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

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  • Morikawa Toshio
    Pharmaceutical Research and Technology Institute, Kinki University
  • Wang Li-Bo
    Kyoto Pharmaceutical University Faculty of Natural Medicines, Shenyang Pharmaceutical University
  • Nakamura Seikou
    Kyoto Pharmaceutical University
  • Ninomiya Kiyofumi
    Pharmaceutical Research and Technology Institute, Kinki University
  • Yokoyama Eri
    Pharmaceutical Research and Technology Institute, Kinki University
  • Matsuda Hisashi
    Kyoto Pharmaceutical University
  • Muraoka Osamu
    Pharmaceutical Research and Technology Institute, Kinki University
  • Wu Li-Jun
    Faculty of Natural Medicines, Shenyang Pharmaceutical University
  • Yoshikawa Masayuki
    Pharmaceutical Research and Technology Institute, Kinki University Kyoto Pharmaceutical University

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  • Medicinal flowers (27) New flavanone and chalcone glycosides, arenariumosides 1, 2, 3, and 4, and tumor necrosis factor-α inhibitors from everlasting, flowers of Helichrysum arenarium
  • Medicinal flowers 27 New flavanone and chalcone glycosides arenariumosides 1 2 3 and 4 and tumor necrosis factor a inhibitors from everlasting flowers of Helichrysum arenarium
  • 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.

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