Identification of new flavonol O-glycosides from indigo (Polygonum tinctorium Lour) leaves and their inhibitory activity against 3-hydroxy-3-methylglutaryl-CoA reductase.
Indigo plant (Polygonum tinctorium Lour) has been utilized as a medicinal plant with a variety of biological activities. We have recently detected higher levels of flavonoids in indigo leaves. This study was undertaken to conduct the simultaneous analysis of those flavonoids using total extracts from indigo leaves by ultra-performance liquid chromatography-electrospray ionization-time-of-flight/mass spectrometry(E) (UPLC-ESI-TOF/MS(E)). The analysis by UPLC-ESI-TOF/MS(E) allowed us to determine 11 peaks of flavonoid species. The chemical structures of these compounds were identified as flavonol O-glycosides with different types of aglycones by the combination of spectroscopic and chemical methods. The predominant compounds were flavonol O-glycosides with 3,5,4'-trihydroxy-6,7-methylenedioxyflavone as an aglycone. Of these, three compounds were elucidated as new compounds. All the isolated flavonol O-glycosides exhibited the inhibitory activity against 3-hydroxy-3-methylglutaryl-CoA reductase in a dose-dependent manner with different potencies. Taken together, our results suggest the potential usefulness of the major flavonol O-glycosides from indigo leaves in controlling cholesterol biosynthesis.
Department of Research and Development, Kotobuki Seika Co., Ltd., 2028 Hatagasaki, Yonago, Tottori 683-0845, Japan.
Hideto
H
Kimura
Department of Research and Development, Kotobuki Seika Co., Ltd., 2028 Hatagasaki, Yonago, Tottori 683-0845, Japan.
Shota
S
Tokuyama
Department of Research and Development, Kotobuki Seika Co., Ltd., 2028 Hatagasaki, Yonago, Tottori 683-0845, Japan.
Tomoe
T
Ishihara
Department of Research and Development, Kotobuki Seika Co., Ltd., 2028 Hatagasaki, Yonago, Tottori 683-0845, Japan.
Satoshi
S
Ogawa
Department of Life Science and Biotechnology, Faculty of Life and Environmental Science, Shimane University, 1060 Nishikawatsu-cho, Matsue, Shimane 690-8504, Japan; The United Graduate School of Agricultural Sciences, Tottori University, 4-101 Koyama-minami, Tottori-shi, Tottori 680-8553, Japan. Electronic address: yokotaka@life.shimane-u.ac.jp.
Kazushige
K
Yokota
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004305:Dose-Response Relationship, Drug; D044948:Flavonols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves; D028502:Polygonum / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods
D044948:Flavonols; D006027:Glycosides; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; D010936:Plant Extracts
3,5,4′-Trihydroxy-6,7-methylenedioxyflavone; 3-Hydroxy-3-methylglutaryl-CoA reductase; Flavonol O-glycosides; Polygonum tinctorium Lour; UPLC–ESI-TOF/MS(E)