Modification of the Surface Composition of PTB7-Th: ITIC Blend Using an Additive.

We investigated the effect of adding p-anisaldehyde (AA) solvent to the ink containing poly[[2,60-4,8-di(5-ethylhexylthienyl)benzo[1,2-b:3,3-b]dithiophene][3-fluoro-2[(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl]](PTB7-Th) and 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:20,30-d0]-s-indaceno[1,2-b:5,6-b0]-dithiophene(ITIC) on the morphology of the active layer. The present study focuses on determining the effect of the additive on the compositions at the surface of the PTB7-Th: ITIC composite and its morphology, forming one side of the interface of the blend with the MoOX electrode, and the influence of the structural change on the performance of devices. Studies of device performance show that the addition of the additive AA leads to an improvement in device performance. Upon the addition of AA, the concentration of PTB7-Th at the surface of the bulk heterojunction (BHJ) increases, causing an increase in surface roughness of the surface of the BHJ. This finding contributes to an understanding of the interaction between the donor material and high work function electrode/interface material. The implications for the interface are discussed.

Production of an Anise- and Woodruff-like Aroma by Monokaryotic Strains of Pleurotus sapidus Grown on Citrus Side Streams.

The production of natural flavors by means of microorganisms is of great interest for the food and flavor industry, and by-products of the agro-industry are particularly suitable as substrates. In the present study, Citrus side streams were fermented using monokaryotic strains of the fungus Pleurotus sapidus. Some of the cultures exhibited a pleasant smell, reminiscent of woodruff and anise, as well as herbaceous notes. To evaluate the composition of the overall aroma, liquid/liquid extracts of submerged cultures of a selected monokaryon were prepared, and the volatiles were isolated via solvent-assisted flavor evaporation. Aroma extract dilution analyses revealed p-anisaldehyde (sweetish, anisic- and woodruff-like) with a flavor dilution factor of 218 as a character impact compound. The coconut-like, herbaceous, and sweetish smelling acyloin identified as (2S)-hydroxy-1-(4-methoxyphenyl)-1-propanone also contributed to the overall aroma and was described as an aroma-active substance with an odor threshold in air of 0.2 ng L-1 to 2.4 ng L-1 for the first time. Supplementation of the culture medium with isotopically substituted l-tyrosine elucidated this phenolic amino acid as precursor of p-anisaldehyde as well as of (2S)-hydroxy-1-(4-methoxyphenyl)-1-propanone. Chiral analysis via HPLC revealed an enantiomeric excess of 97% for the isolated product produced by P. sapidus.

Antimicrobial Activity of, and Cellular Pathways Targeted by, p-Anisaldehyde and Epigallocatechin Gallate in the Opportunistic Human Pathogen Pseudomonas aeruginosa.

Plant-derived aldehydes are constituents of essential oils that possess broad-spectrum antimicrobial activity and kill microorganisms without promoting resistance. In our previous study, we incorporated p-anisaldehyde from star anise into a polymer network called proantimicrobial networks via degradable acetals (PANDAs) and used it as a novel drug delivery platform. PANDAs released p-anisaldehyde upon a change in pH and humidity and controlled the growth of the multidrug-resistant pathogen Pseudomonas aeruginosa PAO1. In this study, we identified the cellular pathways targeted by p-anisaldehyde by generating 10,000 transposon mutants of PAO1 and screened them for hypersensitivity to p-anisaldehyde. To improve the antimicrobial efficacy of p-anisaldehyde, we combined it with epigallocatechin gallate (EGCG), a polyphenol from green tea, and demonstrated that it acts synergistically with p-anisaldehyde in killing P. aeruginosa We then used transcriptome sequencing to profile the responses of P. aeruginosa to p-anisaldehyde, EGCG, and their combination. The exposure to p-anisaldehyde altered the expression of genes involved in modification of the cell envelope, membrane transport, drug efflux, energy metabolism, molybdenum cofactor biosynthesis, and the stress response. We also demonstrate that the addition of EGCG reversed many p-anisaldehyde-coping effects and induced oxidative stress. Our results provide insight into the antimicrobial activity of p-anisaldehyde and its interactions with EGCG and may aid in the rational identification of new synergistically acting combinations of plant metabolites. Our study also confirms the utility of the thiol-ene polymer platform for the sustained and effective delivery of hydrophobic and volatile antimicrobial compounds.IMPORTANCE Essential oils (EOs) are plant-derived products that have long been exploited for their antimicrobial activities in medicine, agriculture, and food preservation. EOs represent a promising alternative to conventional antibiotics due to their broad-range antimicrobial activity, low toxicity to human commensal bacteria, and capacity to kill microorganisms without promoting resistance. Despite the progress in the understanding of the biological activity of EOs, our understanding of many aspects of their mode of action remains inconclusive. The overarching aim of this work was to address these gaps by studying the molecular interactions between an antimicrobial plant aldehyde and the opportunistic human pathogen Pseudomonas aeruginosa The results of this study identify the microbial genes and associated pathways involved in the response to antimicrobial phytoaldehydes and provide insights into the molecular mechanisms governing the synergistic effects of individual constituents within essential oils.

Condensation Product of p-anisaldehyde and L-phenylalanine: Fluorescent "on-off" Sensor for Cu2+ and IMPLICATION Logic Gate.

(Z)-2-(4-methoxybenzylideneamino)-3-phenylpropanoic acid (L) synthesized by condensation of p-anisaldehyde and L-phenylalanine acts as selective fluorescent as well as voltammetric sensor for Cu2+ in 2:1 (v/v) CH3OH:H2O. The fluorescence intensity of L (λmax 425 nm) is quenched ca. 65% by Cu2+. Metal ions - Li+, Na+, K+, Al3+, Cu2+, Zn2+, Cd2+, Hg2+, Mn2+, Ni2+ and Pb2+ do not interfere. The binding constant and the detection limits were calculated to be 0.56 × 102 M-1 and 10-6 M respectively. DFT and TDDFT calculations confirmed 2:1 binding stoichiometry between L and Cu2+ obtained from fluorescence data. The interaction between L and Cu2+ is reversible for many cycles with respect to ethylenediamine tetraacetate anion (EDTA2-) which results in IMPLICATION logic gate.

The Natural Product Eugenol Is an Inhibitor of the Ebola Virus In Vitro.

PURPOSE: Since the 2014 Ebola virus (EBOV) outbreak in West Africa there has been considerable effort towards developing drugs to treat Ebola virus disease and yet to date there is no FDA approved treatment. This is important as at the time of writing this manuscript there is an ongoing outbreak in the Democratic Republic of the Congo which has killed over 1000. METHODS: We have evaluated a small number of natural products, some of which had shown antiviral activity against other pathogens. This is exemplified with eugenol, which is found in high concentrations in multiple essential oils, and has shown antiviral activity against feline calicivirus, tomato yellow leaf curl virus, Influenza A virus, Herpes Simplex virus type 1 and 2, and four airborne phages. RESULTS: Four compounds possessed EC50 values less than or equal to 11 µM. Of these, eugenol, had an EC50 of 1.3 µM against EBOV and is present in several plants including clove, cinnamon, basil and bay. Eugenol is much smaller and structurally unlike any compound that has been previously identified as an inhibitor of EBOV, therefore it may provide new mechanistic insights. CONCLUSION: This compound is readily accessible in bulk quantities, is inexpensive, and has a long history of human consumption, which endorses the idea for further assessment as an antiviral therapeutic. This work also suggests that a more exhaustive assessment of natural product libraries against EBOV and other viruses is warranted to improve our ability to identify compounds that are so distinct from FDA approved drugs.

Schiff Base Derived from 4,4'-methylenedianiline and p-anisaldehyde: Colorimetric Sensor for Cu2+, Paper Strip Sensor for Al3+ and Fluorescent Sensor for Pb2.

The condensation product (L) of 4,4'-methylenedianiline and p-anisaldehyde acts as colorimetric sensor for Cu2+ and Pb2+ ions. On interaction with Cu2+, ethanolic solution of L changes its color to brown while it becomes light pink on interaction with Pb2+. Interaction of Al3+ with L coated paper strip emits bright blue fluorescence. Metal ions like Mg2+, Cu2+, Li+, K+, Na+, Mn2+, Al3+, Hg2+, Co2+, Pb2+, Ni2+, Cd2+, Zn2+, Fe3+ do not interfere the paper strip sensor. The fluorescent intensity of L in ethanol is quenched 25 times by Pb2+ ion. The interaction between L and Pb2+ is reversible and the detection limit of Pb2+ is 10-6 M. The binding constant and stoichiometry of binding between L and Pb2+ was calculated to be 104.8 and 1:2. Theoretical calculations show that the binding of the metal ions to L are favorable and the fluorescence of L is due to π → π* transition.

Visualization of Aspalathin in Rooibos (Aspalathus linearis) Plant and Herbal Tea Extracts Using Thin-Layer Chromatography.

Aspalathin, the main polyphenol of rooibos (Aspalathus linearis), is associated with diverse health promoting properties of the tea. During fermentation, aspalathin is oxidized and concentrations are significantly reduced. Standardized methods for quality control of rooibos products do not investigate aspalathin, since current techniques of aspalathin detection require expensive equipment and expertise. Here, we describe a simple and fast thin-layer chromatography (TLC) method that can reproducibly visualize aspalathin in rooibos herbal tea and plant extracts at a limit of detection (LOD) equal to 178.7 ng and a limit of quantification (LOQ) equal to 541.6 ng. Aspalathin is a rare compound, so far only found in A. linearis and its (rare) sister species A. pendula. Therefore, aspalathin could serve as a marker compound for authentication and quality control of rooibos products, and the described TLC method represents a cost-effective approach for high-throughput screening of plant and herbal tea extracts.

Identification of the odorant binding proteins of Western Flower Thrips (Frankliniella occidentalis), characterization and binding analysis of FoccOBP3 with molecular modelling, molecular dynamics simulations and a confirmatory field trial.

Olfactory systems are indispensable for insects as they, including Western Flower Thrips (Frankliniella occidentalis), use olfactory cues for ovipositing and feeding. F. occidentalis use odorant binding proteins (OBPs) to transport semiochemicals to odorant receptors to induce a behavioural response from the sensillum lymph of the insect's antennae. This study identifies four OBPs of F. occidentalis and analyses their expression at three stages of growth: larvae, adult males and adult females. Further, it investigates the presence of conserved motifs and their phylogenetic relationship to other insect species. Moreover, FoccOBP3 was in silico characterized to analyse its structure along with molecular docking and molecular dynamics simulations to understand its binding with semiochemicals of F. occidentalis. Molecular docking revealed the interactions of methyl isonicotinate, p-anisaldehyde and (S)-(-)-verbenone with FoccOBP3. Moreover, molecular dynamics simulations showed bonding stability of these ligands with FoccOBP3, and field trials validated that Lurem TR (commercial product) and p-anisaldehyde had greater attraction as compared to (S)-(-)-verbenone, given the compound's binding with FoccOBP3. The current study helps in understanding the tertiary structure and interaction of FoccOBP3 with lures using computational and field data and will help in the identification of novel lures of insects in the future, given the importance of binding with OBPs.Communicated by Ramaswamy H. Sarma.

Cloning and expression of a novel trans-anethole oxygenase gene from Paraburkholderia sp. MR185.

trans-Anethole oxygenase (TAO) is the key enzyme responsible for the oxidation of trans-anethole to p-anisaldehyde. A strain, Paraburkholderia sp. MR185, was isolated from soil in Yulin star anise-planting regions using trans-anethole as a sole carbon source and a gene which encodes a protein with high similarities to a hypothetical protein of Paraburkholderia sp. MM5384-R2 which shows 61.27% identies with TAO from Pseudomonas putida JYR-1 was cloned and sequenced. The gene, tao, was expressed in E. coli cells and its protein product was purified by affinity chromatography through regenerated amorphous cellulose (RAC). SDS-PAGE analysis indicated a clear band of recombinant protein TAO, and its molecular weight, 38.3 kDa, was consistent with the theoretical value. Its enzyme activity of producing p-anisaldehyde from trans-anethole was detected by DNPH (2,4-dinitrophenylhydrazine) chromogenic reaction and HPLC, and the specific activity of TAO reached 3.93 U/mg protein. Immobilized TAO on RAC was used to catalyze the production of p-anisaldehyde from trans-anethole, and the enzyme retained more than 60% of its initial activity after 10 uses. This is the first report on Paraburkholderia TAO.

Natural Repellents as a Method of Preventing Ant Damage to Microirrigation Systems.

Ants are important because they damage agricultural equipment, including microirrigation systems. The aim of this research was to assess the efficiency of the incorporation of repellents in drip irrigation tubing as a method of protection against ant damage. Unlike previous studies, we tested a series of nontoxic compounds that are repellent to ants. First, we assessed their repellent effects on a local ant species via olfactometer trials. Then, the candidates showing the best results (cinnamon essential oil, p-anisaldehyde and ethyl anthranilate) were incorporated via compounding, injection and extrusion to polyethylene tubing to test their efficiency in the field. Field tests showed high damage levels in the control tubing containing no repellents, presumably caused by up to six different ant species (Cardiocondyla batesii, Plagiolepis pygmaea, P. schmitzii, Solenopsis sp., Tapinoma nigerrimum and Tetramorium semilaeve). In contrast, the pipes containing the three selected compounds remained almost intact, with the treatment including ethyl anthranilate showing no damage at all. These results suggest the strong repellent potential of the selected compounds, even when integrated into plastic, as well as the apparent success of the proposed methodology against the damage caused by ants. The diversity of damage-causing agents that exist in or above the soil strongly encourages further studies to determine the overall efficiency of repellents in protecting irrigation pipes.

Maintenance of Postharvest Quality and Reactive Oxygen Species Homeostasis of Pitaya Fruit by Essential Oil p-Anisaldehyde Treatment.

The performance of p-Anisaldehyde (PAA) for preserving pitaya fruit quality and the underpinning regulatory mechanism were investigated in this study. Results showed that PAA treatment significantly reduced fruit decay, weight loss and loss of firmness, and maintained higher content of total soluble solids, betacyanins, betaxanthins, total phenolics and flavonoids in postharvest pitaya fruits. Compared with control, the increase in hydrogen peroxide (H2O2) content and superoxide anion (O2•-) production was inhibited in fruit treated with PAA. Meanwhile, PAA significantly improved the activity of antioxidant enzymes superoxide dismutase (SOD), peroxidase (POD) and catalase (CAT). Moreover, PAA-treated pitaya fruit maintained higher ascorbic acid (AsA) and reduced-glutathione (GSH) content but lower dehydroascorbate (DHA) and oxidized glutathione (GSSG) content, thus sustaining higher ratio of AsA/DHA and GSH/GSSG. In addition, activities of ascorbate peroxidase (APX), glutathione reductase (GR), monodehydroascorbate reductase (MDHAR) and dehydrogenation ascorbic acid reductase (DHAR), as well as the expression of HpSOD, HpPOD, HpCAT, HpAPX, HpGR, HpDHAR and HpMDHAR, were enhanced after PAA treatment. The findings suggest that postharvest application of PAA may be a reliable method to control postharvest decay and preserve quality of harvested pitaya fruit by enhancing the antioxidant potential of the AsA-GSH cycle and activating an antioxidant defense system to alleviate reactive oxygen species (ROS) accumulation.

A new organic-inorganic compound, ethyl-enedi-ammonium hexa-chlorido-stannate(IV) p-anisaldehyde disolvate.

The asymmetric unit of the title organic-inorganic hybrid complex [systematic name: ethane-1,2-diaminium hexa-chlorido-stannate(IV)-4-meth-oxy-benz-alde-hyde (1/2)], (C2H10N2)[SnCl6]·2C8H8O2, contains one half of an ethyl-enedi-ammonium cation, one half of an [SnCl6]2- anion and one p-anisaldehyde mol-ecule. Both the organic cation and the quasi-regular octa-hedral inorganic anion are located about inversion centres. The organic cations and [SnCl6]2- anions lie in layers parallel to the ac plane with p-anisaldehyde mol-ecules occupying the space between the layers. A network of classical N-H⋯Cl and N-H⋯O hydrogen bonds exists between the ethyl-enedi-ammonium cations and the [SnCl6]2- anions and p-anisaldehyde mol-ecules. These inter-actions, together with non-classical C-H⋯O inter-actions between the ethyl-enedi-ammonium cations and the p-anisaldehyde mol-ecules, serve to hold the structure together. The crystal studied was refined as a two-component twin.

p-Anisaldehyde Exerts Its Antifungal Activity Against Penicillium digitatum and Penicillium italicum by Disrupting the Cell Wall Integrity and Membrane Permeability.

Penicillium digitatum and P. italicum are the two important postharvest pathogens in citrus, causing about 90% of the total loss of citrus fruit during storage and transportation. Natural fungicides such as essential oils have been widely used instead of chemical fungicides for preventing and controlling postharvest diseases. In this research, p-anisaldehyde exhibited a strong inhibitory effect on P. digitatum and P. italicum, with the minimum inhibitory concentration and minimum fungicidal concentration values of both being 2.00 µl/ml. Additionally, p-anisaldehyde visibly inhibited both the green mold and blue mold development of citrus fruits inoculated with P. digitatum and P. italicum. The mycelia morphologies of these pathogens were greatly altered, and the membrane permeability and cell wall integrity of mycelia were severely disrupted under p-anisaldehyde treatment. These results suggest that the antifungal activity of p-anisaldehyde against P. digitatum and P. italicum can be attributed to the disruption of the cell wall integrity.

Physical and antimicrobial properties of anise oil loaded nanoemulsions on the survival of foodborne pathogens.

The purpose of this research was to investigate antimicrobial effects of nano emulsions of anise oil (AO) on the survival of common food borne pathogens, Listeria monocytogenes and Escherichia coli O157:H7. Series of emulsions containing different level of anise oil as potential antimicrobial delivery systems were prepared. Antimicrobial activities of bulk anise oil and its emulsions (coarse and nano) was tested by the minimum inhibitory concentration and time kill assay. Our results showed that bulk anise oil reduced the population of E. coli O157:H7 and L. monocytogenes by 1.48 and 0.47 log cfu/ml respectively after 6 h of contact time. However, under the same condition anise oil nanoemulsion (AO75) reduced E. coli O157:H7 and L. monocytogenes count by 2.51 and 1.64 log cfu/ml, respectively. Physicochemical and microbial analyses indicated that both nano and coarse emulsions of anise oil showed better and long-term physicochemical stability and antimicrobial activity compared to bulk anise oil.