Phenolic Esters Research Articles

Esterase-Responsive Polymeric Micelles Containing Tetraphenylethene and Poly(ethylene glycol) Moieties for Efficient Doxorubicin Delivery and Tumor Therapy.

Enzyme-responsive drug delivery systems have drawn much attention in the field of cancer theranostics due to their high sensitivity and substrate specificity under mild conditions. In this study, an amphiphilic polymer T1 is reported, which contains a tetraphenylethene unit and a poly(ethylene glycol) chain linked by an esterase-responsive phenolic ester bond. In aqueous solution, T1 formed stable micelles via self-assembly, which showed an aggregation-induced emission enhancement of 32-fold at 532 nm and a critical micelle concentration of 0.53 μM as well as esterase-responsive activity. The hydrophobic drug doxorubicin (DOX) was efficiently encapsulated into the micelles with a drug loading of 21%. In the presence of the esterase, the selective decomposition of drug-loaded T1 micelles was observed, and DOX was subsequently released with a half-life of 5 h. In vitro antitumor studies showed that T1@DOX micelles exhibited good therapeutic effects on HeLa cells, while normal cells remained mostly intact. In vivo anticancer experiments revealed that T1@DOX micelles indeed suppressed tumor growth and had reduced side effects compared to DOX·HCl. The present work showed the potential clinical application of esterase-responsive drug delivery in cancer therapy.

In-suit ion-imprinted bio-sorbent with superior adsorption performance for gallium(III) capture

A superior persimmon peel-based imprinted material (Ga-IIP-PP-OP) was obtained by optimizing the preparation conditions such as cross-linking agent dosage, type of solvent, addition amount of template ions, polymerization temperature and polymerization time. The internal and external morphology and structure of Ga-IIP-PP-OP were examined by SEM, TEM and BET, and the adsorption mechanism of gallium ions on Ga-IIP-PP-OP was analyzed by FTIR, XPS and DFT calculation. The results showed that under the optimum conditions (methanol-water (3:7) as solvent, addition amount of template ions = 1.42 μmol, cross-linking agent dosage = 0.351 mg/g pp powder, polymerization temperature = 80 °C, polymerization time = 6 h), the adsorption capacity of Ga-IIP-PP-OP can reach 352.64 mg/g under pH = 3, which is significantly higher than other reported gallium adsorbents. Moreover, Ga-IIP-PP-OP with abundant porous structure and dense cross-linking network exhibited a strong affinity for Ga (III) even in binary systems with similar competitive ions. The remarkable adsorption capacity of Ga-IIP-PP-OP is attributed to electrostatic attraction of phenoxy negative ions to Ga (III) and chelation of phenolic hydroxyl and ester groups with Ga (III), with an ester group in the tannin structural unit and adjacent hydroxyl groups on another structural unit as the most stable adsorption site. These results revealed that the optimization of the synthesis conditions allowed the imprinted material to demonstrate greater potential for selective adsorption and efficient recovery of Ga (III).

Affinity of K+to organic matter promotes reactions: degradation of super stable phenolic epoxy vinyl ester resin to value-added chemicals

An efficient catalytic system was developed to cleave the ester bond of highly stable waste thermoset phenolic epoxy vinyl ester resin and recover value-added chemicals.

Passive Adsorption of Aromatic Substances on Silicon Carbide and Nitrile Rubber Composites and a Comparison of the Chromatographic Profiles of Banana Candy, Fresh Banana, and “Banana” Flavor

A domestic composite material based on silicon carbide and nitrile butadiene rubber was used to identify volatile substances of banana, banana flavor, and creamy chewing candies by passive adsorption in combination with thermal desorption GC–MS. This method can be used to determine a wide range of compounds, for example, esters of carboxylic acids, terpenoids, aldehydes, aromatic hydrocarbons, alkanes, heterocyclic compounds, phenols, glycerides, and fatty acids. The obtained chromatographic profiles of the samples were compared. In the chromatogram of “Banana” flavor, five peaks (out of eight) corresponded to the compounds that form the aroma of a banana, and in the chromatogram of “Love is” candies with banana flavor, three corresponding peaks (out of 21) were found.

Ursolic acid and rosmarinic acid ameliorate alterations in hippocampal neurogenesis and social memory induced by amyloid beta in mouse model of Alzheimer's disease.

Alzheimer's disease (AD) is a multifaceted neurodegenerative disorder characterized by substantial neuronal damage which manifests in the form of deficits in memory and cognition. In spite of the debilitating nature of Alzheimer's disease (AD), a dearth of treatment strategies calls for the need to develop therapeutic agents that stimulate neurogenesis and alleviate the associated cognitive deficits. The present study investigates the therapeutic potential of two major phytochemicals, rosmarinic acid (RA) and ursolic acid (UA) in an amyloid beta1-42 (Aβ1-42)-induced model of AD. UA, a natural pentacyclic triterpenoid and RA, a phenolic ester are major bioactive constituents of Rosmarinus officinalis, which is a medicinal herb belonging to family Lamiaceae and exhibiting significant biological properties including neuroprotection. Donepezil, a second generation cholinesterase inhibitor approved for the treatment of mild, moderate and severe Alzheimer's disease (AD) is used as control. Out of eight groups of male BALB/c mice, stereotaxic surgery was performed on four groups (n = 6 each) to introduce Aβ1-42 in the hippocampus followed by treatment with vehicle (phosphate-buffered saline (PBS)), donepezil, UA or RA. The other four groups were given vehicle, donepezil, UA and RA only. Behavior analysis for social interaction was performed which constitutes the social affiliation and the social novelty preference test. Presence of Aβ plaques and expression of neurogenesis markers i.e., doublecortin (DCX) and Ki-67 were also assessed. Results revealed the neuroprotective effect of UA and RA observed through substantial reduction in Aβ plaques as compared to the Aβ1-42- and donepezil-treated groups. The neuronal density was also restored as evident via DCX and Ki-67 immunoreactivity in Aβ1-42 + RA and Aβ1-42+UA-treated groups in comparison to Aβ1-42-treated and Aβ1-42+donepezil-treated groups. The social affiliation was reestablished in the Aβ1-42 administered groups treated with UA and RA. Molecular docking studies further validated the comparable binding of UA and RA with Ki-67 and DCX to that of donepezil. Our findings suggest that UA and RA are potential neuroprotective compounds that reverses the histological hallmarks of AD and ameliorate impaired social memory and hippocampal neurogenesis.

Poly(pro-curcumin) Materials Exhibit Dual Release Rates and Prolonged Antioxidant Activity as Thin Films and Self-Assembled Particles.

Curcumin is a natural polyphenol that exhibits remarkable antioxidant and anti-inflammatory activities; however, its clinical application is limited in part by its physiological instability. Here, we report the synthesis of curcumin-derived polyesters that release curcumin upon hydrolytic degradation to improve curcumin stability and solubility in physiological conditions. Curcumin was incorporated in the polymer backbone by a one-pot condensation polymerization in the presence of sebacoyl chloride and polyethylene glycol (PEG, Mn = 1 kDa). The thermal and mechanical properties, surface wettability, self-assembly behavior, and drug-release kinetics all depend sensitively on the mole percentage of curcumin incorporated in these statistical copolymers. Curcumin release was triggered by the hydrolysis of phenolic esters on the polymer backbone, which was confirmed using a PEGylated curcumin model compound, which represented a putative repeating unit within the polymer. The release rate of curcumin was controlled by the hydrophilicity of the polymers. Burst release (2 days) and extended release (>8 weeks) can be achieved from the same polymer depending on curcumin content in the copolymer. The materials can quench free radicals for at least 8 weeks and protect primary neurons from oxidative stress in vitro. Further, these copolymer materials could be processed into both thin films and self-assembled particles, depending on the solvent-based casting conditions. Finally, we envision that these materials may have potential for neural tissue engineering application, where antioxidant release can mitigate oxidative stress and the inflammatory response following neural injury.

Solid acid HND‐26 as a novel catalyst: Green and sustainable alternatives towards synthesis of benzyl cinnamate

AbstractHigh melting point and hydrophilicity of phenolic acids limit their application in lipophilic environments such as fat‐containing cosmetics and foods. The esterification of the carboxyl group with fatty and aromatic alcohols has been considered as an effective way to enhance the lipophilicity of phenolic acids and thus enable better location of the antioxidant moiety into membranes and interface of emulsion systems where oxidation is expected to occur. Therefore, this study aims to evaluate the catalytic properties of six solid acids (HND‐34, HND‐6, HND‐580, HND‐2, HND‐8 and HND‐26) for the synthesis of benzyl cinnamate. Results show that HND‐26 was the most effective solid acid to catalyse the esterification reaction of cinnamic acid with benzyl alcohol. By using response surface methodology, the influence of key experimental factors on the yield of benzyl cinnamate was investigated and the maximum yield (95.1%) was obtained under the optimized conditions (58°C, cinnamic acid/benzyl alcohol 1:20 (mol/mol), HND‐26 loading 13.8% and 25 hours). The activation energy of cinnamic acid conversion with benzyl alcohol was 30.3 kJ/mol. Obtained results provide a cost‐effective way of green synthesis of benzyl cinnamate and highlights the potential applications of HND‐26 as an efficient catalyst for the production of phenolic acid esters with broad usage in cosmetic industry.

Phytochemical Characterization of Chamomile (Matricaria recutita L.) Roots and Evaluation of Their Antioxidant and Antibacterial Potential

Matricaria recutita L., German chamomile, is one of the most widely used medicinal plants, whose efficacy has been proven in numerous studies. However, its roots have attracted only little interest so far, since mainly above-ground plant parts are used for medicinal purposes. To broaden the knowledge of chamomile roots, a profound phytochemical characterization was performed along with a bioactivity screening of corresponding root extracts. While volatile constituents such as chamomillol and polyynes were detected using GC-MS, HPLC-MSn analyses revealed the occurrence of four coumarin glycosides, more than ten phenolic acid esters and five glyceroglycolipids. Furthermore, the antioxidant activity of the extracts was evaluated. Polar extracts revealed IC50 values ranging from 13 to 57 µg/mL in the DPPH radical scavenging assay, which is in the same range as reported for chamomile flower extracts. In addition, superoxide radical scavenging potential and mild antibacterial effects against S. aureus und B. subtilis were demonstrated. Moreover, to assess interspecies variation in chamomile roots, extracts of M. recutita were compared to those of M. discoidea DC. Interestingly, the latter revealed stronger antioxidant activity. The presented results aim at the valorization of chamomile roots, previously discarded as by-product of chamomile flower production, as a sustainable source of bioactive phytochemicals.

Cytotoxicity effect of nanoparticles of Euphorbia antiquorum on breast cancer cell line

Euphorbia antiquorum was known for its various therapeutic values like anti-inflammatory, anti-diabetic activity etc. Preliminary phytochemicals screening of plant extract disclosed the existence of various important bioactive constituents in hexane, ethanol and aqueous extract of the plant. Aqueous extract of Euphorbia antiquorum was used for silver and copper nanoparticle synthesis. Synthesized silver and copper nanoparticle showed the absorbance line at 422 and 367 nm respectively. Fourier-transform infrared spectroscopy analysis of synthesized nanoparticles reported the presence of phenol groups, amines and esters. Shape and morphology of the synthesized nanoparticles were characterized through Field Emission Scanning Electron Microscopy which showed the spherical shaped nanoparticles. Energy dispersive X-ray spectroscopy images showed the composition of analysed nanoparticles. The antioxidant activity of synthesized silver and copper nanoparticles of Euphorbia antiquorum by hydrogen peroxide scavenging activity method using ascorbic acid as the standard showed effective scavenging activity and indicated the potentiality of the plant as a source of natural antioxidant. Cytotoxicity study of silver nanoparticles showed 73.22% of inhibition at the concentration of 1000 µg/ml whereas copper nanoparticles at the same concentration showed 68.85% of inhibition against breast cancer cell line.

Antimicrobial properties of phenolic acid alkyl esters

The series of phenolic acid (2-, 3-, 4-monohydroxy- and 2,4-, 2,5-dihydroxy) alkyl esters (methyl, ethyl, propyl, and butyl) were prepared, and their antimicrobial activities were determined. The antimicrobial activity against the tested microorganisms Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and Aspergillus brasiliensis was investigated and expressed by minimum inhibitory concentration (MIC) in the range of 1.2–20 mM. The inhibitory activity of higher esters of phenolic acids was found to be higher than that of methyl esters and acids. The minimum inhibitory concentration (MIC) of tested compounds was compared with that of 4-hydroxybenzoic acid and its esters (parabens).

Mechanism-Driven Development of Group 10 Metal-Catalyzed Decarbonylative Coupling Reactions.

Transition-metal-catalyzed cross-coupling reactions are widely used in both academia and industry for the construction of carbon-carbon and carbon-heteroatom bonds. The vast majority of cross-coupling reactions utilize aryl (pseudo)halides as the electrophilic coupling partner. Carboxylic acid derivatives (RC(O)X) represent a complementary class of electrophiles that can engage in decarbonylative couplings to produce analogous products. This decarbonylative approach offers the advantage that RC(O)X are abundant and inexpensive. In addition, decarbonylative coupling enables both intramolecular (between R and X of the carboxylic acid derivative) as well as intermolecular bond-forming reactions (in which an exogeneous nucleophile is coupled with the R group derived from RC(O)X). In these intermolecular reactions, the X-substituent on the carboxylic acid can be tuned to facilitate both oxidative addition and transmetalation, thus eliminating the need for an exogeneous base. This Account details our group's development of a diverse variety of base-free decarbonylative coupling reactions catalyzed by group 10 metals. Furthermore, it highlights how catalyst design can be guided by stoichiometric organometallic studies of these systems.Our early studies focused on intramolecular decarbonylative couplings that transform RC(O)X to the corresponding R-X with extrusion of CO. We first identified Pd and Ni monodentate phosphine catalysts that convert aryl thioesters (ArC(O)SR) to the corresponding thioethers (ArSR). We next expanded this reactivity to fluoroalkyl thioesters, using readily available fluoroalkyl carboxylic acids as the fluoroalkyl (RF) source. A Ni-phosphinoferrocene catalyst proved optimal, and the large bite angle bidentate ligand was necessary to promote the challenging RF-S bond-forming reductive elimination step.We next pursued intramolecular decarbonylative couplings of aroyl halides. Palladium-based catalysts bearing dialkylbiaryl ligands (e.g., BrettPhos) were identified as optimal for converting aroyl chlorides (ArC(O)Cl) to aryl chlorides (ArCl). These ligands were selected based on their ability to facilitate the key C-Cl bond-forming reductive elimination step of the catalytic cycle. In contrast, all attempts to convert aroyl fluorides [ArC(O)F)] to aryl fluorides (ArF) were unsuccessful with either Pd- or Ni-based catalysts. Organometallic studies of the Ni-system show that C(O)-F oxidative addition and CO deinsertion proceed smoothly, but the resulting nickel(II) aryl fluoride intermediate fails to undergo C-F bond-forming reductive elimination.In contrast to its inertness to reductive elimination, this nickel(II) aryl fluoride proved highly reactive toward transmetalation. The fluoride ligand serves as an internal base, such that no additional base is required. We leveraged this "transmetalation active" intermediate to achieve base-free Ni-catalyzed intermolecular decarbonylative coupling reactions between aroyl fluorides and boron reagents to access both biaryl and aryl-boronate ester products. By tuning the electrophile, transmetalating reagent, and catalyst, this same approach also proved applicable to base-free intermolecular decarbonylative fluoroalkylation (between difluoromethylacetyl fluoride and arylboronate esters) and aryl amination (between phenol esters and silyl amines).Moving forward, a key goal is to identify catalyst systems that enable more challenging bond constructions via this manifold. In addition, CO inhibition remains a major issue leading to the requirement for high temperatures and high catalyst loadings. Identifying catalysts that are resistant to CO binding and/or approaches to remove CO under mild conditions will be critical for making these reactions more practical and scalable.

α-Glucosidase Inhibitory and Antioxidant Activities of Ethanolic Extracts of Different Parts of Lysiphyllum strychnifolium and Their Constituents

ABSTRACT The crude ethanolic extracts of different parts (root, stem, leaves and flower) of Lysiphyllum strychnifolium were tested for α-glucosidase inhibitory and antioxidant activities. Since all extracts showed good inhibitory activity, active constituents were isolated. Thirteen known compounds, including three dihydroflavanones, three dihydrochalcones, two stilbenes, flavan-3-ol, flavonol, cyclitol, phenolic ethyl ester and phenolic acid were isolated, and their α-glucosidase inhibitory effect and antioxidant activity were evaluated. Phloretin 4’-O-(6”-O-galloyl)-β-D-glucoside from the leaves extract showed potent α-glucosidase inhibitory activity (IC50 = 0.0162 ± 0.0014 mM) and potent antioxidant activity (IC50 = 19.26 ± 0.95 μM), each more potent than the positive controls. The compounds were investigated for their structure–activity relationship (SAR) in both activities. The number and position of hydroxy groups seemed to play a crucial role in increasing α-glucosidase inhibitory and antioxidant activities.

Toxoplasmocidal and Cytotoxic Activities Guided Isolation and Characterization of an Undescribed Bioflavonoid-di-C-glucoside from Cycas rumphii Miq. Cultivated in Egypt.

Toxoplasmosis and cancer are serious worldwide diseases, and the available drugs cause serious side effects. Investigation for new alternative therapies from natural sources is now an increasing concern. Herein, we carried out, for the first time, an in vitro screening of Cycas rumphii Miq. leaves for toxoplasmocidal effect, using Viruluent RH Toxoplasma gondii, and cytotoxic activity against HEPG-2, HCT-116 and HELA cancer cell lines using MTT assay. Among the tested extracts, the ethyl acetate fraction was the most effective against T. gondii, with an EC50 of 3.51 ± 0.2 µg/mL compared to cotrimoxazole (4.18 ± 0.01 µg/mL) and was the most potent against the tested cell lines, especially HEPG-2, with an IC50 of 6.98 ± 0.5 µg/mL compared to doxorubicin (4.50 ± 0.2 µg/mL). Seven compounds were isolated from the ethyl acetate fraction by extensive chromatographic techniques and fully elucidated using different spectroscopies. Compound (7) is an undescribed 4', 4''' biapigenin di-C-glucoside, which showed a strong cytotoxic activity. Four known biflavonoids (1, 2, 4 and 5) in addition to a phenolic acid ester (3) and a flavonoid glycoside (6) were also isolated. Compounds (1, 3 and 6) were reported for the first time from C. rumphii.

Flavonol dioxygenase chemistry mediated by a synthetic nickel superoxide

Nature exploits transition metal centers to enhance and tune the oxidizing power of natural oxidants such as O2 and H2O2. The design and interrogation of synthetic metallocomplexes with similar reactivity to metalloproteins provides one strategy for gaining insight into the mechanistic underpinnings of oxygen-activating enzymes such as oxidases, oxygenases, and dioxygenases like Ni-quercetinase (Ni-QueD). Ni-QueD catalyzes the oxidative ring opening of the polyphenol quercetin, a natural product with antioxidant properties. Herein, we report the synthesis and characterization of Ni(13-DOB), a Ni(II) species complexed by an N4-macrocycle that has been characterized by single crystal X-ray crystallography. Ni(13-DOB) forms a Ni-superoxide intermediate (Ni(13-DOB)O2•-) upon treatment with H2O2 and Et3N, as verified by resonance Raman spectroscopy. We demonstrate through UV/vis and LCMS that Ni(13-DOB)O2•- is capable of the 1-electron oxidation of flavonols, including both 3-hydroxyflavone (3-HF, the simplest flavonol) and quercetin itself. Incorporation of two O-atoms into the flavonol radical via superoxide from Ni(13-DOB)O2•- precedes oxidative cleavage of the flavonol scaffold in each case, consistent with quercetinase ring cleavage by Ni-QueD in Streptomyces sp. FLA. Conversion of 3-HF into 2-hydroxybenzoylbenzoic acid was accomplished with catalytic turnover of Ni(13-DOB) at ambient temperature, as confirmed by HPLC timecourses and GCMS analysis of isotopic labeling studies. The Ni(13-DOB)-mediated oxidative cleavage of quercetin to the corresponding biomimetic phenolic ester was also verified through 18O-isotopic labeling studies. Through the HPLC characterization of both on- and off-pathway products of flavonol dioxygenation by Ni(13-DOB)O2•-, the stringent reaction pathway control provided by enzyme active sites is highlighted.

Site-Selective Lysine Acetylation of Human Immunoglobulin G for Immunoliposomes and Bispecific Antibody Complexes.

Site-selective acetylation of a single lysine residue in a protein that reaches a lysine acetyltransferase's accuracy, precision, and reliability is challenging. Here, we report a peptide-guided, proximity-driven group transfer reaction that acetylates a single lysine residue, Lys 248, of the fragment crystallizable region (Fc region) in the heavy chain of the human Immunoglobulin G (IgG). An Fc-interacting peptide bound with the Fc domain and positioned a phenolic ester close to Lys 248, which induced a nucleophilic reaction and resulted in the transfer of an acetyl group to Lys 248. The acetylation reaction proceeded to a decent yield under the physiological condition without the need for deglycosylation, unnatural amino acids, or catalysts. Along with acetylation, functional moieties such as azide, alkyne, fluorescent molecules, or biotin could also be site-selectively installed on Lys 248, allowing IgG's further derivatization. We then synthesized an antibody-lipid conjugate and constructed antibody-conjugated liposomes (immunoliposomes), targeting HER2-positive (HER2+) cancer cells. We also built a bispecific antibody complex (bsAbC) covalently linking an anti-HER2 antibody and an anti-CD3 antibody. The bsAbC showed in vitro effector-cell-mediated cytotoxicity at nanomolar concentrations. Compared with bispecific antibodies (bsAbs), bsAbCs are constructed based on native IgGs and contain two antigen-binding sites to each antigen, twice that of bsAbs. Altogether, this work reports a method of site-selective acetylation of native antibodies, highlights a facile way of site-selective IgG functionalization, and underscores the potential of bsAbCs in cancer immunotherapy.

Cytochrome b 5: A versatile electron carrier and regulator for plant metabolism.

Cytochrome b5 (CB5) is a small heme-binding protein, known as an electron donor delivering reducing power to the terminal enzymes involved in oxidative reactions. In plants, the CB5 protein family is substantially expanded both in its isoform numbers and cellular functions, compared to its yeast and mammalian counterparts. As an electron carrier, plant CB5 proteins function not only in fatty acid desaturation, hydroxylation and elongation, but also in the formation of specialized metabolites such as flavonoids, phenolic esters, and heteropolymer lignin. Furthermore, plant CB5s are found to interact with different non-catalytic proteins such as ethylene signaling regulator, cell death inhibitor, and sugar transporters, implicating their versatile regulatory roles in coordinating different metabolic and cellular processes, presumably in respect to the cellular redox status and/or carbon availability. Compared to the plentiful studies on biochemistry and cellular functions of mammalian CB5 proteins, the cellular and metabolic roles of plant CB5 proteins have received far less attention. This article summarizes the fragmentary information pertaining to the discovery of plant CB5 proteins, and discusses the conventional and peculiar functions that plant CB5s might play in different metabolic and cellular processes. Gaining comprehensive insight into the biological functions of CB5 proteins could offer effective biotechnological solutions to tailor plant chemodiversity and cellular responses to environment stimuli.

Comparative Metabolomics Analysis of Stigmas and Petals in Chinese Saffron (Crocus sativus) by Widely Targeted Metabolomics.

The dried stigmas of Crocus sativus, commonly known as saffron, are consumed largely worldwide because it is highly valuable in foods and has biological activities beneficial for health. Saffron has important economic and medicinal value, and thus, its planting area and global production are increasing. Petals, which are a by-product of the stigmas, have not been fully utilized at present. We compared the metabolites between the stigmas and petals of C. sativus using a non-targeted metabolomics method. In total, over 800 metabolites were detected and categorized into 35 classes, including alkaloids, flavonoids, amino acids and derivatives, phenols and phenol esters, phenylpropanoids, fatty acyls, steroids and steroid derivatives, vitamins, and other metabolites. The metabolite composition in the petals and stigmas was basically similar. The results of the study showed that the petals contained flavonoids, alkaloids, coumarins, and other medicinal components, as well as amino acids, carbohydrates, vitamins, and other nutritional components. A principal components analysis (PCA) and an orthogonal partial least-squares discriminant analysis (OPLS-DA) were performed to screen the different metabolic components. A total of 339 differential metabolites were identified, with 55 metabolites up-regulated and 284 down-regulated. The up-regulated metabolites, including rutin, delphinidin-3-O-glucoside, isoquercitrin, syringaresinol-di-O-glucoside, dihydrorobinetin, quercetin, and gallocatechin, were detected in the petals. The down-regulated metabolites were mainly glucofrangulin B, acetovanillone, daidzein, guaiazulene, hypaphorine, indolin-2-one, and pseudouridine. KEGG annotation and enrichment analyses of the differential metabolites revealed that flavonoid biosynthesis, amino acids biosynthesis, and arginine and proline metabolism were the main differentially regulated pathways. In conclusion, the petals of C. sativus are valuable for medicine and foods and have potential utility in multiple areas such as the natural spice, cosmetic, health drink, and natural health product industries.

Secondary Metabolites and their Biological Activities from Endophytic Fungal Strain Aspergillus terreus XJA8 Associated with Vernonia anthelmintica

Two isocoumarins (6-methoxymellein and 6-hydroxymellein), one pyrrole compound (minaline), one lactone derivative (butyrolactone II), five phenolic acids (phenylacetic, veratric (3,4-dimethoxybenzoic), 4-hydroxyphenylacetic, 4-hydroxybenzoic and protocatechuic acid), and two phenolic acid methyl esters ((2-hydroxyphenyl) acetic acid methyl ester and methyl 4-hydroxyphenylacetate), along with 1,3-bis(4-hydroxyphenyl) propan-2-one were isolated from the fungal strain Aspergillus terreus XJA8. The fungal strain was isolated from the root of the medicinal plant Vernonia anthelmintica for first time. All isolated secondary metabolites were evaluated for their antimicrobial activity and melanin synthesis in murine B16 cells.

Thermochemical Recycling of Solid Biomass Materials for Achieving Sustainable Goal: A Complete Characterization Study on Liquid Yield Products

In order to achieve sustainability goals, biomass is a renewable energy source that lowers emissions of greenhouse gases and other hazardous gases. Biochemical and thermochemical methods are both used to produce bioenergy from biomass. Pyrolysis is an effective thermochemical conversion technique used for the conversion of biomass into energy-rich bio-oil. In this study, the pyrolysis characteristics and bio-oil obtained from the residues of Ricinus communis were investigated. The experimental run was designed to analyze the impact of bed temperature on product yield by varying the process temperature from 350°C to 750°C. In this study, a maximum of 46.5 wt% of bio-oil was produced at 500°C. The maximum conversion was recorded at temperatures ranging from 450°C to 550°C. The bio-oil obtained at maximum yield conditions was analyzed using different analytical techniques. The Fourier transform infrared spectroscopy (FT-IR) and gas chromatography and mass spectroscopy (GC-MS) analyses of the bio-oil revealed that the oil has a significant amount of phenol derivatives, oxygenated chemicals, acids, and esters. The physical properties of the bio-oil showed that it is viscous and has a medium heating value compared with commercial fossil fuel.

Similar structural complexity of phenols in plant morphotypes with contrasting soluble phenol concentration and richness in arid rangelands of Patagonia

Phenols can play a significant role in plant tolerance of drought and herbivory. We assessed the concentration, richness and structural complexity of soluble phenols (hereafter phenols) in leaves of different species representing different plant morphotypes of arid ecosystems. We selected seven species representative of the three main plant morphotypes of the Patagonia Monte (Argentina): tall evergreen shrubs (TES), medium evergreen shrubs (MES), and perennial grasses (PG). These morphotypes differed in plant height, rooting depth, proportion of photosynthetic tissues, specific leaf area, and concentration of phenols and N in leaves. We found 48 compounds belonging to six types of phenols differing in structural complexity (low complexity: simple phenols, phenolic acids and phenolic esters; medium complexity: hydroxycinnamic acids and phenylpropenes; and high complexity: quinones, flavonols and flavones). Phenols of low and medium complexity were the most abundant in all morphotypes, while those of high complexity, probably the most costly for plants, were nearly exclusive of some tall evergreen shrubs. In general, PG, MES and TES had low, intermediate and high phenol concentration (8.5, 27.2, 202.5 mg g−1DW, respectively) and richness (15, 25, 37 compounds, respectively) in leaves. The richness of phenols was significantly and positively related to phenol concentration. However, we did not find distinctive phenol compound patterns among morphotypes. Our results suggest that drought and, to some extent, herbivory have exerted selective selection pressure on richness and phenol concentration in leaves of contrasting morphotypes but the type of phenols accumulated probably depends on intrinsic species attributes within each morphotype.