A New Furanosesterpene From the Marine Sponge Psammocinia rugosa

Abstract

A tetronic acid (5), 5-[13-(furan-3-yl)-2,6,10-trimethyltrideca-2,6,8-trienyl]-4-hydroxy 3-methylfuran-2(5H)-one,* with weak antimicrobial activity has been isolated from the sponge Psammocinia sp. and characterized by analysis of 1H and 13C n.m.r. data including 'H-1H correlation (COSY) experiments. The compound may be identical to a tetronic acid isolated by the Roche group, previously assigned structure (3).

New Cytotoxic Sesterterpenes from the Sponge Sarcotragus Species

“…The E geometry of the trisubstituted double bond (C-8) was assigned on the basis of the upfield resonance (δ C 16.5, C-9) of the vinylic methyl carbon, while the geometry of the disubstituted double bond (C-11) was determined to be E on the basis of the coupling constants of the respective protons ( J = 15.1 Hz). The carbon chemical shift of the C-19 methyl (δ C 24.4) indicated the Z geometry of this trisubstituted double bond, which was also supported by an upfield shift of the C-20 signal (δ C 35.4) compared to that of palinurin (δ C 41.6, C-20). − The low-resolution FABMS spectrum of 1 showed an [M + Na] + ion at m / z 421 and a characteristic [M + 2Na − H] + ion at m / z 443, which might be produced by an exchange of the acidic hydrogen with Na + followed by complexation with a second Na + . The molecular ion was detected at m / z 398 in EIMS.…”

“…Diverse biological activities such as antibacterial, ,− ,− antiviral, antitumor, ,− antiinflammatory, antispasmodic, brine shrimp lethality, ,, ichthyotoxicity, , and inhibitory activities to starfish egg, ,, sea urchin sperm, and protein phosphatase have been attributed to furanosesterterpene tetronic acids. The tetronic acid functionality was suggested to be essential for antibiotic activity, and the unconjugated tetronic acid furanosesterterpenes were more active than the conjugated counterparts .…”

Cyclocinamide A. An Unusual Cytotoxic Halogenated Hexapeptide from the Marine Sponge Psammocinia

“…(Thorectidae) proved to be potent and partially selective in their cytotoxicity profiles. The scant previous literature on the genus Psammocinia describes only acyclic sesterterpenes containing both terminal tetronic acid and furan moieties . Knowing that such compounds, including variabilin, were present in the extracts, but were not responsible for the activity results, prompted a bioassay-guided isolation of the active constituents.…”

Heterocyclic terpenes: linear furano- and pyrroloterpenoids

“…Compound 223 has been reported as a constituent of Psarnrnocinia rugosa. 158 The bisfurans spongionellin 224 and dehydrospongionellin have been described in extracts of a Spongionella species. 159 The okinonellins A 225 and B 226 are furanosesterterpenes from another Spongionella species, which inhibit celldivision in fertilized starfish eggs and again may play a role in marine chemical ecology.…”