Structure–Antiamnesic Activity Relationship of Iridoid Glycosides from Gardenia Fruits
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We investigated the in vitro inhibitory acetylcholinesterase (AChE) activities and in vivo ameliorating effects on scopolamine-induced memory impairment of nine iridoid glycosides, namely, geniposide (<b>1</b>), genipin gentiobioside (<b>2</b>), gardenoside (<b>3</b>), scandoside methyl ester (<b>4</b>), deacetylasperulosidic acid methyl ester (<b>5</b>), 6-<i>O</i>-methyldeacetylasperulosidic acid methyl ester (<b>6</b>), geniposidic acid (<b>7</b>), gardoside (<b>8</b>), and shanzhiside (<b>9</b>), isolated from the fruits of <i>Gardenia jasminoides</i> (edible gardenia). Contrary to preliminary studies, genipin gentiobioside (<b>2</b>) exhibited the greatest anti-AChE activity (60.23 ± 2.12%) and antiamnesic effects (ca. 2-fold enhancement vs. the untreated control) using a passive avoidance task system, which is comparable to tacrine. Structure–activity relationships are suggested, which would be useful for identifying candidate compounds for the treatment of memory dysfunction.
- Chemistry Letters
Chemistry Letters 44(6), 837-839, 2015
The Chemical Society of Japan