Antiemetic principles of Alpinia officinarum.
Bioasay-guided fractionation of the antiemetic constituents of Alpinia officinarum was performed, and eight compounds (1-8) including a new compound were isolated. Among the seven known compounds, two flavonoids (1, 2), four diarylheptanoids (3, 5, 6, 8), and one sterol (4) were obtained, with five (2-6) of those compounds showing antiemetic activity in a copper sulfate induced emesis assay in young chicks. The structure of the new compound 7, which also showed antiemetic activity, was determined as 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-3-heptanone. The structure of 7 was established on the basis of spectroscopic data interpretation.
D000818:Animals; D000932:Antiemetics / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002645:Chickens; D002851:Chromatography, High Pressure Liquid; D019327:Copper Sulfate / Q000494:pharmacology; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007564:Japan; D008297:Male; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010840:Phytosterols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D027343:Rhizome; D013237:Stereoisomerism; D019862:Zingiberales / Q000737:chemistry*
D000932:Antiemetics; D036381:Diarylheptanoids; D004365:Drugs, Chinese Herbal; D005419:Flavonoids; D010840:Phytosterols; D019327:Copper Sulfate