New seco-anthraquinone glucoside from the roots of Rumex crispus

Abstract A new seco-anthraquinone, crispuside A ( 1 ), and three new 3,4-dihydronaphthalen-1(2 H )-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 (MIC 50 = 2.467 ± 0.03 μM) and M. gypseum (MIC 50 = 4.673 ± 0.077 μM), while the MIC 50 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. Graphical Abstract

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