A sesquiterpene quinone, 5-Epi-smenospongine, promotes TNF-α production in LPS-stimulated RAW 264.7 cells

Marine Drugs

Volumn 5, Issue 4, 2007, Pages 151-156

  Oda, Taiko ^a   Wang, Weifang ^b   Ukai, Kazuyo ^b   Nakazawa, Takahiro ^b   Mochizuki, Masataka ^a  

^a KEIO UNIVERSITY   (Japan)

^b TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Hippospongia sp.; Marine sponge; RAW 264.7 cells; Sesquiterpene quinone; TNF production

Indexed keywords

5 EPI SMENOSPONGINE; ILIMAQUINONE; INTERLEUKIN 8; LIPOPOLYSACCHARIDE; QUINONE DERIVATIVE; SESQUITERPENE DERIVATIVE; SMENOSPONGIARINE; SMENOSPONGIDINE; SMENOSPONGINE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME SYNTHESIS; MOUSE; NONHUMAN; SPONGE (PORIFERA);

HIPPOSPONGIA;

EID: 37749047145     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md504151     Document Type: Article

References (22)

1. Luibrand, R.T.; Erdman, T.R.; Vollmer, J.J.; Scheuer, P.J.; Finer, J.; Clardy, J. Ilimaquinone, a sesquiterpenoid quinone from a marine sponge. Tetrahedron 1979, 35, 609-612.
2. Capon, R.J.; MacLeod, J.K. A revision of the absolute stereochemistry of ilimaquinone. J. Org. Chem. 1987, 52, 5059-5060.
3. Carté, B.; Rose, C.B.; Faulkner, D.J. 5-epi-Ilimaquinone, a metabolite of the sponge Fenestraspongia Sp. J. Org. Chem. 1985, 50, 2785-2787.
4. Rodríguez, J.; Quiñoá, E.; Riguera, R.; Peters, B. M.; Abrell, L.M.; Crews, P. The structures and stereochemistry of cytotoxic sesquiterpene quinones from Dactylospongia elegans. Tetrahedron 1992, 48, 6667-6680.
5. Kondracki, M-L.; Guyot, M. Biologically active quinone and hydroquinone sesquiterpenoids from the sponge Smenospongia sp. Tetrahedron 1989, 45, 1995-2004.
6. Kondracki, M-L.; Guyot, M. Smenospongine: a cytotoxic and antimicrobial aminoquinone isolated from Smenospongia sp. Tetrahedron Lett. 1987, 28, 5815-5818.
7. Mitome, H.; Nagasawa, T.; Miyaoka, H.; Yamada, Y. van Soest, R.W. Dactyloquinones A and B, new sesquiterpenoid quinones from the Okinawan marine sponge Dactylospongia elegans. J. Nat. Prod. 2001, 64, 1506-1508.
8. Salmoun, M.; Devijver, C.; Daloze, D.; Braekman, J.C.; Gomez, R.; de Kluijver, M.; van Soest, R.W.M. New sesquiterpene/quinones from two sponges of the genus Hyrtios. J. Nat. Prod. 2000, 63, 452-456.
9. Kwak, J.H.; Schmitz, F.J.; Kelly, M. Sesquiterpene quinols/quinones from the Micronesian sponge Petrosaspongia metachromia. J. Nat. Prod. 2000, 63, 1153-1156.
10. Oda, T.; Wang, W.; Fujita, A.; Mochizuki, M.; Ukai, K.; Namikoshi, M. Promotion of IL-8 production in PMA-stimulated HL-60 cells by sesquiterpene quinones from a marine sponge Hippospongia sp. J. Nat. Med. 2007, 61, 434-437.
11. Graves, D.T.; Jiang, Y. Chemokines, a family of chemotactic cytokines. Crit. Rev. Oral Biol. Med. 1995, 6, 109-118.
12. di Celle, P.F.; Carbone, A.; Marchis, D.; Zhou, D.; Sozzani, S.; Zupo, S.; Pini, M.; Mantovani, A.; Foa, R. Cytokine gene expression in B-cell chronic lymphocytic leukemia: evidence of constitutive interleukin-8 (IL-8) mRNA expression and secretion of biologically active IL-8 protein. Blood 1994, 84, 220-228.
13. Green, A.R.; Green, V. L.; White, M.C.; Speirs, V. Expression of Cytokine messenger RNA in normal and neoplastic human breast tissue: identification of interleukin-8 as a potential regulatory factor in breast tumours. Int. J. Cancer 1997, 72, 937-941.
14. Konig, B.; Steinbach, F.; Janocha, B.; Drynda, A.; Stumm, M.; Philipp, C.; Allhoff, E.P.; Konig, W. The differential expression of proinflammatory cytokines IL-6, IL-8 and TNF-alpha in renal cell carcinoma. Anticancer Res. 1999, 19, 1519-1524.
15. Galffy, G.; Mohammed, K.A.; Dowling, P.A.; Nasreen, N.; Ward, M. J.; Antony, V.B. Interleukin 8: an autocrine growth factor for malignant mesothelioma. Cancer Res. 1999, 59, 367-371.
16. Carmichael, J.; DeGraff, W.G.; Gazdar, A.F.; Minna, J.D.; Mitchell, J.B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 1987, 47, 936-942.
17. Prokofeva, N.G.; Utkina, N.K.; Chaikina, E.L.; Makarchenko, A.E. Biological activities of marine sesquiterpenoid quinones: structure-activity relationships in cytotoxic and hemolytic assays. Comp. Biochem. Physiol. Bio. Mol. Biol. 2004, 139, 169-173.
18. Tziveleka, L.A.; Vagias, C.; Roussis, V. Natural products with anti-HIV activity from marine organisms. Curr. Top. Med. Chem. 2003, 3, 1512-1535.
19. Pous, C.; Chabin, K.; Drechou, A.; Barbot, L.; Phung-Koskas, T.; Settegrana, C.; Bourguet-Kondracki, M.L.; Maurice, M.; Cassio, D.; Guyot, M.; Durand, G. Functional specialization of stable and dynamic microtubules in protein traffic in WIF-B cells. J. Cell. Biol. 1998, 142, 153-165.
20. Cruciani, V.; Mikalsen, S.O. Ilimaquinone inhibits gap junctional communication in a connexin isotype-specific manner. Exp. Cell Res. 2005, 304, 136-148.
21. Nambiar, M. P.; Wu, H.C. Ilimaquinone inhibits the cytotoxicities of ricin, diphtheria toxin, and other protein toxins in Vero cells. Exp. Cell Res. 1995, 219, 671-678.
22. Aoki, S.; Kong, D.; Matsui, K.; Rachmat, R.; Kobayashi, M. Sesquiterpene aminoquinones, from a marine sponge, induce erythroid differentiation in human chronic myelogenous leukemia, K562 cells. Chem. Pharm. Bull. 2004, 52, 935-937.