Theopalauamide from Theonella swinhoei

Theonellamides A-E (1104-1108), which are analogs of the previously isolated theonellamide F (7), were characterized from the Japanese sponge Theonella sp. (7725). The related theopalauamide (= P951) (1109) was isolated from Theonella swinhoei found in both Palau and Mozambique (1126,1127). It should be noted that a minor structural correction (misplaced methyl group) has been reported for the previously known theonegramide (1128). 

Schmidt EW, Bewley CA, Faulkner DJ (1998) Theopalauamide, a Bicyclic Glycopeptide from Filamentous Bacterial Symbionts of the Lithistid Sponge Theonella swinhoei from Palau and Mozambique. J Org Chem 63 1254... 

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... 

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. 

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,... 

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