CAS: 22688-79-5; (2S,3S,4S,5R,6S)-6-((2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-4-Oxo-4H-Chromen-3-yl)Oxy)-3,4,5-Trihydroxytetrahydro-2H-Pyran-2-Carboxylic Acid

该化合物是一个裂变胶质的胶质,来源于quercetin 与 luclocial 酸的混凝土.这种水溶性代谢物比其 aglycone 的对应物更能提高生物利用率,使它成为研究营养学和药理学的宝贵化合物.其结构改善了生物系统的稳定性和吸收能力.研究显示,由于它能够调节细胞信号路径,它具有潜在的抗氧化剂,抗氟化物和心肺保护特性. 浮化物运动还影响其药用基因特征,包括组织分布和排泄物.该化合物有助于调查氟化物代谢,生物利用率和氧化性压力相关条件下的治疗应用.

结构式图片

上下游产品

quercetol 7,4'-di-O-benzylquercetin 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-oneD-glucuronic acid quercetol D-glucuronic acid

合成工艺路线路线简述

    在 20 % Pd(Oh)2/c,氢气体系中,用 四氢呋喃,乙醇 用作溶剂,化学反应 12.0H,以16 Mg的收率获得2-(3,4二羟基苯基)-5,7-二羟基-4-氧代-4H-1-苯并吡喃-3-基-Beta-D-吡喃葡糖苷酸
    参考文献:Regiospecific Synthesis Of Quercetin O-β-D-Glucosylated And O-β-D-Glucuronidated Isomers
    标题:Regiospecific Synthesis Of Quercetin O-β-D-Glucosylated And O-β-D-Glucuronidated Isomers
    摘要:Quercetin,The Polyphenolic Compound,Which Has The Highest Daily Intake,Is Well Known For Its Protective Effects Against Aging Diseases And Has Received A Lot Of Attention For This Reason. Both Quercetin 3-O-Beta-D-Glucuronide And Quercetin 3'-O-Beta-D-Glucuronide Are Human Metabolites,Which,Together With Their Regioisomers,Are Required For Biological As Well As Physical Chemistry Studies. We Present Here A Novel Synthetic Route Based On The Sequential And Selective Protections Of The Hydroxyl Functions Of Quercetin Allowing Selective Glycosylation,Followed By Tempo-Mediated Oxidation To The Glucuronide. This Methodology Enabled Us To Synthesize The Five O-Beta-D-Glucosides And Four O-Beta-D-Glucuronides Of Quercetin,Including The Major Human Metabolite,Quercetin 3-O-Beta-D-Glucuronide. (C) 2011 Published By Elsevier Ltd.
    Doi:10.1016/j.Tet.2011.03.110

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    主要参考文献


    1: Juergenliemk G, Boje K, Huewel S, Lohmann C, Galla HJ, Nahrstedt A. In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta Med. 2003 Nov;69(11):1013-7. doi: 10.1055/a-0581-5286. Epub 2018 Mar 2. doi: 10.1128/mBio.00058-16.
    4: Yuan Z, Luan G, Wang Z, Hao X, Li J, Suo Y, Li G, Wang H. Flavonoids from Potentilla parvifolia Fisch. and Their Neuroprotective Effects in Human Neuroblastoma SH-SY5Y Cells in vitro. Chem Biodivers. 2017 Jun;14(6). doi: 10.1002/cbdv.201600487. Epub 2017 Apr 25. Epub 2016 Sep 2. doi: 10.1016/j.jep.2015.02.013. Epub 2015 Feb 12. doi: 10.1111/1750-3841.13329. Epub 2016 May 13. doi: 10.1016/j.phytochem.2013.10.011. Epub 2013 Nov 17. doi: 10.1080/14786419.2013.843179. Epub 2013 Oct 2. pii: E1193. doi: 10.3390/nu9111193.
    13: Jiang S, Liu Q, Xie Y, Zeng H, Zhang L, Jiang X, Chen X. Separation of five flavonoids from tartary buckwheat (Fagopyrum tataricum (L.) Gaertn) grains via off-line two dimensional high-speed counter-current chromatography. Food Chem. 2015 Nov 1;186:153-9. doi: 10.1016/j.foodchem.2014.08.120. Epub 2014 Sep 9. doi: 10.3390/molecules18033050. doi: 10.1007/s00240-014-0720-x. Epub 2014 Sep 17. doi: 10.1016/j.bbrc.2012.09.080. Epub 2012 Sep 20. doi: 10.1080/14786419.2014.915829. Epub 2014 May 13. doi: 10.1080/14786419.2013.856903. Epub 2013 Nov 29. doi: 10.1016/j.biortech.2011.08.029. Epub 2011 Aug 11. doi: 10.1080/14786419.2011.582468. Epub 2011 Nov 11.

    合成参考文献


    参考文献:10.4268/cjcmm20110417
    摘要:Li Y, Li C, He X, Liao S, Lan Y, Wang A, Wang Y. [Chemical constituents in herb of Polygonum orientale II]. Zhongguo Zhong Yao Za Zhi. 2011 Feb;36(4):458–61.
    参考文献:10.1155/2014/580626
    摘要:Chan ST, Lin YC, Chuang CH, Shiau RJ, Liao JW, Yeh SL. Oral and intraperitoneal administration of quercetin decreased lymphocyte DNA damage and plasma lipid peroxidation induced by TSA in vivo. Biomed Res Int. 2014;2014():580626.
    参考文献:10.3390/molecules23051042
    摘要:Liu Y, Cao Y, Fang S, Wang T, Yin Z, Shang X, Yang W, Fu X. Antidiabetic Effect of Cyclocarya paliurus Leaves Depends on the Contents of Antihyperglycemic Flavonoids and Antihyperlipidemic Triterpenoids. Molecules. 2018 Apr 29;23(5):1042. doi: 10.3390/molecules23051042.
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