Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium.
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.
Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan, morikawa@kindai.ac.jp.
Toshio
T
Morikawa
Kiyofumi
K
Ninomiya
Junji
J
Akaki
Namiko
N
Kakihara
Hiroyuki
H
Kuramoto
Yurie
Y
Matsumoto
Takao
T
Hayakawa
Osamu
O
Muraoka
Li-Bo
LB
Wang
Li-Jun
LJ
Wu
Seikou
S
Nakamura
Masayuki
M
Yoshikawa
Hisashi
H
Matsuda
D000818:Animals; D047188:Chalcones / Q000737:chemistry*; D004152:Dipeptidyl-Peptidases and Tripeptidyl-Peptidases / Q000737:chemistry*; D035264:Flowers / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D036562:Helichrysum / Q000737:chemistry*; D051379:Mice; D010936:Plant Extracts / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*
D047188:Chalcones; D006027:Glycosides; D010936:Plant Extracts; D004152:Dipeptidyl-Peptidases and Tripeptidyl-Peptidases; C015812:dihydrochalcone