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PubMed2006

DNA methyl transferase inhibiting halogenated monoterpenes from the Madagascar red marine alga Portieria hornemannii.

Three new halogenated monoterpenes, 2, 3, and 4, along with the known compounds halomon (1) and two analogues, 5 and 6, were isolated from the Madagascar red marine alga Portieria hornemannii. The structures of all three new compounds were determined by NMR spectroscopy in combination with mass spectrometric data analysis. Two of these monoterpenes (1 and 2) were low micromolar inhibitors of DNA methyl transferase-1.

DNA Modification Methylases↗
PubMed2006

Bromophycolides C-I from the Fijian red alga Callophycus serratus.

Bromophycolides C-I (1-7) were isolated from extracts of the Fijian red alga Callophycus serratus and identified by NMR and mass spectral techniques. These novel natural products share a carbon skeleton and biosynthetic origin with previously identified bromophycolides A (8) and B (9), which form a rare group of diterpene-benzoate macrolides. Bromophycolides C-I (1-7) displayed modest antineoplastic activity against a range of human tumor cell lines.

Antineoplastic Agents↗
PubMed2006

Bioactivity profiling using HPLC/microtiter-plate analysis: application to a New Zealand marine alga-derived fungus, Gliocladium sp.

Using HPLC/microtiter-plate-based generation of activity profiles the extract of a marine alga-derived fungus, identified as Gliocladium sp., was shown to contain the known strongly cytotoxic metabolite 4-keto-clonostachydiol (1) and also clonostachydiol (2) as well as gliotide (3), a new cyclodepsipeptide containing several D-amino acids. The absolute configuration of 1 was elucidated by reduction to 2, and two further oxidized derivatives of clonostachydiol (5, 6) were prepared and evaluated for biological activity.

Animals↗
PubMed2005

Sulfur-containing polybromoindoles from the Formosan red alga Laurencia brongniartii.

Five new sulfur-containing polybromoindoles, 2-methylsulfinyl-3-methylthio-4,5,6-tribromoindole (1), 3-methylsulfinyl-2,4,6-tribromoindole (2), 4,6-dibromo-2,3-di(methylsulfinyl)indole (3), 3,3'-bis(2'-methylsulfinyl-2-methylthio-4,6,4',6'-tetrabromo)indole (4), and 3,3-bis(4,6-dibromo-2-methylsulfinyl)indole (5), as well as seven known sulfur-containing polybromoindoles, 3-methylthio-2,4,6-tribromoindole (6), 3-methylthio-2,4,5,6-tetrabromoindole (7), 4,6-dibromo-2,3-di(methylthio)indole (8), 2,3-di(methylthio)-4,5,6-tribromoindole (9), 4,6-dibromo-2-methylsulfinyl-3-(methylthio)indole (10), 4,6-dibromo-2-(methylthio)indole (11), and 3,3-bis(4,6-dibromo-2-methylthio)indole (12), have been isolated from the Formosan red alga Laurencia brongniartii. The structures were elucidated by extensive spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

Antineoplastic Agents↗
PubMed2005

Chromenes from the brown alga Sargassum siliquastrum.

Sargachromanols A-P (1-16), sixteen new meroterpenoids of the chromene class, were isolated from the brown alga Sargassum siliquastrum collected from Jaeju Island, Korea. On the basis of the combined results of spectral and chemical analyses, the structures of the polyprenyl portions of these chromanol-containing compounds were determined to be linear triprenyls (1 and 2) and tetraprenyls (3-11), while others were the corresponding rearranged (12-15) and cyclized (16) tetraprenyls, respectively. The new compounds exhibited significant antioxidant activity in the DPPH assay. Compounds 7 and 15 also showed inhibitory activity toward butylcholine esterase.

Antioxidants↗
PubMed2006

Gracilarioside and gracilamides from the red alga Gracilaria asiatica.

One gracilarioside and two gracilamides with unusual cyclopropane-containing alkyl chains were isolated from the red alga Gracilaria asiatica. Their structures were determined by spectroscopic methods and microscale chemical degradation. To our knowledge, no ceramides with a cyclopropane ring have been reported from marine organisms. These three compounds were mildly cytotoxic to the human A375-S2 melanoma cell line.

Antineoplastic Agents↗
PubMed2006

Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata.

Five minor sesquiterpenes (1-5) with two novel carbon skeletons, together with a minor new oplopane sesquiterpene (6), have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR, and CD, their structures including absolute configurations were assigned as (+)-(1R,5S,6S,9R)-3-acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-3-ene (1), (+)-(1R,3S,4S,5R,6S,9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[4.3.0]nonane (2), (+)-(1R,3R,4R,5R,6S,9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[4.3.0]nonane (3), (+)-(1S,2R,6S,9R)-1-hydroxy-2-(1-hydroxyethyl)-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en-3-one (4), (-)-(5S,6R,9S)-2-acetyl-5-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-1-en-3-one (5), and (-)-(1S,6S,9R)-4-acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en-3-one (6). Biogenetically, the carbon skeletons of 1-6 may be derived from the co-occurring cadinane skeleton by different ring contraction rearrangements. Compounds 1-6 were inactive (IC(50) > 10 mug/mL) against several human cancer cell lines.

Drug Screening Assays, Antitumor↗
PubMed2006

Bisabolanes from the red alga Laurencia scoparia.

Three novel halogenated beta-bisabolene sesquiterpenoids (1-3), together with two know triquinane alcohol sesquiterpenes (6 and 7), were isolated from the red alga Laurencia scoparia and their structures elucidated by spectroscopic methods. Single-crystal X-ray crystallography allowed us to confirm the structure of 1 as well as to determine the absolute configuration of all stereocenters. To the best of our knowledge, the isolation of beta-bisabolenes from the genus Laurencia has no precedent in the literature. Compound 1 showed weak in vitro anthelmintic activity against parasitant stage (L4) Nippostrongilus brasiliensis.

Animals↗
PubMed2006

Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata.

Cultivation of the endophytic fungus Chaetomium globosum, which was isolated from the inner tissue of the marine red alga Polysiphonia urceolata, resulted in the isolation of chaetopyranin (1), a new benzaldehyde secondary metabolite. Ten known compounds were also isolated, including two benzaldehyde congeners, 2-(2',3-epoxy-1',3'-heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (2) and isotetrahydroauroglaucin (3), two anthraquinone derivatives, erythroglaucin (4) and parietin (5), five asperentin derivatives including asperentin (6, also known as cladosporin), 5'-hydroxy-asperentin-8-methylether (7), asperentin-8-methyl ether (8), 4'-hydroxyasperentin (9), and 5'-hydroxyasperentin (10), and the prenylated diketopiperazine congener neoechinulin A (11). The structures of these compounds were determined on the basis of their spectroscopic data analysis (1H, 13C, 1H-1H COSY, HMQC, and HMBC NMR, as well as low- and high-resolution mass experiments). To our knowledge, compound 1 represents the first example of a 2H-benzopyran derivative of marine algal-derived fungi as well as of the fungal genus Chaetomium. Each isolate was tested for its DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging property. Compounds 1-4 were found to have moderate activity. Chaetopyranin (1) also exhibited moderate to weak cytotoxic activity toward several tumor cell lines.

Animals↗
PubMedDate not supplied

Marine biopolymers with cell specificity--III--Agglutinins in the red alga Cystoclonium purpureum: isolation and characterization.

The red alga, Cystoclonium purpurcum, contains agglutinins which selectively agglutinate mouse leukemia cells L5178Y but not L1210. It also agglutinated erythrocytes, lymphocytes, and a marine bacterium. The major component was a glycoprotein having a molecular weight of 12,500 daltons. It contained 5.6% carbohydrates and consisted of two subunits.

Agglutinins↗
PubMedDate not supplied

Plant antimutagenic agents, 7. Structure and antimutagenic properties of cymobarbatol and 4-isocymobarbatol, new cymopols from green alga (Cymopolia barbata).

Two new compounds, cymobarbatol and 4-isocymobarbatol, were isolated from the marine alga Cymopolia barbata. The complete structures and absolute stereochemistries of these compounds were elucidated by a variety of spectroscopic techniques and X-ray crystallography. Both compounds were found to be nontoxic over a broad concentration range to Salmonella typhimurium strains T-98 and T-100. Both compounds exhibited strong inhibition of the mutagenicity of 2-aminoanthracene and ethyl methanesulfonate toward, respectively, the T-98 strain plus a metabolic activator and T-100.

Benzopyrans↗
PubMedDate not supplied

A new polyhalogenated monoterpene from the red alga Plocamium cartilagineum.

From a sample of the red alga Plocamium cartilagineum, four polyhalogenated monoterpenes [1-4] were isolated and characterized with (3R*, 4R*)-1-bromo-7-chloromethyl-3,4-dichloro-3-methyl-1E,5E,7-octatrie ne [1] being a new compound. Also reported are antifungal, antibacterial, and molluscicidal activities, as well as the brine shrimp toxicity of these metabolites.

Antifungal Agents↗
PubMedDate not supplied

Novel pyrroles from the Oregon red alga Gracilariopsis lemaneiformis.

Two new pyrrole natural products have been isolated from the temperate-water red alga, Gracilariopsis lemaneiformis, as diacetate derivatives. The structures of these C- and N-alkylated pyrroles were determined by spectroscopic methods (principally high field nmr and ms) to be N-(2-acetoxy)-propyl-2-(2-acetoxy)-acetopyrrole and N-(2-acetoxy)-ethyl-2-(2-acetoxy)-acetopyrrole.

Magnetic Resonance Spectroscopy↗
PubMedDate not supplied

A cytotoxic and antifungal 1,4-naphthoquinone and related compounds from a New Zealand brown algae, Landsburgia quercifolia.

The bioactivity-directed isolation of deoxylapachol [I] from a New Zealand brown alga, Landsburgia quercifolia, is described. Compound I was active against P-388 leukemia cells (IC50 0.6 microgm/ml) and was also antifungal. 1,4-Dimethoxy-2-(3-methyl-2-butenyl)-naphthalene [3] was the major low polarity component of extracts of this seaweed, which also contained 2,3-dihydro-2,2-bis(3-methyl-2-butenyl)-1,4-naphthalenedione [6] and 2-(3-methyl-2-butenyl)-2,3-epoxy- 1,4-naphthalenedione 4,4-dimethoxy ketal [7]. Compound 7 was converted to the 2,3-epoxide of I, which had biological activities similar to those of I.

Animals↗
PubMed1993

Kahukuenes, new diterpenoids from the marine alga Laurencia majuscula.

Kahukuenes A [4] and B [5], new diterpenoids possessing an unprecedented prenylated chamigrene structure as part of a decalin ring, were isolated from the Hawaiian marine alga Laurencia majuscula. Spectroscopic methods, including extensive 1D and 2D nmr studies, were used to establish the structure and relative stereochemistry of these two secondary metabolites.

Bridged Bicyclo Compounds↗