A New and Efficient Synthesis of 6-O-Methylscutellarein, the Major Metabolite of the Natural Medicine Scutellarin

被引:8
作者
Zhang, Wei [1 ]
Dong, Ze-Xi [1 ]
Gu, Ting [1 ]
Li, Nian-Guang [1 ]
Zhang, Peng-Xuan [1 ]
Wu, Wen-Yu [1 ]
Yu, Shao-Peng [1 ]
Tang, Yu-Ping [1 ]
Yang, Jian-Ping [1 ]
Shi, Zhi-Hao [2 ]
机构
[1] Nanjing Univ Chinese Med, Natl & Local Collaborat Engn Ctr Chinese Med Reso, Nanjing 210023, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Dept Organ Chem, Nanjing 211198, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
scutellarin; scutellarein; 6-O-methylscutellarein; metabolite; synthesis; NITRIC-OXIDE; IN-VIVO; THROMBIN; DESIGN; 6-O-METHYL-SCUTELLAREIN; ISCHEMIA/REPERFUSION; RATS;
D O I
10.3390/molecules200610184
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this paper, a new and efficient synthesis of 6-O-methylscutellarein (3), the major metabolite of the natural medicine scutellarin, is reported. Two hydroxyl groups at C-4 and C-7 in 2 were selectively protected by chloromethyl methyl ether after the reaction conditions were optimized, then 6-O-methyl-scutellarein (3) was produced in high yield after methylation of the hydroxyl group at C-6 and subsequent deprotection of the two methyl ether groups.
引用
收藏
页码:10184 / 10191
页数:8
相关论文
共 17 条
[1]   Pharmacokinetics and metabolism of the flavonoid scutellarin in humans after a single oral administration [J].
Chen, Xiaoyan ;
Cui, Liang ;
Duan, Xiaotao ;
Ma, Bin ;
Zhong, Dafang .
DRUG METABOLISM AND DISPOSITION, 2006, 34 (08) :1345-1352
[2]  
Cuzzocrea S, 2001, PHARMACOL REV, V53, P135
[3]   Stroke [J].
Donnan, Geoffrey A. ;
Fisher, Marc ;
Macleod, Malcolm ;
Davis, Stephen M. .
LANCET, 2008, 371 (9624) :1612-1623
[4]   Design, synthesis, and thrombin-inhibitory activity of pyridin-2-ones as P2/P3 core motifs [J].
Hanessian, Stephen ;
Simard, Daniel ;
Bayrakdarian, Malken ;
Therrien, Eric ;
Nilsson, Ingemar ;
Fjellstrom, Ola .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (06) :1972-1976
[5]  
Hao XH, 2005, PHARMAZIE, V60, P477
[6]   Scutellarin attenuates oxidative glutamate toxicity in PC12 cells [J].
Hong, H ;
Liu, GQ .
PLANTA MEDICA, 2004, 70 (05) :427-431
[7]   Determination of aglycone conjugated metabolites of scutellarin in rat plasma by HPLC [J].
Huang, JM ;
Li, N ;
Yu, YQ ;
Weng, WY ;
Huang, XB .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2006, 40 (02) :465-471
[8]   Inflammatory mechanisms in ischemic stroke: therapeutic approaches [J].
Lakhan, Shaheen E. ;
Kirchgessner, Annette ;
Hofer, Magdalena .
JOURNAL OF TRANSLATIONAL MEDICINE, 2009, 7
[9]   Inhibition of Thrombin and Factor Xa by Fucus Evanescens Fucoidan and Its Modified Analogs [J].
Lapikova, E. S. ;
Drozd, N. N. ;
Tolstenkov, A. S. ;
Makarov, V. A. ;
Zvyagintseva, T. N. ;
Shevchenko, N. M. ;
Bakunina, I. U. ;
Besednova, N. N. ;
Kuznetsova, T. A. .
BULLETIN OF EXPERIMENTAL BIOLOGY AND MEDICINE, 2008, 146 (03) :328-333
[10]   Design, synthesis and biological evaluation of glucose-containing scutellarein derivatives as neuroprotective agents based on metabolic mechanism of scutellarin in vivo [J].
Li, Nian-Guang ;
Shen, Min-Zhe ;
Wang, Zhen-Jiang ;
Tang, Yu-Ping ;
Shi, Zhi-Hao ;
Fu, Yi-Fan ;
Shi, Qian-Ping ;
Tang, Hao ;
Duan, Jian-Ao .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (01) :102-106