Abstract:
Fourteen compounds were isolated from the ethyl acetate fraction of 90% EtOH extracts of the dried fruits of
Alpinia oxyphylla by silica gel, MCI, RP-18, Sephadex LH-20, TLC and semi-preparative HPLC column chromatography. Their structures were identified by HR-ESI-MS, UV, IR, NMR, ECD and X ray single crystal diffraction spectroscopic data as: (2
R, 5
R, 7
R, 10
S)-2, 7-dihydroxyl-eudesmane-3(4), 11(12)-diene (
1),
α-rotunol (
2), diketone I (
3), (1
S, 4
S, 5
R, 7
S)-1-hydroxyl-eremophilane-9(10), 11(12)-diene-8-one (
4), cyperusol A
1 (
5), (6
R, 9
S, 10
S)-10-hydroxyl-11, 12, 13-trinor-cadinane-4(5)-ene-3-one (
6), (2
E, 4
E)-6-hydroxy-2, 6-dimethylhepta-2, 4-dienal (
7), oxyphyllacinol (
8), yakuchinone A (
9), (5
R)-5-hydroxy-1, 7-diphenylhept-3-heptanone (
10), (5
S)-5-hydroxy-7-(4″-hydroxyphenyl)-1-phenylhept-3-heptanone (
11), (5
S)-5-hydroxy-7-(4″-hydroxyl-3″-methoxyphenyl)-1-phenyl-3-heptanone (
12), 7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3, 5-heptadione (
13), bis-(2-ethylhexyl) terephthalate (
14). Compounds
1-
6 were sesquiterpenoids in which compound
1 is a new eudesmane sesquiterpenoid and compound
7 was a monoterpenoid. Compounds
8-
13 were diarylheptanoids, and compounds
2-
6 and
14 were isolated from
A.oxyphylla for the first time. The experiments on H
2O
2 induced SH-SY5Y cells showed that compounds
2,
6,
7,
12 and
13 had neuroprotective effects at low and medium concentrations. In particular, compound
6 showed obvious neuroprotective effect at low, medium and high concentrations whose cell viability was higher than that of the positive control.