Pseudaxinyssa

An unusual series of nonterpenoid aliphatic isothiocyanates from a Fijian Pseudaxinyssa sp. was evident by their strong IR absorption [68]. After silica gel and reverse-phase HPLC experiments, the structures of (Z,Z)-1,18-diisothiocyanooctadeca-1,17-diene (134, n = 14), mp 15°C, and seven other di-olefinic a,mono-olefinic a, o>bisisothiocyanates (135, n = 9-18) and three a-isothiocyano-co-formyl mono-olefins (136, n = 9, 15, 16) were also identified by spectral data... 

Biological specificity is a paramount consideration if one considers two examples, Acanthella pulcherrima [20] and Pseudaxinyssa sp. [68], That thiocyanate ion may be the precursor to marine isothiocyanates should be tested on these organisms since isothiocyantes were the primary representative of the triad. Also, should incorporation of thiocyanate ion by Phycopsis terpnis yield 81 and 82 [48], rather than the unreported corresponding isothiocyanates, the biospecificity of marine organisms will be demonstrated. 

Zimmerman, M.P. (1989) The distribution of lipids and sterols in cell types from the marine sponge Pseudaxinyssa sp. Lipids, 24, 210-6. 

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]. 

A series of eighteen long chain, aliphatic a,a)-bis-isothiocyanates (297-314) and three a-isothiocyano-o-formyl analogues (315-317) was isolated from a Fijian species of Pseudaxinyssa [287]. The major constituents (297), (305) and (315) all have the same length of aliphatic chain (Cl8). Unlike terpenoid isothiocyanates, this series was not accompanied by the corresponding isocyanides or formamides. 

A Japanese species of Epipolasis contained five sterol sulfates named halistanol sulfates A-E (536-540), which differ from the original halistanol sulfate (532) from Halichondria moorei [449]. Structures were elucidated by spectroscopic and chemical techniques. Halistanol sulfates F-H (541-543) are three additional sterol sulfates from Pseudaxinyssa digitata that inhibit HIV in vitro [450]. 

Two acyclic diterpene tetraene isothiocyanates have been isolated from sponges so far. Famesyl isothiocyanate (220) was obtained from Pseudaxinyssa pitys [184] while compound (+)-221 was isolated from Halichondria sp. [185]. Their structures were elucidated by interpretation of their spectral data. 

Stevensine (17), which is related to oroidin (13) by oxidative cyclization, was isolated from an unidentified Micronesian sponge (43). The identical compound (17), named odiline, was obtained from aqueous extracts of a New Caledonian sponge, Pseudaxinyssa cantharella (44). This sponge also contained many other oroidin analogs dibromocantharelline [(+) -18], compounds 19, 20, 21, and (+)-dibromophakeline (22). The... 

Three hemolytic constituents were isolated from the Japanese hy-droid Solanderia secunda and identified as l-hexadecyl-sn-glycerol-3-phosphorylcholine (311), 1 -tetradecyl-sw-glycerol-3-phosphorylcholine (312), and l-(l-hexadecenyl)-s/i-glycerol-3-phosphorylethanolamine (313) (254) Eighteen long-chain aliphatic a,w-bisisothiocyanates (314-331) and three a-isothiocyano-w-formyl compounds (332-334) were isolated from a Fijian sponge (Pseudaxinyssa sp.) (255). 

Girolline (46), which is a potent cytotoxin isolated from the sponge Pseudaxinyssa cantharella, inhibits protein synthesis (2). 

The antitumor marine natural product girolline (35) has been isolated from the marine sponges Pseudaxinyssa cantharella and Axinella brevistyla. Treatment with girolline causes tumor cell lines to accumulate polyubiqui-tinated p53 but does not directly inhibit proteasome activity. Girolline may represent an interesting molecular probe of the ubiquitin-proteasome in tumor cells, since it is believed to prevent the recruitment of ubiquitinated proteins and may interfere with the function of adaptor proteins required for recruitment of polyubiquitinated proteins. 

Interest in the metabolites of marine organisms remains undiminished (see, e.g. Vol. 8, pp. 65,66,75,79,82,101,108). A detailed investigation of the terpenoid constituents of the Indo-Pacific sponge Pseudaxinyssa pitys) has resulted in the isolation of several novel carbonimidic dichlorides (38)—(42). It has been... 

Wratten, S.J. and Faulkner, D.J., 1977. Carbonimidic dichlorides from the marine sponge Pseudaxinyssa pitys. J. Am. Chem. Soc., 99 7367—7368. 

Sulfated sterols Ibisterol trisodium sulfate (280), Halistanol trisodium sulfate (281),26-Methylhalist-anol trisodium sulfate (282), 25-Demethylhalistanol trisodium sulfate (283) Sponge Spp., Topse-nlia, HaUchondria cf. moorei, Pseudaxinyssa digitata HlV-1, HIV-2 Cytotoxicity, HIV-RT [207]... 

An alkaloid from the sponge Pseudaxinyssa cantha-rella, C6H11CIN4O, Mr 190.63, as dihydrochloride (giracodazoie) powder, [ajS -h8° (CH3OH). G. inhibits protein biosynthesis and has antineoplastic activity. lit. Biochem. Pharmacol. 43, 1717 (1992) Tetrahedron 45, 6713 (1989) 48, 4327 (1992) Tetrahedron Lett. 32, 1419,... 

De Nanteuil, G., Ahond, A., Guilhem, J., Poupat, C., Tran Hun Dan, E., Potier, P., Pusset, M., Pusset, J., Laboute, P., (1985). Marine invertebrates from the New Caledonian lagoon V Isolation and identification of metabolites of a new species of sponge, Pseudaxinyssa cantharella. Tetrahedron 41,6019-6033. 

Constit. of the marine sponge Pseudaxinyssa sp. l,2 Dihydro [111603-05-5]. 1,12-Diisothiocyanato-l-dodecene... 

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