Californian sponge

A Californian sponge of the Halichondriidae family contained a sulfated sesterterpene hydroquinone and five sulfated sesterterpenes. The structures of the halisulfates 1-5 (359-363) were determined by interpretation of spectral data and a structure was proposed for halisulfate 6 (364). The halisulfates are antimicrobial and antiinflammatory [318]. The absolute configuration of halisulfate 3 (361), which was also isolated from Ircinia sp. from the Philippines, has been determined by application of the chiral amide method and by chemical degradation techniques [319]. Halisulfate 7 (365) is a sesterterpene sulfate from a Coscinoderma sp. from Yap, Micronesia [320]. 

Halisulphate 2 (87), a sulphated sesterterpene with a monocarbocyclic skeleton related to cyclolinteinone, was isolated from the Californian sponge Halichondria sp. [104], Halisulphate 2 showed anti-microbial activity against S. aureus, C. albicans and B. subtilis at 20 pg/disk, it inhibited mouse ear oedema after topical application and was an inhibitor ofPLA2 [104],... 

A sesquiterpene isothiocyanate (240) was isolated from the Californian nudibranch Cadlina luteomarginata but was presumed to be concentrated from the Axinella species of sponge which constitutes much of its diet [249]. Famesyl isothiocyanate (241) was isolated from Pseudaxinyssa pitys [250], while theonellin isothiocyanate (242) was isolated from the sponge Theonella cf. swinhoei [251]. 

Thompson et al. have investigated the ecological role of the brominated isoxazoline alkaloids, aerothionin (Structure 2.84) and homoaerothionin (Structure 2.89), in Californian specimens of A. fistularis.134 139 The alkaloids caused behavioral modification in marine invertebrates, were toxic to dorid nudibranchs other than one specialized feeder, inhibited the settlement and/or metamorphosis of invertebrate larvae, and were strongly antimicrobial and cytotoxic. Sponges exuded significantly more of these two alkaloids when wounded,155 and, consistent with their defensive role, the metabolites were found to be localized in spherulous cells close to the aquiferous exhalant canals.156... 

In a short formal synthesis of the Californian red scale pheromone 271, Claisen orthoester rearrangement has been employed as a key step [60] (Scheme 6.44). Stereoselective synthesis of the trisubstituted double bond in a component of Caribbean sponge 274 was accomplished with the Claisen-Johnson rearrangement as depicted in Scheme 6.44 [61]. A similar strategy was developed for the stereoselective synthesis of the pheromone 277 of square necked grain (Scheme 6.44) [62]. 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

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