Total synthesis of a marine alkaloid from the tunicate Dendrodoa grossularia

A short synthesis of an indole marine alkaloid (1) from the tunicate Dendrodoa grossularia is described. The key step in the synthesis involves a novel twist on an underutilized oxazole rearrangement, which produces the quaternary stereocenter in the molecule.     

Plakoridine C, a novel piperidine alkaloid from an Okinawan marine sponge Plakortis sp.

A new piperidine alkaloid plakoridine C (1) has been isolated from an Okinawan marine sponge Plakortis species, and the structure was elucidated from spectroscopic data. Plakoridine C (1) is a new alkaloid possessing a piperidine ring connected to a β-keto-γ-lactone through a double bond.     

Nordehydrocyclodercitin, a hexacyclic pyridoacridine alkaloid from the marine ascidian, Aplidium sp

A new hexacyclic pyridoacridine alkaloid, nordehydrocyclodercitin (1), from an ascidian, Aplidium sp., cf. Aplidium cratiferum collected at Arab Reef, Great Barrier Reef, Australia is reported. Nordehydrocyclodercitin is structurally related to stellettamine (2) and cyclodercitin (3), which are sponge metabolites, and cycloshermilamine D (4) which was isolated from the marine tunicate Cystodytes violatinctus. The structure of nordehydrocyclodercitin was determined by interpretation of spectroscopic data, particularly those obtained from HMBC correlations, and by comparison with reported data for known related pyridoacridine alkaloids.     

Lihouidine, a novel spiro polycyclic aromatic alkaloid from the marine sponge Suberea n. sp. (Aplysinellidae, Verongida)

An investigation of a new species of sponge from the genus Suberea collected at Lihou Reef in the Coral Sea afforded lihouidine, an unprecedented cytotoxic spiro nonacyclic polyaromatic alkaloid. The structure of the alkaloid, which was racemic, was determined by a combination of 1D and 2D NMR techniques and single-crystal X-ray structural analysis.     

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.     

Grossularine,a novel indole derivative from the marine tunicate, dendrodoa grossularia

A new marine metabolite, derived from indole and dimethylguanidine, was isolated from the tunicate Dendrodoa grossularia.The proposed structure was based upon spectroscopic evidence.     

Benhamycin, novel alkaloid from terrestrial Streptomyces sp

During our screening for bioactive natural compounds from microorganisms, a novel alkaloid has been isolated from a terrestrial Streptomyces sp. isolate NR12, and named as benhamycin (1). This was along with the known metabolites, uracil, thymine, p-hydroxybenzoic acid, 2'-deoxyuridin, tryptophol, indolyl-3-carboxylic acid, and indolyl-3-carbaldehyde. Chemical structure of the novel compound was determined by detailed analysis of its spectroscopic data (extensive NMR experiments, 1 & 2D, MS spectroscopy, and MS high resolution). Structurally, Benhamycin (1) is a pentacyclic aromatic compound bearing an acridine moiety lactamized with benzene. Biological studies showed that the strain extract was moderately active against Gram-positive, Gram-negative bacteria and fungi.     

Synthesis of aaptamine,a novel marine alkaloid

The novel sponge alkaloid aaptamine has been synthesized for the first time by an efficient route starting from 6-methoxy-7-hydroxy-3,4-dihydrolsoquinoline.     

Ircinamine B, bioactive alkaloid from marine sponge Dactylia sp.

Ircinamine B was isolated from the marine sponge Dactylia sp., which was collected at Cape Sada in Japan. Based on extensive spectral analysis, the structures of the isolated metabolites were established. This novel compound showed moderate activity against the murine leukemia cell line P388 (IC₅₀ 0.28 μg/mL).     

Asymmetric total synthesis of reported structure of eudistomidin B, an indole alkaloid isolated from a marine tunicate

Eudistomidin B, isolated from a marine tunicate, was originally assigned a tetrahydro-β-carboline structure with a 2-p-tolylethanamine residue. Asymmetric total synthesis of the reported structure of natural product, which features an intramolecular diastereoselective Pictet-Spengler cyclization, suggests that the reported structure of the natural product needs to be revised.     

Chartrenoline,a novel alkaloid isolated from a marine Streptomyces chartreusis NA02069

A novel alkaloid featuring a unique tetracyclic ring system was isolated from a marine actinobacterium.     

Hydroperoxysterols from the tunicate Eudistoma sp

Two 27C hydroperoxysterols, 7beta-hydroperoxycholesterol (1) and its stereoisomer 7alpha-hydroperoxycholesterol (2), were isolated from the lipophilic extracts of a Formosan tunicate belonging to the genus Eudistoma. The structures of sterols 1 and 2 were elucidated on the basis of extensive spectral data analyses. Cytotoxicity of sterols 1 and 2 against a limited panel of cancer cell lines is also described. Sterol 1 show weak inhibitory effects on human neutrophil elastase release.     

Prianosin A,a novel antileukemic alkaloid from the okinawan marine sponge Prianos melanos

A novel alkaloid, prianosin A (1), with potent antineoplastic activity has been isolated from the Okinawan marine sponge Prianos melanos. Its absolute stereostructure was determined by single crystal x-ray diffraction analysis.     

Cinachyramine, the novel alkaloid possessing a hydrazone and two aminals from Cinachyrella sp.

The trifluoroacetate salt of cinachyramine (1) was isolated from the Okinawan sponge Cinachyrella sp. This structure was determined by the spectroscopic analysis and the degradation under acidic conditions. Cinachyramine (1) is a novel alkaloid with an unprecedented cage system possessing a hydrazone and two aminals.     

Macrolactin S, a novel macrolactin antibiotic from marine Bacillus sp

A new 24-membered ring lactone, macrolactin S, was isolated from a culture broth of marine Bacillus sp. and its structure was established by various spectral analyses. Macrolactin S is the first macrolactin hydroxylated at C-12. Besides, the known compounds macrolactin A and macrolactin B were also isolated, which were elucidated on the basis of spectral data analyses and literature data comparison. They exhibited antibacterial activity against E. coli and S. aureus.     

Prorocentin-4, a novel linear polyketide from a marine dinoflagellate Prorocentrum sp.

Prorocentin-4, isolated from a cultured marine dinoflagellate Prorocentrum sp. was possessed of two tetrahydrofuran rings, conjugated dienes, four branched methyl groups, and a ketone moiety. The gross structure was elucidated by spectroscopic studies and the relative stereostructure was determined on the basis of spectral data.     

Ishigadine A,a new canthin-6-one alkaloid from an Okinawan marine sponge Hyrtios sp.

A new indole alkaloid with the canthin-6-one skeleton, ishigadine A, has been isolated from an Okinawan marine sponge Hyrtios sp. The structure of ishigadine A was elucidated on the basis of spectroscopic analyses. Ishigadine A is a new canthin-6-one alkaloid possessing a hydroxy group, a 1,3-dimethyl-4-methylthioimidazolium, and a 1-propylguanidine. Ishigadine A is the third canthin-6-one alkaloid from sponges. Ishigadine A might be generated from l-arginine, l-histidine, and l-tryptophan. Ishigadine A exhibited moderate cytotoxicity against L1210 murine leukemia cells.     

Pseudoceratinazole A: a novel bromotyrosine alkaloid from the Australian sponge Pseudoceratina sp.

Mass-directed fractionation based on a Trypanosoma brucei brucei active fraction from the Australian sponge Pseudoceratina sp. led to the isolation of a novel bromotyrosine alkaloid, pseudoceratinazole A (1). Compound 1 is the first dimeric bromotyrosine alkaloid containing an imidazole-bridging moiety.