New seco-anthraquinone glucoside from the roots of Rumex crispus

A new seco-anthraquinone, crispuside A (1), and three new 3,4-dihydronaphthalen-1(2H)-ones, napthalenones A-C (2-4), were isolated from the roots of Rumex crispus L., along with 10 known anthraquinones (6-14) and naphthalenone (5). Their structures were fully determined by extensive spectroscopic analyses, including ECD, and X-ray crystallography in case of compound 5, whose absolute configuration was determined for the first time. The isolates 1, 6-14 were evaluated for their anti-inflammatory and anti-fungal activity against three skin fungi, e.g., Epidermophyton floccosum, Trichophyton rubrum, and Microsporum gypseum. Most of the isolates showed weak anti-fungal and anti-inflammatory activity. Only compound 9 exhibited obvious anti-fungal activity against E. floccosum (MIC₅₀ = 2.467 ± 0.03 μM) and M. gypseum (MIC₅₀ = 4.673 ± 0.077 μM), while the MIC₅₀ values of the positive control terbinafine were 1.287 ± 0.012 and 0.077 ± 0.00258 μM, respectively. The results indicated that simple emodin type anthraquinone is more potential against skin fungi than its oxyglucosyl, C-glucosyl and glycosylated seco analogues.