The Pavine and Isopavine Alkaloids

Gözler, Belkıs; Lantz, Melinda; Shamma, Maurice

doi:10.1021/np50027a001

Cited by 35 publications

(25 citation statements)

References 29 publications

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“…The alkaloid (3), C21H25N04 showed spectral data (IR, LV, 1H NMR, EI-MS), and TLC behaviour identical to an authentic sample of argemonine, previously isolated from T. minus (7). The physical data of 3 agree well with those published in the literature for argemonine (1).…”

Section: Resultssupporting

confidence: 87%

Two New Pavine Alkaloids fromThalictrum simplex

Velcheva¹,

Dutschewska²,

Danghaaghiin³

et al. 1993

Planta Med

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Section: Resultssupporting

confidence: 87%

Two New Pavine Alkaloids fromThalictrum simplex

Velcheva¹,

Dutschewska²,

Danghaaghiin³

et al. 1993

Planta Med

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“…The UV maxima of przewalidine chloride (12) are typical of isopavine alkaloids (22). In its 1H-NMR spectrum, two methoxy groups at 63.82 and 3.80 ppm and two N-methyl groups at 142.9 ppm, for oxygenated aromatic c-atoms, two hydroxy groups were assumed.…”

Section: Resultsmentioning

confidence: 99%

Alkaloids fromThalictrum przewalskii

Zhang

Rüċker²,

Breitmaier³

et al. 1998

Planta Med

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Nine new alkaloids przewaline, przewalskine, przewalskinine, przewalstine, przewalstinine, przewalstidine, przewalstidinine, przewalidine chloride, and 8-hydroxypseudocoptisine chloride were isolated from Thalictrum przewalskii Maxim., together with the known alkaloids berberinium chloride, magnoflorine chloride, N-methylpalaudinium chloride, thalphenine chloride, and N-methylnantenium chloride. Their structures were determined by spectroscopy including EI-MS, FAB-MS, (1)H-NMR, (13)C-NMR, C,H-COSY, C,H-COLOC, HMQC and HMBC techniques.

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“…The pavine alkaloids are derived biogenically from benzylisoquinolines (Gözler et al ., 1983) and usually exist in plants of Lauraceae (Tomita et al ., 1966). Pavines have been shown to possess many biological activities such as behavioural effects (Meisenberg et al ., 1984) and antitumour effects (Wu et al ., 1989).…”

Section: Introductionmentioning

confidence: 99%

Cardiac electrophysiologic and antiarrhythmic actions of a pavine alkaloid derivative, O‐methyl‐neocaryachine, in rat heart

Chang

Hung

et al. 2002

British J Pharmacology

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1 O-methyl-neocaryachine (OMNC) suppressed the ischaemia/reperfusion-induced ventricular arrhythmias in Langendor-perfused rat hearts (EC 50 =4.3 mM). Its electrophysiological eects on cardiac myocytes and the conduction system in isolated hearts as well as the electromechanical eects on the papillary muscles were examined. 2 In rat papillary muscles, OMNC prolonged the action potential duration (APD) and decreased the maximal rate of depolarization (V max ). As compared to quinidine, OMNC exerted less eects on both the V max and APD but a positive inotropic eect. 3 In the voltage clamp study, OMNC decreased Na + current (I Na ) (IC 50 =0.9 mM) with a negativeshift of the voltage-dependent inactivation and a slowed rate of recovery from inactivation. The voltage dependence of I Na activation was, however, unaected. With repetitive depolarizations, OMNC blocked I Na frequency-dependently. OMNC blocked I Ca with an IC 50 of 6.6 mM and a maximum inhibition of 40.7%. 4 OMNC inhibited the transient outward K + current (I to ) (IC 50 =9.5 mM) with an acceleration of its rate of inactivation and a slowed rate of recovery from inactivation. However, it produced little change in the steady-state inactivation curve. The steady-state outward K + current (I SS ) was inhibited with an IC 50 of 8.7 mM. The inward recti®er K + current (I K1 ) was also reduced by OMNC. 5 In the perfused heart model, OMNC (3 to 30 mM) prolonged the ventricular repolarization time, the spontaneous cycle length and the atrial and ventricular refractory period. The conduction through the AV node and His-Purkinje system, as well as the AV nodal refractory period and Wenckebach cycle length were also prolonged (30 mM). 6 In conclusion, OMNC blocks Na + , I to and I SS channels and in similar concentrations partly blocks Ca 2+ channels. These eects lead to a modi®cation of the electromechanical function and may likely contribute to the termination of ventricular arrhythmias. These results provide an opportunity to develop an eective antiarrhythmic agent with modest positive inotropy as well as low proarrhythmic potential.

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The Pavine and Isopavine Alkaloids

Cited by 35 publications

References 29 publications

Two New Pavine Alkaloids fromThalictrum simplex

Two New Pavine Alkaloids fromThalictrum simplex

Alkaloids fromThalictrum przewalskii

Cardiac electrophysiologic and antiarrhythmic actions of a pavine alkaloid derivative, O‐methyl‐neocaryachine, in rat heart

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