New Pavine N-Oxide Alkaloids from the Stem Bark of Cryptocarya chinensis HEMSL.

Lin, Fu Wen; Wang, Jhi Joung; Wu, Tian Shung

doi:10.1248/cpb.50.157

Cited by 26 publications

(18 citation statements)

References 12 publications

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“…Phytochemical studies have revealed that this genus produces alkaloids, 2-pyrones and flavonoids as the main secondary metabolite constituents, e.g. see [2][3][4][5][6][7][8][9][10]. Recently, we reported chalcone and flavanone derivatives from C. costata that exhibited cytotoxic activity against murine leukemia P-388 cells [9].…”

Section: Introductionmentioning

confidence: 99%

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

et al. 2009

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Two chalcone derivatives, 2'-hydroxychalcone (1) and desmethylinfectocaryone (2), together with five known phenolic compounds infectocaryone (3), cryptocaryone (4), kurzichalcolactone A (5), pinocembrin (6) and trans-N-feruloyltyramine (7), were isolated from the methanol extract of the wood of Cryptocarya konishii. The structures of the new compounds were determined based on the analysis of spectroscopic data, including UV, IR, 1D and 2D NMR, and mass spectra. Evaluation of the cytotoxic and tyrosine kinase inhibitory activities of compounds 1-7 showed that compounds 2-4 strongly inhibited the growth of murine leukemia P-388 cells, whereas compound 4 significantly inhibited the enzyme.

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Section: Introductionmentioning

confidence: 99%

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

et al. 2009

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“…This compound was tentatively identified as 6-methyl-1,3-dioxolo[4,5-g]isoquinolinium (i.e., hydrastonine). Preliminary results on the pharmacology of this metabolite and evidence for its presence in the bark of Cryptocarya chinensis have been reported by Lin et al (2002). Structurally, M5 is similar to the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, which may have some bearing on the safety of Hydrastis.…”

Section: Resultsmentioning

confidence: 90%

Hydrastine Pharmacokinetics and Metabolism after a Single Oral Dose of Goldenseal (Hydrastis canadensis) to Humans

et al. 2015

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The disposition and metabolism of hydrastine was investigated in 11 healthy subjects following an oral dose of 2.7 g of goldenseal supplement containing 78 mg of hydrastine. Serial blood samples were collected for 48 hours, and urine was collected for 24 hours. Hydrastine serum and urine concentrations were determined by Liquid Chromatography-tandem mass spectrometry (LC-MS/MS). Pharmacokinetic parameters for hydrastine were calculated using noncompartmental methods. The maximal serum concentration (C max ) was 225 6 100 ng/ml, T max was 1.5 6 0.3 hours, and area under the curve was 6.4 6 4.1 ng×h/ml×kg. The elimination half-life was 4.8 6 1.4 hours. Metabolites of hydrastine were identified in serum and urine by using liquid chromatography coupled to highresolution mass spectrometry. Hydrastine metabolites were identified by various mass spectrometric techniques, such as accurate mass measurement, neutral loss scanning, and product ion scanning using Quadrupole-Time of Flight (Q-ToF) and triple quadrupole instruments. The identity of phase II metabolites was further confirmed by hydrolysis of glucuronide and sulfate conjugates using bovine b-glucuronidase and a Helix pomatia sulfatase/glucuronidase enzyme preparation. Hydrastine was found to undergo rapid and extensive phase I and phase II metabolism. Reduction, O-demethylation, N-demethylation, hydroxylation, aromatization, lactone hydrolysis, and dehydrogenation of the alcohol group formed by lactone hydrolysis to the ketone group were observed during phase I biotransformation of hydrastine. Phase II metabolites were primarily glucuronide and sulfate conjugates. Hydrastine undergoes extensive biotransformation, and some metabolites may have pharmacological activity. Further study is needed in this area.

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“…This species is a medium sized tree that grows up to 10 m tall. Based on previously reported phytochemical and pharmacological studies, the genus Cryptocarya are known to be prolific producers of flavonoids, chalcones, lactones, α-pyrones and mainly alkaloids [14,15,16,17,18,19,20,21,22,23,24] with varied biological activities. A preliminary study on the leaves of the Cryptocarya nigra reported the presence of coumarins and flavonoids and their cytotoxic activity against murine leukemia P-388 cells [25].…”

Section: Introductionmentioning

confidence: 99%

Antiplasmodial Alkaloids from the Bark of Cryptocarya nigra (Lauraceae)

et al. 2013

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Abstract:A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC 50 value of 2.82 μg/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished by means of high field 1D-and 2D-NMR, IR, UV and LCMS spectral data. The isolated extract constituents (+)-N-methylisococlaurine (1), atherosperminine (2) and 2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC 50 values of 5.40, 5.80 and 0.75 μM, respectively. In addition, (+)-N-methylisocolaurine (1) and atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC 50 values of 29.56 ug/mL and 54.53 ug/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC 50 values of 50.08 ug/mL and 42.87 ug/mL, respectively.

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New Pavine N-Oxide Alkaloids from the Stem Bark of Cryptocarya chinensis HEMSL.

Cited by 26 publications

References 12 publications

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

Hydrastine Pharmacokinetics and Metabolism after a Single Oral Dose of Goldenseal (Hydrastis canadensis) to Humans

Antiplasmodial Alkaloids from the Bark of Cryptocarya nigra (Lauraceae)

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