芒果苷衍生物的合成及其PTP1B酶抑制活性研究

周宇; 胡丽娜; 罗剑飞; 俞世冲; 吴秋业

留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码

x 关闭永久关闭

应中央军委要求，2022年9月起，《药学实践杂志》将更名为《药学实践与服务》，双月刊，正文96页；2023年1月起，拟出版月刊，正文64页，数据库收录情况与原《药学实践杂志》相同。欢迎作者踊跃投稿！

芒果苷衍生物的合成及其PTP1B酶抑制活性研究

周宇, 胡丽娜, 罗剑飞, 俞世冲, 吴秋业

文章导航 > 药学实践与服务 > 2011 > 29(3): 193-196

周宇, 胡丽娜, 罗剑飞, 俞世冲, 吴秋业. 芒果苷衍生物的合成及其PTP1B酶抑制活性研究[J]. 药学实践与服务, 2011, 29(3): 193-196.

引用本文:

周宇, 胡丽娜, 罗剑飞, 俞世冲, 吴秋业. 芒果苷衍生物的合成及其PTP1B酶抑制活性研究[J]. 药学实践与服务, 2011, 29(3): 193-196.

ZHOU Yu, HU Li-na, LUO Jian-fei, YU Shi-chong, WU Qiu-ye. Synthesis and PTP1B activity of enzyme inhibition of mangiferin derivates[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(3): 193-196.

Citation:

ZHOU Yu, HU Li-na, LUO Jian-fei, YU Shi-chong, WU Qiu-ye. Synthesis and PTP1B activity of enzyme inhibition of mangiferin derivates[J]. Journal of Pharmaceutical Practice and Service, 2011, 29(3): 193-196.

芒果苷衍生物的合成及其PTP1B酶抑制活性研究

1.
解放军第82医院,江苏淮安 223001
2.
第二军医大学有机化学教研室,上海 200433

基金项目: 上海市科委基础重点项目 ( 08JC1405500).

Synthesis and PTP1B activity of enzyme inhibition of mangiferin derivates

1.
NO. 82 Hospital of PLA, Huaian 223001,China
2.
Department of Organic Chemistry,School of Pharmacy,Second Military Medical University,Shanghai 200433,China

摘要: 目的设计合成一系列芒果苷衍生物并进行体外蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性实验。方法利用亲核取代反应在芒果苷上引入疏水苄基,设计合成8个新化合物4~11,采用比色法对化合物进行PTP1B抑制活性研究。结果设计合成的8个化合物对PTP1B酶都有一定的抑制作用。结论芒果苷衍生物的活性明显好于芒果苷本身的活性,苄基的对位取代活性要优于邻位和间位取代,且苄基上氯原子取代的衍生物要高于其它原子取代的化合物活性。
- 芒果苷 /
- 蛋白酪氨酸磷酸酶1B /
- 化学合成 /
- 抑制活性
Abstract: Objective To synthetize and conduct PTP1B inhibitory activity experiment of series of novel mangiferin derivates. Methods Different benzyl groups were introduced to mangiferin framework by nucleophilic substitution reaction. All the compounds were screened against protein tyrosine phosphatase 1B(PTP1B)with the colorimetrie assay. Results Eight compounds were synthesized and all the compounds exhibited PTP1B inhibitory activity to some extent. Conclusions Derivates of mangiferin remarkably enhanced the activity compared with mangiferin itself. In addition, the benzylated derivates with chloro atom had better inhibitory activity than other substitution groups. Furthermore,the para position of the benzyl was a better place for introducing substituent than meta and ortho position.
- mangiferin /
- protein tyrosine phosphatase 1B /
- chemical synthesis /
- inhibition

[1]	Pardo-Andreu GL, Rene D, Alberto J, et al. Mangifera indica L, extract (Vimang) inhibits 2-deoxyribose damage induced by Fe (Ⅲ) plus ascorbate[J].Phytother Res, 2006, 20(2):120.
[2]	彭志刚,罗军,赖永熔,等.芒果苷对K562胞端粒酶活性和细胞周期的影响[J].中药药理与临床,2007, 23(1): 13.
[3]	Rivera DG, Balmaseda IH, Leon AA, et al. Anti-allergic properties of Manglfera indica L. extract (Vimang) and contribution of its glueosylxanthone mangiferin[J]. J Pham Pharmacol, 2006, 58(3): 385.
[4]	Gottlieb M, Leal-Campanario R, Campos-Esparza MR, et al. Neuroprotection by two polyphenols following excitotoxicity and experimental ischemia[J]. Neurobiology of Disease, 2006, 23(2): 374.
[5]	Hu HG, Liao HL, Zhang J, et al. First identification of xanthone sulfonamides as potent acyl-CoA: cholesterol acyltransferase (ACAT) inhibitors[J]. Bioorg Med Chem Lett, 2010, 20(10): 3094.
[6]	Miura T, Ichiki H, Iwamoto N, et al. Antidiabetic activity of the rhizoma of Anemarrhena asphodeloides and active components, mangiferin and its glucoside[J]. Biol Pharm Bull, 2001, 24(9): 1009.
[7]	Miura T, Ichiki H, Hashimoto I, et al. Antidiabetic activity of a xanthone compound, mangiferin[J]. Phytomedicine, 2001, 8(2): 85.
[8]	Pei Z, Liu G, Lubben TH, et al. Inhibition of protein tyrosine phosphatase 1B as a potential treatment of diabetes and obesity[J]. Curr Pharm Des, 2004, 10(28): 3481.
[9]	Dadke S, Chernoff J. Protein-tyrosine phosphatase 1B as a potential drug target for obesity[J]. Curr Drug Targets Immune Endocr Metabol Disord, 2003, 3(4): 299.
[10]	Kim HO, Blaskovich MA. Recent discovery and development of protein tyrosine phosphatase inhibitors[J]. Expert Opin Ther Patents, 2002, 12(6): 871.
[11]	Elchebly M, Payette P, Michaliszyn E, et al. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene[J]. Science, 1999, 283(5407): 1544.
[12]	Klaman LD, Boss O, Peroni OD, et al. Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1B-deficient mice[J]. Mol Cell Biol, 2000, 20(15): 5479.
[13]	廖洪利,陈军,杨倩.芒果苷衍生物的制备[J].药学实践杂志,2010, 27(5): 49.
[14]	Goldstein BJ, Bittner-Kowalezyk A, White MF, et al. Tyrosine dephosphorylation and deactivation of insulin receptor substrate-1 by protein-tyrosine phosphatase 1B: Possible facilitation by the formation of a ternary complex with the GRB2 adaptor protein[J]. J Biol Chem, 2000, 275: 4283.

[1]	岳春华, 贲永光, 王海桥. 基于NLRP1炎症小体探讨百合知母汤抗抑郁的作用机制 . 药学实践与服务, 2024, 42(8): 325-333. doi: 10.12206/j.issn.2097-2024.202401033
[2]	李想, 陆鸿远, 张明玉, 高欢, 姚东, 许子华. 米格列醇激活UCP1介导棕色脂肪对冷暴露小鼠损伤的研究 . 药学实践与服务, 2024, 42(): 1-6. doi: 10.12206/j.issn.2097-2024.202404005
[3]	夏哲炜, 曾垣烨, 朱海菲, 李育, 陈啸飞. 核磁共振磷谱法测定磷酸氢钙咀嚼片中药物含量 . 药学实践与服务, 2024, 42(9): 399-401, 406. doi: 10.12206/j.issn.2097-2024.202404063
[4]	陈静, 何瑞华, 翁月, 徐熠, 刘静, 黄瑾. 基于网络药理学和分子对接技术探究定清片活性成分治疗白血病的作用机制 . 药学实践与服务, 2024, 42(11): 479-486. doi: 10.12206/j.issn.2097-2024.202401073
[5]	陈炳辰, 王思真, 郭贝贝, 杨峰. 紫杉醇棕榈酸酯的合成及其脂质体的制备与处方研究 . 药学实践与服务, 2024, 42(9): 379-384, 410. doi: 10.12206/j.issn.2097-2024.202404062
[6]	杨媛媛, 安晓强, 许佳捷, 江键, 梁媛媛. 正极性驻极体联合5-氟尿嘧啶对瘢痕成纤维细胞生长抑制的协同作用 . 药学实践与服务, 2024, 42(6): 244-247. doi: 10.12206/j.issn.2097-2024.202310027
[7]	景凯, 杨慈荣, 张圳, 臧艺蓓, 刘霞. 黄芪甲苷衍生物治疗慢性心力衰竭小鼠的药效评价及作用机制研究 . 药学实践与服务, 2024, 42(5): 190-197. doi: 10.12206/j.issn.2097-2024.202310004
[8]	赖立勇, 夏天爽, 徐圣焱, 蒋益萍, 岳小强, 辛海量. 中药青蒿抗氧化活性的谱效关系研究 . 药学实践与服务, 2024, 42(5): 203-210, 216. doi: 10.12206/j.issn.2097-2024.202211012
[9]	刘汝雄, 杨万镇, 涂杰, 盛春泉. 铁死亡调控蛋白GPX4的小分子抑制剂研究进展 . 药学实践与服务, 2024, 42(9): 375-378. doi: 10.12206/j.issn.2097-2024.202312075

点击查看大图

计量

文章访问数: 2896
HTML全文浏览量: 292
PDF下载量: 166
被引次数: 0

芒果苷衍生物的合成及其PTP1B酶抑制活性研究

1. 解放军第82医院,江苏淮安 223001

2. 第二军医大学有机化学教研室,上海 200433

基金项目: 上海市科委基础重点项目 ( 08JC1405500).

收稿日期: 2011-01-06
修回日期: 2011-03-10

关键词:

芒果苷 /

蛋白酪氨酸磷酸酶1B /

化学合成 /

抑制活性

摘要: 目的设计合成一系列芒果苷衍生物并进行体外蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性实验。方法利用亲核取代反应在芒果苷上引入疏水苄基,设计合成8个新化合物4~11,采用比色法对化合物进行PTP1B抑制活性研究。结果设计合成的8个化合物对PTP1B酶都有一定的抑制作用。结论芒果苷衍生物的活性明显好于芒果苷本身的活性,苄基的对位取代活性要优于邻位和间位取代,且苄基上氯原子取代的衍生物要高于其它原子取代的化合物活性。