Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter

被引：55

作者：

Arai, Hiroko ^{[1
]}

Hirasawa, Yusuke ^{[1
]}

Rahman, Abdul ^{[2
]}

Kusumawati, Idha ^{[2
]}

Zaini, Noor Cholies ^{[2
]}

Sato, Seizo ^{[3
]}

Aoyama, Chihiro ^{[3
]}

Takeo, Jiro ^{[3
]}

Morita, Hiroshi ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

[2] Airlangga Univ, Fac Pharm, Jalan Dharmawangsa Dalam 60286, Surabaya, Indonesia

[3] Nippon Suisan Kaisha Ltd, Cent Res Lab, Tokyo 1920906, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 06期

关键词：

Indole alkaloids; Alstonia macrophylla; Alstiphyllanines E-H; SGLT; AFFINITY NA+/GLUCOSE COTRANSPORTER; KOPSIA-FLAVIDA BLUME; INDOLE ALKALOIDS; IN-VITRO; SCHOLARIS; LEAVES;

D O I：

10.1016/j.bmc.2010.01.077

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2152 / 2158

页数：7

共 25 条

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