Two Terpenoid Derivatives with Different 3/5/6/6/5-Fused Pentacyclic Skeletons from Hedyosmum orientale

被引：15
作者：
Fan, Yao-Yue [1 ,2 ,3 ]
Zheng, Cheng-Yu [1 ,3 ]
Zhou, Bin [1 ,2 ,3 ]
Zimbres, Flavia M. M. [4 ]
Cassera, Maria B. B. [4 ]
Yue, Jian-Min [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
[2] Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Shandong, Peoples R China
[3] Chinese Acad Med Sci, Res Units Discovery New Drug Lead Mol, Shanghai 201203, Peoples R China
[4] Univ Georgia, Ctr Trop & Emerging Global Dis CTEGD, Dept Biochem & Mol Biol, Athens, GA 30602 USA
来源：
CHINESE JOURNAL OF CHEMISTRY | 2023年 / 41卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Natural products; C-25; Terpenoids; Structure elucidation; Biosynthetic pathway hypothesis; Antimalarial activity; PLASMODIUM-FALCIPARUM; SESQUITERPENOIDS; MALARIA;
D O I：
10.1002/cjoc.202200597
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chemical investigation of Hedyosmum orientale led to the identification of two terpenoid derivatives, dyosmunoids A and B (1 and 2) featuring two different 3/5/6/6/5-fused pentacyclic ring systems, respectively. Compound 1 is the second natural product of this C-25 terpenoid compound class, and compound 2 is a rare dinor-C-25 terpenoid with a peroxide bridge. Their structural elucidation was achieved by the comprehensive analysis of spectroscopic data, single-crystal X-ray diffraction, and ECD calculation. Putative biosynthetic pathways for compounds 1 and 2 are proposed. Compound 2 exhibited strong antimalarial activity with an IC50 value of 0.42 mu mol.L-1.
引用
收藏
页码：392 / 398
页数：7
相关论文
共 29 条
  • [1] Natural products in drug discovery: advances and opportunities
    Atanasov, Atanas G.
    Zotchev, Sergey B.
    Dirsch, Verena M.
    Supuran, Claudiu T.
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2021, 20 (03) : 200 - 216
  • [2] Evidence of Artemisinin-Resistant Malaria in Africa
    Balikagala, Betty
    Fukuda, Naoyuki
    Ikeda, Mie
    Katuro, Osbert T.
    Tachibana, Shin-Ichiro
    Yamauchi, Masato
    Opio, Walter
    Emoto, Sakurako
    Anywar, Denis A.
    Kimura, Eisaku
    Palacpac, Nirianne M. Q.
    Odongo-Aginya, Emmanuel, I
    Ogwang, Martin
    Horii, Toshihiro
    Mita, Toshihiro
    [J]. NEW ENGLAND JOURNAL OF MEDICINE, 2021, 385 (13) : 1163 - 1171
  • [3] Enantioselective synthesis of an ophiobolin sesterterpene via a programmed radical cascade
    Brill, Zachary G.
    Grover, Huck K.
    Maimone, Thomas J.
    [J]. SCIENCE, 2016, 352 (6289) : 1078 - 1082
  • [4] Bruhn T., 2017, SpecDis
  • [5] SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra
    Bruhn, Torsten
    Schaumloeffel, Anu
    Hemberger, Yasmin
    Bringmann, Gerhard
    [J]. CHIRALITY, 2013, 25 (04) : 243 - 249
  • [6] Plasmodium falciparum Resistance to Artemisinin Derivatives and Piperaquine: A Major Challenge for Malaria Elimination in Cambodia
    Duru, Valentine
    Witkowski, Benoit
    Menard, Didier
    [J]. AMERICAN JOURNAL OF TROPICAL MEDICINE AND HYGIENE, 2016, 95 (06) : 1228 - 1238
  • [7] Horienoids A and B, Two Heterocoupled Sesquiterpenoid Dimers from Hedyosmum orientale
    Fan, Yao-Yue
    Gan, Li-She
    Chen, Shi-Xin
    Gong, Qi
    Zhang, Hai-Yan
    Yue, Jian-Min
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (16) : 11277 - 11283
  • [8] Hedyorienoids A and B, Two Sesquiterpenoid Dimers Featuring Different Polycyclic Skeletons from Hedyosmum orientale
    Fan, Yao-Yue
    Sun, Yi-Li
    Zhou, Bin
    Zhao, Jin-Xin
    Sheng, Li
    Li, Jing-Ya
    Yue, Jian-Min
    [J]. ORGANIC LETTERS, 2018, 20 (17) : 5435 - 5438
  • [9] Cephalotane-Type Norditerpenoids from Cephalotaxus fortunei var. alpina
    Ge, Zhan-Peng
    Zhou, Bin
    Zimbres, Flavia M.
    Cassera, Maria B.
    Zhao, Jin-Xin
    Yue, Jian-Min
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (10) : 1177 - 1184
  • [10] Visible-Light Photoredox Catalysis Enables the Biomimetic Synthesis of NyingchinoidsA, B, and D, and Rasumatranin D
    Hart, Jacob D.
    Burchill, Laura
    Day, Aaron J.
    Newton, Christopher G.
    Sumby, Christopher J.
    Huang, David M.
    George, Jonathan H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (09) : 2791 - 2794
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