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

Toshio Morikawa; Li-Bo Wang; Seikou Nakamura; Kiyofumi Ninomiya; Eri Yokoyama; Hisashi Matsuda; Osamu Muraoka; Li-Jun Wu; Masayuki Yoshikawa

doi:10.1248/cpb.57.361

Regular Articles

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

Toshio Morikawa, Li-Bo Wang, Seikou Nakamura, Kiyofumi Ninomiya, Eri Yokoyama, Hisashi Matsuda, Osamu Muraoka, Li-Jun Wu, Masayuki Yoshikawa

Author information

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

Keywords: Helichrysum arenarium, arenariumoside, medicinal flower, tumor necrosis factor-α inhibitory activity, Asteraceae, everlasting

JOURNAL FREE ACCESS

2009 Volume 57 Issue 4 Pages 361-367

DOI https://doi.org/10.1248/cpb.57.361

Details

Abstract

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.

Corresponding author

Register with J-STAGE for free!