Cytoglobosins A-G, Cytochalasans from a Marine-Derived Endophytic Fungus, Chaetomium globosum QEN-14

Financial support from the Ministry of Science and Technology of China (2010CB833802 and 2007AA09Z446) and from the National Science Foundation of China (30910103914) is gratefully acknowledged.

T-Muurolol Sesquiterpenes from the Marine Streptomyces sp M491 and Revision of the Configuration of Previously Reported Amorphanes

Two new sesquiterpenes, 15-hydroxy-T-muurolol (3d) and 11,15-dihydroxy-T-muurolol (3e), along with the plant cadinenes T-muurolol (3f) and 3 alpha-hydroxy-T-muurolol (3g), were isolated from the marine-derived Streptomyces sp. M491. Their absolute configuration was established via NMR spectroscopy and X-ray crystallography of 3-oxo-T-muurolol (3a), which was reisolated from this strain. In addition, the absolute configuration of further sesquiterpenes previously reported from this strain was revised. These products were tested for their cytotoxicity against 37 human tumor cell lines using the MTT method. Only 3d was cytotoxic against a range of human tumor cell lines with a mean IC50 of 6.7 mu g/mL.

Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity

Four new highly brominated and fully substituted mono- and bis-phenols, 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (1), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)ethane (2), 6-(2,3,6-tribromo-4,5-dihydroxybenzyl)-2,5-dibromo-3,4-dihydroxybenzyl methyl ether (3), and 2,3,6-tribromo-4,5-dihydroxybenzyl methyl sulfone (4), were characterized from the marine red alga Symphyocladia latiuscula. In addition, five known bromophenols, bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (5), bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether (6), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (7), 2,3,6-tribromo-4,5-dihydroxymethylbenzene (8), and 2,3,6-tribromo-4,5-dihydroxybenzaldehyde (9), were also isolated and identified. The structures of these compounds were elucidated by spectroscopic methods including 1D and 2D NMR as well as by low- and high-resolution mass spectrometric analysis. Structurally, all of these compounds are highly brominated and fully substituted, and contain one or two 2,3,6-tribromo-4,5-dihydroxyphenyl unit(s) in each of the molecules. In addition, compound 4 possesses a unique sulfone structural feature. Each of the isolated compounds was evaluated for alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity and all were found to be potent, with IC50 values ranging from 8.1 to 24.7 mu M, compared to the known positive control butylated hydroxytoluene (BHT), with an IC50 of 81.8 mu M.

Diterpenes, sesquiterpenes, and a C-15-acetogenin from the marine red alga Laurencia mariannensis

In addition to 10 known compounds (7-16), one new brominated diterpene, 10-hydroxykahukuene B (1), two new sesquiterpenes, 9-deoxyelatol (2) and isodactyloxene A (3), one new brominated C-15-acetogenin, laurenmariallene (4), and two new naturally occurring halogenated sesquiterpenes (5 and 6) that were previously obtained as intemediates in a biomimetic synthetic study of rhodolaureol and rhodolauradiol have been isolated and identified from the organic extract of the marine red alga Laurencia mariannensis. The structures of these compounds were established by spectroscopic methods. The antibacterial and antifungal activities of new compounds 1-4 were evaluated.

Laurendecumallenes A-B and laurendecumenynes A-B, halogenated nonterpenoid C-15-Acetogenins from the marine red alga Laurencia decumbens

Four new halogenated nonterpenoid C-15-acetogenins, 4:7,6:13-bisepoxy-9,10-diol-1,12-dibromopentadeca-1,2-diene (1, laurendecumallene A), 4:7,6:12-bisepoxy-9,10-diol-1,13-dibromopentadeca-1,2-diene (2, laurendecumallene 13), (3Z)-6:10,7:13-bisepoxy-12-bromo-9-hydroperoxylpentadeca-3-en-1-yne (3, laurendecumenyne A), and (3Z)-6:10,9:13-bisepoxy-12-bromo-7-chloropentadeca-3-en-1-yne (4, laurendecumenyne 13), together with one known halogenated C-15-acetogenin elatenyne (5) were isolated and identified from the organic extract of the marine red alga Laurencia decumbens. Their structures and relative stereochemistry were established by means of spectroscopic analysis including UV, IR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and ID and 2D NMR techniques. All these metabolites were submitted for the cytotoxic assay against tumor cell line A549 (human lung adenocarcinoma), but all of them were found inactive (IC50 > 10 mu g/mL).

Halogenated Terpenes and a C-15-Acetogenin from the Marine Red Alga Laurencia saitoi

Seven parguerane diterpenes: 15-bromo-2,7,19-triacetoxyparguer-9(11)-en-16-ol (1), 15-bromo-2,7,16,19-tetraacetoxyparguer-9(11)-ene (2), 15-bromo-2,19-diacetoxyparguer-9(11)-en-7,16-diol (3), 15-bromo-2,16,19-triacetoxyparguer-9(11)-en-7-ol (4), 15bromo-2,16-diacetoxyparguer-9(11)-en-7-ol (5), 15-bromoparguer-9(11)-en-16-ol (6), 15-bromoparguer-7-en-16-ol (7), two polyether triterpenes: thyrsiferol (8) and thyrsiferyl 23-acetate (9), and one C15-acetogenin, neolaurallene (10), were isolated from a sample of marine red alga Laurencia saitoi collected off the coast of Yantai. Their structures were established by detailed NMR spectroscopic analysis and comparison with literature data.

Brominated Selinane Sesquiterpenes from the Marine Brown Alga Dictyopteris divaricata

Two new brominated selinane sesquiterpenes, 1-bromoselin-4(14), 11-diene (1) and 9-bromoselin-4(14), 11-diene (2), one known cadinane sesquiterpene, cadalene (3), and four known selinane sesquiterpenes, alpha-selinene (4), beta-selinene (5), beta-dictyopterol (6), and cyperusol C (7), were isolated from a sample of marine brown alga Dictyopteris divaricata collected off the coast of Yantai (China). Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with literature data.

Chinikomycins A and B: Isolation, structure elucidation, and biological activity of novel antibiotics from a marine Streptomyces sp isolate M045

In our screening of marine Streptomycetes for bioactive principles, two novel antitumor antibiotics designated as chinikomycins A (2a) and B (2b) were isolated together with manumycin A (1), and their structures were elucidated by a detailed interpretation of their spectra. Chinikomycins A (2a) and B (2b) are chlorine-containing aromatized manumycin derivatives of the type 64-pABA-2 with an unusual para orientation of the side chains. They exhibited antitumor activity against different human cancer cell lines, but were inactive in antiviral, antimicrobial, and phytotoxicity tests.

Bromophenols from the marine red alga Polysiphonia urceolata with DPPH radical scavenging activity

Three new (1-3) and three known (4-6) bromophenols were isolated and identified from the marine red alga Polysiphonia urceolata. On the basis of extensive analysis of spectroscopic data, the structures of these compounds were determined to be 7-bromo-9,10-dihydrophenanthrene-2,3,5,6-tetraol (1), 4,7-dibromo-9,10-dihydrophenanthrene-2,3,5,6-tetraol (2), 1,8-dibromo-5,7-dihydrodibenzo[c,e]oxepine-2,3,9,10-tetraol (3), urceolatol (4), 3-,bromo-4,5-dihydroxybenzaidehyde (5), and 3,5-dibromo-4-hydroxybenzaldehyde (6). Each of the isolated compounds was evaluated for alpha,alpha-dipheny1-beta-picrylhydrazyl (DPPH) radical scavenging activity, and all were found to be potent, with IC50 values ranging from 6.1 to 35.8 mu M, compared to the positive control, butylated hydroxytoluene (BHT), with an IC50 of 83.8 mu M.

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 (H-1, C-13, H-1-H-1 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.

A New Cadinane Sesquiterpene from the Marine Brown Alga Dictyopteris divaricata

A sample of the marine brown alga D. divaricata collected off the coast of Yantai (P. R. China) was dried, powdered, and extracted with the mixture of CHCl3 and MeOH (1: 1, v/v). By a combination of silica gel and Sephadex LH-20 column chromatography and preparative TLC, a new cadinane sesquiterpene 1,4-epoxymuurolan-5 beta-ol (1) was isolated from this species. Its structure was established by detailed MS and NMR spectroscopic analysis, as well as comparison with literature data.

Amorphane sesquiterpenes from a marine Streptomyces sp.

The chemical investigation of the crude extract of the marine-derived Streptomyces sp. M491 yielded three new sesquiterpenes, namely, 10 alpha,11-dihydroxyamorph-4-ene (4), 10 alpha,15-dihydroxyamorph-4-en-3-one (6), and 5 alpha,10 alpha,11-trihydroxyamorphan-3-one (7). In addition, the known compounds 10 alpha-hydroxyamorph-4-en-3-one (2), o-hydroxyacetanilide, genistein, prunetin, and indole-3-carbaldehyde and the macrolide antibiotic chalcomycin A were identified. The structures were determined on the basis of spectroscopic analysis, especially 1D and 2D NMR data. This is the first report of these sesquiterpenes from bacteria.

Chemical Constituents of a Marine-Derived Endophytic Fungus Penicillium commune G2M

Cultivation of the endophytic fungus Penicillium commune, which was isolated from the semi-mangrove plant Hibiscus tiliaceus, afforded one new compound 1-O-(2,4-dihydroxy-6-methylbenzoyl)-glycerol (1) along with thirteen known products, including 1-O-acetylglycerol (2), N-acetyltryptophan (3), 3-indolylacetic acid methyl ester (4), 1-(2,4-dihydroxy-3,5-dimethylphenyl)ethanone (5), 2-(2,5-dihydroxyphenyl)acetic acid (6), (4R,5S)-5-hydroxyhexan-4-olide (7), thymidine (8), uracil (9), thymine (10), ergosterol (11), beta-sitosterol (12), beta-daucosterol (13), and ergosta-7,22-dien-3 beta,5 alpha,6 beta-triol (14). The structures of these compounds were established by detailed NMR spectroscopic analysis, as well as by comparison with literature data or with authentic samples.

Particle-attached and free-living bacterial communities in a contrasting marine environment: Victoria Harbor, Hong Kong

Diversity of particle-attached and free-living marine bacteria in Victoria Harbor, Hong Kong, and its adjacent coastal and estuarial environments was investigated using DNA fingerprinting and clone library analysis. Denaturing gradient gel electrophoresis (DGGE) analysis of 16S rRNA genes showed that bacterial communities in three stations of Victoria Harbor were similar, but differed from those in adjacent coastal and estuarine stations. Particle-attached and free-living bacterial community composition differed in the Victoria Harbor area. DNA sequencing of 28 bands from DGGE gel showed Alphaproteobacteria was the most abundant group, followed by the Bacteroidetes, and other Proteobacteria. Bacterial species richness (number of DGGE bands) differed among stations and populations (particle-attached and free-living; bottom and surface). BIOENV analysis indicated that the concentrations of suspended solids were the major contributing parameter for the spatial variation of total bacterial community structure. Samples from representative stations were selected for clone library (548 clones) construction and their phylogenetic distributions were similar to those of sequences from DGGE. Approximately 80% of clones were affiliated to Proteobacteria, Bacteroidetes and Cyanobacteria. The possible influences of dynamic pollution and hydrological conditions in the Victoria Harbor area on the particle-attached and free-living bacterial community structures were discussed.

Particle-attached and free-living bacterial communities in a contrasting marine environment: Victoria Harbor, Hong Kong

Diversity of particle-attached and free-living marine bacteria in Victoria Harbor, Hong Kong, and its adjacent coastal and estuarial environments was investigated using DNA fingerprinting and clone library analysis. Denaturing gradient gel electrophoresis (DGGE) analysis of 16S rRNA genes showed that bacterial communities in three stations of Victoria Harbor were similar, but differed from those in adjacent coastal and estuarine stations. Particle-attached and free-living bacterial community composition differed in the Victoria Harbor area. DNA sequencing of 28 bands from DGGE gel showed Alphaproteobacteria was the most abundant group, followed by the Bacteroidetes, and other Proteobacteria. Bacterial species richness (number of DGGE bands) differed among stations and populations (particle-attached and free-living; bottom and surface). BIOENV analysis indicated that the concentrations of suspended solids were the major contributing parameter for the spatial variation of total bacterial community structure. Samples from representative stations were selected for clone library (548 clones) construction and their phylogenetic distributions were similar to those of sequences from DGGE. Approximately 80% of clones were affiliated to Proteobacteria, Bacteroidetes and Cyanobacteria. The possible influences of dynamic pollution and hydrological conditions in the Victoria Harbor area on the particle-attached and free-living bacterial community structures were discussed.