicochemical and spectroscopic data with the reported data in literature. As a result, 22 isolated compounds from the 90% ethanol extract of the fruits of M. citrifolia were identified, which were moricitritone(1), 2'-deoxythymidine(2), cyclo-(L-Pro-L-Tyr)(3), methyl-5-hydroxy-2-pyridinecarboxylate(4), methyl pyroglutamate(5), bisbenzopyran(6), epipinoresinol(7), 3, 3'-bisdemethyl pinoresinol(8), 3, 3'-bisdemethyltanegool(9), trimesic acid(10), crypticin B(11), kojic acid(12), vanillic acid(13), protocatechoic acid(14), 5-hydroxymethyl furfural(15), blumenol A(16), 1-O-(9Z, 12Z-octadecadienoyl) glycerol(17), mucic acid dimethylester(18), methyl 2-O-β-D-glucopyranosylbenzoate(19), 2-phenylethyl-O-β-D-glucoside(20), scopoletin(21), and quercetin(22). Among them, compound 1 was a new pyrone derivative, compounds 2, 4-7, 10-12, and 17 were isolated from the plants belonging to Morinda genus for the first time, and compound 18 was obtained from M. citrifolia for the first time. Moreover, on the basis of testing the activities of all isolated compounds on inhibiting the proliferation of synovial fibroblasts in vitro by MTS assay, the anti-rheumatoid arthritis activities of all isolated compounds were initially evaluated. The results showed that compounds 1-6, 9, 19, and 20 exhibited remarkable anti-rheumatoid arthritis activities, which displayed the inhibitory effects on the proliferation of MH7A synovial fibroblast cells with the IC_(50) values in the range of(3.69±0.08) to(168.96±0.98) μmol·L~(-1).


Subject(s)
Fruit/chemistry , Morinda/chemistry , Synoviocytes , Cell Proliferation , Arthritis
7.
China Journal of Chinese Materia Medica ; (24): 415-420, 2023.
Article in Chinese | WPRIM | ID: wpr-970478

ABSTRACT

Ten lignans were isolated from the ethanol extract of stems and branches of Rhododendron ovatum through column chromatography over silica gel, ODS, Sephadex LH-20, and MCI-gel resin and semi-preparative RP-HPLC. The structures of all compounds were elucidated by extensive spectroscopic data analysis(UV, IR, HR-ESI-MS, ECD and NMR) as(-)-4-epi-lyoniresinol-9'-O-α-L-rhamnopyranoside(1),(+)-lyoniresinol-3α-O-α-L-rhamnopyranoside(2),(+)-5'-methoxyisolariciresinol-9'-O-α-L-rhamnopyranoside(3),(-)-lyoniresinol-3α-O-β-D-glucopyranoside(4),(+)-lyoniresinol-3α-O-β-D-glucopyranoside(5),(-)-4-epi-lyoniresinol-9'-O-β-D-glucopyransoide(6), racemiside(7), neociwujiaphenol(8),(+)-syringaresinol(9), and homohesperitin(10). Among them, compound 1 was a new aryltetralin-type lignan. All the isolated lignans were tested for antioxidant activities in Fe~(2+)-cysteine induced rat liver microsomal lipid peroxidation in vitro, and compounds 8 and 9 showed antioxidant activities on the formation of malondiadehyde(MDA) in rat liver microsomes at 1×10~(-5) mol·L~(-1), with significant inhibitory rates of 75.20% and 91.12%, respectively.


Subject(s)
Animals , Rats , Glucosides/chemistry , Rhododendron , Antioxidants/pharmacology , Lignans/chemistry , Plant Stems
8.
China Journal of Chinese Materia Medica ; (24): 1892-1898, 2023.
Article in Chinese | WPRIM | ID: wpr-981408

ABSTRACT

The present study aimed to explore the chemical constituents from the stems and leaves of Cephalotaxus fortunei. Seven lignans were isolated from the 75% ethanol extract of C. fortunei by various chromatographic methods, including silica gel, ODS column chromatography, and HPLC. The structures of the isolated compounds were elucidated according to physicochemical properties and spectral data. Compound 1 is a new lignan named cephalignan A. The known compounds were identified as 8-hydroxy-conidendrine(2), isolariciresinol(3), leptolepisol D(4), diarctigenin(5), dihydrodehydrodiconiferyl alcohol 9'-O-β-D-glucopyranoside(6), and dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(7). Compounds 2 and 5 were isolated from the Cephalotaxus plant for the first time.


Subject(s)
Cephalotaxus , Lignans/analysis , Plant Leaves/chemistry , Ethanol , Chromatography, High Pressure Liquid
9.
Braz. dent. sci ; 25(3): 1-9, 2022. tab, ilus
Article in English | LILACS, BBO | ID: biblio-1373090

ABSTRACT

Objective: This in vitro study evaluated the effect of neolignan-containing solutions on dentin biomodification previously applied to the bonding procedure in adhesive restorations. Material and Methods: Neolignans, dehydrodieugenol B­CP1 and dehydrodieugenol B methyl ether­CP2, were isolated from Nectandra leucanthaand two aqueous solutions containing 0.13% neolignans, 0.2% propylene glycol and 3.0% ethanol were prepared. Bovine teeth were ground flat to obtain 2-mm thick specimens which received resin composite restorations (N=10). The neolignan solutions were applied before the bonding procedure (60 s). Experimental groups were: control, untreated group, 0.12% chlorhexidine gel, 0.13% CP1 solution, and 0.13% CP2 solution. A push-out bond strength test was conducted (0.5 mm/min). Bovine tooth sections (0.5×1.7×7.0 mm) were also obtained to assess the modulus of elasticity and mass change after treatment (N=15). A three-point bending test evaluated the elastic modulus of fully demineralized dentine beams after immersion in the solutions. The data were statistically analyzed (α = 0.05). Results: The bond strength of the restorations to dentin was significantly improved by the treatment with neolignan-containing solutions, irrespective of the evaluation time (p<0.05). After 6 months, a significant reduction in the bond strength was observed in the groups treated with the solutions (p>0.05), but the means were significantly higher than the control groups (p<0.05). The elastic modulus of demineralized dentin was significantly improved after the treatment with the solutions (p<0.05). All groups lost mass weight. Conclusion: The solutions improved the in vitro longevity of bonded restorations, possibly due to the dentin biomodification effect of the neolignans.(AU)


Objetivo: Este estudo in vitro avaliou o efeito de soluções contendo neolignanas na biomodificação da dentina aplicadas previamente à restaurações adesivas. Material e Métodos: Neolignanas, desidrodieugenol B­CP1 e éter metílico de desidrodieugenol B-CP2, foram isolados da espécie Nectandra leucantha e duas soluções aquosas contendo 0,13% de neolignanos, 0,2% de propilenoglicol e 3,0% de etanol foram preparadas. Dentes bovinos foram lixados para obter espécimes de 2 mm de espessura e preparos cavitários restaurados com resina composta (N=10). As soluções foram aplicadas em dentina antes do procedimento adesivo (60 s). Os grupos experimentais foram: controle, grupo não tratado, gel de clorexidina 0,12%, solução de CP1 a 0,13% e solução de CP2 a 0,13%. Foi realizado o teste de resistência de união push-out (0,5 mm/min). O módulo de elasticidade e a alteração de massa após tratamento da dentina (0,5×1,7×7,0 mm) foram também avaliados em teste de flexão de três pontos (N=15). Os dados foram analisados estatisticamente (α=0,05). Resultados: A resistência de união das restaurações à dentina melhorou significativamente com o tratamento com as soluções, independentemente do tempo de avaliação (p<0,05). Após 6 meses, foi observada redução significativa da resistência de união nos grupos tratados com as soluções (p>0,05), com médias significativamente maiores do que nos grupos controle (p<0,05). O módulo de elasticidade da dentina desmineralizada aumentou significativamente após tratamento com as soluções (p<0,05). Todos os grupos perderam massa, independentemente do tratamento. Conclusão: As soluções melhoraram in vitroa longevidade das restaurações adesivas, possivelmente devido ao efeito biomodificador da dentina das neolignanas(AU)


Subject(s)
Animals , Cattle , Plants, Medicinal , Lignans , Collagen Type I , Dental Restoration, Permanent , Dentin
10.
Journal of China Pharmaceutical University ; (6): 93-98, 2022.
Article in Chinese | WPRIM | ID: wpr-920656

ABSTRACT

@#Eubhorbia neriifolia L. is a plant of Euphorbia family.Five known lignans were isolated from the aerial parts of E. neriifolia L. by silica gel for column chromatography and preparative high-performance liquid chromatography (HPLC).Their potential antitumor activities were evaluated in vitro.Compound 2 exhibited proliferation inhibition and cytotoxicity against esophageal squamous cancer cells, especially KYSE-410 and KYSE-450 cells.Further analyses showed that compound 2 could significantly induce apoptosis through the activation of caspase 3/9 and down-regulation of the Bcl-2/Bax protein ratio.These results suggested that compound 2 had a significant inhibitory effect on the esophageal squamous cancer cells, especially KYSE-410, which deserves further research as a potential antitumor agent.

11.
Bol. latinoam. Caribe plantas med. aromát ; 20(5): 443-462, sept. 2021. ilus
Article in English | LILACS | ID: biblio-1368583

ABSTRACT

Drimys winteri JR et G. Forster var chilensis (DC) A. is a tree native to central and southern Chile. Also it found in part of Argentina. It is abundant in wet swampy localities from sea level to an altitude of 1700 m. This tree is sacred for the Mapuche culture; it is used in folk medicine in such as inflammatory and painful processes. Phytochemical studies have demonstrated that this plant contains mainly sesquiterpenes of the drimane type, flavonoids, essential oils, phytosterols and some lignans. These drimanes have attracted interest because of their antifeedant, plant growth regulation, cytotoxic, antimicrobial and insecticidal properties. The objective of this review is to establish clearly the phytochemistry and biological activity of Drimys winteri JR et G. Forster var chilensis (DC) A. Articles based on other varieties are not considered.


Drimys winteri JR et G. Forster var chilensis (DC) A. es un árbol nativo del centro y sur de Chile. También se encuentra en parte de Argentina. Es abundante en localidades pantanosas y húmedas desde el nivel del mar hasta una altitud de 1700 m. Este árbol es sagrado para la cultura mapuche. Se utiliza en la medicina popular para tratar enfermedades como procesos inflamatorios y dolorosos. Los estudios fitoquímicos han demostrado que esta planta contiene principalmente sesquiterpenos del tipo drimano, flavonoides, aceites esenciales, fitoesteroles y algunos lignanos. Estos drimanos han despertado interés debido a sus propiedades antialimentarias, regulación del crecimiento de las plantas, propiedades citotóxicas, antimicrobianas e insecticidas. El objetivo de este examen es establecer claramente la fitoquímica y la actividad biológica de Drimys winteri JR et G. Forster var chilensis (DC) A. No se consideran los artículos basados en otras variedades D. winteri var winteri.


Subject(s)
Oils, Volatile/chemistry , Drimys/chemistry , Sesquiterpenes/analysis , Flavonoids/analysis , Lignans/analysis
12.
China Pharmacy ; (12): 2599-2604, 2021.
Article in Chinese | WPRIM | ID: wpr-904517

ABSTRACT

OBJECTIVE:To stud y the effects of “green removing ”processing technology of fresh fruit of Schisandra chinensis after harvested on the quality of medicinal material ,and to provide new ideas for the scientific and rational processing of Chinese medicinal material. METHODS :Fifteen fresh fruits of S. chinensis were used as samples ,with 3 samples in each group. The sample were processed preliminarily by 5 methods,such as drying at 50 ℃,drying in the sun ,drying at 50 ℃ after“green removing”processing with microwave ,drying at 50 ℃ after“green removing ”processing with blanching ,drying at 50 ℃ after “green removing ”processing with steaming. HPLC fingerprints of 15 batches of dried S. chinensis products were established and similarity evaluation was conducted according to Similarity Evaluation System of TCM Chromatographic Fingerprints (2012 edition). Cluster analysis was used to evaluate the similarity of dried S. chinensis products with different processing methods. At the same time ,HPLC method was adopted to determine the content changes of seven lignans in dried products ,such as schisandrol A , schisandrol B ,schisantherin A ,schisantherin B ,schizandrin A ,schisandrin B and schisandrin C. RESULTS :A total of 7 common peaks were obtained in the fingerprints of 15 batches of dried S. chinensis products. Except that the similarity between the chromatograms of dried samples in the sun and the control fingerprint was relatively low ,the similarities of chromatograms of dried products by other processing methods were greater than 0.900. Cluster analysis showed that 6 samples dried at 50 ℃ after“green removing”processing with microwave and dried at 50 ℃ after“green removing ”processing with blanching were grouped into the first category ;3 samples dried at 50 ℃ after“green removing”processing with steaming were grouped into the second category ;6 samples dried at 50 ℃ and dried in sun were grouped into the third category. The content determination results showed that there was no significant difference in the total content of seven lignans in the samples dried at 50 ℃ and dried in the sun (P>0.05). The total contents of seven lignans in the samples dried at 50 ℃ after“green moving ” processing with microwave ,blanching and steaming were significantly higher than those dried at 50 ℃ and dried in sun (P<0.01). CONCLUSIONS:The quality of S. chinensis samples dried after “green moving ”processing with microwave and blanching is better than those directly dried in sun and dried in oven.

13.
China Journal of Chinese Materia Medica ; (24): 2519-2526, 2021.
Article in Chinese | WPRIM | ID: wpr-879156

ABSTRACT

The chemical constituents from the stems and leaves of Morinda citrifolia were isolated and purified by column chromatography methods with silica gel, ODS, Sephadex LH-20 and preparative high performance liquid chromatography(HPLC). The structures of the isolated compounds were identified by physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in literature. 17 compounds were isolated from the 90% ethanol extract of the stems and leaves of M. citrifolia, and were identified as 9,10-dihydroxy-4, 7-megastigmadien-3-one(1), 5,12-epoxy-6,9-hydroxy-7-megastigmen-3-one(2), fukinone(3), β-eudesmol(4), sarmentol F(5), 4, 5-dihydroblumenol A(6), 3-hydroxy-β-ionone(7), aristol-8-en-1-one(8), ergosta-7-en-3β-ol(9), ergosta-7-ene-3β,5α,6β-triol(10),(22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol(11), olivil(12), 4-epi-larreatricin(13), chushizisin Ⅰ(14), rabdosia acid A(15), glycerol monolinoleate(16) and(9Z,12Z,15Z)-2,3-dihydroxypropyl octadeca-trienoate(17). All compounds were isolated from M. citrifolia for the first time. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their inhibitory activities on the proliferation of synoviocytes in vitro using MTS met-hod. Compounds 1-11 showed significant anti-rheumatoid arthritis activities, displaying the inhibitory effects on the proliferation of MH7 A synovial fibroblast cell with the IC_(50) values ranging from(38.69±0.86) to(203.45±1.03) μmol·L~(-1).


Subject(s)
Cell Proliferation , Chromatography, High Pressure Liquid , Molecular Structure , Morinda , Synoviocytes
14.
China Journal of Chinese Materia Medica ; (24): 2072-2078, 2021.
Article in Chinese | WPRIM | ID: wpr-879132

ABSTRACT

The chemical constituents from the extract of the twigs of Euscaphis konishii with anti-hepatoma activity were investigated, twelve compounds by repeated chromatography with silica gel, Sephadex LH-20 and preparative-HPLC. The structures of the chemical components were elucidated by spectroscopy methods, as konilignan(1),(7R, 8S)-dihydrodehydrodico-niferylalcohol-9-O-β-D-glucopyranoside(2),illiciumlignan B(3),threo-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-panediol(4),erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-panediol(5), matairesinol(6), wikstromol(7), isolariciresinol(8),(+)-lyoniresinol(9), 4-ketopinoresinol(10), syringaresin(11), and vladinol D(12). Among them, compound 1 is a new lignan. Compounds 10 and 12 had moderate inhibitory activity on HepG2 cells, with IC_(50) values of 107.12 μmol·L~(-1) and 183.56 μmol·L~(-1), respectively.


Subject(s)
Chromatography, High Pressure Liquid , Lignans/pharmacology , Plant Extracts/pharmacology
15.
Chinese Herbal Medicines ; (4): 157-166, 2021.
Article in Chinese | WPRIM | ID: wpr-953665

ABSTRACT

Kadsura belongs to the Schisandroideae subfamily of Magnoliaceae. Plants from genus Kadsura are widely distributed in the South and Southwest of China. The plants of the genus are widely used as folk medicine for a long time in history, with the functions of relieving pain, promoting ‘qi’ circulation, activating blood resolve stasis, and applications in the treatment of rheumatoid arthritis and gastroenteric disorders. Lignans are the primary characteristic constituents with various biological activities of plants from genus Kadsura. This paper summarized 81 lignans isolated from the plants of genus Kadsura over the past eight years (from 2014 to 2021), which belong to five types: dibenzocyclooctadienes, spirobenzofuranoid dibenzocyclooctadienes, aryltetralins, diarylbutanes and tetrahydrofurans. Each type of these lignans possess typical characteristics in proton magnetic resonance (

16.
Acta Pharmaceutica Sinica ; (12): 2951-2954, 2020.
Article in Chinese | WPRIM | ID: wpr-862297

ABSTRACT

The chemical constituents from ethyl acetate extract of Gleditsiae spina were isolated and purified by various chromatographic methods such as MCI gel CHP-20, ODS, Sephadex LH-20, silica gel and semi-preparative HPLC. Seven lignans were isolated and identified by spectroscopic data analyses as (7R,8S,7'E,7''S,8''R)-buddlenol P (1), (+)-syringaresinol (2), (+)-isolariciresinol (3), (7S,8R)-cedrusin (4), (7S,8R)-4,9,9'-trihydroxy-3,3'-dimethoxy-7,8-dihydrobenzofuran-1'-propylneolignan (5), 3',4-O-dimethylcedrusin (6), balanophonin (7). Among them, compound 1 is a new lignan, compounds 2-7 are isolated from the Gleditsia L. for the first time. MTT method was used to investigate the effect of compounds 2-7 on LPS-induced injury of NRK-52e cells. As a result, compounds 2, 3 and 7 exhibit protective effects against LPS-induced damage to NRK-52e cells.

17.
Chinese Pharmaceutical Journal ; (24): 1325-1330, 2020.
Article in Chinese | WPRIM | ID: wpr-857606

ABSTRACT

OBJECTIVE: To study the chemical constituents of bamboo juice. METHODS: The compounds were isolated and purified by column chromatography on silica gel, ODS, macroporous resin, MPLC and HPLC. Their structures were elucidated by NMR spectroscopic evidence and compared with those in literature. RESULTS: Fifteen compounds were isolated and identified as (+)-lyoniresinol-3α-O-β-D-glucopyranoside (1), 5, 5'-dimethoxylariciresinol-4'-O-β-D-glucopyranoside (2), syringaresinol 4'-O-β-D-glucopyroside (3), (-)-4-epi-lyoniresinol (4), (-)-lyoniresinol -2α-O-β-D-glucopyranoside (5), (+)-lyoniresinol (6), 8, 8'-bisdihydrosiringenin glucoside (7), 2, 4, 6-trimethoxyphenyl-1-O-β-D-glucopyranoside (8), threo-8S-7-meth-oxysyringylglycerol (9), salidroside (10), (7S, 8R)syringoylglycerol (11), syringaldehyde (12), 2, 6-dimethoxy-1, 4-benzoquinone (13), n-butyl-β-D-fructopyranoside (14), and n-butyl pyroglutamate (15).CONCLUSION: Compounds 1-11 and 14-15 are isolated from bamboo juice for the first time. Compounds 14 and 15 are β-D-fructopyranoside and pyroglutamic acid artifacts produced during the extraction.

18.
Chinese Traditional and Herbal Drugs ; (24): 36-42, 2020.
Article in Chinese | WPRIM | ID: wpr-846689

ABSTRACT

Objective: To study chemical constituents of Cephalotaxus fortunei. Methods: The chemical constituents were separated and purified by preparative thin-layer chromatography, silica gel, ODS, HP20 macroporous resin and Sephadex LH-20 gel column chromatography, and semi-preparative HPLC. Their structures were determined by NMR and ESI-MS spectroscopic techniques. Results: Seventeen lignans were isolated from the ethanol extracts of C. fortunei and their structures were identified as shonanin (1), arctigenin (2), α-conidendrin (3), matairesinol (4), nortrachelogenin (5), epinortrachelogenin (6), (7'S)- hydroxymatairesinol (7), (7'R)-hydroxymatairesanol (8), (7'S)-hydroxyarctigenin (9), secoisolariciresinol (10), 4,4'-di-O-methylcephafortin A (11), 5-(3″,4″-dimethoxyphenyl)-3-hydroxy-3-(4'-hydroxy-3'-methoxybenzyl)-4-hydroxymethyl-dihydrofuran-2-one (12), cephafortin B (13), dihydrodehydrodiconiferyl alcohol (14), 7R,8S-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (15), 7R,8R-4,7,9,9'- tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (16), and threo-1,2-bis-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (17). Conclusion: Compounds 3, 6, 10 and 17 were isolated from genus Cephalotaxus for the first time, and compounds 4, 5, 7-9, 12 and 14 were isolated from C. fortunei for the first time.

19.
Chinese Traditional and Herbal Drugs ; (24): 549-556, 2020.
Article in Chinese | WPRIM | ID: wpr-846682

ABSTRACT

Semen Hertospermi (Bolengguazi in Chinese, BL), as well-known Tibetan medicine, is one of commonly used drugs by Tibetan healers for the treatment of liver diseases and cholic diseases. Modern research indicated that BL had multiple pharmacological effects including hepatoprotection, anti-hepatitis B virus and anti-liver fibrosis, etc. And the lignans are the major pharmacodynamic substances. The fatty acid, polysaccharides and other ingredients also have hepatoprotective effects. This article mainly reviews the pharmacodynamic substances, pharmacological effects, preparation research and development related to anti-liver disease, so as to provide reference and thinking for the research and application of BL and preparations development in the prevention of liver disease and promote the modern research and development of ethnic medicine.

20.
Chinese Traditional and Herbal Drugs ; (24): 2402-2407, 2020.
Article in Chinese | WPRIM | ID: wpr-846450

ABSTRACT

Objective: To investigate the lignans compounds constituents of Lavandula angustifolia. Methods: The chemical constituents were isolated and purified by TLC, silica gel, MCI-gel, and RP-HPLC, and their structures were identified by analysis of spectroscopic evidences and physicochemical properties. Results: A total of 11 constituents were isolated from L. angustifolia and elucidated as pinoresinol (1), syringaresinol (2), fraxiresinol-4'-O-β-D-glucopyranoside (3), syringaresinol-4'-O-β-D-glucopyranoside (4), 8-hydroxypinoresinol-4-O-β-D-glucopyranoside (5), rel-(2α,3β)-7-O-methylcedrusin (6), lariciresinol-4'-O-β-D-glucoside (7), (2S,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzofuran-5-(trans) propen-1-ol-3-O-β-glucoside (8), (7S,8R)-dihydrodehydrodiconiferyl alcohol-9-β-D-glucopyranoside (9), (7R,8R)-7,8-dihydro-9'-hydroxyl-3'-methoxyl-8- hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1'-benzofuranpropanol-9'-O-β-D-glucopyranoside (10), and (E)-3-((2S,3S)-2-(4- hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl) allyl-2-hydroxyacetate (11). Conclusion: The 11 compounds are isolated from this plant for first time.

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