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ObjectiveTo determine the chemical constituents of burdock （Arctium lappa） leaves， and elucidate dynamic accumulation rule of four main components， in order to provide the basis for determining the suitable harvest time of burdock leaves. MethodSilica gel， macroporous resin， Sephadex LH-20， octadecylsilane chemically bonded silica （ODS）， microporous resin （MCI） column chromatography and reversed-phase preparative high performance liquid chromatography （HPLC） were used to isolate the main chemical constituents in burdock leaves. Their chemical structures were elucidated by spectroscopic techniques. HPLC-diode array detector （DAD） was used to analyze the dynamic accumulation of four components in burdock leaf. HPLC-DAD was performed on a Shim-pack GIST C18 column （4.6 mm×250 mm， 5 μm） with mobile phase of acetonitrile （A）-0.3% phosphoric acid aqueous solution （B） （0-9 min， 13%A； 9-10 min， 13%-24%A； 10-30 min， 24%A）， flow rate of 1.0 mL·min-1， column temperature of 40 ℃， and detection wavelength at 328 nm. ResultSeventeen compounds were isolated from burdock leaves， and identified as caffeic acid （1）， rutin （2）， kaempferol-3-O-rutinoside （3）， quercetin-3-O-β-D-glucopyranoside （4）， kaempferol-3-O-β-D-glucopyranoside （5）， chlorogenic acid （6）， isochlorogenic acid A （7）， daucosterol （8）， ursolic acid （9）， anemarrhenoside B （10）， （-）-secoisolariciresinol （11）， vladinol D （12）， melitensin （13）， esculetin （14）， 1-（-2-ethylphenyl）-1，2-ethanediol （15）， 1-（-4-ethylphenyl）-1，2-ethanediol （16）， 3-hydroxy-1-（4-hydroxy-3，5-dimethoxyphenyl）-1-propanone （17）. The contents of chlorogenic acid， rutin and kaempferol-3-O-rutinoside in burdock leaves showed an upward trend from April to August， and reached the highest in August. And the content of isochlorogenic acid A firstly increased and then decreased from April to August， and reached the highest in July. ConclusionCompounds 10， 12-17 were isolated from Arctium for the first time. Taking the contents of chlorogenic acid， rutin， kaempferol-3-O-rutinoside， and isochlorogenic acid A as indicators， considering the comprehensive development and utilization of burdock roots and leaves， it is recommended to harvest burdock leaves in mid-August.
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Flavonoid glycosides are the main active constituents of Epimedii Folium and its related plants. They can be divided into polyglycosides and low glycosides according to the number of glycosyl group. The polyglycosides of Epimedii Folium can be transformed into low glycosides after biotransformation ；pharmacological activities of low glycosides in anti-tumor ，tonifying kidney yang and anti-osteoporosis are stronger than those of polyglycosides. In this paper ， the research progress about biotransformation technology of flavonoid glycosides of Epimedii Folium was reviewed. It was found that the main biotransformation pathway of flavonoid glycosides of Epimedii Folium was to obtain low glycosides by removing glycosyl group ； related methods were mainly enzymatic hydrolysis and microbial transformation ，and also included plant cell transformation ，acid hydrolysis method and synthesis method.
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@#Chemical constituents from the air dried parts of Cichorium glandulosum were studied. The chemical constituents of C. glandulosum were separated and purified by means of silica gel, Sephadex-LH 20, ODS column chromatography and semi-preparative high performance liquid chromatography. The structure was elucidated by physicochemical characteristics and spectral data. One new flavonoid glycoside was isolated from C. glandulosum, and identified as quercetin-3-O-［6″-O-(3-ethoxy-1, 3-dioxopropyl)］-β-D-glucopyranoside(1).
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Flavonoid glycosides (FGs) are secondary metabolites of many plants widely found in nature, and exhibit significant biological activities, such as anticancer, antioxidant and antimicrobial. According to the glycosidic bonds, FGs are divided into flavonoid O-glycosides and flavonoid C-glycosides. The main metabolic processes of FGs in vivo were specific hydrolysis in the gastrointestinal tract and glucuronidation in liver. Glucose, xylose, rhamnose and other glycosyl groups were hydrolyzed to produce secondary glycosides or aglycones in the gastrointestinal tract that were absorbed into blood, and then further glucuronidation and methylation metabolites are mainly produced by phase II metabolism in liver. This article reviews the metabolism in vivo and biotransformation in vitro of some typical natural flavonoid glycosides exited in Chinese materia medica (CMMs), such as flavonoid O-glycosides in Epimedii Folium, Glycyrrhizae Radix et Rhizoma, Scutellariae Radix, Citri Reticulatae Pericarpium, and Cirsii Japonici Herba, and flavonoid C-glycosides in Anemarrhenae Rhizoma and Puerariae Lobatae Radix. The investigation of the metabolisms of FGs in vivo is helpful for the clarification of the effective ingredients in CMMs, which will provide the basis for new drugs development based on metabolites in vivo.
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Objective: Cancer is considered as one of the top reasons of death and the number of cases increasing gradually. Cancer is severe clinical difficulty to the health caution system. This study explored two novel polyphenols of Afrocarpus gracilior Pilger growing in Egypt and evaluated their cytotoxic activity. Methods: Methanolic (80%) extract of the leaves of A. gracilior was subjected to column chromatography; the chemical structures of the isolated compounds were established by advanced spectral techniques: UV, 1H, 13C NMR, two dimensional NMR (2D NMR) and electron spray ionization mass spectroscopy (ESI-MS). Compounds 1 and 2 were studied for their cytotoxic activity against hepatocellular carcinoma (Hep-G2) using sulforhodamine B (SRB) assay. Furthermore the pharmacokinetics profiles of these molecules were accessed by employing Petra/Osiris/Molinspiration (POM) analyses. Results: Two novel C-flavonoid glycosides were isolated [1: Apigenin 8-C-β-D-glucopyranosyl-(1```→4``)-O-β-D-glucopyranoside] and [2: 7-O methyl-luteolin 8-C-β-glucopyranosyl-(1```→4``)-O-β-D-glucopyranoside]. They exhibited significant cytotoxic activity (IC50 = 9.02 and 15.61 µg/ml, respectively) against Hep-G2 cells. The POM analyses revealed that the activity of these two compounds depends on the presence of glucosyl and alkyl groups at the internal and terminal atmosphere of the compounds. Conclusion: These findings demonstrated that the leaves of A. gracilior contain a series of bioactive polyphenolic compounds with significant cytotoxic properties against hepatocellular carcinoma and may be used as alternative anticancer agents for doxorubicin. On the basis of POM calculations, it will be interesting to develop some alternative flavones because the deglucosylated derivatives have a better drug score than parent molecules. This preliminary study will be extended to other strains of cancer.
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Objective: To compare the pharmacokinetics of naringin and neohesperidin after oral administration of Zhishi total flavonoid glycosides (ZSTFG) extracted from Aurantii Fructus Immaturus in normal and gastrointestinal motility disorders (GMD) mice. Methods: ZSTFG was orally given to normal and GMD mice induced by atropine or dopamine. The plasma samples were incubated with β-glucuronidase/sulfatase, the total (free + conjugated) naringenin and hesperitin were extracted with acetonitrile. The validated HPLC-MS/MS method was successfully applied to the pharmacokinetic study. Results: The results showed that, compared with the normal group, AUC0–∞, AUC0–t and Cmax for total naringenin and hesperitin were significantly higher (P < 0.01 or P < 0.05), while CLZ/F for total naringenin and hesperitin was significantly lower (P < 0.01) in the GMD group. Tmax, t1/2z, MRT0-t, and MRT0-∞ for naringenin were longer (P < 0.01) in the GMD group than those in the normal group. Conclusion: The results showed that there were significant differences in pharmacokinetic parameters of naringenin and hesperitin between normal and GMD groups. It was suggested that the absorption of naringenin and hesperitin was increased, and the elimination processes of naringenin and hesperitin were slower in the GMD group than the normal group. The data are of value for further pharmacological studies of ZSTFG and would be useful to provide a reference for improving the therapeutic regimen of ZSTFG in clinical trials.
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Objective:HPLC for the determination of five components in Descurainiae Semen was established to investigate the change rule of contents of five components in the herb before and after being processed. Method:The contents of quercetin-3-O-β-D-glucose-7-O-β-D-gentiobioside(QGG),sinapic acid,quercetin-3-O-β-D-glucopyranoside(QG),isorhamnetin-3-O-β-D-glucopyranoside(IG) and 1,2-di-O-sinapoyl-β-D-glucopyranose(SG) was determined simultaneously by HPLC,the change rule of contents of these components before and after processing and its reasons were analyzed.Waters Symmetry® C18 column(4.6 mm×250 mm,5 μm) was employed,and the mobile phase was acetonitrile(A)-1% acetic acid aqueous solution(B) for gradient elution(0-5 min,5%-10%A;5-15 min,10%-13%A;15-23 min,13%-20%A;23-43 min,20%-25%A;43-46 min,25%A;46-55 min,25%-40%A;55-60 min,40%A).The flow rate was 1 mL·min-1.The detection wavelength was set at 265 nm,the injection volume was 10 μL,and the column temperature was 30℃. Result:Contents of the above five components before processing were 0.114 3%,0.041 6%,0.036 2%,0.022 6% and 0.097 6%;after processing,the contents of these five components turn into 0.107 4%,0.011 3%,0.034 2%,0.021 9% and 0.058 9%;among them,the contents of these five components decreased by 6.04%,72.84%,5.52%,3.10% and 39.65%,respectively. Conclusion:The contents of these five components in Descurainiae Semen is reduced to varying degrees after processing.The contents of phenylpropanoids decrease significantly,while the contents of flavonoid glycosides do not change significantly.
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Objective: To optimize the HPLC characteristic spectrum of flavonoid glycosides of Dendrobium officinale,and identify the common and specific components of different provenances. Method: Kromasil 100-5 C18 column was adopted, with tetrahydrofuran-acetonitrile-methanol (10:22:5)-0.05% phosphoric acid as mobile phase (gradient elution). The detection wavelength was 340 nm,the column temperature was 30℃,and the flow rate was 1.0 mL ·min-1. Result: 13 flavonoid characteristic peaks were marked in 27 batches of D. officinale,and 7 characteristic peaks of 6 flavonoid C-glycosides (vicenin Ⅱ,vicenin Ⅰ,schaftoside,isoschaftoside,violanthin and isoviolanthin) and one flavonoid O-glycosides (rutin) was identified. 7-11 characteristic peaks were detected in different batches of samples. Among them,vicenin Ⅱ was a relatively stable common peak in different source samples,and the characteristic peaks of rutin,schaftoside and isoschaftoside were quite different. According to the relative abundance of the characteristic peaks,the samples could be divided into three categories. Among them,the first category had 10 batches of samples,which mainly came from Danxia landforms of Guangdong,Jiangxi,Fujian and Zhejiang (Wuyi) Province (which called "Danxia landform species") and characterized by detection of obvious peak of rutin. The second category had 11 batches of samples,which mainly came from Yunnan and Guangxi Province (which included "Yunnan Guangnan species" and "Guangxi Tiepilan species") and characterized by detection of violanthin and isoviolanthin. And the third category had 6 batches of samples, which were mainly derived from Zhejiang Province (which called "native species from Zhejiang") and characterized by detection of different degrees of rutin peak, but it was difficult to detect the characteristic peaks of violanthin and isoviolanthin. HPLC characteristic chromatograms of D. officinale in bionics wild cultivation and greenhouse of "Danxia landform species" and "Guangxi Tiepilan species" were compared. The results showed that the characteristic peaks in D. officinale planted in greenhouse could be detected stably,which verified the reliability of the source in D. officinale. Conclusion: The analytical method has a better separation effect on flavonoids of D. officinale, with a good reproducibility. The commonness and specificities of flavonoid glycosides components of D. officinale from different categories have basically confirmed. This suggests that Vicenin Ⅱ is suitable to be a reference peak for characteristic chromatogram. Both the relative abundance of rutin and the detection or relative abundance of violanthin and isoviolanthin peaks could be used as a reference to judge the categories of D. officinale in "Danxia landform species" or "Tiepilan species from Yunnan, South Guangdong and Guangxi" or "native species from Zhejiang".
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Two new flavonoid glycosides, named viscumneoside XII (1), and viscumneoside XIII (2); a new dihydrogen flavonoid glycoside product named viscumneoside XIV (3), were isolated from the aerial part of Viscum album, along with seven known compounds (4-10). Their structures were identified by analysis of spectroscopic data. In addition, cytotoxicity assay showed that 1, 2 and 3 possessed significant inhibitory activities against C6, A549 and MDA-MB-231 (the inhibition rate arrived about 50%, 70% and 74% respectively with IC ≤ 60.00 μmol·L), while the inhibition of TF-1 and Hela was not significant.
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Objective: To isolate and identify the polyphenolic constituents of Dypsis lutescens, and evaluate the hepatoprotective activity of the ethanolic extract of Dypsis lutescens leaves. Methods: Hepatoprotective, antioxidant and anti-inflammatory effects of two doses of Dypsis lutescens ethanolic leaf extract were investigated in five groups of six rats each administered with the ethanolic extract of Dypsis lutescens leaves. Liver function parameters were assessed, histopathological study was carried out, the anti-inflammatory mediators and the antioxidant potential in the liver tissues were evaluated. In addition, the total ethanolic extract of Dypsis lutescens leaves was subjected to different chromatographic separation techniques to yield ten phenolic compounds. The isolated compounds structures were spectroscopically elucidated. Results: Hepatoprotective activity of Dypsis lutescens ethanolic extract was estimated for the first time and showed significant activity against histopathological changes induced by D-galactosamine in liver. The extract improved the liver functions. Compared to the D-galactosamine group, the architecture of the liver in the treated groups was improved in the histopathological examination. These results proved the hepatoprotective activity of Dypsis lutescens and its ability in attenuating liver oxidative damage and inflammation. Phytochemical investigations of the total extract afforded ten compounds from the genus Dypsis. Conclusions: The alcoholic extract of Dypsis lutescens exerted potential hepatoprotective action, maintaining liver health and functions.
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Objective: To isolate and identify the polyphenolic constituents of Dypsis lutescens, and evaluate the hepatoprotective activity of the ethanolic extract of Dypsis lutescens leaves. Methods: Hepatoprotective, antioxidant and anti-inflammatory effects of two doses of Dypsis lutescens ethanolic leaf extract were investigated in five groups of six rats each administered with the ethanolic extract of Dypsis lutescens leaves. Liver function parameters were assessed, histopathological study was carried out, the anti-inflammatory mediators and the antioxidant potential in the liver tissues were evaluated. In addition, the total ethanolic extract of Dypsis lutescens leaves was subjected to different chromatographic separation techniques to yield ten phenolic compounds. The isolated compounds structures were spectroscopically elucidated. Results: Hepatoprotective activity of Dypsis lutescens ethanolic extract was estimated for the first time and showed significant activity against histopathological changes induced by D-galactosamine in liver. The extract improved the liver functions. Compared to the D-galactosamine group, the architecture of the liver in the treated groups was improved in the histopathological examination. These results proved the hepatoprotective activity of Dypsis lutescens and its ability in attenuating liver oxidative damage and inflammation. Phytochemical investigations of the total extract afforded ten compounds from the genus Dypsis. Conclusions: The alcoholic extract of Dypsis lutescens exerted potential hepatoprotective action, maintaining liver health and functions.
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ABSTRACT Phytochemical investigation of the methanol extract of the aerial parts of Peucedanum chryseum (Boiss. & Heldr.) D.F.Chamb., Apiaceae, led to the isolation of a dihydrofuranochromone, cimifugin (1); a phloroacetophenone glucoside, myrciaphenone A (2); and a flavonoid glycoside, afzelin (3) along with two phenylacylated-flavonoid glycosides: rugosaflavonoid C (4), and isoquercitrin 6"-O-p-hydroxybenzoate (5). The structures of compounds 1-5 were elucidated by extensive 1D- and 2D-NMR spectroscopic analysis in combination with MS experiments and comparison with the relevant literature. All compounds are reported for the first time from this species and compounds 2, 4, and 5 from the genus Peucedanum and from Apiaceae.
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Objective: Based on the tumor-bearing rat model, using rutin, quercitrin, and isoquercitrin from Hedyotis diffusa as the research object, the pharmacokinetics of those three flavonoid glycosides in the pathological state was studied. Methods: Establishing a method for the comparison of the pharmacokinetics of flavonoid extracts in normal rats and tumor-bearing rats, which was analyzed by HPLC-MS/MS in subcutaneous tumor models of SD rat made with tumour cell of Walker-256. Results: Compared with the pharmacokinetics parameters of flavonoid glycosides in normal rats, the Cmax and AUC0-∞ of rutin, quercetin, and isoquercitrin in the tumor-bearing rats were significantly decreased, t1/2z was prolonged, and the metabolic time of three components was prolonged to 24 h, which revealed the effect of pathological condition on the pharmacokinetic characteristics of flavonoid glycosides. Conclusion: The method established in this study is simple, fast, sensitive, and suitable for the pharmacokinetic study of flavonoid glycosides in rats in vivo. The pharmacokinetic characteristics of flavonoids in normal and tumor-bearing rats are different.
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Objective To investigate the hydrophilic chemical constituents from Thesium Chinensis Turcz.Methods The water extract of Thesium Chinensis Turcz.was adsorbed onto AB-8 resin column and eluted with 50% ethanol to give the hydrophilic portion TT50.TT50 was further separated and purified by repeated column chromatography on silica gel,Sephadex LH-20.The structures of these purified compounds were identified by NMR spectral analysis and comparison with the reported data.Results Six compounds were isolated and identified as kaempferol(1),kaempferol-3-O-glucoside(2),kaepmferol-3,7-di-O-β-D-glucopyranoside(3),kaempferol-3-O-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranoside(4),kaemperol-3-O-α-L-rham-nopyranosyl(1→2)-[6-O-acetyl]-β-D-glucopyranoside(5),rutinoside(6).Conclusion The main constituents of TT50 were kaempferol glycosides.Compounds 4 and 5 were isolated from this plant for the first time.
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Two new flavonoid glycosides, quercetin-3--(4--crotonyl)--D-glucopyranoside (1) and quercetin-3--[6--(2)-pentenoyl]--D-glucopyranoside (2), along with nine known ones, isoquercetin (3), astragalin (4), quercetin-3--(6--acetyl)--D-glucopyranoside (5), kaempferol-3--(6--acetyl)--D-glucopyranoside (6), quercetin-3--(6--crotonyl)--D-glucopyranoside (7), kaempferol-3--(6--crotonyl)--D-glucopyranoside (8), vitexin (9), isovitexin (10), and isorhamnetin-3---D-glucopyranoside (11), were isolated from the leaves of Moringa oleifera by various chromatographic technologies. Their structures were elucidated by spectroscopic methods including UV, IR, MS, and NMR. In addition, compounds 7 and 8 were isolated from this plant for the first time.
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Components that systematic separated from the root of Anaycclus pyrethrum were identified, in order to lay a foundation for future study of the root of A. pyrethrum. The CCK-8 assay showed that dichloromethane fraction exhibited the highest degree of cytotoxicity than others. Ten monomeric components were obtained from dichloromethane fraction and ethyl acetate fraction extracted from the root of A. pyrethrum, including 7 N-alkylamides, one coumarin and two flavonoid glycosides. They were identified as tetradeca-2E,4E,8E-trienoic acid 4-hydroxyphenylethylamide(1), deca-2E,4E-dienoicacid isobutylamide(2), undeca-2E,4E-diene-8,10-diynoic acid phenylethylamide(3), tetradeca-2E,4E-dienoic acid 4-hydroxyphenylethylamide(4), tetradeca-2E,4E-diene-8,10-diynoic acid isobutylamide(5), deca-2E,4E- dienoic acid 4-hydroxyphenylethylamide(6), dodeca-2E,4E-dienoic acid 4-hydroxy -phenyl-ethylamide(7), isoscopoletin(8), quercetin-7-O-β-D-glucopyranoside(9), isorhamnetin-7-O-β-D-glucopyranoside(10). Among them, compound 1 was identified as a new compound, Compounds 2-4, 8-10 were isolated from this herb for the first time.
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Four new phenolic glycosides, including two flavonoid glycosides (and) and two lignan glycosides (and), were isolated from the traditional Chinese medicine formula, Baoyuan decoction. Their structures were established by detailed analysis of the NMR and HR-ESI-MS spectroscopic data and their absolute configurations were determined by the experimental electronic circular dichroism data as well as chemical methods. Furthermore, the sources of the four new compounds were determined by the UPLC-Qtrap-MS method, which proved thatandare originated from, andandare from.
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Four prenylated flavonoids compounds 1-4, named sinopodophyllines A-D, and a flavonoid glycoside (compound 13), sinopodophylliside A, together with 19 known compounds (compounds 5-12 and 14-24) were isolated from the fruits of Sinopodophyllum hexandrum. The structures of new compounds were elucidated by extensive spectroscopic analysis, including HRESIMS, 1D and 2D NMR. Compounds 1-6, 9-11, and 14-17 were tested for their cytotoxicity against human breast-cancer T47D, MCF-7 and MDA-MB-231 cells in vitro, and compounds 2, 5, 6, 10 and 11 showed significant cytotoxicity (IC values < 10 μmol·L) against T47D cells.
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Humans , Antineoplastic Agents, Phytogenic , Chemistry , Pharmacology , Berberidaceae , Chemistry , Breast Neoplasms , Drug Therapy , Cell Line, Tumor , Cell Proliferation , Flavonoids , Chemistry , Pharmacology , Fruit , Chemistry , Molecular StructureABSTRACT
Objective To compare the changes of four flavonoid glycosides in the leaves of Hippophae rhamnoides L . before and after fermentation .Methods The water extract of Hippophae rhamnoides L .leaves and its fermented tea were con-centrated and desiccated .The dry extracts were dissolved in 70％ ethanol .The chromatographic separation was performed with RP-HPLC method on an Extend-C18 column (4 .6 mm × 250 mm ,5 μm) .Acetonitrile-0 .1％ formic acid was selected as mobile phase at the flow rate of 1 .0 ml/min .The detection wavelength was 356 nm and the column temperature was 30 ℃ .Results The rutin content was high in the leaves of Hippophae rhamnoides L .After fermentation ,isoquercitrin content was increased , while the contents of rutin and narcissoside were reduced and isorhamnetin-3-O-glucoside stayed unchanged .There was a good linear relationship between the concentration and peak areas of the four compounds (r>0 .9997) .The average recoveries were between 96％-103％ .Conclusion This established method is rapid and reliable ,which can be used for the quality control of Hippophae rhamnoides L .leaves and its fermented tea .
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To study Ginkgo biloba leaves in different producing area, we establish an HPLC method for the simultaneously determination of seven flavonoids glycosides and four biflavonoids in G. biloba leaves. The analysis was performed on an Agilent ZORBAX SB-C₁₈ column(4.6 mm×250 mm, 5 μm) wich acetonitrile, and 0.4% phosphoric acid as mobile phase at flow rate of 1 mL•min⁻¹ in a gradient edution, and the detection was carried out at 254 nm.The calibration curves of the seven flavonoids glycosides and four biflavonoids had a good linearitiy with good recoveries. The established HPLC method is simple, rapid, accurate, reliable, and sensitive, and can be applied to the identification and quality control of G. biloba leaves.