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Antioxidative compounds isolated from the rhizomes of smaller galanga ( Alpinia officinarum Hance)
Author(s) -
Ly Tram Ngoc,
Shimoyamada Makoto,
Kato Koji,
Yamauchi Ryo
Publication year - 2004
Publication title -
biofactors
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.204
H-Index - 94
eISSN - 1872-8081
pISSN - 0951-6433
DOI - 10.1002/biof.552210159
Subject(s) - chemistry , rhizome , hydroxymethyl , autoxidation , ether , stereochemistry , alcohol , zingiberaceae , methanol , organic chemistry , medicinal chemistry , botany , biology
Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1–7) were obtained and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, ( E )‐p‐coumaryl alcohol γ‐ O ‐methyl ether (1) and ( E )‐p‐coumaryl alcohol (6); and the five novel compounds, stereoisomers of (4 E )‐1,5‐bis(4‐hydroxy‐phenyl)‐1‐methoxy‐2‐(methoxymethyl)‐4‐pentene (2a and 2b), stereoisomers of (4 E )‐1,5‐bis(4‐hydroxyphenyl)‐1‐ethoxy‐2‐(methoxymethyl)‐4‐pentene (3a and 3b), (4 E )‐1,5‐bis(4‐hydroxy‐phenyl)‐1‐[(2E)‐3‐(4‐acetoxyphenyl)‐2‐propenoxy]‐2‐(methoxymethyl)‐4‐pentene (4), (4 E )‐1,5‐bis(4‐hydroxyphenyl)‐2‐(methoxymethyl)‐4‐penten‐1‐ol (5), and (4 E )‐1,5‐bis(4‐hydroxyphenyl)‐2‐(hydroxymethyl)‐4‐penten‐1‐ol (7). Compounds 1–7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bulk phase.