Hiroko Arai, - and Kazumasa Zaima, - and Erika Mitsuta, - and Haruka Tamamoto, - and Aiko Saito, - and Yusuke Hirasawa, - and Abdul Rahman, - and Idha Kusumawati, - and Noor Cholies Zaini, - and Hiroshi Morita, - (2012) Alstiphyllanines I–O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity. Bioorganic & medicinal chemistry, 20 (11). pp. 3454-3459. ISSN 1464-3391

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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 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.

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