A new flavanone glycoside from the dried immature fruits of Poncirus trifoliata

A new flavanone glycoside, (2R)-5-hydroxy-4'-methoxyflavanone-7-O-{beta-glucopyranosyl-(1-->2)-beta-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E(2) (PGE(2)) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.