Abstract
Two rare sulphate ellagic acid derivatives were isolated from the rhizome of Geum rivale L. in three simple steps. Their structures were identified by comprehensive NMR studies (1H NMR, 13C NMR, 1H-1H COSY, HMBC, HSQC) as 3,3′-dimethoxy-4-sulphoxyellagic acid potassium salt (1) and 3,3′,4′-trimethoxy-4-sulphoxyellagic acid potassium salt (2). Subsequently, a new precise (RSD < 2.6%), accurate (recoveries in the range of 96.5–98.7%), and sensitive (LODs in the range of 0.15–0.16 μg/mL) HPLC-PDA procedure was developed for the simultaneous quantification of compounds 1 and 2 in plant material. The rhizome of G. rivale proved to be a good source of both compounds, with the content of 2.94 ± 0.03 and 5.45 ± 0.03 mg/g dw respectively, whereas at most, trace amounts were detected in related plant materials (aerial parts of G. rivale, rhizome and aerial parts of G. urbanum). The cytotoxicity of isolated compounds tested on human leukaemia (promyelocytic HL-60 and lymphoblastic NALM-6) and melanoma (WM 115) cell lines with IC50 values in the range of 306.4–473.8 μM was demonstrated to be lower than that of ellagic acid (IC50 = 62.3–300.6 μM).
Highlights
IntroductionGeum rivale L. (water avens, purple avens) is an herbaceous plant of Rosaceae family that is widespread in the regions of temperate climate of northern hemisphere [1]
Geum rivale L. is an herbaceous plant of Rosaceae family that is widespread in the regions of temperate climate of northern hemisphere [1]
Compound 1 has previously only been isolated from Tamarix tetragyna and Euphorbia sororia, whereas compound 2 has previously been isolated from the latter species and Potentilla candicans [9,10,13]
Summary
Geum rivale L. (water avens, purple avens) is an herbaceous plant of Rosaceae family that is widespread in the regions of temperate climate of northern hemisphere [1]. The authors of this paper demonstrated that the rhizome of G. rivale is rich source of ellagic acid (60.6 mg/g dry weight (dw) of the plant material), found mainly in a bound form [6]. It has been broadly studied due to its strong antioxidant and chemopreventive potential and was demonstrated to have a variety of other biological effects, e.g., cytotoxic, antimicrobial, and anti-inflammatory activities [7]. It is formed in plants from hexahydroxydiphenic acid—a product of oxidative dimerization of two vicinal galloyl moieties in gallotannin molecules—and accumulated in a free form or transformed further
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