• Bulletin of the Korean Chemical Society
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• v.26 no.3
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• pp.447-450
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• 2005

The crude methanol extract of the fruits of Amomum tsao-ko (Zingiberaceae) showed cytotoxic activity. Bioactivity-guided separation led to the isolation of a diarylheptanoid, tsaokoarylone [7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hepta-4E,6E-dien-3-one] (2). 2 showed cytotoxicity at 4.9 and 11.4 $\mu$g/mL ($IC_{50}$) against human nonsmall cell lung cancer A549 and human melanoma SK-Mel-2, respectively, determined by SRB colorimetric method. During purification-(4-hydroxyphenyl)-4-hydroxyhexan-2-one (4) together with three known diarylheptanoids was also isolated. Their structures were determined from interpretation of spectroscopic data (IR, UV, MS, and NMR) and synthesis confirmed the structure of 2.

• Natural Product Sciences
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• v.25 no.1
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• pp.76-80
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• 2019

Bioactivity-guided fractionation of MeOH extract of the dried fruits of Amomum tsao-ko led to isolation of nine compounds (1 - 9). Their structures were elucidated by spectroscopic methods including extensive 1D and 2D-NMR, as alpinetin (1), naringenin-5-O-methyl ether (2), naringenin (3), hesperetin (4), 2',4',6'-trihydroxy-4-methoxy chalcone (5), tsaokoin (6), boesenbergin B (7), 4-hydroxyboesenbergin B (8), and tsaokoarylone (9). Of these, compound 8 was isolated from a natural source for the first time, which was previously reported as a synthetic product. The isolated compounds (1 - 9) were tested for their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages. Among them, three chalcone derivatives (compounds 5, 7, and 8) and a diarylheptanoid (compound 9) exhibited significant inhibitory activity on the NO production with $IC_{50}$ values ranging from 10.9 to $22.5{\mu}M$.