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

A new flavanone glycoside, (2R)-5-hydroxy-4′-methoxyflavanone-7-O- {β-glucopyranosyl-(1→2)-β-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 E₂ (PGE₂) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.