PMID- 36055425
OWN - NLM
STAT- Publisher
LR  - 20231019
IS  - 1873-3700 (Electronic)
IS  - 0031-9422 (Linking)
VI  - 204
DP  - 2022 Dec
TI  - alpha-Glucosidase inhibitory phenylpropanoid-dihydrochalcone hybrids from the leaves 
      of medicinal plant Malus hupehensis (Pamp.) Rehder.
PG  - 113421
LID - S0031-9422(22)00337-5 [pii]
LID - 10.1016/j.phytochem.2022.113421 [doi]
AB  - Eight undescribed phenylpropanoid-dihydrochalcone hybrids, namely (+)- and 
      (-)-malahupin A, (+)- and (-)-malahupin B, (+/-)-malahupin C, malahupinosides A and 
      B, 7'''-epi-malahupinoside B, together with two known compounds, phloretin and 
      phlorizin, were isolated from the leaves of the folk medicinal plant Malus 
      hupehensis. Their structures were elucidated by extensive NMR and MS 
      spectroscopic methods, chiral-phase analysis, and ECD calculations. Compounds 
      (+)-malahupin B and malahupinoside B showed weak inhibition activities against 
      the nitric oxide production in liposaccharide-induced murine RAW264.7 macrophages 
      with IC(50) values of 36.7 and 27.0 muM, respectively. Compounds (+)- and 
      (-)-malahupin A, (+)- and (-)-malahupin B exhibited significant alpha-glucosidase 
      inhibitory activity, with IC(50) values of 22.5, 19.1, 19.2, and 17.4 muM, 
      respectively. The postulated biosynthetic pathways to these hybrid compounds were 
      proposed. This work represents the first report of the natural 
      phenylpropanoid-dihydrochalcone hybrid compound, and lays foundation for the 
      study on the bioactive principles of the ethnic hypoglycemic medicinal plant.
CI  - Copyright (c) 2022 Elsevier Ltd. All rights reserved.
FAU - Yuan, Lin-Lin
AU  - Yuan LL
AD  - School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, 
      China.
FAU - Shi, Bao-Bao
AU  - Shi BB
AD  - School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, 
      China.
FAU - Feng, Tao
AU  - Feng T
AD  - School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, 
      China.
FAU - Huang, Rong
AU  - Huang R
AD  - School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, 
      China.
FAU - Li, Zheng-Hui
AU  - Li ZH
AD  - School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, 
      China.
FAU - Chen, He-Ping
AU  - Chen HP
AD  - School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, 
      China. Electronic address: chenhp@mail.scuec.edu.cn.
FAU - Liu, Ji-Kai
AU  - Liu JK
AD  - School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, 
      China. Electronic address: liujikai@mail.scuec.edu.cn.
LA  - eng
PT  - Journal Article
DEP - 20220831
PL  - England
TA  - Phytochemistry
JT  - Phytochemistry
JID - 0151434
SB  - IM
OTO - NOTNLM
OT  - Dihydrochalcone
OT  - ECD calculation
OT  - Hupeh crabapple
OT  - Malus hupehensis (Pamp.) Rehder
OT  - Phenylpropanoid
OT  - Rosaceae
OT  - Specialised compounds
OT  - alpha-Glucosidase inhibitory activity
COIS- Declaration of competing interest The authors declare that they have no known 
      competing financial interests or personal relationships that could have appeared 
      to influence the work reported in this paper.
EDAT- 2022/09/03 06:00
MHDA- 2022/09/03 06:00
CRDT- 2022/09/02 19:24
PHST- 2022/05/23 00:00 [received]
PHST- 2022/07/31 00:00 [revised]
PHST- 2022/08/26 00:00 [accepted]
PHST- 2022/09/03 06:00 [pubmed]
PHST- 2022/09/03 06:00 [medline]
PHST- 2022/09/02 19:24 [entrez]
AID - S0031-9422(22)00337-5 [pii]
AID - 10.1016/j.phytochem.2022.113421 [doi]
PST - ppublish
SO  - Phytochemistry. 2022 Dec;204:113421. doi: 10.1016/j.phytochem.2022.113421. Epub 
      2022 Aug 31.