Cephalotane-Type Norditerpenoids from Cephalotaxus fortunei var. alpina

被引:29
作者
Ge, Zhan-Peng [1 ]
Zhou, Bin [1 ]
Zimbres, Flavia M. [2 ]
Cassera, Maria B. [2 ]
Zhao, Jin-Xin [1 ]
Yue, Jian-Min [1 ]
机构
[1] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
[2] Univ Georgia, Ctr Trop & Emerging Global Dis CTEGD, Dept Biochem & Mol Biol, Athens, GA 30602 USA
基金
中国国家自然科学基金;
关键词
Cephalotaxus fortunei var; alpine; Natural products; Structural elucidation; Cephalotane norditerpenoids; Antimalarial activity; A-D;
D O I
10.1002/cjoc.202100913
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Comprehensive Summary A chemical investigation of the 95% EtOH extract of the seeds of Cephalotaxus fortunei var. alpina led to the isolation of nine new cephalotane-type norditerpenoids, ceforalides A-I (1-9), and two known analogues (10 and 11). Compounds 1-8 belong to a rare class of A-ring-contracted cephalotane-type norditerpenoids, of which compound 8 incorporates a unique tetrasubstituted 2,5-cyclohexadienone A-ring. Compound 9 is a rare 13,14-seco-17-nor-cephalotane-type diterpenoid. Their structures were determined based on NMR, HRESIMS, ECD, and X-ray diffraction analysis. Biological tests revealed compounds 10 and 11 displayed moderate antimalarial activity.
引用
收藏
页码:1177 / 1184
页数:8
相关论文
共 32 条
  • [1] Asymmetric Total Synthesis of (+)-Mannolide C
    Ao, Qiaoqiao
    Zhang, Hai-Jun
    Zheng, Jinbin
    Chen, Xiaoming
    Zhai, Hongbin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (39) : 21267 - 21271
  • [2] HARRINGTONOLIDE, A PLANT-GROWTH INHIBITORY TROPONE FROM CEPHALOTAXUS-HARRINGTONIA (FORBES) K KOCH
    BUTA, JG
    FLIPPEN, JL
    LUSBY, WR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) : 1002 - 1003
  • [3] PYRIDINE-INDUCED SOLVENT SHIFTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF HYDROXYLIC COMPOUNDS
    DEMARCO, PV
    FARKAS, E
    DODDRELL, D
    MYLARI, BL
    WENKERT, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) : 5480 - &
  • [4] Two new lactones from Cephalotaxus fortunei var. alpnia
    Du, J
    Chiu, MH
    Nie, RL
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (12): : 1664 - 1665
  • [5] Cephanolides A-J, Cephalotane-Type Diterpenoids from Cephalotaxus sinensis
    Fan, Yao-Yue
    Xu, Jin-Biao
    Liu, Hong-Chun
    Gan, Li-She
    Ding, Jian
    Yue, Jian-Min
    [J]. JOURNAL OF NATURAL PRODUCTS, 2017, 80 (12): : 3160 - 3167
  • [6] The use of X-ray crystallography to determine absolute configuration
    Flack, H. D.
    Bernardinelli, G.
    [J]. CHIRALITY, 2008, 20 (05) : 681 - 690
  • [7] ON ENANTIOMORPH-POLARITY ESTIMATION
    FLACK, HD
    [J]. ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV): : 876 - 881
  • [8] Fu L G., 1999, Flora of China, V4, P89
  • [9] Cephalodiones A-D: Compound Characterization and Semisynthesis by [6+6] Cycloaddition
    Ge, Zhan-Peng
    Fan, Yao-Yue
    Deng, Wen-De
    Zheng, Cheng-Yu
    Li, Ting
    Yue, Jian-Min
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (17) : 9374 - 9378
  • [10] 17-nor-Cephalotane-Type Diterpenoids from Cephalotaxus fortunei
    Ge, Zhan-Peng
    Liu, Hong-Chun
    Wang, Guo-Cai
    Liu, Qun-Fang
    Xu, Cheng-Hui
    Ding, Jian
    Fan, Yao-Yue
    Yue, Jian-Min
    [J]. JOURNAL OF NATURAL PRODUCTS, 2019, 82 (06): : 1565 - 1575