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

Hiroko Arai, Yusuke Hirasawa, Abdul Rahman, Idha Kusumawati, Noor Cholies Zaini, Seizo Sato, Chihiro Aoyama, Jiro Takeo, Hiroshi Morita

Research output: Contribution to journalArticlepeer-review

69 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2152-2158
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number6
DOIs
Publication statusPublished - 15 Mar 2010

Keywords

  • Alstiphyllanines E-H
  • Alstonia macrophylla
  • Indole alkaloids
  • SGLT

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