Dysidea fragilis

Dysidazirine 130 was isolated by Ireland in 1988 from a Fijian sample of the marine sponge Dysidea fragilis [194] as the major lipophilic component of the sponge and was shown to possess cytotoxic activity against L1210 cells, as well as... 

The first compound is an antibiotic isolated from Streptomyces aureus [20], while the second compound is a cytotoxic antibiotic isolated from Dysidea fragilis, a marine sponge [21]. A logical approach to the synthesis of azirines would be an elimination reaction of a suitably M-substituted aziridine. Thus, AT-chlorination of aziridine-2-carboxylic esters was carried out using ferf-butyl hypochlorite (Scheme 8). 

Guella, G. Guerriero, A. Pirtra, F. (1985) Sesquitopoioids of the sponge Dysidea fragilis of the North-Brittany sea. Helv. Chim. Acta, 68, 39-48. 

Molinski, T.F. Ireland, C.M. (1988) Dysiazirine, a cytotoxic azacyclopropene from the marine sponge Dysidea fragilis. J. Org. Chan., 53,2103-5. 

An unusual 6a-sterol sulfate (557) was isolated from Dysidea fragilis, from the Venetian lagoon and displayed cytotoxicity against two different tumour cell lines in vitro [460]. Tamosterone sulfates (558-559) are a C14 epimeric pair of polyhydroxylated sterols isolated from a new species of Oceanapia [461]. The Japanese marine sponge Epipolasis sp. contained the steroid polasterol B sulfate (560) along with the known compound halistanol sulfate (532). The structure of compound 560 was determined on the basis of spectroscopic evidence and a chemical conversion [462]. 

A collection of the red alga Plocamium cartilagineum from Corsica and the Maltese Islands has yielded the four new halogenated homosesquiterpenic fatty acids 767-770 (843). The Pohnpei sponge Dysidea fragilis contains the novel (4 )-... 

Reef provided 920-922, and the absolute configuration of the latter metabolite was established as shown (985). Dysidea fragilis from the South China Sea has yielded dysamide D (923) (986), and Dysidea chlorea from Micronesia afforded 12 new polychlorinated diketopiperazines, dysamides I-T (924—935) (987). In addition, this study (987) confirmed the structure of dysamide E (936) (988). Based on previous assignments the absolute configurations of 924—936 are believed to be those indicated. A Pacific Ocean collection of Dysidea sp. provided dysamide U (937), which is the first trichlorinated member of the diketopiperazine family to be identified (989). 

Salomon CE, Williams DH, Faulkner DJ (1995) New Azacyclopropene Derivatives from Dysidea fragilis Collected in Pohnpei. J Nat Prod 58 1463... 

Fu X, Zeng L-M, Su J-Y, Pais M (1997) A New Diketopiperazine Derivative from the South China Sea Sponge Dysidea fragilis. J Nat Prod 60 695... 

Dysidea fragilis Ent-furodysinin Vesicles within unspecifed cells Yes 85... 

The /V-allylketene N,O-acetal rearrangement methodology has been successfully applied in natural product synthesis. For example, an asymmetric aza-Claisen rearrangement of the cyclic substrate 14 [ 5,6) rearrangement] is the key step in the total synthesis of (+ )-dihydropalles-censin-2 (isolated from the marine sponge Dysidea fragilis)648. 

The non-isoprenoid aromatic ester methyl nidorellaurinate (684) has been synthesized. Another non-isoprenoid compound is upial (685), which has been isolated from the marine sponge Dysidea fragilis. It possesses the rare bicyclo[3.3.1]octyl system and possibly it is related to microcionin-4 (686),... 

Isol. from Fijian marine sponge, Dysidea fragilis. Low melting solid, [a] —165° (c, 0.5 in MeOH). 

Schulte, G., P.J. Scheuer, and O.J. McConnell 221. Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties. Helv. Chim. Acta 63, 2159 (1980). Guella, G., a. Guerriero, P. Traldi, and F. Pietra Penlanfuran, a New Furanoid Sesquiterpene from the Marine Sponge Dysidea fragilis (Mont.) of Brittany. A Striking Difference with the Same Hawaiian Species. Tetrahedron Lett. 24, 3897 (1983). 

Guella, G., A. Guerriero, and F. Pietra 4. Sesquiterpenoids of the Sponge Dysidea fragilis of the North-Brittany Sea. Helv. Chim. Acta 68, 39 (1985). 

Schulte, G., P.J. Scheuer, and O.J. McConnell Upial, a Sesquiterpenoid Bicy-clo[3.3.1]nonane Aldehyde Lactone from the Marine Sponge Dysidea fragilis. J. Org. Chem. 45, 552 (1980). 

The species Dysidea fragilis, harvested in Pohnpei (Ant atoll) yielded four cytotoxic derivatives with an azacydo-propene cycle (long-chain 2H-azirine), which is rare in nature (Molinski and Ireland, 1988 Salomon, Williams, and Faulkner, 1995). The biosynthesis of these atypical... 

Salomon, C.E., Williams, D.H., and Faulkner, D.J. (1995) New azacyclopropene derivatives from Dysidea fragilis collected in Pohnpei./. Nat. Prod.. 58,1463-1466. 

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