Dysidea etheria

The indole 22 was previously isolated from the sponge Dysidea etheria [110] and has now been obtained from the Antarctic ice bacterium ARK 13-2-437. The lipid phase of Hel45 delivered additionally N-(2-hydroxyethyl)-ll-octadecen-amide and the new natural products 17-methyl-16-octadecenoic acid [95] and indole-3-carboxylic acid thiomethyl ester (23). 

Gunasekera, S.P. McCarthy, P.J. Kelly-Borges, M. Lobkovsky, E. Clardy, J. (1996A) Dysidiolide a novel protein phosphatase inhibitor from the Caribbean sponge Dysidea etheria. J. Am. Chem. Soc., 118, 8759-60. 

Dysidiolide(cdc25) (Structure 16.7) lima Sponge, Dysidea etheria Anticancer18... 

C25H38O4, Mr 402.57, cryst., mp. 186-187°C, [0] -11.1 (CH2CI2/CHjOH, 1 1). Protein tyrosine phosphatase cdc 25 A-inhibitor (antimitotic activity by arresting the cell cycle, the cells become unable to divide) from the Caribbean sponge Dysidea etheria. D. is a sesterterpenoid, it is being tested in various cancer models, e.g., lung carcinoma and leukemia. 

The parent hydrocarbon skeletons of bieyelie sesterterpenes are derived predominantly from some sesquiterpenes. Diprenyldrimanes, for example, realized as (- -)-dysideapalaunic acid and related laetones, partly reported to be natural inhibitors of protein phosphatase, are isolated from the Caribbean sponge Dysidea etheria and other Dysidea species. Prenyldrimanes in higher plants are represented by (-)-salvisyriacolide from Salvia syriaca and as (-l-)-salvileucolide methylester from Salvia hypoleuca (Labiatae). 

The first of these examples was reported (Scheme 136) by the group of E. J. Corey (566). In 1997, this group published the total synthesis of the neo-isolabdanoid sesterterpene dysidiolide (655) from the Caribbean spraige Dysidea etheria (568). Dysidiolide was found to be the first naturally derived inhibitor of... 

Gunasekera SP, McCarthy PJ, Kelly-Borges M, Lobkovsky E, Clardy J (1996) Dysidiolide A Novel Protein Phosphatase Inhibitor from the Caribbean Sponge Dysidea etheria de Laubenfels. J Am Chem Soc 118 8759... 

Grode, S.H., and J.H. Cardellina II Sesquiterpenes from the Sponge Dysidea etheria and the Nudibranch Hypselodoris zebra. J. Nat. Prod. 47, 76 (1984). 

Cardellina, J.H. II and Bamekow, D.E. (1988) Oxidized nakafuran 8, sesquiterpenes from the sponge Dysidea etheria. Structure, stereochemistry and biological activity. J. Org. Chem., 53, 882-884. 

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