Dysidea herbacea

A novel natural product has been isolated from the Micronesian sponge Dysidea herbacea. This material is the zwitterionic pyrroloimidazopyridine 293 and is claimed to be the first example of a simple peptide with an N,N-aminal linkage <2004JOC1180>. 

Capon, R.J. Faulkna, D.J. (1985) Habasterol, an ichthyotoxic 9,11-secostaol from the sponge Dysidea herbacea. J. Org. Chem., 50,4771-3. 

Dunlop, R. W. Kazlauskas, R. March, G. Murphy, P.T. Wells, R. J. (1982) New fiirano-sesquiterpenes from the sponge Dysidea herbacea. Aust. J. Chem., 35,95-103. 

Flowers, A.E. Garson, M.J. Webb, R.I. Dumdei, E.J. Charan, R.D. (1998) Cellular origin of chlorinated diketopiperazines in the dictyoceratid sponge Dysidea herbacea (Keller). Cell Tissue Res., 292, 597-607. 

Sakai, R. Oiwa, C. Takaishi, K. Kamiya, H. Te wa, M. (1999) Dysibrfaine a new a,a-disubstituted a-amino acid derivative from the marine spcmge Dysidea herbacea. Tetrahedron L., 40, 6941-4. 

Searle, P.A. Jamal, N.M. Lee, G.M. Molinsky, T.F. (1994A) Configurational analysis of new furanosesquiterpenes from Dysidea herbacea. Tetrahedron, 50, 3879-88. 

Dysidea herbacea contains linear polychlorinated peptides with a thiazole residue. The metabolites can be divided into the dysidenin, the isodysidenin and the dysideathiazole series of compounds [22]. 

Marine organisms have also been intensively examined for their sesquiterpene content. Dysidea herbacea is a sponge species which has yielded new metabolites for more than 20 years, and no doubt further collections from different locations will continue to reveal new chemistry. 

The terpenoid metabolites reported from Dysidea sp. are predominantly sesquiterpenes [72]. They possess a spiro moiety as in herbadysidolide, Fig. (5), herbasolide, Fig (6) and spirodysin, Fig. (7), or they are fiiranosesquiterpenes such as furodysinin, Fig. (8). However, Dysidea herbacea from two collection sites on the Great Barrier Reef less than 120 km apart also yielded enantiomeric fiiranosesquiterpenes [73],... 

More recently, two new isonakafiiran-type sesquiterpenes were isolated from this sponge species [74], These types of compounds possess interesting antitumor and antifungal activity, and attempts to synthesize them are being conducted [75], Other bioactive metabolites, such as antifouling sesquiterpenes, have also been recently isolated from Dysidea herbacea [76],... 

Several other marine sponges have been investigated in the last decade, in the search for novel bioactive sesterterpene molecules. A sample of the sponge Dysidea herbacea from the Red Sea is unique in that it contains cytotoxic sesterterpenes with a scalarin skeleton, e.g., scalardysin, Fig. (16) and the C2i-fiiranoterpene fiirospongolide, Fig. (17). 

Polybrominated diphenyl ethers from the Indonesian marine sponge Dysidea herbacea are active against the Gram-positive bacteria Bacillus subtilis (MIC 0.20 pg/ml) and the phytopathogenic fungus Cladosporium cucumerinum. Compounds 90 and 91 are also active in the brine shrimp lethality test (LC50 0.96 and 0.94 pg/ml) [81]. 

The simple herbacic acid (938) was isolated from Dysidea herbacea from the Great Barrier Reef, and may be a precursor to more complex trichloromethyl metabolites (990). Another collection of Dysidea sp. from Australia s Great Barrier Reef yielded five new metabolites (939-943) for which the absolute stereochemistry was determined by correlation with (-)-(.S )-4,4,4-trich loro-3-methyl butanoic acid (991). Dysidea herbacea from the Great Barrier Reef contains (-)-neodyside-nin (944), which is an isomer of the well-known and often isolated dysidenin. 

A study of South Pacific marine invertebrates has revealed the new 1891 in the sponge Dysidea herbacea (1760). The new 1892 was isolated from Sagaminop-teron bilealbum molluscs feeding on the sponge Dysidea herbacea from Guam waters (1761). Four samples of Dysidea sponges from the Indo-Pacific yielded the... 

Berthold RJ, Borowitzka MA, Mackay MA (1982) The Ultrastructure of Oscillatoria spongeliae, the Blue-Green Algal Endosymbiont of the Sponge Dysidea herbacea. Phycologia 21 327... 

Hinde R, Pironet F, Borowitzka MA (1994) Isolation of Oscillatoria spongeliae, the Filamentous Cyanobacterial Symbiont of the Marine Sponge Dysidea herbacea. Mar Biol 119 99... 

Clark WD, Crews P (1995) A Novel Chlorinated Ketide Amino Acid, Herbamide A, from the Marine Sponge Dysidea herbacea. Tetrahedron Lett 36 1185... 

Dumdei EJ, Simpson JS, Garson MJ, Byriel KA, Kennard CHL (1997) New Chlorinated Metabolites from the Tropical Marine Sponge Dysidea herbacea. Aust J Chem 50 139... 

MacMillan JB, Molinski TF (2000) Herbacic Acid, a Simple Prototype of 5,5,5-Trichloro-leucine Metabolites from the Sponge Dysidea herbacea. J Nat Prod 63 155... 

MacMillan JB, Trousdale EK, Molinski TF (2000) Structure of (-)-Neodysidenin from Dysidea herbacea. Implications for Biosynthesis of 5,5,5-Trichloroleucine Peptides. Org Lett 2 2721... 

Dumrongchai N, Ponglimanont C, Stapleton BL, Garson MJ (2001) Chemical Diversity in the Tropical Marine Sponge Dysidea herbacea. ACGC Chem Commun 13 17... 

Trousdale EK, Taylor SW, Parkin S, Hope H, Mokinski TF (1998) Reductive Dechlorination of Dysidenin from Dysidea herbacea. Structure of a Novel Binuclear Zinc Metallo-cycle. Nat Prod Lett 12 61... 

Flowers AE, Garson MJ, Webb RI, Dumdei EJ, Charan RD (1998) Cellular Origin of Chlorinated Diketopiperazines in the Dictyoceratid Sponge Dysidea herbacea (Keller). Cell Tissue Res 292 597... 

Anjaneyulu V, Nageswara Rao K, Radhika P, Muralikrishna M, Connolly JD (1996) A New Tetrabromodiphenyl Ether from the Sponge Dysidea herbacea of the Indian Ocean. Indian J Chem 35B 89... 

Handayani D, Edrada RA, Proksch P, Wray V, Witte L, Van Soest RWM, Kunzmann A, Soedarsono (1997) Four New Bioactive Polybrominated Diphenyl Ethers of the Sponge Dysidea herbacea from West Sumatra, Indonesia. J Nat Prod 60 1313... 

Bowden BF, Towerzey L, Junk PC (2000) A New Brominated Diphenyl Ether from the Marine Sponge Dysidea herbacea. Aust J Chem 53 299... 

Agrawal MS, Bowden BF (2005) Marine Sponge Dysidea herbacea Revisited Another Brominated Diphenyl Ether. Mar Drugs 3 9... 

Unson, M. D. and Faulkner, D. J., Cyanobacterial symbiont biosynthesis of chlorinated metabolites from Dysidea herbacea (Porifera), Experientia, 49, 349, 1993. 

Bandaranayake, W. M., Bemis, J. E., and Bourne, D. J., Ultraviolet absorbing pigments from the marine sponge Dysidea herbacea isolation and structure of a new mycosporine, Comp. Biochem. Physiol., 115C, 281, 1996. 

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