Synthesis of Imidazole-Based Molecules under Ultrasonic Irradiation Approaches.

Imidazole-based compounds are a series of heterocyclic compounds that exhibit a wide range of biological and pharmaceutical activities. However, those extant syntheses using conventional protocols can be time-costly, require harsh conditions, and result in low yields. As a novel and green technique, sonochemistry has emerged as a promising method for organic synthesis with several advantages over conventional methods, including enhancing reaction rates, improving yields, and reducing the use of hazardous solvents. Contemporarily, a growing body of ultrasound-assisted reactions have been applied in the preparation of imidazole derivatives, which demonstrated greater benefits and provided a new strategy. Herein, we introduce the brief history of sonochemistry and focus on the discussion of the multifarious approaches for the synthesis of imidazole-based compounds under ultrasonic irradiation and its advantages in comparison with conventional protocols, including typical name-reactions and various sorts of catalysts in those reactions.

Transcriptome analysis of maize reveals potential key genes involved in the response to belowground herbivore Holotrichia parallela larvae feeding.

The larvae of Holotrichia parallela, a destructive belowground herbivore, causes tremendous damages to maize plants. However, little is known if there are any defense mechanisms in maize roots to defend themselves against this herbivore. In the current research, we carried out RNA-sequencing to investigate the changes in gene transcription level in maize roots after H. parallela larvae infestation. A total of 644 up-regulated genes and 474 down-regulated genes was found. In addition, Gene ontology (GO) annotation analysis and Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway analysis were performed. Weighted gene co-expression network analysis (WGCNA) indicated that peroxidase genes may be the hub genes that regulate maize defenses to H. parallela larvae attack. We also found 105 transcription factors, 44 hormone-related genes, and 62 secondary metabolism-related genes within differentially expressed genes (DEGs). Furthermore, the expression profiles of 12 DEGs from the transcriptome analysis were confirmed by quantitative real-time PCR experiments. This transcriptome analysis provides insights into the molecular mechanisms of the underground defense in maize roots to H. parallela larvae attack and will help to select target genes of maize for defense against belowground herbivory.

Identification and characterization of microRNAs expressed in antennae of Holotrichia parallela Motschulsky and their possible roles in olfactory regulation.

MicroRNAs (miRNAs) are small noncoding RNAs that play posttranscriptional, regulatory roles in various biological processes. However, there has been limited investigation into the potential function of miRNAs in olfaction. The coleopteran Holotrichia parallela is an economically important pest, and miRNAs have been identified in only one coleopteran (Tribolium castaneum). Therefore, this study was conducted to identify miRNAs expressed in the antennae of H. parallela and obtain insights into their possible roles in olfaction. By combining deep sequencing and miRDeep2 software, a total of 99 miRNAs, including 76 conserved miRNAs and 23 novel miRNAs, were identified from H. parallela antennae. The 76 conserved miRNAs belong to 63 families and the other 23 may be species specific or tissue specific. The identified miRNAs have many conserved features of miRNAs. Evaluation of the conservation of the identified miRNA families across different species revealed that most of the families are insect specific. The prediction and annotation of targets suggested that 13 of the identified miRNAs participate in olfactory regulation. Gender differences in antennal expression of nine of the olfactory-related miRNAs were confirmed by quantitative real-time PCR.

DIFFERENTIAL PROTEOME ANALYSIS OF THE MALE AND FEMALE ANTENNAE FROM Holotrichia parallela.

To understand the olfactory mechanisms of Holotrichia parallela antennae in detecting volatile compounds in the environment, protein profiles of H. parallela antennae were analyzed using two-dimensional electrophoresis followed by mass spectrometry and bioinformatics analyses. Approximately 1,100 protein spots in silver staining gel were detected. Quantitative image analysis revealed that in total 47 protein spots showed significant changes in different genders of adult antennae. Thirty-five differentially expressed proteins were identified by Matrix assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF/TOF) tandem mass spectrometer, among which 65.7% are involved in carbohydrate and energy metabolism, antioxidant system, transport, and amino acid/nucleotide metabolism. Some proteins identified here have not been reported previously in insect antennae. Identified male-biased proteins included odorant-binding protein 4, pheromone-binding protein-related protein 2, odorant-binding protein 14, prophenoloxidase-I, acyl-CoA dehydrogenase, aldo-keto reductase-like, carbamoyl phosphate synthetase, etc. whereas some proteins are female biased, such as antennae-rich cytochrome P450, aldehyde dehydrogenase, and putative glutamine synthetase. Alterations in the levels of some proteins were further confirmed by real time polymerase chain reaction (RT-PCR). The proteomic resources displayed here are valuable for the discovery of proteins from H. parallela antennae.

1-nonene plays an important role in the response of maize-aphid-ladybird tritrophic interactions to nitrogen.

Plant volatile organic compounds (VOCs) are the key distress signals involved in tritrophic interactions, by which plants recruit predators to protect themselves from herbivores. However, the effect of nitrogen fertilization on VOCs that mediate tritrophic interactions remains largely unidentified. In this study, a maize (Zea mays)-aphid (Rhopalosiphum padi)-ladybird (Harmonia axyridis) tritrophic interaction model was constructed under high-nitrogen (HN) and low-nitrogen (LN) regimens. H. axyridis had a stronger tendency to be attracted by aphid-infested maize under HN conditions. Then, volatiles were collected and identified from maize leaves on which aphids had fed. All of the HN-induced volatiles (HNIVs) elicited an electroantennogram (EAG) response from H. axyridis. Of these HNIVs, 1-nonene was attractive to H. axyridis under simulated natural volatilization. Furthermore, our regression showed that the release of 1-nonene was positively correlated with H. axyridis visitation rates. Supplying 1-nonene to maize on which aphids had fed under LN enhanced attractiveness to H. axyridis. These results supported the conclusion that 1-nonene was the active compound that mediated the response to nitrogen in the tritrophic interaction. In addition, the 1-nonene synthesis pathway was hypothesized, and we found that the release of 1-nonene might be related to the presence of salicylic acid (SA) and abscisic acid (ABA). This research contributes to the development of novel environmentally friendly strategies to optimize nitrogen fertilizer application and to improve pest control in maize crops.

Glutathione S-Transferase Highly Expressed in Holotrichia parallela Antennae Inactivates the Odorant Unsaturated Aldehyde Volatiles.

Odorant-degrading enzymes in insects play a vital role in maintaining olfactory sensitivity. However, the role and molecular mechanism of glutathione S-transferases (GSTs) in odorant inactivation has been rarely studied. In the present study, 31 GSTs were identified from the antennal transcriptome of Holotrichia parallela. HpGSTd1 possesses the highest transcriptome expression level. Recombinant HpGSTd1 showed degradation activity toward various unsaturated aldehyde volatiles. Furthermore, the metabolite of cinnamaldehyde was identified by high-resolution mass spectrometry (HRMS). The molecular docking analysis and site-directed mutagenesis revealed the key residues of HpGSTd1 in degrading odorants. In addition, the unsaturated aldehyde volatiles elicited the behavioral and electrophysiological responses of H. parallela. Taken together, our findings suggest that HpGSTd1 may play an essential role in inactivating odorants in H. parallela, which provides new insights for identifying molecular targets and exploring effective olfactory regulators for this underground pest.

The herbivore-induced plant volatile tetradecane enhances plant resistance to Holotrichia parallela larvae in maize roots.

BACKGROUND: Many herbivore-induced volatiles have been proven to act as signaling compounds to regulate nearby plant defense responses. However, the precise roles of key volatiles produced by maize roots after Holotrichia parallela larva feeding remain largely unknown. RESULTS: We investigated changes in phytohormones and volatiles in maize roots after H. parallela larval infestation. Marked increases in the phytohormone jasmonic acid (JA) and the volatiles jasmone and tetradecane were induced by herbivores, whereas the salicylic acid content decreased. In addition, pre-exposure to tetradecane markedly increased the levels of the stress hormone JA, its precursors and derivatives, and related gene expression. In addition, pre-exposure altered the production of defensive benzoxazinoid secondary metabolites, resulting in increased plant resistance to H. parallela larvae. Plants pre-exposed to jasmone did not differ from control plants. In addition, bioassays showed that H. parallela larval growth was suppressed by feeding maize roots after pre-exposure to tetradecane. CONCLUSION: These results demonstrate that tetradecane may function as a potent defense induction signal that prepares neighboring plants for incoming attacks. © 2021 Society of Chemical Industry.

Application of the Reuterin System as Food Preservative or Health-Promoting Agent: A Critical Review.

The reuterin system is a complex multi-component antimicrobial system produced by Limosilactobacillus reuteri by metabolizing glycerol. The system mainly includes 3-hydroxypropionaldehyde (3-HPA, reuterin), 3-HPA dimer, 3-HPA hydrate, acrolein and 3-hydroxypropionic acid, and has great potential to be applied in the food and medical industries due to its functional versatility. It has been reported that the reuterin system possesses regulation of intestinal flora and anti-infection, anti-inflammatory and anti-cancer activities. Typically, the reuterin system exerts strong broad-spectrum antimicrobial properties. However, the antimicrobial mechanism of the reuterin system remains unclear, and its toxicity is still controversial. This paper presents an updated review on the biosynthesis, composition, biological production, antimicrobial mechanisms, stability, toxicity and potential applications of the reuterin system. Challenges and opportunities of the use of the reuterin system as a food preservative or health-promoting agent are also discussed. The present work will allow researchers to accelerate their studies toward solving critical challenges obstructing industrial applications of the reuterin system.

Identification of candidate chemosensory receptors in the antennal transcriptome of the large black chafer Holotrichia parallela Motschulsky (Coleoptera: Scarabaeidae).

Olfaction and gustation play critical roles in the daily activities of insects by mediating important behaviors, such as locating host plants, mates and oviposition sites. These behaviors are mediated by a series of chemosensory receptor proteins, including odorant receptors (ORs), gustatory receptors (GRs) and ionotropic receptors (IRs). Holotrichia parallela is a worldwide pest on many crops and particularly on peanuts in China. In the present study, we produced Illumina-based transcriptomes from male and female antennae and ultimately identified 47 candidate ORs, 15 GRs and 27 IRs. Based on phylogenetic analyses, the relatedness with other species and possible functions of chemosensory genes were predicted and analyzed, such as the putative OR co-receptor (HparOR40), IR co-receptors (HparIR1 and HparIR27), carbon dioxide receptors (HparGR5 and HparGR14) and sugar receptors (HparGR8, HparGR11 and HparGR13). The differences in expression between genes and between sexes were analyzed using FPKM values and visualized in heat maps. Furthermore, the qRT-PCR results of 26 candidate genes were assessed to validate the differential expression analyses between sexes and between olfactory and non-olfactory tissues. Thirteen genes were more highly expressed in female than in male antennae, whereas four genes had higher expression in male than in female antennae. Twelve genes were predominantly expressed in the antennae as olfactory organs compared with expression in non-olfactory tissues. Our study was the first to annotate the chemosensory receptors of H. parallela, and it will provide a strong foundation for future work on physiology and ecology at the molecular level.