[1]彭 仁,姚清文,洪彬文.澳栗精胺衍生物的酶法合成研究[J].江西师范大学学报(自然科学版),2017,(06):574-578.
 PENG Ren,YAO Qingwen,HONG Binwen.The Enzymatic Synthesis of Castanospermine Derivatives[J].Journal of Jiangxi Normal University:Natural Science Edition,2017,(06):574-578.
点击复制

澳栗精胺衍生物的酶法合成研究()
分享到:

《江西师范大学学报》(自然科学版)[ISSN:1006-6977/CN:61-1281/TN]

卷:
期数:
2017年06期
页码:
574-578
栏目:
出版日期:
2017-12-01

文章信息/Info

Title:
The Enzymatic Synthesis of Castanospermine Derivatives
作者:
彭 仁姚清文洪彬文
江西师范大学生命科学学院,江西 南昌 330022
Author(s):
PENG RenYAO QingwenHONG Binwen
College of Life Science,Jiangxi Normal University,Nanchang Jiangxi 330022,China
关键词:
澳栗精胺衍生物 脂肪酶 酶法合成 高压液相色谱
Keywords:
castanospermine derivatives lipase enzymatic synthesis HPLC
分类号:
Q 814.9
文献标志码:
A
摘要:
澳栗精胺具有调节植物生长、抗炎症病变、免疫抑制缺陷和肿瘤转移等方面的功能,澳栗精胺的一些衍生物在抑制人类免疫缺陷病毒和丙肝病毒等方面比澳栗精胺本身活性更高.该文系统地优化了在有机溶剂中酶法合成澳栗精胺衍生物的条件,并且纯化得到了6-O-丁酰澳栗精胺.结果表明:合成澳栗精胺衍生物的最优条件为Lipozyme RM IM在四氢呋喃中、30 ℃下催化反应60 min,其中澳栗精胺的转化率为84.3%,6-O-丁酰澳栗精胺的得率为39.2%.纯化得到的6-O-丁酰澳栗精胺与标准品在高压液相色谱中的保留时间相同.
Abstract:
Castanospermine holds potential in the regulation of plant growth and the treatment of inflammatory disorder,viral infection,immunosuppressive deficiency and tumor metastasis.Some derivatives of castanospermine are more active than castanospermine itself in the inhibition of HIV and HCV.Enzymatic synthesis of castanospermine derivatives in organic solvent is studied by systematic trials of various parameters and 6-O-butanoyl castanospermine is purified.The synthesis of castanospermine derivatives by Lipozyme RM IM at 30 ℃ for 60 min in THF gives the best conditions,in which conversion rate of castanospermine is 84.3% and yield rate of 6-O-butanoyl castanospermine is 39.2%.The purified 6-O-butanoyl castanospermine has the same retention time as the standard in HPLC.

参考文献/References:

[1] Hohenschutz L D,Liza D,Bell E A,et al.Castanospermine,A 1,6,7,8-tetrahydroxyoctahydroindolizine alkaloid,from seeds of Castanospermum australe [J].Phytochemistry,1981,20(6):811-814.
[2] Stevens K L,Molyneux R J.Castanospermine:a plant growth regulator [J].J Chem Ecol,1988,14(6):1467-1473.
[3] Hong Yupu,Chen Chen,Guo Wenyi,et al.Effects of castanospermine on inflammatory response in a rat model of experimental severe acute pancreatitis [J].Arch Med Res,2016,47(6):436-445.
[4] Chang Jinhong,Guo Jutao,Du Yanming,et al.Imino sugar glucosidase inhibitors as broadly active anti-filovirus agents [J].Emerg Microbes Infect,2013,2(e77):1-7.
[5] Chang Jinhong,Block T M,Guo Jutao.Antiviral therapies targeting host ER alpha- glucosidases:current status and future directions [J].Antiviral Res,2013,99(3):251-260.
[6] Hibberd A D,Trevillian P R,Clark D A,et al.The effects of Castanospermine,an oligosaccharide processing inhibitor,on mononuclear/endothelial cell binding and the expression of cell adhesion molecules [J].Transpl Immunol,2012,27(1):39-47.
[7] Yee C S,Schwab E D,Lehr J E,et al.The effect of castanospermine on the metastatic properties of prostate cancer cells [J].Anticancer Res,1997,17(5A):3659 -3663.
[8] Delinck D L,Margolin A L.Enzyme-catalyzed acylation of castanospermine and 1-deoxynojirimycin [J].Tetrahedron Lett,1990,31(22):3093-3096.
[9] Taylor D L,Sunkara P S,Liu P S,et al.6-O-butanoylcastanospermine(MDL 28,574)inhibits glycoprotein processing and the growth of HIVs [J].AIDS,1991,5(6):693-698.
[10] Taylor D L,Kang M S,Brennan T M,et al.Inhibition of alpha-glucosidase I of the glycoprotein-processing enzymes by 6-O-butanoyl castanospermine(MDL 28,574)and its consequences in human immunodeficiency virus-infected T cells [J].Antimicrob Agents Chemother,1994,38(8):1780-1787.
[11] Whitby K,Pierson T C,Geiss B,et al.Castanospermine,a potent inhibitor of dengue virus infection in vitro and in vivo [J].J Virol,2005,79(14):8698-8706.
[12] Rathore A P,Paradkar P N,Watanabe S,et al.Celgosivir treatment misfolds dengue virus NS1 protein,induces cellular pro-survival genes and protects against lethal challenge mouse model [J].Antiviral Res,2011,92(3):453-460.
[13] Whitby K,Taylor D,Patel D,et al.Action of celgosivir(6-O-butanoyl castanospermine)against the pestivirus BVDV:implications for the treatment of hepatitis C [J].Antivir Chem Chemother,2004,15(3):141-151.
[14] Brás N F,Cerqueira N M,Ramos M J,et al.Glycosidase inhibitors:a patent review(2008-2013)[J].Expert Opin Ther Pat,2014,24(8):857-874.
[15] Ruprecht R M,Bernard L D,Bronson R,et al.Castanospermine vs.its 6-O-butanoyl analog:a comparison of toxicity and antiviral activity in vitro and in vivo [J].J Acquir Immune Defic Syndr,1991,4(1):48-55.
[16] Durantel D.Celgosivir,an alpha-glucosidase I inhibitor for the potential treatment of HCV infection [J].Curr Opin Investig Drugs,2009,10(8):860-870.
[17] González-Sabín J,Morán-Ramallal R,Rebolledo F.Regioselective enzymatic acylation of complex natural products:expanding molecular diversity [J].Chem Soc Rev,2011,40(11):5321-5335.
[18] Liu P S,Hoekstra W J,Kinga C H R.Synthesis of potent anti-HIV agents:Esters of castanospermine [J].Tetrahedron Lett,1990,31(20):2829-2832.
[19] anderson W K,Coburn R A,Gopalsamy A,et al.A facile selective acylation of castanospermine [J].Tetrahedron Lett,1990,31(2):169-170.
[20] Margolin A L,Delinck D L,Whalon M R.Enzyme-catalyzed regioselective acylation of castanospermine [J].J Am Chem Soc,1990,112(8):2849-2854.
etc.

备注/Memo

备注/Memo:
收稿日期:2017-06-18基金项目:国家自然科学基金(31360216)和功能有机小分子教育部重点实验室开放课题(KLFS-KF-201226)资助项目.作者简介:彭 仁(1972-),男,江西丰城人,教授,博士,主要从事生物催化和生物转化研究.E-mail:renpeng@jxnu.edu.cn
更新日期/Last Update: 1900-01-01