PMID- 27511707
OWN - NLM
STAT- MEDLINE
DCOM- 20170717
LR  - 20240326
IS  - 1582-4934 (Electronic)
IS  - 1582-1838 (Print)
IS  - 1582-1838 (Linking)
VI  - 21
IP  - 1
DP  - 2017 Jan
TI  - Synthesis and cardiovascular protective effects of quercetin 7-O-sialic acid.
PG  - 107-120
LID - 10.1111/jcmm.12943 [doi]
AB  - Oxidative stress and inflammation play important roles in the pathogenesis of 
      cardiovascular disease (CVD). Oxidative stress-induced desialylation is 
      considered to be a primary step in atherogenic modification, and therefore, the 
      attenuation of oxidative stress and/or inflammatory reactions may ameliorate CVD. 
      In this study, quercetin 7-O-sialic acid (QA) was synthesized aiming to put 
      together the cardiovascular protective effect of quercetin and the recently 
      reported anti-oxidant and anti-atherosclerosis functions of N-acetylneuraminic 
      acid. The biological efficacy of QA was evaluated in vitro in various cellular 
      models. The results demonstrated that 50 muM QA could effectively protect human 
      umbilical vein endothelial cells (HUVEC, EA.hy926) against hydrogen peroxide- or 
      oxidized low-density lipoprotein-induced oxidative damage by reducing the 
      production of reactive oxygen species. QA attenuated hydrogen peroxide-induced 
      desialylation of HUVEC and lipoproteins. QA decreased lipopolysaccharide-induced 
      secretion of tumour necrosis factor-alpha (TNF-alpha) and monocyte chemoattractant 
      protein-1 (MCP-1), and it significantly reduced the expression of intercellular 
      adhesion molecule-1, vascular cell adhesion molecule-1, TNF-alpha and MCP-1. 
      Furthermore, QA effectively promoted cholesterol efflux from Raw 264.7 
      macrophages to apolipoprotein A-1 and high-density lipoprotein by up-regulating 
      ATP-binding cassette transporter A1 and G1, respectively. Results indicated that 
      the novel compound QA exhibited a better capacity than quercetin for 
      anti-oxidation, anti-inflammation, cholesterol efflux promotion and biomolecule 
      protection against desialylation and therefore could be a candidate compound for 
      the prevention or treatment of CVD.
CI  - (c) 2016 The Authors. Journal of Cellular and Molecular Medicine published by John 
      Wiley & Sons Ltd and Foundation for Cellular and Molecular Medicine.
FAU - Tian, Hua
AU  - Tian H
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
FAU - Liu, Qingchao
AU  - Liu Q
AD  - Department of Pharmaceutical Engineering, Northwest University, Xi'an, China.
FAU - Qin, Shucun
AU  - Qin S
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
FAU - Zong, Chuanlong
AU  - Zong C
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
FAU - Zhang, Ying
AU  - Zhang Y
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
FAU - Yao, Shutong
AU  - Yao S
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
FAU - Yang, Nana
AU  - Yang N
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
FAU - Guan, Tao
AU  - Guan T
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
FAU - Guo, Shoudong
AU  - Guo S
AD  - Key Laboratory of Atherosclerosis in Universities of Shandong Province, Institute 
      of Atherosclerosis, Taishan Medical University, Taian, China.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20160811
PL  - England
TA  - J Cell Mol Med
JT  - Journal of cellular and molecular medicine
JID - 101083777
RN  - 0 (ATP-Binding Cassette Transporters)
RN  - 0 (Apolipoprotein A-I)
RN  - 0 (Cardiotonic Agents)
RN  - 0 (Chemokine CCL2)
RN  - 0 (Lipoproteins, LDL)
RN  - 0 (Reactive Oxygen Species)
RN  - 0 (Tumor Necrosis Factor-alpha)
RN  - 0 (Vascular Cell Adhesion Molecule-1)
RN  - 0 (oxidized low density lipoprotein)
RN  - 126547-89-5 (Intercellular Adhesion Molecule-1)
RN  - 9IKM0I5T1E (Quercetin)
RN  - GZP2782OP0 (N-Acetylneuraminic Acid)
SB  - IM
MH  - ATP-Binding Cassette Transporters/metabolism
MH  - Animals
MH  - Apolipoprotein A-I/metabolism
MH  - Atherosclerosis/drug therapy/metabolism
MH  - Cardiotonic Agents/*chemistry/*pharmacology
MH  - Cell Line
MH  - Chemokine CCL2/metabolism
MH  - Human Umbilical Vein Endothelial Cells
MH  - Humans
MH  - Inflammation/drug therapy/metabolism
MH  - Intercellular Adhesion Molecule-1/metabolism
MH  - Lipoproteins, LDL/metabolism
MH  - Macrophages/drug effects/metabolism
MH  - Mice
MH  - N-Acetylneuraminic Acid/*chemistry/*pharmacology
MH  - Oxidative Stress/drug effects
MH  - Quercetin/*chemistry/*pharmacology
MH  - Reactive Oxygen Species/metabolism
MH  - Tumor Necrosis Factor-alpha/metabolism
MH  - Vascular Cell Adhesion Molecule-1/metabolism
PMC - PMC5192943
OTO - NOTNLM
OT  - anti-inflammation
OT  - anti-oxidation
OT  - cardiovascular disease
OT  - cholesterol efflux
OT  - quercetin
OT  - sialic acid
EDAT- 2016/08/12 06:00
MHDA- 2017/07/18 06:00
PMCR- 2017/01/01
CRDT- 2016/08/12 06:00
PHST- 2016/01/10 00:00 [received]
PHST- 2016/07/04 00:00 [accepted]
PHST- 2016/08/12 06:00 [pubmed]
PHST- 2017/07/18 06:00 [medline]
PHST- 2016/08/12 06:00 [entrez]
PHST- 2017/01/01 00:00 [pmc-release]
AID - JCMM12943 [pii]
AID - 10.1111/jcmm.12943 [doi]
PST - ppublish
SO  - J Cell Mol Med. 2017 Jan;21(1):107-120. doi: 10.1111/jcmm.12943. Epub 2016 Aug 
      11.