New diarylheptanoids from the rhizome of Alpinia officinarum Hance

Three diarylheptanoids, officinaruminane A (1), officinaruminane B (2), 5(S)-acetoxy-7-(4-dihydroxyphenyl)-1-phenyl-3-heptanone (3), together with six known ones , (5R)-5-hydroxy-1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-3-heptanone (4),(5R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4,5-dihydroxy-3-methoxyphenyl)-3-heptanone (5), 1-phenyl-7-(4-hydroxy-3-methoxyphenyl)-4E-en-3-heptanone (6), 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-4E-en-3-heptanone (7), 1-phenyl-7-(4-hydroxyphenyl)- 4E- en-3-heptanone (8), and 3,6-furan-7-(4′′-hydroxy-3′′-methoxyphenyl)-1-phenylheptane (9), were isolated from the rhizomes of Alpinia officinarum Hance by column chromatography on silica gel, MPLC and preparative thin-layer chromatography (TLC). The structures of these compounds were elucidated on the basis of mass spectrometry, 1H NMR, 13C NMR, HMQC and HMBC data. Among them, 1 is a diarylheptanoid with a pyridine ring, and 2 is a diarylheptane monoterpene.