Isolation and Characterization of Some Antioxidative Compounds from the Rhizomes of Smaller Galanga (Alpinia officinarum Hance)

• Published in: Journal of agricultural and food chemistry Vol. 51; no. 17; pp. 4924 - 4929
• Main Authors: Ly, Tram Ngoc, Shimoyamada, Makoto, Kato, Koji, Yamauchi, Ryo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 13.08.2003; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Alkenes - chemistry; Alkenes - isolation & purification; Alkenes - pharmacology; Alpinia - chemistry; Alpinia officinarum; antioxidant activity; Antioxidants - chemistry; Antioxidants - isolation & purification; Antioxidants - pharmacology; autoxidation; Chemistry; Chemistry, Applied; Chromatography, High Pressure Liquid; Food Science & Technology; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Mass Spectrometry; methanol; Molecular Structure; nuclear magnetic resonance spectroscopy; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; phenylpropanoids; Physical Sciences; Plant Extracts - chemistry; reversed-phase high performance liquid chromatography; Rhizome - chemistry; rhizomes; Science & Technology; stereoisomers; phenylpropanoid; p-coumaryl alcohol; antioxidant; Alpinia officinarum Hance; AUTOXIDATION; CURCUMINOIDS; ALCOHOL; GINGER; EXTRACTS; p-coumaryl methyl ether; galanga; METHYL LINOLEATE; Zingiberaceae
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf034295m

Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1−7) were finally obtained by reversed-phase HPLC, 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 (4E)-1,5-bis(4-hydroxyphenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxyphenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-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. Keywords: Antioxidant; phenylpropanoid; p-coumaryl alcohol; p-coumaryl methyl ether; galanga; Alpinia officinarum Hance; Zingiberaceae