New acetylenic compounds from the sponge reniera fulva

✍ Scribed by G. Cimino; S. De Stefano

• Book ID: 104244123
• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 242 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93008-4

✦ Synopsis

Very few acetylenic compounds from marine organisms have been reported so far. Algae have proved to be a good source of halogenated products' among which a small group of ethers, characterized by a straight-chain C-15 carbon skeleton and a terminal enyne functionl,has been isolated. In the case of sponges, acetylenic functions have been found only in some arylcarotenoids isolated from Reniera japonica3.

In the course of our research for new metabolites from marine sponges4, Reniera fulva was -found to contain a new group of substances characterized by unsaturated and in some cases, brominated, long alkyl chains containing, also, acetylenic bonds.

Fresh tissues of the sponge, collected in the bay of Naples, were exhaustively extracted with acetone. Ether-water partition of the residue and silica gel column chromatography (lightpetroleum and increasing amounts of ether) of the ether-soluble fraction (5,9 g from 100 g of the dry weighted animal), followed by preparative SiO, t.l.c., gave five closely related new acetylenic compounds named, in order of polarity, debrorenierin-1 (1; 0,04X based on the dry weight of the animal), renierin-1 (2; 0,4%), lb-dihydrorenierin-1 (2; 0,06%), renierin-2 (4; 0,15%), 18-hydroxyrenierin-2 (5; 0.06%). Three of these new substances were oils, the other two crystalline. All compounds were homogeneous on Si02 t.1.c. and g.1.c. (Se 30; 3%). Scarceness of material and the instability of most of them did not allow extensive chemical investigation and the structures were mainly assigned on the basis of spectral data. The molecular formulas were derived from accurate mass measurements.