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Unusual p ‐Coumarates from the Stems of Vaccinium myrtillus
Author(s) -
Hybelbauerová Simona,
Sejbal Jan,
Dračínský Martin,
Rudovská Iva,
Koutek Bohumír
Publication year - 2009
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.200900220
Subject(s) - chemistry , vaccinium myrtillus , aglycone , glycoside , stereochemistry , oleanane , terpene , phenol , organic chemistry , pentane , diol , triterpene , botany , medicine , alternative medicine , pathology , biology
The two previously unreported esters 1 and 2 of pentane‐2,4‐diol and p ‐coumaric acid (=3‐(4‐hydroxyphenyl)prop‐2‐enoic acid) along with 13 known compounds including 6 oleanane‐ and ursane‐type triterpenoids were isolated from MeOH extracts of the stems of Vaccinium myrtillus. The structures of the new compounds were assigned as (2 S ,4 R )‐4‐( β ‐ D ‐glucopyranosyloxy)pentan‐2‐yl (2 E )‐ p ‐coumarate ( 1 ) and its aglycone 2 on the basis of 1D‐ and 2D‐NMR spectroscopic analyses of the isolated and synthesized compounds and molecular modelling experiments. This is the first report on the occurrence of a chiral pentane‐2,4‐diol linker between the phenol‐derived acid and a glycoside part in natural products.