Isolation of C11 Cyclopentenones from Two Didemnid Species, Lissoclinum sp. and Diplosoma sp.

A series of new C11 cyclopentenones 1–7 was isolated, together with four known metabolites 9/10, 12 and 13, from the extract of the didemnid ascidian Lissoclinum sp. The other didemnid ascidian Diplosoma sp. contained didemnenones 1, 2 and 5, and five known metabolites 8–12. The structures of 1–7 were elucidated by spectroscopic analyses. Cytotoxicity of the isolated compounds was evaluated against three human cancer cell lines (HCT116, A431 and A549).

[1]  J. Taira,et al.  Bioactive Metabolites from Okinawan Marine Organisms , 2009 .

[2]  V. Stonik,et al.  Diosphenol from the ascidian Diplosoma sp. , 2008, Chemistry of Natural Compounds.

[3]  K. Suenaga,et al.  An Unusual Iodinated 5'-Deoxyxylofuranosyl Nucleoside from an Okinawan Ascidian, Diplosoma sp , 2008 .

[4]  J. Taira,et al.  Cytotoxic Metabolites from the Okinawan Ascidian Diplosoma virens , 2008, Molecules.

[5]  M. Gavagnin,et al.  A naturally-occurring analog of methylthioadenosine (MTA) from the nudibranch molluscDoris verrucosa , 1986, Experientia.

[6]  K. Suenaga,et al.  Haterumaimides J and K, potent cytotoxic diterpene alkaloids from the ascidian Lissoclinum species , 2002 .

[7]  K. Suenaga,et al.  Terpiodiene: A Novel Tricyclic Alcohol from the Okinawan Sponge Terpios hoshinota , 2002 .

[8]  D. Faulkner,et al.  Marine natural products. , 2000, Natural product reports.

[9]  K. Suenaga,et al.  Haterumaimides F-I, four new cytotoxic diterpene alkaloids from an ascidian Lissoclinum species. , 2001, Journal of natural products.

[10]  K. Suenaga,et al.  Haterumaimides A—E, Five New Dichlorolissoclimide-Type Diterpenoids from an Ascidian, Lissoclinum sp. , 2001 .

[11]  K. Rinehart Antitumor compounds from tunicates , 2000, Medicinal research reviews.

[12]  D. Faulkner Marine natural products. , 2000, Natural product reports.

[13]  K. Ueda,et al.  Haterumalide B: A new cytotoxic macrolide from an Okinawan ascidian Lissoclinum sp. , 1999 .

[14]  W. Beil,et al.  Total synthesis of tumor inhibiting didemnenone analogues , 1999 .

[15]  A. Carroll,et al.  Studies of Australian Ascidians. Part 5. Virenamides A‐C, New Cytotoxic Linear Peptides from the Colonial Didemnid Ascidian Diplosoma virens. , 1996 .

[16]  A. Carroll,et al.  Studies of Australian Ascidians. 5. Virenamides A-C, New Cytotoxic Linear Peptides from the Colonial Didemnid Ascidian Diplosoma virens. , 1996, The Journal of organic chemistry.

[17]  T. Molinski,et al.  Trachycladines A and B: 2′‐C‐Methyl‐5′‐deoxyribofuranosyl Nucleosides from the Marine Sponge Trachycladus laevispirulifer , 1995 .

[18]  W. Gerwick,et al.  Nakienones A-C and nakitriol, new cytotoxic cyclic C11 metabolites from an okinawan cyanobacterial (Synechocystis sp.) overgrowth of coral , 1995 .

[19]  J. Stanek,et al.  One-pot synthesis of 1,2-O-isopropylidene-a-d-xylofuranose , 1994 .

[20]  B. S. Davidson Ascidians: Producers of Amino Acid Derived Metabolites , 1993 .

[21]  M. Ishibashi,et al.  Aplysidine, a new nucleoside from the Okinawan marine sponge Aplysina Sp. , 1992 .

[22]  J. Edmonds,et al.  Arsenic compounds from the kidney of the giant clam Tridacna maxima : isolation and identification of an arsenic-containing nucleoside , 1992 .

[23]  K. Isono Current progress on nucleoside antibiotics. , 1991, Pharmacology & therapeutics.

[24]  C. Ireland,et al.  Varacin (I): A Novel Benzopentathiepin from Lissoclinum vareau That Is Cytotoxic Toward a Human Colon Tumor. , 1991 .

[25]  J. Edmonds,et al.  An arsenic-containing nucleoside from the kidney of the giant clam, Tridacna maxima , 1991 .

[26]  K. Isono,et al.  Nucleoside antibiotics: structure, biological activity, and biosynthesis. , 1988, The Journal of antibiotics.

[27]  Richard E. Moore,et al.  Patellazole B: a novel cytotoxic thiazole-containing macrolide from the marine tunicate Lissoclinum patella , 1988 .

[28]  C. Ireland,et al.  Patellazole C: A Novel Cytotoxic Macrolide from Lissoclinum patella , 1988 .

[29]  J. Clardy,et al.  Total synthesis of (+)-didemnenones A and B: absolute configurations of the didemnenones , 1988 .

[30]  J. Clardy,et al.  Isolation and structure determination of the didemnenones, novel cytotoxic metabolites from tunicates , 1988 .

[31]  J. R. Snyder,et al.  Synthesis and n.m.r.-spectral analysis of unenriched and [1-13C]-enriched 5-deoxypentoses and 5-O-methylpentoses. , 1987, Carbohydrate research.

[32]  F. Pietra,et al.  2′-deoxynucleoside uronic acids from the ascidian Aplidium (= Amaroucium) fuscum (Drasche, 1883) , 1986 .

[33]  S. Matsunaga,et al.  Bioactive marine metabolites IX. Mycalisines A and B, novel nucleosides which inhibit cell division of fertilized starfish eggs, from the marine sponge mycale sp. , 1985 .

[34]  P. T. Murphy,et al.  Halogenated Pyrrolo(2,3-dlpyrimidine Nucleosides from Marine Organisms , 1983 .

[35]  H. Mosher,et al.  Doridosine: a new hypotensive N-methylpurine riboside from the nudibranch Anisodoris nobilis. , 1980, Science.

[36]  R. Lewin,et al.  Pigment composition, photosynthesis and fine structure of a non-blue-green prokaryotic algal symbiont (Prochloron sp.) in a didemnid ascidian from Hawaiian waters , 1978 .

[37]  D. Faulkner,et al.  Antimicrobial metabolites from the marine sponge ulosa sp. , 1978 .

[38]  R. Lewin Prochlorophyta as a proposed new division of algae , 1976, Nature.