Lissoclibadins 8-14, polysulfur dopamine-derived alkaloids from the colonial ascidian Lissoclinum cf. badium

Tetrahedron

Volumn 65, Issue 46, 2009, Pages 9598-9603

  Wang, Weifang ^a   Takahashi, Ohgi ^a   Oda, Taiko ^b   Nakazawa, Takahiro ^a   Ukai, Kazuyo ^a   Mangindaan, Remy E P ^c   Rotinsulu, Henki ^c   Wewengkang, Defny S ^a,c   Kobayashi, Hisayoshi ^d   Tsukamoto, Sachiko ^e   Namikoshi, Michio ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^b KEIO UNIVERSITY   (Japan)

^c SAM RATULANGI UNIVERSITY   (Indonesia)

^d UNIVERSITY OF TOKYO   (Japan)

^e KUMAMOTO UNIVERSITY   (Japan)

Author keywords

Cytotoxicity; L1210; Polysulfur alkaloid; Structure assignment; Tunicate; V79

Indexed keywords

ALKALOID DERIVATIVE; DIMER; DISULFIDE; DOPAMINE DERIVATIVE; LISSOCLIBADIN 10; LISSOCLIBADIN 11; LISSOCLIBADIN 12; LISSOCLIBADIN 13; LISSOCLIBADIN 14; LISSOCLIBADIN 8; LISSOCLIBADIN 9; SULFIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ASCIDIACEA; CELL PROLIFERATION; CHEMICAL STRUCTURE; COLONY FORMATION; CONTROLLED STUDY; CYTOTOXICITY; DISULFIDE BOND; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; SPECTROSCOPY;

ASCIDIA; CRICETULUS GRISEUS; LISSOCLINUM; MURINAE;

EID: 70349792234     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.056     Document Type: Article

References (20)

1. Blunt J.W., Copp B.R., Hu W.-P., Munro M.H.G., Northcote P.T., and Prinsp M.R. Nat. Prod. Rep. 26 (2009) 170-244 (and previous reports in this series)
2. Wang W.-F., and Namikoshi M. Heterocycles 74 (2007) 53-88
3. Part of this work was presented in the 49th Symposium on The Chemistry of Natural Products (Sapporo, Japan, 2007), Symposium Papers, pp 359-364. The structure of lissoclibadin 8 in the above abstract was wrong and should be corrected to 1 as shown in Figure 1 in this paper. NMR data for lissoclibadins 11 and 12 in the above abstract (p 362, Table 4) were listed in the opposite place.
4. Liu H., Pratasik S.B., Nishikawa T., Shida T., Tachibana K., Fujiwara T., Nagai H., Kobayashi H., and Namikoshi M. Tetrahedron Lett. 45 (2004) 7015-7017
5. Liu H., Fujiwara T., Nishikawa T., Mishima Y., Nagai H., Shida T., Tachibana K., Kobayashi H., Mangindaan R.E.P., and Namikoshi M. Tetrahedron 61 (2005) 8611-8615
6. Nakazawa T., Xu J., Nishikawa T., Oda T., Fujita A., Ukai K., Mangindaan R.E.P., Rotinsulu H., Kobayashi H., and Namikoshi M. J. Nat. Prod. 70 (2007) 439-442
7. Compagnone R.S., Faulkner D.J., Carté B.K., Chan G., Freyer A., Hemling M.E., Hofmann G.A., and Mattern M.R. Tetrahedron 50 (1994) 12785-12792
8. Davidson B.S., Molinski T.F., Barrows L.R., and Ireland C.M. J. Am. Chem. Soc. 113 (1991) 4709-4710
9. Searle P.A., and Molinski T.F. J. Org. Chem. 59 (1994) 6600-6605
10. Litaudon M., Trigalo F., Martin M.-T., Frappier F., and Guyot M. Tetrahedron 50 (1994) 5323-5334
11. Patil A.D., Freyer A.J., Killmer L., Zuber G., Carté B., Jurewicz A.J., and Johnson R.K. Nat. Prod. Lett. 10 (1997) 225-229
12. Appleton D.R., Pearce A.N., Lambert G., Babcock R.C., and Copp B.R. Tetrahedron 58 (2002) 9779-9783
13. Makarieva T.N., Stonik V.A., Dmitrenok A.S., Grebnev B.B., Iskov V.V., and Rebachyk N.M. J. Nat. Prod. 58 (1995) 254-258
14. Davis R.A., Sandoval I.T., Concepcion G.P., da Rocha R.M., and Ireland C.M. Tetrahedron 59 (2003) 2855-2859
15. Spartan'04, Wavefunction, Irvine, CA.
16. Lissoclibadin 14 (7) has been presented the structure in the 49th Symposium on The Chemistry of Natural Products (Sapporo, Japan) in 2007 (Ref. 3) and applied a Patent (Application 2007-198404: P2009-35485A). The same structure was reported from L. cf. badium collected in Papua New Guinea:. Clement J.A., Kitagaki J., Yang Y., Saucedo C.J., O'Keefe B.R., Weissman A.M., McKee T.C., and McMahon J.B. Bioorg. Med. Chem. 16 (2008) 10022-10028
17. Oda T., Kamoshita K., Maruyama S., Masuda K., Nishimoto M., Xu J., Ukai K., Mangindaan R.E.P., and Namikoshi M. Biol. Pharm. Bull. 30 (2007) 385-387
18. This bioassay was done by the Research Development Group, Nippon Kayaku Ltd.
19. Sakakibara Y., Saito I., Ichinoseki K., Oda T., Kaneko M., Saito H., Kodama M., and Sato Y. Mutat. Res. 263 (1991) 269-276
20. Sato Y., Sakakibara Y., Oda T., Aizu-Yokota E., and Ichinoseki I. Chem. Pharm. Bull. 40 (1992) 182-184