New Naphthalene Derivatives from the Mangrove Endophytic Fungus Daldinia eschscholzii MCZ-18.

Five new naphthalene derivatives dalesconosides A-D, F (1-4, 6), a known synthetic analogue named dalesconoside E (5), and eighteen known compounds (7-24) were isolated from Daldinia eschscholzii MCZ-18, which is an endophytic fungus obtained from the Chinese mangrove plant Ceriops tagal. Differing from previously reported naphthalenes, compounds 1 and 2 were bearing a rare ribofuranoside substituted at C-1 and the 5-methyltetrahydrofuran-2,3-diol moiety, respectively. Their structures were determined by detailed nuclear magnetic resonance (NMR) and mass spectroscopic (MS) analyses, while the absolute configurations were established by theoretical electronic circular dichroism (ECD) calculation. Compounds 1, 3, 13-17 and 19 showed broad ranges of antimicrobial spectrum against five indicator test microorganisms (Enterococcus faecalis, Methicillin-resistant Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Candida albicans); especially, 1, 16 and 17 were most potent. The variations in structure and attendant biological activities provided fresh insights concerning structure-activity relationships for the naphthalene derivatives.

Dicerandrol C Suppresses Proliferation and Induces Apoptosis of HepG2 and Hela Cancer Cells by Inhibiting Wnt/ß-Catenin Signaling Pathway.

Overwhelming evidence points to an aberrant Wnt/ß-catenin signaling as a critical factor in hepatocellular carcinoma (HCC) and cervical cancer (CC) pathogenesis. Dicerandrol C (DD-9), a dimeric tetrahydroxanthenone isolated from the endophytic fungus Phomopsis asparagi DHS-48 obtained from mangrove plant Rhizophora mangle via chemical epigenetic manipulation of the culture, has demonstrated effective anti-tumor properties, with an obscure action mechanism. The objective of the current study was to explore the efficacy of DD-9 on HepG2 and HeLa cancer cells and its functional mechanism amid the Wnt/ß catenin signaling cascade. Isolation of DD-9 was carried out using various column chromatographic methods, and its structure was elucidated with 1D NMR. The cytotoxicity of DD-9 on HepG2 and HeLa cells was observed with respect to the proliferation, clonality, migration, invasion, apoptosis, cell cycle, and Wnt/ß-catenin signaling cascade. We found that DD-9 treatment significantly reduced tumor cell proliferation in dose- and time-dependent manners in HepG2 and HeLa cells. The subsequent experiments in vitro implied that DD-63 could significantly suppress the tumor clonality, metastases, and induced apoptosis, and that it arrested the cell cycle at the G0/G1 phase of HepG2 and HeLa cells. Dual luciferase assay, Western blot, and immunofluorescence assay showed that DD-9 could dose-dependently attenuate the Wnt/ß-catenin signaling by inhibiting ß-catenin transcriptional activity and abrogating ß-catenin translocated to the nucleus; down-regulating the transcription level of ß-catenin-stimulated Wnt target gene and the expression of related proteins including p-GSK3-ß, ß-catenin, LEF1, Axin1, c-Myc, and CyclinD1; and up-regulating GSK3-ß expression, which indicates that DD-9 stabilized the ß-catenin degradation complex, thereby inducing ß-catenin degradation and inactivation of the Wnt/ß-catenin pathway. The possible interaction between DD-9 and ß-catenin and GSK3-ß protein was further confirmed by molecular docking studies. Collectively, DD-9 may suppress proliferation and induce apoptosis of liver and cervical cancer cells, possibly at least in part via GSK3-ß-mediated crosstalk with the Wnt/ß-catenin signaling axis, providing insights into the mechanism for the potency of DD-9 on hepatocellular and cervical cancer.

A Review on Metabolites from Onchidium Genus: Chemistry and Bioactivity.

The Onchidium genus (Mollusca, Gastropoda, Pulmonata, Systellommatophora, Onchidiidae family) is used as the important economical shellfish, due to the high nutritional value and medicinal value. Research over the previous decades indicated that Onchidium sp. mainly contains polypropionates, depsipeptides, terpenoids and other chemical components. Many biological activities of Onchidium (e. g., cytotoxic activities against tumor cells, anti-viral and anti-bacterial activities) have been reported. This review reports a total of 60 compounds, synthetic work and biological studies on Onchidium genus, covering the literature from 1978 to date, with a view to providing a reference and helping for the in-depth research of this genus.

Study on physicochemical properties and antioxidant activity of polysaccharides from Desmodesmus armatus.

Physicochemical properties and antioxidant activities of Desmodesmus armatus polysaccharides (DAP) were studied. They were extracted by microwave-assisted constant temperature extraction and purification by DEAE-cellulose 52. Four eluents of water (DAP1), 0.25 mol/L NaCl (DAP2), 0.5 mol/L NaCl (DAP3), and 1.0 mol/L NaCl (DAP4) were collected. Four polysaccharides fractions were analyzed, and they were all composed of mannose, rhamnose, glucuronic acid, galacturonic acid, arabinose, and fucose. Gel Permeation Chromatography (GPC) analysis showed that the four polysaccharides fractions have a uniform molecular weight distribution. Scanning electron microscope showed that DAP1 had a dense structure and a smooth but uneven surface, while DAP2, DAP3, and DAP4 were amorphous solids in sheets. Oxidation in vitro experiments showed that DAP2 and DAP3 had scavenging effects on ABTS, DPPH, and hydroxyl radicals. PRACTICAL APPLICATIONS: In the determination of the antioxidant activity, it was found that the antioxidative activity of the polysaccharide of Desmodesmus armatus measured was significantly stronger than the crude polysaccharide of other microalgae. After the polysaccharide was purified, two polysaccharide fractions (DAP2 and DAP3) of Desmodesmus armatus were found to have strong scavenging ability to ABTS, DPPH, and hydroxyl radicals. They can be regarded as a new type of antioxidant, and the differences in the physicochemical properties between the parts can provide a preliminary explanation for the differences in antioxidant activity. But the connection between them needs further analysis. The Desmodesmus armatus used in the experiment is easy to cultivate and easy to obtain, which greatly increases its applicability. This research opens up new possibilities for the development of antioxidants and provides favorable evidence for the use of Desmodesmus armatus in food and feed.

Optimization of microwave-assisted extraction, antioxidant capacity, and characterization of total flavonoids from the leaves of Alpinia oxyphylla Miq.

To optimize the extraction of total flavonoids (TFL) from the leaves of Alpinia oxyphylla Miq. using microwave-assisted method, a orthogonal test was used. The optimal extraction conditions for TFL were determined as follows: ethanol concentration of 50%, solid-liquid ratio of 1:20, temperature of 70 °C, and cycle index of 3. Under these conditions, the extraction yield of TFL was 28.24%. The scavenging rate of TFL against a,a-diphenyl-b-picrylhydrazyl (DPPH), 2,2-azino-bis(3-ethylbenzoth- iazoline-6-sulphonica cid) (ABTS), and superoxide anion radical (O2－·) was screened. The results showed that the bioactivity of extracts appeared to be TFL dose-dependent, while it also presented stronger ferric reducing antioxidant power (FRAP). The contents of chrysin and tectochrysin in TFL were quantitatively analyzed by HPLC.

Effects of Trophic Modes, Carbon Sources, and Salinity on the Cell Growth and Lipid Accumulation of Tropic Ocean Oilgae Strain Desmodesmus sp. WC08.

The effects of trophic modes, carbon sources, and salinity on the growth and lipid accumulation of a marine oilgae Desmodesmus sp. WC08 in different trophic cultures were assayed by single factor experiment based on the blue-green algae medium (BG-11). The results implied that biomass and lipid accumulation culture process were optimized depending on the tophic modes, sorts, and concentration of carbon sources and salinity in the cultivation. There was no significant difference in growth or lipid accumulation with Na2CO3 amendment or NaHCO3 amendment. However, Na2CO3 amendment did enhance the biomass and lipid accumulation to some extent. The highest Desmodesmus sp. WC08 biomass and lipid accumulation was achieved in the growth medium with photoautotrophic cultivation, 0.08 g L-1 Na2CO3 amendment and 15 g L-1 sea salt, respectively.

[Studies on chemical compounds of Chlorella sorokiniana].

Chemical constituents of Chlorella sorokiniana were isolated and purified by repeated column chromatographies, over silicagel and Sephadex LH-20. Their structures were identified on the basis of physicochemical properties and spectroscopic data analysis. Five compounds were obtained from the petroleum ether extract of Chlorella sorokiniana, and their structures were identified as (22E, 24R)-5alpha, 3beta-epidioxiergosta-6, 22-dien-3beta-ol(1),(24S)-ergosta-7-en-3beta-ol(2), loliolide(3), stigmasta-7,22-dien-3beta,5alpha,6alpha-triol(4), and 3beta-hydroxy-5alpha,6alpha-epoxy-7-megastigmen-9-one(5). The main liposoluble fractions from Chlorella sorokiniana maiuly contain fatty acids, alkyl acids and olefine acids. Components 1-5 were isolated from the genus Chlorella for the first time.

[Determination of ethylene glycol bis (2-aminoethyl) ether-N,N,N,N-tetraacetic acid in medicine using high performance liquid chromatography].

A method was developed for the determination of ethylene glycol bis(2-aminoethyl) ether-N,N,N,N-tetraacetic acid (EGTA) by high performance liquid chromatography (HPLC). The content of EGTA can be determined by that of EGTA-Cu through the complexation between EGTA and Cu2+. The chromatographic separation was performed on an Ultimate-AQ C18 analytical column (250 mm x 4.6 mm, 5 µm) using the mobile phase of acetonitrile-ion-pairing reagents (with 0.3% tetrabutyl ammonium hydroxide in mass fraction adjusted to pH 6.50 using acetate)-buffered saline (35 mmol/L sodium acetate of pH 6.50) (20:20:60, v/v/v). The chromatographic conditions were as follows: flow rate, 1.50 mL/min; detection wavelength, 245 nm; injection volume, 100 µL; column temperature, 40 °C. Under the conditions, good linear relationships between the mass concentration and the peak area of EGTA were observed in the range of 0.10-15.00 mg/L (R = 0.9998). The limit of detection (LOD, S/N = 3) and limit of quantitation (LOQ, S/N = 10) were determined as 0.05 mg/L and 0.17 mg/L, respectively. The average recoveries were 98.34%-99.03% with the RSDs of 1.08%-3.33% (n = 9). The results showed that the developed method is sensitive, accurate, reproducible and suitable for the analysis of EGTA in medicine.