New bromotyrosine metabolites from the sponge Aplysinella rhax

Citation
J. Shin et al., New bromotyrosine metabolites from the sponge Aplysinella rhax, TETRAHEDRON, 56(46), 2000, pp. 9071-9077
Citations number
11
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
0040-4020 → ACNP
Volume
56
Issue
46
Year of publication
2000
Pages
9071 - 9077
Database
ISI
SICI code
0040-4020(20001110)56:46<9071:NBMFTS>2.0.ZU;2-2
Abstract
Four new bromotyrosine metabolites (3-6) along with the previously describe d compounds psammaplin A (1) and bisaprasin (2) have been isolated from the sponge Aplysinella rhax collected from Guam, Palau, and Pohnpei. Based upo n the results of extensive spectroscopic analysis and chemical reaction, th e structures of psammaplins A(1) (3) and A(2) (4) have been determined to b e a N,N-dimethylguanidium salt of psammaplin A sulfate and its bis-N,N-dime thylguanidium disulfate derivative, respectively. Aplysinellin A (5) posses ses an additional bromotyrosine-derived C-9 unit connected directly to the carbon framework of psammaplin A by a biphenylic Linkage while aplysinellin B (6) is the corresponding cyclic enol ether. These compounds exhibited mo derate cytotoxicity and inhibitory activities against farnesyl protein tran sferase and leucine aminopeptidase. (C) 2000 Elsevier Science Ltd. All righ ts reserved.