title: Alstiphyllanines I-O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity.
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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa, Tokyo 142-8501, Japan.
authors.forename: Hiroko
authors.initials: H
authors.lastname: Arai
authors.forename: Kazumasa
authors.initials: K
authors.lastname: Zaima
authors.forename: Erika
authors.initials: E
authors.lastname: Mitsuta
authors.forename: Haruka
authors.initials: H
authors.lastname: Tamamoto
authors.forename: Aiko
authors.initials: A
authors.lastname: Saito
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Hirasawa
authors.forename: Abdul
authors.initials: A
authors.lastname: Rahman
authors.forename: Idha
authors.initials: I
authors.lastname: Kusumawati
authors.forename: Noor Cholies
authors.initials: NC
authors.lastname: Zaini
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Morita
mesh_terms: D000404:Ajmaline / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D031051:Alstonia / Q000737:chemistry*; D000818:Animals; D001011:Aorta / Q000187:drug effects / Q000378:metabolism; D002118:Calcium / Q000378:metabolism; D002121:Calcium Channel Blockers / Q000494:pharmacology; D015220:Calcium Channels / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D042783:Endothelial Cells / Q000187:drug effects / Q000378:metabolism; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism; D010656:Phenylephrine / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014664:Vasodilation / Q000187:drug effects; D014665:Vasodilator Agents / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D002121:Calcium Channel Blockers; D015220:Calcium Channels; D046948:Secologanin Tryptamine Alkaloids; D014665:Vasodilator Agents; C575340:alstiphyllanine I; C575341:alstiphyllanine O; C575342:vincamedine; D000404:Ajmaline; D010656:Phenylephrine; D009569:Nitric Oxide; D002118:Calcium