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4 H ‐Chromenone Glycosides from Eranthis hyemalis (L.) S ALISBURY
Author(s) -
Kopp Brigitte,
Kubelka Erika,
Reich Christian,
Robien Wolfgang,
Kubelka Wolfgang
Publication year - 1991
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.19910740318
Subject(s) - chemistry , glycoside , stereochemistry , hydrolysis , hydroxymethyl , ranunculaceae , organic chemistry , botany , biology
Abstract Investigation of the tubers of Eranthis hyemalis ( Ranunculaceae ) afforded six chromenone glycosides. Their structures have been elucidated mainly by spectroscopic (FAB‐MS, 2D‐NMR techniques) and chemical methods (acidic and enzymatic hydrolysis) as 9‐{[(β‐ D ‐glucopyranosyl)oxy]methyl}‐8,11‐dihydro‐5‐hydroxy‐2‐methyl‐4 H ‐pyrano[2,3‐ g ][1]benzoxepin‐4‐one ( 1 ), 9‐{[(β‐ D ‐gentiobiosyl)oxy]methyl}‐8,11‐dihydro‐5‐hydroxy‐2‐methyl‐4 H ‐pyrano[2,3‐ g ][1]benzoxepin‐4‐one( 2 ), 9‐{[(β‐ D ‐glucopyranosvl)oxy]melhyl}‐8,11‐dihydro‐5‐hydroxy‐2‐(hydroxy‐methyl)‐4 H ‐pyrano[2,3‐ g ][1]benzoxepin‐4‐one( 3 ), 8‐{(2 E )‐4‐[(β‐ D ‐glucopyranosyl)oxy]‐3‐methylbut‐2‐enyl}‐5,7‐dihydroxy‐2‐methyl‐4 H ‐1‐benzopyran‐4‐one ( 4 ), 8‐{(2 E )‐4‐[(β‐ D ‐glucopyranosyi)oxy]‐3‐methylbut‐2‐enyl}‐5,7‐dihydroxy‐2‐(hydroxymethyl)‐4 H ‐1‐benzopyran‐4‐one ( 5 ), and 7‐{[(β‐ D ‐glucopyranosy1)oxy]methyl}‐2,3‐dihydro‐2‐(l‐hydroxy‐1‐methylethyl)‐4‐methoxy‐5 H ‐furo[3,2‐ g ][1]benzopyran‐5‐one ( 6 ). Compound 2 exhibited negative inotropic activity.