Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum scabrum

被引:18
作者
Hu, Jiawen
Gao, Wan
Xu, Fang
Wei, Canjing
Shi, Mengjiao
Sun, Hua
Zhen, Bo
Wang, Jiajia
Ji, Tengfei [1 ]
Jiang, Jiandong [1 ]
机构
[1] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
基金
国家自然科学基金国际合作与交流项目;
关键词
Hypericum; PPAPs; ECD; Hepatoprotective; POLYISOPRENYLATED BENZOYLPHLOROGLUCINOL DERIVATIVES; SAMPSONII; URALUM; CORES;
D O I
10.1016/j.bmcl.2017.09.001
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Three new polycyclic polyprenylated acylphloroglucinol derivatives (PPAPs), hyperibrins E-G (1-3), along with seven known compounds were identified from the air-dried aerial parts of Hypericum scabrum. Their structures were determined by NMR spectroscopic methods, both experimental and calculated electronic circular dichroism (ECD) spectra and comparison with known compounds. Compound 1 was derived from an analogue of compound 2 by cyclization, while a retro-Claisen reaction transformed another analogue of compound 2 into compound 3. Compounds 3, 4, 5, and 10 showed obvious hepatoprotective activities against paracetamol-induced HepG2 cell damage. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4932 / 4936
页数:5
相关论文
共 50 条
  • [41] Supercritical extraction of phloroglucinol and benzophenone derivatives from Hypericum carinatum: Quantification and mathematical modeling
    Barros, Francisco M. C.
    Silva, Flavia C.
    Nunes, Jessica M.
    Vargas, Rubem M. F.
    Cassel, Eduardo
    von Poser, Gilsane L.
    JOURNAL OF SEPARATION SCIENCE, 2011, 34 (21) : 3107 - 3113
  • [42] Hypatulins A and B, Meroterpenes from Hypericum patulum
    Tanaka, Naonobu
    Yano, Yuki
    Tatano, Yutaka
    Kashiwada, Yoshiki
    ORGANIC LETTERS, 2016, 18 (20) : 5360 - 5363
  • [43] Hypericum scabrum L.-infused locust bean gum/agar hydrogel film: A novel candidate for anti-aging facial mask applications
    Gulen, Rukiye Boran
    INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2025, 306
  • [44] Phloroglucinol derivatives from Hypericum species induce in vitro proliferation of cells involved in the wound healing process
    Bridi, Henrique
    Beckenkamp, Aline
    Maurmann, Natasha
    Elingson, Bianca
    Buffon, Andreia
    Pranke, Patricia
    von Poser, Gilsane Lino
    NATURAL PRODUCT RESEARCH, 2021, 35 (22) : 4648 - 4652
  • [45] Antimicrobial activities of five endemic Hypericum species from Anatolia compared with Hypericum perforatum
    Eroglu Ozkan, Esra
    Ozbek Celik, Berna
    Mat, Afife
    JOURNAL OF RESEARCH IN PHARMACY, 2019, 23 (01): : 114 - 119
  • [46] Diverse Polyphenols from Hypericum faberi
    Zhang, Xin-Wen
    Ye, Yan-Song
    Xia, Fan
    Yang, Xing-Wei
    Xu, Gang
    NATURAL PRODUCTS AND BIOPROSPECTING, 2019, 9 (03) : 215 - 221
  • [47] Prenylated Acylphloroglucinols from Hypericum faberi
    Zhang, Xin-Wen
    Fan, Shao-Qiang
    Xia, Fan
    Ye, Yan-Song
    Yang, Xing-Wei
    Yang, Xian-Wen
    Xu, Gang
    JOURNAL OF NATURAL PRODUCTS, 2019, 82 (05): : 1367 - 1371
  • [48] Composition and antifungal activity of essential oils isolated from Hypericum hyssopifolium and Hypericum heterophyllum
    Cakir, A
    Kordali, S
    Zengin, H
    Izumi, S
    Hirata, T
    FLAVOUR AND FRAGRANCE JOURNAL, 2004, 19 (01) : 62 - 68
  • [49] Unprecedented nor-seco-polycyclic polyprenylated acylphloroglucinols counteract myocardial cell injury via activation of the Akt/mTOR signaling pathway
    Wei, Jiangchun
    Fan, Pingping
    Jin, Xingpiao
    Li, Xinping
    Li, Zhiyue
    Chen, Xuanluan
    Zeng, Hanxiao
    Wu, Zhengzhi
    Zhang, Yonghui
    Hu, Zhengxi
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (19): : 5350 - 5357
  • [50] The essential oils of the aerial parts of two Hypericum taxa (Hypericum triquetrifolium and Hypericum aviculariifolium subsp depilatum var. depilatum (Clusiaceae)) from Turkey
    Yuce, Ebru
    Bagci, Eyup
    NATURAL PRODUCT RESEARCH, 2012, 26 (21) : 1985 - 1990