Dihydrochalcone-derived polyphenols from tea crab apple (Malus hupehensis) and their inhibitory effects on α-glucosidase in vitro

Qiuyue Lv; Yushan Lin; Zhexu Tan; Baoping Jiang; Lijia Xu; Haiqin Ren; William C S Tai; Chi On Chan; Chi Sing Lee; Zhengbing Gu; Daniel K.W. Mok; Sibao Chen

doi:10.1039/c9fo00229d

Dihydrochalcone-derived polyphenols from tea crab apple (Malus hupehensis) and their inhibitory effects on α-glucosidase in vitro

Qiuyue Lv
, Yushan Lin
, Zhexu Tan
, Baoping Jiang
, Lijia Xu
, Haiqin Ren
, William C S Tai
, Chi On Chan
, Chi Sing Lee
, Zhengbing Gu
, Daniel K.W. Mok
, Sibao Chen

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

24 Citations (Scopus)

Abstract

Three dihydrochalcone-derived polyphenols, huperolides A-C (1-3), along with thirteen known compounds (4-16) were isolated from the leaves of Malus hupehensis, the well-known tea crab apple in China. Their chemical structures were elucidated by extensive spectroscopic analysis including NMR (HSQC, HMBC, 1H-1H COSY and ROESY), HRMS and CD spectra. Huperolide A is a polyphenol with a new type of carbon skeleton, while huperolides B and C are a couple of atropisomers, which were isolated from natural sources for the first time. The antihyperglycemic effects of the isolated compounds were evaluated based on assaying their inhibitory activities against α-glucosidase. As a result, phlorizin (4), 3-hydroxyphloridzin (5), 3-O-coumaroylquinic acid (12) and β-hydroxypropiovanillone (15) showed significant concentration-dependent inhibitory effects on α-glucosidase. Therefore, those compounds might be responsible for the antihyperglycemic effect of this herb, and are the most promising compounds to lead discovery of drugs against diabetes.

Original language	English
Pages (from-to)	2881-2887
Number of pages	7
Journal	Food and Function
Volume	10
Issue number	5
DOIs	https://doi.org/10.1039/c9fo00229d
Publication status	Published - May 2019

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@article{34ac7c28373944afab1c65f8905f307e,

title = "Dihydrochalcone-derived polyphenols from tea crab apple (Malus hupehensis) and their inhibitory effects on α-glucosidase in vitro",

abstract = "Three dihydrochalcone-derived polyphenols, huperolides A-C (1-3), along with thirteen known compounds (4-16) were isolated from the leaves of Malus hupehensis, the well-known tea crab apple in China. Their chemical structures were elucidated by extensive spectroscopic analysis including NMR (HSQC, HMBC, 1H-1H COSY and ROESY), HRMS and CD spectra. Huperolide A is a polyphenol with a new type of carbon skeleton, while huperolides B and C are a couple of atropisomers, which were isolated from natural sources for the first time. The antihyperglycemic effects of the isolated compounds were evaluated based on assaying their inhibitory activities against α-glucosidase. As a result, phlorizin (4), 3-hydroxyphloridzin (5), 3-O-coumaroylquinic acid (12) and β-hydroxypropiovanillone (15) showed significant concentration-dependent inhibitory effects on α-glucosidase. Therefore, those compounds might be responsible for the antihyperglycemic effect of this herb, and are the most promising compounds to lead discovery of drugs against diabetes.",

author = "Qiuyue Lv and Yushan Lin and Zhexu Tan and Baoping Jiang and Lijia Xu and Haiqin Ren and Tai, \{William C S\} and Chan, \{Chi On\} and Lee, \{Chi Sing\} and Zhengbing Gu and Mok, \{Daniel K.W.\} and Sibao Chen",

note = "Funding Information: This research work was co-supported financially by the Basic Research Foundation of Shenzhen Science and Technology Innovation Committee (JCYJ20151030164022389, JCYJ20160229173844278) and the National Natural Science Foundation of China (No. 81573576 and 81872769).",

year = "2019",

month = may,

doi = "10.1039/c9fo00229d",

language = "English",

volume = "10",

pages = "2881--2887",

journal = "Food and Function",

issn = "2042-6496",

publisher = "Royal Society of Chemistry",

number = "5",

}

TY - JOUR

T1 - Dihydrochalcone-derived polyphenols from tea crab apple (Malus hupehensis) and their inhibitory effects on α-glucosidase in vitro

AU - Lv, Qiuyue

AU - Lin, Yushan

AU - Tan, Zhexu

AU - Jiang, Baoping

AU - Xu, Lijia

AU - Ren, Haiqin

AU - Tai, William C S

AU - Chan, Chi On

AU - Lee, Chi Sing

AU - Gu, Zhengbing

AU - Mok, Daniel K.W.

AU - Chen, Sibao

N1 - Funding Information: This research work was co-supported financially by the Basic Research Foundation of Shenzhen Science and Technology Innovation Committee (JCYJ20151030164022389, JCYJ20160229173844278) and the National Natural Science Foundation of China (No. 81573576 and 81872769).

PY - 2019/5

Y1 - 2019/5

N2 - Three dihydrochalcone-derived polyphenols, huperolides A-C (1-3), along with thirteen known compounds (4-16) were isolated from the leaves of Malus hupehensis, the well-known tea crab apple in China. Their chemical structures were elucidated by extensive spectroscopic analysis including NMR (HSQC, HMBC, 1H-1H COSY and ROESY), HRMS and CD spectra. Huperolide A is a polyphenol with a new type of carbon skeleton, while huperolides B and C are a couple of atropisomers, which were isolated from natural sources for the first time. The antihyperglycemic effects of the isolated compounds were evaluated based on assaying their inhibitory activities against α-glucosidase. As a result, phlorizin (4), 3-hydroxyphloridzin (5), 3-O-coumaroylquinic acid (12) and β-hydroxypropiovanillone (15) showed significant concentration-dependent inhibitory effects on α-glucosidase. Therefore, those compounds might be responsible for the antihyperglycemic effect of this herb, and are the most promising compounds to lead discovery of drugs against diabetes.

AB - Three dihydrochalcone-derived polyphenols, huperolides A-C (1-3), along with thirteen known compounds (4-16) were isolated from the leaves of Malus hupehensis, the well-known tea crab apple in China. Their chemical structures were elucidated by extensive spectroscopic analysis including NMR (HSQC, HMBC, 1H-1H COSY and ROESY), HRMS and CD spectra. Huperolide A is a polyphenol with a new type of carbon skeleton, while huperolides B and C are a couple of atropisomers, which were isolated from natural sources for the first time. The antihyperglycemic effects of the isolated compounds were evaluated based on assaying their inhibitory activities against α-glucosidase. As a result, phlorizin (4), 3-hydroxyphloridzin (5), 3-O-coumaroylquinic acid (12) and β-hydroxypropiovanillone (15) showed significant concentration-dependent inhibitory effects on α-glucosidase. Therefore, those compounds might be responsible for the antihyperglycemic effect of this herb, and are the most promising compounds to lead discovery of drugs against diabetes.

UR - https://www.scopus.com/pages/publications/85066117309

U2 - 10.1039/c9fo00229d

DO - 10.1039/c9fo00229d

M3 - Journal article

C2 - 31070208

AN - SCOPUS:85066117309

SN - 2042-6496

VL - 10

SP - 2881

EP - 2887

JO - Food and Function

JF - Food and Function

IS - 5

ER -

Dihydrochalcone-derived polyphenols from tea crab apple (Malus hupehensis) and their inhibitory effects on α-glucosidase in vitro

Abstract

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