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Eudesmane Derivatives from Hieracium intybaceum
Author(s) -
Grass Sandra,
Zidorn Christian,
Ellmerer Ernst P.,
Stuppner Hermann
Publication year - 2004
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200490031
Subject(s) - chemistry , stereochemistry , computational biology , biology
Two new eudesmanolides, 4 β ‐H,3 β ‐( β ‐ D ‐glucopyranosyloxy)eudesma‐1,11(13)‐dien‐12,6‐olide ( 5a ) and 3 β ‐ D ‐glucopyranosyloxyeudesma‐1,4(15),11(13)‐trien‐12,6‐olide ( 5b ), as well as two related, known compounds, tuberiferin ( 7a ) and dehydrobrachylaenolide ( 7b ), were isolated from the CH 2 Cl 2 extract of subaerial parts of Hieracium intybaceum All. Compounds 6a, 6b, 8a , and 8b , the Me esters of the corresponding sesquiterpenic acids related to 5a, 5b, 7a , and 7b , respectively, were obtained as artifacts during the isolation process. Additionally, linoleic acid ( 1 ), linolenic acid ( 2 ), the lignane syringaresinol 4′‐O‐ β ‐ D ‐glucopyranoside ( 3 ), and the guaianolide dehydrocostus lactone ( 4 ) were also isolated from H. intybaceum. Structure elucidations were based on mass spectrometry and extensive 1D‐ and 2D‐NMR spectroscopy.