Screening and Analysis of the Potential Bioactive Components in Rabbit Plasma after Oral Administration of Hot-Water Extracts from Leaves of <em>B</em><em>ambusa </em><em>textilis </em>McClure

Bambusa textilis McClure is a traditional Chinese medicinal plant belonging to the Bambusoideae subfamily and used to treat chronic fever and infectious diseases. To investigate the bioactive compounds absorbed in the rabbit blood after oral administration of hot-water extracts from the leaves of B. textilis McClure, a validated chromatographic fingerprint method was established using LC-Q-TOF-MS. Twenty compounds in bamboo leaves and three potential bioactive compounds in rabbit plasma were detected. Of the twenty detected compounds in vitro, fifteen of which were tentatively identified either by comparing the retention time and mass spectrometry data with that of reference compounds or by reviewing the literature. Three potential bioactive compounds, including (E)-p-coumaric acid, (Z)-p-coumaric acid, and apigenin-8-C-β-D-(2"-O-α-L-rhamnosyl)-gluco-pyranoside, were detected in both the leaves of B. textilis McClure and rabbit plasma. Of the three compounds, apigenin-8-C-β-D-(2"-O-α-L-rhamnosyl)glucopyranoside was identified based on its UV, MS, and NMR spectra. This study provides helpful chemical information for further pharmacology and active mechanism research on B. textilis McClure.     

Metabolic fate of dietary volatile compounds in Pieris brassicae

In this work, the evolution of the qualitative and quantitative profile of the volatile fraction of Pieris brassicae after feeding on Brassica oleracea var. acephala (kale) was monitored through time. HS-SPME/GC-MS was applied to both the host plant and the living insect and its excrements. A total of seventy seven compounds (lipoxygenase pathway by-products, nitrogen compounds, norisoprenoids, sulphur compounds, terpenes, among others) were identified. Thirty eight compounds were identified in insect after 2 h of starvation and forty eight compounds in excrements. Qualitative and quantitative changes were detected along time. Dimethyldisulfide, dimethyltrisulfide, limonene and eugenol were major compounds for all analysed times in both matrices, being limonene an important compound in insect after starvation. The accumulation by P. brassicae of some compounds, such as limonene, was verified, suggesting a mechanism by which the insect can take benefit from bioactive constituents from the diet. Along with accumulation, complete excretion of some compounds, including nitrogen bearing compounds, by-products of glucosinolates was detected. These results reflect one of the strategies used to overcome plant barriers, namely detoxification of toxic compounds. The findings contribute to the knowledge of the metabolization of the volatile compounds in insects and contribute to the body of knowledge of this ecologic system.     

Comparative Study of Volatile Compounds and Expression of Related Genes in Fruit from Two Apple Cultivars during Different Developmental Stages

Aromatic volatile compounds are important contributors to fruit quality that vary among different cultivars. Herein, headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry was used to determine changes in volatile compounds and related gene expression patterns in “Ruixue” and “Fuji” apples (Malus domestica Borkh.) during fruit development and maturation. Volatile compounds detected in the fruit of both cultivars exhibited similar trends across different developmental stages. In the early stages of “Ruixue” fruit development (60 days after full bloom), there were fewer volatile compounds, mainly aldehydes (87.0%). During fruit maturation (180 days after full bloom), the types and amounts of volatile compounds increased, mainly including esters (37.6%), and alkenes (23.2%). The total volatile concentration, the types of major volatile compounds, and their relative content in both cultivars varied across different stages. Gene expression analysis indicated that the upregulation of MdLOX, MdAAT2, and MdADH3 was associated with increased aroma compound content, especially esters, during fruit development in both cultivars. Changes in the expression of MdArAT, MdACPD, MdADH3, MdAAT2, and MdLOX may lead to differences in volatile compounds between apple cultivars.     

Setup of an Ultrasonic-Assisted Extraction to Obtain High Phenolic Recovery in Crataegus monogyna Leaves

Hawthorn leaves are a rich source of phenolic compounds that possess beneficial activities for human health. Ultrasonic-assisted extraction (UAE) is an extraction technique frequently used for the isolation of phenolic compounds in plants. Thus, in this study, a Box–Behnken design was used to optimize UAE conditions such as the percentage of acetone, the extraction time and solvent-to-solid ratio (v/w) in order to obtain the maximum content of total compounds by Folin–Ciocalteu and the maximum in vitro antioxidant activity by DPPH, ABTS and FRAP assays in Crataegus monogyna leaves. The optimum conditions to obtain the highest total phenolic content and antioxidant activities were 50% acetone, 55 min and 1/1000 (w/v). A total of 30 phenolic compounds were identified and quantified in C. monogyna leaf extract obtained at these optimum UAE conditions. HPLC-MS allows the identification and quantification of 19 phenolic compounds and NP-HPLC-FLD analyses showed the presence of 11 proanthocyanidins. According to the results, the most concentrated phenolic compounds in C. monogyna leaf extract obtained at optimum UAE conditions were phenolic acid derivatives such as protocatechuic acid-glucoside, dihydroxy benzoic acid pentoside and chlorogenic acid, flavones such as 2″-O-rhamnosyl-C-hexosyl-apigenin, flavonols such as hyperoside and isoquercetin and proanthocyanidins such as monomer and dimer. As a result, the optimized UAE conditions could be used to obtain an extract of C. monogyna leaves enriched with phenolic compounds.     

The unprecedented C-alkylation and tandem C-/O-alkylation of phenanthrolinium salts with cyclic 1,3-dicarbonyl compounds

N-p-Nitrobenzyl- or N-phenacylphenanthrolinium bromides reacted with a series of cyclic 1,3-dicarbonyl compounds in acetonitrile in the presence of triethylamine as base catalyst to give the unprecedented C-alkylated products and tandem alkylated/intramolecular O-alkylated oxazabicyclic compounds according to the structure of cyclic 1,3-dicarbonyl compounds.     

Aggregation-induced emission compounds as new assisted matrices for laser desorption/ionization time-of-flight mass spectrometry

Here, N,N′-bis(4-hydroxylsalicylidene)-p-phenylenediamine (BSPD-OH), N,N′-bis(4-methoxylsalicylidene)-p-phenylenediamine (BSPD-OMe) and N,N′-bis(salicylidene)-p-phenylenediamine (BSPD), which belong to the same category of aggregation-induced emission (AIE) compounds based on Schiff base reactions, were synthesized and applied as new matrices in the analysis of small molecules by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). This type of AIE compounds can be good MALDI matrices. Conventional organic matrices often produce large amounts of matrix ions, hindering the analysis of low molecular weight (LMW) compounds. However, these AIE compounds generate few matrix ions and less background interference because their presence as aggregates decreases the generation of matrix interference. The sensitivity of the AIE matrix is high because the aggregates can improve the absorption of the applied laser emissions. We can regulate the ionization efficiency of the AIE matrix by changing its aggregation state. During this study, BSPD-OH exhibited better ionization efficiency than the other two AIE matrices because it has more phenolic hydroxyl groups. BSPD-OH was successfully applied to the analysis of various LMW compounds including amino acids, organic amine compounds, isoquinoline compounds and fluoroquinolones compounds. This material also can be employed during the qualitative and quantitative analysis of LMW metabolites in human urine without requiring complicated separation processes.     

Synthesis,characterization and biological activities of some azo derivatives of aminothiadiazole derived from nicotinic and isonicotinic acids

In this study we synthesized the new compounds containing bis-1,3,4-thiadiazole 3(A–D)_n from many reaction steps (cyclization, diazotization and etherification respectively). The compounds have been characterized by melting point, FT-IR and ¹H NMR data. All the synthesized compounds have been evaluated in vitro for their antimicrobial activities against several microbes like: Escherichia coli, Klebsiellia pneumonia, Pseudomonas aeruginosa, Serratia marscens and Staphylococcus aureus and show that some of these compounds have very good antibacterial activity.     

Efficient Separation of Phytochemicals from Muehlenbeckia volcanica (Benth.) Endl. by Polarity-Stepwise Elution Counter-Current Chromatography and Their Antioxidant,Antiglycation, and Aldose Reductase Inhibition Potentials

Muehlenbeckia volcanica (Benth.) Endl. (M. volcanica), native to South America, is a traditional Peruvian medicinal plant that has multi-therapeutic properties; however, no phytochemicals have been identified from it yet. In this study, a five-step polarity-stepwise elution counter-current chromatography (CCC) was developed using methanol/water (1:5, v/v) as the stationary phase and different ratios of n-hexane, ethyl acetate, and n-butanol as mobile phases to separate the compounds from the 70% methanol extract of M. volcanica, by which six compounds with a wide range of polarities were separated in a single run of CCC and were identified as gallic acid, protocatechuic acid, 4,4′-dihydroxy-3,3′-imino-di-benzoic acid, rutin, quercitrin, and quercetin. Then, two compounds from the fractions of stepwise elution CCC were separated using conventional high-speed CCC, pH-zone-refining CCC, and preparative high-performance liquid chromatography, and identified as shikimic acid and miquelianin. These compounds are reported from M. volcanica for the first time. Notably, except for shikimic acid, all other compounds showed anti-diabetic potentials via antioxidant, antiglycation, and aldose reductase inhibition. The results suggest that the polarity-stepwise elution CCC can be used to efficiently separate or fractionate compounds with a wide range of polarities from natural products. Moreover, M. volcanica and its bioactive compounds are potent anti-diabetic agents.     

A Review: Halogenated Compounds from Marine Actinomycetes

Marine actinomycetes, Streptomyces species, produce a variety of halogenated compounds with diverse structures and a range of biological activities owing to their unique metabolic pathways. These halogenated compounds could be classified as polyketides, alkaloids (nitrogen-containing compounds) and terpenoids. Halogenated compounds from marine actinomycetes possess important biological properties such as antibacterial and anticancer activities. This review reports the sources, chemical structures and biological activities of 127 new halogenated compounds originated mainly from Streptomyces reported from 1992 to 2020.     

Analysis of Plant–Plant Interactions Reveals the Presence of Potent Antileukemic Compounds

A method to identify anticancer compounds in plants was proposed based on the hypothesis that these compounds are primarily present in plants to provide them with an ecological advantage over neighboring plants and other competitors. According to this view, identifying plants that contain compounds that inhibit or interfere with the development of other plant species may facilitate the discovery of novel anticancer agents. The method was developed and tested using Magnolia grandiflora, Gynoxys verrucosa, Picradeniopsis oppositifolia, and Hedyosmum racemosum, which are plant species known to possess compounds with cytotoxic activities. Plant extracts were screened for growth inhibitory activity, and then a thin-layer chromatography bioautography assay was conducted. This located the major antileukemic compounds 1, 2, 4, and 5 in the extracts. Once the active compounds were located, they were extracted and purified, and their structures were determined. The growth inhibitory activity of the purified compounds showed a significant correlation with their antileukemic activity. The proposed approach is rapid, inexpensive, and can easily be implemented in areas of the world with high biodiversity but with less access to advanced facilities and biological assays.     

Azo compounds with different sized fluorophores and characterization of their photophysical properties based on trans to cis conformational change

We synthesized fluorophores of different sizes attached to azo derivatives, such as thiophene-, naphthalene-, anthracene-, and pyrene-based azo compounds, and studied their photophysical properties. The compounds exhibited strong color and intensity changes in absorption and emission during the structural change from trans to cis, which also resulted in a large Stokes shift and a difference in quantum yield. Depending on their size, the compounds had different rates of transformation from the trans to cis structure: less conjugated (smaller) fluorophore azo compounds showed higher transition rates than more conjugated (larger) ones.     

Two new tricycloalternarenes from Hawaiian endophytic fungus Didymella sp. FT433

Two new compounds, tricycloalterenes M and N (1 and 2) and six known analogs were isolated from the cultured broth of Didymella sp. FT433. The structures of all the compounds were elucidated through the analysis of HRMS and NMR spectroscopic data. The absolute configurations (AC) of the new compounds were determined by CD. All compounds were tested against A2780 and cisplatin resistant A2780 (A2780CisR) cell lines, and pathogenic bacteria Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa, but none was active.     

Domestication of Plants of Ugni molinae Turcz (Myrtaceae) Interferes in the Biology of Chilesia rudis (Lepidoptera: Erebidae) Larvae

In terms of the domestication process in murtilla, studies have found changes in the concentration of phenolic compounds, with reduction of chemical defense of plants, depending on the change in the feeding behavior of insects. Thus, we hypothesized that the domestication of Ugni molinae decreases the content of phenolic compounds and modifies the feeding preference of Chilesia rudis larvae. Leaves of three parental ecotypes and four cultivated ecotypes were used in preference experiments to evaluate the mass gain and leaves consumption of larvae. Phenolic extracts from leaves of U. molinae were analyzed by HPLC. Identified compounds were incorporated in an artificial diet to assess their effect on mass gain, consumption, and survival of the larvae. The presence of phenolic compounds in bodies and feces was also evaluated. In terms of choice assays, larvae preferred parental ecotypes. Regarding compounds, vanillin was the most varied between the ecotypes in leaves. However, plant domestication did not show a reduction in phenolic compound concentration of the ecotypes studied. Furthermore, there was no clear relation between phenolic compounds and the performance of C. rudis larvae. Whether this was because of sequestration of some compounds by larvae is unknown. Finally, results of this study could also suggest that studied phenolic compounds have no role in the C. rudis larvae resistance in this stage of murtilla domestication process.     

Novel Bio-Functional Aloe vera Beverages Fermented by Probiotic Enterococcus faecium and Lactobacillus lactis

Aloe vera has been medicinally used for centuries. Its bioactive compounds have been shown to be very effective in the treatment of numerous diseases. In this work, a novel functional beverage was developed and characterized to combine the health benefits of probiotic bacteria with the Aloe vera plant itself. Two Aloe vera juices were obtained by fermentation either by a novel isolated Enterococcus faecium or a commercial Lactococcus lactis. The extraction of Aloe vera biocompounds for further fermentation was optimized. Extraction with water plus cellulase enhanced the carbohydrates and phenolic compounds in the obtained extracts. The biotransformation of the bioactive compounds from the extracts during fermentation was assessed. Both probiotic bacteria were able to grow on the Aloe vera extract. Lactic acid and short-chain fatty acids (SCFA) together with fourteen individual phenolic compounds were quantified in the produced Aloe vera juice, mainly epicatechin, aloin, ellagic acid, and hesperidin. The amount of total phenolic compounds was maintained through fermentation. The antioxidant activity was significantly increased in the produced juice by the ABTS method. The novel produced Aloe vera juice showed great potential as a functional beverage containing probiotics, prebiotics, SCFA, and phenolic compounds in its final composition.     

Cyclisation of (4S)-4-methyl-2-phenethyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione derivatives via N-acyliminium ions

Enantiomerically pure 1-methylene and 1-oxo derivatives (compounds 4 and 10, respectively) of compounds 1 were obtained and studied as precursors of N-acyliminium ions. 1-Substituted-1-hydroxyderivatives, obtained by regioselective syn-addition of organometallics to compounds 10 gave the desired species under acid treatment while compounds 4 did not. N-Phenethyl substituted N-acyliminium ions gave isoquino[1′,2′:3,4]pyrazino[2,1-b]quinazoline-8,11-diones through a Pictet–Spengler-type cyclisation.     

Determination of Octanol–Water Partition Coefficients by MEEKC Based on Peak-Shift Assay

A novel microemulsion electrokinetic chromatography method based on peak-shift assay (p-s MEEKC) has been developed for the determination of octanol–water partition coefficients (log P _o/w) of compounds. The log P _o/w values of 12 compounds were determined. The RSD of obtained values were less than 5.0% except 4-tert-butylphenol (RSD = 5.9%). All log P _o/w values of the investigated compounds measured by p-s MEEKC were within 0.51 logarithm unit variation as compared to the literature values, with mean difference of 0.27. Compared to the conventional MEEKC method, the novel method does not suffer from the deficiencies related to the reference compounds and migration time of microemulsion phase, and showed the potential of being an alternative method for the determination of log P _o/w values of compounds without reference compounds.     

Synthesis,characterization and evaluation of antidengue activity of enantiomeric Schiff bases derived from S-substituted dithiocarbazate

A series of Schiff bases have been successfully synthesized through the acid-catalyzed condensation of S-substituted dithiocarbazates and three enantiomerically pure monoterpenes, (1 R )-(+)-camphor, (1 S )-(-)-camphor, (1 R )-(-)-camphorquinone, (1 S )-(+)-camphorquinone, ( R )-(-)-carvone and ( S )-(+)-carvone. Spectroscopic results revealed that the Schiff bases containing camphor or carvone likely adopted an E -configuration along the characteristic imine bond while those containing camphorquinone assumed a Z -configuration. The antidengue potential of these compounds was evaluated based on DENV 2 caused cytopathic effect (CPE) reduction-based in vitro evaluation. The compounds were validated through secondary foci forming unit reduction assay (FFURA). Compounds were also tested for their cytotoxicity against Vero cells. The compounds showed variable degrees of antiviral activity with the camphor compounds displaying the highest antidengue potential. The enantiomers of the compounds behaved almost similarly during the antiviral evaluation.     

Substituent effect of fluorine atoms in the 2,4-difluorophenyl group on antifungal activity of CS-758

CS-758 is a novel triazole antifungal agent. To ascertain the effect of the fluorine atoms in the 2,4-difluorophenyl group, a series of compounds, 12a–12d, which have fluorine atom(s) in different positions on the benzene ring, were synthesized, and the minimum inhibitory concentrations (MICs) of this series of compounds were determined. All the compounds, including CS-758, exhibited excellent MICs against Candida, Aspergillus, and Cryptococcus species. Among them, the compounds having a fluorine atom in the 2-position on the benzene ring (12a, 12c, 12d, and CS-758) showed stronger antifungal activity particularly against Aspergillus species. The MICs of these compounds surpassed those of fluconazole and itraconazole against Candida, Aspergillus, and Cryptococcus species.     

<em>N</em>-Substituted 5-Chloro-6-phenylpyridazin-3(2<em>H</em>)-ones: Synthesis, Insecticidal Activity Against <em>Plutella xylostella </em>(L.) and SAR Study

A series of N-substituted 5-chloro-6-phenylpyridazin-3(2H)-one derivatives were synthesized based on our previous work; all compounds were characterized by spectral data and tested for in vitro insecticidal activity against Plutella xylostella. The results showed that the synthesized pyridazin-3(2H)-one compounds possessed good insecticidal activities, especially the compounds 4b, 4d, and 4h which showed > 90% activity at 100 mg/L. The structure-activity relationships (SAR) for these compounds were also discussed.     

The Difference of Volatile Compounds in Female and Male Buds of Herpetospermum pedunculosum Based on HS-SPME-GC-MS and Multivariate Statistical Analysis

Herpetospermum pedunculosum (Ser.) C. B. Clarke (Family Cucurbitaceae) is a dioecious plant and has been used as a traditional Tibetan medicine for the treatment of hepatobiliary diseases. The component, content, and difference in volatile compounds in the female and male buds of H. pedunculosum were explored by using headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) technology and multivariate statistical analysis. The results showed that isoamyl alcohol was the main compound in both female and male buds and its content in males was higher than that in females; 18 compounds were identified in female buds including 6 unique compounds such as (E)-4-hexenol and isoamyl acetate, and 32 compounds were identified in male buds, including 20 unique compounds such as (Z)-3-methylbutyraldehyde oxime and benzyl alcohol. (Z)-3-methylbutyraldehyde oxime and (E)-3-methylbutyraldehyde oxime were found in male buds, which only occurred in night-flowering plants. In total, 9 differential volatile compounds between female and male buds were screened out, including isoamyl alcohol, (Z)-3-methylbutanal oxime, and 1-nitropentane based on multivariate statistical analysis such as principal component analysis (PCA) and orthogonal partial least squares discrimination analysis (OPLS-DA). This is the first time to report the volatile components of H. pedunculosum, which not only find characteristic difference between female and male buds, but also point out the correlation between volatile compounds, floral odor, and plant physiology. This study enriches the basic theory of dioecious plants and has guiding significance for the production and development of H. pedunculosum germplasm resources.