Insights into the Phytochemical Composition and Bioactivities of Seeds from Wild Peony Species

Peony is an important medicinal and ornamental plant widely cultivated in the world. Its seeds as a functional food source have attracted much more attention in recent years, and they are rich in monoterpene glycosides and phenolic compounds. To assess the application value of wild peony seeds, the main chemical composition and content, such as total phenolic content (TPC), total flavonoid content (TFC), total flavanol content (TAC), and α and γ tocopherol content, of the seeds from 12 species and 2 subspecies were systematically explored in the present study. Four different antioxidant assays (DPPH, ABTS, FRAP, and HRSA), antibacterial, and antifungal assays were also performed using various in vitro biochemical methods. The results showed that the seeds of P. delavayi, P. obovata. subsp. obovata, and P. rockii. subsp. rockii had a high content of TPC, TFC, and TAC, respectively. Twenty-five individual chemical compounds were qualitatively and quantitatively measured by HPLC-MS, with paeoniflorin being the most abundant compound in all samples. P. mairei was grouped individually into a group via hierarchical cluster analysis according to its relatively highest monoterpene glycosides and TPC content. This work has provided a basis for the development and utilization of seeds for the selection of wild peony species of dietary interest.

Involvement of the Hydroperoxy Group in the Irreversible Inhibition of Leukocyte-Type 12-Lipoxygenase by Monoterpene Glycosides Contained in the Qing Shan Lu Shui Tea

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.