Antimonate removal by diatomite modified with Fe-Mn oxides: application and mechanism study.

In this study, diatomite coated with Fe-Mn oxides (DFMO) was synthesized through calcination. The adsorption of antimonate (Sb(V)) by DFMO was studied, and environmental factors affecting the adsorption were investigated. The components of DFMO were identified as γ-Fe2O3, γ-MnO2, and SiO2, in the presence of diatomite covered with nanoscale metal oxides. Batch experiments were carried out to evaluate the antimonate adsorption performance in aqueous solution. Results showed that maximum Sb(V) adsorption capacity of DFMO reached 10.7 mg/g at pH 4, corresponding to 22.2 mg/g per unit metal oxides. Antimonate adsorption occurred on heterogenous surface, following the Freundlich and Pseudo-second order model. Overall, antimonate adsorption was favored at acidic condition due to low point of zero charge. However, when treating electroplating wastewater, neutral pH condition exhibited a higher efficiency than acidic pH, because co-existing ions in electroplating wastewater significantly affects antimony adsorption. Further investigation showed that among different potential co-existing ions, fluoride can strongly inhibit the adsorption of antimonate at 5 mg/L under pH 4. Density functional theory (DFT) analysis confirmed that adsorption energy on DFMO follows: HF < F- < Sb(OH)6-, indicating that fluoride is easier to bind with DFMO compared to antimonate, especially under pH 3.5 at which fluoride exists as HF. Moreover, the competitive adsorption of fluoride toward antimonate indicated the necessity of pre-treatment like neutralization and precipitation before adsorption process.

New 19-oxygenated steroid from the South China Sea gorgonian Dichotella gemmacea.

A new 19-oxygenated steroid, 25-acetate-nebrosteroid K (1), and five known steroids (2-6), along with one known 19-hydroxy steroidal glycoside (7) were obtained from the gorgonian Dichotella gemmacea collected from the South China Sea. The structure and relative configuration of 1 were elucidated by using comprehensive spectroscopic data including NOESY spectra. Compound 1 represents the first example of 19-oxygenated steroid with a 19-oic acid methyl ester group isolated from gorgonians. All of the isolated compounds were evaluated for lethal activity to brine shrimp Artemia salina and cytotoxicity against A549 and HL-60 cell lines. Among them, 1 showed strong lethality towards A. salina.

Isolation of the molecular species of monogalactosyldiacylglycerols from brown edible seaweed Sargassum horneri and their inhibitory effects on triglyceride accumulation in 3T3-L1 adipocytes.

The chemical composition of monogalactosyldiacylglycerols (MGDGs) from brown alga Sargassum horneri and their inhibitory effects on lipid accumulation were investigated in this study. A total of 10 molecular species of MGDGs were identified using nuclear magnetic resonance, alkaline hydrolysis, gas chromatography-flame ionization detector, and high-performance liquid chromatography-tandem mass spectrometry methods. Individual molecular species of MGDGs, including (2S)-1-O-myristoyl-2-O-palmitoleoyl-3-O-ß-D-galactopyranosyl-sn-glycerol (1), (2S)-1-O-myristoyl-2-O-linoleyl-3-O-ß-D-galactopyranosyl-sn-glycerol (3), (2S)-1-O-palmitoyl-2-O-linolenoyl-3-O-ß-D-galactopyranosyl-sn-glycerol (5), (2S)-1-O-myristoyl-2-O-oleyl-3-O-ß-D-galactopyranosyl-sn-glycerol (7), (2S)-1-O-palmitoyl-2-O-palmitoleoyl-3-O-ß-D-galactopyranosyl-sn-glycerol (8), (2S)-1-O-palmitoyl-2-O-linoleyl-3-O-ß-D-galactopyranosyl-sn-glycerol (9), and (2S)-1-O-palmitoyl-2-O-oleyl-3-O-ß-D-galactopyranosyl-sn-glycerol (10), were then furnished using semi-preparative high-performance liquid chromatography, and their inhibitory effects on triglyceride (TG) accumulation and free fatty acid (FFA) levels in 3T3-L1 adipocytes were evaluated. Compounds 3 and 9 showed inhibitory effects on TG and FFA accumulation, with TG levels of 1.568 ± 0.2808 and 1.701 ± 0.1460 µmol/L and FFA levels of 0.149 ± 0.0258 and 0.198 ± 0.0229 mequiv/L, respectively, which were more effective than other compounds. The primary structure-activity relationship suggested that linoleyl [18:2(ω-6)] in the sn-2 position played an important role on triglyceride accumulation inhibition.

Bioactive 9,11-secosteroids from Gorgonian Subergorgia suberosa collected from the South China sea.

Five new 9,11-secosteroids 1, 2, and 4-6, and seven known analogs, 3 and 7-12, with the same steroid skeleton, (5αH)-3ß,6α,11-trihydroxy-9,11-secocholest-7-en-9-one, were isolated from the South China Sea gorgonian Subergorgia suberosa. Among them, 2/3 and 4/5 are C(24)-epimeric mixtures, and 6/7 is an (E)/(Z) mixture of (C(24)C(28)). Their structures and relative configurations were elucidated by using comprehensive spectroscopic methods including NOESY spectra. The absolute configuration of the steroidal nucleus was established by the modified Mosher method applied to 10 and on the basis of a common biogenesis for all of these compounds. All isolated compounds, 1-12, and five synthetic acetylated derivatives, 12a-12e, were evaluated for their cytotoxicities in vitro. Compounds 4/5, 11, 12, and 12b-12d showed cytotoxic activities against K562 cell line with the IC50 values ranging from 1.09 to 8.12 µM.

Two new eunicellin-based diterpenoids from the South China Sea gorgonian Muricella sibogae Nutting.

Two new eunicellin-based diterpenoids, sibogins A (1) and B (2), along with one known analogue (3), and four known 9,10-secosteroids (4-7), were isolated from the gorgonian Muricella sibogae Nutting collected from the South China Sea. The structures of the new compounds were elucidated by comprehensive analysis of spectroscopic data, especially by using 2D NMR spectra. The antifouling activity on barnacle Balanus amphitrite and lethality towards brine shrimp Artemia salina of all the isolated compounds were evaluated.

Ochracenoids A and B, guaiazulene-based analogues from gorgonian Anthogorgia ochracea collected from the South China Sea.

Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3-6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configuration of 1 was determined as 3R by the comparison of TDDFT calculated electronic circular dichroism with its experimental spectrum. Compound 1 is a rare guaiazulene-based analogue possessing a unique C16 skeleton. The possible generation process of 1 through an intermolecular one-carbon-transfer reaction was also discussed. Compound 2 was previously described as a presumed intermediate involved in the biogenesis of anthogorgienes A and I. Compound 3 exhibited antiproliferative effects on the embryo development of zebrafish Danio rerio.

Tephrosin-induced autophagic cell death in A549 non-small cell lung cancer cells.

Anticancer effect of tephrosin (1) has been documented; however, the molecular mechanisms underlying the cytotoxicity of tephrosin in cancer cells remain unclear. In the present paper, the proliferation inhibition rate of several cancer cells was tested using the MTT assay; cell cycle, reactive oxygen species (ROS), and mitochondrial membrane potential (MMP) were determined by flow cytometry; poly(ADP-ribose) polymerase (PARP) cleavage and heat shock protein 90 (Hsp90) expression were evaluated by Western blotting; autophagy was examined by confocal microscopy and light chain 3 (LC3) conversion assay. The results showed that exposure of the cells to tephrosin induced significant proliferation inhibition in a dose-dependent manner, especially on A549 with G(2)/M being arrested. Tephrosin was not found to induce cell apoptosis as PARP cleavage was not detected after 24 h treatment, but the formation of acidic vesicular organelle of autophagy character was found, and autophagy was further confirmed by the increase in the ratio of LC3-II to LC3-I. It was observed that tephrosin induced ROS generation and Hsp90 expression inhibition. These results indicate that tephrosin induces A549 cancer cell death via the autophagy pathway, and the roles of ROS generation and Hsp90 expression inhibition in this process need further study in the future.

Three new dioxopiperazine metabolites from a marine-derived fungus Aspergillus fumigatus Fres.

Three new dioxopiperazine metabolites (1-3), together with two known compounds, N-acetyltyramine (4) and cyclo-(Ala-Val) (5), were isolated from a marine-derived fungus Aspergillus fumigatus Fres. Their structures were established by spectroscopic methods. Their cytotoxic activities against the K562 cell line were preliminarily evaluated by the sulphorhodamine B (SRB) method.

GPR12 selections of the metabolites from an endophytic Streptomyces sp. associated with Cistanches deserticola.

An endophytic Streptomyces sp. (AC-2) was isolated from the root of Cistanches deserticola Y.C.Ma.. Chemical investigations of the culture broth of AC-2 afforded fifteen compounds including K1115 A (1), tyrosol (2), phenylethylamine derivatives (3, 4), cyclic dipeptides (5-8), nucleosides and their aglycones (9-13), N-acetyltryptamine (14), and pyrrole-2-carboxylic acid (15). Only tyrosol can promote an increase of intracellular cAMP special on GPR12 transfected cells, such as CHO and HEK293, which means it may be a possible ligand for GPR12.

Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi.

Three new diketopiperazine alkaloids, 6-methoxyspirotryprostatin B (1), 18-oxotryprostatin A (2), and 14-hydroxyterezine D (3), with an oxaspiro[4.4]lactam moiety, 14-norpseurotin A (4), and the 29-nordammarane triterpenoid 6beta,16beta-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (5), as well as 12 known compounds (6- 17), were isolated from the ethyl acetate extract of a marine-derived fungal strain, Aspergillus sydowi PFW1-13. The structures of compounds 1- 5 were elucidated by comprehensive spectroscopic analysis. Compounds 1- 3 exhibit weak cytotoxicity against A-549 cells, with IC 50 values of 8.29, 1.28, and 7.31 microM, respectively. Compound 1 also shows slight cytotoxicity against HL-60 cells, with an IC 50 value of 9.71 microM. Compounds 4 and 5 display significant antimicrobial activities against Escherichia coli, Bacillus subtilis, and Micrococcus lysoleikticus with MICs of 3.74, 14.97, and 7.49 microM and 10.65, 5.33, and 10.65 microM, respectively.

Penicillenols from Penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum.

Six new tetramic acids derivatives, penicillenols A(1), A(2), B(1), B(2), C(1), and C(2) (1-6), together with citrinin, phenol A acid, phenol A, and dihydrocitrinin, were identified from Penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum. Their structures were elucidated on the basis of comprehensive spectral analysis. All the new compounds were evaluated for their cytotoxic effects on four cell lines by the MTT method. Penicillenols A(1) and B(1) showed cytotoxicities against HL-60 cell line with IC(50) values of 0.76 microM and 3.20 microM, respectively.

Citrinin dimers from the halotolerant fungus Penicillium citrinum B-57.

In order to search for structurally novel and bioactive natural compounds from microorganisms, a halotolerant fungal strain, Penicillium citrinum B-57, which mainly produces citrinin derivatives, was isolated from sediments collected from the Jilantai salt field. From the ethyl acetate extract of P. citrinum B-57, two new citrinin dimers, pennicitrinone C ( 1) and penicitrinol B ( 2), and 11 known related compounds were isolated and identified by spectroscopic and chemical methods. These compounds showed antioxidative activity against DPPH radicals with IC 50 values ranging from 0.8 to 59 microM.

Three novel, structurally unique spirocyclic alkaloids from the halotolerant B-17 fungal strain of Aspergillus variecolor.

During our search for novel antitumor lead compounds from microorganisms living under extreme conditions, three novel alkaloids, variecolortides A-C (1-3), were isolated from the mycelia of the halotolerant fungal strain Aspergillus variecolor B-17. The new compounds were found to share an unprecedented 'spiro-anthronopyranoid diketopiperazine' structure, with a stable hemiaminal function, as corroborated by in-depth NMR-spectroscopic and mass-spectrometric analyses, as well as by a single-crystal X-ray analysis of 1. All compounds were shown to exhibit weak cytotoxic and antioxidant activities.

Two new metabolites with cytotoxicities from deep-sea fungus, Aspergillus sydowi YH11-2.

Two new compounds, 2, 3, 5-trimethyl-6-(3-oxobutan-2-yl)-4H-pyran-4-one (1) and (2R)-2, 3- dihydro-7-hydroxy-6, 8-dimethyl-2-[(E)-prop-1-enyl] chromen-4-one (2), together with six known compounds (3-8), were isolated from a deep-sea fungus, identified as Aspergillus sydowi, by a bioassay-guided method. Their structures were elucidated by spectroscopic methods and the cytotoxicities were evaluated by SRB method.

Isoechinulin-type alkaloids, variecolorins A-L, from halotolerant Aspergillus variecolor.

Twelve new compounds, variecolorins A-L ( 1- 12), together with eleven known analogues ( 13- 23) were isolated from the broth of a halotolerant fungus, Aspergillus variecolor. The structures of compounds 1- 12 were determined by chemical and spectroscopic methods. Compounds 1- 11, 13- 15, and 20- 23 exhibited weak radical scavenging activity against DPPH, with IC 50 values from 43 to 103 microM. The new compounds 1- 12 all were essentially nontoxic against the P388, HL-60, BEL-7402, and A-549 cell lines with IC 50 values from 70 to 260 microM.

Isocoumarin Derivatives from the Sea Squirt-derived Fungus Penicillium stoloniferum QY2-10 and the Halotolerant Fungus Penicillium notatum B-52.

Two isocoumarin derivatives, stoloniferol A (1) and B (2), a known 5alpha, 8alpha-epidioxy-23-methyl-(22E, 24R)-ergosta-6, 22-dien-3beta-ol (3), and a known dihydrocitrinone (4) were isolated from the ethyl acetate extract of the sea squirt-derived fungus, Penicillium stoloniferum QY2-10, and a halophilic fungus, Penicillium notatum B-52, respectively. Their structures were elucidated by spectroscopic methods and optical rotation. The stereochemistry of 2 was determined on the basis of different NOE experiments and chemical transformation. Compound 3 showed cytotoxicity against P388 cells, with an IC50 value of 4.07 microM.

Four butenolides are novel cytotoxic compounds isolated from the marine-derived bacterium, Streptoverticillium luteoverticillatum 11014.

Four known butenolides were isolated from the ethyl acetate extracts of the culture broth of the marine-derived bacterium, Streptoverticillium luteoverticillatum, by bioassay-guided fractionation. The structures were identified on the basis of spectral data. The absolute configuration of compound (1) was determined by CD spectrum for the first time. Compounds 1-4 showed in vitro cytotoxicity against the murine lymphoma P388 and human leukemia K562 cell lines. This is the first report on the isolation of butenolides from the marine bacterium, Streptoverticillium luteoverticillatum, and their cytotoxic activities.