Citation: Zhu Hu-Cheng, Chen Chun-Mei, Zhang Jin-Wen, Guo Yi, Tan Dong-Dong, Guang-ZhengWei, Jing Yang, Wang Jian-Ping, Luo Zeng-Wei, Xue Yong-Bo, Zhang Yong-Hui. Hyperisampsins N and O, two new benzoylated phloroglucinol derivatives from Hypericum sampsonii[J]. Chinese Chemical Letters, ;2017, 28(5): 986-990. doi: 10.1016/j.cclet.2016.11.014 shu

Hyperisampsins N and O, two new benzoylated phloroglucinol derivatives from Hypericum sampsonii

  • Corresponding author: Xue Yong-Bo, yongboxue@hust.edu.cn Zhang Yong-Hui, zhangyh@mails.tjmu.edu.cn
  • 1 These authors contributed equally to this work
  • Received Date: 16 August 2016
    Revised Date: 28 October 2016
    Accepted Date: 9 November 2016
    Available Online: 18 May 2016

Figures(4)

  • Twenty-one benzoylated phloroglucinol derivatives bearing homoadamantyl frameworks were isolated from the aerial parts of Hypericum sampsonii, including two new ones named hyperisampsins N and O (1 and 2). The structures of 1 and 2 were elucidated by extensive NMR and mass spectrometric analyses. Their absolute configurations were further determined by using TDDFT ECD calculations. Compounds 2, 7, and 8 were evaluated for their cytotoxic activities against five human cancer cell lines, of which, 2 and 8 exhibited significant cytotoxic activities toward HL-60 cell and moderate activities against others cell lines.
  • 加载中
    1. [1]

      Ciochina R., Grossman R.B.. Polycyclic polyprenylated acylphloroglucinols[J]. Chem. Rev., 2006(106):3963-3986.

    2. [2]

      Zhang J.J., Yang J., Liao Y.. Hyperuralones A and B. new acylphloroglucinol derivatives with intricately caged cores from Hypericum uralum[J]. Org. Lett., 2014(16):4912-4915.  

    3. [3]

      Yang X.W., Ding Y.Q., Zhang J.J.. New acylphloroglucinol derivatives with diverse architectures from Hypericum henryi[J]. Org. Lett., 2014(16):2434-2437.  

    4. [4]

      Tian W.J., Yu Y., Yao X.J.. Norsampsones A-D. four new decarbonyl polycyclic polyprenylated acylphloroglucinols from Hypericum sampsonii[J]. Org. Lett., 2014(16):3448-3451.  

    5. [5]

      Liao Y., Liu X., Yang J.. Hypersubones A and B. new polycyclic acylphloroglucinols with intriguing adamantane type cores from Hypericum subsessile[J]. Org. Lett., 2015(17):1172-1175.  

    6. [6]

      Tian W.J., Qiu Y.Q., Yao X.J.. Dioxasampsones A and B. two polycyclic polyprenylated acylphloroglucinols with unusual epoxy-ring-fused skeleton from Hypericum sampsonii[J]. Org. Lett., 2014(16):6346-6349.  

    7. [7]

      Zhu H.C., Chen C.M., Yang J.. Bioactive acylphloroglucinols with adamantyl skeleton from Hypericum sampsonii[J]. Org. Lett., 2014(16):6322-6325.  

    8. [8]

      Zhu H.C., Chen C.M., Tong Q.Y.. Hyperisampsins H-M. cytotoxic polycyclic polyprenylated acylphloroglucinols from Hypericum sampsonii[J]. Sci. Rep., 2015(5)14772.  

    9. [9]

      Zhu H.C., Chen C.M., Yang J.. Hyperhexanone A. a crucial intermediate from bicyclo[3.3.1]-to cyclohexanone monocyclic-polycyclic polyprenylated acylphloroglucinols[J]. Tetrahedron, 2016(72):4655-4659.

    10. [10]

      Xiao Z.Y., Zeng Y.H., Mu Q., Shiu W.K.P., Gibbons S.. Prenylated benzophenone peroxide derivatives from Hypericum sampsonii[J]. Chem. Biodivers., 2010(7):953-958.  

    11. [11]

      Ishida Y., Shirota O., Sekita S.. Polyprenylated benzoylphloroglucinoltype derivatives including novel cage compounds from Hypericum erectum[J]. Chem. Pharm. Bull., 2010(58):336-343.  

    12. [12]

      Zhang J.S., Zou Y.H., Guo Y.Q.. Polycyclic polyprenylated acylphloroglucinols:natural phosphodiesterase-4 inhibitors from Hypericum sampsonii[J]. RSC Adv., 2016(6):53469-53476.  

    13. [13]

      Tian W.J., Qiu Y.Q., Jin X.J.. Novel polycyclic polyprenylated acylphloroglucinols from Hypericum sampsonii[J]. Tetrahedron, 2014(70):7912-7916.  

    14. [14]

      Zhou Z.B., Zhang Y.M., Pan K., Luo J.G., Kong L.Y.. Cytotoxic polycyclic polyprenylated acylphloroglucinols from Hypericum attenuatum[J]. Fitoterapia, 2014(95):1-7.  

    15. [15]

      Liu X., Yang X.W., Chen C.Q.. Hypercohones A-C. acylphloroglucinol derivatives with homo-adamantane cores from Hypericum cohaerens[J]. Nat. Prod. Bioprospect., 2013(3):233-237.  

    16. [16]

      Hu L.H., Sim K.Y.. Sampsoniones C-H, a unique family of polyprenylated benzophenone derivatives with the novel tetracyclo[7.3.1.13, 11.03, 7] tetradecane-2, 12, 14-trione skeleton. from Hypericum sampsonii (Guttiferae)[J]. Tetrahedron Lett., 1999(40):759-762.  

    17. [17]

      Henry G.E., Jacobs H., Carrington C.M.S., McLean S., Reynolds W.F.. Prenylated benzophenone derivatives from Caribbean Clusia species (Guttiferae). Plukenetiones B-G and xerophenone A[J]. Tetrahedron, 1999(55):1581-1596.  

    18. [18]

      Zeng Y.H., Osman K., Xiao Z.Y., Gibbons S., Mu Q.. Four geranyl-bearing polyisoprenylated benzoylphloroglucinol derivatives from Hypericum sampsonii[J]. Phytochem. Lett., 2012(5):200-205.

    19. [19]

      Cruz F.G., Teixeira J.S.R.. Polyprenylated Benzophenones with a tricyclo[4.3.1.13.8] undecane skeleton from Clusia obdeltifolia[J]. J. Braz. Chem. Soc., 2004(15):504-508.  

    20. [20]

      Xiao Z.Y., Mu Q., Shiu W.K.P., Zeng Y.H., Gibbons S.. Polyisoprenylated benzoylphloroglucinol derivatives from Hypericum sampsonii[J]. J. Nat. Prod., 2007(70):1779-1782.  

    21. [21]

      Hu L.H., Sim K.Y.. Complex caged polyisoprenylated benzophenone derivatives sampsoniones A and B. from Hypericum sampsonii[J]. Tetrahedron Lett., 1998(39):7999-8002.  

  • 加载中
    1. [1]

      Teng-Yu HuangJunliang SunDe-Xian WangQi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758

    2. [2]

      Shuyan ZHAO . Field-induced Co single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231

    3. [3]

      Xinyi LuoKe WangYingying XueXiaobao CaoJianhua ZhouJiasi Wang . Digital PCR-free technologies for absolute quantitation of nucleic acids at single-molecule level. Chinese Chemical Letters, 2025, 36(2): 109924-. doi: 10.1016/j.cclet.2024.109924

    4. [4]

      Dan-Ying XingXiao-Dan ZhaoChuan-Shu HeBo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436

    5. [5]

      Xiumei LIYanju HUANGBo LIUYaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109

    6. [6]

      Maitri BhattacharjeeRekha Boruah SmritiR. N. Dutta PurkayasthaWaldemar ManiukiewiczShubhamoy ChowdhuryDebasish MaitiTamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007

    7. [7]

      Chunyan YangQiuyu RongFengyin ShiMenghan CaoGuie LiYanjun XinWen ZhangGuangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C3N4 for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767

Metrics
  • PDF Downloads(0)
  • Abstract views(623)
  • HTML views(3)

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
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return