Isolation of novel glucosides related to gingerdiol from ginger and their antioxidative activities.
Two novel glucosides of 6-gingerdiol were isolated from fresh ginger (Zingiber officinale Roscoe). Their structures were determined as 1-(4-O-beta-D-glucopyranosyl-3-methoxyphenyl)-3,5-dihydroxydecane (1) and 5-O-beta-D-glucopyranosyl-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca ne (2) by HRFAB-MS and NMR analyses, and the absolute configurations of both aglycons were identified as (3S,5S) by a comparison with synthetic compounds. After incubating these glucosides with acetone powder prepared from fresh ginger, they were confirmed to have been hydrolyzed to 6-gingerdiol by HPLC. This result suggests that these glucosides are the precursors or intermediates of 6-gingerdiol. To recognize their function, their antioxidative activities were investigated and compared to that of their aglycon, 6-gingerdiol, by a linoleic acid model system and by their DPPH radical-scavenging ability. Although 1 did not indicate any activity, 2 had as strong activity as the aglycon in both measurements.
Sekiwa
Y
Y
Graduate School of Humanities and Sciences, Laboratory of Food Chemistry, Department of Nutrition and Food Science, Ochanomizu University, 2-1-1 Ohtsuka, Bunkyo-ku, Tokyo 112-8610, Japan. sekiwa@cc.ocha.ac.jp
Kubota
K
K
Kobayashi
A
A
D000096:Acetone; D000975:Antioxidants / Q000302:isolation & purification*; D002396:Catechols; D005233:Fatty Alcohols / Q000737:chemistry*; D005609:Free Radicals; D020939:Zingiber officinale / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification*; D019787:Linoleic Acid / Q000032:analysis; D010946:Plants, Medicinal
C406686:1-(4-O-glucopyranosyl-3-methoxyphenyl)-3,5-dihydroxydecane; C406687:5-O-glucopyranosyl-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane; D000975:Antioxidants; D002396:Catechols; D005233:Fatty Alcohols; D005609:Free Radicals; D005960:Glucosides; D000096:Acetone; C007845:gingerol; D019787:Linoleic Acid