Optimizing extraction conditions and isolation of bound phenolic compounds from corn silk (Stigma maydis) and their antioxidant effects.

During the processing of maize, Stigma maydis, also known as corn silk, is normally discarded as waste. Phytochemical research was carried out on the S. maydis to use it as a valuable source of bioactive components. This research aimed to maximize the recovery of free and bound phenolic compounds from corn silk under optimal experimental conditions. Response surface design was operated to optimize the alkaline hydrolysis extraction of bound phytochemicals from corn silk based on total phenolic content and DPPH radical scavenging activity. The optimum conditions (i.e., NaOH concentration 2 M, digestion time 135 min, digestion temperature of 37.5°C, the solid-to-solvent ratio of 1:17.5, and acetone) were obtained. The optimum parameters were used to extract the corn silk. The structures of two compounds isolated from ethyl acetate extracts were then identified as friedelin (1) and (E)-4-(4-hydroxy-3-methoxyphenyl) but-3-en-2-one (2). The DPPH, H2 O2 , and ABTS % inhibition of the compounds is as follows: compound (1) 74.81%, 76.8%, 70.33% and compound (2) 70.37%, 56.70% and 57.46%, respectively. The current study has opened previously unexplored perspectives of the composition of bound compounds in corn silk and established the foundations for more effective processing and utilization of corn waste. PRACTICAL APPLICATION: Bound phenolic compounds from corn silk under optimal experimental conditions were obtained. Corn silk can be utilized as a type of medicinal herb as well as a source of inexpensive natural antioxidants.

Extraction, isolation, characterization and antimicrobial activities of non-extractable polyphenols from pomegranate peel.

Non-extractable polyphenols (NEPPs) in pomegranate peel were released by acid hydrolysis followed by extraction using ethyl acetate (EtOAc). Ten NEPPs were identified in the hydrolysate using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Six compounds were then isolated from the EtOAc extracts whose structures were identified as ß-sitosterol-3-O-glycoside (1), ß-sitosterol (2), ursolic acid (3), corosolic acid (4), asiatic acid (5) and arjunolic acid (6) using a wide range of spectroscopic analyses. Compounds 4-6 were isolated for the first time from pomegranate peel. Antimicrobial experiments revealed that compound 3 and 5 showed significant antimicrobial activity against a range of pathogens, particularly compound 5 which exhibited selective inhibitive activity towards Staphylococcus aureus with a minimum inhibitory concentration (MIC) of 16 µg/ml. The present study has provided new insights into the composition of bound chemicals in pomegranate peel and laid a foundation for improving its further processing and utilization.

Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran.

The bound phenolic compounds in rice bran were released and extracted with ethyl acetate based on alkaline digestion. An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside (8), together with nine known compounds, cycloeucalenol cis-ferulate (1), cycloeucalenol trans-ferulate (2), trans-ferulic acid (3), trans-ferulic acid methyl ester (4), cis-ferulic acid (5), cis-ferulic acid methyl ester (6), methyl caffeate (7), vanillic aldehyde (9) and para-hydroxy benzaldehyde (10). The structures of these compounds were determined using a combination of spectroscopic methods and chemical analysis. Among the compounds isolated, compound 3, 5 and 7 exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6. Compound 1 and 2 showed potent DPPH and ABTS(+) radical scavenging activities, compound 8 displayed moderate antioxidant activity against ABTS(+) radical, whereas compound 9 and 10 showed weak antioxidant activity.

New phenolic compounds from Coreopsis tinctoria Nutt. and their antioxidant and angiotensin i-converting enzyme inhibitory activities.

Three new phenolic compounds, coretinphenol (1), coretincone (2), and coretinphencone (3), were isolated from the buds of Coreopsis tinctoria Nutt., together with nine known compounds, including butein (4), okanin (5), isoliquiritigenin (6), maritimetin (7), taxifolin (8), isookanin (9), marein (10), sachalinoside B (11), and 2-phenylethyl-ß-d-glucoside (12). The chemical structures of these compounds were elucidated by extensive spectroscopic analysis and on the basis of their chemical reactivity. This work represents the first recorded example of the isolation of compounds 1­3, 6, 7, 9, 11, and 12 from C. tinctoria. Compounds 5­9 showed strong diphenyl(2,4,6-trinitrophenyl)iminoazanium (DPPH) radical-scavenging activity, with IC50 values of 3.35 ± 0.45, 9.6 ± 2.32, 4.12 ± 0.21, 6.2 ± 0.43, and 7.9 ± 0.53 µM, respectively. Compounds 2 and 8 exhibited angiotensin I-converting enzyme inhibitory activity, with IC50 values of 228 ± 4.47 and 145.67 ± 3.45 µM, respectively. The activities of phenolic compounds isolated from C. tinctoria support the medicinal use of this plant in the prevention of cardiovascular diseases.

Two new noroleanane-type triterpene saponins from the methanol extract of Salicornia herbacea.

Two new noroleanane-type triterpene saponins, Salbige A (1) and Salbige B (2), have been isolated from the aerial parts of Salicornia herbacea together with five other known compounds, including echinocystic acid (3), gypsogenin (4), pheophorbide a (5), (13(2)S)-hydroxy-pheophorbide a (6) and (13(2)S)-hydro-pheophorbide-lactone a (7). The chemical structures of these compounds were elucidated by extensive spectroscopic analysis and on the basis of their chemical reactivity. This work represents the first recorded example of the isolation of these compounds from S. herbacea. Compounds 1 and 2 exhibited potent antiproliferative activities and high levels of selectivity towards A549 cancer cells, with IC50 values of 52.35 and 79.39 µM, respectively, whereas compound 5 showed high levels of inhibitory activity against A549 and HepG2 cancer cells with IC50 values of 6.15 and 17.56 µM, respectively. None of these compounds exhibited antioxidant activities except for compound 7, which showed weak antioxidant activity.

Cytotoxicity and apoptotic effects of tea polyphenol-loaded chitosan nanoparticles on human hepatoma HepG2 cells.

Tea polyphenols have strong antioxidant and antitumor activities. However, these health benefits are limited due to their poor in vivo stability and low bioavailability. Chitosan nanoparticles as delivery systems may provide an alternative approach for enhancing bioavailability of poorly absorbed drugs. In this study, tea polyphenol-loaded chitosan nanoparticles have been prepared using two different chitosan biomaterials, and their antitumor effects were evaluated in HepG2 cells, including cell cytotoxicity comparison, cell morphology analysis, cell apoptosis and cell cycle detection. The results indicated that the tea polyphenol-loaded chitosan nanoparticles showed a branch shape and heterogeneous distribution in prepared suspension. MTT assay suggested that tea polyphenol-loaded chitosan nanoparticles could inhibit the proliferation of HepG2 cells, and the cytotoxicity rates were increased gradually and appeared an obvious dose-dependent relationship. Transmission electron microscope images showed that the HepG2 cells treated with tea polyphenol-loaded chitosan nanoparticles exhibited some typical apoptotic features, such as microvilli disappearance, margination of nuclear chromatin, intracytoplasmic vacuoles and the mitochondrial swelling. In addition, the tea polyphenol-loaded chitosan nanoparticles had relatively weak inhibitory effects on HepG2 cancer cells compared with tea polyphenols. Tea polyphenols not only induced cancer cell apoptosis, but also promoted their necrosis. However, tea polyphenol-loaded chitosan nanoparticles exhibited their antitumor effects mainly through inducing cell apoptosis. Our results revealed that the inhibition effects of tea polyphenol-loaded chitosan nanoparticles on tumor cells probably depended on their controlled drug release and effective cell delivery. The chitosan nanoparticles themselves as the delivery carrier showed limited antitumor effects compared with their encapsulated drugs.

Concentrations and health risks of lead, cadmium, arsenic, and mercury in rice and edible mushrooms in China.

In this study, four common heavy metals, lead (Pb), cadmium (Cd), arsenic (As) and mercury (Hg) in rice and edible mushrooms of China were studied to evaluate contamination level and edible safety. Ninety two (92) rice samples were collected from the main rice growing regions in China, and 38 fresh and 21 dry edible mushroom samples were collected from typical markets in Nanjing City. The analyzed metal concentrations were significantly different between rice and edible mushroom samples (p<0.05). The results showed that Pb, Cd and As contents in 4.3%, 3.3% and 2.2% rice samples respectively, were above maximum allowable concentration (MAC). In fresh edible mushroom, Pb and Hg contents in 2.6% samples were above MAC, respectively. However, only Hg content in 4.8% dry edible mushroom samples was above its MAC. Therefore, more than 95% rice and edible mushroom samples in our test had high edible safety.

New rubrolides from the marine-derived fungus Aspergillus terreus OUCMDZ-1925.

Two new rubrolides, rubrolides R (1) and S (2), were isolated from the fermentation broth of the marine-derived fungus Aspergillus terreus OUCMDZ-1925. Their structures were elucidated on the basis of spectroscopic analysis and X-ray single crystal diffraction. Compound 1 showed comparable or superior antioxidation against 2,2'-azino-di(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radicals to those of trolox and ascorbic acid with an IC50 value of 1.33 mM. Compound 2 showed comparable or superior anti-influenza A (H1N1) virus activity to that of ribavirin with an IC50 value of 87.1 µM. Both compounds 1 and 2 showed weak cytotoxicity against the K562 cell line with IC50 values of 12.8 and 10.9 µM, respectively.

Pentadecyl ferulate, a potent antioxidant and antiproliferative agent from the halophyte Salicornia herbacea.

An investigation of the chemical constituents of Salicornia herbacea has led to the isolation of one new natural product, pentadecyl ferulate (6), together with 11 known compounds, including phytol (1), stearolic acid (2), γ-linolenic acid (3), (3Z,6Z,9Z)-tricosa-3,6,9-triene (4), linoleic acid (5), stigmasterol (7), ergosterol (8), dioctyl phthalate (9), dibutyl phthalate (10), vanillic aldehyde (11), and scopoletin (12). The chemical structures of these materials were elucidated mainly by spectroscopic analysis. This work represents the first recorded example of the isolation of compounds 1, 2, 3, 4, 9, 10, and 11 from S. herbacea. The antioxidant experiments revealed that compound 6 possessed strong hydroxy radical and superoxide anion scavenging activities and was the principle antioxidant ingredient in the ethyl acetate extract. The antiproliferative results exhibited that compound 1 selectively inhibited HepG2 cells, whereas compounds 3 and 6 showed potent antiproliferative activities against HepG2 and A549 cells.

Synthesis, characterization and cytotoxicity studies of chitosan-coated tea polyphenols nanoparticles.

Chitosan nanoparticles (CS-NPs) were prepared by ionic gelation method using carboxymethyl chitosan and chitosan hydrochloride as carriers of tea polyphenols. The characteristics of chitosan-coated tea polyphenols nanoparticles (CS-TP NPs) were determined by using transmission electron microscopy (TEM) and FT-IR spectroscopy. It was found that the synthesized CS-TP NPs were non-spherical in shape with an average size of 407±50nm. Meanwhile, the drug content and encapsulation rate of the nanoparticles was 8-16% and 44-83%, respectively. These CS-TP NPs also demonstrated sustained release of tea polyphenols in PBS. The antitumor of CS-TP NPs towards HepG2 cancer cells was investigated. The result showed that CS-TP NPs retained significant antitumor activities.

Size effect of se-enriched green tea particles on in vitro antioxidant and antitumor activities.

The antioxidant and antitumor activities (in vitro) of superfine regular and Se-enriched green tea particles with different sizes (3.52 microm and 220 nm) were investigated in this paper. The vitamin C and tea polyphenol contents of green tea in different sizes were significantly different, and amino acid and chlorophyll just changed a little. The antioxidant activity of green tea particles was evaluated by DPPH radical scavenging and linoleic acid peroxidation inhibition methods, and the antitumor activity was evaluated by antiproliferation assay on HepG2, A549, and MGC803 cells. The results indicated that enrichment of selenium endowed green tea with higher antioxidant activity and antitumor activity on HepG2 and A549 cells but not on MGC803 cells. The DPPH radical scavenging rates of regular and Se-enriched green tea of 220 nm (67.87% and 69.49%, respectively) were significantly greater than that of 3.52 microm, but the inhibition of linoleic acid peroxidation for green tea of 220 nm was lower. The inhibitory rates of green tea of 220 nm on HepG2, A549, and MGC803 cells achieved 77.35%, 80.76%, and 87.54% for regular green tea, and 82.51%, 88.09%, and 74.48% for Se-enriched green tea at the dose of 100 microg mL (-1), values that were all significantly higher compared to that of 3.52 microm.

Effect of foliar application of zinc, selenium, and iron fertilizers on nutrients concentration and yield of rice grain in China.

Zn, Se, and Fe levels in 65 Chinese rice samples were investigated, and the results indicated that these micronutrients contents of rice products from different location varied considerably. The mean contents of Zn, Se and Fe in these rice samples were 21.5+/-1.8, 0.020+/-0.012, and 12.4+/-4.3 mg kg(-1), respectively, which were too low to meet the micronutrient demands for the population feeding on the rice as staple. A field orthogonal experiment L9 (3(4)) was conducted on rice cultivar Wuyunjing 7, to evaluate the effect of Zn, Se, and Fe foliar fertilization on the concentration of these micronutrients, yield, and protein and ash content of rice grain. The results indicated that Zn and Se were the main variables influencing the Zn, Se, and Fe content of rice, and the optimal combination of fertilization for enhancing these micronutrients was 0.90 kg ha(-1) Zn, 0.015 kg ha(-1) Se, and 0.90 kg ha(-1) Fe. Under the optimal application condition, Zn, Se, and Fe content of rice could be significantly increased by 36.7%, 194.1%, and 37.1%, respectively, compared with the control, without affecting grain yield and protein and ash content of rice products. Moreover, in the confirmation experiment on rice cultivar Ninggeng 1, the optimal fertilization could increase the Zn, Se, and Fe content of rice up to 17.4, 0.123, and 14.2 mg kg(-1), respectively.

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.