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1.
J Agric Food Chem ; 72(19): 10970-10980, 2024 May 15.
Article in English | MEDLINE | ID: mdl-38708787

ABSTRACT

Eleven alkaloids (1-11) including seven new ones, 1-7, were isolated from the solid fermentation of Aspergillus fumigatus VDL36, an endophytic fungus isolated from the leaves of Vaccinium dunalianum Wight (Ericaceae), a perennial evergreen shrub distributed across the Southwest regions of China, Myanmar, and Vietnam. Their structures were elucidated on the basis of extensive spectroscopic methods. The isolates were evaluated for in vitro antifungal activities against five phytopathogenic fungi (Fusarium oxysporum, Coriolus versicolor, Fusarium solani, Botrytis cinerea, Fusarium graminearum). As a result, the new compounds fumigaclavine I (1), 13-ethoxycyclotryprostatin A (5), 13-dehydroxycyclotryprostatin A (6), and 12ß-hydroxy-13-oxofumitremorgin C (7) exhibited antifungal activities with MIC values of 7.8-62.5 µg/mL which were comparable to the two positive controls ketoconazole (MIC = 7.8-31.25 µg/mL) and carbendazim (MIC = 1.95-7.8 µg/mL). Furthermore, compounds 1 and 5 demonstrated potent protective and curative effects against the tomato gray mold in vivo. Preliminary structure-activity relationships of the tested indole diketopiperazine alkaloids indicate that the introduction of a substituent group at position C-13 enhances their biological activities.


Subject(s)
Alkaloids , Aspergillus fumigatus , Endophytes , Alkaloids/pharmacology , Alkaloids/chemistry , Aspergillus fumigatus/drug effects , Endophytes/chemistry , Molecular Structure , Fusarium/drug effects , Fungicides, Industrial/pharmacology , Fungicides, Industrial/chemistry , Plant Leaves/microbiology , Plant Leaves/chemistry , Microbial Sensitivity Tests , China , Plant Diseases/microbiology
2.
Med Sci Monit ; 30: e945188, 2024 May 22.
Article in English | MEDLINE | ID: mdl-38775003

ABSTRACT

This publication has been retracted by the Editor due to the identification of non-original figure images and manuscript content that raise concerns regarding the credibility and originality of the study and the manuscript. Reference: Ying-Jun Zhang, He Huang, Yu Liu, Bin Kong, Guangji Wang. MD-1 Deficiency Accelerates Myocardial Inflammation and Apoptosis in Doxorubicin-Induced Cardiotoxicity by Activating the TLR4/MAPKs/Nuclear Factor kappa B (NF-kappaB) Signaling Pathway. Med Sci Monit, 2019; 25: 7898-7907. DOI: 10.12659/MSM.919861.


Subject(s)
Apoptosis , Cardiotoxicity , Doxorubicin , NF-kappa B , Signal Transduction , Toll-Like Receptor 4 , Toll-Like Receptor 4/metabolism , Toll-Like Receptor 4/genetics , Toll-Like Receptor 4/deficiency , NF-kappa B/metabolism , Doxorubicin/adverse effects , Doxorubicin/pharmacology , Apoptosis/drug effects , Animals , Cardiotoxicity/metabolism , Cardiotoxicity/etiology , Signal Transduction/drug effects , Inflammation/metabolism , Inflammation/pathology , Myocardium/pathology , Myocardium/metabolism , Mice , Lymphocyte Antigen 96/metabolism , Male , Mitogen-Activated Protein Kinases/metabolism
3.
Phytochemistry ; 223: 114122, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38710376

ABSTRACT

Quantitative analysis of Rumex nepalensis var. remotiflorus revealed that its roots contain rich anthraquinones, which has emodin, chrysophanol, and physcion contents of up to 0.30, 0.67, and 0.98 mg/g, respectively. Further phytochemical study led to the isolation and purification of seven undescribed phenolic constituents, including one flavan derivative with a 13-membered ring, polygorumin A (1), two dianthrone glucosides, polygonumnolides F and G (2, 3), two diphenylmethanones, rumepalens A and B (4, 5), and a pair of epimeric oxanthrone C-glucosides, rumejaposides K and L (6a, 6b) from the roots of R. nepalensis var. remotiflorus. Furthermore, 1 undescribed natural product, 1-ß-D-glucoside-6'-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate]-3-hydroxy-5-methylphenyl (19), and 21 known phenolic compounds were obtained from the aforementioned plant for the first time. Their structures were elucidated through extensive spectroscopic data analysis. Notably, compounds 1, 4-5, and 7-9 exhibited inhibitory activity on α-glucosidase with IC50 values ranging from 1.61 ± 0.17 to 32.41 ± 0.87 µM. In addition, the isolated dianthrone, chrysophanol bianthrone (14), showed obvious cytotoxicity against four human cancer cell lines (HL-60, SMMC-7721, A-549, and MDA-MB-231) with IC50 values ranging from 3.81 ± 0.17 to 35.15 ± 2.24 µM. In silico target prediction and molecular docking studies demonstrated that the mechanism of the anticancer activity of 14 may be related to the interaction with protein kinase CK2.


Subject(s)
Antineoplastic Agents, Phytogenic , Glycoside Hydrolase Inhibitors , Phenols , Rumex , alpha-Glucosidases , Humans , Phenols/pharmacology , Phenols/chemistry , Phenols/isolation & purification , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Rumex/chemistry , alpha-Glucosidases/metabolism , alpha-Glucosidases/drug effects , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Molecular Structure , Drug Screening Assays, Antitumor , Molecular Docking Simulation , Structure-Activity Relationship , Cell Line, Tumor , Plant Roots/chemistry , Dose-Response Relationship, Drug , Cell Proliferation/drug effects
4.
Nat Prod Res ; : 1-7, 2024 Jan 08.
Article in English | MEDLINE | ID: mdl-38189345

ABSTRACT

Two new triterpenoids, namely 24-methylene-5,24-dien-19(10→9)-abeo-8α,9ß,10α-eupha-3ß-ol (1) and 24-methyl-5,23-dien-19(10→9)-abeo-8α,9ß,10α-eupha-3ß-ol (2) were isolated from the stems of Euphorbia royleana, together with three known analogs. The structures of the new compounds were elucidated by extensive 1H NMR,13C NMR, HSQC, HMBC, 1H-1H COSY, ROESY and HR-MS spectroscopic analyses.

5.
Huan Jing Ke Xue ; 45(1): 480-488, 2024 Jan 08.
Article in Chinese | MEDLINE | ID: mdl-38216497

ABSTRACT

Microplastics can become potential transport carriers of other environmental pollutants (such as heavy metals), so the combined pollution of microplastics and heavy metals has attracted increasing attention from researchers. To explore the mechanism of plant growth-promoting bacteria VY-1 alleviating the combined pollution stress of heavy metals and microplastics in sorghum, the effects of inoculation on biomass and accumulation of heavy metals in sorghum were analyzed using a hydroponics experiment, and the effects of inoculation on gene expression in sorghum were analyzed via transcriptomics. The results showed that the combined pollution of polyethylene (PE) and cadmium (Cd) decreased the dry weight of above-ground and underground parts by 17.04% and 10.36%, respectively, compared with that under the single Cd pollution, which showed that the combined toxicity effect of the combined pollution on plant growth was enhanced. The inoculation of plant growth-promoting bacteria VY-1 could alleviate the toxicity of Cd-PE combined pollution and increase the length of aboveground and underground parts by 33.83% and 73.21% and the dry weight by 56.64% and 33.44%, respectively. Transcriptome sequencing showed that 904 genes were up-regulated after inoculation with VY-1. Inoculation with growth-promoting bacteria VY-1 could up-regulate the expression of several genes in the auxin, abscisic acid, flavonoid synthesis, and lignin biosynthesis pathways, which promoted the response ability of sorghum under Cd-PE combined pollution stress and improved its resistance. The above results indicated that plant growth-promoting bacteria could alleviate the stress of heavy metal and microplastic combined pollution by regulating plant gene expression, which provided a reference for plant-microbial joint remediation of heavy metal and microplastic combined pollution.


Subject(s)
Metals, Heavy , Soil Pollutants , Sorghum , Cadmium/analysis , Microplastics , Plastics , Sorghum/genetics , Sorghum/metabolism , Metals, Heavy/toxicity , Metals, Heavy/metabolism , Bacteria/genetics , Bacteria/metabolism , Gene Expression Profiling , Soil Pollutants/analysis , Biodegradation, Environmental , Soil
6.
J Exp Bot ; 75(7): 1982-1996, 2024 Mar 27.
Article in English | MEDLINE | ID: mdl-38124377

ABSTRACT

Drought-induced leaf senescence is associated with high sugar levels, which bears some resemblance to the syndrome of diabetes in humans; however, the underlying mechanisms of such 'plant diabetes' on carbon imbalance and the corresponding detoxification strategy are not well understood. Here, we investigated the regulatory mechanism of exogenous methylglyoxal (MG) on 'plant diabetes' in maize plants under drought stress applied via foliar spraying during the grain-filling stage. Exogenous MG delayed leaf senescence and promoted photoassimilation, thereby reducing the yield loss induced by drought by 14%. Transcriptome and metabolite analyses revealed that drought increased sugar accumulation in leaves through inhibition of sugar transporters that facilitate phloem loading. This led to disequilibrium of glycolysis and overaccumulation of endogenous MG. Application of exogenous MG up-regulated glycolytic flux and the glyoxalase system that catabolyses endogenous MG and glycation end-products, ultimately alleviating 'plant diabetes'. In addition, the expression of genes facilitating anabolism and catabolism of trehalose-6-phosphate was promoted and suppressed by drought, respectively, and exogenous MG reversed this effect, implying that trehalose-6-phosphate signaling in the mediation of 'plant diabetes'. Furthermore, exogenous MG activated the phenylpropanoid biosynthetic pathway, promoting the production of lignin and phenolic compounds, which are associated with drought tolerance. Overall, our findings indicate that exogenous MG activates defense-related pathways to alleviate the toxicity derived from 'plant diabetes', thereby helping to maintain leaf function and yield production under drought.


Subject(s)
Diabetes Mellitus , Zea mays , Humans , Zea mays/genetics , Plant Senescence , Pyruvaldehyde/metabolism , Pyruvaldehyde/pharmacology , Droughts , Diabetes Mellitus/metabolism , Sugars/metabolism , Plant Leaves/metabolism , Stress, Physiological
7.
Huan Jing Ke Xue ; 44(12): 6973-6981, 2023 Dec 08.
Article in Chinese | MEDLINE | ID: mdl-38098420

ABSTRACT

The combined pollution of microplastics and heavy metals can potentially interact. This may have an important impact on the growth and development of plants and the rhizosphere microbial community and function. In this study, the effects of heavy metal cadmium combined with different types of microplastics(PE and PS), different particle sizes(13 µm and 550 µm), and different concentrations(0.1% and 1%) on Pennisetum hydridum growth were studied under pot conditions. The results showed that the effects of the combined pollution of MPs and Cd on plant dry weight and Cd accumulation varied with different types, concentrations, and particle sizes of MPs, and the combined pollution stress increased, whereas the Cd content and Cd accumulation decreased. Metagenomic analysis showed that the combined contamination of MPs and Cd could change the composition of the bacterial community and reduce bacterial diversity, among which the ACE index and Chao1 index in the 550 µm 0.1% PE+Cd treatment group were the most significant. Metagenomic analysis of microbial species function showed that the main functional groups were metabolism, amino acid transport and metabolism, energy generation and conversion, and signal transduction mechanisms. Compared with that under single Cd pollution, the addition of MPs could change the gene abundance of functional groups such as metabolism, amino acid transport and metabolism, and energy generation and conversion, and the effects of different MPs types, concentrations, and particle sizes varied. In this study, metagenomics and amplification sequencing were used to analyze the effects of the combined pollution of MPs and Cd on the bacterial community and function in P. hydridum in order to provide basic data and scientific basis for the ecotoxicological effects of the combined heavy metal pollution of MPs and its biological remediation.


Subject(s)
Metals, Heavy , Microbiota , Pennisetum , Soil Pollutants , Cadmium/analysis , Microplastics/analysis , Soil/chemistry , Pennisetum/metabolism , Plastics , Rhizosphere , Metals, Heavy/analysis , Bacteria/metabolism , Amino Acids , Soil Pollutants/analysis
8.
World J Microbiol Biotechnol ; 39(12): 352, 2023 Oct 21.
Article in English | MEDLINE | ID: mdl-37864750

ABSTRACT

Formate dehydrogenase (FDH) is a D-2-hydroxy acid dehydrogenase, which can reversibly reduce CO2 to formate and thus act as non-photosynthetic CO2 reductase. In order to increase catalytic efficiency of formate dehydrogenase for CO2 reduction, two mutants V328I/F285W and V354G/F285W were obtained of which reduction activity was about two times more than the parent CbFDHM2, and the formate production from CO2 catalyzed by mutants were 2.9 and 2.7-fold higher than that of the parent CbFDHM2. The mutants had greater potential in CO2 reduction. The optimal temperature for V328I/F285W and V354G/F285W was 55 °C, and they showed increasement of relative activity under 45 °C to 55 °C compared with parent. The optimal pH for the mutants was 9.0, and they showed excellent stability in pH 4.0-11.5. The kcat/Km values of mutants were 1.75 times higher than that of the parent. Then the molecular basis for its improvement of biochemical characteristics were preliminarily elucidated by computer-aided methods. All of these results further established a solid foundation for molecular modification of formate dehydrogenase and CO2 reduction.


Subject(s)
Carbon Dioxide , Formate Dehydrogenases , Carbon Dioxide/metabolism , Formate Dehydrogenases/genetics , Formate Dehydrogenases/chemistry , Formate Dehydrogenases/metabolism , Catalysis , Formates/metabolism
9.
Ecotoxicol Environ Saf ; 264: 115439, 2023 Oct 01.
Article in English | MEDLINE | ID: mdl-37690172

ABSTRACT

Microplastics (MPs) can act as carriers for environmental pollutants; therefore, MPs combined with heavy metal pollution are attracting increasing attention from researchers. In this study, the potential of the plant growth-promoting bacterium Bacillus sp. SL-413 to mitigate the stress caused by exposure to both MPs and cadmium (Cd) in sorghum plants was investigated. The effects of inoculation on sorghum biomass were investigated using hydroponic experiments, and evaluation of Cd accumulation and enzyme activity changes and transcriptomics approaches were used to analyze its effect on sorghum gene expression. The results showed that combined polyethylene (PE) and Cd pollution reduced the length and the fresh and dry weights of sorghum plants and thus exerted a synergistic toxic effect. However, inoculation with the strains alleviated the stress caused by the combined pollution and significantly increased the biomass. Inoculation increased the dry weights of the aboveground and belowground parts by 11.5-44.6% and 14.9-38.4%, respectively. Plant physiological measurements indicated that inoculation reduced the reactive oxygen species (ROS) content of sorghum by 10.5-27.2% and thereby alleviated oxidative stress. Transcriptome sequencing showed that exposure to combined Cd+MP contamination induced downregulation of gene expression, particularly that of genes related to amino sugar and nucleotide sugar metabolism, starch and sucrose metabolism, and plant hormone signal transduction, in sorghum. However, inoculation with Bacillus sp. SL-413 resulted in an increase in the proportion of upregulated genes involved in signal transduction, antioxidant defense, cell wall biology, and other metabolic pathways, which included the phenylpropanoid biosynthesis, photosynthesis, flavonoid biosynthesis, and MAPK signaling pathways. The upregulation of these genes promoted the tolerance of sorghum under combined Cd+MP pollution stress and alleviated the stress induced by these conditions. This study provides the first demonstration that plant growth-promoting bacteria can alleviate the stress caused by combined pollution with MPs and Cd by regulating plant gene expression. These findings provide a reference for the combined plant-microbial remediation of MPs and Cd.


Subject(s)
Bacillus , Sorghum , Cadmium/toxicity , Antioxidants , Plastics , Microplastics , Sorghum/genetics , Bacteria , Bacillus/genetics , Body Weight , Gene Expression
10.
Fitoterapia ; 170: 105657, 2023 Oct.
Article in English | MEDLINE | ID: mdl-37604244

ABSTRACT

Four new phenolic compounds, including two naphthalenes, musizin-8-O-ß-D-(6'-O-malonyl-3''-methoxy)glucopyranoside (1) and 2-acetyl-3-methyl-1,4-naphtho-quinone-8-O-ß-D-glucopyranoside (2), one chromone, (2'R)-7-hydroxy-2-(2'-hydroxypropyl)-5-methyl acetate chromone (3), and one xanthone, 2,8-dimethyl-3,6-dihydroxyxanthone (4) were isolated from the roots of Rumex dentatus L. (Polygonaceae). In addition, five known including four naphthalenes (5-8) and one chromone (9) were also obtained. Their structures were determined by means of extensive spectroscopic analysis and acidic hydrolysis. Compound 1 showed moderate antifungal activity against Epidermophyton floccosum, with inhibitory rate of 39.539 ± 0.412% at a concentration of 100 µM.


Subject(s)
Polygonaceae , Rumex , Molecular Structure , Polygonaceae/chemistry , Plant Roots/chemistry , Naphthalenes
11.
Foods ; 12(13)2023 Jun 28.
Article in English | MEDLINE | ID: mdl-37444250

ABSTRACT

Camellia taliensis (W. W. Smith) Melchior, belonging to the genus Camellia sect. Thea., is mainly distributed from northern Myanmar to western and southwestern Yunnan province of China, and its leaves have been used to make various teas by the locals of its growing regions. The chemical constituents of C. taliensis are significantly related to those of cultivated tea plants, C. sinensis and C. sinensis var. assamica. The HPLC-ESI-MS analysis of black tea prepared from the leaves of C. taliensis showed a rich existence of polyphenols. Further comprehensive chemical study led to the separation and recognition of 32 compounds (1-32), including one new hydrolyzable tannin, 1-O-galloyl-4,6-tetrahydroxydibenzofurandicarboxyl-ß-D-glucopyranose (1), and one new natural product (24). The known compounds referred to seven hydrolyzable tannins (2-8), 10 flavonols and glycosides (9-18), and 14 simple phenolics (19-32). Their structures were elucidated by comprehensive spectroscopic analyses. Among them, 20 compounds (2, 3, 6, 7, 8, 15, 17, 18, 20-22, 24-32) were isolated from black tea for the first time. Most isolates displayed obvious antioxidant activities on DPPH and ABTS+ assays, and the hydrolyzable tannins 1, 3-5, 7, and 8 exhibited stronger inhibitory activities on α-glycosidase than quercetin and acarbose (IC50 = 5.75 and 223.30 µM, respectively), with IC50 values ranging from 0.67 to 2.01 µM.

12.
RSC Adv ; 13(16): 11037-11043, 2023 Apr 03.
Article in English | MEDLINE | ID: mdl-37033442

ABSTRACT

Panax notoginseng (PN) is a well-known traditional Chinese medicine, with dammarane-type triterpenoid saponins characterized as major component and active ingredients, together with amino acids, flavonoids, polysaccharides, and polyacetylenes. The roots of PN are susceptible to root rot disease, which causes a huge loss and changes in the chemical components of this precious resource. In this study, sub-fractions of rot PN root extracts were preliminarily found to have admirable cytotoxicity on two human cancer cells. Further bioassay-guided isolation discovered nine new non-triterpenoids, including two novel N-methylacetamido-1-oxotetrahydropyrimidine alkaloids (1, 2), five 2H-furanones or 2H-pyranones (3-7), and two polyacetylenic alcohols (8, 9). Their structures were illuminated by extensive spectroscopic data, calculated ECD, and X-ray diffraction analysis. Among them, 3-7 were considered to be transformed from panaxatriol through the intermediates (8, 9). The new alkaloids (1, 2) displayed noteworthy cytotoxicity against five human cancer cells with IC50 values ranging from 14 to 24 µM. In silico target prediction and molecular docking studies showed that 1 and 2 may interact with EGFR, and were verified by the experimental inhibitory effect on EGFR tyrosine kinase.

13.
J Med Chem ; 66(1): 371-383, 2023 01 12.
Article in English | MEDLINE | ID: mdl-36598095

ABSTRACT

Inadequate bioavailability is one of the most critical reasons for the failure of oral drug development. However, the way that substructures affect bioavailability remains largely unknown. Serotonin transporter (SERT) inhibitors are first-line drugs for major depression disorder, and improving their bioavailability may be able to decrease side-effects by reducing daily dose. Thus, it is an excellent model to probe the relationship between substructures and bioavailability. Here, we proposed the concept of "nonbioavailable substructures", referring to substructures that are unfavorable to bioavailability. A machine learning model was developed to identify nonbioavailable substructures based on their molecular properties and shows the accuracy of 83.5%. A more potent SERT inhibitor DH4 was discovered with a bioavailability of 83.28% in rats by replacing the nonbioavailable substructure of approved drug vilazodone. DH4 exhibits promising anti-depression efficacy in animal experiments. The concept of nonbioavailable substructures may open up a new venue for the improvement of drug bioavailability.


Subject(s)
Depressive Disorder, Major , Serotonin Plasma Membrane Transport Proteins , Rats , Animals , Serotonin Plasma Membrane Transport Proteins/metabolism , Biological Availability , Antidepressive Agents/pharmacology , Antidepressive Agents/therapeutic use , Antidepressive Agents/chemistry , Selective Serotonin Reuptake Inhibitors/pharmacology , Depressive Disorder, Major/drug therapy
14.
Nat Prod Res ; 37(1): 63-67, 2023 Jan.
Article in English | MEDLINE | ID: mdl-34498956

ABSTRACT

A new ingol diterpenoid, namely 3-de-O-acetyleuphornan R (1), along with two known analogues, euphornans E (2) and N (3) were isolated from the seeds of Euphorbia marginata Pursh. The structure of 1 was elucidated by extensive 1H NMR, 13C NMR, HSQC, HMBC, and 1H-1H COSY, and HR-MS spectroscopic analyses.


Subject(s)
Diterpenes , Euphorbia , Molecular Structure , Euphorbia/chemistry , Magnetic Resonance Spectroscopy , Diterpenes/chemistry , Seeds/chemistry
15.
Int J Mol Med ; 51(1)2023 Jan.
Article in English | MEDLINE | ID: mdl-36416350

ABSTRACT

Following the publication of the above article, an interested reader drew to the authors' attention that Figs. 1C and 2 in the paper appeared to contain instances of duplicated data. The authors were able to consult their original data files, and realized that these figures had indeed been assembled incorrectly. Moreover, they identified further errors with a number of the other figures in their published formats (specifically, Figs. 3, 4, 6 and 7), and requested that a corrigendum be published to take account of all the errors that were made during the compilation of these figures. The Editor of International Journal of Molecular Medicine has considered the authors' request to publish a corrigendum, but has declined this request on account of the large number of errors that have been identified, and subsequently determined that this article should be retracted from the Journal on the basis of an overall lack of confidence in the presented data. Upon receiving this decision from the Editor, the authors were in agreement that the article should be retracted. The Editor apologizes to the readership of the Journal for any inconvenience caused. [International Journal of Molecular Medicine 39: 527­538, 2017; DOI: 10.3892/ijmm.2017.2880].

16.
Nat Prod Res ; 37(12): 1986-1992, 2023 Jun.
Article in English | MEDLINE | ID: mdl-36008870

ABSTRACT

Eleven flavonoids including one new flavonol glycoside, quercetin-3-O-(2-α-L-rhamnopyranosyl)-ß-D-glucuronopyranosyl methyl ester (1), were isolated for the first time from the fruits of Phyllanthus acidus (L.) Skeels (Phyllanthaceae). Their structures were determined by extensive spectroscopic data. The known flavonoids, quercetin-3-O-ß-D-glucuronide methyl ester (3), quercetin-3-O-(2''-α-L-rhamnopyranosyl-6''-O-α-L-rhamno pyranosyl)-ß-D-glucopyranoside (5), myricetin (9), and 6-methoxy-naringenin (11) were isolated for the first time from the genus Phyllanthus. Flavonoids 4, 6 and 9 (IC50 = 6.01, 6.32, and 7.84 µM, respectively) showed stronger α-glucosidase inhibitory activities than the positive control, acarbose (IC50 = 306.45 µM). The fruits of P. acidus might be further developed as an anti-diabetic food supplement.


Subject(s)
Phyllanthus , Quercetin , Quercetin/analysis , Fruit/chemistry , Phyllanthus/chemistry , Flavonoids/chemistry , Glucosidases
17.
Pharmacol Res ; 184: 106457, 2022 10.
Article in English | MEDLINE | ID: mdl-36116708

ABSTRACT

Despite significant advances in the diagnosis and treatment of colorectal cancer (CRC), metastatic colorectal cancer still poses serious threat to CRC patients. The natural gallotannin 1,2,3,4,6-penta-O-galloyl-ß-D-glucose (PGG) has been shown to possess anti-tumor effects on colon cancer cells, but its anti-metastatic effect is yet to be investigated. In this study, the effects of PGG on cell proliferation, colony formation ability, motility, migration were investigated in colon cancer cells using BrdU, colony formation, scratch, and transwell assays, respectively. Western blot assay was used for assessing protein expression. The orthotopic colon tumor-bearing mouse model and human colon cancer metastatic mouse model were employed to evaluate the anti-metastatic effects of PGG. Results showed that PGG exhibited not only anti-proliferative and colony formation inhibitory effects, but also inhibition on cell adhesion, motility, and migration in both HCT116 and colon 26-M01 cells via modulating protein expression of cathepsin B, FAK, cofilin, and epithelial-to-mesenchymal transition related proteins. In addition, PGG (10 or 15 mg/kg, i.p.) could significantly inhibit liver and lung metastasis in colon cancer metastatic mice models. Furthermore, PGG could regulate the populations of T cells, macrophages, and MDSCs, while the levels of IL-2, IL-6, IL-10, IFN-γ, and TNF-α were altered after PGG treatment in metastatic CRC mice. This is the first report of the anti-metastatic effects of PGG by regulating cathepsin B-mediated extracellular matrix dynamics and epithelial-to-mesenchymal transition process in CRC. Our findings suggested that PGG has great potential to be developed as an anti-metastatic agent for metastatic CRC.


Subject(s)
Colonic Neoplasms , Hydrolyzable Tannins , Actin Depolymerizing Factors , Animals , Bromodeoxyuridine , Cathepsin B , Cell Line, Tumor , Extracellular Matrix , Glucose , Humans , Hydrolyzable Tannins/pharmacology , Hydrolyzable Tannins/therapeutic use , Interleukin-10 , Interleukin-2 , Interleukin-6 , Mice , Tumor Necrosis Factor-alpha
18.
Nat Prod Bioprospect ; 12(1): 29, 2022 Aug 03.
Article in English | MEDLINE | ID: mdl-35918556

ABSTRACT

A new seco-anthraquinone, crispuside A (1), and three new 3,4-dihydronaphthalen-1(2H)-ones, napthalenones A-C (2-4), were isolated from the roots of Rumex crispus L., along with 10 known anthraquinones (6-14) and naphthalenone (5). Their structures were fully determined by extensive spectroscopic analyses, including ECD, and X-ray crystallography in case of compound 5, whose absolute configuration was determined for the first time. The isolates 1, 6-14 were evaluated for their anti-inflammatory and anti-fungal activity against three skin fungi, e.g., Epidermophyton floccosum, Trichophyton rubrum, and Microsporum gypseum. Most of the isolates showed weak anti-fungal and anti-inflammatory activity. Only compound 9 exhibited obvious anti-fungal activity against E. floccosum (MIC50 = 2.467 ± 0.03 µM) and M. gypseum (MIC50 = 4.673 ± 0.077 µM), while the MIC50 values of the positive control terbinafine were 1.287 ± 0.012 and 0.077 ± 0.00258 µM, respectively. The results indicated that simple emodin type anthraquinone is more potential against skin fungi than its oxyglucosyl, C-glucosyl and glycosylated seco analogues.

19.
Nat Prod Bioprospect ; 12(1): 21, 2022 Jun 16.
Article in English | MEDLINE | ID: mdl-35710954

ABSTRACT

Rumex L., a genus in Polygonaceae family with about 200 species, is growing widely around the world. Some Rumex species, called "sorrel" or "dock", have been used as food application and treatment of skin diseases and hemostasis after trauma by the local people of its growing areas for centuries. To date, 29 Rumex species have been studied to contain about 268 substances, including anthraquinones, flavonoids, naphthalenes, stilbenes, diterpene alkaloids, terpenes, lignans, and tannins. Crude extract of Rumex spp. and the pure isolates displayed various bioactivities, such as antibacterial, anti-inflammatory, antitumor, antioxidant, cardiovascular protection and antiaging activities. Rumex species have important potential to become a clinical medicinal source in future. This review covers research articles from 1900 to 2022, fetched from SciFinder, Web of Science, ResearchGate, CNKI and Google Scholar, using "Rumex" as a search term ("all fields") with no specific time frame set for the search. Thirty-five Rumex species were selected and summarized on their geographical distribution, edible parts, traditional uses, chemical research and pharmacological properties.

20.
Fitoterapia ; 157: 105133, 2022 Mar.
Article in English | MEDLINE | ID: mdl-35114336

ABSTRACT

Six diterpenoids including three ent-kauranes (1-2, 4) and three cleistanthanes (3, 5-6) were isolated from the roots and stems of Phyllanthus acidus (L.) Skeels. Of them, (16S)-ent-16,17,18-tri-hydroxy-19-nor-kaur-4-en-3-one (1), phyllanthone A (2), and 6-hydroxycleistanthol (3) are new compounds, while the ent-kaurane diterpenoids were reported from the titled plant for the first time. Their structures were elucidated on the basis of the extensive spectroscopic analyses. Compounds 2 and 4-6 displayed cytotoxic potential with IC50 values ranging from 1.96 to 29.15 µM. They also showed moderate anti-inflammatory activities (IC50 = 6.30-12.05 µM). Particularly, the new ent-kaurane 2 displayed cytotoxic potential against HL-60 (IC50 = 2.00 µM) and MCF-7 (IC50 = 3.55 µM) cells, and anti-inflammatory activity (IC50 = 6.47 µM).


Subject(s)
Diterpenes, Kaurane/toxicity , Diterpenes/toxicity , Phyllanthus/chemistry , Plant Extracts/toxicity , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/toxicity , Cell Line, Tumor , Diterpenes/chemistry , Diterpenes, Kaurane/chemistry , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Extracts/chemical synthesis , Plant Roots/chemistry , Plant Stems/chemistry
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