A new cyclostellettamine from sponge Amphimedon compressa

A new compound,8,8′-dienecyclostellettamine,was isolated from the marine sponge Amphimedon compressa.Its structure was elucidated by spectroscopic methods including ID and 2D NMR,UV,IR,ESI-MS,MALDI-MS techniques.It is probably an important precursor of the manzamine alkoids,and also showed vigorous antibacterial activities.     

Ageladine A: an antiangiogenic matrixmetalloproteinase inhibitor from the marine sponge Agelas nakamurai

A novel MMP inhibitor, ageladine A (1) with antiangiogenic activity was isolated from a marine sponge Agelas nakamurai. Structure 1 was determined by a combination of spectroscopic and chemical methods to be an unprecedented structure of 4-(4,5-dibromo-1H-pyrrol-2-yl)]-1H-imidazo[4,5-c]pyridin-2-amine.     

Amphimelibiosides A-F, six new ceramide dihexosides isolated from a Japanese marine sponge Amphimedon sp

Six new ceramide dihexosides, amphimelibiosides A-F (1-6), were isolated from a Japanese marine sponge Amphimedon sp. The structure of amphimelibioside C (3), which is a major component of amphimelibiosides, was determined by 2D NMR techniques, chemical degradation, and a semisynthetic method to be 1-O-[beta-D-glucopyranosyl-(1-->6)-alpha-D-galactopyranosyl]-(2S,3S,4R,6E)-2-[(2'R)-2-hydroxydocosanoyl]-2-amino-6-octadecene-1,3,4-triol. The structures of the other constituents were elucidated by a combination of mass spectra, (1)H NMR, and GC-MS analysis.     

3,7-Dimethylguanine, a new purine from a Philippine sponge Zyzzya fuliginosa.

A new purine 3,7-dimethylguanine (1) has been isolated from the marine sponge Zyzzya fuliginosa, along with the known metabolites, makaluvamines A, C, K (2--4), 4-hydroxyphenylacetic acid (5), methyl ester of 4-hydroxyphenylacetic acid (6), 4-hydroxyphenethyl alcohol (7), L-phenylalanine (8) and L-tryptophan (9). The structure of 3,7-dimethylguanine (1) was elucidated by analysis of 1D and 2D (one- and two-dimensional) NMR [HMQC (heteronuclear multiple quantum coherence), gHMBC (heteronuclear multiple bond connectivity), 1H-15N gHMBC] data, mass spectroscopy data, and by comparison with 3,7-dimethylisoguanine (10).     

1,3-dimethyl-8-oxoisoguanine, a new purine from the New Zealand ascidian Pseudodistoma cereum

A new purine, 1,3-dimethyl-8-oxoisoguanine (2) was isolated from the New Zealand ascidian Pseudodistoma cereum. The structure of 2 was elucidated by the use of standard spectroscopic techniques, including natural abundance 1H-15N 2D NMR.     

Renierone,an antimicrobial metabolite from a marine sponge

The major antibacterial metabolite in the sponge $\text{Reniera}$ sp. was shown to be an isoquinoline quinone, renierone ($\text{1}$). The structure of renierone ($\text{1}$) was defined by X-ray crystallography.     

Homophymine A, an anti-HIV cyclodepsipeptide from the sponge Homophymia sp

A new anti-HIV cyclodepsipeptide, homophymine A, was isolated from a New Caledonian collection of the marine sponge Homophymia sp. The structure of homophymine A was determined by interpretation of spectroscopic data, acid hydrolysis, and LC-MS analysis. Homophymine A contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6-trimethyloctanoic acid moiety. Along with four D-, two L-, and one N-methyl amino acids, it also contains four unusual amino acid residues: (2S,3S,4R)-3,4-diMe-Gln, (2R,3R,4S)-4-amino-2,3-dihydroxy-1,7-heptandioic acid, L-ThrOMe, and (2R,3R,4R)-2-amino-3-hydroxy-4,5-dimethylhexanoic acid. In a cell-based XTT assay, homophymine A exhibited cytoprotective activity against HIV-1 infection with a IC50 of 75 nM.     

Nagahamide A,an antibacterial depsipeptide from the marine sponge Theonella swinhoei

[structure: see text] An antibacterial depsipeptide, nagahamide A (1), has been isolated from the marine sponge Theonella swinhoei. Its structure was determined on the basis of spectral and chemical methods. Absolute configuration of amino acid residues was determined by Marfey's analysis, and relative stereochemistry of the polyketide moiety was assigned by comparison of NMR data with those of a model compound.     

Caminoside A,an antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia

Extracts of the marine sponge Caminus sphaeroconia showed potent activity in a screen for bacterial type III secretion inhibitors. Bioassay guided fractionation of the extract led to the isolation of the novel antimicrobial glycolipid caminoside A (1). The structure of caminoside A was elucidated by analysis of spectroscopic data and chemical degradation.[structure: see text]     

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.     

Amphimedonoic acid and psammaplysene E,novel brominated alkaloids from Amphimedon sp.

Examination of the CH₂Cl₂-MeOH (1:1) extract from the Madagascan sponge Amphimedon sp. highlighted two new brominated alkaloids, amphimedonoic acid (1) and psammaplysene E (2), along with the known 3,5-dibromo-4-methoxybenzoic acid (3). Their structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS data.     

Spirastrellolide A,an antimitotic macrolide isolated from the Caribbean marine sponge Spirastrella coccinea

Sprirastrellolide A, a novel antimitotic macrolide, has been isolated from the Caribbean marine sponge Spirastrella coccinea. It has a 47-carbon linear polyketide backbone incorporated into a highly functionalized 38-membered lactone containing a tetrahydropyran and two spiro bispyran substructures embedded in the macrocycle and a side chain terminating in a carboxylic acid. Sprirastrellolide A's structure was elucidated by detailed spectroscopic analysis of its methyl ester 2. Spirastrellolide A methyl ester 2 shows potent activity in a cell-based assay that detects mitotic arrest, but it does not affect tubulin polymerization in vitro. It has the unusual biological property of being able to accelerate the entry of cells into mitosis from other cell-cycle stages, before it arrests them in mitosis.     

Acanthellin-1, an unique isonitrile sesquiterpene from the sponge Acanthella acuta

A number of unique isonitrile sesquiterpenes have been isolated from the sponge Acanthella acuta. One of them acanthellin-1, with antimicrobial activity, is shown to be 1 with a 4-epi-eudesmane skeleton.     

Asteropterin, an inhibitor of cathepsin B, from the marine sponge Asteropus simplex

A new pteridine derivative, asteropterin (1), was isolated as a cathepsin B inhibitor from the marine sponge Asteropus simplex. The structure of asteropterin (1) was elucidated by the analysis of spectral data.     

Sokodosides, steroid glycosides with an isopropyl side chain, from the marine sponge Erylus placenta

Two novel steroid glycosides, sokodosides A and B (1 and 2, respectively), were isolated from the marine sponge Erylus placenta as growth-inhibitory principles against several strains of yeast and a cancer cell line. Sokodosides possess the novel carbon skeleton as characterized by the presence of a combination of isopropyl side chain and the 4,4-dimethyl steroid nucleus. Sokodoside B has another unique characteristic in the presence of delta(8,14,16) unsaturation. The structures of sokodosides were determined by analysis of spectral data and chemical degradation. The absolute stereochemistry of sokodoside A (1) was determined by the application of the modified Mosher analysis to the aglycon obtained by acid hydrolysis, whereas the absolute stereochemistry of the monosaccharide units in 1 and 2 was determined by chiral GC analyses of the acid hydrolysates.     

Total synthesis of ageladine A, an angiogenesis inhibitor from the marine sponge Agelas nakamurai

[reaction: see text] A 12-step total synthesis of the tricyclic heteroaromatic marine metabolite ageladine A has been achieved using a 6pi-azaelectrocyclization and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloropyridine as key steps.     

Axinelloside A, an unprecedented highly sulfated lipopolysaccharide inhibiting telomerase, from the marine sponge, Axinella infundibula

Axinelloside A was isolated from the lipophilic extract of the Japanese marine sponge Axinella infundibula as a strong human telomerase inhibitor (IC(50) 2.0 microg/mL). It has the molecular weight of 4780.4 as the monoisotopic mass of the 19 sodium salt. The chemical structure was elucidated mainly by spectroscopic methods (2D NMR and MS). Axinelloside A consists of twelve sugars, e.g., a scyllo-inositol, a D-arabinose, 5 D-galactoses, and 5 L-fucoses, together with an (R)-3-hydroxy-octadecanoic acid, 3 (E)-2-hexadecenoic acids, and 19 sulfates.     

Trachycladindoles A-G: cytotoxic heterocycles from an Australian marine sponge, Trachycladus laevispirulifer

A southern Australian marine sponge, Trachycladus laevispirulifer, yielded the cytotoxic agents trachycladindoles A-G (1-7) as a selection of novel indole-2-carboxylic acids bearing a 2-amino-4,5-dihydroimidazole moiety. The trachycladindoles displayed promising selective cytotoxicity against a panel of human cancer cell lines and their structures were assigned on the basis of detailed spectroscopic analysis. Preliminary structure activity relationship (SAR) investigations by co-metabolite defined structural features key to the trachycladindole pharmacophore, highlighting an unusual bioactive molecular motif deserving of future investigation.