Daphnane diterpenoids isolated from Trigonostemon thyrsoideum as HIV-1 antivirals

Phytochemistry

Volumn 71, Issue 16, 2010, Pages 1879-1883

  Zhang, Ling ^a,c   Luo, Rong Hua ^b   Wang, Fei ^a   Dong, Ze Jun ^a   Yang, Liu Meng ^b   Zheng, Yong Tang ^b   Liu, Ji Kai ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b KUNMING INSTITUTE OF ZOOLOGY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Anti HIV 1; Daphnane diterpenoids; Euphorbiaceae; Trigonostemon thyrsoideum; Trigonothyrins D G

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DITERPENE; HERBACEOUS AGENT; MEZEREIN; TRIGONOTHYRIN D; TRIGONOTHYRIN E;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; EUPHORBIA; HUMAN IMMUNODEFICIENCY VIRUS 1; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; PLANT STEM;

ANTI-HIV AGENTS; DITERPENES; DRUGS, CHINESE HERBAL; EUPHORBIACEAE; HIV-1; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT STEMS;

EUPHORBIA; EUPHORBIACEAE; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; TRIGONOSTEMON;

EID: 77957852857     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.08.008     Document Type: Article

References (24)

1. W. Adolf, and E. Hecker On the active principles of the spurge family X. Skin irritants, cocarcinogens, and cryptic carcinogens from the latex of the manchineel tree J. Nat. Prod. 47 1984 482 496 (Pubitemid 14093174)
2. J.R. Carney, J.M.R. Krenisky, T. Williamson, J. Luo, T.J. Carlson, V.L. Hsu, and J.L. Moswa A new daphnane diterpenoid with potent antihyperglycemic activity from Maprounea africana J. Nat. Prod. 62 1999 345 347 (Pubitemid 29137930)
3. 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
4. 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
5. Editorial Committee of Flora Reipublicae Popularis Sinicae, Flora Reipublicae Popularis Sinicae, vol. 44, Academic Press, Beijing, 1997, pp. 162-163.
6. W.D. He, M. Cik, A. Lesage, I.V.D. Linden, N.D. Kimpe, G. Appendino, J. Bracke, S.G. Mathenge, F.P. Mudida, J.E. Leysen, and L.V. Puyvelde Kirkinine, a new daphnane orthoester with potent neurotrophic activity from Synaptolepis kirkii J. Nat. Prod. 63 2000 1185 1187
7. W. He, M. Cik, G. Appendino, L.V. Puyvelde, J.E. Leysen, and N.D. Kimpe Daphnane-type diterpene orthoesters and their biological activities Mini-Rev. Med. Chem. 2 2002 185 200
8. W. He, M. Cik, L.V. Puyvelde, J.V. Dun, G. Appendino, A. Lesage, I.V. Lindin, J.E. Leysen, W. Wouters, S.G. Mathenge, F.P. Mudida, and N.D. Kimpe Neurotrophic and antileukemic daphnane diterpenoids from Synaptolepis kirkii Bioorg. Med. Chem. 10 2002 3245 3255 (Pubitemid 34855398)
9. X.J. Hu, Y.H. Wang, L.Y. Kong, H.P. He, S. Gao, H.Y. Liu, J. Ding, H. Xie, Y.T. Di, and X.J. Hao New phenanthrenes from Trigonostemon lii Y.T. Chang Tetrahedron Lett. 50 2009 2917 2919
10. 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 (Pubitemid 30347050)
11. 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 (Pubitemid 38282914)
12. T. Kanchanapoom, R. Kasai, P. Chumsri, K. Kraisintud, and K. Yamasakia Lotthanongine, an unprecedented flavonoidal indole alkaloid from the roots of Thai medicinal plant, Trigonostemon reidioides Tetrahedron Lett. 43 2002 2941 2943 (Pubitemid 34286493)
13. R. Kasai, K.H. Lee, and H.C. Huang Genkwadaphnin, a potent antileukemic diterpene from Daphne genkwa Phytochemistry 20 1981 2592 2594
14. 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
15. S.G. Liao, H.D. Chen, and J.M. Yue Plant orthoesters Chem. Rev. 109 2009 1092 1140
16. B.Y. Park, B.S. Min, K.S. Ahn, O.K. Kwon, H. Joung, K.H. Bae, H.K. Lee, and S.R. Oh Daphnane diterpene esters isolated from flower buds of Daphne genkwa induce apoptosis in human myelocytic HL-60 cells and suppress tumor growth in Lewis lung carcinoma (LLC)-inoculated mouse model J. Ethnopharmacol. 111 2007 496 503 (Pubitemid 46617088)
17. 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 (Pubitemid 40873695)
18. 3, 8]decane type moiety Bioorg. Med. Chem. 13 2005 17 28 (Pubitemid 39575688)
19. A. Tempeam, N. Thasana, C. Pavaro, W. Chuakul, P. Siripong, and S. Ruchirawat A new cytotoxic daphnane diterpenoid, rediocide G, from Trigonostemon reidioides Chem. Pharm. Bull. 53 2005 1321 1323 (Pubitemid 41425630)
20. M.I. Tyler, and M.E.H. Howden Antineoplastic and piscicidal 1-alkyldaphnane orthoesters from Pimelea species J. Nat. Prod. 48 1985 440 445
21. S. Yin, Z.S. Su, Z.W. Zhou, L. Dong, and J.M. Yue Antimicrobial diterpenes from Trigonostemon chinensis J. Nat. Prod. 71 2008 1414 1417
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. Y.T. Zheng, K.L. Ben, F. Zhang, and J.H. Wang In vitro immunotoxicity and cytotoxicity of trichosanthin against human normal immunocytes and leukemia-lymphoma cells Immunopharm. Immunotoxicol. 17 1995 69 79
24. Y.T. Zheng, K.L. Ben, and S.W. Jin Alpha-momorcharin inhibits HIV-1 replication in acutely but not chronically infected T-lymphocytes Acta Pharmacol. Sin. 20 1999 239 243