Hydroxy-hydroxyphenyl-phenyl-heptanone

Four diarylheptanoids were isolated from the methanol ic extract of the rhizomes of 4. officinarum and identified on the basis of their spectral data and by chemical correlations as l,7-diphenylhept-4-en-3-one (40), 7-(4"-hydroxy-3"-methoxyphenyl)-l-phenylhept-4-en-3-one (41), 1,7-dipheny 1-5-hydroxy-3-heptanone (43) and 5-hydroxy-7-(4"-hydroxy-3"-methoxyphenyl)-l-phenyl-3-heptanone (44) [38]. From the chloroform-soluble fraction of the methanolic extract of the rhizomes of A. officinarum, three new diarylheptanoids, 5-methoxy-7-(4"-hydroxy-3"-methoxyphenyl)-l-phenyl-3-heptanone (46), 5-hydroxy-7-(4"-hydroxyphenyl)- -phenyl-3-heptanone (45) and 7-(4"-hydroxy-3"-methoxyphenyl)- -phenyl-3,5-heptanedione (49) were isolated together with 41, 43 and 44 [39]. Compound 44 was the major constituent of the chloroform-soluble fraction. Compounds 41, 43-46 and 49 showed inhibitory effect against PG synthetase and IC50 values of the compounds were reported [39]. In addition to compounds 43, 44 and 52, three new diarylheptanoids, 42,47 and 48 were isolated from the rhizomes of A. officinarum and the structures were elucidated on the basis of the spectroscopic data [40]. The configuration of C-5 of 43 and 52 was determined to be R and that of hexahydrocurcumin was S [40]. 

Hydroxy-7-(4"-hydroxyphenyl)-1 -phenyl-3-heptanone (phenylpropane ketone) Alpinia officinarum (Zingiberaceae) [rhizome] COX (PGS) (19)... 

Figure 2. Structures of diarylheptanoids isolated from Alpinia officinarum. AO-1 (5-hydroxy-7-(4 -hydroxy-3 -methoxyphenyl)- l-phenyl-3-heptanone), AO-2(5-methoxy-7-(4 -hydroxy-3 -methoxyphenyl)-l-phenyl-3-heptanone), AO-3 (7-(4 -hydroxyphenyl)-l-phenylhept-4-en-3-one), AO-4 (7-(4 -hydroxy-3"-methoxyphenyl)- l-phenylhept-4-en-3-one), AO-5 (1,7-diphenylhept-4-en-3-one).

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