New Long-Chain Esters and Adenine Analogs from the Leaves of Formosan Bridelia balansae

✍ Scribed by Yeh-Hsin Tsai; Ih-Sheng Chen; Ian-Lih Tsai

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 131 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390198

✦ Synopsis

Abstract

Six new compounds, including the two long‐chain esters balansenate I (=6,8,11‐trimethyldodecanoic acid (2__E__)‐3‐methylhexadec‐2‐enyl ester; 1) and balansenate II (=10,12,15‐trimethylhexadedecanoic acid (2__E__)‐3‐methylhexadec‐2‐enyl ester; 2), the eburicane‐like triterpenoid bridelone (=hexadecahydro‐4,4,10,13,14‐pentamethyl‐17‐(5‐methyl‐1,4‐dimethylenehexyl)‐3__H__‐cyclopenta[a]phenanthren‐3‐one; 3), the ‘deimino‐xanthine', bridelonine (=5‐(3‐methylbut‐2‐enyl)pyrrolo[3,4‐d]imidazole‐4,6(1__H__,5__H__)‐dione; 6), and the two adenine analogs 9‐(3‐methylbut‐2‐enyl)adenine (7) and 1‐(3‐methylbut‐2‐enyl)adenine (8), besides three known compounds, i.e., N^6^‐(3‐methylbut‐2‐enyl)adenine (4), 3‐(3‐methylbut‐2‐enyl)adenine (5), and adenine (9), were isolated from the leaves of Formosan Bridelia balansae. The novel skeleton of 6 consists of a fused pyrrolidine‐2,5‐dione and imidazole moiety. The already known adenines 7 and 8 were isolated for the first time from a plant. The structures of the isolated compounds were elucidated by spectroscopic analyses.