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

  • Chem Pharm Bull (Tokyo). 2009 Apr;57(4):361-7. doi: 10.1248/cpb.57.361.
Toshio Morikawa  1 ,  Li-Bo Wang ,  Seikou Nakamura ,  Kiyofumi Ninomiya ,  Eri Yokoyama ,  Hisashi Matsuda ,  Osamu Muraoka ,  Li-Jun Wu ,  Masayuki Yoshikawa
Affiliations
  • 1. Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan.
PMID: 19336929 DOI: 10.1248/cpb.57.361
Abstract

The methanolic extract from the flowers of Helichrysum arenarium L. MOENCH was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha, 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-beta-D-glucopyranoside (7), apigenin 7-O-beta-D-glucopyranoside (14), apigenin 7-O-gentiobioside (16), and apigenin 7,4'-di-O-beta-D-glucopyranoside (17) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 microM.

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