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1.
Open Vet J ; 14(4): 1043-1050, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38808285

ABSTRACT

Background: Dengue infection can trigger an immunological response that results in an inflammatory reaction, which acts as a defensive mechanism to protect the host. Dengue infection leads to an elevation in the release of pro-inflammatory cytokines, including tumor necrosis factor-α (TNF-α), interleukin-1ß (IL-1ß), and interleukin-6 (IL-6). These three cytokines have been shown to correlate with the development of thrombocytopenia and plasma leakage, which is related to the severity of the disease. Aim: This study aims to investigate the effect of faloak (Sterculia quadrifida R. Br) stem bark on TNF-α, IL-1ß, and IL-6 levels in Wistar rats infected with dengue, specifically DENV-3. Methods: A group of 27 male Wistar rats (Rattus norvegicus) aged 2-3 months and weighting 200-300 g were divided into three distinct groups: healthy, dengue, and treatment (dengue infection and extract) groups. The rats in both the dengue and treatment groups were administered an injection of DENV-3 with a titer of 105 pfu at a dosage of 0.8 cc via the intraperitoneal route. The propagation of DENV-3 was initiated using C6/36 cells, and it underwent four passages. The extract was administered orally via a nasogastric tube at a dosage of 1,500 mg/kg body weight once daily for 7 days. The healthy group underwent blood sampling on the first day, whereas the dengue and therapy groups underwent blood sampling on the fifth and eighth, respectively. Results: Compared with the healthy group, TNF-α levels in the dengue and treatment groups showed significant differences on day 5 post-infection. The post hoc analysis revealed a statistically significant difference between the dengue-treatment and dengue-healthy groups. The IL-1ß levels in the dengue and healthy groups significantly differed on days 5 and 8 post-infection compared to the healthy group. The treatment group had less of a decrease in IL-6 levels on days 5 and 8 than the dengue group. However, no statistically significant differences were observed. Conclusion: The stem bark of S. quadrifida shows potential as an anti-inflammatory agent in dengue infections, particularly in its ability to decrease levels of TNF-α and IL-1ß.


Subject(s)
Anti-Inflammatory Agents , Dengue , Interleukin-6 , Plant Bark , Plant Extracts , Rats, Wistar , Tumor Necrosis Factor-alpha , Animals , Male , Rats , Plant Bark/chemistry , Tumor Necrosis Factor-alpha/blood , Dengue/veterinary , Dengue/drug therapy , Plant Extracts/pharmacology , Plant Extracts/therapeutic use , Plant Extracts/administration & dosage , Interleukin-6/blood , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Interleukin-1beta/blood , Dengue Virus/drug effects , Dengue Virus/physiology
2.
J Toxicol Environ Health A ; 87(16): 662-673, 2024 Aug 17.
Article in English | MEDLINE | ID: mdl-38808737

ABSTRACT

Pseudobombax marginatum, popularly known as "embiratanha," is widely used by traditional communities as anti-inflammatory and analgesic agent. This study aimed to determine the phytochemical profile as well as cytotoxicity, acute oral toxicity, genotoxicity, and mutagenicity attributed to exposure to aqueous (AqEx) and ethanolic (EtEx) extracts of embiratanha bark. Phytochemical screening was conducted using thin-layer chromatography (TLC). Cell viability was analyzed using MTT assay with human mammary gland adenocarcinoma (MDA-MB-231) and macrophage (J774A.1) cell lines, exposed to concentrations of 12.5, 25, 50, or 100 µg/ml of either extract. For acute oral toxicity, comet assay and micronucleus (MN) tests, a single dose of 2,000 mg/kg of either extract was administered orally to Wistar rats. TLC analysis identified classes of metabolites in the extracts, including cinnamic acid derivatives, flavonoids, hydrolyzable tannins, condensed tannins, coumarins, and terpenes/steroids. In the cytotoxicity assay, the varying concentrations of extracts derived from embiratanha induced no significant alterations in the viability of MDA-MB-231 cells. The lowest concentration of EtEx significantly increased macrophage J774A.1 viability. However, the higher concentrations of AqEx markedly lowered macrophage J774A.1 viability. Animals exhibited no toxicity in the parameters analyzed in acute oral toxicity, comet assay, and MN tests. Further, EtEx promoted a significant reduction in DNA damage index and DNA damage frequency utilizing the comet assay, while the group treated with AqEx exhibited no marked differences. Thus, data demonstrated that AqEx or EtEx of embiratanha may be considered safe at a dose of 2,000 mg/kg orgally under our experimental conditions tested.


Subject(s)
Plant Extracts , Rats, Wistar , Plant Extracts/toxicity , Plant Extracts/chemistry , Animals , Humans , Rats , Cell Line, Tumor , Male , Comet Assay , Micronucleus Tests , Female , Cell Survival/drug effects , Phytochemicals/toxicity , Phytochemicals/analysis , Mice , Plant Bark/chemistry , Mutagens/toxicity , Mutagenicity Tests , Ethanol/chemistry
3.
Molecules ; 29(9)2024 Apr 29.
Article in English | MEDLINE | ID: mdl-38731544

ABSTRACT

Berberis vulgaris (L.) has remarkable ethnopharmacological properties and is widely used in traditional medicine. The present study investigated B. vulgaris stem bark (Berberidis cortex) by extraction with 50% ethanol. The main secondary metabolites were quantified, resulting in a polyphenols content of 17.6780 ± 3.9320 mg Eq tannic acid/100 g extract, phenolic acids amount of 3.3886 ± 0.3481 mg Eq chlorogenic acid/100 g extract and 78.95 µg/g berberine. The dried hydro-ethanolic extract (BVE) was thoroughly analyzed using Ultra-High-Performance Liquid Chromatography coupled with High-Resolution Mass Spectrometry (UHPLC-HRMS/MS) and HPLC, and 40 bioactive phenolic constituents were identified. Then, the antioxidant potential of BVE was evaluated using three methods. Our results could explain the protective effects of Berberidis cortex EC50FRAP = 0.1398 mg/mL, IC50ABTS = 0.0442 mg/mL, IC50DPPH = 0.2610 mg/mL compared to ascorbic acid (IC50 = 0.0165 mg/mL). Next, the acute toxicity and teratogenicity of BVE and berberine-berberine sulfate hydrate (BS)-investigated on Daphnia sp. revealed significant BS toxicity after 24 h, while BVE revealed considerable toxicity after 48 h and induced embryonic developmental delays. Finally, the anticancer effects of BVE and BS were evaluated in different tumor cell lines after 24 and 48 h of treatments. The MTS assay evidenced dose- and time-dependent antiproliferative activity, which was higher for BS than BVE. The strongest diminution of tumor cell viability was recorded in the breast (MDA-MB-231), colon (LoVo) cancer, and OSCC (PE/CA-PJ49) cell lines after 48 h of exposure (IC50 < 100 µg/mL). However, no cytotoxicity was reported in the normal epithelial cells (HUVEC) and hepatocellular carcinoma (HT-29) cell lines. Extensive data analysis supports our results, showing a significant correlation between the BVE concentration, phenolic compounds content, antioxidant activity, exposure time, and the viability rate of various normal cells and cancer cell lines.


Subject(s)
Antioxidants , Berberis , Plant Bark , Plant Extracts , Berberis/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Antioxidants/pharmacology , Antioxidants/chemistry , Plant Bark/chemistry , Humans , Cell Line, Tumor , Animals , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Cell Survival/drug effects , Phenols/pharmacology , Phenols/chemistry , Chromatography, High Pressure Liquid , Plant Stems/chemistry
4.
Bioresour Technol ; 402: 130768, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38697367

ABSTRACT

The bark represents the outer protective layer of trees. It contains high concentrations of antimicrobial extractives, in addition to regular wood polymers. It represents a huge underutilized side stream in forestry, but biotechnological valorization is hampered by a lack of knowledge on microbial bark degradation. Many fungi are efficient lignocellulose degraders, and here, spruce bark degradation by five species, Dichomitus squalens, Rhodonia placenta, Penicillium crustosum, Trichoderma sp. B1, and Trichoderma reesei, was mapped, by continuously analyzing chemical changes in the bark over six months. The study reveals how fungi from different phyla degrade bark using diverse strategies, regarding both wood polymers and extractives, where toxic resin acids were degraded by Basidiomycetes but unmodified/tolerated by Ascomycetes. Proteome analyses of the white-rot D. squalens revealed several proteins, with both known and unknown functions, that were specifically upregulated during growth on bark. This knowledge can accelerate improved utilization of an abundant renewable resource.


Subject(s)
Picea , Plant Bark , Polysaccharides , Picea/microbiology , Plant Bark/chemistry , Polysaccharides/metabolism , Fungi/metabolism , Lignin/metabolism , Biodegradation, Environmental , Fungal Proteins/metabolism
5.
Phytochemistry ; 223: 114139, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38750707

ABSTRACT

Eleven undescribed isoquinoline alkaloids (1-8, 14, 15, and 24), along with 19 analogues (9-13, 16-23, and 25-30) were isolated from the barks of Alangium salviifolium. The structures of the undescribed compounds were elucidated through the analysis of their HR-ESI-MS, 1D and 2D NMR, IR, UV, and X-ray diffraction. The absolute configuration of 8 was established via the ECD calculation. Notably, compounds 1/2 and 3/4 were two pairs of C-14 epimers. The isolated alkaloids were evaluated for their cytotoxicity against various cancer cell lines, including SGC-7901, HeLa, K562, A549, BEL-7402, HepG2, and B16, ß-carboline-benzoquinolizidine (14-22) and cepheline-type (24-28) alkaloids exhibited remarkable cytotoxicity, with IC50 values ranging from 0.01 to 48.12 µM. Remarkably, compounds 17 and 21 demonstrated greater cytotoxicity than the positive control doxorubicin hydrochloride. Furthermore, a significant proportion of these bioactive alkaloids possess a C-1' epimer configuration. The exploration of their structure-activity relationship holds promise for directing future investigations into alkaloids derived from Alangium, potentially leading to novel insights and therapeutic advancements.


Subject(s)
Alkaloids , Antineoplastic Agents, Phytogenic , Drug Screening Assays, Antitumor , Isoquinolines , Plant Bark , Humans , Alkaloids/chemistry , Alkaloids/pharmacology , Alkaloids/isolation & purification , Plant Bark/chemistry , Isoquinolines/chemistry , Isoquinolines/pharmacology , Isoquinolines/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Molecular Structure , Structure-Activity Relationship , Cell Line, Tumor , Alangiaceae/chemistry , Cell Proliferation/drug effects , Dose-Response Relationship, Drug
6.
BMC Plant Biol ; 24(1): 383, 2024 May 09.
Article in English | MEDLINE | ID: mdl-38724888

ABSTRACT

Taxus chinensis (Taxus cuspidata Sieb. et Zucc.) is a traditional medicinal plant known for its anticancer substance paclitaxel, and its growth age is also an important factor affecting its medicinal value. However, how age affects the physiological and metabolic characteristics and active substances of T. chinensis is still unclear. In this study, carbon and nitrogen accumulation, contents of active substances and changes in primary metabolites in barks and annual leaves of T. chinensis of different diameter classes were investigated by using diameter classes instead of age. The results showed that leaves and barks of small diameter class (D1) had higher content of non-structural carbohydrates and C, which were effective in enhancing defense capacity, while N content was higher in medium (D2) and large diameter classes (D3). Active substances such as paclitaxel, baccatin III and cephalomannine also accumulated significantly in barks of large diameter classes. Moreover, 21 and 25 differential metabolites were identified in leaves and barks of different diameter classes, respectively. The differential metabolites were enhanced the TCA cycle and amino acid biosynthesis, accumulate metabolites such as organic acids, and promote the synthesis and accumulation of active substances such as paclitaxel in the medium and large diameter classes. These results revealed the carbon and nitrogen allocation mechanism of different diameter classes of T. chinensis, and its relationship with medicinal components, providing a guidance for the harvesting and utilization of wild T. chinensis.


Subject(s)
Carbon , Metabolomics , Nitrogen , Plant Leaves , Taxus , Taxus/metabolism , Nitrogen/metabolism , Carbon/metabolism , Plant Leaves/metabolism , Plant Bark/metabolism , Plant Bark/chemistry
7.
Fitoterapia ; 175: 105955, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38604259

ABSTRACT

Brucea javanica, a valued traditional medicinal plant in Malaysia, known for its fever-treating properties yet remains underexplored for its potential antiviral properties against dengue. This study aims to simultaneously identify chemical classes and metabolites within B. javanica using molecular networking (MN), by Global Natural Product Social (GNPS), and SIRIUS in silico annotation. Liquid chromatography-mass spectrometry (LC-MS2)-based MN explores chemical diversity across four plant parts (leaves, roots, fruits, and stem bark), revealing diverse metabolites such as tryptophan-derived alkaloids, terpenoids, and octadecadenoids. Simultaneous LC-MS2 and MN analyses reveal a discriminative capacity for individual plant components, with roots accumulating tryptophan alkaloids, fruits concentrating quassinoids, leaves containing fusidanes, and stem bark primarily characterised by simple indoles. Subsequently, extracts were evaluated for dengue antiviral activity using adenosine triphosphate (ATP) and plaque assays, indicates potent efficacy in the dichloromethane (DCM) extract from roots (EC50 = 0.3 µg/mL, SI = 10). Molecular docking analysis of two major compounds; canthin-6-one (264) and 1-hydroxy-11-methoxycanthin-6-one (275) showed potential binding interactions with active sites of NS5 RNA-dependent RNA polymerase (RdRp) of dengue virus (DENV) protein. Subsequent in vitro evaluation revealed compounds 264 and 275 had a promising dengue antiviral activity with SI value of 63 and 1.85. These identified metabolites emerge as potential candidates for further evaluation in dengue antiviral activities.


Subject(s)
Antiviral Agents , Brucea , Dengue Virus , Molecular Docking Simulation , Phytochemicals , Dengue Virus/drug effects , Antiviral Agents/pharmacology , Antiviral Agents/isolation & purification , Antiviral Agents/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Brucea/chemistry , Malaysia , Molecular Structure , Plant Extracts/pharmacology , Plant Extracts/chemistry , Plant Roots/chemistry , Plant Leaves/chemistry , Plant Bark/chemistry , Mass Spectrometry , Fruit/chemistry , Plants, Medicinal/chemistry , Network Pharmacology
8.
Bioresour Technol ; 400: 130698, 2024 May.
Article in English | MEDLINE | ID: mdl-38615967

ABSTRACT

The growing textile industry produces large volumes of hazardous wastewater containing dyes, which stresses the need for cheap, efficient adsorbing technologies. This study investigates a novel preprocessing method for producing activated carbons from abundantly available softwood bark. The preprocessing involved a continuous steam explosion preconditioning step, chemical activation with ZnCl2, pyrolysis at 600 and 800 °C, and washing. The activated carbons were subsequently characterized by SEM, XPS, Raman and FTIR prior to evaluation for their effectiveness in adsorbing reactive orange 16 and two synthetic dyehouse effluents. Results showed that the steam-exploded carbon, pyrolyzed at 600 °C, obtained the highest BET specific surface area (1308 m2/g), the best Langmuir maximum adsorption of reactive orange 16 (218 mg g-1) and synthetic dyehouse effluents (>70 % removal) of the tested carbons. Finally, steam explosion preconditioning could open up new and potentially more sustainable process routes for producing functionalized active carbons.


Subject(s)
Azo Compounds , Charcoal , Plant Bark , Steam , Adsorption , Plant Bark/chemistry , Azo Compounds/chemistry , Charcoal/chemistry , Coloring Agents/chemistry , Carbon/chemistry , Spectroscopy, Fourier Transform Infrared , Water Purification/methods , Water Pollutants, Chemical , Wastewater/chemistry , Spectrum Analysis, Raman
9.
Environ Sci Pollut Res Int ; 31(21): 31414-31423, 2024 May.
Article in English | MEDLINE | ID: mdl-38632195

ABSTRACT

Growing concern about the environmental effects of metal mordants and synthetic dyes is encouraging the use of bio-mordants and natural colorants. Cinnamon bark is a rich source of natural colorants such as cinnamaldehyde and tannins. The main purpose of this research was to study and compare the effect of bio-mordants versus metal mordants in terms of colorimetric parameters and color fastness properties of cinnamon bark on wool fibers. Accordingly, some bio-mordants, including date kernel, peppermint, banana peel, and artemisia, as well as some metal mordants like aluminum potassium sulphate and copper sulphate, were studied based on three conventional mordanting methods (pre-, meta-, and post-mordanting). The results indicated that the conjunction of metal mordants and polyphenolic bio-mordants with cinnamon colorants can create different hues and tones of brown. Also, the color produced by cinnamon in wool fibers has poor color fastness and low color strength. Overall, bio-mordants have presented good color properties, making the dyeing process eco-friendly and greener. Among the applied bio-mordants, peppermint has created the best color strength and color fastness.


Subject(s)
Cinnamomum zeylanicum , Coloring Agents , Cinnamomum zeylanicum/chemistry , Coloring Agents/chemistry , Animals , Wool Fiber , Plant Bark/chemistry , Metals/chemistry
10.
Phytomedicine ; 129: 155651, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38688144

ABSTRACT

BACKGROUND: Cinnamomum cassia Presl, a traditional Chinese medicine recorded in "Shennong's Herbal Classic," has been historically used to treat respiratory diseases and is employed to address inflammation. The essential oil derived from Cinnamomum cassia bark is a primary anti-inflammatory agent. However, there remains ambiguity regarding the chemical composition of cinnamon bark essential oil (BCEO), its principal anti-inflammatory components, and their potential efficacy in typical inflammatory respiratory conditions, such as acute lung injury (ALI). PURPOSE: This study aimed to unveil the chemical composition of BCEO. In addition, the mechanism of action of BCEO in ameliorating ALI and regulating macrophage polarization through the TLR4/MyD88/NF-κB pathway was elucidated. METHODS: BCEO was extracted using supercritical fluid extraction (SFE) and characterized through gas chromatography-mass spectrometry (GC-MS) analysis. Acute oral toxicity was observed in C57BL/6 J mice. The pharmacological effects and underlying mechanisms of BCEO were evaluated in a mouse model of ALI, which was induced by administering 5 mg/kg of lipopolysaccharide (LPS) through intratracheal instillation. RESULTS: GC-MS analysis revealed 99.08% of the constituents of BCEO. The primary components of BCEO were trans-cinnamaldehyde, o-methoxycinnamaldehyde, (+)-α-muurolene, δ-cadinene, and copaene. Oral acute toxicity tests indicated that the maximum tolerated dose of BCEO was 12 g/kg/day. BCEO treatment significantly reduced lung W/D ratio, total protein concentration in BALF, levels of TNF-α, IL-6, and IL-1ß in BALF, WBC count and NEU% in peripheral blood, and lung histological damage. Pulmonary function, IL-10 levels, and LYM% in peripheral blood also showed improvement. BCEO effectively decreased the proportion of M1 phenotype macrophages in BALF, M1/M2 ratio, and apoptotic cells in the lung tissue while increasing the proportion of M2 phenotype macrophages in BALF. Furthermore, BCEO treatment led to reduced protein and mRNA levels of TLR4, MyD88, and p-p65, alongside increased p65 expression, suggesting its potential to impede the TLR4/MyD88/NF-κB signaling pathway. CONCLUSION: SFE-extracted BCEO or its major constituents could serve as a viable treatment for ALI by reducing lung inflammation, improving pulmonary function, and protecting against LPS-induced ALI in mice. This therapeutic effect is achieved by inhibiting M1 macrophage polarization, promoting M2 macrophage polarization, and suppressing the TLR4/MyD88/NF-κB signaling pathway.


Subject(s)
Acute Lung Injury , Anti-Inflammatory Agents , Cinnamomum aromaticum , Lipopolysaccharides , Macrophages , Mice, Inbred C57BL , Myeloid Differentiation Factor 88 , NF-kappa B , Oils, Volatile , Plant Bark , Toll-Like Receptor 4 , Animals , Acute Lung Injury/drug therapy , Acute Lung Injury/chemically induced , Toll-Like Receptor 4/metabolism , Cinnamomum aromaticum/chemistry , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Myeloid Differentiation Factor 88/metabolism , NF-kappa B/metabolism , Plant Bark/chemistry , Mice , Anti-Inflammatory Agents/pharmacology , Macrophages/drug effects , Male , Signal Transduction/drug effects , Disease Models, Animal , Acrolein/analogs & derivatives
11.
J Toxicol Environ Health A ; 87(12): 516-531, 2024 Jun 17.
Article in English | MEDLINE | ID: mdl-38619152

ABSTRACT

The bark extract from Endopleura uchi has been widely used in traditional medicine to treat gynecological-related disorders, diabetes, and dyslipidemias albeit without scientific proof. In addition, E. uchi bark extract safety, especially regarding mutagenic activities, is not known. The aim of this study was to determine the chemical composition, antitumor, and toxicological parameters attributed to an E. uchi bark aqueous extract. The phytochemical constitution was assessed by colorimetric and chromatographic analyzes. The antiproliferative effect was determined using sulforhodamine B (SRB) assay using 4 cancer cell lines. Cytotoxic and genotoxic activities were assessed utilizing MTT and comet assays, respectively, while mutagenicity was determined through micronucleus and Salmonella/microsome assays. The chromatographic analysis detected predominantly the presence of gallic acid and isoquercitrin. The antiproliferative effect was more pronounced in human colon adenocarcinoma (HT-29) and human breast cancer (MCF-7) cell lines. In the MTT assay, the extract presented an IC50 = 39.1 µg/ml and exhibited genotoxic (comet assay) and mutagenic (micronucleus test) activities at 20 and 40 µg/ml in mouse fibroblast cell line (L929) and mutagenicity in the TA102 and TA97a strains in the absence of S9 mix. Data demonstrated that E. uchi bark possesses bioactive compounds which exert cytotoxic and genotoxic effects that might be associated with its antitumor potential. Therefore, E. uchi bark aqueous extract consumption needs to be approached with caution in therapeutic applications.


Subject(s)
Adenocarcinoma , Antineoplastic Agents , Colonic Neoplasms , Humans , Mice , Animals , Plant Extracts/chemistry , Plant Bark/chemistry , DNA Damage , Water , Mutagens , MCF-7 Cells
12.
J Nat Med ; 78(3): 558-567, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38517622

ABSTRACT

A total of five new mexicanolides (1-5), namely alliaxylines A-E, together with two known limonoids 6 and 7, were isolated and identified from Dysoxylum alliaceum (Blume) Blume ex. A.Juss. (Meliaceae). The structures of these compounds were elucidated based on extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D, and 2D NMR, as well as theoretical stimulation of NMR shifts with the DP4 + algorithm. Consequently, this study aimed to examine cytotoxic activities of these compounds against MCF-7 and A549 cell lines. The results implied that compound 2 was the most potent against the two tested cells, with IC50 values of 34.95 ± 0.21 and 44.39 ± 1.03 µM.


Subject(s)
Limonins , Meliaceae , Plant Bark , Humans , Meliaceae/chemistry , Plant Bark/chemistry , Limonins/chemistry , Limonins/pharmacology , Limonins/isolation & purification , Molecular Structure , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , MCF-7 Cells , A549 Cells , Cell Line, Tumor , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Stems/chemistry
13.
J Nat Prod ; 87(4): 1023-1035, 2024 Apr 26.
Article in English | MEDLINE | ID: mdl-38536967

ABSTRACT

The plant Goniothalamus leiocarpus of the Annonaceae family is used as an alternative medicine in tropical regions. Applying high-speed counter current chromatography (HSCCC), eight new bioactive styrylpyrone isomers, including 6R,7S,8R,2'S-goniolactone B (1), 6S,7S,8S,2'S-goniolactone B (2), 6R,7R,8R,2'S-goniolactone B (3), 6R,7S,8S,2'S-goniolactone C (4), 6R,7S,8R,2'S-goniolactone C (5), 6S,7R,8S,2'S-goniolactone C (6), and two positional isomers, 6R,7R,8R,2'S-goniolactone G (7) and 6S,7R,8R,2'S-goniolactone G (8), were isolated from a chloroform fraction (2.1 g) of G. leiocarpus, which had a prominent spot by TLC analysis. The structures of the new compounds were elucidated by MS, NMR, IR, and UV spectra, and their absolute configurations were determined by Mosher's method, ECD, and X-ray diffraction analysis. The isolates are characteristic components found in plants of the genus Goniothalamus and consist of two structural moieties: a styrylpyrone and a dihydroflavone unit. The isolation of the eight new compounds demonstrates the effectiveness of HSCCC in separating the isomers of natural styrylpyrone. In a bioactivity assessment, compounds 1 and 6 exhibited cytotoxic effects against the human colon carcinoma cell lines LS513 and SW620 with IC50 values ranging from 1.6 to 3.9 µM. Compounds 1, 2, 7, and 8 showed significant synergistic activity against antibiotic-resistant Staphylococcus aureus strains.


Subject(s)
Goniothalamus , Plant Bark , Pyrones , Goniothalamus/chemistry , Pyrones/chemistry , Pyrones/pharmacology , Pyrones/isolation & purification , Molecular Structure , Stereoisomerism , Plant Bark/chemistry , Humans , Countercurrent Distribution/methods , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification
14.
New Phytol ; 242(3): 1000-1017, 2024 May.
Article in English | MEDLINE | ID: mdl-38433329

ABSTRACT

Drought affects the complex interactions between Norway spruce, the bark beetle Ips typographus and associated microorganisms. We investigated the interplay of tree water status, defense and carbohydrate reserves with the incidence of bark beetle attack and infection of associated fungi in mature spruce trees. We installed roofs to induce a 2-yr moderate drought in a managed spruce stand to examine a maximum of 10 roof and 10 control trees for resin flow (RF), predawn twig water potentials, terpene, phenolic and carbohydrate bark concentrations, and bark beetle borings in field bioassays before and after inoculation with Endoconidiophora polonica and Grosmannia penicillata. Drought-stressed trees showed more attacks and significantly longer fungal lesions than controls, but maintained terpene resin defenses at predrought levels. Reduced RF and lower mono- and diterpene, but not phenolic concentrations were linked with increased host selection. Bark beetle attack and fungi stimulated chemical defenses, yet G. penicillata reduced phenolic and carbohydrate contents. Chemical defenses did not decrease under mild, prolonged drought in our simulated small-scale biotic infestations. However, during natural mass attacks, reductions in carbon fixation under drought, in combination with fungal consumption of carbohydrates, may deplete tree defenses and facilitate colonization by I. typographus.


Subject(s)
Coleoptera , Picea , Weevils , Animals , Droughts , Picea/microbiology , Plant Bark/chemistry , Plant Diseases/microbiology , Terpenes , Phenols , Norway , Water/analysis , Carbohydrates/analysis
15.
Sci Rep ; 14(1): 6259, 2024 03 15.
Article in English | MEDLINE | ID: mdl-38491054

ABSTRACT

Urban trees' biomonitoring of pollutants such as polycyclic aromatic hydrocarbons (PAHs) yields pertinent and useful data for air pollution management. The aim of this study was to biomonitor PAHs in pine (Pinus eldarica Medw.) trees in the city of Isfahan and identify their sources. In total, 34 samples of outer bark of the trees were collected and their contents of 16 EPA PAHs were analyzed. With a median value of 136.3 ng/g, the total PAH contents in tree barks varied from 53.4 to 705.2 ng/g. The average values of the diagnostic ratios for Ant/(Ant + Phe), Flu/(Flu + Py), BaA/(BaA + Chr) and IP/(IP + BP) were 0.19, 0.49, 0.45 and 0.49, respectively, revealing the PAHs majority source of pyrogenic. Meanwhile, principal component analysis showed two major types of PAHs sources including pyrogenic (fossil fuel combustion and industrial activities) and petrogenic (uncombusted) sources. The average ratio An/(An + Phe) and Flu/(Flu + Py) in bark samples was close to their relevant ratios in ambient air which demonstrated the potential use of this approach for biomonitoring of PAHs.


Subject(s)
Air Pollutants , Environmental Pollutants , Pinus , Polycyclic Aromatic Hydrocarbons , Polycyclic Aromatic Hydrocarbons/analysis , Biological Monitoring , Plant Bark/chemistry , Environmental Monitoring , Environmental Pollutants/analysis , China , Air Pollutants/analysis
16.
Phytochemistry ; 220: 114009, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38342289

ABSTRACT

Seven previously undescribed preurianin-type limonoids, namely paraxylines A-G, and three known analogs were isolated from stem bark of Dysoxylum parasiticum. The structures, including absolute configurations, were established through spectroscopic analyses, quantum chemical calculations using the density functional theory method, as well as the DP4+ algorithm. Paraxylines A-G were identified as the first preurianin-type with full substitution at C, D-rings, leading to the highly oxygenated seco-limonoids skeleton. The secreted alkaline phosphate assay against an engineered human and murine TLR4 of HEK-Blue cells was performed to evaluate the immune regulating effects. Among them, paraxyline B was found to be a remarkable TLR4 agonist whereas two analogs (toonapubesins A and B) were found to antagonise lipopolysaccharide stimulation of the TLR4 pathway. Paraxylines A and C-E acted either as agonists or antagonists depending on the origin of the TLR4 receptor (human or mouse). The effect of these selected compounds on the expression of pro-inflammatory cytokines TNF-α, IL-1α, IL-1ß, and IL-6 of the NF-κB signaling pathway were examined in macrophage cell lines, revealing dose-dependent effects. Additionally, paraxylines A, C, D, and G also presented modest cytotoxic activity against MCF-7 and HeLa cell lines with IC50 values ranging from 23.1 to 43.5 µM.


Subject(s)
Antineoplastic Agents, Phytogenic , Antineoplastic Agents , Limonins , Meliaceae , Humans , Animals , Mice , Limonins/pharmacology , Limonins/chemistry , Toll-Like Receptor 4 , HeLa Cells , Plant Bark/chemistry , Molecular Structure , Antineoplastic Agents, Phytogenic/chemistry , Meliaceae/chemistry
17.
J Pharm Biomed Anal ; 242: 116066, 2024 May 15.
Article in English | MEDLINE | ID: mdl-38417325

ABSTRACT

Toxicodendron vernicifluum bark has been used for many years as a component in foods and as a traditional herbal medication. Unfortunately, the presence of urushiols, which induce allergies, limits its application. This study used a vortex-blending matrix solid-phase dispersion microextraction technique to extract urushiols from Toxicodendron vernicifluum bark. HPLC was used to evaluate the amounts of the extracted urushiols (15:0, 15:1, 15:2, and 15:3). The modified magnetic adsorbent was prepared through an in situ coprecipitation method and characterized using a variety of techniques. The optimized extraction conditions are as follows: using magnetic Zeolite Socony Mobil-Five as an adsorbent, a 1:2 sample/adsorbent ratio, 2.5 min of vortex-blending time, 4 mL of 0.1% (V/V) trifluoroacetic acid-methanol as the elution solvent and 8 min of ultrasound time. There was good linearity and high repeatability in the method. Furthermore, the limits of detection for the urushiols ranged from 0.20 to 0.50 µg/mL. Under the optimized conditions, 50 compounds were identified by ultra high performance liquid chromatography and quadrupole time-of-flight mass spectrometry. These compounds included 8 phenolic acids, 9 monomeric urushiols, 11 urushiol dimers, 10 other components, and 11 flavonoids. The suggested approach, which has the advantages of few stages and high extraction efficiency over existing extraction procedures, is a potentially useful method for obtaining and evaluating urushiols in raw materials or extracts.


Subject(s)
Toxicodendron , Chromatography, High Pressure Liquid/methods , Toxicodendron/chemistry , Plant Bark/chemistry , Catechols/analysis , Solid Phase Extraction/methods
18.
Steroids ; 205: 109390, 2024 May.
Article in English | MEDLINE | ID: mdl-38367679

ABSTRACT

The Genus Dysoxylum (Meliaceae) consists of approximately 80 species that are abundant in structurally diverse triterpenoids. The present study focused on isolating new triterpenoids from the bark of Dysoxylum malabaricum, one of the predominant species of Dysoxylum present in India. The methanol-dichloromethane bark extract was subjected to LCMS profiling followed by silica gel column chromatography and HPLC analysis to target new compounds. Two new ring A-modified cycloartane-type triterpenoids (1 and 2) were isolated from the bark extract. Spectroscopic methods like NMR, HRESIMS data, and electronic circular dichroism calculations elucidated the structuresandabsolute configurations of the isolated compounds. These compounds were evaluated for their cytotoxic potential against breast cancer cells and displayed notable cytotoxicity. Compound 1 exhibited the highest cytotoxicity against the MDA-MB-231 cells and induced apoptotic cell death. Also, it was able to inhibit glucose uptake and increase nitric oxide production in breast cancer cells.


Subject(s)
Antineoplastic Agents, Phytogenic , Breast Neoplasms , Meliaceae , Triterpenes , Humans , Female , Molecular Structure , Plant Bark/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Triterpenes/pharmacology , Triterpenes/chemistry , Meliaceae/chemistry , Plant Extracts/chemistry
19.
Environ Res ; 250: 118455, 2024 Jun 01.
Article in English | MEDLINE | ID: mdl-38367838

ABSTRACT

Cork oak and pine bark, two of the most prolific byproducts of the European forestry sector, were assessed as biosorbents for eliminating potentially toxic elements (PTEs) from water-based solutions. Our research suggests that bioadsorption stands out as a viable and environmental eco-friendly technology, presenting a sustainable method for the extraction of PTEs from polluted water sources. This study aimed to evaluate and compare the efficiency of cork powder and pine bark powder as biosorbents. Specifically, the adsorption of Fe, Cu, Zn, Cd, Ni, Pb and Sn at equilibrium were studied through batch experiments by varying PTEs concentrations, pH, and ionic strength. Results from adsorption-desorption experiments demonstrate the remarkable capacity of both materials to retain the studied PTE. Cork powder and pine bark powder exhibited the maximum retention capacity for Fe and Cd, while they performed poorly for Pb and Sn, respectively. Nevertheless, pine bark showed a slightly lower retention capacity than cork. Increasing the pH resulted in cork showing the highest adsorption for Zn and the lowest for Sn, while for pine bark, Cd was the most adsorbed, and Sn was the least adsorbed, respectively. The highest adsorption of both materials occurred at pH 3.5-5, depending on the PTE tested. The ionic strength also influenced the adsorption of the various PTEs for both materials, with decreased adsorption as ionic strength increased. The findings suggest that both materials could be effective for capturing and eliminating the examined PTEs, albeit with different efficiencies. Remarkably, pine bark demonstrated superior adsorption capabilities, which were observed to vary based on the specific element and the experimental conditions. These findings contribute to elucidating the bio-adsorption potential of these natural materials, specifically their suitability in mitigating PTEs pollution, and favoring the recycling and revalorization of byproducts that might otherwise be considered residue.


Subject(s)
Pinus , Plant Bark , Quercus , Water Pollutants, Chemical , Pinus/chemistry , Quercus/chemistry , Plant Bark/chemistry , Adsorption , Water Pollutants, Chemical/analysis , Water Pollutants, Chemical/chemistry , Powders/chemistry , Hydrogen-Ion Concentration , Metals, Heavy/analysis , Metals, Heavy/chemistry
20.
J Anim Physiol Anim Nutr (Berl) ; 108(3): 816-838, 2024 May.
Article in English | MEDLINE | ID: mdl-38324000

ABSTRACT

Eucommia ulmoides has been used as a food and medicine homologue for a long time in China. We hypothesize that Eucommia ulmoides achieves its health-promoting effects via altering gut microbiota. Here, we investigated the effects of water extract of Eucommia ulmoides bark on caecal microbiota and growth performance, antioxidant activity, and immunity in white-feathered broilers treated for 42 days. A total of 108 one-day-old Cobb white-feathered broilers were randomly assigned to three treatment groups: control diet, 0.75% Eucommia ulmoides diet (EU Ⅰ) and 1.5% Eucommia ulmoides diet (EU Ⅱ). The results showed that EU Ⅱ treatment improved average body weight (ABW), thigh muscle quality and total length of intestines, and decreased the serum total triglycerides and total cholesterol (TC) (p < 0.05). Eucommia ulmoides supplementation increased serum superoxide dismutase (SOD), glutathione peroxidase (GSH-Px), total antioxidant activities and content of immunoglobulins, and reduced levels of malondialdehyde and tumour necrosis factor-α (TNF-α) (p < 0.05). Moreover, the supplementation increased the diversity of caecal microbiota and reduced the pathogenic genera Escherichia Shigella and Helicobacter. The genera Ochrobactrum, Odoribater, Klebsiella, Enterobacter, Georgenia and Bifidobacterium were positively associated with the ABW, total intestinal length, serum levels of GSH-Px, SOD and immunoglobulins (p < 0.001) and negatively associated with the TC and TNF-α (p < 0.01), suggesting an association of the changes of gut microbiota and improvement of broiler health. Meanwhile, Eucommia ulmoides supplementation enriched the Kyoto Encyclopedia of Genes and Genomes pathway of exocrine secretion from the pancreas, circadian entrainment and inhibited lipopolysaccharide biosynthesis. In conclusion, Eucommia ulmoides water extract can be used as a feed additive to improve poultry industry production.


Subject(s)
Animal Feed , Cecum , Chickens , Diet , Dietary Supplements , Eucommiaceae , Plant Bark , Plant Extracts , Animals , Eucommiaceae/chemistry , Animal Feed/analysis , Plant Extracts/pharmacology , Plant Extracts/administration & dosage , Plant Extracts/chemistry , Cecum/microbiology , Diet/veterinary , Plant Bark/chemistry , Animal Nutritional Physiological Phenomena , Gastrointestinal Microbiome/drug effects
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