Transformation of tricyclic makaluvamines from the marine sponge Zyzzya fuliginosa into damirones

Makaluvamines H and C isolated from the marine sponge Zyzzya fuliginosa were transformed into damirones A and B, respectively, by alkaline hydrolysis. The crystal structure of damirone A was established by X-ray diffraction analysis.     

UV-stability and UV-protective activity of alkaloids from the marine sponge Zyzzya fuliginosa

Alkaloids from the marine sponge Zyzzya fuliginosa damirones A (1) and B (2); makaluvamines H (3), C (4), G (5), and L (6); and zyzzyanones A (8) and B (9) were investigated for the ability to protect egg-cell membranes of the sea urchin Strongylocentrotus nudus from UV-radiation. Damirones, zyzzyanones, and tricyclic makaluvamines C (4) and H (3) exhibited the greatest membrane-protective activity. It was shown that makaluvamines G (5) and L (6) were converted by UV-irradiation into damirones A (1), B (2), tricyclic makaluvamines H (3), C (4), and zyzzyanones A (8) and B (9), respectively. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 62–64, January–February, 2006.     

1,3-dimethylisoguaninium,an antiangiogenic purine analog from the sponge Amphimedon paraviridis

An antiangiogenic purine analog, 1,3-dimethylisoguaninium (1), was isolated from the ethanol (EtOH) extract of the Okinawan sponge Amphimedon paraviridis. The structure was elucidated on the basis of its spectral properties and X-ray crystallographic analysis. Compound 1 exhibited specific inhibition of the basic fibroblast growth factor (bFGF)-induced proliferation of bovine aorta endothelial cells (BAECs). Moreover, compound 1 reduced the tube formation of BAECs in a time-dependent manner.     

Halichonadins A-D, new sesquiterpenoids from a sponge Halichondria sp.

A new dimeric sesquiterpenoid with two eudesmane skeletons through a urea linkage, halichonadin A (1), as well as three new eudesmane sesquiterpenoids having a carbamate, an isonitrile, or an amino functionality, halichonadins B (2), C (3), and D (4), respectively, have been isolated from a marine sponge Halichondria sp., and the gross structures and relative stereochemistry of 1-4 were elucidated on the basis of spectral data and chemical means.     

Halichonadins G-J, new sesquiterpenoids from a sponge Halichondria sp.

Three new dimeric sesquiterpenoids, halichonadins G-I (1-3), and one new eudesmane sesquiterpenoid possessing a 1-phenethyl urea moiety, halichonadin J (4), were isolated from a marine sponge Halichondria sp. Halichonadins G (1) and H (2) are homo-dimers of eudesmane sesquiterpenoid, linked through a methyl 2-{1-(2-amino-2-oxoethyl)ureido}acetate fragment and a 2-hydroxymalonamide fragment, respectively, while halichonadin I (3) is a new hetero-dimer of eudesmane sesquiterpenoid linked through a urea fragment. The structures of 1-4 were elucidated on the basis of spectroscopic data.     

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.     

Halichonic acid,a new rearranged bisabolene-type sesquiterpene from a marine sponge Halichondria sp.

A new compound, halichonic acid (1), was isolated from a marine sponge Halichondria sp., together with (6R,7S)-7-amino-7,8-dihydro-α-bisabolene (2). The structure of 1 was elucidated by spectroscopic analysis and ECD spectrum calculation to be a rearranged bisabolene-type sesquiterpene having a 3-azabicyclo[3.3.1]nonene moiety. Compound 2 was cytotoxic against HeLa cells with an IC₅₀ value of 50?μM, whereas 1 did not show cytotoxicity even at 50?μM. It is possible that 1 is biosynthesized from farnesyl pyrophosphate and glycine, with rearrangement.     

Structure of ulososide A,a new triterpenoid glycoside from theUlosa sp. sponge

A new triterpenoid glycoside, (20S,22S,23R,24S)-3,22,23-trihydroxy-3-O-[O-(-D-glucuronopyranosyl)-(16)-(-D-glucopyranosyl)]-14-nor-24-methyllanost-8(9)-en-31-oic acid (ulososide A), has been isolated from the sponge Ulosa sp. and characterized.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1326–1329, July, 1994.     

Halioxepine, a new meroditerpene from an Indonesian sponge Haliclona sp

Chemical investigations on a sponge Haliclona sp. found a meroditerpene 1 having a new carbon skeleton. By analyzing spectroscopic data, the structure was elucidated to comprise a substituted hydroquinone, a tetrahydrooxepine, and a cyclohexene, and these components were united with C1 and C2 units. Compound 1 showed moderate cytotoxicity against NBT-T2 cells with IC50 4.8 μg/ml and also antioxidant activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 3.2 μg/ml.     

Duryne,a new cytotoxic agent from the marine sponge Cribrochalinadura

Duryne, 1, a cytotoxic metabolite which inhibits the growth of both mouse and human tumor cell lines invitro has been isolated from the marine sponge Cribrochalinadura. Its structure has been assigned by spectral methods.     

Agelasine G, a new antileukemic alkaloid from the Okinawan marine sponge Agelas sp.

A new antileukemic alkaloid, agelasine G (1a), has been isolated from the Okinawan marine sponge Agelas sp. and its structure elucidated to be a bromopyrrole alkaloid containing 9-methyladenine and diterpene moieties on the basis of the spectroscopic data.     

Benzosceptrin C, a new dimeric bromopyrrole alkaloid from sponge Agelas sp.

A new dimeric bromopyrrole alkaloid possessing a benzocyclobutane ring, benzosceptrin C (1), has been isolated from an Okinawan marine sponge of the genus Agelas (SS-956), and the structure and relative stereochemistry were elucidated from spectroscopic data. Benzosceptrin C (1) showed antimicrobial activity.     

Dactylospongiaquinone, a new meroterpenoid from the Australian marine sponge Dactylospongia n. sp.

Chemical investigation of the sponge Dactylospongia n. sp. collected near Mooloolaba, S.E. Queensland, has led to the isolation of dactylospongiaquinone (7) together with the known quinones (2-5). The new metabolite 7 possesses a different carbon framework from the known dictyoceratidaquinone (9) and is suggested to possess a cis-fused ring junction by extensive NOESY studies combined with molecular modelling calculations. The relative stereochemistry of the previously described cyclospongiaquinone-1 (3) and dehydrocyclospongiaquinone-1 (4) is also assigned on the basis of NOESY analyses. Full NMR spectroscopic assignments are provided for all compounds.     

Muqubilin,a new c24-isoprenoid from a marine sponge

The Red Sea sponge $\text{Prianos}$ sp. contains a cyclic peroxide C₂₄ - nor sesterterpene, Muqubilin ($\text{1}$). The structure of $\text{1}$ was deduced from spectroscopic data and by chemical degradation.     

Villarinol, a new alkenoyloxyalkenol derivative from the endemic Philippine Rubiaceae species Villaria odorata

Villarinol (1), a new alkenoyloxy alkenol metabolite, has been isolated from the dichloromethane extract of Villaria odorata, an endemic Rubiaceae Philippine plant, along with the known compounds stigmasterol and 4-hydroxybenzaldehyde. The structure of 1 was elucidated on the basis of spectroscopic and spectrometric studies. The extracts of V. odorata exhibited moderate inhibition against Mycobacterium tuberculosis H37Rv, based on the colorimetric microplate alamar blue assay.     

Cyclosmenospongine, a new sesquiterpenoid aminoquinone from an Australian marine sponge Spongia sp.

A new sesquiterpenoid aminoquinone, cyclosmenospongine (1), containing a dihydropyran ring, was isolated from an Australian marine sponge Spongia sp., along with the known metabolites, smenospongiarine, ilimaquinone and smenospongine. The structure of 1 was determined from spectroscopic data.     

Diplopuupehenone, a new unsymmetrical puupehenone-related dimer from the marine sponge Dysidea sp.

A new unsymmetrical puupehenone-related dimer, diplopuupehenone, comprising puupehenone and puupehenol segments, was isolated from the marine sponge Dysidea sp., along with the known metabolites, puupehenone and bispuupehenone. The structure of diplopuupehenone was established from spectroscopic data and by spectroscopic analysis of an acetoxy derivative. Diplopuupehenone showed 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity with an IC₅₀ value of 8 μM.