1.Caffeoylquinic acid derivatives from the seeds of Vernonia anthelmintica.
Yongxia WANG ; En WANG ; Jing SHANG ; Hao WANG
China Journal of Chinese Materia Medica 2012;37(11):1590-1592
Mature seeds of Vernonia anthelmintica were separated and purified by using such methods as macroporous absorption resin, Sephadex LH-20 and HPLC preparative chromatography. Six compounds were obtained and their structures were identified by such spectrum techniques as 1H, 13C-NMR and MS. Compound 1-6 were identified as caffeic acid (1), 3-O-caffeoylquinic acid (2), 4-O-caffeoylquinic acid (3), 5-O-caffeoylquinic acid (4), 3, 4-di-O-caffeoylisoquinic acid (5), 3, 4-di-O-caffeoylquinic acid (6). Among them, compounds 1-6 were separated from this plant for the first time, while compounds 3-5 were separated from this genus firstly.
Drugs, Chinese Herbal
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chemistry
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Quinic Acid
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analogs & derivatives
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analysis
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chemistry
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isolation & purification
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Seeds
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chemistry
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Vernonia
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chemistry
2.Chemical constitutents from pre-formulation of lonicerae japonicae flos in shuanghuanglian lyophilized powder for injection.
China Journal of Chinese Materia Medica 2011;36(12):1613-1619
OBJECTIVETo research the chemical constitutents for the pre-formulation of Lonicerae Japonicae Flos (the dried buds of Lonicera japonica) in Shuanghuanglian lyophilized powder for injection and provide substance foundation for the adverse reaction of Shuanghuanglian lyophilized powder for injection.
METHODThe chemical constituents were isolated by column chromatography and preparative HPLC. All structures were characterized by the spectroscopic methods including ESI-MS, 1H-NMR, 13C-NMR, and compared with data in the literature.
RESULTTwenty compounds were isolated and identified as sophoraricoside(1), luteolin-7-O-beta-D-glucopyranoside(2), rutin(3), quercetin(4), 3,5-O-dicaffeoyl quinic acid methyl ester(5), 4,5-O-dicaffeoyl quinic acid methyl ester(6), 3,4-O-dicaffeoyl quinic acid methyl ester(7), 4,5-dicaffeoyl quinic acid(8), 3,4-dicaffeoyl quinic acid(9), chlorogenic acid(10), epi-vogeloside (11), sweroside(12), vogeloside(13), secoxyloganin(14), macranthoidin A(15), macranthoidin B(16), loniceroside A(17), loniceroside B(18), loniceroside C(19), dipsacoside B(20).
CONCLUSIONCompound 1 was identified in genus Lonicera for the first time and compounds 1-20 were isolated from the pre-formulation for the first time.
Chlorogenic Acid ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Flowers ; chemistry ; Freeze Drying ; Lonicera ; chemistry ; Oleanolic Acid ; analogs & derivatives ; chemistry ; Quinic Acid ; analogs & derivatives ; chemistry ; Rutin ; chemistry ; Saponins ; chemistry
3.Caffeoylquinic acid derivatives from leaves of Lonicera japonica.
China Journal of Chinese Materia Medica 2009;34(18):2346-2348
OBJECTIVETo study the caffeoylquinic acid derivatives from the leaves of Lonicera japonica.
METHODThe compounds were isolated by column chromatography and identified on the basis of physico-chemical constants and spectral analysis.
RESULTFive caffeoylquinic acid derivatives were isolated,and their structures were identified as 3,4-di-O-caffeoyl quinic acid methyl ester (1), 5-O-caffeoyl quinic acid methyl ester (2), 3,4-di-O-caffeoyl quinic acid (3), 1,3-di-O-caffeoyl quinic acid (4) and chlorogenic acid (5), respectively.
CONCLUSIONCompounds 2, 4 were obtained from this genus for the first time. Compounds 1, 3 were obtained from this plant for the first time.
Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Lonicera ; chemistry ; Plant Leaves ; chemistry ; Quinic Acid ; analogs & derivatives ; chemistry ; isolation & purification
4.Comparative study on four major active compounds of Sanvitalia procumbens and Chrysanthemum morifolium cv 'Hangju' and 'Gongju'.
Liang WANG ; Tao WANG ; Qiao-Sheng GUO ; Yong HUANG ; Hao-Kun XU
China Journal of Chinese Materia Medica 2013;38(20):3442-3445
The contents of chlorogenic acid, 3,5-O-caffeoylquinic acid, galuteolin and quercitrin in Sanvitalia procumbens and Chrysanthemum morifolium cv. 'Hangju' and 'Gongju' were determined by RP-HPLC. The main active ingredient of S. procumbens was similar to C. morifolium cv. 'Hangju' and 'Gongju'. The content varied significantly. The contents of chlorogenic acid, quercitrin and galuteolin in S. procumbens were 7.46, 46.58, 26.01 mg x g(-1), respectively, and they were the highest among the samples. The content of 3,5-O-caffeoylquinic acid in C. morifolium cv. 'Hangju' was 14.70 mg x g(-1), it was the highest among the samples. The data of the study provide a basis for further research and development of S. procumbens.
Asteraceae
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chemistry
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Chlorogenic Acid
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analogs & derivatives
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analysis
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Chromatography, High Pressure Liquid
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Chrysanthemum
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chemistry
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Drugs, Chinese Herbal
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analysis
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Quinic Acid
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analogs & derivatives
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analysis
5.Quantitative analysis of seven phenolic acids in eight Yinqiao Jiedu serial preparations by quantitative analysis of multi-components with single-marker.
Jun-jun WANG ; Li ZHANG ; Qing GUO ; Jun-ping KOU ; Bo-yang YU ; Dan-hua GU
Acta Pharmaceutica Sinica 2015;50(4):480-485
The study aims to develop a unified method to determine seven phenolic acids (neochlorogenic acid, chlorogenic acid, 4-caffeoylquinic acid, caffeic acid, isochlorogenic acid B, isochlorogenic acid A and isochlorogenic acid C) contained in honeysuckle flower that is the monarch drug of all the eight Yinqiao Jiedu serial preparations using quantitative analysis of multi-components by single-marker (QAMS). Firstly, chlorogenic acid was used as a reference to get the average relative correction factors (RCFs) of the other phenolic acids in ratios to the reference; columns and instruments from different companies were used to validate the durability of the achieved RCFs in different levels of standard solutions; and honeysuckle flower extract was used as the reference substance to fix the positions of chromatographic peaks. Secondly, the contents of seven phenolic acids in eight different Yinqiao Jiedu serial preparations samples were calculated based on the RCFs durability. Finally, the quantitative results were compared between QAMS and the external standard (ES) method. The results have showed that the durability of the achieved RCFs is good (RSD during 0.80% - 2.56%), and there are no differences between the quantitative results of QAMS and ES (the relative average deviation < 0.93%). So it can be successfully used to the quantitative control of honeysuckle flower principally prescribed in Yinqiao Jiedu serial preparations.
Caffeic Acids
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analysis
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Chlorogenic Acid
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analogs & derivatives
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analysis
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Chromatography, High Pressure Liquid
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Drugs, Chinese Herbal
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analysis
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Flowers
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chemistry
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Hydroxybenzoates
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analysis
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Lonicera
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chemistry
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Quinic Acid
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analogs & derivatives
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analysis
6.Studies on chemical constituents in the buds of Tussilago farfara.
Yu-feng LIU ; Xiu-wei YANG ; Bin WU
China Journal of Chinese Materia Medica 2007;32(22):2378-2381
OBJECTIVETo study the chemical constituents in the buds of Tussilago farfara.
METHODThe chemical constituents were isolated by various column chromatographic methods and structurally elucidated by NMR and MS evidences.
RESULTEleven compounds were obtained and identified as methyl 3, 4-O-dicaffeoylquinate (1), methyl 3, 5-O-dicaffeoylquinate (2), methyl 4, 5-O-dicaffeoylquinate (3), 3, 5-O-dicaffeoylquinic acid (4), methyl 3-O-caffeoylquinate (5), 3-O-caffeoylquinic acid (6), hyperoside (7), rutin (8), kaempferol 3-O-beta-D-glucopyranoside (9), quercetin (10), and kaempferol (11).
CONCLUSIONCompounds 2-5 were isolated from the genus for the first time.
Flowers ; chemistry ; Molecular Structure ; Plants, Medicinal ; chemistry ; Quercetin ; analogs & derivatives ; chemistry ; isolation & purification ; Quinic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Rutin ; chemistry ; isolation & purification ; Tussilago ; chemistry
7.HPLC determination of four active components in dengzhanxixin injection.
Xiao-ming WANG ; Yue-fei WANG ; Gui-xiang PAN ; Jing YANG
China Journal of Chinese Materia Medica 2008;33(14):1681-1683
OBJECTIVETo establish a method for determination of chlorogenic acid, caffeic acid, caffeoylquinic acid and ScuteIlarin in Dengzhan Xixin injection.
METHODThe HPLC method was carried out on Agilent Zorbax SB-C18 column (150 mm x 4. 6 mm, 5 pim) evaluated with acetonitrile-0.1% formic acid as mobile phase, gradient elution; the flow rate was 1.0 mL x min(-1); the temperatue of column was at 35 degrees C; the detection wavelength was at 335 nm for UV detection.
RESULTThe calibration curves were linear in the range of 0.025 to 0.800 microg (r = 0.9990) for chlorogenic acid, 0.027 to 0.850 microg (r = 0.9999) for caffeic acid, 0.062 to 1.978 microg (r = 0.9997) for caffeoylquinic acid and 0.118 to 3.770 microg (r = 0.9999) for scutellarin,respectilely. The average recoveries were 97.19% with RSD 1.16%; 100.45% with RSD 1.16%; 97.32% with RSD 1.43% and 103.81% with RSD 0.70%, respectively.
CONCLUSIONThe assay demonstrated that the method was simple, it had adequate accuracy and selectivity to quantify the four active components in Dengzhan Xixin injection.
Apigenin ; chemistry ; Caffeic Acids ; chemistry ; Chlorogenic Acid ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Drugs, Chinese Herbal ; chemistry ; Glucuronates ; chemistry ; Quinic Acid ; analogs & derivatives ; chemistry ; Reproducibility of Results
8.Chemical comparison of different Farfarae Flos by NMR-based metabolomic approaches.
Zheng-zheng ZHANG ; Hai-juan ZHI ; Xue-mei QIN ; Zhen-yu LI
Acta Pharmaceutica Sinica 2015;50(5):599-604
1H NMR-based metabolomic approach combined with multivariate statistical analysis was used to evaluate the quality of 21 Farfarae Flos (FF) samples from different growth regions. Principal component analysis showed that wild and cultivated FF could be separated clearly, suggesting a big chemical difference existed between them. Supervised PLS-DA analysis indicated that the wild samples showed higher levels of secondary metabolites, such as bauer-7-ene-3β, 16α-diol, chlorogenic acid, rutin, 7-(3'-ethylcrotonoyloxy)-1α-(2'-methyl-butyryloxy)-3, 14-dehydro-Z-notonipetranone (EMDNT), tussilagone, β-sitosterol and sitosterone. This is consistent with traditional experience that the quality of wild samples are better than that of cultivated ones. The content of pyrrolizidine alkaloids senkirkine also differed greatly among samples from different habitats. The Pearson correlation analysis showed that senkirkine is positively correlated with 4, 5-O-dicaffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, 3,4-O-dicaffeoylquinic acid, rutin, kampferol analogues, to a statistically significant extent. The correlation between the toxic compounds and the bioactive components in FF should be further studied.
Chlorogenic Acid
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Drugs, Chinese Herbal
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chemistry
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Flowers
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chemistry
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Magnetic Resonance Imaging
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Magnetic Resonance Spectroscopy
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Metabolomics
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Quinic Acid
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analogs & derivatives
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Rutin
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Sitosterols
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Tussilago
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chemistry
9.Simultaneous determination of five organic acids in Kudiezi injection by HPLC.
Rui LIU ; Lu SUN ; Wen ZHAO ; Yu-Bo LI ; Yan-Jun ZHANG
China Journal of Chinese Materia Medica 2013;38(19):3287-3290
The aim was to develop a high performance liquid chromatography method for simultaneous determination of five organic acids in Kudiezi injection. The Diamonsil C18 column (4.6 mm x 200 mm, 5 microm) was adopted with acetonitrile and water as the mobile phase at a gradient mode program. The flow rate was 1.0 mL min-1 , detection wavelength was 325 nm, and column temperature was 35 degree C. The linear range of monocaffeyltartaric acid, chlorogenic acid, caffeic acid, ferulic acid, and chicoric acid were 0. 64-81.60 (r =0. 999 9),0.09-11. 10 (r =0.999 8) ,0.09-11.30 (r =0. 999 8),0.10-12.80 (r =0.999 9),0.43-55. 50 mg L-1 (r = 0.999 8) , respectively. The average recoveries were 101.8% ,100. 9% ,99. 24% ,99. 83% ,101.9%, respectively, with RSD of less than 2.0%. The developed HPLC method was simple, sensitive and accurate with good repeatability. This work provided helpful information for comprehensive quality control of Kudiezi injection. [Key words] Kudiezi injection; organic acids; content determination; HPLC
Caffeic Acids
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analysis
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Chlorogenic Acid
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analysis
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Chromatography, High Pressure Liquid
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methods
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Coumaric Acids
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analysis
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Drugs, Chinese Herbal
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chemistry
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Quinic Acid
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analogs & derivatives
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analysis
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Succinates
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analysis
10.Optimization of processing technology for xanthii fructus by UPLC fingerprint technique and contents of toxicity ingredient.
Yan-Quan HAN ; Yan HONG ; Lun-Zhu XIA ; Jia-Rong GAO ; Yong-Zhong WANG ; Yan-Hua SUN ; Jin-Hai YI
China Journal of Chinese Materia Medica 2014;39(7):1248-1254
The experiment's aim was to optimize the processing technology of Xanthii Fructus which through comparing the difference of UPLC fingerprint and contents of toxicity ingredient in water extract of 16 batches of processed sample. The determination condition of UPLC chromatographic and contents of toxicity ingredient were as follows. UPLC chromatographic: ACQUITY BEH C18 column (2.1 mm x 100 mm, 1.7 microm) eluted with the mobile phases of acetonitrile and 0.1% phosphoric acidwater in gradient mode, the flow rate was 0.25 mL x min(-1) and the detection wavelength was set at 327 nm. Contents of toxicity ingredient: Agilent TC-C18 column (4.6 mm x 250 mm, 5 microm), mobile phase was methanol-0.01 mol x L(-1) sodium dihydrogen phosphate (35: 65), flow rate was 1.0 mL x min(-1), and detection wavelength was 203 nm. The chromatographic fingerprints 16 batches of samples were analyzed in using the similarity evaluation system of chromatographic, fingerprint of traditional Chinese medicine, SPSS16.0 and SIMCA13.0 software, respectively. The similarity degrees of the 16 batches samples were more than 0.97, all the samples were classified into four categories, and the PCA showed that the peak area of chlorogenic acid, 3,5-dicaffeoylquinic acid and caffeic acid were significantly effect index in fingerprint of processed Xanthii Fructus sample. The outcome of determination showed that the toxicity ingredient contents of all samples reduced significantly after processing. This method can be used in optimizing the processing technology of Xanthii Fructus.
Caffeic Acids
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analysis
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toxicity
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Chemistry, Pharmaceutical
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Chromatography, High Pressure Liquid
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methods
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Drugs, Chinese Herbal
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analysis
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toxicity
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Quinic Acid
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analogs & derivatives
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analysis
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toxicity
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Xanthium
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chemistry
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classification