18α-甘草酸及其酯的合成与抗病毒活性
Synthesis and antiviral activity of 18α-glycyrrhizic acid and its esters.
作者信息
Baltina L A, Stolyarova O V, Baltina L A, Kondratenko R M, Plyasunova O A, Pokrovskii A G
机构信息
1Bashkir State Medical University, Ufa, Russia.
2Institute of Organic Chemistry, Ufa Scientific Centre, Russian Academy of Sciences, Ufa, Russia.
出版信息
Pharm Chem J. 2010;44(6):299-302. doi: 10.1007/s11094-010-0454-1. Epub 2010 Oct 27.
Abstract
New esters (sulfate, nicotinates, and 4-methoxycinnamate) of 18α-glycyrrhizic acid (18α-GA) were synthesized; these were D/E--isomers of natural 18β-GA (GA), which is the major triterpene glycoside in the roots of Spanish licorice and Urals licorice ( L. and Fisher). Changes in the stereochemistry of the GA aglycone led to significant decreases in its anti-HIV-1 activity.
摘要
合成了18α-甘草酸（18α-GA）的新酯（硫酸盐、烟酸盐和4-甲氧基肉桂酸酯）；这些是天然18β-甘草酸（GA）的D/E-异构体，GA是西班牙甘草和乌拉尔甘草（L.和Fisher）根中的主要三萜糖苷。GA苷元立体化学的变化导致其抗HIV-1活性显著降低。
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本文引用的文献
1
[The anti-HIV activity of glycyrrhizic acid penta-O-nicotinate].甘草酸五 - O - 烟酸盐的抗HIV活性
Vestn Ross Akad Med Nauk. 2004(11):42-6.
2
Mechanism of action of glycyrrhizic acid in inhibition of Epstein-Barr virus replication in vitro.甘草酸体外抑制EB病毒复制的作用机制
Antiviral Res. 2003 Jun;59(1):41-7. doi: 10.1016/s0166-3542(03)00030-5.
3
Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus.甘草甜素，甘草根的一种活性成分，与严重急性呼吸综合征相关冠状病毒的复制
Lancet. 2003 Jun 14;361(9374):2045-6. doi: 10.1016/s0140-6736(03)13615-x.
4
Hepatoprotective drugs for the treatment of virus-induced chronic hepatitis: from hypercarcinogenic state to hypocarcinogenic state.用于治疗病毒诱导的慢性肝炎的保肝药物：从高致癌状态到低致癌状态
Jpn J Pharmacol. 2001 Nov;87(3):177-80. doi: 10.1254/jjp.87.177.
5
A drug over the millennia: pharmacognosy, chemistry, and pharmacology of licorice.跨越千年的药物：甘草的生药学、化学与药理学
Yakugaku Zasshi. 2000 Oct;120(10):849-62. doi: 10.1248/yakushi1947.120.10_849.
6
[Glycyrrhizic acid].[甘草酸]
Bioorg Khim. 1997 Sep;23(9):691-709.
7
The long term efficacy of glycyrrhizin in chronic hepatitis C patients.甘草酸在慢性丙型肝炎患者中的长期疗效。
Cancer. 1997 Apr 15;79(8):1494-500. doi: 10.1002/(sici)1097-0142(19970415)79:8<1494::aid-cncr8>3.0.co;2-b.
8
Therapeutic basis of glycyrrhizin on chronic hepatitis B.甘草酸治疗慢性乙型肝炎的基础
Antiviral Res. 1996 May;30(2-3):171-7. doi: 10.1016/0166-3542(96)00942-4.
9
Effect of glycyrrhizin, cyclosporin A, and tumor necrosis factor alpha on infection of U-937 and MRC-5 cells by human cytomegalovirus.
J Leukoc Biol. 1994 Jan;55(1):24-8. doi: 10.1002/jlb.55.1.24.
10
Studies on mechanism of action of glycyrrhizin against hepatitis A virus replication in vitro.
Antiviral Res. 1994 Jan;23(1):63-76. doi: 10.1016/0166-3542(94)90033-7.
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