Fatty acids in sponges

Garson MJ, Zimmermann MP, Battershill CN, Holden JL, Murphy PT (1994) The Distribution of Brominated Long-Chain Fatty Acids in Sponge and Symbiont Cell Types from the Tropical Marine Sponge Amphimedon terpenensis. Lipids 29 509... 

Figure 19.13 Probable biosynthesis of 6-bromo-A-5,9 long-chain fatty acids in sponges. ...

Barnathan, G. and Kornprobst, J.M. (1998) Isoprenoid fatty acids in sponge phospholipids. A review. Recent Res. Dev. Lipids Res., 2, 235-248. 

Litchfield, C., Greenberg, A.J., Noto, G., and Morales, R.W. (1976b) Unusually high levels of C24-C30 fatty acids in sponges of the class Demospongiae. Lipids, 11, 567-570. 

Several monounsaturated phospholipid fatty acids exist in nature, but few cases are known of very long-chain monounsaturated acids longer than 22 carbons. However, marine sponges are unusual in that they have very long-chain fatty acids in their phospholipids. Sponges have provided the most interesting examples of long-chain phospholipid fatty acids since... 

Carballeira NM, Emiliano A (1993) Novel Brominated Phospholipid Fatty Acids in the Caribbean Sponge Agelas sp. Lipids 28 763... 

Imbs, A.B., and N. A. Latyshev, New A4 and A5 Unsaturated Medium- and Long-Chain Fatty Acids in the Freshwater Sponge Baicalospogia bacilifera, Chem. Phys. Lipids, 92 117-125 (1998). 

Imbs, A.B. and Latyshev, N.A. (1998) New A5 and A4 rmsaturated medimn- and longfatty acids in the freshwater sponge Baicalospon bacilifera. Chem. Phys. Lipids, 92, 117-125. 

Blumenberg, M. and Michaelis, W. (2007) High occurrence of brominated lipid fatty acids in boreal sponges of the order Halichondrida. Mar. Biol., 150,1153-1169. 

Carballeira, N.M., Cruz, H., Kwong, C.D., Wan, B., and Franzblau, S. (2004) 2-Methoxylated fatty acids in marine sponges defense mechanism against mycobacteria Lipids, 39, 675-680. 

Dembitsky, V.M. and Rezanka, T. (1996) Unusually high levels of eicosatetraenoic, eicosapentaenoic, and docosahexaenoic fatty acids in Palestinian freshwater sponges. Lipids, 31, 647-650. 

Barnathan, G., Kornprobst, J.M., Doumenq, P., Miralles, J., and Boury-Esnault, N. (1993b) Sponge fatty acids 5. Characterization of complete series of 2-hydroxy long-chain fatty acids in phospholipids of two Senegalese marine sponges from the family Suberitidae Pseudosuberites sp. and Suberites massa.J. Nat. Prod., 56, 2104-2113. 

It has been suggested [6] that these unusual sterols, especially in those cases where these unusual sterols comprise the entire sterol content of the organisms, likely replace conventional sterols as cell-membrane components. Evidence for this comes from subcellular fractionation and subsequent analysis of two marine sponges [10]. The sterol composition of the membrane isolates was found to be identical to that of the intact sponge. Most common variation of the marine sterol is in the side-chain, situated deep in the lipophylic environment of the phospholipid bilayer. This suggests that unusual fatty acids might accompany the sterols, and indeed this is often the case [8]. 

Brominated fatty acids are rare in nature. They have been found in sponges and other marine animals. Recently, the presence of (5E, 7E)-18-bromo-octadeca-5,17-diene-15-ynoic acid (221) and 18-bromo-octadeca-5,7,17-triynoic acid (222) has been described in a halophilic (present in hypersaline environments) terrestrial organism, the Central Asian lichen Acorospora gobiensis [171]. 

The theonezolides A-C (431-433) were isolated from the sponge Theonella sp. They are 37-membered macrocyclic compounds consisting of two principal fatty acid chains with various functionalities such as a sulfate ester, an oxazole, and a thiazole [336, 337]. Compounds 431-433 displayed cytotoxic activity against L1210 and KB cells and were found to have a unique bioactivity in terms of induction of rabbit platelet shape change and aggregation [338]. 

From the sponge M. incrustans, two cerebrosides and a polar glycolipid were isolated.78 Both cerebrosides contain galactose and sphingosine, but differ in the nature of their fatty acids the less polar cerebroside contains normal, and the more polar, monohydroxy, acids. The structure of the polar glycolipid was not established, but it was shown to contain sphingosine, fatty acids, galactose, arabinose, fucose, and phosphorus.78... 

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