title: Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter.
abstract: Three new picraline-type alkaloids, alstiphyllanines E-G (1-3) and a new ajmaline-type alkaloid, alstiphyllanine H (4) were isolated from the leaves of Alstonia macrophylla together with 16 related alkaloids (5-20). Structures and stereochemistry of 1-4 were fully elucidated and characterized by 2D NMR analysis. Alstiphyllanines E and F (1 and 2) showed moderate Na(+)-glucose cotransporter (SGLT1 and SGLT2) inhibitory activity. A series of a hydroxy substituted derivatives 21-28 at C-17 of the picraline-type alkaloids have been derived as having potent SGLT inhibitory activity. 10-Methoxy-N(1)-methylburnamine-17-O-veratrate (6) exhibited potent inhibitory activity, suggesting that the presence of an ester side chain at C-17 may be important to show SGLT inhibitory activity. Structure activity relationship of alstiphyllanines on inhibitory activity of SGLT was discussed.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa, Tokyo 142-8501, Japan.
authors.forename: Hiroko
authors.initials: H
authors.lastname: Arai
authors.affiliation: Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa, Tokyo 142-8501, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Hirasawa
authors.affiliation: Faculty of Pharmacy, Airlangga University, Jalan Dharmawangsa Dalam, Surabaya 60286, Indonesia.
authors.forename: Abdul
authors.initials: A
authors.lastname: Rahman
authors.affiliation: Faculty of Pharmacy, Airlangga University, Jalan Dharmawangsa Dalam, Surabaya 60286, Indonesia.
authors.forename: Idha
authors.initials: I
authors.lastname: Kusumawati
authors.affiliation: Faculty of Pharmacy, Airlangga University, Jalan Dharmawangsa Dalam, Surabaya 60286, Indonesia.
authors.forename: Noor Cholies
authors.initials: NC
authors.lastname: Zaini
authors.affiliation: Central Research Laboratory, Nippon Suisan Kaisha, Ltd, 559-6 Kitano-machi, Hachioji, Tokyo 192-0906, Japan.
authors.forename: Seizo
authors.initials: S
authors.lastname: Sato
authors.affiliation: Central Research Laboratory, Nippon Suisan Kaisha, Ltd, 559-6 Kitano-machi, Hachioji, Tokyo 192-0906, Japan.
authors.forename: Chihiro
authors.initials: C
authors.lastname: Aoyama
authors.affiliation: Central Research Laboratory, Nippon Suisan Kaisha, Ltd, 559-6 Kitano-machi, Hachioji, Tokyo 192-0906, Japan.
authors.forename: Jiro
authors.initials: J
authors.lastname: Takeo
authors.affiliation: Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa, Tokyo 142-8501, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Morita
mesh_terms: D031051:Alstonia / Q000737:chemistry*; D000818:Animals; D019556:COS Cells; D002478:Cells, Cultured; D002522:Chlorocebus aethiops; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008968:Molecular Conformation; D018515:Plant Leaves / Q000737:chemistry*; D051269:Sodium-Glucose Transporter 1 / Q000037:antagonists & inhibitors*; D000077203:Sodium-Glucose Transporter 2 Inhibitors; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D026121:Indole Alkaloids; D051269:Sodium-Glucose Transporter 1; D000077203:Sodium-Glucose Transporter 2 Inhibitors; C549690:alstiphyllanine E; C549689:alstiphyllanine H