Bruceines K and L from the Ripe Fruits of Brucea javanica

✍ Scribed by Ming Zhao; Sin Ting Lau; Xiao Qi Zhang; Wen Cai Ye; Po Sing Leung; Chun-Tao Che; Zhi-Xiu Lin

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 192 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201100165

✦ Synopsis

Abstract

Bruceine K (1), a pentacyclic C~20~‐quassinoid bearing a unique 12,20‐epoxy moiety, and bruceine L (2), along with the ten known compounds (6__S__,7__E__)‐6,9,10‐trihydroxy‐ and (6__S__,7__E__)‐6,9‐dihydroxymegastigma‐4,7‐dien‐3‐one (3 and 4, resp.), cleomiscosins A–C, luteoline, quercetine, bruceantinol, pinoresinol, and thevetiaflavone, were isolated from the ripe fruits of Brucea javanica. Bruceines K (1) and L (2) were determined to be (1__β__,2__α__,11__β__,12__β__,14__ξ__,15__β__)‐12,20‐epoxy‐1,2,11,13,14,15‐hexahydroxypicras‐3‐en‐16‐one and (1__β__,2__α__,11__β__,12__β__,15__β__)‐13,20‐epoxy‐1,2,11,12‐tetrahydroxy‐16‐oxo‐15‐(senecioyloxy)picras‐3‐en‐21‐oic acid methyl ester (senecioic acid=3‐methylbut‐2‐enoic acid), respectively, on the basis of NMR (^1^H‐ and ^13^C‐NMR, DEPT, ^1^H,^1^H‐COSY, NOESY, HMQC, and HMBC) and ESI‐MS data. Among the known compounds, (6__S__,7__E__)‐6,9,10‐trihydroxy‐ and (6__S__,7__E__)‐6,9‐dihydroxymegastigma‐4,7‐dien‐3‐one (3 and 4, resp.), cleomiscosin C, luteoline, quercetine, and thevetiaflavone were isolated for the first time from the Brucea plants.