Hyperdioxanes, dibenzo-1,4-dioxane derivatives from the roots of Hypericum ascyron.
Six dibenzo-1,4-dioxane derivatives (1-6) were isolated from the roots of a Hypericaceous plant Hypericum ascyron. Spectroscopic analyses revealed 2 and 4-6 to be new compounds. The partial racemic natures of 1-3 were concluded by chiral HPLC analyses, while 5 was confirmed to be a racemate. The absolute configurations 1-4 were deduced on the basis of ECD calculations. Biological activity evaluation of the dibenzo-1,4-dioxane derivatives along with two related compounds: hyperdioxanes A (7) and B (8), previously isolated from the same plant material by our group demonstrated that 7 exhibit an anti-HIV activity (IC50 5.3 μM, TI 7.2) while 8 showed an inhibitory effect on IL-1β production (inhibition rate: 72.3% at 6.3 μM) from LPS-stimulated microglial cells.
Niwa, Kanji, Naonobu Tanaka, Yusei Shimomoto, Daisuke Tsuji, Sang-Yong Kim, Mareshige Kojoma, Kohji Itoh, Chin-Ho Chen, Kuo-Hsiung Lee, and Yoshiki Kashiwada. “Hyperdioxanes, dibenzo-1,4-dioxane derivatives from the roots of Hypericum ascyron.” J Nat Med 75, no. 4 (September 2021): 907–14. https://doi.org/10.1007/s11418-021-01540-y.