Abstract
We have previously found two novel monoterpene glycosides, liguroside A and liguroside B, with an inhibitory effect on the catalytic activity of the enzyme leukocyte-type 12-lipoxygenase in the Qing Shan Lu Shui tea. Here, two new monoterpene glycosides, liguroside C and liguroside D which inhibit this enzyme, were isolated from the same tea. The spectral and chemical evidence characterized the structures of these compounds as (5E)-7-hydroperoxy-3,7-dimethyl-1,5-octadienyl-3-O-(α-l-rhamnopyranosyl)-(1′′→3′)-(4′′′-O-trans-p-coumaroyl)-β-d-glucopyranoside and (2E)-6-hydroxy-3,7-dimethyl-2,7-octadienyl-3-O-(α-l-rhamnopyranosyl)-(1′′→3′)-(4′′′-O-trans-p-coumaroyl)-β-d-glucopyranoside, respectively. These ligurosides, which irreversibly inhibited leukocyte-type 12-lipoxygenase, have a hydroperoxy group in the monoterpene moiety. Additionally, monoterpene glycosides had the same backbone structure but did not have a hydroperoxy group, such as kudingoside A and lipedoside B-III, contained in the tea did not inhibit the enzyme. When a hydroperoxy group in liguroside A was reduced by using triphenylphosphine, the resultant compound, kudingoside B, showed a lower inhibitory effect on the enzyme. These results strongly suggest the involvement of the hydroperoxy group in the irreversible inhibition of the catalytic activity of leukocyte-type 12-lipoxygenase by the monoterpene glycosides contained in the Qing Shan Lu Shui tea.
Highlights
Qing Shan Lu Shui which is a kind of Kuding tea, is made by processing the leaves of Ligustrum robustum (Roxb.) Blume
Qing Shan Lu Shui tea is consumed in some parts of China, for healthhealth-benefits; it shows various pharmacological effects, as anti-inflammatory, antioxidative, benefits; it shows various pharmacological effects, such such as anti-inflammatory, antioxidative, and and antiproliferative activities previous report has demonstrated that aqueous extracts of the antiproliferative activities [2,3,4,5,6]
We have reported that the inhibitors from the Qing Shan Lu Shui irreversibly leukocyte-type inhibit the catalytic activity of leukocyte-type 12-lipoxygenase
Summary
Qing Shan Lu Shui which is a kind of Kuding tea, is made by processing the leaves of Ligustrum robustum (Roxb.) Blume. Qing Shan Lu Shui which is a kind of Kuding tea, is made by processing the leaves of Ligustrum robustum (Roxb.). A previous report has demonstrated that aqueous extracts of the antiproliferative activities [2,3,4,5,6]. B, inhibited the catalytic activity of that two novel monoterpene glycosides, liguroside A and liguroside B, inhibited the catalytic activity leukocyte-type. Our previous report demonstrated that guava leaf extracts inhibited the development of atherosclerosis [8,9]. Our previous report demonstrated that guava leaf extracts leukocyte-type. We have reported that the inhibitors from the Qing Shan Lu Shui irreversibly leukocyte-type.
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