Lithistid sponges

Macrolides from lithistid sponges and long-chain guanidine alkaloids (phloeodictyins) from nepheliospongid sponges are the most unusual metabolites from New Caledonian deep waters (Table 9.III). 

Sampling in Mediterranean deep waters has revealed the first secondary n tabolites from brachiopods and unique 10-hydroxyeicosa- and docosapolyenoic acids from scleractinian corals. That these fetty acids have also been foimd in a deep-water pre-Antarctic antipatharian coral (Table 9.III) must be attributed to convergence. Deep-water Mediterranean medusae and a lithistid sponge from New Caledonia, Corallistes sp., contain huge amounts of free porphyrins. 

GuCTTiwo, A. D Ambrosio, M. Pietra, F. Debitus, C. Ribes, O. (1993) Pteridines, sterols, and indole (ta ivatives from the lithistid sponge Corallistes undulatus of the Coral Sea. J. Nat. Prod., 56, 1962-70. 

Qureshi, A. Colin, P.L. Faulkner, D.J. (2000) Microsclerodermins F-I, antitumor and antifungal cyclic peptides from the lithistid sponge Microscleroderma sp. Tetrahedron, 56, 3679-85. 

Bewley CA, Faulkner DJ (1998) Lithistid Sponges Star Performers or Hosts to the Stars. Angew Chem Int Ed 37 2162... 

Bewley CA, Faulkner DJ (1995) Theonegramide, an Antifungal Glycopeptide from the Philippine Lithistid Sponge Theonella swinhoei. J Org Chem 60 2644... 

Over half of the compounds reported for lithistid sponges were isolated from Theonella (family Theonellidae). Theonella species have been reported to contain a wide variety of cyclic and linear peptides and polyketides, as well as 3-alkyl piperidine derivatives nearly identical to those reported from the order Haplosclerida.58 There is also a single report of cyano- and isothiocyano-sesquiter-penes similar to those isolated from Axinellidae (order Halichondrida).42 Bewley et al. performed a cellular localization study on Theonella swinhoei in which several types of microorganisms were separated from the sponge cells. Chemical analysis of the extracts from the separated cells indicated that the bicyclic peptide theopalauamide was found exclusively in filamentous bacteria while the polyketide swinholide A was localized to a mixed population of unicellular bacteria.59... 

Kelly-Borges, M. and Pomponi, S. A., Phylogeny and classification of lithistid sponges (Porifera Demospongiae) a preliminary assessment using ribosomal DNA sequence comparisons, Molec. Mar. Biol. Biotechnol., 3, 87, 1994. 

Schmidt, E.W., Bewley C.A., and Faulkner, D.J., Theopalauamide, a bicyclic glycopeptide from filamentous bacterial symbionts of the lithistid sponge Theonella Swinhoei from Palau and Mozambique, J. Org. Chem., 63, 1254, 1998. 

Bewley CA, Faulkner DJ. Lithistid Sponges star performers or... 

Lithistid sponges of the genus Discodermia have been shown to produce a variety of bioactive compounds. For example, Caribbean specimens have been the source of the cytotoxic compound polydiscamide A (6) the antifungal compounds discobahamin (7), and discodermide (8) the indole derived compound discodermindole (9) and the antitumor agent, discodermolide, (10) (Figure 2). 

An alternative supply route may be achieved through fermentation of an associated microorganism. It has been suggested that many of the compounds produced by lithistid sponges such as Discodermia may have their true origin in microbial associates. In the... 

A different approach was used by Bewley et al. (64) to localize metabolites of the Lithistid sponge Theonella swinhoei. T. swinhoei has four distinct cell populations sponge cells, unicellular heterotrophic bacteria, unicellular cyanobacteria, and filamentous heterotrophic bacteria. This sponge contains two major compounds swinholide a (Scheme 34), which is related structurally to scytophycin c a cyanobacterial metabolite and peptide-P951 (Scheme 35), which contains AHMP (3-amino-4-hydroxy-6-methyl-8-phenylocta-5,7-... 

The SIO-RU-SKB collaboration also involved the collection, in 1994 and 1995, of over 100 marine invertebrates from the Ponto do Ouro area of southern Mozambique, about 80kms north of Sodwana Bay Fig. (1). Two cyclic peptides, the known swinholide A (78) and the new bicyclic theopalauamide (79), were isolated from Mozambique specimens of the Indo-Pacific lithistid sponge Theonella swinhoei (Family Theonellidae) [79]. Interestingly, a concurrent investigation of T. swinhoei from Palau,... 

THE CHEMISTRY OF LITHISTID SPONGE A SPECTACULAR SOURCE OF NEW METABOLITES... 

The purpose of this review is to offer a comprensive survey of the chemistry of lithistid sponges with a particular emphasis to the pharmacological properties and to the mechanisms of action of their metabolites, and to report the total syntheses of representative macrolides and peptides isolated from the sponges belonging to this so fascinating order. 

To date, two excellent reviews have been published on the chemical composition of lithistid sponges [1,2]. The 1993 review Bioactive... 

In this section the secondary metabolites from lithistid sponges are described following the taxonomic classification of extant lithistid sponges reported by Faulkner [2],... 

Lithistid sponges identified as Theonella sp. are often superficially similar to Theonella swinhoei except for the orange colour of their interior tissue due to the presence of aurantoside A (1) and related polyenes. 

In a later stage we had the opportunity to investigate in our laboratories other two New Caledonian lithistid sponges, Neosiphonia superstes and Reidispongia coerulea which proved to be a rich source of biological active macrolides and cyclic peptide with unusual structures. 

The investigation of the New Caledonian lithistid sponge Corallistes fulvodesmus led to the isolation of two polynitrogen compounds, 1-methyl-pteridine-2,4-dione, previously known as a synthetic product... 

The lithistid sponge Aciculites orientalis contains three cyclic peptides, aciculitins A-C (130-132), that are identical except for homologous lipid residues [149]. The aciculitins consist of a bicychc peptide that contains an unusual histidino-tyrosine bridge. Attached to the bicyclic portion are Ci3-Ci5-dihydroxy-4,6-dienoic acids bearing D-lyxose at the C-3 position. The paper also reports the structures of the two artifacts aciculitamides A and B obtained earlier from the same sponge. The aciculitins inhibited the growth of Candida albicans and are cytotoxic toward the HCT-116 cell line. 

The chemistry of lithistid sponge a spectacular source of new metabolites 1175... 

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