Bioactivity sponges

A second group of bioactive sponge metabolites with an unusual structural motif are the terpene isocyanides, which often co-occur with structurally related isothiocyanates and forma-mides.157-159 Less commonly encountered nitrogenous based substituents present in sponge terpene metabolites include isocyanates, thiocyanates, and dichloroimines (carbonimidic dichlorides). The biochemistry and ecology of these unique marine metabolites have been targeted for study by numerous researchers.159 160... 

Fusetani N, Matsunaga S. Bioactive sponge peptides. Chem. Rev. 1993 93 1793-1806. 

Gerwick WH, Tan LT, Sitachitta N (2001) Alkaloids of marine cyanobacteria. In Cordell GA (ed) The Alkaloids, vol 57. Academic Press, San Diego, p 75 Fusetani N, Matsunaga S (1993) Bioactive sponge peptides. Chem Rev 93 1793 Shimizu Y (1993) Microalgal metabolites. Chem Rev 93 1685... 

Calcul, L., Chow, R., Oliver, A.G., Tenney, K., White, K.N., Wood, A.W., Fiorilla, C and Crews, P. (2009) NMR strategy for unravehng structures of bioactive sponge-derived oxy-polyhalogenated diphenyl ethers,/, Nat. Prod., 71, 443-449. 

Two other pyrrolopyrimidine nucleoside antibiotics, mycalisines A and B (56,57), have been isolated from the sponge Mycale sp. (173). These bioactive marine metaboHtes inhibit cell division of starfish eggs. 

HO-./ T V-NH Blue-green algae -Anabaena laxa Marine sponge -Callyspongia abnormis Laxaphycins A and E -antifungal peptides Callynormine A - no bioactivity has been reported 246-248 249... 

Kirsch G Koeng GM, Wright AD, Kamisnky RA. (2000) New bioactive sesterterpene and antiplasmodial alkaloids from marine sponge Hyrtios. JNat Prod 63 825-829. 

Fusetani N, Asai N, Matsunaga S, Honda K, Yasumuro K. (1994) Bioactive marine metabolities. 59. CyclosteUettamines A-F, pyridine alkaloids which inhibit binding of methyl quinuclidinyl benzylate (QNB) to muscarinic acetylcholine receptors, from the marine sponge, Stelletta maxima. Tetrahedron Lett 35 3967-3970. 

Similarly to the latter two examples, there are many other defense toxins isolated from a variety of invertebrates, sponges, tunicates, sea urchins, sea cucumbers, and others. Many of the latter compounds are bioactive. ... 

The basic alkaloid in Pilocarpus jaborandi (Rutaceae) is pilocarpine, a molecule of which contains an imidazole nucleus and is also used as a clinical drug. During alkaloid synthesis, L-histidine can produce the manzamine nucleus (Figure 27). These alkaloids are quite widespread, though they were first isolated in the late 1980s in marine sponges. They have an unusual polycyclic system and a very broad range of bioactivities. Common alkaloids with this nucleus include manzamine A, manzamine B, manzamine X, manzamine Y, sextomanzamine A and so on. 

Manzamine alkaloids can be isolated from marine sponges. They often contain /3-carboline. This group has a diverse range of bioactivities. It also has its own way of establishing its structures. An intramolecular Diels-Adler reaction for manzamines has been proposed. The a is bisdihydropyridine (derived probably from amonia), and the (3 is intramolecular cycloaddition in a pentacyclic... 

The relative contribution to the cup of natural products by marine and terrestrial organisms is outlined in Table 9.1. Column entries are the phylum, class or order, number of species, biogenetic class of metabolites produced, their bioactivity level, and a qualitative indication as to the average molecular complexity (Whitlock 1998). The latter property receives closer attention in Table 9.II for specific molecular skeletons. These data warrant several conclusions. First, unusual secondary metabolites on land derive mostly fi-om green plants and arthropods, while in the sea are the algae, sponges, cnidarians, bryozoans, and ascidians that give most. This is true no matter if the molecular skeleton, or the actual metabolite, or even the bioactivity, is examined. 

Bifiilco, G. Bruno, I. Minale, L. Riccio, R. Debitus, C. Bourdy, G. Vassas, A. Lavayre, J. (1995B) Bioactive prenyIhydroquinone sulfates and a novel C3 j furanoterpene alcohol sulfate from the marine sponge Ircinia sp. J. Nat. Prod., 58, 1444-9. 

D Ambrosio. M. Guerriao, A. IMiitus, C. Pietra, F. (1996B)Leucascandrolide A, anewtypeofmacrolide the first powafully bioactive metabolite of calcareous sponges Leucascandra caveolata, a new genus from the Coral Sea) Helv. Chim. Acta, 79, 51-60. 

Highly enantioenriched 4-alken-l-yn-3-ol moieties present in many bioactive acetylenic metabolites from sponges have been efficiently obtained by reduction of the parent 1-trimethylsilyI-4-alken-l-yn-3-one 18 with Alpine-borane or with BH3-SMe2 in the presence of chiral oxazaborolidines, followed by desilylation of the resulting alcohol. This strategy has been applied to the first stereoselective synthesis of petrofuran 19 <99SL429>. 

A number of triterpenoids are bioactive compounds and are used in medicine. For example, fusidic acid is an antimicrobial fungal metabolite, isolated from Fusidium coccineum, and cytotoxic dimeric triterpenoids, crellastatins, are isolated from marine sponges Crella species. 

Bioactive Compounds from Marine Sponges and Their Symbiotic Microbes A Potential Source of Nutraceuticals... 

Sponges are considered as the chemical factory in marine environment because of its immense production of chemically diverse compounds. Other than the chemical diversity, these compounds possess remarkable bioactivities. This great potential has aroused applications of sponge-derived compounds as therapeutics and at present, a number of promising compounds are in clinical and preclinical trials. Recently, nutraceuticals have received considerable interest among the health conscious community because of its multiple therapeutic effects. Natural health-promoting substances... 

---