Isolation of C11 cyclopentenones from two didemnid species, Lissoclinum sp. and Diplosoma sp.

Marine Drugs

Volumn 7, Issue 4, 2009, Pages 816-832

  Ogi, Takayuki ^a,b   Margiastuti, Palupi ^a   Teruya, Toshiaki ^a   Taira, Junsei ^c   Suenaga, Kiyotake ^d   Ueda, Katsuhiro ^a  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

^b Okinawa Industrial Technology Center   (Japan)

^c OKINAWA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^d KEIO UNIVERSITY   (Japan)

Author keywords

Cyclopentenone; Cytotoxicity; Didemnenone; Diplosoma; Lissoclinum

Indexed keywords

CYCLOPENTENONE DERIVATIVE; DIDEMNENONE 1; DIDEMNENONE 2; DIDEMNENONE 5; UNCLASSIFIED DRUG; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ASCIDIACEA; CANCER CELL CULTURE; CONTROLLED STUDY; DIPLOSOMA; DRUG ISOLATION; DRUG STRUCTURE; LISSOCLINUM; NONHUMAN; SPECTROSCOPY; ANIMAL; CHEMISTRY; DRUG SCREENING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; UROCHORDATA;

ASCIDIA; DIDEMNIDAE; DIPLOSOMA (TUNICATE); LISSOCLINUM;

ANIMALS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOPENTANES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE-ACTIVITY RELATIONSHIP; UROCHORDATA;

EID: 75149198747     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md7040816     Document Type: Article

References (39)

1. Davidson, B.S. Ascidians: Producer of amino acid-derived metabolites. Chem. Rev. 1993, 93, 1771-1791.
2. Faukner, D.J. Marine natural products. Nat. Prod. Rep. 2002, 19, 1-48, and previous reports in this series.
3. Blunt, J.W.; Copp, B.R.; Hu, W-P.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R.J. Marine natural products. Nat. Prod. Rep. 2008, 25, 35-94, and previous reports in this series.
4. Rinehart, K.L. Antitumor compounds from tunicates. Med. Res. Rev. 2000, 20, 1-27.
5. Lewin, R.A. Prochlorophyta as a proposed new division of algae. Nature 1976, 261, 697-698.
6. Withers, N.; Vidaver, W.; Lewin, R.A. Pigment composition, photosynthesis and fine structure of a non-blue-green prokaryotic algal symbiont (Prochloron sp.) in a didemnid ascidian from Hawaiian waters. Phycologia 1978, 17, 167-171.
7. Oka, T.A.; Hirose, E. Some didemnid ascidians harboring prokaryotic algae from the reef shores in the Yaeyama islands, Okinawa, Japan. Biol. Mag. Okinawa 2005, 43, 45-52.
8. Zabriskie, T.M.; Mayne, C.L.; Ireland, C.M. Patellazole C: A novel cytotoxic macrolide from Lissoclinum patella. J. Am. Chem. Soc. 1988, 110, 7919-7920.
9. Coreley, D.G.; Moore, R.E.; Paul, V.J. Patellazole B: A novel cytotoxic thiazole-containing macrolide from the marine tunicate Lissoclinum patella. J. Am. Chem. Soc. 1988, 110, 7920-7922.
10. Davidson, B.S.; Molinski, T.F.; Barrows, L.R.; Ireland, C.M. Varacin: A novel benzopentathiepin from Lissoclinum vareau that is cytotoxic toward a human colon tumor. J. Am. Chem. Soc. 1991, 113, 4709-4710.
11. Carroll, A.R.; Feng, Y.; Bowden, B.F.; Coll, J.C. Studies of Australian ascidians. 5. Virenamides A-C, new cytotoxic linear peptides from the colonial didemnid ascidian Diplosoma virens. J. Org. Chem. 1996, 12, 4059-4061.
12. Ueda, K.; Hu, Y. Haterumalide B: A new cytotoxic macrolide from an Okinawan ascidian Lissoclinum sp. Tetrahedron Lett. 1999, 40, 6305-6308.
13. Uddin, M.J.; Kokubo, S.; Suenaga, K.; Ueda, K.; Uemura, D. Haterumaimides A-E, five new dichlorolissoclimide-type diterpenoids from an ascidian, Lissoclinum sp. Heterocycles 2001, 54, 1039-1047.
14. Uddin, M.J.; Kokubo, S.; Ueda, K.; Suenaga, K.; Uemura, D. Haterumaimides F-I, four new cytotoxic diterpene alkaloids from an ascidian Lissoclinum species. J. Nat. Prod. 2001, 64, 1169-1173.
15. Uddin, M.J.; Kokubo, S.; Ueda, K.; Suenaga, K.; Uemura, D. Haterumaimides J and K, potent cytotoxic diterpene alkaloids from the ascidian Lissoclinum species. Chem. Lett. 2002, 10, 1028-1029.
16. Lindquist, N.; Fenical, W.; Sesin, D.F.; Ireland, C.M.; Duyne, G.D.V.; Forsyth, C.J.; Clardy, J. Isolation and structure determination of the didemnenones, novel cytotoxic metabolites from tunicates. J. Am. Chem. Soc. 1988, 110, 1308-1309.
17. Beil, W.; Gores, M.; Nerenz, F.; Winterfeldt, E. Total synthesis of tumor inhibiting didemnenone analogues. J. Prakt. Chem, 1999, 341, 384-390.
18. Forsyth, C.J.; Clardy, J. Total synthesis of (+)-didemnenones A and B. Absolute configurations of the didemnenones. J. Am. Chem. Soc. 1988, 110, 5911-5912.
19. Ogi, T.; Taira, J.; Margiastuti, P.; Ueda, K. Cytotoxic metabolites from the Okinawan ascidian Diplosoma virens. Molecules 2008, 13, 595-602.
20. Wratten, S.J.; Faulkner, D.J. Antimicrobial metabolites from the marine sponge Ulosa sp. Tetrahedron Lett. 1978, 19, 961-964.
21. Guzii, G.A.; Makar'eva, N.T.; Denisenko, A.V.; Dmitrenok, S.P.; Dmitrenok, S.A.; Grebnev, B.B.; Stonik, A.V. Diosphenol from the ascidian Diplosoma sp. Chem. Nat. Comp. 2008, 4, 372-373.
22. Maarisit, W.; Rob, T.; Ogi, T.; Taira, J.; Ueda, K. Bioactive metabolites from Okinawan marine organisms. In Proceedings of the World Ocean Conference, Manado Northsulawesi, Indonesia, May 11-15, 2009, in press.
23. Margiastuti, P.; Ogi, T.; Teruya, T.; Taira, J.; Suenaga, K.; Ueda, K. An unusual iodinated 5′-deoxyxylofuranosyl nucleoside from an Okinawan ascidian, Diplosoma sp. Chem. Lett. 2008, 37, 448-449.
24. Isono, K. Nucleoside antibiotics: Structure, biological activity, and biosynthesis. J. Antibiot. 1988, 41, 1711-1739.
25. Isono, K. Current progress on nucleoside antibiotics. Pharmacol. Ther. 1991, 52, 269-286.
26. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K. Bioactive marine metabolites IX. Mycalisines A and B, novel nucleosides which inhibit cell division of fertilized starfish eggs, from the marine sponge Image sp. Tetrahedron Lett. 1985, 26, 3483-3486.
27. Fuhrman, F.A.; Fuhrman, G.J.; Kim, Y.H.; Pavelka, L.A.; Mosher, H.S. Doridosine: A new hypotensive N-methylpurine riboside from the nudibranch Anisodoris nobilis. Science 1980, 207, 193-195.
28. Demattè, N.; Guerriero, A.; Lafargue, F.; Pietra, F. 2′-Deoxynucleoside uronic acids from the ascidian Aplidium (=Amaroucium) fuscum (Drasche, 1883). Comp. Biochem. Physiol. B: Biochem. Mol. Biol. 1986, 84, 11-13.
29. Francesconi, K.A.; Stick, R.V.; Edmonds, J.S. An arsenic-containing nucleoside from the kidney of the giant clam, Tridacna maxima. J. Chem. Soc. Chem. Commun. 1991, 928-929.
30. Kondo, K.; Shigemori, H.; Ishibashi, M.; Kobayashi, J. Aplysidine, a new nucleoside from the Okinawan marine sponge Aplysina sp. Tetrahedron 1992, 47, 7145-7148.
31. Francesconi, K.A.; Edmonds, J.S.; Stick, R.V. Arsenic compounds from the kidney of the giant clam Tridacna maxima: Isolation and identification of an arsenic-containing nucleoside. J. Chem. Soc. Perkin Trans. 1 1992, 1349-1357.
32. Searle, P.A.; Molinski, T.F. Trachycladines A and B: 2′-C- Methyl-5′-deoxyribofuranosyl nucleosides from the marine sponge Trachycladus laevispirulifer. J. Org. Chem. 1995, 60, 4296-4298.
33. Kazlauskas, R.; Murphy, P.T.; Wells, R.J.; Baird-Lambert, J.A.; Jamieson, D.D. Halogenated pyrrolo[2,3-d]pyrimidine nucleosides from marine organisms. Aust. J. Chem. 1983, 36, 165-170.
34. Cimino, G.; Crispino, A.; de Stefano, S.; Gavagnin, M.; Sodano, G. A naturally-occurring analog of methylthioadenosine (MTA) from the nudibranch molluse Doris verrucosa. Experientia 1986, 42, 1301-1302.
35. 11 metabolites from an Okinawan cyanobacterial (Synechocystis sp.) overgrowth of coral. Tetrahedron Lett. 1995, 36, 849-852.
36. Teruya, T.; Nakagawa, S.; Koyama, T.; Suenaga, K.; Uemura, D. Terpiodiene: A novel tricyclic alcohol from the Okinawan sponge Terpios hoshinota. Chem. Lett. 2002, 31, 38-39.
37. Mann, J. Secondary metabolites derived from acetate fatty acid and polyketides. In Secondary Metabolism; Atkins, P.W., Holker, J.S.E., Holiday, A.K., Eds.; Oxford University Press: Walton Street, Oxford, UK, 1990; pp. 55-58.
38. Moravcová, J.; Capková, J.; Stanek, J. One-pot synthesis of 1,2-O-isopropylidene-α-D-xylofuranose. Carbohydr. Res. 1994, 263, 61-66.
39. 13C]-enriched 5-deoxypentoses and 5-O-methylpentoses. Carbohydr. Res. 1987, 163, 169-188.