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A diketopiperazine derived from trichloroleucine from the sponge Dysidea herbacea

✍ Scribed by R. Kazlauskas; P.T. Murphy; R.J. Wells

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 163 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85777-4

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✦ Synopsis

Dysidea herbacea is a Dictyoceratid sponge which is common throughout the Indo-Pacific region. Previous studiesls3 have shown that the secondary metabolites derived from various collections of this sponge are diverse, ranging from polybromodiphenyl ethers, of which (1) is an example', to compounds derived from amino-acids and containing trichloromethyl-groups. Two examples dysidin (2) and dysidenin (3) have recently been reported 2,3 . We now report a further variant of this sponge, collected near Gladstone, Queensland, Australia, which has yielded a diketopiperazine derivative (4) of an N-methyltrichloroleucine. Extraction of a small freeze dried sample of D. herbacea with CH2C12 followed by p.1.c. separation of the extract on silica gel (CH2C12/EtOAc: 4/l) yielded (4) m.p. 106-107", Cal:' -144' (c=O.5, CHC13) in 1% yield. The formula C14H18C16N202 was established by high resolution mass spectrometry and the presence of two trichloro-methyl groups in the molecule was indicated by the 13C n.m.r. spectrum which showed two singlets at 105.0 and 104.1 typical of this 2,3 grouping

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