Bisbenzylisoquinoline and hasubanane alkaloids from Stephania abyssinica (Dillon & A. Rich) (Menispermeceae)

From the leaves of Stephania abyssinica, three alkaloids were isolated: (−)-pseudocurine (1), (−)-pseudoisocurine (2) and (−)-10-oxoaknadinine (3). (−)-Pseudocurine and (-)-pseudoisocurine showed strong anti-plasmodial activity against both chloroquine-susceptible D6 and resistant strains of Plasmod...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2014-07, Vol.103, p.123-128
Main Authors: Omole, Ruth A., Gathirwa, Jeremiah, Akala, Hosea, Malebo, Hamisi M., Machocho, Alex K., Hassanali, Ahmed, Ndiege, Isaiah O.
Format: Article
Language:English
Subjects:
(−)-10-oxoaknadinine anti-plasmodial activity
(−)-Pseudocurine and (−)-pseudoisocurine
Alkaloids
Alkaloids - chemistry
Alkaloids - pharmacology
Antimalarials - chemistry
Antimalarials - pharmacology
Benzylisoquinolines - chemistry
Benzylisoquinolines - pharmacology
Bisbenzylisoquinoline
Hasubanane
Magnetic Resonance Spectroscopy
Menispermerceae
Molecular Structure
Plasmodium falciparum - drug effects
Stephania - chemistry
Stephania abyssinica
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Summary:From the leaves of Stephania abyssinica, three alkaloids were isolated: (−)-pseudocurine (1), (−)-pseudoisocurine (2) and (−)-10-oxoaknadinine (3). (−)-Pseudocurine and (-)-pseudoisocurine showed strong anti-plasmodial activity against both chloroquine-susceptible D6 and resistant strains of Plasmodium falciparum (IC50 0.29±0.00 and 0.31±0.01μg/ml, respectively) while (−)-pseudoisocurine exhibited moderate and mild activity (0.75±0.11 and 1.65±0.03μg/ml). [Display omitted] •Isolation of Bisbenzylisoquinoline and hasubanan alkaloids from Stephania abyssinica.•Structure determination of these compounds using NMR techniques.•Anti-plasmodial activity of Bisbenzylisoquinoline and hasubanan alkaloids.•The results aimed at developing of anti-malarial drug. Two bisbenzylisoquinoline and one hasubanane alkaloids: (−)-pseudocurine (1), (−)-pseudoisocurine (2) and (−)-10-oxoaknadinine (3), were isolated from leaf extract of Stephania abyssinica, a plant used in traditional medicine in South Nyanza region of Kenya. They were characterized using 1D (1H, 13C and DEPT) and 2D (COSY, NOESY, HMQC and HMBC) NMR techniques. (−)-Pseudocurine (1) and (−)-pseudoisocurine (2) exhibited strong to moderate anti-plasmodial activity while (−)-10-oxoaknadinine (3) showed moderate to mild activity.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2014.03.026