Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri

被引：72
作者：
Allard, Pierre-Marie [1 ]
Leyssen, Pieter [2 ]
Martin, Marie-Therese [1 ]
Bourjot, Melanie [1 ]
Dumontet, Vincent [1 ]
Eydoux, Cecilia [3 ]
Guillemot, Jean-Claude [3 ]
Canard, Bruno [3 ]
Poullain, Cyril [1 ]
Gueritte, Francoise [1 ]
Litaudon, Marc [1 ]
机构：
[1] CNRS, LabEx LERMIT, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
[2] Katholieke Univ Leuven, Rega Inst Med Res, Lab Virol & Expt Chemotherapy, B-3000 Louvain, Belgium
[3] AFMB Aix Marseille Univ UMR7257, Lab Architecture & Fonct Macromol Biol, F-13288 Marseille, France
来源：
PHYTOCHEMISTRY | 2012年 / 84卷
关键词：
Trigonostemon cherrieri; Euphorbiaceae; Trigocherrin; Trigocherriolide; Daphnane; Chlorinated diterpenes; Antiviral; Chikungunya virus; Sindbis virus; Semliki forest virus; Dengue virus; PLANT; CONSTITUENTS;
D O I：
10.1016/j.phytochem.2012.07.023
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The chemical study of the bark and the wood of Trigonostemon cherrieri, a rare endemic plant of New Caledonia, led to the isolation of a series of highly oxygenated daphnane diterpenoid orthoesters (DDO) bearing an uncommon chlorinated moiety: trigocherrins A-F and trigocherriolides A-D. Herein, we describe the isolation and structure elucidation of the DDO (trigocherrins B-F and trigocherriolides A-D). We also report the antiviral activity of trigocherrins A, B and F (1, 2 and 6) and trigocherriolides A, B and C (7-9) against various emerging pathogens: chikungunya virus (CHIKV), Sindbis virus (SINV), Semliki forest virus (SFV) and dengue virus (DENV). (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：160 / 168
页数：9
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共 24 条
  • [11] Rediocides B-E, potent insecticides from Trigonostemon reidioides
    Jayasuriya, H
    Zink, DL
    Borris, RP
    Nanakorn, W
    Beck, HT
    Balick, MJ
    Goetz, MA
    Gregory, L
    Shoop, WL
    Singh, SB
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (02): : 228 - 231
  • [12] Structure and stereochemistry of rediocide A, a highly modified daphnane from Trigonostemon reidioides exhibiting potent insecticidal activity
    Jayasuriya, H
    Zink, DL
    Singh, SB
    Borris, RP
    Nanakorn, W
    Beck, HT
    Balick, MJ
    Goetz, MA
    Slayton, L
    Gregory, L
    Zakson-Aiken, M
    Shoop, W
    Singh, SB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) : 4998 - 4999
  • [13] Lotthanongine, an unprecedented flavonoidal indole alkaloid from the roots of Thai medicinal plant, Trigonostemon reidioides
    Kanchanapoom, T
    Kasai, R
    Chumsri, P
    Kraisintu, K
    Yamasaki, K
    [J]. TETRAHEDRON LETTERS, 2002, 43 (16) : 2941 - 2943
  • [14] STRUCTURE OF TRIGONOSTEMONE, A NEW PHENANTHRENONE FROM THE THAI PLANT TRIGONOSTEMON-REIDIOIDES
    KOKPOL, U
    THEBPATIPHAT, S
    BOONYARATAVEJ, S
    CHEDCHUSKULCAI, V
    NI, CZ
    CLARDY, J
    CHAICHANTIPYUTH, C
    CHITTAWONG, V
    MILES, DH
    [J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (05): : 1148 - 1151
  • [15] Trigonosins A-F, Daphnane Diterpenoids from Trigonostemon thyrsoideum
    Li, Shi-Fei
    Di, Ying-Tong
    Li, Shun-Lin
    Zhang, Yu
    Yang, Fu-Mei
    Sun, Qian-Yun
    Simo, James Mpetga
    He, Hong-Ping
    Hao, Xiao-Jiang
    [J]. JOURNAL OF NATURAL PRODUCTS, 2011, 74 (03): : 464 - 469
  • [16] Plant Orthoesters
    Liao, Shang-Gao
    Chen, Hua-Dong
    Yue, Jian-Min
    [J]. CHEMICAL REVIEWS, 2009, 109 (03) : 1092 - 1140
  • [17] Trigoxyphins A-G: Diterpenes from Trigonostemon xyphophylloides
    Lin, Bing-Dong
    Han, Mei-Ling
    Ji, Yin-Chun
    Chen, Hua-Dong
    Yang, Sheng-Ping
    Zhang, Sheng
    Geng, Mei-Yu
    Yue, Jian-Min
    [J]. JOURNAL OF NATURAL PRODUCTS, 2010, 73 (07): : 1301 - 1305
  • [18] Comparative mechanistic studies of de novo RNA synthesis by flavivirus RNA-dependent RNA polymerases
    Selisko, Barbara
    Dutartre, Helene
    Guillemot, Jean-Claude
    Debarnot, Claire
    Benarroch, Delphine
    Khromykh, Alexander
    Despres, Philippe
    Egloff, Marie-Pierre
    Canard, Bruno
    [J]. VIROLOGY, 2006, 351 (01) : 145 - 158
  • [19] Acaricidal daphnane diterpenoids from Trigonostemon reidioides (KURZ) CRAIB roots
    Soonthornchareonnon, N
    Sakayarojkul, M
    Isaka, M
    Mahakittikun, V
    Chuakul, W
    Wongsinkongman, P
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (02) : 241 - 243
  • [20] Three New Indole Alkaloids from Trigonostemon Iii
    Tan, Cheng-Jian
    Di, Ying-Tong
    Wang, Yue-Hu
    Zhang, Yu
    Si, Yi-Kang
    Zhang, Qiang
    Gao, Suo
    Hu, Xu-Jia
    Fang, Xin
    Li, Shi-Fei
    Hao, Xiao-Jiang
    [J]. ORGANIC LETTERS, 2010, 12 (10) : 2370 - 2373
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