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[1]彭宇然,孙亦诚,王德才,等.8,17-环氧穿心莲内酯衍生物的合成与抗菌活性[J].南京工业大学学报(自然科学版),2016,38(04):67-78.[doi:10.3969/j.issn.1671-7627.2016.04.013]
 PENG Yuran,SUN Yicheng,WANG Decai,et al.Synthesis and antibacterial activity of 8,17-epoxy-andrographolide derivatives[J].Journal of NANJING TECH UNIVERSITY(NATURAL SCIENCE EDITION),2016,38(04):67-78.[doi:10.3969/j.issn.1671-7627.2016.04.013]
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8,17-环氧穿心莲内酯衍生物的合成与抗菌活性()
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《南京工业大学学报(自然科学版)》[ISSN:1671-7627/CN:32-1670/N]

卷:
38
期数:
2016年04期
页码:
67-78
栏目:
出版日期:
2016-07-10

文章信息/Info

Title:
Synthesis and antibacterial activity of 8,17-epoxy-andrographolide derivatives
文章编号:
1671-7627(2016)04-0067-12
作者:
彭宇然12孙亦诚1王德才1欧阳平凯2周国春1
1.南京工业大学 药学院,江苏 南京 211800; 2.南京工业大学 生物与制药工程学院,江苏 南京 211800
Author(s):
PENG Yuran12SUN Yicheng1WANG Decai1OUYANG Pingkai2ZHOU Guochun1
1.College of Pharmaceutical Sciences,Nanjing Tech University,Nanjing 211800,China; 2.College of Biotechnology and Pharmaceutical Engineering,Nanjing Tech University,Nanjing 211800,China
关键词:
穿心莲内酯 环氧化 抗菌活性
Keywords:
andrographolide epoxidation antibacterial activity
分类号:
R284.3
DOI:
10.3969/j.issn.1671-7627.2016.04.013
文献标志码:
A
摘要:
为了提高穿心莲内酯的抗菌能力,将端头烯键环氧化得到12个8,17-环氧穿心莲内酯衍生物。目标化合物均通过核磁共振仪(NMR)与高分辨质谱仪(HRMS)表征。在合成实验中,考察了穿心莲内酯3个羟基与叔丁基二甲硅基(TBS)结合与脱除的能力。抗菌活性实验研究发现,化合物B5与C5对大肠杆菌、粪肠球菌以及金黄色葡萄球菌的抑制能力均优于先导化合物穿心莲内酯,具有潜在的应用价值。
Abstract:
To enhance the antibacterial activity of andrographolide,twelve 8,17-epoxy-andrographolide derivatives were synthesized through the epoxidation of the exocyclic olefin.All the target compounds were characterized by nuclear magnetic resonance(NMR)and high resolution mass spectra(HRMS).The capabilities of formation and cleavage of the tert-butyldimethylsilyl(TBS)group at the three hydroxyl groups of andrographolide were investigated.Compounds B5 and C5 had stronger inhibition activities against Escherichia coli,Enterococcus faecalis and Staphylococcus aureus than those of andrographolide.

参考文献/References:

[1] 刘国利,刘永琼.穿心莲内酯的研究进展[J].医药导报,2006,25(1):48.
[2] 广州市药品检验所中草药科.穿心莲内酯的抗菌解热药理试验[J].新医药通讯,1974(1):16.
[3] SINGHA P K,ROY S,DEY S.Antimicrobial activity of Andrographis paniculata[J].Fitoterapia,2003,74(7):692.
[4] 王静,华子瑜,沈犁,等.穿心莲内酯对临床铜绿假单胞菌感染人支气管上皮细胞的干预研究[J].重庆医科大学学报,2013,38(10):1194.
[5] LEELARASAMEE A,TRAKULSOMBOON S,SITTISOMWONG N.Undetectable anti-bacterial activity of Andrographis paniculata(Burma)wall.ex ness.[J].Journal of the medical association of thailand,1990,73(6):299.
[6] TANG C L,ZHANG W J,WANG X Y,et al.Synthesis and biological evaluation of andrographolide derivatives as potent antibacterial agents[J].Letters in drug design & discovery,2011,8(9):816.
[7] JIANG X J,YU P,JIANG J,et al.Synthesis and evaluation of antibacterial activities of andrographolide analogues[J].European journal of medicinal chemistry,2009,44(7):2936.
[8] NANDURI S,NYAVANANDI V K,THUNUGUNTLA S S R,et al.Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents[J].Bioorganic & medicinal chemistry letters,2004,14(18):4711.
[9] SIRION U,KASEMSOOK S,SUKSEN K,et al.New substituted C-19-andrographolide analogues with potent cytotoxic activities[J].Bioorganic & medicinal chemistry letters,2012,22(1):49.
[10] LIU Z Y,LAW W K,WANG D C,et al.Synthesis and discovery of andrographolide derivatives as nonsteroidal farnesoid X receptor(FXR)antagonists[J].RSC advances,2014,4:13533.
[11] GAO H T,WANG B L,LI W D Z.Synthetic applications of homoiodo allylsilane:II.total syntheses of(-)-andrographolide and(+)-rostratone[J].Tetrahedron,2014,70(49):9436.
[12] SONG Y P,XIN Z Y,WAN Y M,et al.Synthesis and anticancer activity of some novel indolo[3,2-B] andrographoli de derivatives as apoptosis-indu cing agents[J].European journal of medicinal chemistry,2015,90:695.
[13] PENG Y R,LI J J,SUN Y C,et al.SAR studies of 3,14,19-derivatives of andrographolide on anti-proliferative activity to cancer cells and toxicity to zebrafish:an in vitro and in vivo study[J].RSC advances,2015,5:22510.
[14] PREET R,CHAKRABORTY B,SIDDHARTH S,et al.Synthesis and biological evaluation of andrographolide analogues as anti-cancer agents[J].European journal of medicinal chemistry,2014,85:95-106.doi:10.1016/j.ejmech.2014.07.088.
[15] GREENE TW,WOTS P G M.有机合成中的保护基[M].华东理工大学有机化学调研组,译.上海:华东理工大学出版社,2004.

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备注/Memo

备注/Memo:
收稿日期:2015-02-12
基金项目:国家自然科学基金(30973621)
作者简介:彭宇然(1986—),男,江苏南京人,博士生,主要研究方向为化学合成药物; 王德才(联系人),教授,E-mail: dcwang@njtech.edu.cn.
引用本文:彭宇然,孙亦诚,王德才,等.8,17-环氧穿心莲内酯衍生物的合成与抗菌活性[J].南京工业大学学报(自然科学版),2016,38(4):67-78..
更新日期/Last Update: 2016-07-10