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Identification of allocryptopine and protopine metabolites in rat liver S9 by high-performance liquid chromatography/quadrupoletime- of-flight mass spectrometry

RATIONALE: Allocryptopine (AL) and protopine (PR) have been extensively studied because of their anti-parasitic, antiarrhythmic, anti-thrombotic, anti-inflammatory and anti-bacterial activity. However, limited information on the pharmacokinetics and metabolism of AL and PR has been reported. Therefore, the purpose of the present study was to investigate the in vitro metabolism of AL and PR in rat liver S9 using a rapid and accurate high-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry (HPLC/QqTOFMS) method. METHODS: The incubation mixture was processed with 15% trichloroacetic acid (TCA). Multiple scans of AL and PR metabolites and accurate mass measurements were automatically performed simultaneously through data-dependent acquisition in only a 30-min analysis. The structural elucidations of these metabolites were performed by comparing their changes in accurate molecular masses and product ions with those of the precursor ion or metabolite. RESULTS: Eight and five metabolites of AL and PR were identified in rat liver S9, respectively. Among these metabolites, seven and two metabolites of AL and PR were identified in the first time, respectively. The demethylenation of the 2,3-methylenedioxy, the demethylation of the 9,10-vicinal methoxyl group and the 2,3-methylenedioxy group were the main metabolic pathways of AL and PR in liver S9, respectively. In addition, the cleavage of the methylenedioxy group of the drugs and subsequent methylation or O-demethylation were also the common metabolic pathways of drugs in liver S9. In addition, the hydroxylation reaction was also the metabolic pathway of AL. CONCLUSIONS: This was the first investigation of in vitro metabolism of AL and PR in rat liver S9. The detailed structural elucidations of AL and PR metabolites were performed using a rapid and accurate HPLC/QqTOFMS method. The metabolic pathways of AL and PR in rat were tentatively proposed based on these characterized metabolites and early reports.

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Prevalence and current therapy in chronic liver disorders

Background: Herbal medicine plays an important role in health, particularly in remote parts of developing areas with few health facilities. According to WHO estimates, about three-quarters of the world’s population currently use herbs or traditional medicines to treat various ailments, including liver diseases. Several studies have found that the use of medicinal plants was effective in the treatment of infectious and non-infectious diseases. Hepatitis and liver cirrhosis associated with many clinical manifestations can be treated with allopathic medicines, but reports of a number of side effects including immunosuppression, bone marrow suppression, and renal complications have motivated researchers to explore more natural herbal medicines with low or no side effects and with high efficacy in treating hepatic diseases. Methods: Databases including PubMed, Medline, and Google Scholar were searched for findings on the hepatoprotective effects of plants. Results: Various medicinal plants are used for the treatment of liver disorders. The range of alternative therapies is huge, and they are used worldwide, either as part of primary health care or in combination with conventional medicine. Hepatoprotective plants contain a variety of chemical constituents including flavonoids, alkaloids, glycosides, carotenoids, coumarins, phenols, essential oil, organic acids, monoterpenes, xanthenes, lignans, and lipids. Conclusion: This review shows that numerous plants are found to contain hepatoprotective compounds. However, further studies are needed to determine their association with existing regimes of antiviral medicines and to develop evidence-based alternative medicine to cure different kinds of liver disease in humans.

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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Synthetic Route of 1081-17-0. In my other articles, you can also check out more blogs about 1081-17-0

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Acetylcholinesterase inhibitors from Corydalis yanhusuo

In a bioassay-guided search for acetylcholinesterase (AChE) inhibitors from Chinese natural resources, eight isoquinoline alkaloids, tetrahydropalmatine (1), corydaline (2), protopine (3), berberine (4), palmatine (5), jatrorrhizine (6), coptisine (7) and dehydrocorydaline (8), were isolated from the methanolic extract of the tubers of Corydalis yanhusuo. Structures of these compounds were identified by spectroscopic techniques. Compounds 4-8 inhibited AChE activity in a dose-dependent manner, and the IC50 values were 0.47¡À0.01, 0.74¡À0.06, 2.08¡À0.09, 1.01¡À0.03 and 0.62¡À0.05mu M, respectively. Structure-activity relationship analysis suggested that aromatisation at ring C, as well as substitutions at C-2, C-3, C-9, C-10 and C-13 affect the AChE activity of protoberberine alkaloids.

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ALKALOIDS FROM Papaver oreophilum F. J. RUPR.

In addition to the known alkaloids from Papaver oreophilum F.J.RUPR., i.e. oridine, mecambridine, isocorydine, protopine, oreodine, rhoeadine, nuciferine, isooridine (oridine-2), oridine-3, alkaloid PO-5 (R-K, alborine) and trace alkaloids rhoeagenine, oreogenine, isorhoeadine, papaverrubines A, D and E, sanguinarine, N-methyloridine and coptisine, we isolated from the aerial part or from the roots the following further alkaloids: allocryptopine and – from the quaternary fraction – menisperine and magnoflorine (3.6percent), which is the main alkaloid in the roots.Further corydine and trace amounts of papaverrubine C, chelirubine, berberine, corysamine and probably O-methyloridine and O,N-dimethyloridine were also detected.It was shown that oridine-3 was identical with the hydrochloride of isooridine.

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Development and validation of a HPLC-ESI-MS/MS method for simultaneous quantification of fourteen alkaloids in mouse plasma after oral administration of the extract of corydalis yanhusuo tuber: Application to pharmacokinetic study

The tuber of Corydalis yanhusuo is a famous traditional Chinese medicine and found to have potent pharmacological effects, such as antinociceptive, antitumor, antibacterial, anti-inflammatory, and anti-depressive activities. Although there are several methods to be developed for the analysis and detection of the bioactive ingredients? alkaloids, so far, only few prominent alkaloids could be quantified, and in vitro and in vivo changes of comprehensive alkaloids after oral administration are still little known. In this study, we first developed a simple and sensitive high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS) method to quantify the comprehensive alkaloids of extracts of C. yanhusuo in mouse plasma, using nitidine chloride as an internal standard. As results, at least fourteen alkaloids, including an aporphine (oxoglaucine), a protopine (protopine), five tertiary alkaloids (corydaline, tetrahydroberberine, tetrahydropalmatine, tetrahydrocolumbamine, and tetrahydrocoptisine) and seven quaternary alkaloids (columbamine, palmatine, berberine, epiberberine, coptisine, jatrorrhizine, and dehydrocorydaline) could be well quantified simultaneously in mouse plasma. The lower limits of quantification were greater than, or equal to, 0.67 ng/mL, and the average matrix effects ranged from 96.4% to 114.3%. The mean extraction recoveries of quality control samples were over 71.40%, and the precision and accuracy were within the acceptable limits. All the analytes were shown to be stable under different storage conditions. Then the established method was successfully applied to investigate the pharmacokinetics of these alkaloids after oral administration of the extract of Corydalis yanhusuo in mice. To the best of our knowledge, this is the first document to report the comprehensive and simultaneous analyses of alkaloids of C. yanhusuo in mouse plasma. It was efficient and useful for comprehensive pharmacokinetic and metabolomic analyses of these complex alkaloids after drug administration.

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Corydalis edulis total alkaloids (CETA) ameliorates cognitive dysfunction in rat model of Alzheimer disease through regulation of the antioxidant stress and MAP2/NF-kappaB

Background: In recent years, the morbidity of Alzheimer’s disease in the world has become more and more serious. Therefore, it is an important means to find new drugs for treating AD from traditional medicines. It was found that Corydalis edulis Maxim. has a significant effect in the treatment of Alzheimer’s disease (AD) in traditional application. In this work, we evaluated the efficacy of Corydalis edulis Maxim. total alkaloids (CETA) in AD model rats. Methods: In this work, CETA was prepared by alkali extraction and acid precipitation, 11 alkaloids were identified by UPLC-MS/MS from CETA. AD model rats induced with D-galactose (D-gal) for 7 weeks. In modeling, the different doses of CETA (5, 20 mg/kg/Day) were continuously administered. Firstly, the change of the cognitive function, behavior, brain tissue pathology, and the activity of ROS, MDA, SOD, IL-1beta, TNF-alpha and CAT in rat hippocampal homogenate was measurement. Finally, the protein expression of Abeta, microtubule-associated protein 2 (MAP2) and nuclear factor (kappaBp65) in rat brain was measurement. Result: CETA was found to have the activity in regulating AD. Compared with the normal control group, the levels of SOD and CAT in the hippocampus of the AD model group were decreased, and the level of ROS, MDA, IL-1beta and TNF-alpha was increased. The protein expression of Abeta, and NF-kappaB were increased, and MAP2 were decreased. After treatment by CETA, the levels of SOD and CAT in hippocampus of AD model rats was significantly increased, ROS, MDA, IL-1beta and TNF-alpha were significantly decreased. The protein expression of Abeta, and NF-kappaB were decreased, and MAP2 were increased. Conclusion: CETA can improve the learning and memory ability in AD model. The mechanism may be achieved by regulating the oxidative stress and inflammatory of AD rats, inhibiting the protein expression levels of Abeta, and NF-kappaB, and promote the protein expression the levels of MAP2. Among them, 5 mg/kg is more effective than 20 mg/kg of CETA. Therefore, the therapeutic potential of CETA has been confirmed by our research, which may be a valuable drug for the treatment of AD.

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Alkaloids from Papaver setigerum DC

Two new benzylisoquinoline alkaloids of the papaverine type, setigerine (racemic alpha-methoxypapaverine, 1b) and setigeridine (1c), were isolated from Papaver setigerum DC. as the minor constituents. Their structures were established by spectral data and X-ray crystallographic analysis. Papaverine (1a) was isolated as the major alkaloid of the plant (0.05 wt.%) besides of less amounts of morphine, codeine and rhoeadine, In a low yield, protopine, cryptopine, thebaine, rhoeagenine, and N-methyl-thebainium (as iodide) were obtained and small quantities of laudanosine, stylopine, isoboldine, scoulerine, papaverrubine A, B, C, D and E, coptisine, corytuberine, and magnoflorine were identified by thin layer chromatography.

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ALKALOIDS OF Glaucium fimbrilligerum

From the epigeal part and roots of Glaucium fimbrilligerum 22 alkaloids have been isolated, of which three have proved to be new – d-isocorytuberine, dehydrocorydine, and coridine N-oxide.

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Phytochemical analysis, antioxidant and analgesic activities of Incarvillea compacta maxim from the tibetan plateau

Incarvillea compacta Maxim is a traditional Tibetan plant widely used to treat rheumatic pain and bruises. We conducted qualitative analyses by liquid chromatography-mass spectrometry and quantitative analyses of the total phenols, flavonoids, and alkaloids content of different extracts of I. compacta Maxim. Antioxidant and analgesic activity were analyzed. The results showed that the methanol extract had the highest content of the various ingredients. A total of 25 constituents were identified, of which compounds 1-23 were found for the first time in this plant. The water extract had the highest capacity to clear free radicals in the antioxidant test. The water extract had dose-dependent analgesic effects in the first and second phase in a formalin test. The latency of pain from a hot-plate test was augmented by the water extract when the dose was greater than or equal to 30 g/kg. The water extract significantly decreased the amount of writhing in a dose-dependent manner compared with the control group in the acetic acid-induced writhing test. These results showed that I. compacta Maxim is a new antioxidant and analgesic agent, and this study provides information on its ingredients for further study.

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ALKALOIDS OF Glaucium fimbrilligerum. II

The alkaloids of the epigeal part and roots of the plant Glaucium fimbrilligerum have been studied.A total of 18 alkaloids has been isolated, of which epiglaufidine proved to be new, and its structure has been established.Columbamine has been isolated from the genus Glaucium for the first time, and magnoflorine and stilopine alpha-hydroxymethylate from this species of plant for the first time.

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