Structure of a new sterol from the South China sponge Dysidea fragilis

A new sterol, 5a-cholesta-8(14),24(25)-diene-3/β, 6a-diol (1) and a known sterol (24Z)-24-ethyl-cholesta-7(8),24(28)-diene-3β,5a,6β-triol (2) have been isolated from the South China Seasponge Dysidea fragilis. The structure and relative stereochemistry of 1 were established by spectralanalysis, including 2D NMR experiments.     

A new sesquiterpenoid hydroquinone from the marine sponge Dysidea arenaria

Detailed chemical investigation of the South China sponge Dysidea arenaria resulted in the isolation of a new sesquiterpenoid hydroquinone, 19-hydroxypolyfibrospongol B (1), along with five known compounds: polyfibrospongol B (2), isosemnonorthoquinone (3), ilimaquinone (4), smenospongine (5) and smenotronic acid (6). The structures were determined by extensive spectroscopic analysis. The in vitro anti- HIV activity on HIV-1 RT was evaluated. Compounds 3 -6 displayed moderate inhibitory activity, with IC(50)values of 239.7, 16.4, 176.1, and 130.4 microM, respectively, while 1 and 2 were found to be inactive against the same biological target.     

Muurolane‐type sesquiterpenes from marine sponge Dysidea cinerea

Seven new muurolane‐type sesquiterpenes, (4R,5R)‐muurol‐1(6),10(14)‐diene‐4,5‐diol (1), (4R,5R)‐muurol‐1(6)‐ene‐4,5‐diol (2), (4R,5R,10R)‐10‐methoxymuurol‐1(6)‐ene‐4,5‐diol (3), (4S)‐4‐hydroxy‐1,10‐seco‐muurol‐5‐ene‐1,10‐dione (4), (4R)‐4‐hydroxy‐1,10‐seco‐muurol‐5‐ene‐1,10‐dione (5), (6S,10S)‐6,10‐dihydroxy‐7,8‐seco‐2,8‐cyclo‐muurol‐4(5),7(11)‐diene‐12‐oic acid (6), and (6R,10S)‐6,10‐dihydroxy‐7,8‐seco‐2,8‐cyclo‐muurol‐4(5),7(11)‐diene‐12‐oic acid (7) were isolated from the marine sponge Dysidea cinerea. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D‐NMR, 2D‐NMR, and CD spectra as well as by comparing the NMR data with those reported in the literature. Copyright © 2013 John Wiley & Sons, Ltd.     

Dysidavarones A-D, new sesquiterpene quinones from the marine sponge Dysidea avara

Dysidavarones A-D (1-4), four new sesquiterpene quinones possessing the unprecedented "dysidavarane" carbon skeleton, were isolated from the South China Sea sponge Dysidea avara. The structures were established by spectroscopic methods, and the absolute configurations were determined using quantum mechanical calculation of the electronic circular dichroic (ECD) spectrum and exciton chirality CD method. Their cytotoxic activity against four human cancer cell lines and PTP1B inhibitory activity were also evaluated.     

Avinosol, a meroterpenoid-nucleoside conjugate with antiinvasion activity isolated from the marine sponge Dysidea sp

[structure: see text] The new meroterpenoids avinosol (1), 3'-aminoavarone (2), and 3'-phenethylaminoavarone (3) have been isolated from the marine sponge Dysidea sp. collected in Papua New Guinea, and their structures were elucidated by analysis of spectroscopic data. Avinosol (1), which is apparently the first example of a naturally occurring meroterpenoid-nucleoside conjugate, showed antiinvasion activity in a cell-based assay.     

Bilosespens A and B: two novel cytotoxic sesterpenes from the marine sponge Dysidea cinerea

[formula: see text] Two novel sesterpenes, bilosespens A and B (1 and 2) were isolated from the Red Sea sponge Dysidea cinerea collected in the Dahlak archipelago, Eritrea. The structure of the mixture of the two inseparable compounds was established by spectroscopic analysis, mainly by 1D and 2D NMR measurements. The mixture of bilosespens A and B is cytotoxic to a few human cancer cells.     

9-Hydroxyfurodysinin-O-ethyl lactone: a new sesquiterpene isolated from the tropical marine sponge Dysidea arenaria

A new sesquiterpene, 9-hydroxyfurodysinin-O-ethyl lactone, has been isolated from a New Caledonian Dysidea arenaria, along with three known compounds. The possible incorporation of the ethyl ether from the extraction solvent is discussed.     

Two furano-sesquiterpenes from the South China Sea Sponge Dysidea fragilis

A new sesquiterpene, ent-furodysin (1), has been isolated from the South China Sea Sponge Dysidea fragilis, along with a known sesqui-terpene, ent-furodysinin (2). The structure and relative stereochemistry of 1 and 2 were established by spectral analysis.     

Novel betaines from a micronesian sponge Dysidea herbacea

Three new betaines, dysibetaine PP (1), dysibetaine CPa (2), and dysibetaine CPb (3), were isolated from an aqueous extract of the marine sponge Dysidea herbacea collected in Yap state, Micronesia. The structure of 1 was determined by spectral methods as well as chemical degradation to be a novel dipeptide betaine, and those for 2 and 3 were determined to be unprecedented cyclopropane betaines. Compounds 2 and 3 showed weak affinity toward the N-methyl-D-aspartic acid-type and the kainic acid-type glutamate receptors, respectively, in a radioligand binding assay.     

Sesquiterpenoids of the Sponge Dysidea fragilis of the North-Brittany Sea

The title sponge is shown to contain eight new sesquiterpenoids for which a common, unusual biogenetic origin is postulated. The compounds are shown to be: (–)-(1R*,4R*)-3-(3′-furyl)methyl-2-p-menthen-7-yl acetate ((–)- 8b ); two diols separated as the monoacetates (–)-(1S*,4R*)-3-(3′-furyl)methyl-l-hydroxy-2-p-menthen-7-yl acetate ((–)- 13a ) and the (–)-(1R*,4R*)-epimer (–)- 13b , the two C(4)-epimeric 4-ethoxy-3-(1′(7′),2′-p-menthadien-3′-yl)methyl-2-buten-4-olides ((+)- 14a and (–)- 14b ), (–)-3-(3′-furyl)methyl-7-nor-2-p-menthen-l-one ((–)- 11 ), (–)-(3Z)-1-(3′-furyl)-4,8-dimethylnona-3, 7-dien-2-yl acetate ((–)- 17 ), and (+)-3-(5′,7′-seco-2′(10′)-pinen-7′-yl)methylfuran ((+)- 15 ).     

Avarol and isoavarol from a Pacific Ocean sponge Dysidea sp.

Two hydroquinone-group-containing terpenoids have been isolated from a Pacific Ocean spongeDysidia, sp. One of them has been identified by physicochemical methods as the previously known avarol. The second, isoavarol, obtained for the first time, differs from avarol by the 4(11)-position of the double bond.     

Avarol and isoavarol from a Pacific Ocean sponge Dysidea sp.

Two hydroquinone-group-containing terpenoids have been isolated from a Pacific Ocean spongeDysidia, sp. One of them has been identified by physicochemical methods as the previously known avarol. The second, isoavarol, obtained for the first time, differs from avarol by the 4(11)-position of the double bond.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 358–361, May–June, 1990.     

Dysamide U,a new trichlorinated diketopiperazine from the sponge Dysidea sp.

Dysamide U,a new tricblorinated diketopiperanne(1)along with seven known ones(2-8)were isolated from the sponge of Dysidea sp.collected from the Pacific ocean.The structure of dysamide U(1)was elucidated by high resolution FARMS and 1H NMR data induding COSY and RCT-COSY.     

New tetrahydropyrans from a marine sponge

Two new tetrahydropyrans have been isolated from the sponge Haliclona sp. From chemical and spectroscopic evidence they are shown to be (1′$\text{R}$, 2$\text{S}$, 2″$\text{E}$, 5$\text{R}$, 6$\text{R}$)-2-(1′-bromethyl)-2,5-dimethyl-6-(penta-2″,4″-dienyl)-tetrahydropyran and (1′$\text{R}$, 2$\text{S}$, 5$\text{R}$, 6$\text{R}$)-2-(1′-bromoethyl)-2,5-dimethyl-6-(pent-4″-enyl)-tetrahydropyran.