Message Board

Respected readers, authors and reviewers, you can add comments to this page on any questions about the contribution, review,        editing and publication of this journal. We will give you an answer as soon as possible. Thank you for your support!

Name
E-mail
Phone
Title
Content
Verification Code
x Close Forever Close
Volume 37 Issue 5
. 
Turn off MathJax
Article Contents
Abstract
References
Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2019  >  37(5): 444-449

SHEN Liru, LI Ruihong, WANG Tailiang. Simultaneous determination of peimine and peiminine in Xiaoer Baotaikang granules by HPLC-ELSD[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(4): 351-353. doi: 10.3969/j.issn.1006-0111.2016.04.017
Citation: LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
shu

The total solid synthesis of marine cyclopeptide stylissamide Ⅰ

doi: 10.3969/j.issn.1006-0111.2019.05.011
  • 1.

    Department of Pharmacy, Changhai Hospital, Naval Medical University, Shanghai 200433, China

  • 2.

    School of Pharmacy, Naval Medical University, Shanghai 200433, China

  • Received Date: 2018-10-31
  • Rev Recd Date: 2019-02-13
  • Objective The marine cyclopeptide stylissamide Ⅰ was synthesized through a solid phase synthesis and cyclization in solution(SPS-CS). Methods 2-chlorotrityl chloride resin was used as solid support for the total synthesis.Each amino acid protected by 9-fluorenylmethyloxycarbonyl(Fmoc) group was coupled with N,N-diisopropylethylamine(DIPEA)/O-(6-chloro-1-hydrocibenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro- phosphat(HCTU) as condensing agents.The linear peptide was cleaved from resin by 2,2,2-trifluoroethanol(TFE) and cyclized in the presence of(7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate(PyAOP)/1-hydroxy-7-azabenzotriazole(HOAt)/N-methyl morphofine(NMM).Finally,the crude cyclopeptide was obtained through global deprotection with trifluoroacetic acid(TFA).The target compound was purified by preparative RP-HPLC to 98.9% pure and its structure was identified by 1H-NMR,13C-NMR and Q-TOF LC/MS. Results The first total synthesis of the marine cyclopeptide stylissamide Ⅰ was successfully realized with a yield of 67%. Conclusion A rapid,simple and high-efficient method of stylissamide Ⅰ total synthesis was successfully established.
  • [1] NORO J C,KALAITZIS J A,NEILAN B A.Bioactive natural products from Papua New Guinea marine sponges[J].Chem Biodivers,2012,9(10):2077-2095.
    [2] PROKSCH P,EBEL R,EDRADA R A,et al.Bioactive natural products from marine invertebrates and associated fungi[J].Prog Mol Subcell Biol,2003,37:117-142.
    [3] ANDAVAN G S,LEMMENS-GRUBER R.Cyclodepsipeptides from marine sponges:Natural agents for drug research[J].Mar Drugs,2010,8(3):810-834.
    [4] PIFFERI C,BERTHET N,RENAUDET O.Cyclopeptide scaffolds in carbohydrate-based synthetic vaccines[J].Biomater Sci,2017,5(5):953-965.
    [5] KURANAGA T,SESOKO Y,INOUE M.Cu-mediated enamide formation in the total synthesis of complex peptide natural products[J].Nat Prod Rep,2014,31(4):514-532.
    [6] RUSSO A,AIELLO C,GRIECO P,et al.Targeting "undruggable" proteins:design of synthetic cyclopeptides[J].Curr Med Chem,2016,23(8):748-762.
    [7] DAHIYA R,GAUTAM H.Toward the synthesis and biological screening of a cyclotetrapeptide from marine bacteria[J].Mar Drugs,2010,9(1):71-81.
    [8] CHANDRA K,ROY T K,SHALEV D E,et al.A tandem in situ peptide cyclization through trifluoroacetic acid cleavage[J].Angew Chem Int Ed Engl,2014,53(36):9450-9455.
    [9] DALETOS G,KALSCHEUER R,KOLIWER-BRANDL H,et al.Callyaerins from the marine sponge Callyspongia aerizusa:Cyclic peptides with antitubercular activity[J].J Nat Prod,2015,78(8):1910-1925.
    [10] ZHOU X,HUANG H,CHEN Y,et al.Marthiapeptide A,an anti-infective and cytotoxic polythiazole cyclopeptide from a 60 L scale fermentation of the deep sea-derived Marinactinospora thermotolerans SCSIO 00652[J].J Nat Prod,2012,75(12):2251-2255.
    [11] KANG K B,MING G,KIM G J,et al.Jubanines F-J,cyclopeptide alkaloids from the roots of Ziziphus jujuba[J].Phytochemistry,2015,119:90-95.
    [12] ESMAEILI M A,ABAGHERI-MAHABADI N,HASHEMPOUR H,et al.Viola plant cyclotide vigno 5 induces mitochondria-mediated apoptosis via cytochrome C release and caspases activation in cervical cancer cells[J].Fitoterapia,2016,109:162-168.
    [13] THEVENARD J,RAMONT L,DEVY J,et al.The YSNSG cyclopeptide derived from tumstatin inhibits tumor angiogenesis by down-regulating endothelial cell migration[J].Int J Cancer,2010,126(5):1055-1066.
    [14] FESTA C,DE MARINO S,SEPE V,et al.Solomonamides A and B,new anti-inflammatory peptides from Theonella swinhoei[J].Org Lett,2011,13(6):1532-1535.
    [15] SONG L,WANG Z,WANG Y,et al.Natural Cyclopeptide RA-XⅡ,a new autophagy inhibitor,suppresses protective autophagy for enhancing apoptosis through AMPK/mTOR/P70S6K pathways in HepG2 cells[J].Molecules,2017,22(11):1934.
    [16] SCHMIDT G,GRUBE A,KÖCK M.Stylissamides A-D new proline-containing cyclic heptapeptides from the marine sponge Stylissa caribica[J].Eur J Org Chem,2007,2007(24):4103-4110.
    [17] CYCHON C,KÖCK M.Stylissamides E and F,cyclic heptapeptides from the caribbean sponge Stylissa caribica[J].J Nat Prod,2010,73(4):738-742.
    [18] CYCHON C,SCHMIDT G,KÖCK M.Sequencing of cyclic peptides by NMR and MS techniques demonstrated on stylissamides A-F[J].Phytochem Rev,2013,12(3):495-505.
    [19] KUBOTA T,KOBAYASHI J,NAKAMURA K,et al.stylissamide Ⅰ,a new cyclic heptapeptide from an okinawan marine sponge Stylissa sp.[J].Heterocycles,2017,95(2):799-806.
    [20] 刘雷明,王国亮,王建华,等.AoGDW肽固相合成工艺研究[J].化学试剂,2009,31(11):871-874.
    [21] RIJKERS D T S,KRUIJTZER J A W,KILLIAN J A,et al.A convenient solid phase synthesis of S-palmitoyl transmembrane peptides[J].Tetrahedron Lett,2005,46(19):3341-3345.
    [22] CHEN Y,LIU C,LIU N,et al.Total synthesis and antibacterial study of cyclohexapeptides desotamide B,wollamide B and their analogs[J].Chem Biodivers,2017,15(1):e1700414.
    [23] LIU C,ZOU Y,SONG H,et al.Arylboronate ester protected amino acids as orthogonal building blocks for fmoc solid phase peptide synthesis[J].Eur J Org Chem,2017,2017(39):5916-5920.
    [24] HUMPHREY J M,CHAMBERLIN A R.Chemical synthesis of natural product peptides:coupling methods for the incorporation of non-coded amino acids into peptides[J].Chem Rev,1997,97(6):2243-2266.
    [25] LIU C,CHEN X,ZHI X,et al.Structure-based development of an osteoprotegerin-like glycopeptide that blocks RANKL/RANK interactions and reduces ovariectomy-induced bone loss in mice[J].Eur J Med Chem,2018,145:661-672.
    [26] HU H,XUE J,SWARTS B M,et al.Synthesis and antibacterial activities of N-glycosylated derivatives of tyrocidine A,a macrocyclic peptide antibiotic[J].J Med Chem,2009,52(7):2052-2059.
  • Created with Highcharts 5.0.7Amount of accessChart context menuAbstract Views, HTML Views, PDF Downloads StatisticsAbstract ViewsHTML ViewsPDF Downloads2024-052024-062024-072024-082024-092024-102024-112024-122025-012025-022025-032025-0400.511.522.5Highcharts.com
    Created with Highcharts 5.0.7Chart context menuAccess Class DistributionFULLTEXT: 87.2 %FULLTEXT: 87.2 %META: 11.0 %META: 11.0 %PDF: 1.8 %PDF: 1.8 %FULLTEXTMETAPDFHighcharts.com
    Created with Highcharts 5.0.7Chart context menuAccess Area Distribution其他: 25.0 %其他: 25.0 %其他: 0.3 %其他: 0.3 %Canada: 0.1 %Canada: 0.1 %China: 1.3 %China: 1.3 %Neptune City: 0.3 %Neptune City: 0.3 %United States: 0.5 %United States: 0.5 %[]: 0.8 %[]: 0.8 %上海: 3.4 %上海: 3.4 %中卫: 0.1 %中卫: 0.1 %临汾: 0.3 %临汾: 0.3 %临沂: 0.5 %临沂: 0.5 %兰州: 0.3 %兰州: 0.3 %北京: 13.8 %北京: 13.8 %南宁: 0.4 %南宁: 0.4 %南昌: 0.1 %南昌: 0.1 %厦门: 0.1 %厦门: 0.1 %台州: 0.1 %台州: 0.1 %呼和浩特: 0.1 %呼和浩特: 0.1 %哈尔滨: 0.3 %哈尔滨: 0.3 %宁波: 0.3 %宁波: 0.3 %巴音郭楞: 0.1 %巴音郭楞: 0.1 %广安: 0.1 %广安: 0.1 %广州: 0.3 %广州: 0.3 %张家口: 0.4 %张家口: 0.4 %徐州: 0.1 %徐州: 0.1 %恩施: 0.1 %恩施: 0.1 %成都: 0.1 %成都: 0.1 %昆明: 0.1 %昆明: 0.1 %普洱: 0.1 %普洱: 0.1 %杭州: 1.2 %杭州: 1.2 %枣庄: 0.3 %枣庄: 0.3 %桂林: 0.3 %桂林: 0.3 %梅州: 0.1 %梅州: 0.1 %榆林: 0.1 %榆林: 0.1 %武汉: 0.3 %武汉: 0.3 %沈阳: 0.1 %沈阳: 0.1 %泰安: 0.1 %泰安: 0.1 %济南: 0.1 %济南: 0.1 %济宁: 0.1 %济宁: 0.1 %深圳: 0.3 %深圳: 0.3 %漯河: 0.1 %漯河: 0.1 %百色: 0.1 %百色: 0.1 %盐城: 0.3 %盐城: 0.3 %石家庄: 0.9 %石家庄: 0.9 %芒廷维尤: 26.9 %芒廷维尤: 26.9 %芝加哥: 0.1 %芝加哥: 0.1 %衢州: 0.1 %衢州: 0.1 %西宁: 14.5 %西宁: 14.5 %西安: 0.1 %西安: 0.1 %达尔斯: 0.1 %达尔斯: 0.1 %运城: 0.5 %运城: 0.5 %遵义: 0.1 %遵义: 0.1 %郑州: 0.9 %郑州: 0.9 %重庆: 0.3 %重庆: 0.3 %长沙: 0.9 %长沙: 0.9 %长治: 0.1 %长治: 0.1 %防城港: 0.1 %防城港: 0.1 %阳泉: 0.1 %阳泉: 0.1 %青岛: 0.1 %青岛: 0.1 %黄冈: 0.8 %黄冈: 0.8 %黔东南: 0.1 %黔东南: 0.1 %其他其他CanadaChinaNeptune CityUnited States[]上海中卫临汾临沂兰州北京南宁南昌厦门台州呼和浩特哈尔滨宁波巴音郭楞广安广州张家口徐州恩施成都昆明普洱杭州枣庄桂林梅州榆林武汉沈阳泰安济南济宁深圳漯河百色盐城石家庄芒廷维尤芝加哥衢州西宁西安达尔斯运城遵义郑州重庆长沙长治防城港阳泉青岛黄冈黔东南Highcharts.com

  • Cited by

    Periodical cited type(4)

    1. 杨雅婷，吕晓君，张菊，徐小玲，何开勇，沈佳特. 氟马西尼原料药中细菌内毒素检查. 医药导报. 2024(09): 1470-1476 .
    2. 邝昆合，郑德志，江进红，李显立. 氟马西尼用于静吸复合全麻术后催醒的临床效果观察. 中国实用医药. 2023(09): 116-119 .
    3. 张宗鹏，王治国，石庆学，张国旭，霍花. 不同比活度~(11)C-氟马西尼体内代谢的差异分析. 药学实践杂志. 2020(04): 318-321 .
    4. 侯成，卢光照，鲁莹，董腾腾，邹豪. 军事人员对抗睡眠剥夺策略的研究进展. 第二军医大学学报. 2020(09): 1012-1020 .

    Other cited types(1)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Get Citation
PDF
XML

Article Metrics

Article views(4758) PDF downloads(417) Cited by(5)

Related
Proportional views

The total solid synthesis of marine cyclopeptide stylissamide Ⅰ

doi: 10.3969/j.issn.1006-0111.2019.05.011
  • 1. Department of Pharmacy, Changhai Hospital, Naval Medical University, Shanghai 200433, China
  • 2. School of Pharmacy, Naval Medical University, Shanghai 200433, China
  • Received Date: 2018-10-31
  • Rev Recd Date: 2019-02-13

Abstract: Objective The marine cyclopeptide stylissamide Ⅰ was synthesized through a solid phase synthesis and cyclization in solution(SPS-CS). Methods 2-chlorotrityl chloride resin was used as solid support for the total synthesis.Each amino acid protected by 9-fluorenylmethyloxycarbonyl(Fmoc) group was coupled with N,N-diisopropylethylamine(DIPEA)/O-(6-chloro-1-hydrocibenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro- phosphat(HCTU) as condensing agents.The linear peptide was cleaved from resin by 2,2,2-trifluoroethanol(TFE) and cyclized in the presence of(7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate(PyAOP)/1-hydroxy-7-azabenzotriazole(HOAt)/N-methyl morphofine(NMM).Finally,the crude cyclopeptide was obtained through global deprotection with trifluoroacetic acid(TFA).The target compound was purified by preparative RP-HPLC to 98.9% pure and its structure was identified by 1H-NMR,13C-NMR and Q-TOF LC/MS. Results The first total synthesis of the marine cyclopeptide stylissamide Ⅰ was successfully realized with a yield of 67%. Conclusion A rapid,simple and high-efficient method of stylissamide Ⅰ total synthesis was successfully established.

SHEN Liru, LI Ruihong, WANG Tailiang. Simultaneous determination of peimine and peiminine in Xiaoer Baotaikang granules by HPLC-ELSD[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(4): 351-353. doi: 10.3969/j.issn.1006-0111.2016.04.017
Citation: LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
shu

    HTML

Reference (26)

Catalog

  • HTML

版权所有：《药学实践与服务》编辑委员会

Supervisor & Sponsors: Address: No 325 Guohe Road, ShanghaiPost Code: 200433

Tel: （021）81871324,81871397 E-mail: yxsjzzs@163.com

网站备案号 沪ICP备05003363号-1

Supported by: Beijing Renhe Information Technology Co., Ltd.  

/

DownLoad:  Full-Size Img  PowerPoint
Return
Return