Dysidea isolation from

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). 

A novel natural product has been isolated from the Micronesian sponge Dysidea herbacea. This material is the zwitterionic pyrroloimidazopyridine 293 and is claimed to be the first example of a simple peptide with an N,N-aminal linkage <2004JOC1180>. 

The indole 22 was previously isolated from the sponge Dysidea etheria [110] and has now been obtained from the Antarctic ice bacterium ARK 13-2-437. The lipid phase of Hel45 delivered additionally N-(2-hydroxyethyl)-ll-octadecen-amide and the new natural products 17-methyl-16-octadecenoic acid [95] and indole-3-carboxylic acid thiomethyl ester (23). 

More recently, the sesquiterpene A -isonakafuran-9-hydroperoxide (76) (P2j, O— O = 1.458 A, H—O—O—C = 63.3°, Figure 30) has been isolated from the dichlorometh-ane/methanol extract of the marine sponge Dysidea sp. nov . The peroxide is inhibitory to the marine fungus Trichophyton mentagrophytes and to murine leukemia cells. In view... 

Two thioacetates, thiofurodysin acetate (320) and thiofurodysinin acetate (209) were isolated from a Dysidea species from Sydney, Australia. They were converted by treatment with Raney nickel to a mixture containing furodysin and furodysinin respectively [214], These were the first thiol acetates isolated from natural sources. The absolute configurations of (-)-(6/ ,ll/ )-thiofurodysinin acetate (209), (-)-(6/ ,ll/ )-furodysinin disulfide (208) and (+)-(6/ ,ll/ )-methoxythiofurodysinin acetate lactone (321), isolated from a Fijian specimen of D. herbacea were determined by chemical interconversion [292]. 

The dysideathiazoles A-E (331-335) are a series of polychlorinated amino acid derivatives from Pacific Island collections of D. herbacea. The structures were determined by X-ray analyses and the absolute configurations were determined by X-ray crystallography of a brominated derivative [301]. Herbamide A (336), a chlorinated amide was isolated from a Papua New Guinean sample of D. herbacea as a minor component [302]. D. herbacea from the southern Great Barrier Reef contained a thiazole (337) amongst other known metabolites [303]. A Dysidea sp. 

Dysidea sp. from Bararin Island in the Philippines, has yielded the dysideaprolines A-F (341-346), proline-derived analogues of dysidenin (318). The barbaleucamides A (347) and B (348), which are structural analogues of the cyanobacterial metabolite barbamide, were also isolated. The structures were elucidated by NMR spectroscopic analysis. It is most probable that all of these compounds are derived from a symbiotic cyanobacterium found in close association with the Dysidea sp. [306]. 

There have been three reports of the same dimeric disulfide. It was first isolated from an unidentified sponge from Guam and the structure elucidated by analysis of spectral data. The (E,E) stereochemistry of the disulfide (500) was defined by comparing the I3C NMR spectroscopic data with those of the (E,Z)-isomer (501) that was obtained as an unstable minor product [425]. Compound 500 was isolated from a species of Psammaplysilla and was called psammaplin A [426]. It was also isolated from Thorectopsamma xana, collected from the same location in Guam, together with a minor dimeric metabolite bisaprasin (502). Both compounds inhibited growth of Staphylococcus aureus and Bacillus subtilis [427]. Psammaplin A (bisprasin) (500) was later isolated from a Dysidea species of sponge and shown to act on Ca2+-induced Ca2+ release channels of skeletal muscle [428]. 

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]. 

More recently, two new isonakafiiran-type sesquiterpenes were isolated from this sponge species [74], These types of compounds possess interesting antitumor and antifungal activity, and attempts to synthesize them are being conducted [75], Other bioactive metabolites, such as antifouling sesquiterpenes, have also been recently isolated from Dysidea herbacea [76],... 

Melemeleones A and B (320 and 321) possess a 4,9-friedodrimane sesquiterpene array linked to a quinone bearing a taurine and they are structurally related to avarol. Compounds 320 and 321 were isolated from the sponge Dysidea sp. and identified by analysis of their spectroscopic data. Compound 321 showed a moderate inhibitory activity against the pp60v src protein Tyrosine Kinase with an IC50 of 28 pM [236]. 

The simple herbacic acid (938) was isolated from Dysidea herbacea from the Great Barrier Reef, and may be a precursor to more complex trichloromethyl metabolites (990). Another collection of Dysidea sp. from Australia s Great Barrier Reef yielded five new metabolites (939-943) for which the absolute stereochemistry was determined by correlation with (-)-(.S )-4,4,4-trich loro-3-methyl butanoic acid (991). Dysidea herbacea from the Great Barrier Reef contains (-)-neodyside-nin (944), which is an isomer of the well-known and often isolated dysidenin. 

A study of South Pacific marine invertebrates has revealed the new 1891 in the sponge Dysidea herbacea (1760). The new 1892 was isolated from Sagaminop-teron bilealbum molluscs feeding on the sponge Dysidea herbacea from Guam waters (1761). Four samples of Dysidea sponges from the Indo-Pacific yielded the... 

Sponges produce furanosesquiterpenes of various skeletal types, such as furodysinin (118) from Dysidea herbacea and nakafuran-8 (119) from D. etheria, the latter of which is antifeeding. Similarly, mixed shikrmate-mevalonate metabolites are often encountered as sponge metabolites the first example is avarol (120), which was isolated from Dysidea avara. Several related compounds have been isolated from dictyoceratid... 

A marine sponge Dysidea sp., collected at Bararin Island, Philippines, produced a further eight polychlorinated secondary metabolites, termed dysideaprolines A-F 319-324 and barbaleucamides A 325 and B 326 <2001JNP1133>. Another two polychlorinated metabolites 327 and 328 have been isolated from the sponge Dysidea herbacea sp. 1524 collected from Lizard Island <2001T4603>. It is most probable that these compounds are actually derived from a symbiotic cyanobacterium found in close association with the Dysidea sp. 

Dysideapalaunic acid (16), which is closely related to kohamaic acids and inhibits an aldose reductase, was isolated from the marine sponge Dysidea sp. from the Palauan Sea by Nakagawa and co-workers in 1986 [22]. The Okinawan kohamaic acids have a different stereochemistry at CIS from 16 and previously isolated sesterterpenes, which are... 

During the last thirty-five years, a variety of biologically active substances bearing a novel carbon skeleton have been found in marine organisms. Of them, a number of highly brominated diphenyl ethers with antibacterial and antitumor activities were isolated from Dysidea herbaceae and Ptychodera flava laysanica. These metabolites are regarded as a self-defensive substance. In order to synthesize these metabolites, electrochemical oxidation of bromophenols has been carried out °. Some typical examples are shown here. 

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