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.

Enrichment and hydrogen production by marine anaerobic hydrogen-producing microflora

Acid, alkali, heat-shock, KNO3 and control pretreatment methods applied to anaerobic sludge were evaluated for their ability to selectively enrich the marine hydrogen-producing mixed microflora. Seawater culture medium was used as the substrate. The hydrogen yield of pretreated microflora was higher than that of the un-pretreated control (P < 0.05). Among the pretreatment methods studied, heat-shock pretreatment yielded the greatest hydrogen production, which was 14.6 times that of the control. When the effect of initial pH on hydrogen production of heat-shock pretreated samples was studied, hydrogen was produced over the entire pH range (pH 4-10). The hydrogen yield peaked at initial pH 8 (79 mL/g sucrose) and then steadily decreased as the initial pH increased. Sucrose consumption was high at neutral initial pH. During the process of hydrogen production, pH decreased gradually, which indicated that the acquired microflora consisted of acidogenic bacteria.

Benzodiazepine Alkaloids from Marine-Derived Endophytic Fungus Aspergillus ochraceus

A new fungus-derived benzodiazepine analogue, 2-hydroxycircumdatin C (1), and a compound which has been isolated from a natural resource for the first time, but has been previously synthesized, namely (11aS)-2,3-dihydro-7-methoxy-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (2), along with five structurally related known alkaloids (3-7), were isolated from Aspergillus ochraceus, an endophytic fungus derived from the marine brown alga Sargassum kjellmanianum. Their structures were established on the basis of spectroscopic methods. The absolute configuration of I was determined through CD evidence. Compound 1 displayed significant DPPH radical-scavenging activity with an IC50 value of 9.9 mu M, which is 8.9-fold more potent than that of butylated hydroxytoluene (BHT), a well-known synthetic positive control.

Halogenated Sesquiterpenes from the Marine Red Alga Laurencia saitoi (Rhodomelaceae)

Four new halogenated sesquiterpenes, 10-bromo-3-chloro-2,7-epoxychamigr-9-en-8a-of (1), 2,10 beta-dibromochamigra-2,7-dien-9 alpha-ol (2), (9S)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (3), and (9R)-2-bromo-3-chloro-6,9-epoxybisabola-7(14),10-diene (4), were characterized from the marine red alga Laurencia saitoi. In addition, two known halosesquiterpenes, 2,10-dibromo-3-chlorochamigr-7-en-9 alpha-ol (5) and isolaurenisol (6), were also isolated and identified. Their structures were established on the basis of extensive analysis of spectroscopic data.

A review of advances in research on marine molluscan antimicrobial peptides and their potential application in aquaculture

Antimicrobial peptides (AMPs) are important components of the host innate immune response against microbial invasion. They are usually characterized by their small-size, heat-stability and broad range of antimicrobial activity. This review covers research advances on marine mollusc AMPs, specifically those isolated from mussels, scallops, oysters, venerid clams and abalone, which mainly include MGD, mytilin, myticin, mytimycin, big defensin, and RPD-1. Their structural characteristics, antibacterial activity, and expression pattern as well as peptide distribution and their release following microbial challenge are also discussed. In addition, the prospect of the application of AMPs as food additives or their use in immunostimulation to prevent diseases of aquatic animals, as well as their potential hazards, are also discussed.

Natural Anthraquinone Derivatives from a Marine Mangrove Plant-Derived Endophytic Fungus Eurotium rubrum: Structural Elucidation and DPPH Radical Scavenging Activity

There is considerable interest in the isolation of potent radical scavenging compounds from natural resources to treat diseases involving oxidative stress. In this report, four new fungal metabolites including one new bisdihydroanthracenone derivative (1, eurorubrin), two new seco-anthraquinone derivatives [3, 2-O-methyl-9-dehydroxyeurotinone and 4, 2-O-methyl4-O-(alpha-D-ribofuranosyl)-9-dehydroxyeurotinone], and one new anthraquinone glycoside [6,3-O-(alpha-D-ribofuranosyl)questin], were isolated and identified from Eurotium rubrum, an endophytic fungal strain that was isolated from the inner tissue of the stem of the marine mangrove plant Hibiscus tiliaceus. In addition, three known compounds including asperflavin (2), 2-O-methyleurotinone (5), and questin (7) were also isolated and identified. Their structures were elucidated on the basis of spectroscopic analysis. All of the isolated compounds were evaluated for 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity.

Enrichment of the hydrogen-producing microbial community from marine intertidal sludge by different pretreatment methods

To determine the effects of pretreatment on hydrogen production and the hydrogen-producing microbial community, we treated the sludge from the intertidal zone of a bathing beach in Tianjin with four different pretreatment methods, including acid treatment, heat-shock, base treatment as well as freezing and thawing. The results showed that acid pretreatment significantly promoted the hydrogen production by sludge and provided the highest efficiency of hydrogen production among the four methods. The efficiency of the hydrogen production of the acid-pretreated sludge was 0.86 +/- 0.07 mol H-2/mol glucose (mean +/- S.E.), whereas that of the sludge treated with heat-shock, freezing and thawing, base method and control was 0.41 +/- 0.03 mol H-2/mol glucose, 0.17 +/- 0.01 mol H-2/mol glucose, 0.11 +/- 0.01 mol H-2/mol glucose and 0.20 +/- 0.04 mol H-2/mol glucose, respectively. The result of denaturing gradient gel electrophoresis (DGGE) showed that pretreatment methods altered the composition of the microbial community that accounts for hydrogen production. Acid and heat pretreatments were favorable to enrich the dominant hydrogen-producing bacterium, i.e. Clostridium sp., Enterococcus sp. and Bacillus sp., However, besides hydrogen-producing bacteria, much non-hydrogen-producing Lactobacillus sp. was also found in the sludge pretreated with base, freezing and thawing methods. Therefore, based on our results, we concluded that, among the four pretreatment methods using acid, heat-shock, base or freezing and thawing, acid pretreatment was the most effective method for promoting hydrogen production of microbial community. (C) 2009 Professor T. Nejat Veziroglu. Published by Elsevier Ltd. All rights reserved.

Chemical constituents of marine medicinal mangrove plant Sonneratia caseolaris

Twenty-four compounds including eight steroids (1-8), nine triterpenoids (9-16, 24), three flavonoids (20-22), and four benzenecarboxylic derivatives (17-19, 23) were isolated and identified from stems and twigs of medicinal mangrove plant Sonneratia caseolaris. The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data. Among these metabolites, compounds 1, 4-20 and 22-24 were isolated and identified for the first time from S. caseolaris. In the in vitro cytotoxic assay against SMMC-7721 human hepatoma cells, compound 21 (3',4',5,7-tetrahydroxyflavone) exhibited significant activity with IC50 2.8 mu g/mL, while oleanolic acid (14), 3,3'-di-O-methyl ether ellagic acid (18), and 3,3',4-O-tri-O-methyl ether ellagic acid (19) showed weak activity. None of these compounds displayed significant antibacterial activites.