OBJECTIVETo study the alkaloids of Macleaya cordata and their anti-tumor activities.

METHODAlcohol and liquid-liquid extraction were used methods were used to extract the alkaloids constituents, and silica gel, reverse-phase octadecylsilyl (ODS), sephadex LH-20 chromatographic methods and HPLC were applied to isolate and purify compounds. MS, NMR spectroscopic methods were used to determine their structures. Furthermore, the cytotoxicity of these chemical components for MCF-7 and SF-268 cell lines was measured by MTT method.

RESULTTwelve alkaloids were isolated from the fruits of M. cordata, and their structures were identified as: maclekarpine E (1), 6-acetonyldihyrochelerythrine (2), cavidilinine (3), 6-acetonyldihyrosanguinnarine (4), O-methylzanthoxyline (5), 6-methoxy-dihydrosanguinarine (6), spallidamine (7), 6-hydroxyldihydrochelerythrine (8), arnotianamida (9), dihydrosanguinarine (10), protopine (11), and cryptopine (12).

CONCLUSIONCompounds 1, 3, 7-9 were isolated from M. cordata for the first time, and compound 5 is a new natural product. The results of cytotoxic assay indicated that compound 6 showed strong cytotoxicity against MCF-7 and SF-268 cell lines with IC50 values of 0.61 μmol · L(-1) and 0.54 μmol · L(-1), respectively.

Alkaloids ; isolation & purification ; pharmacology ; Antineoplastic Agents, Phytogenic ; isolation & purification ; Cell Line, Tumor ; Humans ; Papaveraceae ; chemistry

The study is aimed to ensure the quality and safety of medicinal plants by using ITS2 DNA barcode technology to identify Corydalis boweri, Meconopsis horridula and their close related species. The DNA of 13 herb samples including C. boweri and M. horridula from Lhasa of Tibet was extracted, ITS PCR were amplified and sequenced. Both assembled and web downloaded 71 ITS2 sequences were removed of 5. 8S and 28S. Multiple sequence alignment was completed and the intraspecific and interspecific genetic distances were calculated by MEGA 5.0, while the neighbor-joining phylogenetic trees were constructed. We also predicted the ITS2 secondary structure of C. boweri, M. horridula and their close related species. The results showed that ITS2 as DNA barcode was able to identify C. boweri, M. horridula as well as well as their close related species effectively. The established based on ITS2 barcode method provides the regular and safe detection technology for identification of C. boweri, M. horridula and their close related species, adulterants and counterfeits, in order to ensure their quality control, safe medication, reasonable development and utilization.
Base Sequence ; China ; Corydalis ; chemistry ; classification ; genetics ; DNA Barcoding, Taxonomic ; methods ; DNA, Plant ; chemistry ; genetics ; DNA, Ribosomal Spacer ; chemistry ; genetics ; Molecular Sequence Data ; Nucleic Acid Conformation ; Papaveraceae ; chemistry ; classification ; genetics ; Phylogeny ; Plants, Medicinal ; chemistry ; classification ; genetics

Ongoing study on the chemical constituents of the roots of Macleaya microcarpa led to the isolation of eight compounds of derivatives of triterpenes and organic acids in addition to some previously identified benzophenanthridines. The eight compounds were identified by spectroscopic methods as well as comparison with literature values as 1-oxo-2, 22 (30)-hopandien-29-oic acid (1), 3-oxo-12-oleanen-30-oic acid (2), 3α-hydroxy-12-oleanen-30-oic acid (3), 3β-hydroxy-12-oleanen-30-oic acid (4), ferulic acid (5), ferulic acid 4-O-β-D-glucoside (6), 3-O-feruloylquinic acid (7), and methyl 3-O-feruloylquinate (8). Of which, 1 is a new triterpenoid of hopanes and 2-8 are isolated from M microcarpa for the first time. In order to discover natural active compounds as potential agents of anti-ulcerative colitis (UC), an in vitro drug high-throughput screening model targeted x-box-binding protein 1 (xbp1) was employed to evaluate the activity of the major chemical constituents of M microcarpa. The result confirmed that two dihydrobenzophenanthridines, dihydrosanguinarine (9) and dihydrochelerythrine (10), showed a certain activity on activating the transcription of xbpl, a transcription factor (TF) associated with the occurrence, development, and potential treatment of UC, with their relative activating ratios being 1.76 and 1.77 times, respectively, as compared with control group.
Anti-Ulcer Agents ; chemistry ; Benzophenanthridines ; chemistry ; DNA-Binding Proteins ; genetics ; Isoquinolines ; chemistry ; Papaveraceae ; chemistry ; Plant Roots ; chemistry ; Regulatory Factor X Transcription Factors ; Transcription Factors ; genetics ; Transcription, Genetic ; Triterpenes ; chemistry

Corydalis Rhizoma, the dried tuber of Corydalis yanhusuo (Papaveraceae) distributed traditionally mainly in south-eastern and now cultivated in northwestern and other district in China, is one of the commonly used and well-known traditional Chinese medicine. It has been widely used to treat spastic pain, abdominal pain, pain due to injury, and promote blood circulation. Its main chemical constituents were alkaloids, which were divided into the two types of protoberberines and aporphines. Among them, some alkaloids were found to elicit profound effects on the dopaminergic system in the central nervous system, which plays an important role in regulating nociception. In this article, the chemical composition and structure-types, new methods of qualitative and quantitative analysis as well as characteristics of biotransformation, absorption, distribution, metabolism, excretion, pharmacokinetic, and drug-drug interaction for the alkaloids were revealed. These results would greatly contribute to the establishment of bioactive material base of Corydalis Rhizoma.
Alkaloids ; chemistry ; Animals ; Corydalis ; chemistry ; Drug Interactions ; Drugs, Chinese Herbal ; chemistry ; metabolism ; pharmacokinetics ; Humans ; Medicine, Chinese Traditional ; methods ; Papaveraceae ; chemistry ; Rats ; Rhizome ; chemistry

A phytochemical investigation on the aerial parts of a Tibetan medicine Meconopsis horridula, by solvent extraction, repeated chromatographies on silica gel, Sephadex LH-20, and preparative TLC techniques, led to the isolation of 9 compounds. By spectroscopic analysis and comparison of its 1H and 13C-NMR data with those in literatures, their structures were identified as oleracein E(1), N-( trans-p-coumaroyl) tyramine (2), chrysoeriol (3), apigenin (4), hydnocarpin (5), p-coumaric acid glucosyl ester (6), stigmast-5-ene-3beta-ylformate (7), 3beta-hydroxy-7alpha-ethoxy-24beta-ethylcholest-5-ene (8), and beta-sitosterol (9), respectively, among which compounds 6-8 were isolated from the genus for the first time,and 1,3 were isolated from the species for the first time. A MTT method was applied to evaluate the cytotoxic activity of compounds 14 against the human hepatocellular liver carcinoma cell line (HepG2), and compound 1 showed significant cytotoxicity against HepG2,with its inhibitory rate of 52.2% at 10 micromol x L(-1).
Medicine, Tibetan Traditional ; Molecular Structure ; Papaveraceae ; chemistry ; Plant Extracts ; chemistry ; Spectrometry, Mass, Electrospray Ionization

OBJECTIVETo study the chemical components of essential oils from Meconopsis oliverana and their antioxidant activity.

METHODThe essential oil was extracted by steam distillation, and GC-MS analysis was used to identify its constituents. The OH free radical scavenging activity of the essential oils was evaluated with an enzyme mark instrument by assay of the ability of DPPH free radical scavenging. BHT was used as positive control.

RESULTForty-seven compounds, account for 91.866% of the essential oils, were identified. The ability of scavenging OH and DPPH radicals of the essential oils is stronger than that of BHT.

CONCLUSIONThe main chemical constituents of the essential oils from M. oliverana are n-hexadecanoic acid (27.653%) and 6,10,14-trimethyl-2-pentadecanone (16.330%). And the essential oils showed strong antioxidant activity.

Antioxidants ; chemistry ; metabolism ; Biphenyl Compounds ; metabolism ; Butylated Hydroxytoluene ; metabolism ; China ; Fatty Alcohols ; chemistry ; isolation & purification ; Free Radical Scavengers ; chemistry ; metabolism ; Gas Chromatography-Mass Spectrometry ; Hydroxyl Radical ; metabolism ; Oils, Volatile ; chemistry ; isolation & purification ; Oxidation-Reduction ; Palmitic Acid ; chemistry ; isolation & purification ; Papaveraceae ; chemistry ; Picrates ; metabolism ; Plant Oils ; chemistry ; isolation & purification

OBJECTIVETo search for natural benzylisoquinoline alkaloids against tumor.

METHODIn this study, taken DNA as target, a method was developed for screening of natural benzylisoquinoline alkaloids against tumor from traditional Chinese medicine by the use of centrifugal ultrafiltration combined with HPLC technology. The anti-tumor activity for the compounds screened was evaluated in vitro.

RESULTNine compounds interacted with DNA were discovered and identified from Macleaya cordata, Chelidonium majus, Coptis chinensis, and the proliferation of four types of human solid cancer cell lines was markedly inhibited by these compounds.

CONCLUSIONThe developed method was considered to be suitable for screening of natural benzylisoquinoline alkaloids against tumor from traditional Chinese medicine.

Alkaloids ; analysis ; isolation & purification ; pharmacology ; Antineoplastic Agents, Phytogenic ; pharmacology ; Benzylisoquinolines ; analysis ; isolation & purification ; pharmacology ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Chelidonium ; chemistry ; Coptis ; chemistry ; Drug Evaluation, Preclinical ; Drugs, Chinese Herbal ; analysis ; isolation & purification ; pharmacology ; Humans ; Neoplasms ; drug therapy ; physiopathology ; Papaveraceae ; chemistry

OBJECTIVETo develop an HPLC method for the determination of a Tibetan medicine Meconopsis quintuplinervia.

METHODA Hypersil-Keystone-C18 column (4.6 mm x 250 mm, 5 microm) was used with the isocratic elution of acetonitrile and 0.012% glacial acetic acid. The flow rate was 1.0 mL x min(-1), and the detection wavelength was set at 237 nm.

RESULTThe linear range of 0-methylflavinantine was 0.2-2.4 microg (r = 0.999 7). The average recovery was 96.26%.

CONCLUSIONThe developed method was reliable, and can be used for the quality control of M. quintuplinervia Regel.

Chromatography, High Pressure Liquid ; Drugs, Chinese Herbal ; analysis ; chemistry ; Morphinans ; analysis ; Papaveraceae ; chemistry

Transforming technology for semi-synthesized isocorydione from the natural product ofisocorydine was studied. The factors affecting on the reaction yield were investigated. UV spectrophotometry was used to indicate the semi-synthesized yield of isocorydione. The optimum reaction conditions were determined as following: reacting for 12 h in the solution of sodium dihydrogen phosphate at pH 10, the temperature was 25 degrees C and the ratio of isocorydine to Fremy's radical was 1 : 2. Under the optimum conditions, the yield could reach up to 50.0%. The molecular structure of isocorydione was elucidated by X-ray single-crystal diffraction analysis for the first time.
Antineoplastic Agents, Phytogenic ; chemical synthesis ; chemistry ; isolation & purification ; Aporphines ; chemical synthesis ; chemistry ; isolation & purification ; Crystallography, X-Ray ; Hydrogen-Ion Concentration ; Molecular Structure ; Nitroso Compounds ; Oxidation-Reduction ; Papaveraceae ; chemistry ; Plants, Medicinal ; chemistry ; Spectrophotometry, Ultraviolet ; Temperature ; X-Ray Diffraction

OBJECTIVETo study the alkaloids of Macleaya cordata.

METHODThe alkaloids were isolated and purified by various column chromatography as well as recrystallization. Their structures were identified by physico-chemical properties and spectral analysis.

RESULTThirteen alkaloids were isolated and identified as 6-methoxy-dihydrosanguinarine (1), norsanguinarine (2), 6-acetonyl-dihyrochelerythrine (3), 6-acetonyl-dihyrosanguinnarine (4), sanguidimerine (5), chelidimerine (6), (+/-) -bocconarborine A (7), (+/-)-bocconarborine B (8), cryptopine (9), dihydrosanguinarine (10), dihydrochelerythrine (11), protopine (12), alpha-allocryptopine (13).

CONCLUSIONCompounds 2, 3, 5 - 9 were firstly isolated from the genus Macleaya and compound 1 was obtained from M. cordata for the first time.

Alkaloids ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Papaveraceae ; chemistry