Agelas

A saponin-like substance, agelasine, was isolated from Agelas dispar (10). Suber-itine from Suberites domcunculus was originally isolated by Richet (32) and was shown to be heat labile and have a MW of 28,000 by Cariello et al. (33). A cyclic peptide, dolastin, was isolated from Dolabella awicularia (34). 

Aeromonas species producing sodium channel blockers, 80r,82 Agelas dispar, 320... 

Agelas nakamurai from Japan produced the sesquiterpene sulfone, agelasidine A (353), which possessed antispasmodic activity. The structure was deduced from spectral data [309]. A simple synthesis of agelasidine A (353) utilised a hetero-Claisen rearrangement [310]. A biomimetic synthesis of 353 was also reported [311] and another synthesis of agelasidine A (353) was carried out in three steps from famesol [312]. 

Mauritamide A (481), a taurine-containing metabolite, was isolated from the sponge Agelas mauritiana [411]. The taurine-containing alkaloids tauroacidins A (482) and B (483) were isolated from a Hymeniacidon sp. from Okinawa and are tyrosine kinase inhibitors [412]. An imidazole alkaloid, (9 )-clathridine 9-A-(2-sulfoethyl)-imine (484), a taurine derivative of clathridine, was isolated from the calcareous sponge... 

The pyrrole-imidazole alkaloid taurodispacamide A (486) has been isolated from the Mediterranean sponge Agelas oroides. The structure was established from spectroscopic data. Taurodispacamide A (486) exhibited antihistaminic activity when tested on guinea pig ileum [415]. 

The sponge Agelas dispar from the Bahamas contained pyridinebetaine B (494) [420]. Echinoclathrines B-C (495-496) are members of a new class of pyridine alkaloids from an Okinawan species of Echinoclathria. They exhibit weak immunosuppressive activity [421]. 

Bromopyrrole-2-carbamide (116) was isolated from the Papua New Guinean sponge Agelas nakamurai. It exhibits antimicrobial activity against Staphylococcus aureus (IC50 0.78 pg/ml) and other bacteria and fungi [92]. 

Oroidine (138) and its dimer mauritiamine (139) from the sponge Agelas mauritiana inhibit larval metamorphosis at ED50 values of 19 and 15 (jg/ml, whereas 4,5-dibromopyrrole-2-carbamide promotes larval metamorphosis of the ascidian Ciona savignyi at a concentration of 2.5 (jg/ml [109]. 

Agelasidines A-D (275-279) are a series of terpene derivatives of hypotaurocyamine and were isolated from sponges of the genus Agelas. Agelasidine B (276) and (+)-C (277) were obtained from the Okinawan A. nakamurai [201] while agelasidines (-)-C (278) and D (279) were isolated from the Caribbean A. clathrodes [202]. The structures of these compounds were elucidated by interpretation of spectral data and by... 

Fig. 3.11 Agelas sp. An example of a very common marine sponge that produces a wide variety of halogenated metabolites such as the brominated fatty acids 733 and 734 (Photo J. R. Pawlik)...

Most of the known natural brominated pyrrole alkaloids are found in sponges, and several new examples were isolated since the first survey (1). Reviews are available that discuss the occurrence and syntheses of these metabolites (1236-1238). The Papua New Guinea sponge Agelas nakamurai has yielded the new simple pyrroles 1222 and 1223 (1239). The dibromo analog (1224) of 1223 along with enantiomeric lactams 1225/1226, which were separated by chiral HPLC, and... 

Longamide B (1232) was found in the Caribbean sponge Agelas dispar... 

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