紫金龙根中异喹啉生物碱及其抗菌活性研究
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国家自然科学基金项目(32000274);云南省基础研究项目(202101AU070069,202101AY070001-066);云南省南药重点实验室开放基金(202105AG070012ZD2220)资助


Isoquinoline Alkaloids from the Roots of Dactylicapnos scandens and Their Antibacterial Activities
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    摘要:

    为了解紫金龙(Dactylicapnos scandens)中异喹啉生物碱化学成分及其抗菌活性,从紫金龙根的乙酸乙酯部位分离得到10个异喹啉类生物碱,根据理化性质和波谱数据,其结构分别鉴定为普罗托品 (1)、1-甲氧基小檗碱 (2)、别隐品碱 (3)、伪普鲁托品 (4)、巴马汀 (5)、青藤碱 (6)、药根碱 (7)、血根碱 (8)、四氢巴马汀 (9)、异紫堇定 (10)。化合物2~48为首次从该种植物中分离得到,其中化合物4对大肠杆菌表现出潜在的抑制活性,MIC值为6.25 μg/mL,抗菌活性优于临床抗菌药物小檗碱(25.0 μg/mL)。

    Abstract:

    To study the isoquinoline alkaloids of Dactylicapnos scandens and their antibacterial activities, ten isoquinoline alkaloids were isolated from its roots. Based on physical and chemical properties and spectral data, their structures were identified as protopine (1), 1-methoxyberberine (2), allocryptopine (3), pseudoprotopine (4), palmatine (5), sinomenine (6), jatrorrhizine (7), sanguinarine (8), tetrahydropalmatine (9), isocorydine (10). Compounds 2-4 and 8 were isolated from this plant for the first time. Moreover, compound 4 exhibited significant antimicrobial activity against Escherichia coli with an MIC value of 6.25 μg/mL, which is better than the clinical antibacterial drug berberine (25.0 μg/mL).

    参考文献
    [1] YAN T Q, AI T M. Study on the chemical constituents from Dactylicapnos scandens [J]. Chin Trad Herb Drugs, 2004, 35(8): 25-26. [严田青, 艾铁民. 紫金龙化学成分的研究[J]. 中草药, 2004, 35(8): 25-26. doi: 10.3321/j.issn:0253-2670.2004.08.009.]
    [2] HE S M, SONG W L, CONG K, et al. Identification of candidate genes involved in isoquinoline alkaloids biosynthesis in Dactylicapnos scandens by transcriptome analysis [J]. Sci Rep, 2017, 7(1): 9119. doi: 10.1038/s41598-017-08672-w.
    [3] MA C Y, YANG H J. Research progress on the traditional Bai medicine: Zixjieillut (Dactylicapnos scandens) [J]. Chin J Ethnomed Ethnopharm, 2011, 20(23): 5-8. [马春云, 杨怀镜. 白族药滋坚伦(紫金龙)的研究进展[J]. 中国民族民间医药, 2011, 20(23): 5-8. doi: 10. 3969/j.issn.1007-8517.2011.23.004.]
    [4] GUO C C, JIANG Y, LI L, et al. Application of a liquid chromatographytandem mass spectrometry method to the pharmacokinetics, tissue distribution and excretion studies of Dactylicapnos scandens in rats [J]. J Pharm Biomed Anal, 2013, 74: 92-100. doi: 10.1016/j.jpba.2012. 10.011.
    [5] WU Y R, ZHAO Y X, LIU Y Q, et al. Alkaloids from Dactylicapnos scandens [J]. Nat Prod Res Dev, 2008, 20(4): 622-626. [吴颖瑞, 赵友兴, 刘玉清, 等. 紫金龙的生物碱成分研究[J]. 天然产物研究与开发, 2008, 20(4): 622-626. doi: 10.3969/j.issn.1001-6880.2008.04.013.]
    [6] WANG B, YANG Z F, ZHAO Y L, et al. Anti-inflammatory isoquinoline with bis-seco-aporphine skeleton from Dactylicapnos scandens [J]. Org Lett, 2018, 20(6): 1647-1650. doi: 10.1021/acs.orglett.8b00400.
    [7] CAO Y, GAO J, GAO X L, et al. Research progress on alkaloids from genus Dactylicapnos Wall. and their pharmacological activities [J]. Chin Trad Herb Drugs, 2014, 45(17): 2556-2563. [曹愿, 高晶, 高小力, 等. 紫金龙属生物碱及其药理活性研究进展[J]. 中草药, 2014, 45(17): 2556-2563.]
    [8] WANG B, ZHAO Y J, ZHAO Y L, et al. Exploring aporphine as anti-inflammatory and analgesic lead from Dactylicapnos scandens [J]. Org Lett, 2020, 22(1): 257-260. doi: 10.1021/acs.orglett.9b04252.
    [9] LIU X F, XIAO J Y, WANG S M, et al. Research progress on bacterial membrane vesicles and antibiotic resistance [J]. Int J Mol Sci, 2022, 23(19): 11553. doi: 10.3390/ijms231911553.
    [10] ÁLVAREZ-MARTÍNEZ F J, BARRAJÓN-CATALÁN E, MICOL V. Tackling antibiotic resistance with compounds of natural origin: A comprehensive review [J]. Biomedicines, 2020, 8(10): 405. doi: 10. 3390/biomedicines8100405.
    [11] LIU R Y, YUAN S, SUN W W, et al. Synthesis and antifungal activity of the derivatives of protopine [J]. Chem Res Appl, 2018, 30(5): 736-744. [刘睿媛, 袁帅, 孙文文, 等. 普罗托品衍生物的合成及其抗菌活性研究[J]. 化学研究与应用, 2018, 30(5): 736-744. doi: 10.3969/j. issn.1004-1656.2018.05.013.]
    [12] CHANG Y, WANG X L, TANG X Y, et al. A new alkaloid from Meconopsis horridula [J]. Nat Prod Res Dev, 2017, 29(5): 731-734. [常颜, 王晓玲, 唐晓莹, 等. 多刺绿绒蒿中的一个新生物碱类化合物[J]. 天然产物研究与开发, 2017, 29(5): 731-734. doi: 10.16333/j. 1001-6880.2017.5.002.]
    [13] IWASA K, NANBA H, LEE D U, et al. Structure-activity relationships of protoberberines having antimicrobial activity [J]. Planta Med, 1998, 64(8): 748-751. doi: 10.1055/s-2006-957572.
    [14] REINHARDT J K, ZIMMERMANN-KLEMD A M, DANTON O, et al. Compounds from Toddalia asiatica: Immunosuppressant activity and absolute configurations [J]. J Nat Prod, 2020, 83(10): 3012-3020. doi: 10.1021/acs.jnatprod.0c00564.
    [15] LI M, CHEN X, TANG Q M, et al. Isoquinoline alkaloids from Thalictrum delavayi [J]. Planta Med, 2001, 67(2): 189-190. doi: 10.1055/ s-2001-11518.
    [16] WAFO P, NYASSE B, FONTAINE C. A 7,8-dihydro-8-hydroxypalmatine from Enantia chlorantha [J]. Phytochemistry, 1999, 50(2): 279-281. doi: 10.1016/S0031-9422(98)00382-3.
    [17] LIU R, MA Y M, ZHANG H C. Chemical constituents of the leaves and stems from Menispermum dauricum [J]. J NW For Univ, 2010, 25(5): 176-178. [刘瑞, 马养民, 张弘弛. 蝙蝠葛茎叶化学成分的初步研究[J]. 西北林学院学报, 2010, 25(5): 176-178.]
    [18] SUN Y T, WANG A L, LI D H, et al. Nitrogeous chemical constituents from Tinosporae radix [J]. Chin Trad Herb Drugs, 2015, 46(9): 1287-1291. [孙雅婷, 王傲莉, 李达翃, 等. 青牛胆含氮类成分研究[J]. 中草药, 2015, 46(9): 1287-1291. doi: 10.7501/j.issn.0253-2670. 2015. 09.006.]
    [19] MIAO F, YANG X J, ZHOU L, et al. Structural modification of sanguinarine and chelerythrine and their antibacterial activity [J]. Nat Prod Res, 2011, 25(9): 863-875. doi: 10.1080/14786419.2010.482055.
    [20] FU J L, LIU J, WU C Q, et al. Separation and purification of the chemical composition of Fibraurea recisa Pierre [J]. Acta Agric Shanghai, 2014, 30(6): 116-119. [扶教龙, 刘佳, 吴晨奇, 等. 天仙藤化学成分分离纯化研究[J]. 上海农业学报, 2014, 30(6): 116-119.]
    [21] LIAN J J, LIU F F, FAN D L, et al. Study of chemical constituents from Stephania hainanensis [J]. J Shenyang Pharm Univ, 2019, 36(3): 202-206. [连敬杰, 刘凡凡, 范冬立, 等. 海南地不容的化学成分[J]. 沈阳药科大学学报, 2019, 36(3): 202-206. doi: 10.14066/j.cnki. cn21-1349/r.2019.03.003.]
    [22] JIA L Y, DENG D, SUN L H, et al. Mechanism of traditional Chinese medicine in treating drug-resistant bacterial infection [J]. Chin J Exp Trad Med Form, 2020, 26(16): 228-234. [贾丽阳, 邓冬, 孙丽华, 等. 中药治疗耐药菌感染作用机制研究进展[J]. 中国实验方剂学杂志, 2020, 26(16): 228-234. doi: 10.13422/j.cnki.syfjx.20201624.]
    [23] EOM S H, LEE D S, JUNG Y J, et al. The mechanism of antibacterial activity of phlorofucofuroeckol-A against methicillinresistant Staphylococcus aureus [J]. Appl Microbiol Biotechnol, 2014, 98(23): 9795-9804. doi: 10.1007/s00253-014-6041-8.
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高雯,吴昊,胡显光,于浩飞,张荣平,丁彩凤.紫金龙根中异喹啉生物碱及其抗菌活性研究[J].热带亚热带植物学报,2024,32(4):555~561

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  • 收稿日期:2023-04-10
  • 最后修改日期:2023-05-22
  • 在线发布日期: 2024-08-21
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