1.Isolation and identification of flavonoids from Spatholobi Caulis.
Xiao-Yan LIU ; Wei XU ; Xiu-Wei YANG ; Peng ZHANG ; Wei ZHAO ; Yun GONG ; Ni-Fu LIU
China Journal of Chinese Materia Medica 2020;45(6):1384-1392
		                        		
		                        			
		                        			The chemical compounds in water extract of Spatholobi Caulis were further studied. The compounds were systematically isolated and purified by using various separation and analysis techniques including silica gel, macroporous adsorptive resins and Sephadex LH-20 column chromatographies, as well as reversed phase high-performance liquid chromatography(RP-HPLC). Twenty-three flavonoids and one chromone were identified by the spectroscopic analysis techniques combining their physicochemical properties, they were identified as isoduartin(1), sativan(2), 8-O-methylretusin(3), 7-hydroxydihydroflavone(4), odoratin(5), butesuperin A(6), biochanin A(7), 3'-methoxydaidzein(8), 7-hydroxychromone(9), calycosin(10), naringenin(11), dihydrocajanin(12),(6 aR,11 aR)-maackiain(13), 2'-hydroxygenistein(14),(6 aR,11 aR)-medicarpin-3-O-glucopyranoside(15),(-)-epiafzelechin(16),(-)-catechin(17),(-)-epicatechin(18), 4',8-dimethoxy-7-O-β-D-glucopyranosylisoflavone(19), ononin(20),(-)-gallocatechin(21), rutin(22), daidzin(23) and sphaerobioside(24). Compounds 4, 6, 8, 9, 11, 12, 14-16, 19 and 22-24 were isolated from Spatholobi Caulis for the first time.
		                        		
		                        		
		                        		
		                        			Chromatography, High Pressure Liquid
		                        			;
		                        		
		                        			Drugs, Chinese Herbal/chemistry*
		                        			;
		                        		
		                        			Fabaceae/chemistry*
		                        			;
		                        		
		                        			Flavonoids/isolation & purification*
		                        			;
		                        		
		                        			Phytochemicals/isolation & purification*
		                        			
		                        		
		                        	
2.Flavonoids with PTP1B inhibition from Broussonetia papyrifera.
Yang LOU ; Shi-Yun SU ; Ya-Nan LI ; Chun LEI ; Jing-Ya LI ; Ai-Jun HOU
China Journal of Chinese Materia Medica 2019;44(1):88-94
		                        		
		                        			
		                        			Eleven flavonoids were isolated from the twigs of Broussonetia papyrifera by column chromatography over silica gel,ODS,MCI gel,and Sephadex LH-20,as well as RP-HPLC.Their structures were identified by spectroscopic methods including NMR,MS,UV,and IR as broupapyrin A(1),5,7,3',4'-tetrahydroxy-3-methoxy-8-geranylflavone(2),8-prenylquercetin-3-methyl ether(3),broussonol D(4),broussoflavonol B(5),uralenol(6),broussonol E(7),8-(1,1-dimethylallyl)-5'-(3-methylbut-2-enyl)-3',4',5,7-tetrahydroxyflanvonol(8),broussoflavonol E(9),4,2',4'-trihydroxychalcone(10),and butein(11).Compound 1 is a new isoprenylated flavonol.Compounds 3,6,10,and 11 were obtained from the genus Broussonetia for the first time,and 4 and 7 were firstly discovered in B.papyrifera.Compounds 1-5 and 7-9 showed significant inhibitory effects on PTP1 B with IC50 values ranging from(0.83±0.30) to(4.66±0.83) μmol·L-1.
		                        		
		                        		
		                        		
		                        			Broussonetia
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Chromatography, High Pressure Liquid
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Magnetic Resonance Spectroscopy
		                        			;
		                        		
		                        			Phytochemicals
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Protein Tyrosine Phosphatase, Non-Receptor Type 1
		                        			;
		                        		
		                        			antagonists & inhibitors
		                        			
		                        		
		                        	
3.A new antioxidant flavonoid glycoside from flowers of Hosta plantaginea.
Qing-Guang ZHOU ; Li YANG ; Jun-Wei HE ; Guo-Yue ZHONG
China Journal of Chinese Materia Medica 2019;44(15):3312-3315
		                        		
		                        			
		                        			Phytochemical investigation of the flowers of Hosta plantaginea led to isolate of one new flavonoid glycoside,plantanone C( 1) by silica gel,Sephadex LH-20,and RP-HPLC column chromatographies. Its structure was extensively determined on basis of HR-ESI-MS and NMR spectroscopic data. Compound 1 exhibited moderate antioxidant activity against DPPH radical scavenging activity,with an IC50 value of 240. 2 μmol·L~(-1).
		                        		
		                        		
		                        		
		                        			Antioxidants
		                        			;
		                        		
		                        			analysis
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			analysis
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Flowers
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Glycosides
		                        			;
		                        		
		                        			analysis
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Hosta
		                        			;
		                        		
		                        			chemistry
		                        			
		                        		
		                        	
4.New flavonoids and methylchromone isolated from the aerial parts of Baeckea frutescens and their inhibitory activities against cyclooxygenases-1 and -2.
Jun-Neng ZHOU ; Ming YAN ; Peng GAO ; Ji-Qin HOU ; Thi-Anh PHAM ; Hao WANG
Chinese Journal of Natural Medicines (English Ed.) 2018;16(8):615-620
		                        		
		                        			
		                        			In the present study, we carried out a phytochemical investigation of the ethanol extract of the aerial parts of Baeckea frutescens, which resulted in the isolation of two new flavonoid glycosides, myricetin 3-O-(5″-O-galloyl)-α-L-arabinofuranoside (1), 6-methylquercetin 7-O-β-D-glucopyranoside (2), one new methylchromone glycoside, 7-O-(4', 6'-digalloyl)-β-D-glucopyranosyl-5-hydroxy-2-methylchromone (3), together with three known compounds (4-6). The structures of these isolated compounds were established on the basis of 1D and 2D NMR techniques and chemical methods. The anti-inflammatory activities of the compounds 1-6 were evaluated for their inhibitory effects against cyclooxygenases-1 and -2 in vitro. Compounds 1-6 showed potent COX-1 and COX-2 inhibiting activities in vitro with IC values ranging from 1.95 to 5.54 μmol·L and ranging from 1.01 to 2.27 μmol·L, respectively.
		                        		
		                        		
		                        		
		                        			Anti-Inflammatory Agents
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Cyclooxygenase 1
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Cyclooxygenase 2
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Cyclooxygenase Inhibitors
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Molecular Structure
		                        			;
		                        		
		                        			Myrtaceae
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Plant Components, Aerial
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Plant Extracts
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			
		                        		
		                        	
5.Chemical constituents from Gnaphalium affine and their xanthine oxidase inhibitory activity.
Wei ZHANG ; Chun-Zhen WU ; Si-Yang FAN
Chinese Journal of Natural Medicines (English Ed.) 2018;16(5):347-353
		                        		
		                        			
		                        			Gnaphalium affine D. Don, a medicinal and edible plant, has been used to treat gout in traditional Chinese medicine and popularly consumed in China for a long time. A detailed phytochemical investigation on the aerial part of G. affine led to the isolation of two new esters of caffeoylquinic acid named (-) ethyl 1, 4-di-O-caffeoylquinate (1) and (-) methyl 1, 4-di-O-caffeoylquinate (2), together with 35 known compounds (3-37). Their structures were elucidated by spectroscopic data and first-order multiplet analysis. All the isolated compounds were tested for their xanthine oxidase inhibitory activity with an in vitro enzyme inhibitory screening assay. Among the tested compounds, 1 (IC 11.94 μmol·L) and 2 (IC 15.04 μmol·L) showed a good inhibitory activity. The current results supported the medical use of the plant.
		                        		
		                        		
		                        		
		                        			Adenine
		                        			;
		                        		
		                        			analogs & derivatives
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Drugs, Chinese Herbal
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Enzyme Activation
		                        			;
		                        		
		                        			drug effects
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Gnaphalium
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Gout Suppressants
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Hydroxybenzoates
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Molecular Structure
		                        			;
		                        		
		                        			Nuclear Magnetic Resonance, Biomolecular
		                        			;
		                        		
		                        			Phytochemicals
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Plant Components, Aerial
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Plant Extracts
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Quinic Acid
		                        			;
		                        		
		                        			analogs & derivatives
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Xanthine Oxidase
		                        			;
		                        		
		                        			antagonists & inhibitors
		                        			
		                        		
		                        	
6.Qualitative characterization of flavonoids in Scutellariae Radix by using PREC-IDA-EPI.
Yang WEI ; Shu-Yao WANG ; Si-Yang WU ; Chen KANG ; Ying-Fei LI
China Journal of Chinese Materia Medica 2018;43(2):345-352
		                        		
		                        			
		                        			Flavonoids are the most abundant constituents and induce these the rapeutic effects against inflammation, gastrointestinal infections, cardiovascular diseases, and respiratory. Most of these flavonoids have low content in Scutellarie Radix. It was difficult to detect some minor compounds by using LC-MS method with full scan. Based on the review of flavonoids that had been extracted from Scutellariae Radix, a method with PREC-IDA-EPI technique was developed and applied to Scutellariae Radix by using UPLC-MS/MS. A total of 97 flavonoids were identified, including 29 aglycones and 68 -glycosides. This study laid the foundation for pharmacodynamicss of Scutellariae Radix.It is believed that an individual detection scheme based on the PREC-IDA-EPI technique could be used to identify unknown compounds.
		                        		
		                        		
		                        		
		                        			Chromatography, Liquid
		                        			;
		                        		
		                        			Drugs, Chinese Herbal
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Scutellaria baicalensis
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Tandem Mass Spectrometry
		                        			
		                        		
		                        	
7.Flavonoids isolated from Sinopodophylli Fructus and their bioactivities against human breast cancer cells.
Qing-Hui WANG ; Shuai GUO ; Xue-Yan YANG ; Yi-Fan ZHANG ; Ming-Ying SHANG ; Ying-Hui SHANG ; Jun-Jun XIAO ; Shao-Qing CAI
Chinese Journal of Natural Medicines (English Ed.) 2017;15(3):225-233
		                        		
		                        			
		                        			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.
		                        		
		                        		
		                        		
		                        			Antineoplastic Agents, Phytogenic
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Berberidaceae
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Breast Neoplasms
		                        			;
		                        		
		                        			drug therapy
		                        			;
		                        		
		                        			physiopathology
		                        			;
		                        		
		                        			Cell Line, Tumor
		                        			;
		                        		
		                        			Cell Proliferation
		                        			;
		                        		
		                        			drug effects
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Fruit
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Humans
		                        			;
		                        		
		                        			Molecular Structure
		                        			
		                        		
		                        	
8.Identification of C-geranylated flavonoids from Paulownia catalpifolia Gong Tong fruits by HPLC-DAD-ESI-MS/MS and their anti-aging effects on 2BS cells induced by HO.
Wen-Zhao TANG ; Ying-Ai WANG ; Tian-Yang GAO ; Xiao-Jing WANG ; Yun-Xue ZHAO
Chinese Journal of Natural Medicines (English Ed.) 2017;15(5):384-391
		                        		
		                        			
		                        			The fruits of Paulownia catalpifolia Gong Tong are used as a Chinese folk herbal medicine for the treatment of enteritis, tonsillitis, bronchitis, and dysentery, etc. Our previous study has identified new C-geranylated flavanones with obvious anti-proliferative effects in lung cancer A549 cells. In the present study, a new C-geranylated flavone, paucatalinone C (1) and five known C-geranylated flavanones (2-6) were isolated. In addition, a total of 34 C-geranylated flavonoids were detected by HPLC-DAD-ESI-MS/MS coupling techniques from the CHCl extract of P. catalpifolia. Futhermore, anti-aging effects of isolated compounds were evaluated in vitro with premature senescent 2BS cells induced by HO. Phytochemical results indicated that P. catalpifolia was a natural resource of abundant C-geranylated flavonoids. Diplacone (3) and paucatalinone A (5) were the potent anti-aging agents in the premature senescent 2BS cells induced by HO and the C-geranyl substituent may be an important factor because of its lipophilic character.
		                        		
		                        		
		                        		
		                        			Aging
		                        			;
		                        		
		                        			drug effects
		                        			;
		                        		
		                        			Cell Line
		                        			;
		                        		
		                        			Chromatography, High Pressure Liquid
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Fruit
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Humans
		                        			;
		                        		
		                        			Hydrogen Peroxide
		                        			;
		                        		
		                        			toxicity
		                        			;
		                        		
		                        			Magnoliopsida
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Molecular Structure
		                        			;
		                        		
		                        			Plant Extracts
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Tandem Mass Spectrometry
		                        			
		                        		
		                        	
9.Studies on flavonoids from Derris eriocarpa.
Lun-xing WANG ; Hong-guo WU ; Hua ZHANG ; Hua-yong LOU ; Guang-yi LIANG ; Wen-wen JIANG ; Zai-chang YANG ; Wei-dong PAN
China Journal of Chinese Materia Medica 2015;40(15):3009-3012
		                        		
		                        			
		                        			Derris eriocarpa, a traditional Chinese medicine belonging to the family of Leguminosae, is widely distributed mainly over Yunnan, Guangxi and Guizhou of China. Modern pharmacological researches on this herb showed that it had extensive bioactivities, such as promoting urination, removing dampness and cough and reducing inspissated mucus and other biological activities. The extensive studies on the chemical constituents of this plant have resulted in the isolation of triterpenoids, steroids, fatty acid and others, but the flavone compounds haven't reported before. In our further research on the ethyl acetate of this plant, nine flavone compounds were obtained by column chromatography on silica gel, Sephadex LH-20, semi-prep HPLC, polyamide column chromatography and recrystallization for separation and purification. The structures were determined on the basis of extensive spectroscopic analysis, including MS, NMR experiments and comparison with spectroscopic data in the literature, respectively, as diosmetin (1), 3, 3'-di-O-methylquercetin (2), afromosin (3), 6, 3'-dihydroxy-7, 4'-dimethoxyisoflavone (4), odoratin (5), 7, 3'-dihydroxy-8, 4'-dimethoxyisoflavone (6), 6, 4'-dihydroxy-7, 3'-dimethoxyisoflavone (7), 5, 7, 4'-trihydroxy-3, 3', 5'-trimethoxyflavone (8), and alpinumisoflavone (9). All these compounds were isolated from Derris eriocarpa How for the first time. And the in vitro assays showed that compound 2 possessed moderate inhibitory activity against human cancer cells K562 and HEL.
		                        		
		                        		
		                        		
		                        			Derris
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			pharmacology
		                        			;
		                        		
		                        			Humans
		                        			;
		                        		
		                        			K562 Cells
		                        			
		                        		
		                        	
10.Analysis of four flavonoids in Lysimachia clethroides using ionic liquid-assisted extraction.
Jin-feng WEI ; Zhi-juan ZHANG ; Dong-dong LI ; Wei LIU ; Wen-yi KANG
China Journal of Chinese Materia Medica 2015;40(7):1305-1310
		                        		
		                        			
		                        			In order to established a method for simultaneous determination of isoquercitrin, astragaline, quercetin and kaempferol in Lysimachia clethroides, the ionic liquid 1-hexyl-3-methylimidazolium hexafluorophosphate ([HMIM]PF6) methanol was used as the ultrasound-assisted extraction solvent combing with RP-HPLC. A Purospher star RP-C1 column was used with the mobile phase of aceto- nitrile, methanol and 0. 4% phosphate acid by gradient elution at the detection wavelength of 360 nm. The flow rate was 0.7 mL x min(-1), and the column temperature was the room temperature. Under the optimized conditions, the linear ranges were 2.54 x 10(-2)-2. 54, 2.50 x 10(-2)- 2.50, 1.54 x 10(-3)-0.154, 1.49 x 10(-3)-0.149 microg for isoquercitrin, astragaline, quercetin and kaempferol, respectively. The average recoveries of the four constituents were 101.1%, 98.90%, 101.0%, 101.6%, respectively. The method was green, simple, rapid and accurate, and provided a valid method for analysis of isoquercitrin, astragaline, quercetin and kaempferol in L. clethroides.
		                        		
		                        		
		                        		
		                        			Chemical Fractionation
		                        			;
		                        		
		                        			instrumentation
		                        			;
		                        		
		                        			methods
		                        			;
		                        		
		                        			Chromatography, High Pressure Liquid
		                        			;
		                        		
		                        			Drugs, Chinese Herbal
		                        			;
		                        		
		                        			analysis
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Flavonoids
		                        			;
		                        		
		                        			analysis
		                        			;
		                        		
		                        			isolation & purification
		                        			;
		                        		
		                        			Ionic Liquids
		                        			;
		                        		
		                        			chemistry
		                        			;
		                        		
		                        			Primulaceae
		                        			;
		                        		
		                        			chemistry
		                        			
		                        		
		                        	
            
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