Sugar ring isomerization in C-arabinosylflavones |
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Authors: | Elisabeth Besson Jean Chopin |
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Institution: | Laboratoire de Chimie Biologique, Université Claude Bernard, Lyon I, 69622 Villeurbanne Cedex, France |
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Abstract: | 6-C-α-l-Arabinopyranosyl- and furanosylacacetins have been synthesized. They are isomerized by short acid treatment to give a mixture of the four anomer/ring size combinations without any Wessely-Moser isomerization. In the same conditions molludistin (8-C-α-l-arabinopyranosylgenkwanin) led only to a mixture of molludistin and 8-C-α-l-arabinofuranosylgenkwanin. This is the first demonstration of ring sugar isomerization in C-glycosylflavones. In usual solvent systems, α-anomers are easily separated from β-anomers, whereas corresponding pyranosyl and furanosyl anomers are not. However, they are easily separated after permethylation and characteristic features are found in the mass spectra of PM 6-C-arabinofuranosyl isomers. |
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Keywords: | sugar ring isomerization EIMS |
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