Unusual p‐Coumarates from the Stems of Vaccinium myrtillus |
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| Authors: | Simona Hybelbauerová Jan Sejbal Martin Dračínský Iva Rudovská Bohumír Koutek |
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| Institution: | 1. Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, 128?43 Prague 2, Czech Republic;2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166?10 Prague 6, Czech Republic (phone: +420‐220183201;3. fax: +420‐220183582) |
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| Abstract: | 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 (2S,4R)‐4‐(β‐D ‐glucopyranosyloxy)pentan‐2‐yl (2E)‐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. |
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| Keywords: | Vaccinium myrtillus Coumarates Terpenoids Pentane‐2 4‐diol coumarates Oleanane‐type triterpenoids Ursane‐type triterpenoids |
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