Anti-HIV-1 tigliane diterpenoids from Excoecaria acertiflia Didr

Fitoterapia

Volumn 95, Issue , 2014, Pages 34-41

  Huang, Sheng Zhuo ^a,b   Zhang, Xuan ^c   Ma, Qing Yun ^a   Peng, Hua ^b   Zheng, Yong Tang ^c   Hu, Jiang Miao ^b   Dai, Hao Fu ^a   Zhou, Jun ^b   Zhao, You Xing ^a  

^a INSTITUTE OF TROPICAL BIOSCIENCE AND BIOTECHNOLOGY   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

^c KUNMING INSTITUTE OF ZOOLOGY   (China)

Author keywords

Anti HIV 1; Chemotaxonomy; Euphorbiaceae; Excoecafolin; Excoecaria acerifolia

Indexed keywords

ALCOHOL; ANTIVIRUS AGENT; DITERPENOID; EXCOECAFOLINS A; EXCOECAFOLINS B; EXCOECAFOLINS C; EXCOECAFOLINS D; EXCOECAFOLINS E; EXCOECARIA ACERTIFLIA EXTRACT; PLANT EXTRACT; TIGLIANE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DITERPENE; HERBACEOUS AGENT; MEZEREIN;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMOTAXONOMY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; EUPHORBIACEAE; EXCOECARIA ACERTIFLIA; HETERONUCLEAR MULTIPLE BOND CORRELATION; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THYMELAEACEAE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT STEM;

ANTI-HIV AGENTS; DITERPENES; DRUGS, CHINESE HERBAL; EUPHORBIACEAE; HIV-1; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANT STEMS; PLANTS, MEDICINAL;

EID: 84896536380     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2014.02.018     Document Type: Article

References (44)

1. P.F. Stevens Angiosperm phylogeny website 2001 University of Missouri St Louis [onwards]
2. D.J. Maberley The plant-book 2nd ed. 1997 Cambridge University Press Cambridge 771 781
3. Takhtajan Diversity and classification of flowering plants 1997 Columbia University Press New York 1 643
4. C.Y. Wu, A.M. Lu, T. YanCheng, C.Z. Rui, and D.Z. Li The families and genera of Angiosperms in China 2003 Science Press Beijing 588 592
5. G. Erdtman Pollen morphology and plant taxonomy-Angiosperms 1952 Chronica Botanica Co. Waltham, MA 431 433
6. R.F. Throne Synopsis of a putatively phylogenetic calssification of the flowering plants Aloso 65 1968 6 66
7. P. Wiriyachitra, H. Hajiwangoh, P. Boonton, W. Adolf, H.J. Opferkuch, and E. Hecker Investigations of medicinal plants of Euphorbiaceae and Thymelaeaceae occurring and used in Thailand; II. Cryptic irritants of the diterpene ester type from Three Excoecaria species Planta Med 51 1985 368 371
8. T. Okuda, T. Yoshida, S. Koike, and N. Toh New diterpene esters from Aleurites fordii fruits Phytochemistry 14 1975 509 515
9. M.E.F. Hegazy, A.E.H.H. Mohamed, N. Aoki, T. Ikeuchi, E. Ohta, and S. Ohta Bioactive jatrophane diterpenes from Euphorbia guyoniana Phytochemistry 71 2010 249 253
10. Y. Li, J. Liu, S. Yu, P. Proksch, J. Gu, and W. Lin TNF-α inhibitory diterpenoids from the Chinese mangrove plant Excoecaria agallocha L Phytochemistry 71 2010 2124 2131
11. Y. Shiono, M. Kikuchi, T. Koseki, T. Murayama, E. Kwon, and N. Aburai Isopimarane diterpene glycosides, isolated from endophytic fungus Paraconiothyrium sp. MY-42 Phytochemistry 72 2011 1400 1405
12. J.D. Wang, W. Zhang, Z.Y. Li, W.S. Xiang, Y.W. Guo, and K. Krohn Elucidation of excogallochaols A-D, four unusual diterpenoids from the Chinese mangrove Excoecaria agallocha Phytochemistry 68 2007 2426 2431 (Pubitemid 47429715)
13. S.Z. Huang, X.J. Zhang, X.Y. Li, L.M. Kong, H.Z. Jiang, and Q.Y. Ma et al. Daphnane-type diterpene esters with cytotoxic and anti-HIV-1 activities from Daphne acutiloba Rehd Phytochemistry 75 2012 99 107
14. W. He, M. Cik, G. Appendino, L. Van Puyvelde, J.E. Leysen, and N. De Kimpe Daphnane-type diterpene orthoesters and their biological activities Mini-Rev Med Chem 2 2002 185 200
15. S.G. Liao, H.D. Chen, and J.M. Yue Plant orthoesters Chem Rev 109 2009 1092 1140 [Washington, DC, United States]
16. Yunnan Institute of Meteria Medica The annals of national medicine in Yunnan 2009 The Nationalities Publishing House of Yunnan Kunming 217 218
17. Y.L. Zhao, Q.X. He, Y. Li, S.F. Wang, K.C. Liu, and Y.P. Yang et al. Chemical constituents of Excoecaria acerifolia and their bioactivities Molecules 15 2010 2178 2186
18. S.Z. Huang, Q.Y. Ma, W.W. Fang, F.Q. Xu, H. Peng, and H.F. Dai et al. Three new isopimarane diterpenoids from Excoecaria acerifolia J Asian Nat Prod Res 15 2013 750 755
19. S.Z. Huang, X. Zhang, Q.Y. Ma, Y.T. Zheng, F.Q. Xu, and H. Peng et al. Terpenoids and their anti-HIV-1 activities from Excoecaria acerifolia Fitoterapia 91C 2013 224 230
20. L.J. Reed, and H. Muench A simple method for estimating fifty percent endpoints Am J Hyg 27 1938 493 497
21. W. Adolf, and E. Hecker On the active principles of the Thymelaeaceae. II. Skin irritant and cocarcinogenic diterpenoid factors from Daphnopsis racemosa Planta Med 45 1982 177 182 (Pubitemid 13212169)
22. M.J. Koury, A. Balmain, and I.B. Pragnell Induction of granulocyte-macrophage colony-stimulating activity in mouse skin by inflammatory agents and tumor promoters EMBO J 2 1983 1877 1882
23. V. Armuth, I. Berenblum, W. Adolf, H.J. Opferkuch, R. Schmidt, and B. Sorg et al. Systemic promoting action and leukemogenesis in SWR mice by phorbol and structurally related polyfunctional diterpenes J Can Res Clin Oncol 95 1979 19 28 (Pubitemid 10233671)
24. W. Adolf, and E. Hecker On the active principles of the spurge family, X. Skin irritants, cocarcinogens, and cryptic cocarcinogens from the latex of the manchineel tree J Nat Prod 47 1984 482 496 (Pubitemid 14093174)
25. Y.R. Xu, Y.K. Li, J.L. Cao, X. Zhang, G.Y. Yang, and Q.F. Hu A new daphne diterpenoids from Daphne acutiloba Rehd Asian J Chem 22 2010 6371 6374
26. W.H. Ma, H. Huang, P. Zhou, D.F. Chen, and A.-C. Schisanwilsonenes Anti-HBV carotane sesquiterpenoids from the fruits of Schisandra wilsoniana J Nat Prod 72 2009 676 678
27. H. Heymann, Y. Tezuka, T. Kikuchi, and S. Supriyatna Constituents of Sindora sumatrana Miq. I. Isolation and NMR spectral analysis of sesquiterpenes from the dried pods Chem Pharm Bull 42 1994 138 146 (Pubitemid 24067522)
28. S. Kogiso, S. Hosozawa, K. Wada, and K. Munakata Daphneolone in roots of Daphne odora Phytochemistry 13 1974 2332 2334
29. Z. Lin-Gen, O. Seligmann, and H. Wagner Daphneticin, a coumarinolignoid from Daphne tangutica Phytochemistry 22 1983 617 619
30. J.F. Xu, Z.M. Feng, J. Liu, and P.C. Zhang New hepatoprotective coumarinolignoids from Mallotus apelta Chem Biodivers 5 2008 591 597
31. W.H. Lin, Z.W. Deng, H.M. Lei, H.Z. Fu, and J. Li Polyphenolic compounds from the leaves of Koelreuteria paniculata Laxm J Asian Nat Prod Res 4 2002 287 295 (Pubitemid 35285346)
32. H.B. Liu, H. Zhang, J.H. Yu, C.H. Xu, J. Ding, and J.M. Yue Cytotoxic diterpenoids from Sapium insigne J Nat Prod 75 2012 722 727
33. E. Stanoeva, W. He, and N. De Kimpe Natural and synthetic cage compounds incorporating the 2,9,10-trioxatricyclo[4.3.1.03,8]decane type moiety Bioorg Med Chem 13 2004 17 28 (Pubitemid 39575688)
34. H. Ohigashi, M. Hirota, T. Ohtsuka, K. Koshimizu, H. Fujiki, and M. Suganuma et al. Resiniferonol-related diterpene esters from Daphne odora Thunb. and their ornithine decarboxylase-inducing activity in mouse skin Agric Biol Chem 46 1982 2605 2608 (Pubitemid 13202472)
35. R.A. Fernandes, and A.K. Chowdhury Stereoselective total synthesis of (+)-nephrosteranic acid and (+)-roccellaric acid through asymmetric dihydroxylation and Johnson-Claisen rearrangement Eur J Org Chem 2011 1106 1112 [S/1-S/9]
36. S. Yaragorla, and R. Muthyala Concise total synthesis of cytotoxic natural products (+) and (-)-muricatacin 2010 ARKIVOC Gainesville, FL, United States 178 184
37. R.P. Borris, G. Blaskó, and G.A. Cordell Ethnopharmacologic and phytochemical studies of the Thymelaeaceae J Ethnopharmacol 24 1988 41 91
38. W.C. Xu, J.G. Shen, and J.Q. Jiang Phytochemical and biological studies of the plants from the genus Daphne Chem Biodivers 8 2011 1215 1233
39. C. Karalai, P. Wiriyachitra, H.J. Opferkuch, and E. Hecker Cryptic and free skin irritants of the daphnane and tigliane types in latex of Excoecaria agallocha Planta Med 60 1994 351 355 (Pubitemid 24255931)
40. C. Karalai, P. Wiriyachitra, B. Sorg, and E. Hecker Improved access to highly unsaturated skin irritants of the daphnane type from latex of Excoecaria oppositifolia Planta Med 60 1994 566 568 (Pubitemid 24382570)
41. K.L. Erickson, J.A. Beutler, J.H. Cardellina, J.B. McMahon, D.J. Newman, and M.R. Boyd HIV-inhibitory natural products. 22. A novel phorbol ester from Excoecaria agallocha J Nat Prod 58 1995 769 772
42. J. Weber, and E. Hecker Cocarcinogens of the diterpene ester type from Croton flavens L. and esophageal cancer in Curacao Experientia 34 1978 679 682 (Pubitemid 8346019)
43. H. Schewe, D. Holtmann, and J. Schrader P450BM-3-catalyzed whole-cell biotransformation of α-pinene with recombinant Escherichia coli in an aqueous-organic two-phase system Appl Microbiol Biotechnol 83 2009 849 857
44. J. MacMillan, M.H. Beale, M.C. Otto, B. Derek, and N. Koji Diterpene biosynthesis Comprehensive natural products chemistry 1999 Pergamon Oxiford 217