Medicinal Flowers. XXVII. New Flavanone and Chalcone Glycosides, Arenariumosides I, II, III, and IV, and Tumor Necrosis Factor-α Inhibitors from Everlasting, Flowers of Helichrysum arenarium

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The methanolic extract from the flowers of Helichrysum arenarium L. MOENCH was found to show inhibitory effect on tumor necrosis factor-α (TNF-α, 1 ng/ml)-induced cytotoxicity in L929 cells. From the methanolic extract, 50 constituents including four new flavanone and chalcone glycosides named arenariumosides I (1), II (2), III (3), and IV (4) were isolated. The stereostructures of 1—4 were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, naringenin 7-O-β-D-glucopyranoside (7), apigenin 7-O-β-D-glucopyranoside (14), apigenin 7-O-gentiobioside (16), and apigenin 7,4′-di-O-β-D-glucopyranoside (17) significantly inhibited TNF-α-induced cytotoxicity in L929 cells at 30 μM.