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

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...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2012-06, Vol.20 (11), p.3454-3459
Main Authors: Arai, Hiroko, Zaima, Kazumasa, Mitsuta, Erika, Tamamoto, Haruka, Saito, Aiko, Hirasawa, Yusuke, Rahman, Abdul, Kusumawati, Idha, Zaini, Noor Cholies, Morita, Hiroshi
Format: Article
Language:English
Subjects:
Ajmaline - analogs & derivatives
Ajmaline - chemistry
Ajmaline - pharmacology
Ajmaline type alkaloids
alkaloids
Alstiphyllanines I–O
Alstonia - chemistry
Alstonia macrophylla
Animals
Aorta - drug effects
Aorta - metabolism
Biological and medical sciences
calcium
Calcium - metabolism
Calcium Channel Blockers - pharmacology
Calcium Channels - metabolism
Dose-Response Relationship, Drug
Drug Evaluation, Preclinical
endothelial cells
Endothelial Cells - drug effects
Endothelial Cells - metabolism
General pharmacology
In Vitro Techniques
Indole alkaloids
leaves
Magnetic Resonance Spectroscopy
Male
Medical sciences
Molecular Structure
Nitric oxide
Nitric Oxide - metabolism
nuclear magnetic resonance spectroscopy
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
phenylephrine
Phenylephrine - pharmacology
Rats
Rats, Wistar
ROCs
SAR
Secologanin Tryptamine Alkaloids - chemistry
Secologanin Tryptamine Alkaloids - pharmacology
stereochemistry
Structure-Activity Relationship
vasodilation
Vasodilation - drug effects
Vasodilator Agents - chemistry
Vasodilator Agents - pharmacology
Vasorelaxant activity
VDCs
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Summary: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 Ca2+ influx through voltage-dependent Ca2+ channels (VDCs) and/or receptor-operated Ca2+ 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.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2012.04.013