Article

Alstiphyllanines I-O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity.

Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa, Tokyo 142-8501, Japan.
Bioorganic & medicinal chemistry (impact factor: 2.82). 04/2012; 20(11):3454-9. DOI:10.1016/j.bmc.2012.04.013 pp.3454-9
Source: PubMed

ABSTRACT Seven new ajmaline type alkaloids, alstiphyllanines I-O (1-7) were isolated from the leaves of Alstonia macrophylla together with six related alkaloids (8-13). Structures and stereochemistry of 1-7 were fully elucidated and characterized by 2D NMR analysis. A series of alstiphyllanines I-O (1-7) as well as the known ajmaline type alkaloids (8-13) showed that they relaxed phenylephrine (PE)-induced contractions against rat aortic ring. Among them, vincamedine (10) showed potent vasorelaxant activity, which may be mediated through inhibition of Ca(2+) influx through voltage-dependent Ca(2+) channels (VDCs) and/or receptor-operated Ca(2+) channels (ROCs) as well as partially mediated the NO release from endothelial cells. The presence of substituents at both N-1 and C-17 may be important to show vasorelaxation activity.

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Keywords

2D NMR analysis
 
alstiphyllanines I-O
 
Alstonia macrophylla
 
endothelial cells
 
known ajmaline type alkaloids
 
new ajmaline type alkaloids
 
PE)-induced contractions
 
potent vasorelaxant activity
 
rat aortic ring
 
substituents
 
vasorelaxation activity
 
voltage-dependent Ca(2+)