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

Phytochemistry

Volumn 84, Issue , 2012, Pages 160-168

  Allard, Pierre Marie ^a   Leyssen, Pieter ^b   Martin, Marie Thérèse ^a   Bourjot, Mélanie ^a   Dumontet, Vincent ^a   Eydoux, Cécilia ^c   Guillemot, Jean Claude ^c   Canard, Bruno ^c   Poullain, Cyril ^a   Guéritte, Françoise ^a   Litaudon, Marc ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c Centre National de la Recherche Scientifique   (France)

Author keywords

Antiviral; Chikungunya virus; Chlorinated diterpenes; Daphnane; Dengue virus; Euphorbiaceae; Semliki forest virus; Sindbis virus; Trigocherrin; Trigocherriolide; Trigonostemon cherrieri

Indexed keywords

ANTIVIRUS AGENT; DITERPENE; ESTER;

ARTICLE; BARK; CHEMISTRY; CHIKUNGUNYA ALPHAVIRUS; CONFORMATION; DENGUE VIRUS; DRUG EFFECT; EUPHORBIACEAE; ISOLATION AND PURIFICATION; MICROBIAL SENSITIVITY TEST; SEMLIKI FOREST ALPHAVIRUS; SINDBIS VIRUS; WOOD;

ANTIVIRAL AGENTS; CHIKUNGUNYA VIRUS; DENGUE VIRUS; DITERPENES; ESTERS; EUPHORBIACEAE; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; PLANT BARK; SEMLIKI FOREST VIRUS; SINDBIS VIRUS; WOOD;

CHIKUNGUNYA VIRUS; DENGUE VIRUS; EUPHORBIACEAE; SEMLIKI FOREST VIRUS; SINDBIS VIRUS; TRIGONOSTEMON;

EID: 84868157945     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.07.023     Document Type: Article

References (23)

1. P.-M. Allard, E.T.H. Dau, C. Eydoux, J.-C. Guillemot, V. Dumontet, C. Poullain, B. Canard, F. Guéritte, and M. Litaudon Alkylated flavanones from the bark of Cryptocarya chartacea as dengue virus NS5 polymerase inhibitors J. Nat. Prod. 74 2011 2446 2453
2. P.-M. Allard, M.-T. Martin, M.-E. Tran Huu Dau, P. Leyssen, F. Guéritte, and M. Litaudon Trigocherrin A, the first natural chlorinated daphnane diterpene orthoester from Trigonostemon cherrieri Org. Lett. 14 2012 342 345
3. S.-C. Chan, M.-I. Chung, M.-H. Yen, G.-H. Lien, C.-N. Lin, and M.Y. Chiang Chingazumianine, a novel dichlorinated alkaloid from Corydalis koidzumiana Helv. Chim. Acta 83 2000 2993 2999
4. H.-D. Chen, X.-F. He, J. Ai, M.-Y. Geng, and J.-M. Yue Trigochilides A and B, two highly modified daphnane-type diterpenoids from Trigonostemon chinensis Org. Lett. 11 2009 4080 4083
5. H.-D. Chen, S.-P. Yang, X.-F. He, J. Ai, Z.-K. Liu, H.-B. Liu, M.-Y. Geng, and J.-M. Yue Trigochinins A-C: Three new daphnane-type diterpenes from Trigonostemon chinensis Org. Lett. 12 2010 1168 1171
6. H.-D. Chen, S.-P. Yang, X.-F. He, H.-B. Liu, J. Ding, and J.-M. Yue Trigochinins D-I: Six new daphnane-type diterpenoids from Trigonostemon chinensis Tetrahedron 66 2010 5065 5070
7. S.-H. Dong, H.-B. Liu, C.-H. Xu, J. Ding, and J.-M. Yue Constituents of Trigonostemon heterophyllus J. Nat. Prod. 74 2011 2576 2581
8. S.-H. Dong, C.-R. Zhang, C.-H. Xu, J. Ding, and J.-M. Yue Daphnane-type diterpenoids from Trigonostemon howii J. Nat. Prod. 74 2011 1255 1261
9. D. Fan, H. Ju, Y. Shao-Yong, C. Xia, Z. Da-Cai, and T. Ye-Na Trigonostemon tuberculatus (Euphorbiaceae), a peculiar new species from Yunnan Province, China Kew Bull. 65 2010 111 113
10. H. Jayasuriya, D.L. Zink, R.P. Borris, W. Nanakorn, H.T. Beck, M.J. Balick, M.A. Goetz, L. Gregory, W.L. Shoop, and S.B. Singh Rediocides B-E, potent insecticides from Trigonostemon reidioides J. Nat. Prod. 67 2004 228 231
11. H. Jayasuriya, D.L. Zink, S.B. Singh, R.P. Borris, W. Nanakorn, H.T. Beck, M.J. Balick, M.A. Goetz, L. Slayton, L. Gregory, M. Zakson-Aiken, W. Shoop, and S.B. Singh Structure and stereochemistry of rediocide A, a highly modified daphnane from Trigonostemon reidioides exhibiting potent insecticidal activity J. Am. Chem. Soc. 122 2000 4998 4999
12. T. Kanchanapoom, R. Kasai, P. Chumsri, K. Kraisintu, and K. Yamasaki Lotthanongine, an unprecedented flavonoidal indole alkaloid from the roots of Thai medicinal plant, Trigonostemon reidioides Tetrahedron Lett. 43 2002 2941 2943
13. U. Kokpol, S. Thebpatiphat, S. Boonyaratavej, V. Chedchuskulcai, C.-Z. Ni, J. Clardy, C. Chaichantipyuth, V. Chittawong, and D.H. Miles Structure of trigonostemone, a new phenanthrenone from the thai plant Trigonostemon reidioides J. Nat. Prod. 53 1990 1148 1151
14. S.-F. Li, Y.-T. Di, S.-L. Li, Y. Zhang, F.-M. Yang, Q.-Y. Sun, J.M. Simo, H.P. He, and X.J. Hao Trigonosins A-F, daphnane diterpenoids from Trigonostemon thyrsoideum J. Nat. Prod. 74 2011 464 469
15. S.-G. Liao, H.-D. Chen, and J.-M. Yue Plant orthoesters Chem. Rev. 109 2009 1092 1140
16. B.-D. Lin, M.-L. Han, Y.-C. Ji, H.-D. Chen, S.-P. Yang, S. Zhang, M.-Y. Geng, and J.-M. Yue Trigoxyphins A-G: Diterpenes from Trigonostemon xyphophylloides J. Nat. Prod. 73 2010 1301 1305
17. B. Selisko, H. Dutartre, J.-C. Guillemot, C. Debarnot, D. Benarroch, A. Khromykh, P. Desprès, M.-P. Egloff, and B. Canard Comparative mechanistic studies of de novo RNA synthesis by flavivirus RNA-dependant RNA polymerases Virology 351 2006 145 158
18. N. Soonthornchareonnon, M. Sakayarojkul, M. Isaka, V. Mahakittikun, W. Chuakul, and P. Wongsinkongman Acaricidal daphnane diterpenoids from Trigonostemon reidioides (KURZ) CRAIB roots Chem. Pharm. Bull. 53 2005 241 243
19. C.-J. Tan, Y.-T. Di, Y.-H. Wang, Y. Zhang, Y.-K. Si, Q. Zhang, S. Gao, X.-J. Hu, X. Fang, S.-F. Li, and X.-J. Hao Three new indole alkaloids from Trigonostemon lii Org. Lett. 12 2010 2370 2373
20. V.S. Watts, and J.H. Goldstein A maximum overlap orbital calculation of 13C-H coupling constants in the vinyl halides Theor. Chim. Acta 4 1966 265 272
21. L. Zhang, R.H. Luo, F. Wang, Z.J. Dong, L.M. Yang, Y.T. Zheng, and J.K. Liu Daphnane diterpenoids isolated from Trigonostemon thyrsoideum as HIV-1 antivirals Phytochemistry 71 2010 1879 1883
22. L. Zhang, R.-H. Luo, F. Wang, M.-Y. Jiang, Z.-J. Dong, L.-M. Yang, Y.-T. Zheng, and J.K. Liu Highly functionalized daphnane diterpenoids from Trigonostemon thyrsoideum Org. Lett. 12 2010 152 155
23. Q. Zhu, C.-P. Tang, C.-Q. Ke, X.-Q. Li, J. Liu, L.-S. Gan, H.-C. Weiss, E.-R. Gesing, and Y. Ye Constituents of Trigonostemon chinensis J. Nat. Prod. 73 2010 40 44