Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium - PubMed (original) (raw)

. 2015 Oct;69(4):494-506.

doi: 10.1007/s11418-015-0914-8. Epub 2015 Apr 29.

Kiyofumi Ninomiya, Junji Akaki, Namiko Kakihara, Hiroyuki Kuramoto, Yurie Matsumoto, Takao Hayakawa, Osamu Muraoka, Li-Bo Wang, Li-Jun Wu, Seikou Nakamura, Masayuki Yoshikawa, Hisashi Matsuda

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Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium

Toshio Morikawa et al. J Nat Med. 2015 Oct.

Abstract

A methanol extract of everlasting flowers of Helichrysum arenarium L. Moench (Asteraceae) was found to inhibit the increase in blood glucose elevation in sucrose-loaded mice at 500 mg/kg p.o. The methanol extract also inhibited the enzymatic activity against dipeptidyl peptidase-IV (DPP-IV, IC50 = 41.2 μg/ml), but did not show intestinal α-glucosidase inhibitory activities. From the extract, three new dimeric dihydrochalcone glycosides, arenariumosides V-VII (2-4), were isolated, and the stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Of the constituents, several flavonoid constituents, including 2-4, were isolated, and these isolated constituents were investigated for their DPP-IV inhibitory effects. Among them, chalconaringenin 2'-O-β-D-glucopyranoside (16, IC50 = 23.1 μM) and aureusidin 6-O-β-D-glucopyranoside (35, 24.3 μM) showed relatively strong inhibitory activities.

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Figures

Fig. 1

Fig. 1

Dimeric dihydrochalcone glycosides (1–4) from the flowers of H. arenarium

Fig. 2

Fig. 2

1H-1H COSY, HMBC, and ROE correlations of 1–4

Fig. 3

Fig. 3

Flavonoids (5–34) from the flowers of H. arenarium

Fig. 4

Fig. 4

Lineweaver-Burk plots of the inhibition of human recombinant DPP-IV activities by 16 and 35

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References

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