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Two Unusual Methylidenecyclopropane Glucosides from Metaxya rostrata C. Presl
Author(s) -
Kainz Kerstin P.,
Virtbauer Judith,
Kählig Hanspeter,
Arion Vladimir,
Donath Oliver,
Reznicek Gottfried,
Huber Werner,
Marian Brigitte,
Krenn Liselotte
Publication year - 2012
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.201200111
Subject(s) - chemistry , fern , rhizome , stereochemistry , glycoside , alcohol , organic chemistry , botany , biology
Two new natural compounds, (1 R ,2 E )‐2‐(6‐hydroxyhexylidene)cyclopropyl‐ β ‐ D ‐glucopyranoside ( 1 ) and (6 E )‐6‐[(2 R )‐2‐( β ‐ D ‐glucopyranosyloxy)cyclopropylidene]hexanoic acid ( 2 ), glucosides of a very rare methylidenecyclopropane alcohol, as well as two known glycosides of phenolic acids, namely 4‐ O ‐ β ‐ D ‐glucopyranosylcaffeic acid ( 3 ) and ( E )‐4‐ O ‐ β ‐ D ‐glucopyranosylcoumaric acid ( 4 ), and methyl α ‐fructofuranoside ( 5 ) were isolated for the first time from the rhizomes of the tree fern Metaxya rostrata C. Presl . The structures were elucidated on the basis of detailed spectroscopic data analysis, and the structure of 1 was additionally confirmed by X‐ray crystal‐structure analysis.