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Bruceines K and L from the Ripe Fruits of Brucea javanica
Author(s) -
Zhao Ming,
Lau Sin Ting,
Zhang Xiao Qi,
Ye Wen Cai,
Leung Po Sing,
Che ChunTao,
Lin ZhiXiu
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100165
Subject(s) - chemistry , dept , stereochemistry , moiety , two dimensional nuclear magnetic resonance spectroscopy , pinoresinol , carbon 13 nmr , lignan
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.