TNF-α inhibitory diterpenoids from the Chinese mangrove plant Excoecaria agallocha L.

Phytochemistry

Volumn 71, Issue 17-18, 2010, Pages 2124-2131

  Li, Yongxin ^a   Liu, Jun ^a   Yu, Shanjiang ^b   Proksch, Peter ^c   Gu, Jun ^a   Lin, Wenhan ^a  

^a PEKING UNIVERSITY   (China)

^b China National Center for Biotechnology Development   (China)

^c HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Agallochaols K Q; Anti inflammatory activity; Euphorbiaceae; Excoecaria agallocha L.; Mangrove plant; Structure elucidation

Indexed keywords

AGALLOCHAOL Q; DITERPENE; HERBACEOUS AGENT; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERLEUKIN 6; KAURANE DERIVATIVE; LIPOPOLYSACCHARIDE; NONSTEROID ANTIINFLAMMATORY AGENT; TUMOR NECROSIS FACTOR ALPHA;

ANIMAL; ARTICLE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; EUPHORBIA; ISOLATION AND PURIFICATION; MACROPHAGE; MOUSE; NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DITERPENES; DITERPENES, KAURANE; DRUGS, CHINESE HERBAL; EUPHORBIACEAE; INTERLEUKIN-6; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; NF-KAPPA B; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; TUMOR NECROSIS FACTOR-ALPHA;

EUPHORBIA; EUPHORBIACEAE; EXCOECARIA AGALLOCHA;

EID: 78249270700     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.08.011     Document Type: Article

References (34)

1. A.S.R. Anjaneyulu, and V.L. Rao Seco diterpenoids from Excoecaria agallocha L. Phytochemistry 62 2003 585 589
2. A. Castrillo, B. de las Heras, S. Hortelano, B. Rodriguez, A. Villar, and L. Bosca Inhibition of nuclear factor κB (NF-κB) pathway by tetracyclic kaurene diterpenes in macrophages. Special effects on NF-κB-inducing kinase activity and on the coordinate activation of ERK and p38 MAPK J. Biol. Chem. 276 2001 15854 15860
3. K.L. Erickson, J.A. Beutler, J.H. Cardellina II, and J.B. McMahon A novel phorbol ester from Excoecaria agallocha L J. Nat. Prod. 58 1995 769 772
4. M.H. Grace, J.A. Faraldos, M.A. Lila, and R.M. Coates ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia Phytochemistry 68 2007 546 553
5. S. Habtemariam, A.L. Gray, C. Lavaud, G. Massiot, B.W. Skelton, P.G. Waterman, and A.H. White ent-12-Oxolabda-8, 13(16)-dien-l5-oic acid and ent-8β, 12α-epidioxy-l2β-hydroxylabda-9(11), 13-dien-15-oic acid γ-lactone: two new diterpenes from the aerial parts of Premna oligotricha J. Chem. Soc. Perkin Trans. 1 1991 893 896
6. D.K. Kahlon, T.A. Lansdell, J.S. Fisk, C.D. Hupp, T.L. Friebe, S. Hovde, A.D. Jones, R.D. Dyer, R.W. Henry, and J.J. Tepe Nuclear factor-κB mediated inhibition of cytokine production by imidazoline scaffolds J. Med. Chem. 52 2009 1302 1309
7. J. Kang, R. Chen, and D. Yu A new isopimarane-type diterpene and a new natural atisanetype diterpene from Excoecaria agallocha J. Asian Nat. Prod. Res. 7 2005 729 734
8. M.V. Karamouzis, P.A. Konstantinopoulos, and A.G. Papavassiliou1 The activator protein-1 transcription factor in respiratory epithelium carcinogenesis Mol. Cancer Res. 5 2007 109 120
9. T. Konishi, Y. Fujiwara, T. Konishima, and S. Kiyosawa Five new labdane-type diterpenes from Excoecaria agallocha L. Chem. Pharm. Bull. 46 1998 1393 1398 (Pubitemid 28455244)
10. A.I. Laskin, P. Grabowich, C.L. Meyers, and J. Fried Transformations of eburicoic acid. V. Cleavage of ring A by the fungus Glomerella fusarioides J. Med. Chem. 7 1964 406 409
11. J.H. Lee, T.H. Koo, B.Y. Hwang, and J.J. Lee Kaurane diterpene, kamebakaurin, inhibits NF-κB by directly targeting the DNA-binding activity of p50 and blocks the expression of antiapoptotic NF-κB target gene J. Biol. Chem. 277 2002 18411 18420
12. C. Leung, S.P. Grill, W. Lam, W. Gao, H. Sun, and Y. Cheng Eriocalyxin B inhibits nuclear factor-κB activation by interfering with the binding of both p65 and p50 to the response element in a noncompetitive Manner Mol. Pharmacol. 70 2006 1946 1955
13. J.J. Li, L.W. Oberley, M. Fan, and N.H. Colburn Inhibition of Ap-1 and NF-κB by manganese-containing superoxide dismutase in human breast cancers FASEB J. 12 1998 1713 1723
14. X. Li, J. Lei, Y. Zheng, S. Isabel, and W. Lin New entisopimarane diterpene from mangrove Excoecaria agallocha L. Chem. Res. Chin. Uni. 23 2007 541 543
15. G. Liu, R. Muler, and P. Rudi Chemical transformations of phyllocladane (=13β-kaurane) diterpenoids Helv. Chim. Acta 86 2003 420 438
16. H. Ohhigashi, H. Katsumata, K. Kawazu, K. Koshimizu, and T. Mitsui A piscicidal constituent of Excoecaria agallocha Agric. Biol. Chem. 38 1974 1093 1095
17. G. Palazzino, E. Federici, P. Rasoanaivo, and C. Galeffi 3,4-Seco diterpenes of Croton geayi Gazz. Chim. Ital. 127 1997 311 314
18. S. Prakash, M.A. Khan, H. Khan, and A. Zaman A piperidine alkaloid from Excoecaria agallocha Phytochemistry 22 1983 1836 1837
19. A. Rashtchian Amplification of RNA Genome Res. 4 1994 S83 S91
20. N.H. Ruddle Tumor necrosis factor (TNF-α) and lymphotoxin (TNF-β) Curr. Opin. Immunol. 4 1992 327 332
21. A. Salminen, M. Lehtonen, T. Suuronen, K. Kaarniranta, and J. Huuskonen Terpenoids: natural inhibitors of NF-κB signaling with anti-inflammatory and anticancer potential Cell. Mol. Life Sci. 65 2008 2979 2999
22. N. Shirane, Y. Hashimoto, K. Ueda, H. Takenaka, and K. Katoh Ring-A cleavage of 3-oxo-olean-12-en-28-oic acid by the fungus Chaetomium longirostre Phytochemistry 43 1996 99 104
23. M. Suganuma, S. Okabe, Y. Kai, N. Sueoka, E. Sueoka, and H. Fujiki Synergistic effects of (-)-epigallocatechin gallate with (-)-epicatechin, sulindac, or tamoxifen on cancer-preventive activity in the human lung cancer cell line PC-9 Cancer Res. 59 1999 44 47
24. K. Tenji, A. Masuji, I. Rie, K. Shiu, F. Yasuhiro, and S. Yasuo Three new labdane-type diterpenes from wood, Excoecaria agallocha Chem. Pharm. Bull. 44 1996 229 231
25. J. Wang, W. Xiang, and Y. Guo Agallochaols A and B, two new diterpenes from the Chinese mangrove Excoecaria agallocha Helv. Chim. Acta 87 2004 2829 2833
26. J. Wang, W. Xiang, and Y. Guo Secoatisane- and isopimarane-tpye diterpenoids from the Chinese mangrove Excoecaria agallocha L. Helv. Chim. Acta 88 2005 979 985
27. J. Wang, Z. Li, W. Xiang, and Y. Guo Further new secoatisane diterpenoids from the Chinese mangrove Excoecaria agallocha L. Helv. Chim. Acta 89 2006 1367 1372
28. J. Wang, W. Zhang, Z. Li, W. Xiang, Y. Guo, and K. Krohn Elucidation of excogallochaols A-D, four unusual diterpenoids from the Chinese mangrove Excoecaria agallocha Phytochemistry 68 2007 2426 2431
29. J. Wang, S. Wu, M. Li, S. Chen, J.L. Telling, V.H. Perry, and J. Gu Retinoic acid-inducible gene-I mediates late phase induction of TNF-α by lipopolysaccharide J. Immunol. 180 2008 8011 8019
30. Z. Wang, Y. Lin, D. Feng, C. Ke, P. Lin, C. Yan, and J. Chen A new atisane-type diterpene from the bark of the mangrove plant Excoecaria agallocha Molecules 14 2009 414 422
31. 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
32. B. Yin, L. Shen, M. Zhang, L. Zhao, Y. Wang, C. Huo, and Q. Shi Chemical constituents of plants from the genus excoecaria Chem. Biodiver. 5 2008 2356 2371
33. C. Zdero, F. Bohlmann, and R.M. King Guaianolides and labdanes from Brickellia species Phytochemistry 30 1991 1591 1595
34. W. Zhu, J.S. Downey, Y. Li, and J. Han Co-ordinated regulation of TNF expression by multiple MAP kinase pathways J. Endotoxin Res. 5 1999 239 243