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

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 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

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

OBJECTIVETo establish a HPLC method for determination of protopine and isocorydine in root of Dactylicapnos scandens.

METHODThe separation was performed in a PHENOMENEX-C18 column with a mobile phase of methanol-0.2% phosphoric acid (adjusted to pH 7.0 with triethylamine)(50:50), The detection wavelength was at 254 nm and the flow rate was 0.8 mL x min(-1).

RESULTThe average recovery of Protopine and Isocorydine was 97.9%, 98.6% respectively, and RSD 1.3%, 1.4%.

CONCLUSIONThis method is accurate, simple and reliable. It can be used for quality control of D. scandens.

Aporphines ; analysis ; Benzophenanthridines ; Berberine Alkaloids ; analysis ; Chromatography, High Pressure Liquid ; Papaveraceae ; chemistry ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Quality Control

OBJECTIVETo study the chemical constituents of a Tibetan medicine Meconopsis quintuplinervia.

METHODColumn chromatographic techniques were applied to isolate constituents. A combination of IR, MS and NMR spectroscopy was used to identify structures of constituents.

RESULTTwelve compounds were isolated from the ethanolic extract and their structures were elucidated as quercetin 3-O-beta-D-glucopyranoside (I), quercetin 3-O-beta-D-galactopyranosyl-(1-->6)-glucopyranoside (II), kaempferol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (III), isorhamnetin 3-0-beta-D-galactopyranosyl-(1-->6)-beta-D-glucopyranoside (IV), caffeic acid (V), protocatechuic acid (VI), p-hydroxycinnamic (VII), 2-(3,4-dihydroxyphenyl )-ethyl-O-beta-D-glucopyranoside (VIII), p-hydroxybenzoyl-beta-D-glucopyranoside (IX), 4-O-beta-D-glucopyranosyl-(Z)-p-coumaric acid (X), 5, 7-dihydroxy-4H-4-chromenone (XI), daucosterol (XII).

CONCLUSIONTen compounds were isolated from this genus for the first time except for XI and XII.

Caffeic Acids ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Hydroxybenzoates ; chemistry ; isolation & purification ; Papaveraceae ; chemistry ; Plants, Medicinal ; chemistry ; Quercetin ; analogs & derivatives ; chemistry ; isolation & purification

AIMTo reinvestigate the chemical constituents of the ethanolic extract of Meconopsis quintuplinervia Regel which is a traditional Tibetan medicine used for treatments of hepatitis, tuberculosis etc..

METHODSThe compounds were enriched by column chromatography techniques over silica gel, macro porous resin and Sephadex LH-20 absorbents, and finally purified by reverse phase preparative HPLC methods with isocratic mobile phase systems of methanol-H2O-acetic acid (500:500:1) and acetonitrile-H2O-acetic acid (200:800:1). Structural determination of the pure compounds were based on extensive analyses of modern spectroscopic methods including IR, MS, HRMS, 1D- and 2D-NMR spectra.

RESULTSThree alkaloids were obtained and their structures were elucidated as norsanguinarine (I), O-methylflavinantine (II) and 6-methoxy-17-methyl-2, 3-[methylenebis (oxy)]-morphin-5-en-7-one (III).

CONCLUSIONNorsanguinarine (I) was isolated from genus Meconopsis for the first time, and 6-methoxy-17-methyl-2,3-[methylenebis(oxy)]-morphin-5-en-7-one (III) is a new alkaloid named as meconoquintupline.

Alkaloids ; chemistry ; isolation & purification ; Medicine, Tibetan Traditional ; Molecular Conformation ; Molecular Structure ; Morphinans ; chemistry ; isolation & purification ; Morphine Derivatives ; chemistry ; isolation & purification ; Papaveraceae ; chemistry ; Plants, Medicinal ; 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

OBJECTIVETo offer evidences for quality control of medicinal plant of Dactylicapnos scandens.

METHODPharmacognostic studies were carried out through field collection, morphological and microscopic characteristics, and TLC.

RESULTObservation and description of the experimentation were made.

CONCLUSIONDactylicapnos scandens can be identified from Genus of Dactylicapnos which has the similar morphological characteristics. The morphological and microscopic characteristics and the results of TLC can be used as evidences for quality control of this medicinal plant.

Chromatography, Thin Layer ; Papaveraceae ; anatomy & histology ; chemistry ; Pharmacognosy ; Plant Leaves ; anatomy & histology ; Plant Roots ; anatomy & histology ; Plant Stems ; anatomy & histology ; Plants, Medicinal ; anatomy & histology ; chemistry ; Quality Control

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