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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!

小檗碱的结构改造及其药理活性的研究进展

金鑫 宋霞 曹永兵 姜远英 孙青龑

金鑫, 宋霞, 曹永兵, 姜远英, 孙青龑. 小檗碱的结构改造及其药理活性的研究进展[J]. 药学实践与服务, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003
引用本文: 金鑫, 宋霞, 曹永兵, 姜远英, 孙青龑. 小檗碱的结构改造及其药理活性的研究进展[J]. 药学实践与服务, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003
JIN Xin, SONG Xia, CAO Yongbin, JIANG Yuanying, SUN Qingyan. Research progress in structural modification and pharmacological activities of berberine[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003
Citation: JIN Xin, SONG Xia, CAO Yongbin, JIANG Yuanying, SUN Qingyan. Research progress in structural modification and pharmacological activities of berberine[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003

小檗碱的结构改造及其药理活性的研究进展

doi: 10.3969/j.issn.1006-0111.2014.03.003

Research progress in structural modification and pharmacological activities of berberine

  • 摘要: 小檗碱是从中草药黄连等植物中提取并分离得到的一类异喹啉类生物碱。近年来合成了大量小檗碱衍生物,并且发现了广泛的生理功能,其潜在的结构改造和开发应用价值很大。笔者对这些文献进行了较为系统的分析和整理,通过小檗碱不同位点的衍生物所展现的丰富的药理活性,为以小檗碱作为先导物进行的结构改造及创新药物提供了比较系统的信息。
  • [1] 濮礼班,许翔鸿,张宇和,等.黄连生长状况及生物碱含量的个体差异[J].中草药,1999,30(5):375-377.
    [2] 张韶湘,邹 澄,赵 庆,等.小檗碱衙生物的合成及药理活性研究[J].中国民族民间医药杂志,2007,86(03):167-186.
    [3] 林 云,张 灿,华维一.原小檗碱类化合物的构效关系研究进展[J].药学进展,2002,26(2):76-80.
    [4] 刘欣荣.天然药物小檗碱的临床用途[J].光明中医,2007,22(8):73-75.
    [5] 李 波,朱维良,陈凯先.小檗碱及其衍生物的研究进展[J].药学学报,2008,43(8):773-787.
    [6] Li YH,Yang P,Kong WJ,et al.Berberine analogues as a novel class of the low-density lipoprotein receptor up-regulators:synthesis,structure,activity relationships,and cholesterol,lowering efficacy[J].J Med Chem,2009, 52(2): 492-501.
    [7] Yang Y,Ye XL,Li XG,et al.Synthesis and antimicrobial activity of 8-alkylberberine derivatives with a long aliphatic chain[J].Planta Med,2007,73(6): 602-604.
    [8] Cheng Z,Chen AF,Wu F,et al.8,8-dimethyldihydroberberine with improved bioavailability and oral efficacy on obese and diabetic mouse models[J].Bioorg Med Chem,2010,18(16): 5915-5924.
    [9] 西南大学.8-辛基小檗碱盐酸盐、合成方法及应用[P].中国,CN1974569A,2007-06-06.
    [10] Bustanji Y,Taha MO,Yousef AM,et al.Berberine potently inhibits protein tyrosine phosphatase 1B: investigation by docking simulation and experimental validation[J].J Enzyme Inhib Med Chem,2006,21(2): 163-171.
    [11] Wang YX,Fu HG,Li YH,et al.Synthesis and biological evaluation of 8-substituted berberine derivatives as novel anti-mycobacterial agents[J].Acta Pharmaceut Sinica B,2012,2(6): 581-587.
    [12] Hoshi A,Ikekawa T,Ikeda Y,et al.Antitumor activity of berberrubine derivatives[J].Gann, 1976,67(2): 321-325.
    [13] Ma Y,Ou TM,Hou JQ,et al.9-N-substituted berberine derivatives:stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc[J].Bioorg Med Chem,2008,16(16):7582-7591.
    [14] Lo CY, Hsu LC,Chen MS,et al.Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives:a lipophilic substitute role[J].Bioorg Med Chem Lett,2013,23(1):305-309.
    [15] Pang JY,Qin Y,Chen WH,et al.Synthesis and DNA-binding affinities of monomodified berberines[J].Bioorg Med Chem,2005,13(20):5835-5840.
    [16] Chen WH,Pang JY,Qin Y,et al.Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities[J].Bioorg Med Chem Lett,2005,15(10):2689-2692.
    [17] Zhang WJ,Ou TM,Lu YJ,et al.9-substituted berberine derivatives as G-quadruplex stabilizing ligands in telomeric DNA[J].Bioorg Med Chem,2007,15(16):5493-5501.
    [18] Ma Y,Ou TM,Hou JQ,et al.9-N-substituted berberine derivatives: stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc[J].Bioorg Med Chem,2008,16(16):7582-7591.
    [19] Ma Y,Ou TM,Tan JH,et al.Synthesis and evaluation of 9-O-substituted berberine derivatives containing aza-aromatic terminal group as highly selective telomeric G-quadruplex stabilizing ligands[J].Bioorg Med Chem Lett,2009,19(13):3414-3417.
    [20] Basu A,Jaisankar P,Suresh KG,et al.Synthesis of novel 9-O-N-aryl/aryl-alkyl amino carbonyl methyl substituted berberine analogs and evaluation of DNA binding aspects[J].Bioorg Med Chem,2012,20(8):2498-2505.
    [21] Ma Y,Huang ZSh.Synthesis and activity evaluation of 9-O-substituted berberine derivatives containing polyamine Chain as highly selective telomeric G-quadruplex stabilizing ligands[J].Chem J Chin Univ, 2012,33(10):2217-2222.
    [22] Li QY,Zu YG,Liu TY,et al.Generation of reactive oxygen species by a novel berberine-bile acid analog mediates apoptosis in hepatocarcinoma SMMC-7721 cells[J].Biochem Biophys Res Commun,2013,433(4):432-437.
    [23] Kim SH,Lee SJ,Lee JH,et al.Antimicrobial activity of 9-O-acyl-and 9-O-alkylberberrubine derivatives[J].Planta Med,2002,68(3):277-281.
    [24] Hong SW,Kim SH,Jeun JA,et al.Antimicrobial activity of 9-O-acyl-and 9-O-benzoyl-substituted berberrubines[J].Planta Med,2000,66(4):361-363.
    [25] Huang L,Shi A,He F,et al.Synthesis,biological evaluation,and molecular modeling of berberine derivatives as potent acetylcholinesterase inhibitors[J].Bioorg Med Chem,2010,18(3):1244-1251.
    [26] Huang L,Luo Z,He F,et al.Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase[J].Bioorg Med Chem,2010,18(12):4475-4484.
    [27] Shan WJ,Huang L,Zhou Q,et al.Synthesis,biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant,inhibitors of acetylcholinesterase,butyrylcholinesterase and amyloid-β aggregation[J].Eur J Med Chem,2011,46(12):5885-5893.
    [28] Shi AD,Huang L,Lu CJ,et al.Synthesis,biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and beta-amyloid aggregation inhibitors[J].Bioorg Med Chem,2011,19(7):2298-2305.
    [29] Chen Zh,Ye XL,Yi J,et al.Synthesis of 9-O-glycosyl-berberine derivatives and bioavailability evaluation[J].Med Chem Res,2012,21(8):1641-1646.
    [30] Li YH,Li Y,Yang P,et al.Design,synthesis,and cholesterol-lowering efficacy for prodrugs of berberrubine[J].Bioorg Med Chem,2010,18(17):6422-6428.
    [31] Bodiwala HS,Sabde S,Mitra D,et al.Synthesis of 9-substituted derivatives of berberine as anti-HIV agents[J].Eur J Med Chem,2011,46(4):1045-1049.
    [32] Franceschin M,Rossetti L,D'Ambrosio A,et al.Natural and synthetic G-quadruplex interactive berberine derivatives[J].Bioorg Med Chem Lett,2006,16(6):1707-1711.
    [33] Gornall KC,Samosom S,Talib J,et al.Selectivity of an indolyl berberine derivative for tetrameric G-quadruplex DNA[J].Rapid Commun Mass Spectrom,2007,21(11):1759-1766.
    [34] Ball AR,Casadei G,Samosorn S,et al.Conjugating berberine to a multidrug efflux pump inhibitor creates an effective antimicrobial[J].ACS Chem Biol,2006,1(9):594-600.
    [35] Samosorn S,Tanwirat B,Muhamad N,et al.Antibacterial activity of berberine-NorA pump inhibitor hybrids with a methylene ether linking group[J].Bioorg Med Chem,2009,17(11):3866-3872.
    [36] Park KD,Lee JH,Kim SH,et al.Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents[J].Bioorg Med Chem Lett,2006,16(15):3913-3916.
    [37] Liu YX,Xiao CL,Wang YX,et al.Synthesis,structure-activity relationship and in vitro anti-mycobacterial evaluation of 13-n-octylberberine derivatives[J].Eur J Med Chem,2012,52:151-158.
    [38] Iwasa K,Nishiyama Y,Ichmiaru M,et al.Structure activity relationship of quaternary protoberberine alkaloids havnig antimlaarial activity[J].Eur J Med Chem,1999,34:1077-1083.
    [39] Park KD,Cho SJ,Moon JS,et al.Synthesis and antifungal activity of a novel series of 13-(4-isopropylbenzyl)berberine derivatives[J].Bioorg Med Chem Lett,2010,20(22):6551-6554.
    [40] Iwasa K,Lee DU,Kang SI,et al.Antimicrobial activity of 8-alkyl-and 8-phenyl-substituted berberines and their 12-bromo derivatives[J].Nat Prod,1998,61(9):1150-1153.
    [41] Kim JH.Pharmaceutically available protoberberine salts deriva-tives and protoberberine salte derivative,and protoberberin deriv-atives and salts thereof[P].US,008356.1999-12-28.
    [42] 中国科学院上海药物研究所.13,13a-二氢小檗碱衍生物及其药物组合物和用途[P].中国,CN101153039A.2008-04-02.
    [43] Bahar M,Deng Y,Zhu X,et al.Potent antiprotozoal activity of a novel semi-synthetic berberine derivative[J].Bioorg Med Chem Lett,2011,21(9):2606-2610.
    [44] Beausoleil E,Chauvignac C,Taverne T,et al.Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding[J].Bioorg Med Chem Lett,2009,19(19):5594-5598.
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  • 收稿日期:  2013-09-24
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小檗碱的结构改造及其药理活性的研究进展

doi: 10.3969/j.issn.1006-0111.2014.03.003

摘要: 小檗碱是从中草药黄连等植物中提取并分离得到的一类异喹啉类生物碱。近年来合成了大量小檗碱衍生物,并且发现了广泛的生理功能,其潜在的结构改造和开发应用价值很大。笔者对这些文献进行了较为系统的分析和整理,通过小檗碱不同位点的衍生物所展现的丰富的药理活性,为以小檗碱作为先导物进行的结构改造及创新药物提供了比较系统的信息。

English Abstract

金鑫, 宋霞, 曹永兵, 姜远英, 孙青龑. 小檗碱的结构改造及其药理活性的研究进展[J]. 药学实践与服务, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003
引用本文: 金鑫, 宋霞, 曹永兵, 姜远英, 孙青龑. 小檗碱的结构改造及其药理活性的研究进展[J]. 药学实践与服务, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003
JIN Xin, SONG Xia, CAO Yongbin, JIANG Yuanying, SUN Qingyan. Research progress in structural modification and pharmacological activities of berberine[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003
Citation: JIN Xin, SONG Xia, CAO Yongbin, JIANG Yuanying, SUN Qingyan. Research progress in structural modification and pharmacological activities of berberine[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(3): 171-175. doi: 10.3969/j.issn.1006-0111.2014.03.003
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