To study the chemical constituents of the inflorescences of Coreopsis tinctoria from Xinjiang, isolation and purification of constituents were carried out by column chromatography on macroporous resin (D101) , MCI gel, MDS gel, silica gel, Sephadex LH-20 and semi-preparative HPLC. The structures of the compounds were identified by physicchemical properties and spectral data analysis. Fourteen compounds were isolated and identified as coretinterpenoid A (1), coretinphenol (2), quercetin (3), quercetin-3-O-β-glucopyranoside (4), luteolin (5), taxifolin (6), 7, 3', 5'-trihydroxyflavanone (7), isookanin (8), isookanin-7-O-β-D-glucopyranoside (9), 5, 7, 3', 5'-tetrahydroxyflavanone-7-O-β-D-glucopyranoside (10), butein (11), okanin (12), sulfuretin (13), and linocinnamarin (14). Compound 1 was a new isabolane-type sesquiterpenoid and compounds 4, 10 and 13 were isolated from this plant for the first time.
Coreopsis ; chemistry ; Sesquiterpenes ; chemistry ; isolation & purification

The rat everted intestinal sac model was adopted to investigate the absorption of total flavonoids from Coreopsis tinctoria in different intestinal segments. Cyaniding-3-O-β-D-glucoside, chlorogenic acid, flavanomarein, quercetagetin-7-O-β-D-glucoside, iso-okanin, marein and 3,5-dicaffeoylquinic acid which as the major chemical components of total flavonoids from C. tinctoria were selec-ted as the study objects to evaluate the absorption characteristics of each component in different intestinal segments. The results showed that the absorption of seven components of total flavonoids at different intestinal segments was in consistent with zero order absorption rate. The K_a of chlorogenic acid, flavanomarein, quercetagetin-7-O-β-D-glucoside, isookanin and 3,5-dicaffeoylquinic acid increased with increasing of concentration of total flavonoids(P<0.05), indicating that the intestinal absorption of these five components was passive transport. The K_a of cyaniding-3-O-β-D-glucoside and marein showed a weak concentration dependence, suggesting that the absorption of them may be an positive and passive co-existing mode. The result of absorption in different intestinal segments showed that cyaniding-3-O-β-D-glucoside, chlorogenic acid, flavanomarein, quercetagetin-7-O-β-D-glucoside, marein and 3,5-dicaffeoylquinic acid were mainly absorbed in ileum, while isookanin was mainly absorbed in jejunum. The total flavonoids of C. tinctoria are selectively absorbed in intestinal tract, the rat everted intestinal sac model can be used to evaluate the multi-component intestinal absorption characteristics of total flavonoids from C. tinctoria.
Animals ; Chlorogenic Acid ; Coreopsis ; Flavonoids ; Intestinal Absorption ; Plant Extracts ; Rats

There are about 100 species in the genus Coreopsis which distributed in the America, south of Africa and Hawaiian Islands, and 7 species are distributed in China. The inflorescences of Coreopsis tinctoria Nutt. is the Uigur herb 'Snow chrysanthemum' which is named 'Shemuju' with the effects of heat-cleaning, detoxicating, dampness-dissipating and dysentery-curing in the Xinhua Herbal Scheme. The chemical constituents from Coreopsis plants mainly contain flavonoids, phenylpropanoids, sesquiterpenes, and sterols, which show anti-inflammatory activities in modern pharmaceutical research. This article presents an overview of the chemical constituents and pharmaceutical activities, prospects of development and exploitation of Coreopsis plants, hopefully to provide a basis for further research and development of Coreopsis plants.
Animals ; Coreopsis ; chemistry ; Drug Discovery ; methods ; Drugs, Chinese Herbal ; chemistry ; pharmacology ; Humans ; Plants, Medicinal ; chemistry

OBJECTIVETo study the chemical constituents of the inflorescences of Coreopsis tinctoria and provide the chemical basis for development and utilization of this plant.

METHODVarious chromatographic techniques were employed for the isolation and purification of the constituents including silica gel, Sephadex LH-20 and pre-HPLC. The structures of compounds were elucidated by chemical and spectral analysis (NMR, IR, UV and MS).

RESULTEight compounds have been isolated from the inflorescences of C. tinctoria, including three organic acids which are 3,4-dihydroxybenzoicacid (1), 4-hydroxybenzoicacid (2) and caffeic acid (3), one organic ester which is 4-O-beta-D-glucopyranosyl-p-coumaric acid methyl ester (4), two flavonones which are 2S-3',5',7-trihydroxyflavanone (5) and (2R,3R)-3,4',5,7-tetrahydroxylflavanone (6), two sterols which are stigmasterol-3-O-beta-D-glucopyranoside (7) and beta-sitosterol (8).

CONCLUSIONCompounds 1-7 were isolated from genus Coreopsis for the first time and compound 8 was isolated first from C. tinctoria.

Chromatography, High Pressure Liquid ; Coreopsis ; chemistry ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; Molecular Structure

The qualitative analysis of flavonoids in Coreopsis tinctoria was carried out by a combination of 2 D-TLC and HPLC-IT-TOF-MS. The separation was conducted on 2 D-TLC and a Phenomenex Kinetex Evo C_(18) column(2.1 mm×100 mm, 2.6 μm) with methanol-0.05% aqueous formic acid by gradient elution. Electrospray ionization-(ESI) source was applied and operated in both positive and negative ionization modes. Eighteen flavonoids including three flavonoids, one flavonol, nine flavonones, one flavanonol and four chalcones, were putatively identified from the flavone-enriched fraction of C. tinctoria. 2 D-TLC could separate the flavonoids from C. tinctoria. HPLC-IT-TOF-MS was able to quickly and accurately analyze the flavonoids in C. tinctoria. The results would provide experimental information for the efficacy material basis clarification of C. tinctoria.
Chalcones ; analysis ; Chromatography, High Pressure Liquid ; Coreopsis ; chemistry ; Flavonoids ; analysis ; Phytochemicals ; analysis ; Plant Extracts ; analysis ; Spectrometry, Mass, Electrospray Ionization

Response surface methodology (RSM) was used to optimizing the ultrasonic-assisted extraction technology of pigment from Coreopsis tinctoria. The results showed that the flavonoids were the main constituents of the pigment Based on single factor experiments, a four-factor-level experiment design were developed by box-benhnhen central composite design method with causal factors of ultrasonic temperature, ultrasonic time, ratio of liquid to raw material, the concentrations of ethanol in solvent and the extract absorbance value for the response. The interactive effects of four crucial technological parameters were assessed by response surface methodology (RSM). The optimum ultrasonic-assisted extraction conditions were as follow: ultrasonic temperature was 70 °C, ultrasonic time was 60 min, the concentrations of ethanol in solvent was 72.25% and the ratio of liquid to raw material was 32.05:1 mL . g-1. Under the optimum extraction technology conditions, the absorbance value was 0. 936. The conditidns are suitable for the extraction process regression analysis and parameter optimization.
Coreopsis ; chemistry ; Ethanol ; Flavonoids ; isolation & purification ; Pigments, Biological ; isolation & purification ; Plant Extracts ; isolation & purification ; Plants, Medicinal ; Regression Analysis ; Solvents ; Temperature ; Time Factors ; Ultrasonics