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1.
Food Res Int ; 188: 114475, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38823838

ABSTRACT

This work aimed to develop edible emulsion-based barriers in the form of chitosan composite films, with a focus on assessing the impacts of carnauba wax, rosin resin, and zinc oxide nanoparticles on their properties. Six films were produced by casting using chitosan as polymer base and glycerol as plasticizer. Acetic acid and polysorbate 80 were also used to facilitate the dissolution and mixing of the components. The six filmogenic solutions contained chitosan at 1.2% w/v, wax or resin content with 0 or 0.6% m/v and ZnO with 0 or 0.05% m/v. The dried films were characterized according to their chemical, barrier, mechanical, thermal and optical properties. All treatments resulted in flexible films. Chitosan films appeared smoother and more uniform under SEM imaging, while carnauba wax films displayed roughness due to their hydrophobic nature. Wax and resin films were less transparent and water soluble than the chitosan-only films. On the other hand, the addition of ZnO in the formulations increased the solubility of the films. The sorption degree was in line with the solubility results, i.e., films with ZnO presented higher sorption degree and solubility values. All treatments showed low or non-light UV transmission, indicating that the films provide good barrier to UV light. In the visible light region, films of resin with ZnO showed the lowest transmittance values, hence offering a good barrier to visible light. Among the evaluated films, chitosan, and resin films with ZnO nanoparticles were more rigid and resistant to deformation. Overall, films produced with rosin resin and ZnO nanoparticles showed potential improvements in barrier, mechanical, thermal, and optical properties, mainly due to their low water solubility, good UV protection and low permeability to water vapor and oxygen, which are suitable for using in formulations, intended to produce edible films and coatings.


Subject(s)
Chitosan , Nanocomposites , Resins, Plant , Solubility , Waxes , Zinc Oxide , Chitosan/chemistry , Zinc Oxide/chemistry , Nanocomposites/chemistry , Resins, Plant/chemistry , Waxes/chemistry , Nanoparticles/chemistry , Food Packaging/methods , Permeability
2.
Int J Biol Macromol ; 269(Pt 2): 132168, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38729496

ABSTRACT

Ferula spp. are plants that produce oleo-gum-resins (OGRs), which are plant exudates with various colors. These OGRs have various industrial applications in pharmacology, perfumery, and food. The main constituents of these OGRs are terpenoids, a diverse group of organic compounds with different structures and functions. The biosynthesis of OGRs in Ferula spp., particularly galbanum, holds considerable economic and ecological importance. However, the molecular and genetic underpinnings of this biosynthetic pathway remain largely enigmatic. This review provides an overview of the current state of knowledge on the biosynthesis of OGRs in Ferula spp., highlighting the major enzymes, genes, and pathways involved in the synthesis of different terpenoid classes, such as monoterpenes, sesquiterpenes, and triterpenes. It also examines the potential of using omics techniques, such as transcriptomics and metabolomics, and genome editing tools, such as CRISPR/Cas, to increase the yield and quality of Ferula OGRs, as well as to create novel bioactive compounds with enhanced properties. Moreover, this review addresses the current challenges and opportunities of applying gene editing in Ferula spp., and suggests some directions for future research and development.


Subject(s)
Ferula , Ferula/chemistry , Plant Gums/chemistry , Biosynthetic Pathways/genetics , Resins, Plant/chemistry , Terpenes/metabolism , Terpenes/chemistry , Gene Editing
3.
Spectrochim Acta A Mol Biomol Spectrosc ; 316: 124384, 2024 Aug 05.
Article in English | MEDLINE | ID: mdl-38701576

ABSTRACT

The bioactive compounds Acetyl-11-keto-ß-boswellic acid (AKBA) and 11-keto-ß-boswellic acid (KBA), found in the resin of the Boswellia tree, exhibit anti-inflammatory properties, rendering Boswellia resin an intriguing natural medicinal products. However, the content of boswellic acids varies across different Boswellia species and proper knowledge of its species-dependent nature, as well as alternatives to the resource- and time-intensive HPLC analysis, are lacking. Here we present a comprehensive investigation into the boswellic acid content of seven Boswellia species from ten countries and introduce a novel and non-destructive Near-Infrared spectroscopy method for predicting boswellic acid concentrations in solid resin samples. The HPLC-UV reference analysis revealed AKBA concentrations of up to 7.27 % (w/w) with KBA concentrations reaching up to 1.28 % (w/w). Principal Component Analysis of the HPLC and NIR spectroscopy data unveiled species-specific variations, facilitating differentiation based on boswellic acid content, characteristic chromatograms and NIR spectra. Using the HPLC-UV quantification as reference, we developed a Partial Least Squares regression model based on NIR spectra of the resin samples. This model demonstrated highly satisfactory predictive capabilities for AKBA content, achieving a root mean square error of prediction of 0.74 % (w/w) and an R2val of 0.79 in independent test set validation. Although the model was less effective for predicting KBA content, it still offered valuable estimates. The spectroscopic method introduced in this study provides a cost-effective and solvent-free approach for predicting boswellic acid content, demonstrating the potential for application in non-laboratory settings through the use of miniaturized NIR spectrometers. Consequently, this method aligns well with the principles of green chemistry and addresses the growing demand for alternative analytical techniques.


Subject(s)
Boswellia , Principal Component Analysis , Resins, Plant , Spectroscopy, Near-Infrared , Triterpenes , Boswellia/chemistry , Spectroscopy, Near-Infrared/methods , Triterpenes/analysis , Chromatography, High Pressure Liquid/methods , Resins, Plant/chemistry , Resins, Plant/analysis , Multivariate Analysis , Species Specificity
4.
Carbohydr Res ; 540: 109142, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38718742

ABSTRACT

Resin glycosides act as laxatives in crude drugs derived from plants of the Convolvulaceae family. These compounds have exhibited antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug resistance-modulating properties, as well as cytotoxicity against cancer cells. This study investigated the organic acid, hydroxyl fatty acid, monosaccharide, and glycosidic acid components of the crude resin glycoside fraction obtained from the methanol extract of Ipomoea alba L. (Convolvulaceae) seeds, which was subjected to alkaline and acidic hydrolysis. The alkaline hydrolysis yielded acetic, isobutyric, (E)-2-methylbut-2-enoic, and 2S-methyl-3S-hydroxybutyric acids as organic acid components, along with a glycosidic acid fraction. The acidic hydrolysis of the glycosidic acid fraction resulted in the isolation of 11S-hydroxytetradecanoic and 11S-hydroxyhexadecanoic acids as hydroxyl fatty acid components, as well as d-glucose, d-quinovose, d-fucose, d-xylose, and l-rhamnose as monosaccharide components. In addition, 10 new glycosidic acid methyl esters were isolated from the glycosidic acid fraction treated with trimethylsilyldiazomethane-hexane, along with one known glycosidic acid methyl ester. Of these, eight compounds contained new glycans. Four of these compounds were unusual natural glycosides with four glycosidic linkages to one monosaccharide. Their structures were determined using MS and NMR spectral analyses, which provided valuable insights into the unique glycosidic composition of I. alba seeds.


Subject(s)
Glycosides , Ipomoea , Seeds , Ipomoea/chemistry , Glycosides/chemistry , Glycosides/isolation & purification , Glycosides/pharmacology , Seeds/chemistry , Resins, Plant/chemistry , Hydrolysis , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Extracts/isolation & purification
5.
Langmuir ; 40(21): 10992-11010, 2024 May 28.
Article in English | MEDLINE | ID: mdl-38743441

ABSTRACT

The exploration of environmentally friendly, less toxic, sustained-release insecticide is increasing with the growing demand for food to meet the requirements of the expanding population. As a sustained-release carrier, the unique, environmentally friendly intelligent responsive hydrogel system is an important factor in improving the efficiency of insecticide utilization and accurate release. In this study, we developed a facile approach for incorporating the natural compound rosin (dehydroabietic acid, DA) and zinc ions (Zn2+) into a poly(N-isopropylacrylamide) (PNIPAM) hydrogel network to construct a controlled-release hydrogel carrier (DA-PNIPAM-Zn2+). Then, the model insecticide avermectin (AVM) was encapsulated in the carrier at a drug loading rate of 36.32% to form AVM@DA-PNIPAM-Zn2+. Surprisingly, the smart controlled carrier exhibited environmental responsiveness, strongly enhanced mechanical properties, self-healing ability, hydrophobicity, and photostability to ensure a balance between environmental friendliness and the precision of the drug release. The release experiments showed that the carboxyl and amide groups in the polymer chains alter the intermolecular forces within the hydrogel meshes and ingredient diffusion by changing temperatures (25 and 40 °C) and pH values (5.8, 7.4, and 8.5), leading to different release behaviors. The insecticidal activity of the AVM@DA-PNIPAM-Zn2+ against oriental armyworms was good, with an effective minimum toxicity toward aquatic animals. Therefore, AVM@DA-PNIPAM-Zn2+ is an effective drug delivery system against oriental armyworms. We anticipate that this ecofriendly, sustainable, smart-response carrier may broaden the utilization rosin and its possible applications in the agricultural sector.


Subject(s)
Drug Carriers , Hydrogels , Insecticides , Ivermectin , Resins, Plant , Ivermectin/analogs & derivatives , Ivermectin/chemistry , Ivermectin/pharmacology , Ivermectin/toxicity , Hydrogels/chemistry , Hydrogels/pharmacology , Animals , Hydrogen-Ion Concentration , Insecticides/chemistry , Insecticides/pharmacology , Resins, Plant/chemistry , Drug Carriers/chemistry , Temperature , Delayed-Action Preparations/chemistry , Delayed-Action Preparations/pharmacology , Drug Liberation , Moths/drug effects , Rosaceae/chemistry , Zinc/chemistry , Zinc/pharmacology , Acrylic Resins
6.
Int J Biol Macromol ; 269(Pt 2): 132136, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38718999

ABSTRACT

In this work, shellac plasticized with oleic acid was solvent cast to prepare the flexible and water-resistant film for packaging applications. The films were prepared with varying amounts of oleic acid and studied in detail for appearance, surface morphology, thermal, chemical, barrier, mechanical, and robustness. The surface morphology confirmed the smooth surface of films up to SH-OA20 (100:20 w/w; shellac: oleic acid). Fourier-transform infrared spectroscopy confirmed that oleic acid reduced the hydrogen bonding of the shellac matrix to provide a plasticization effect. Also, the thermal analysis showed a reduction in the melting enthalpy. Moreover, the plasticized films had a better barrier to water vapor due to increased smoothness and reduction in brittleness. Adding oleic acid also increased the elongation at break up to 40 % without any changes in tensile strength. The flexibility of the films increased with the oleic acid content, making them resistant to burst, crumbling, bending, rolling, and stretching. Oleic acid also showed the retardation of aging and thermal aging of shellac. In the future, the long-term stability and migration of the films can be investigated.


Subject(s)
Oleic Acid , Tensile Strength , Water , Oleic Acid/chemistry , Water/chemistry , Edible Films , Chemical Phenomena , Temperature , Spectroscopy, Fourier Transform Infrared , Steam , Resins, Plant
7.
Molecules ; 29(10)2024 May 09.
Article in English | MEDLINE | ID: mdl-38792084

ABSTRACT

Labdanum resin or "gum" can be obtained from Cistus ladanifer L. by two different extraction methods: the Zamorean and the Andalusian processes. Although its main use is in the fragrance and perfumery sectors, ethnobotanical reports describe its use for medicinal purposes in managing hyperglycemia and mental illnesses. However, data concerning the bioactivities and pharmacological applications are scarce. In this work, it was found that the yield of labdanum resin extracted by the Andalusian process was 25-fold higher than the Zamorean one. Both resins were purified as absolutes, and the Andalusian absolute was purified into diterpenoid and flavonoid fractions. GC-EI-MS analysis confirmed the presence of phenylpropanoids, labdane-type diterpenoids, and methylated flavonoids, which are already described in the literature, but revealed other compounds, and showed that the different extracts presented distinct chemical profile. The potential antidiabetic activity, by inhibition of α-amylase and α-glucosidase, and the potential neuroprotective activity, by inhibition of acetylcholinesterase, were investigated. Diterpenoid fraction produced the higher α-amylase inhibitory effect (~30% and ~40% at 0.5 and 1 mg/mL, respectively). Zamorean absolute showed the highest α-glucosidase inhibitory effect (~14% and ~24%, at 0.5 and 1 mg/mL, respectively). Andalusian absolute showed the highest acetylcholinesterase inhibitory effect (~70% and ~75%, at 0.5 and 1 mg/mL, respectively). Using Caco-2 and HepG2 cell lines, Andalusian absolute and its purified fractions showed moderate cytotoxic/anti-proliferative activity at 24 h exposure (IC50 = 45-70 µg/mL, for Caco-2; IC50 = 60-80 µg/mL, for HepG2), whereas Zamorean absolute did not produce cytotoxicity (IC50 ≥ 200.00 µg/mL). Here we show, for the first time, that labdanum resin obtained by the Andalusian process, and its fractions, are composed of phytochemicals with anti-diabetic, neuroprotective and anti-proliferative potential, which are worth investigating for the pharmaceutical industry. However, toxic side-effects must also be addressed when using these products by ingestion, as done traditionally.


Subject(s)
Cistus , Hypoglycemic Agents , Neuroprotective Agents , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/chemistry , Neuroprotective Agents/pharmacology , Neuroprotective Agents/chemistry , Neuroprotective Agents/isolation & purification , Humans , Cistus/chemistry , Resins, Plant/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Cell Proliferation/drug effects , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Hep G2 Cells , Flavonoids/pharmacology , Flavonoids/chemistry , Flavonoids/isolation & purification
8.
Int J Biol Macromol ; 270(Pt 1): 132221, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38729499

ABSTRACT

Cellulose acetate (CA) is a non-toxic, renewable, and biodegradable polymeric material that can be effectively electrospuned into bacterial filtration efficient nanofiber membrane for face mask application. However, its fragile and non-antibacterial nature influenced its scalability. In this context, natural antibacterial gum rosin (GR) additive can be explored. Therefore, the present study aimed to produce a CA/GR composite nanofibers membrane for the finest bacterial filtration, excellent antibacterial moiety, and improved tensile properties for facemask application. Hence, in this work, we have studied the effect of GR concentrations (0-15 g) on the needleless electrospinning behavior and fibers' morphology through rheology, electrical conductivity, and SEM analysis. These analyses revealed that GR significantly affects the fibers' spinning behavior, morphology, and diameter of the produced fibers. Later, ATR-FTIR spectroscopy mapped the functional changes in the produced nanofibers that affirmed the integration of GR with CA polymer. This modification resulted in a 3-fold rise in tensile strength and an 11-fold decline in elongation% in 15 g CA/GR composite nanofibers membrane than the control sample. Furthermore, it has shown 98.79 ± 0.10% bacterial filtration efficiency and âˆ¼ 93 % reduction in Staphylococcus Aureus and Klebsiella Pneumoniae bacterial growth, elucidating a high-efficiency level for potential facemask application.


Subject(s)
Anti-Bacterial Agents , Bacteria , Cellulose , Masks , Nanofibers , Resins, Plant , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Electric Conductivity , Filtration/methods , Filtration/standards , Masks/microbiology , Masks/standards , Nanofibers/chemistry , Nanofibers/microbiology , Nanofibers/ultrastructure , Resins, Plant/chemistry , Rheology , Cellulose/analogs & derivatives , Cellulose/chemistry , Cellulose/pharmacology
9.
An Acad Bras Cienc ; 96(1): e20230859, 2024.
Article in English | MEDLINE | ID: mdl-38597501

ABSTRACT

This study aims to prepare oil-modified alkyd resins using a linseed oil/canola oil (LO/CO) blend and waste PET depolymerization product, suitable for environmentally friendly coating applications. Waste PET flakes obtained from grinding post-consumer water bottles were depolymerized by the aminoglycolysis reaction at high pressure. Raw depolymerization product (DP) was used in the synthesis of four components, 50% oil alkyd resins by monoglyceride method. DP has partly replaced the dibasic acid component in the PET-based alkyd formulations. Besides PET-based alkyds, reference alkyds without DP were also synthesized for comparison. Then, the surface coating properties and thermal behaviors of alkyd films were determined. The effect of DP usage and the changing ratios of LO/CO blend on coating properties and thermal behaviors of alkyd films were investigated. In addition, the optimum LO/CO blend ratio which is compatible with alkyd formulation was attempted to be determined. At the end of this study, glossy, soft/medium-hard films were obtained with excellent adhesion, impact strength, and chemical resistance. Thermal resistance and final thermal oxidative degradation temperature increased with adding DP to the alkyd formulation. Using LO/CO blend in the formulations affected oxidation rate and ratio, hence, drying time/degree and oxidative stability of alkyd films.


Subject(s)
Linseed Oil , Resins, Plant , Rapeseed Oil , Temperature , Surface Properties
10.
Molecules ; 29(7)2024 Apr 08.
Article in English | MEDLINE | ID: mdl-38611949

ABSTRACT

Olibanum is a resinous traditional Chinese medicine that is directly used as a powder. It is widely used in China and is often combined with other traditional Chinese medicine powders to promote blood circulation and relieve pain, as well as to treat rheumatism, rheumatoid arthritis, and osteoarthritis. Powdered traditional Chinese medicine is often easily contaminated by microorganisms and 60Co irradiation is one of the good sterilization methods. Volatile organic compounds (VOCs) are the main active ingredient of olibanum. The aim of this study was to validate the optimum doses of 60Co irradiation and its effect on VOCs. 60Co irradiation was applied in different doses of 0 kGy, 1.5 kGy, 3.0 kGy, and 6.0 kGy. Changes in VOCs were detected using gas chromatography ion mobility spectrometry. A total of 81 VOCs were identified. The odor fingerprint results showed that, with an increase in irradiation dose, most of the VOCs of olibanum changed. Through principal component analysis, cluster analysis, and partial least squares discriminant analysis, it was demonstrated that, at 1.5 kGy, the impact of radiation on the VOCs of olibanum was minimal, indicating this is a relatively good irradiation dose. This study provides a theoretical basis for the irradiation processing and quality control of resinous medicinal materials such as olibanum and it also provides a good reference for irradiation technology development and its application to functional foods, thus making it both significant from a research perspective and useful from an application perspective.


Subject(s)
Cobalt Radioisotopes , Frankincense , Volatile Organic Compounds , Ion Mobility Spectrometry , Gas Chromatography-Mass Spectrometry , Resins, Plant
11.
PLoS One ; 19(4): e0301103, 2024.
Article in English | MEDLINE | ID: mdl-38568980

ABSTRACT

Birch bark tar is the most widely documented adhesive in prehistoric Europe. More recent periods attest to a diversification in terms of the materials used as adhesives and their application. Some studies have shown that conifer resins and beeswax were added to produce compound adhesives. For the Iron Age, no comparative large-scale studies have been conducted to provide a wider perspective on adhesive technologies. To address this issue, we identify adhesive substances from the Iron Age in north-eastern France. We applied organic residue analysis to 65 samples from 16 archaeological sites. This included residues adhering to ceramics, from vessel surface coatings, repaired ceramics, vessel contents, and adhesive lumps. Our findings show that, even during the Iron Age in north-eastern France, birch bark tar is one of the best-preserved adhesive substances, used for at least 400 years. To a lesser extent, Pinaceae resin and beeswax were also identified. Through statistical analyses, we show that molecular composition differs in samples, correlating with adhesive function. This has implications for our understanding of birch bark tar production, processing and mode of use during the Iron Age in France and beyond.


Subject(s)
Adhesives , Dental Bonding , Adhesives/chemistry , Betula/chemistry , Resins, Plant , Archaeology , Technology , Materials Testing , Resin Cements/chemistry , Composite Resins/chemistry
12.
Eur J Pharmacol ; 971: 176552, 2024 May 15.
Article in English | MEDLINE | ID: mdl-38580181

ABSTRACT

AIM OF THE STUDY: Chronic cholestasis leads to liver fibrosis, which lacks effective treatment. In this study, we investigated the role and mechanisms of action of loureirin B (LB) in cholestatic liver fibrosis. MATERIALS AND METHODS: Bile duct ligation (BDL)-induced hepatic fibrosis mice were used as in vivo models. Transforming growth factor-ß1 (TGF-ß1)-pretreated HSC-T6 cells were used to explore the mechanism by which LB attenuates liver fibrosis in vitro. RNA sequencing, quantitative PCR (qPCR), western blotting, immunohistochemistry and immunofluorescence were performed to detect the fibrosis markers and measure autophagy levels. Flow cytometry, cell counting kit-8 (CCK-8) assay, and 5'-ethynyl-2'-deoxyuridine (EdU) assay were conducted to detect cell proliferation and viability. GFP-RFP-LC3 adenovirus, autophagy-related protein 7 (ATG7) siRNA, and bafilomycin A1 (BafA1) were used to verify autophagic flux. RESULTS: Our results showed that LB ameliorates liver injury, inhibits collagen deposition, and decreases the expressions of fibrosis-related markers in BDL-induced mouse livers. In vitro, we found that LB inhibited proliferation and migration, promoted apoptosis, and inhibited the activation of HSC-T6 cells pretreated with TGF-ß1. RNA sequencing analysis of HSC-T6 cells showed that LB treatment predominantly targeted autophagy-related pathways. Further protein analysis indicated that LB downregulated the expression of phosphorylated AKT (p-AKT) and phosphorylated mTOR (p-mTOR), and upregulated LC3-II, p62, and ATG7 both in vivo and in vitro. Intriguingly, ATG7 inactivation reversed the antifibrotic effects of LB on HSC-T6 cells. CONCLUSIONS: LB can improve BDL-induced liver fibrosis by inhibiting the activation and proliferation of HSCs and is expected to be a promising antifibrotic drug.


Subject(s)
Cholestasis , Proto-Oncogene Proteins c-akt , Resins, Plant , Mice , Animals , Proto-Oncogene Proteins c-akt/metabolism , Signal Transduction , Transforming Growth Factor beta1/metabolism , Hepatic Stellate Cells , Liver Cirrhosis/chemically induced , TOR Serine-Threonine Kinases/metabolism , Liver/metabolism , Autophagy , Cholestasis/pathology
13.
PLoS One ; 19(4): e0301528, 2024.
Article in English | MEDLINE | ID: mdl-38635694

ABSTRACT

An inexpensive and high-performing solid Coumarone resin was added to Styrene-butadiene-styrene (SBS) copolymer-modified asphalt to enhance its storage stability and road performance. To assess the effect of Coumarone resin dosage on the SBS-modified asphalt, a series of laboratory tests were conducted. The composite modified asphalt's segregation test was used to evaluate its storage stability, Dynamic Shear Rheometer (DSR) and Multiple Stress Creep Recovery (MSCR) tests were employed to investigate its high-temperature performance and permanent deformation resistance, and the Bending Beam Rheology (BBR) test was utilized to measure its low-temperature performance. Fluorescence microscopy was used to observe the composite modified asphalt's microstructure, and Fourier Transform Infrared Spectroscopy (FTIR) was conducted to study the changes in chemical structure during the modification process. The results showed that Coumarone resin can improve the compatibility of SBS and asphalt, improve the high-temperature performance and deformation resistance of SBS-modified asphalt, and adding an appropriate amount of Coumarone resin can help enhance the low-temperature cracking resistance of modified asphalt. The optimal dosage of Coumarone resin recommended for SBS-modified asphalt performance enhancement is 2% under the test conditions, as determined by comparing the test results of samples with various dosages.


Subject(s)
Benzofurans , Hydrocarbons , Styrene , Cold Temperature , Resins, Plant
14.
Molecules ; 29(8)2024 Apr 13.
Article in English | MEDLINE | ID: mdl-38675598

ABSTRACT

Plant extracts and essential oils can be alternative environmentally friendly agents to combat pathogenic microbes and malaria vectors. Myrrh is an aromatic oligum resin that is extracted from the stem of Commiphora spp. It is used in medicine as an insecticide, cytotoxic, and aromatic. The current study assessed the effect of Commiphora myrrha resin extracts on the biological potency of the third larval stage of Aedes aegypti, as well as its antioxidant and cytotoxic properties against two types of tumor cells (HepG-2 and Hela cell lines). It also used GC-MS to determine the chemical composition of the C. myrrha resin extracts. Fifty components from the extracted plant were tentatively identified using the GC-MS method, with curzerene (33.57%) typically listed as the primary ingredient, but other compounds also make up a significant portion of the mixture, including 1-Methoxy-3,4,5,7-tetramethylnaphthalene (15.50%), ß-Elemene (5.80%), 2-Methoxyfuranodiene (5.42%), 2-Isopropyl-4,7-Dimethyl-1-Naphthol (4.71%), and germacrene B (4.35%). The resin extracts obtained from C. myrrha exhibited significant efficacy in DPPH antioxidant activity, as evidenced by an IC50 value of 26.86 mg/L and a radical scavenging activity percentage of 75.06%. The 50% methanol extract derived from C. myrrha resins exhibited heightened potential for anticancer activity. It demonstrated substantial cytotoxicity against HepG-2 and Hela cells, with IC50 values of 39.73 and 29.41 µg mL-1, respectively. Notably, the extract showed non-cytotoxic activity against WI-38 normal cells, with an IC50 value exceeding 100 µg mL-1. Moreover, the selectivity index for HepG-2 cancer cells (2.52) was lower compared to Hela cancer cells (3.40). Additionally, MeOH resin extracts were more efficient against the different growth stages of the mosquito A. aegypti, with lower LC50, LC90, and LC95 values of 251.83, 923.76, and 1293.35 mg/L, respectively. In comparison to untreated groups (1454 eggs/10 females), the average daily number of eggs deposited (424 eggs/L) decreases at higher doses (1000 mg/L). Finally, we advise continued study into the possible use of C. myrrha resins against additional pests that have medical and veterinary value, and novel chemicals from this extract should be isolated and purified for use in medicines.


Subject(s)
Antioxidants , Commiphora , Gas Chromatography-Mass Spectrometry , Larva , Plant Extracts , Resins, Plant , Commiphora/chemistry , Humans , Gas Chromatography-Mass Spectrometry/methods , Antioxidants/pharmacology , Antioxidants/chemistry , Animals , Plant Extracts/pharmacology , Plant Extracts/chemistry , HeLa Cells , Resins, Plant/chemistry , Larva/drug effects , Hep G2 Cells , Insecticides/pharmacology , Insecticides/chemistry , Insecticides/isolation & purification , Aedes/drug effects , Cell Survival/drug effects
15.
Molecules ; 29(7)2024 Mar 22.
Article in English | MEDLINE | ID: mdl-38611709

ABSTRACT

Solid-phase peptide synthesis (SPPS) is the preferred strategy for synthesizing most peptides for research purposes and on a multi-kilogram scale. One key to the success of SPPS is the continual evolution and improvement of the original method proposed by Merrifield. Over the years, this approach has been enhanced with the introduction of new solid supports, protecting groups for amino acids, coupling reagents, and other tools. One of these improvements is the use of the so-called "safety-catch" linkers/resins. The linker is understood as the moiety that links the peptide to the solid support and protects the C-terminal carboxylic group. The "safety-catch" concept relies on linkers that are totally stable under the conditions needed for both α-amino and side-chain deprotection that, at the end of synthesis, can be made labile to one of those conditions by a simple chemical reaction (e.g., an alkylation). This unique characteristic enables the simultaneous use of two primary protecting strategies: tert-butoxycarbonyl (Boc) and fluorenylmethoxycarbonyl (Fmoc). Ultimately, at the end of synthesis, either acids (which are incompatible with Boc) or bases (which are incompatible with Fmoc) can be employed to cleave the peptide from the resin. This review focuses on the most significant "safety-catch" linkers.


Subject(s)
Antifibrinolytic Agents , Solid-Phase Synthesis Techniques , Alkylation , Amino Acids , Resins, Plant , Peptides
16.
Int J Biol Macromol ; 265(Pt 2): 130569, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38553394

ABSTRACT

The development of equipped bio-based epoxy materials has been gaining much attention recently. Nevertheless, finding the balance between the structure and properties of materials remains a significant challenge. In this work, cellulose-based epoxy (PHPCEP) with "soft" and "hard" cooperative structures was designed and demonstrated to endow bisphenol A diglycidyl ether (BADGE) with excellent toughness, heat resistance, mechanical strength, glass transition temperature, thermal stability, and solvent resistance. When 5 wt% PHPCEP was incorporated into BADGE composites, the resulting materials exhibited the maximum flexural strength (121.9 MPa) and tensile strength (71.4 MPa), a high glass transition temperature (148.3 °C), and 10 wt% PHPCEP/BADGE demonstrated the highest impact strength (70.5 kJ/m2). These figures are 18.8 %, 16.1 %, 21.5 %, and 254.3 % higher than the corresponding values of neat BADGE. The results of dynamic mechanical properties and heat degradation of the cured specimens also suggest that PHPCEP/BADGE materials have superior stiffness and toughness than neat BADGE, which could be attributed to the strong interaction between PHPCEP and BADGE, delivering better thermal stability for the composites compared to the pristine resin. Considering the remarkable effect, this work provides an effective way of highly efficient utilization of abundant cellulose and a high-performance additive for composite materials.


Subject(s)
Cellulose , Epoxy Compounds , Cellulose/chemistry , Tensile Strength , Epoxy Compounds/chemistry , Benzhydryl Compounds , Resins, Plant
17.
BMC Oral Health ; 24(1): 352, 2024 Mar 19.
Article in English | MEDLINE | ID: mdl-38504287

ABSTRACT

BACKGROUND: AH Plus, an epoxy resin-based sealer, is widely used in endodontic practice, owing to its good physical properties that confers longstanding dimensional stability and good adhesion to dentin. Nevertheless, its propensity to trigger inflammation, especially in its freshly mixed state, has been extensively documented. Phytochemicals such as Petasin, Pachymic acid, Curcumin, and Shilajit are known for their anti-inflammatory and analgesic effects. This study aimed to analyze and determine the effect of these natural products on the physical properties of AH Plus sealer when incorporated with the sealer. METHODS: AH Plus (AHR) sealer was mixed with 10% petasin, 0.75% pachymic, 0.5% and 6%shilajit to obtain AHP, AHA, AHC and AHS in the ratio of 10:1 and 5:1 respectively. Five samples of each material were assessed for setting time, solubility, flow, and dimensional stability in accordance with the ISO 6876:2012 standardization. Sealers were characterized through scanning electron microscopy (SEM), X-ray energy dispersive spectroscopy, X-ray diffraction (XRD), and Fourier transform infrared (FTIR) spectroscopy. Statistical evaluation involved the Kolmogorov-Smirnov and Shapiro-Wilks tests for normality and the one-way ANOVA test for analysis. RESULTS: In this investigation, the characterisation analysis revealed a relatively similar microstructure in all the experimental root canal sealers. All experimental groups, excluding the control group, exhibited an increase in flow ranging from 11.9 to 31.4% at a 10:1 ratio. Similarly, for the 5:1 ratio, the increase ranged from 12.02 to 31.83%. In terms of dimensional stability, all groups at the 10:1 ratio showed a decrease compared to the control group. The addition of natural agents to AHR in 10:1 ratio led to a reduction in setting time by 8.9-31.6%, and at a 5:1 ratio, the reduction ranged from 8.1 to 31.5%. However, regarding solubility, the addition of natural agents did not induce any significant alterations. CONCLUSION: Based on the results of this study, it can be concluded that all tested root canal sealers exhibited properties that met the acceptable criteria outlined in the ISO 6876:2012 standardization.


Subject(s)
Curcumin , Minerals , Resins, Plant , Root Canal Filling Materials , Sesquiterpenes , Triterpenes , Humans , Root Canal Filling Materials/chemistry , Curcumin/pharmacology , Epoxy Resins , Materials Testing , Silicates/chemistry , Calcium Compounds/chemistry
18.
Phytochemistry ; 222: 114060, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38522560

ABSTRACT

Natural rubber produced in stems of the guayule plant (Parthenium argentatum) is susceptible to post-harvest degradation from microbial or thermo-oxidative processes, especially once stems are chipped. As a result, the time from harvest to extraction must be minimized to recover high quality rubber, especially in warm summer months. Tocopherols are natural antioxidants produced in plants through the shikimate and methyl-erythtiol-4-phosphate (MEP) pathways. We hypothesized that increased in vivo guayule tocopherol content might protect rubber from post-harvest degradation, and/or allow reduced use of chemical antioxidants during the extraction process. With the objective of enhancing tocopherol content in guayule, we overexpressed four Arabidopsis thaliana tocopherol pathway genes in AZ-2 guayule via Agrobacterium-mediated transformation. Tocopherol content was increased in leaf and stem tissues of most transgenic lines, and some improvement in thermo-oxidative stability was observed. Overexpression of the four tocopherol biosynthesis enzymes, however, altered other isoprenoid pathways resulting in reduced rubber, resin and argentatins content in guayule stems. The latter molecules are mainly synthesized from precursors derived from the mevalonate (MVA) pathway. Our results suggest the existence of crosstalk between the MEP and MVA pathways in guayule and the possibility that carbon metabolism through the MEP pathway impacts rubber biosynthesis.


Subject(s)
Asteraceae , Plant Leaves , Plant Stems , Tocopherols , Tocopherols/metabolism , Tocopherols/chemistry , Plant Leaves/metabolism , Plant Leaves/chemistry , Plant Stems/metabolism , Plant Stems/chemistry , Plant Stems/genetics , Asteraceae/metabolism , Asteraceae/chemistry , Asteraceae/genetics , Rubber/metabolism , Rubber/chemistry , Arabidopsis/metabolism , Arabidopsis/genetics , Arabidopsis/chemistry , Resins, Plant/metabolism , Resins, Plant/chemistry
19.
J Nat Med ; 78(3): 525-536, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38457082

ABSTRACT

Ipomoea muricata (L.) Jacq. seeds (Convolvulaceae) are used as a traditional laxative and carminative medicine. Muricatins XIV (1), XV (2), XVI (3), and XVII (4), were isolated from I. muricata seeds as four new resin glycosides, along with seven known compounds, three of which were isolated for the first time as natural products; their structures were determined using MS and NMR spectroscopy. Compounds 1-4 are macrolactones (jalapins); the sugar moieties of 1, 2, and 4 are partially acylated with 2S-methylbutyric acid, while that of 3 is esterified with 2S-methylbutyric and 2S-methyl-3S-hydroxybutyric acids. In addition, the antiviral activities of the seven compounds obtained in this study, together with five known compounds obtained in our previous study into resin glycosides from I. muricata seeds, were evaluated against herpes simplex virus type 1 (HSV-1); their cytotoxicities against HL-60 human promyelocytic leukemia cells were also investigated. All examined jalapins exhibited similar or slightly weaker anti-HSV-1 activities than acyclovir, the positive control; however, the glycosidic acid of 4 was inactive, while its methyl ester was weakly active. On the other hand, cytotoxicity testing against HL-60 cells showed similar results to those observed during anti-HSV-1 activity testing, with the exception that one jalapin was less active.


Subject(s)
Antiviral Agents , Glycosides , Ipomoea , Resins, Plant , Seeds , Ipomoea/chemistry , Seeds/chemistry , Glycosides/pharmacology , Glycosides/chemistry , Glycosides/isolation & purification , Humans , Resins, Plant/chemistry , Antiviral Agents/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Molecular Structure , Herpesvirus 1, Human/drug effects , HL-60 Cells , Plant Extracts/chemistry , Plant Extracts/pharmacology , Magnetic Resonance Spectroscopy
20.
Chem Biodivers ; 21(5): e202400185, 2024 May.
Article in English | MEDLINE | ID: mdl-38513004

ABSTRACT

The resin essential oil (REO) of the Tunisian Araucaria heterophylla trunk bark was investigated for its chemical composition. Then, it was evaluated for its insecticidal and allelopathic activities. The REO was obtained by hydrodistillation for 9 h (yield of 4.2 % w/w). Moreover, fractional hydrodistillation was carried out at 3-hour intervals, resulting in 3 fractions (R1-R3), to facilitate chemical identification and localization of the aforementioned biological activities. GC/MS analysis of the obtained samples allowed the identification of 25 compounds, representing between 91.2 and 96.3 % of their total constituents, which consisted predominantly of sesquiterpene hydrocarbons, oxygenated sesquiterpenes and diterpene hydrocarbons. α-Copaene (10.8 %), γ-muurolene (5.8 %), α-copaen-11-ol (7.8 %), spathulenol (10.5 %), 15-copaenol (8.2 %), ylangenal (10.3 %), dehydrosaussurea lactone (7.7 %), and sandaracopimaradiene (11.4 %) were identified as major compounds. The second part aimed to assess the impact of the A. heterophylla EO and its three fractions for their insecticidal and repellent activity against Tribolium castaneum (Herbst), a stored grain pest, of which a strong repellent activity was noted. In addition, the studied samples showed high phytotoxic effects against Lactuca sativa. The third fraction (R3) performed a total inhibitory potential on seed germination and seedling growth of the target plant. Furthermore, alongside this discovery, an estimation was conducted through molecular docking analysis. Wherein the main compounds of the studied samples were docked into the active pocket of protoporphyrinogen IX oxidase (PDB: 1SEZ), a key enzyme in chlorophyll biosynthesis. Thus, it is recommended to use the REO of A. heterophylla as a natural herbicide.


Subject(s)
Araucaria , Insecticides , Oils, Volatile , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Oils, Volatile/isolation & purification , Tunisia , Animals , Insecticides/pharmacology , Insecticides/chemistry , Insecticides/isolation & purification , Araucaria/drug effects , Araucaria/chemistry , Araucaria/metabolism , Insect Repellents/pharmacology , Insect Repellents/chemistry , Insect Repellents/isolation & purification , Resins, Plant/chemistry , Molecular Docking Simulation , Gas Chromatography-Mass Spectrometry
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