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1.
Genome ; 67(11): 440-444, 2024 Nov 01.
Artículo en Inglés | MEDLINE | ID: mdl-38996388

RESUMEN

ß-Caryophyllene possesses potential anticancer properties against various cancers, including breast, colon, and lung cancer. Therefore, the essential oil of Ayapana triplinervis, which is rich in ß-caryophyllene, can be a potential herbal remedy for treating cancer. However, molecular and genomic studies on A. triplinervis are still sparse. In this study, we obtained 14.7 Gb of RNA-Seq data from A. triplinervis leaf RNA and assembled 137 554 transcripts with an N50 value of 1437 bp. We annotated 72 436 (52.7%) transcripts and mapped 10 640 transcripts to 156 biochemical pathways. Among them, 218 were related to terpenoid backbone biosynthesis, while 27 were linked to sesquiterpenoid and triterpenoid pathways. Ninety-four transcripts were annotated in the ß-caryophyllene and lupeol pathways. From these transcripts, for the first time, we identified 25 full-length genes encoding all the 17 enzymes involved in ß-caryophyllene biosynthesis and an additional five genes involved in lupeol biosynthesis. These genes will be useful for the metabolic engineering of ß-caryophyllene and lupeol biosynthesis, not just in A. triplinervis but also in other species.


Asunto(s)
Antineoplásicos , Asteraceae , Vías Biosintéticas , Lupanos , Sesquiterpenos Policíclicos , Transcriptoma , Sesquiterpenos Policíclicos/metabolismo , Antineoplásicos/metabolismo , Lupanos/metabolismo , Asteraceae/química , Asteraceae/genética , Asteraceae/metabolismo , Hojas de la Planta/genética , Vías Biosintéticas/genética , Proteínas de Plantas/genética
2.
Mol Biol Rep ; 51(1): 1104, 2024 Oct 30.
Artículo en Inglés | MEDLINE | ID: mdl-39476042

RESUMEN

PURPOSE: Investigation of various plant extracts using in-vitro/in-vivo assays has emerged as a promising avenue for identifying potential pharmacophores that can be developed into therapeutic drugs. This study aims to assess the bioactive compounds and antioxidant capacity of the Bolanthus turcicus (B. turcicus) and to investigate the effects on head and neck cancer (HNC) cell lines. METHODS: Methanol (MeOH), ethyl acetate (EA) and aqueous (Aq) extracts were prepared from B. turcicus, and the amount of total phenolic content (TPC) and total flavonoid content (TFC) in the extracts were analyzed by the Folin-Ciocalteu and Aluminum chloride method, respectively. In addition, the total antioxidant capacity and iron reducing potential of B. turcicus extracts were determined by the Phosphomolybdenum and Ferric ion reducing antioxidant power (FRAP) method. The effect of B. turcicus on HEp-2, SCC-90, SCC-9, FaDu HNC cell viability, motility, and cell-nuclear morphology was evaluated by MTT, scratch-wound healing assay, and Pllalloidin-DAPI staining, respectively. The effect of B. turcicus on the expression of CASP-3, BAX, and BCL-2 genes at the mRNA, protein, and intracellular level was evaluated by quantitative PCR (qPCR), western blot, and immunofluorescence staining. Moreover, Annexin V-FITC/PI, was used in flow cytometry to investigate the effect of B. turcicus on apoptosis. RESULTS: The MeOH extract exhibited the highest phenolic content, flavonoid content and antioxidant activity (p < 0.05 for all). HNC cells treated with extracts indicated delayed wound healing and decreased motility (p < 0.05 for all). Analysis of annexin V-PI staining indicated that the B. turcicus extracts induced apoptosis but not viability and necrosis in the HNC cell (p < 0.05 for all). Moreover, qPCR data regarding the apoptotic mechanism showed that the extracts could induce apoptosis by upregulation of pro-apoptotic CASP-3 and BAX genes and downregulation of anti-apoptotic BCL-2 gene (p < 0.05 for all). The expression of protein and intracellular levels of CASP-3 and BAX were increased, while the BCL-2 was decreased in cells treated with the extracts (p < 0.05 for all). In addition, diffuse pycnosis and DNA condensation in HNC cell nuclei, confirming apoptotic cell death (p < 0.05 for all). CONCLUSION: This study data indicated that B. turcicus extracts have antioxidant, cytotoxic, anti-migratory and pro-apoptotic activity. In conclusion, it has been shown that B. turcicus can be used as a potential therapeutic agent against HNC.


Asunto(s)
Antioxidantes , Apoptosis , Movimiento Celular , Supervivencia Celular , Neoplasias de Cabeza y Cuello , Extractos Vegetales , Humanos , Extractos Vegetales/farmacología , Extractos Vegetales/química , Antioxidantes/farmacología , Apoptosis/efectos de los fármacos , Línea Celular Tumoral , Movimiento Celular/efectos de los fármacos , Neoplasias de Cabeza y Cuello/tratamiento farmacológico , Neoplasias de Cabeza y Cuello/patología , Supervivencia Celular/efectos de los fármacos , Asteraceae/química , Flavonoides/farmacología , Fenoles/farmacología , Antineoplásicos Fitogénicos/farmacología
3.
J Nat Prod ; 87(3): 501-513, 2024 Mar 22.
Artículo en Inglés | MEDLINE | ID: mdl-37738100

RESUMEN

A decoction of the roots (31.6-316 mg/kg) from Stevia serrata Cav. (Asteraceae) as well as the main component (5-150 mg/kg) showed hypoglycemic and antihyperglycemic effects in mice. The fractionation of the active extract led to the isolation of dammaradiene acetate (1), stevisalioside A (2), and three new chemical entities characterized by spectroscopic methods and named stevisaliosides B-D (3-5). Glycoside 2 (5 and 50 mg/kg) decreased blood glucose levels and the postprandial peak during oral glucose and insulin tolerance tests in STZ-hyperglycemic mice. Compounds 1-5 were tested also against PTP1B1-400 and showed IC50 values of 1180.9 ± 0.33, 526.8 ± 0.02, 532.1 ± 0.03, 928.2 ± 0.39, and 31.8 ± 1.09 µM, respectively. Compound 5 showed an IC50 value comparable to that of ursolic acid (IC50 = 30.7 ± 0.00 µM). Docking studies revealed that 2-5 and their aglycones bind to PTP1B1-400 in a pocket formed by the C-terminal region. The volatilome of S. serrata was characterized by a high content of (E)-longipinene, spathulenol, guaiadiene, seychellene, and aromandendrene. Finally, a UHPLC-UV method was developed and validated to quantify the content of 2 in the decoction of the plant.


Asunto(s)
Asteraceae , Stevia , Ratones , Animales , Hipoglucemiantes/farmacología , Hipoglucemiantes/química , Stevia/química , Extractos Vegetales/química , Glucosa , Asteraceae/química , Glucemia/análisis
4.
J Nat Prod ; 87(7): 1786-1797, 2024 Jul 26.
Artículo en Inglés | MEDLINE | ID: mdl-38986603

RESUMEN

Carabranolides present characteristic NMR resonances for the cyclopropane moiety, which distinctly differ from those of other compounds and were used for an NMR-guided isolation in this study. As a result, 11 undescribed carabranolides (1-11), along with five known ones (12-16), were isolated from the fruits of Carpesium abrotanoides L. Compounds 1-11 are new esters of carabrol at C-4 with different carboxylic acids. Their structures were elucidated by HRESIMS and NMR spectroscopic data analysis. The biological evaluation showed that compounds 2-4, 15, and 16 exhibited significant inhibitory activity against LPS-induced NO release with an IC50 value of 5.6-9.1 µM and dose-dependently decreased iNOS protein expression in RAW264.7 cells.


Asunto(s)
Antiinflamatorios , Asteraceae , Frutas , Óxido Nítrico , Animales , Ratones , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Asteraceae/química , Frutas/química , Lipopolisacáridos/farmacología , Espectroscopía de Resonancia Magnética , Estructura Molecular , Óxido Nítrico/biosíntesis , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Células RAW 264.7 , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología
5.
Bioorg Chem ; 151: 107684, 2024 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-39094507

RESUMEN

Twenty-nine sesquiterpenoids, including pseudoguaiane-type (1-11), eudesmane-type (12-23), and carabrane-type (24-29), have been identified from the plant Carpesium abrotanoides. Of them, compounds 1-4, 12-15, and 24-27, namely carpabrotins A-L, are twelve previously undescribed ones. Compound 3 possessed a pseudoguaiane backbone with a rearrangement modification at C-11, C-12 and C-13, while compound 4 suffered a carbon bond break between the C-4 and C-5 to form a rare 4,5-seco-pseudoguaiane lactone. Compounds 1-3, 5, 13-16 and 25-27 exhibited anti-inflammatory activity by inhibiting NO production in LPS-induced RAW264.7 macrophages with IC50 values less than 40 µM, while compounds 1, 2, 5, 13, 14, 16, and 25-27 showed significant inhibitory activity comparable to that of dexamethasone. The anti-atopic dermatitis (AD) effects of compounds 5 and 16 were tested according to 2,4-dinitrochlorobenzene (DNCB)-induced AD-like skin lesions in KM mice, and the results revealed that the major products 5 and 16 improved the histological features of AD-like skin lesions and mast cell infiltration in mice. This study suggested that sesquiterpenoids in C. abrotanoides should play a key role in its anti-inflammatory use.


Asunto(s)
Asteraceae , Óxido Nítrico , Sesquiterpenos , Animales , Ratones , Sesquiterpenos/farmacología , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Asteraceae/química , Células RAW 264.7 , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Óxido Nítrico/metabolismo , Estructura Molecular , Relación Estructura-Actividad , Relación Dosis-Respuesta a Droga , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Macrófagos/efectos de los fármacos , Masculino
6.
Ecotoxicol Environ Saf ; 285: 117092, 2024 Oct 15.
Artículo en Inglés | MEDLINE | ID: mdl-39332200

RESUMEN

Environmental contamination by cadmium (Cd), a highly toxic heavy metal, poses significant health risks to plants and humans. Biochar has been effectively used to promote plant growth and productivity under Cd stress. This study presents an innovative application of biochar derived from the invasive weed Parthenium hysterophorus to promote plant growth and productivity under Cd stress. Our study includes detailed soil and plant analyses, providing a holistic perspective on how biochar and urea amendments influence soil properties, nutrient availability, and plant physiological responses. To address these, we established seven treatments: the control, Cd alone (5 mg kg-1), biochar alone (5 %), urea alone (3 g kg-1), biochar with Cd, urea with Cd, and a combination of biochar and urea with Cd. Cd stress alone significantly reduced plant growth indicators such as shoot and root length, fresh and dry biomass, chlorophyll content, and grain yield. However, the supplementation of biochar, urea, or their combination significantly increased shoot length (by 48%, 34%, and 65%), root length (by 73%, 46%, and 70%), and fresh shoot biomass (by 4%, 31%, and 4%), respectively. This improvement is attributed to enhanced soil properties and improved nutrient absorption. The biochar-urea combination also enhanced Cd tolerance by improving total chlorophyll content by 14 %, 13 %, and 16 % compared to the control, respectively. Similaly, these treatments significantly (p < 0.05) boosted the activity of antioxidant enzymes such as catalase, peroxidase, and superoxide dismutase by 51 %, 30 %, and 51 %, respectively, thereby mitigating oxidative stress as a defensive mechanism. The Cd tolerance was improved by biochar, urea, and their combinations, which reduced Cd content in the shoots (by 60.5 %, 38.9 %, and 51.3 %), roots (by 47.5 %, 23.9 %, and 57.6 %), and grains (by 58.1 %, 30.2 %, and 38.3 %) relative to Cd stress alone, respectively. The synergistic effects of biochar and urea are achieved through improved soil properties, nutrient availability, activating antioxidant defense mechanisms, and minimizing the accumulation of metal ions in plant tissues, thereby enhancing plant defenses against Cd stress. Conclusively, converting invasive Parthenium weed into biochar and combining it with urea offers an environmentally friendly solution to manage its spreading while effectively mitigating Cd stress in crops.


Asunto(s)
Cadmio , Carbón Orgánico , Contaminantes del Suelo , Suelo , Triticum , Urea , Cadmio/toxicidad , Carbón Orgánico/química , Carbón Orgánico/farmacología , Contaminantes del Suelo/toxicidad , Triticum/crecimiento & desarrollo , Triticum/efectos de los fármacos , Suelo/química , Asteraceae/efectos de los fármacos , Asteraceae/crecimiento & desarrollo , Asteraceae/química , Clorofila , Antioxidantes , Biomasa , Brotes de la Planta/efectos de los fármacos , Brotes de la Planta/crecimiento & desarrollo
7.
Chem Biodivers ; 21(3): e202302023, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38314937

RESUMEN

Sesquiterpene lactones are an important class of secondary metabolites frequently isolated from Lessingianthus genus that present a variety of biological properties, such as antimalarial, anti-inflammatory, antileishmanial, antitrypanosomal and anticancer. The limited phytochemical studies and the importance of this class of compounds isolated from Lessingianthus led us to study this genus. In this work, we focused on the phytochemical investigation and dereplication based on UHPLC-HRMS/MS and molecular networking of L. rubricaulis. Chemical investigation resulted in the isolation of several hirsutinolide-type sesquiterpene lactones including a new hirsutinolide derivative, 8,10α-hydroxy-1,13-bis-O-methylhirsutinolide, besides a cadinanolide and flavonoids. The dereplication study resulted in the identification of three known flavonoids, six known hirsutinolides and two known cadinanolides. Moreover, a fragmentation pathway for cadinanolide-type sesquiterpene lactones was proposed. These results contribute to chemotaxonomic studies and demonstrates the potential of Lessingianthus genus.


Asunto(s)
Asteraceae , Sesquiterpenos , Asteraceae/química , Flavonoides/farmacología , Fitoquímicos , Sesquiterpenos/química , Lactonas/química
8.
Chem Biodivers ; 21(9): e202401063, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38924351

RESUMEN

In the process of searching for anti-breast cancer agents, five sesquiterpene lactones (1-5), including two previously undescribed ones, yjaponica B-C (1-2), were isolated from the herb of Youngia japonica. Their structures were elucidated by spectroscopic data analyses and Marfey's method. Cytotoxic activities of all compounds against A549, U87, and 4T1 cell lines were tested using the CCK8 assay. The result showed that compound 3 possessed the highest cytotoxic activity against 4T1 cells with an IC50 value of 10.60 µM. Furthermore, compound 3 distinctly induced apoptosis, inhibited immigration, and blocked the cell cycle of 4T1 cells. In addition, compound 3 induced the production of reactive oxygen species. Further anticancer mechanism studies showed that compound 3 significantly upregulated expression of the cleaved caspase 3 and PARP, whereas it downregulated the expression of Bcl-2, cyclin D1, cyclin A2, CDK4, and CDK2. Taken together, our results demonstrate that compound 3 has a high potential of being used as a leading compound for the discovery of new anti-breast cancer agent.


Asunto(s)
Antineoplásicos Fitogénicos , Apoptosis , Proliferación Celular , Ensayos de Selección de Medicamentos Antitumorales , Lactonas , Sesquiterpenos , Sesquiterpenos/farmacología , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Humanos , Lactonas/farmacología , Lactonas/química , Lactonas/aislamiento & purificación , Apoptosis/efectos de los fármacos , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Estructura-Actividad , Asteraceae/química , Relación Dosis-Respuesta a Droga , Especies Reactivas de Oxígeno/metabolismo , Estructura Molecular , Descubrimiento de Drogas , Ciclo Celular/efectos de los fármacos
9.
Chem Biodivers ; 21(5): e202301719, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38361048

RESUMEN

This study focused to assess the efficacy of Gynura procumbens (GP) leaf extract against cisplatin (CP)-induced hepatorenal complications in Wister albino rats. Additionally, it aims to detect polyphenolic compounds using high-performance liquid chromatography with diode-array detection (HPLC-DAD). The rats were treated intraperitoneally with CP (7.5 mg/kg) to mediate hepatorenal damage. They were then treated with GP extract (75 and 150 mg/kg, P.O.) for 7 consecutive days. Although GP extract significantly ameliorated CP-mediated hepatorenal biomarkers like alkaline phosphatase (ALP), alanine aminotransferase (ALT), aspartate aminotransferase (AST), creatinine, and blood urea nitrogen (BUN) levels in a dose-dependent manner, GP extract at 150 mg/kg dose normalized hepatorenal biomarkers ALP (45.11 U/L), ALT (34 U/L), AST (29 U/L), creatinine (10.3 mg/dl) and BUN (11.19 mg/dl) while comparing to control and disease group. Similarly, though it significantly reduced CP-induced oxidative stress inducers, including nitric oxide (NO) and advanced oxidative protein products (AOPP), higher dose (150 mg/kg) exhibited better activity in reducing NO (281.54 mmol/gm tissue in liver and 52.73 mmol/gm tissue in the kidney) and AOPP (770.95 mmol/mg protein in liver and 651.90 mmol/mg protein in the kidney). Besides, it showed better enhancement in the antioxidant enzymes superoxide dismutase, and glutathione levels at a higher dose (150 mg/kg). Histopathological studies showed that CP caused collagen accumulation in the liver and kidney tissues. GP extract drained the collagen mass and acted against hepatorenal damage. Ellagic acid, gallic acid, quercetin hydrate, kaempferol, and rutin hydrate were revealed in GP extract. In-silico modelling showed good docking scores of the polyphenolic compounds with molecular targets including CYP4502E1, NF-κB, caspase-3, and TNF-α. GP could be an effective therapeutic option for management of anticancer drugs' complications like CP-induced organ damage, although clinical studies are required to establish herbal formulation.


Asunto(s)
Cisplatino , Estrés Oxidativo , Extractos Vegetales , Ratas Wistar , Animales , Estrés Oxidativo/efectos de los fármacos , Ratas , Extractos Vegetales/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Masculino , Hojas de la Planta/química , Mediadores de Inflamación/metabolismo , Mediadores de Inflamación/antagonistas & inhibidores , Asteraceae/química , Antioxidantes/farmacología , Antioxidantes/química , Relación Dosis-Respuesta a Droga , Hígado/efectos de los fármacos , Hígado/metabolismo , Hígado/patología , Simulación del Acoplamiento Molecular , Riñón/efectos de los fármacos , Riñón/metabolismo , Riñón/patología , Antineoplásicos/farmacología , Antineoplásicos/química
10.
J Asian Nat Prod Res ; 26(1): 26-37, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-38196236

RESUMEN

Eight new caffeoyl derivatives, elephantomentosides A-H (1 - 8), together with ten known ones (9 - 18), were isolated from the whole plant of Elephantopos tomentosus L. Their structures were elucidated using detailed spectroscopic analysis. Structurally, compounds 1 - 8 are composed of ß-D-glucopyranose, and almost all of the substituent positions are at the C-1' and C-4' of glucopyranose. The anti-inflammatory and antioxidant activities of all isolated compounds were evaluated in vitro. Compounds 9-10, 13-15, and 17-18 exhibited significant DPPH scavenging capacity with IC50 values in the range of 10.01-25.07 µM, in comparison with Vc (IC50, 17.98 µM).


Asunto(s)
Antioxidantes , Asteraceae , Estructura Molecular , Antioxidantes/farmacología , Antioxidantes/química , Asteraceae/química , Antiinflamatorios/farmacología , Antiinflamatorios/química
11.
Int J Mol Sci ; 25(19)2024 Oct 01.
Artículo en Inglés | MEDLINE | ID: mdl-39408914

RESUMEN

Phytochemical investigation of Staehelina uniflosculosa Sibth. & Sm. resulted in the isolation of twenty-two natural products: eleven sesquiterpene lactones, artemorin (1), tamirin (2), tanachin (3), reynosin (4), baynol C (5), desacetyl-ß-cyclopyrethrosin (6), 1ß-hydroxy-4α-methoxy-5α,7α,6ß-eudesm-11(13)-en-6,12-olide (7), 1ß,4α,6α-trihydroxyeudesm-11-en-8α,12-olide (8), 1ß-hydroxy-arbusculin A (9), methyl-1ß,4α,6α-trihydroxy-5α,7αH-eudesm-11(13)-en-12-oate (10) and methyl-1ß,6α,8α-trihydroxy-5α,7αH-eudesma-4(15),11(13)-dien-12-oate (11); one lignan, pinoresinol (12); one norisoprenoid, loliolide (13); six flavonoids (four genins and two glycosides), hispidulin (14), nepetin (15), jaceosidin (16), eriodictyol (17), eriodictyol-3'-O-ß-D-glucoside (18) and eriodictyol-7-O-ß-D-glucuronide (19); and three phenolic derivatives (one phenolic acid and two phenolic glucosides), protocatechuic acid (20), arbutin (21) and nebrodenside A (22). From the isolated compounds, only nepetin (15) has been reported previously from the Staehelina genus and, to the best of our knowledge, it is the first time that compound (18) has been identified in Asteraceae. A number of these substances were tested for (a) inhibition of lipoxygenase and acetylocholinesterase, (b) their antioxidant activity using the DPPH (1,1-Diphenyl-2-picrylhydrazyl) method or/and (c) inhibition of lipid peroxidation. The tested components exhibited low antioxidant activity with the exception of 5 and 22, while the effectiveness of these compounds in the inhibition of acetylocholinesterase is limited. Furthermore, Molinspiration, an online computer tool, was used to determine the bioactivity ratings of the isolated secondary metabolites. The compounds' bioactivity ratings for potential therapeutic targets were very promising.


Asunto(s)
Asteraceae , Componentes Aéreos de las Plantas , Componentes Aéreos de las Plantas/química , Componentes Aéreos de las Plantas/metabolismo , Asteraceae/química , Asteraceae/metabolismo , Metabolismo Secundario , Extractos Vegetales/química , Extractos Vegetales/farmacología , Fitoquímicos/química , Fitoquímicos/metabolismo , Estructura Molecular
12.
Int J Mol Sci ; 25(16)2024 Aug 15.
Artículo en Inglés | MEDLINE | ID: mdl-39201572

RESUMEN

The development of products with skin-protective effects has been driven by the increasing incidence of skin diseases that are exacerbated by increasing pollution, urbanization, poor living, working, fatigue, dietary habits, and general treatment. The ability of antioxidants to protect the skin from oxidative stress and its effects makes them one of the most important ingredients in today's cosmetics. This article aims first to characterize the plant extracts obtained from Acmella oleracea (A. oleracea) and then to evaluate the preliminary criteria for a new marketed product: the stability, antioxidant activity, and in vitro behavior of certain serums based on A. oleracea plant extract and hyaluronic acid. The extracts were obtained by liquid-solid extraction methods (maceration (M), ultrasound-assisted extraction (UEA), and a combined method between these two (UEA + M) using an aqueous solution of ethyl alcohol as the extraction solvent. The determination of the amounts of compounds with antioxidant activity highlighted the fact that the extract obtained from the whole plant of A. oleracea using maceration in conditions of S/L = 1:30, 20 days, and an extraction solvent percentage of 50% led to obtaining the highest amount of polyphenols (30.42 µg GAE/g), while using the combined UAE + M method under conditions of S/L = 1:30, 6 min + 20 days, and 50% extraction solvent led to obtaining the highest amount of flavonoids (32.88 mg QE/g). The tests performed on dermato-cosmetic serums based on the plant extract and multimolecular hyaluronic acid (HA) (1 HA with HMW-1.0 mDa-1.6 mDa; HA with LMW-10 kDa-200 kDa; and HA OLIGO, MW < 10 kDa) led to the conclusion that they exhibit structural stability, good shear behavior revealing a satisfactory texture, and high physical stability during storage. These results encourage the transition to in-depth testing, both microbiological and dermatological, as a final step in the consideration of a new commercial product.


Asunto(s)
Antioxidantes , Estrés Oxidativo , Extractos Vegetales , Extractos Vegetales/química , Extractos Vegetales/farmacología , Estrés Oxidativo/efectos de los fármacos , Antioxidantes/farmacología , Antioxidantes/química , Humanos , Cosméticos/química , Piel/metabolismo , Piel/efectos de los fármacos , Piel/química , Ácido Hialurónico/química , Asteraceae/química
13.
Molecules ; 29(9)2024 Apr 27.
Artículo en Inglés | MEDLINE | ID: mdl-38731504

RESUMEN

Polyphenols are ubiquitous plant metabolites that demonstrate biological activities essential to plant-environment interactions. They are of interest to plant food consumers, as well as to the food, pharmaceutical and cosmetic industry. The class of the plant metabolites comprises both widespread (chlorogenic acids, luteolin, quercetin) and unique compounds of diverse chemical structures but of the common biosynthetic origin. Polyphenols next to sesquiterpenoids are regarded as the major class of the Inuleae-Inulinae metabolites responsible for the pharmacological activity of medicinal plants from the subtribe (Blumea spp., Dittrichia spp., Inula spp., Pulicaria spp. and others). Recent decades have brought a rapid development of molecular and analytical techniques which resulted in better understanding of the taxonomic relationships within the Inuleae tribe and in a plethora of data concerning the chemical constituents of the Inuleae-Inulinae. The current taxonomical classification has introduced changes in the well-established botanical names and rearranged the genera based on molecular plant genetic studies. The newly created chemical data together with the earlier phytochemical studies may provide some complementary information on biochemical relationships within the subtribe. Moreover, they may at least partly explain pharmacological activities of the plant preparations traditionally used in therapy. The current review aimed to systematize the knowledge on the polyphenols of the Inulae-Inulinae.


Asunto(s)
Polifenoles , Polifenoles/química , Polifenoles/farmacología , Humanos , Plantas Medicinales/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Fitoquímicos/química , Fitoquímicos/farmacología , Asteraceae/química
14.
Molecules ; 29(4)2024 Feb 09.
Artículo en Inglés | MEDLINE | ID: mdl-38398567

RESUMEN

Asteraceae (Compositae), commonly known as the sunflower family, is one of the largest plant families in the world and includes several species with pharmacological properties. In the search for new antiviral candidates, an in vitro screening against dengue virus (DENV) was performed on a series of dichloromethane and methanolic extracts prepared from six Asteraceae species, including Acmella bellidioides, Campuloclinium macrocephalum, Grindelia pulchella, Grindelia chiloensis, Helenium radiatum, and Viguiera tuberosa, along with pure phytochemicals isolated from Asteraceae: mikanolide (1), eupatoriopicrin (2), eupahakonenin B (3), minimolide (4), estafietin (5), 2-oxo-8-deoxyligustrin (6), santhemoidin C (7), euparin (8), jaceidin (9), nepetin (10), jaceosidin (11), eryodictiol (12), eupatorin (13), and 5-demethylsinensetin (14). Results showed that the dichloromethane extracts of C. macrocephalum and H. radiatum and the methanolic extracts prepared from C. macrocephalum and G. pulchella were highly active and selective against DENV-2, affording EC50 values of 0.11, 0.15, 1.80, and 3.85 µg/mL, respectively, and SIs of 171.0, 18.8, >17.36, and 64.9, respectively. From the pool of phytochemicals tested, compounds 6, 7, and 8 stand out as the most active (EC50 = 3.7, 3.1, and 6.8 µM, respectively; SI = 5.9, 6.7, and >73.4, respectively). These results demonstrate that Asteraceae species and their chemical constituents represent valuable sources of new antiviral molecules.


Asunto(s)
Asteraceae , Sesquiterpenos , Extractos Vegetales/farmacología , Extractos Vegetales/química , Asteraceae/química , Cloruro de Metileno , Fitoquímicos/farmacología , Antivirales/farmacología , Sesquiterpenos/química
15.
Inflammopharmacology ; 32(5): 3375-3388, 2024 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-39039347

RESUMEN

Ayapana triplinervis (M.Vahl) R.M.King & H.Rob. (Asteraceae), popularly known as japana, is a tropical, aromatic subshrub widely used as tea to combat some diseases. The essential oil was obtained from the leaves by hydrodistillation (3 h), and the chemical composition was analyzed by gas chromatography coupled to mass spectrometry. For in vivo assays, Mus musculus/Swiss mice were used to evaluate oral acute toxicological (at dose of 2000 mg/kg); peripheral and central analgesic for abdominal contortion (doses of 6.25, 12.5, 25, 50 and 100 mg/kg), hot plate test (12.5, 25, 50, and 100 mg/kg) and formalin (25, 50 and 100 mg/kg); open field test (100 mg/kg); and anti-inflammatory by ear swelling induced by xylene (6.25,12.5, 25, 50, and 100 mg/kg). The yield of A. triplinervis essential oil (AtEO) was 4.6%, and the oxygenated monoterpene 2,5-dimethoxy-p-cymene was the major compound in this study (63.6%). AtEO at a dose of 2,000 mg/kg orally did not change the behavior patterns or mortality of the animals; liver and kidney biochemical levels were similar to the control group, indicating no liver and kidney toxicity. Moreover, AtEO, at doses of 6.25, 12.5, 25, 50, and 100 mg/kg, reduced abdominal contortions by 21%, 54%, 91%, 58%, and 55%, respectively. In the hot plate test, AtEO showed a significant increase in latency time in the 60-min interval at doses of 25 mg/kg (11.3 ± 3.3 s) and 100 mg/kg (11.9 ± 0.9 s). In the first phase of the formalin test, AtEO decreased paw licking time at doses of 25, 50, and 100 mg/kg, with inhibition of 22%, 38%, and 83%; in the second phase, the same doses, decreased licking time with inhibition of 24%, 34%, and 76%. AtEO did not present a significant change in the spontaneous locomotor activity of the animals. Doses of 6.25, 12.5, 25, 50, and 100 mg/kg significantly reduced ear edema induced by topical application of xylene with percentages of 40%, 39%, 54%, 45%, and 45%, respectively. So, AtEO demonstrated low acute oral toxicity and exhibited significant antinociceptive and anti-inflammatory actions, consistent with the use of A. triplinervis in traditional medicine.


Asunto(s)
Analgésicos , Antiinflamatorios , Aceites Volátiles , Animales , Aceites Volátiles/farmacología , Aceites Volátiles/aislamiento & purificación , Ratones , Analgésicos/farmacología , Analgésicos/aislamiento & purificación , Antiinflamatorios/farmacología , Antiinflamatorios/aislamiento & purificación , Brasil , Masculino , Relación Dosis-Respuesta a Droga , Asteraceae/química , Dolor/tratamiento farmacológico , Dolor/inducido químicamente , Edema/tratamiento farmacológico , Edema/inducido químicamente , Hojas de la Planta/química , Benzoquinonas/farmacología , Femenino
16.
Molecules ; 29(20)2024 Oct 11.
Artículo en Inglés | MEDLINE | ID: mdl-39459169

RESUMEN

Inflammation is a physiological condition that when unattended causes serious health concerns over the long term. Several phytocompounds have emerged as promising sources of anti-inflammatory agents. Thottea siliquosa is a traditional medicine for inflammatory and toxicity insults; however, this has not been scientifically confirmed. The purpose of this study is to evaluate the anti-inflammatory properties of T. siliquosa methanol leaf extract in a mouse model. This study investigates the anti-inflammatory activities of a plant extract obtained from leaves of T. siliquosa (TSE) with a focus on carrageenan- and formalin-induced paw oedema in mice. The extract's efficacy was assessed using well-established inflammation models, and the results showed a considerable reduction in paw edema in both cases. In the case of carrageenan model TSE at 50 mg/kg showed a 53.0 ± 2.5% reduction in edema, while those treated with TSM at 100 mg/kg exhibited a 60.0 ± 1.8% reduction (p < 0.01). In the case of a formalin model when a higher dose of TSE (100 mg/kg) was given, paw thickness decreased by 47.04 ± 1.9% on the fifth day and by 64.72 ± 2.2% on the tenth day. LC-MS analysis reported the presence of gallic acid, quinic acid, quercetin, clitorin, myricitrin, retronecine, batatasin II, gingerol, and coumaric acid in the extract. Overall, this study confirms that T. siliquosa extract exerts anti-inflammatory effects in animals and is possibly mediated through the combined effects of these phytochemicals.


Asunto(s)
Antiinflamatorios , Carragenina , Edema , Formaldehído , Metanol , Extractos Vegetales , Hojas de la Planta , Animales , Extractos Vegetales/farmacología , Extractos Vegetales/química , Edema/tratamiento farmacológico , Edema/inducido químicamente , Ratones , Hojas de la Planta/química , Antiinflamatorios/farmacología , Antiinflamatorios/química , Metanol/química , Masculino , Modelos Animales de Enfermedad , Asteraceae/química , Inflamación/tratamiento farmacológico , Inflamación/inducido químicamente
17.
Molecules ; 29(19)2024 Sep 30.
Artículo en Inglés | MEDLINE | ID: mdl-39407585

RESUMEN

Carpesium macrocephalum, a species native to China, Korea, Japan, and Russia, has been used medicinally in the countries of its origin. Though mono- and sesquiterpenoids are known constituents of C. macrocephalum, the complete analysis of essential oils produced by the roots and aerial parts of the plant has not been published until now. The present study discloses considerable differences in the composition and cytotoxic activity of essential oils distilled from roots and shoots of C. macrocephalum. The GC-MS-FID analyses have led to the identification of 131 compounds in all, of which 114 were found in aerial parts and 110 in the roots of the plants. The essential oil distilled from shoots contained a mixture of nerol and thymol methyl ether (c. 26%), neryl isobutyrate (c. 12%) and linalool (c. 9%) as major constituents, whereas alantolactone (c. 29%), thymol methyl ether (c. 7%) and 2,5-dimethoxy-p-cymene (thymohydroquinone dimethyl ether, c. 7%) predominated in the essential oil obtained from the roots. The oils demonstrated weak antibacterial activity against Staphylococcus aureus and, at concentrations up to 2.08 mg/mL (oil from the aerial parts) and up to 3.38 mg/mL (oil from roots), were inactive against Gram-negative bacteria. The essential oil from the roots of the plant demonstrated strong but not selective cytotoxic activity.


Asunto(s)
Asteraceae , Aceites Volátiles , Raíces de Plantas , Aceites Volátiles/farmacología , Aceites Volátiles/química , Asteraceae/química , Raíces de Plantas/química , Pruebas de Sensibilidad Microbiana , Humanos , Antibacterianos/farmacología , Antibacterianos/química , Cromatografía de Gases y Espectrometría de Masas , Componentes Aéreos de las Plantas/química , Línea Celular Tumoral
18.
Molecules ; 29(19)2024 Sep 29.
Artículo en Inglés | MEDLINE | ID: mdl-39407562

RESUMEN

Three novel ent-kaurane diterpenes, namely sigesbeckin A-C (1-3), in conjunction with eight previously identified analogues (4-11), were isolated from Sigesbeckia orientalis. Their chemical structures were resolved through multiple spectroscopic analyses. All compounds were assessed for antimicrobial bioactivity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. In particular, compounds 1 and 5 demonstrated moderate efficacy, with MIC values of 64 µg/mL. Moreover, compounds 3, 5, and 11 were found to synergize with doxorubicin hydrochloride (DOX) and vancomycin (VAN) against MRSA and VRE. The aforementioned findings offer valuable insights for the development of novel alternatives to antibiotics, which can effectively tackle the escalating issue of antibiotic resistance.


Asunto(s)
Antibacterianos , Diterpenos de Tipo Kaurano , Staphylococcus aureus Resistente a Meticilina , Pruebas de Sensibilidad Microbiana , Diterpenos de Tipo Kaurano/farmacología , Diterpenos de Tipo Kaurano/química , Diterpenos de Tipo Kaurano/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Asteraceae/química , Enterococos Resistentes a la Vancomicina/efectos de los fármacos , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Vancomicina/farmacología , Vancomicina/química , Doxorrubicina/farmacología , Sinergismo Farmacológico , Sigesbeckia
19.
Environ Monit Assess ; 196(5): 478, 2024 Apr 25.
Artículo en Inglés | MEDLINE | ID: mdl-38664274

RESUMEN

The management of invasive weeds on both arable and non-arable land is a vast challenge. Converting these invasive weeds into biochar and using them to control the fate of herbicides in soil could be an effective strategy within the concept of turning waste into a wealth product. In this study, the fate of imazethapyr (IMZ), a commonly used herbicide in various crops, was investigated by introducing such weeds as biochar, i.e., Parthenium hysterophorus (PB) and Lantana camara (LB) in sandy loam soil. In terms of kinetics, the pseudo-second order (PSO) model provided the best fit for both biochar-mixed soils. More IMZ was sorbed onto LB-mixed soil compared to PB-mixed soil. When compared to the control (no biochar), both PB and LB biochars (at concentrations of 0.2% and 0.5%) increased IMZ adsorption, although the extent of this effect varied depending on the dosage and type of biochar. The Freundlich adsorption isotherm provided a satisfactory explanation for IMZ adsorption in soil/soil mixed with biochar, with the adsorption process exhibiting high nonlinearity. The values of Gibb's free energy change (ΔG) were negative for both adsorption and desorption in soil/soil mixed with biochar, indicating that sorption was exothermic and spontaneous. Both types of biochar significantly affect IMZ dissipation, with higher degradation observed in LB-amended soil compared to PB-amended soil. Hence, the findings suggest that the preparation of biochar from invasive weeds and its utilization for managing the fate of herbicides can effectively reduce the residual toxicity of IMZ in treated agroecosystems in tropical and subtropical regions.


Asunto(s)
Carbón Orgánico , Herbicidas , Ácidos Nicotínicos , Malezas , Contaminantes del Suelo , Suelo , Carbón Orgánico/química , Contaminantes del Suelo/análisis , Herbicidas/análisis , Herbicidas/química , Suelo/química , Adsorción , Ácidos Nicotínicos/química , Lantana/química , Especies Introducidas , Cinética , Asteraceae/química
20.
Ann Pharm Fr ; 82(6): 980-993, 2024 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-38821482

RESUMEN

Spilanthes filicaulis (Schumach. & Thonn.) C. D. Adams is synonymous to Acmella caulirhiza Delile. The plant, also known as cock's eye or African cress, is a medicinal herb that belongs to the Asteraceae family. In this paper, the holistic and current applications of S. filicaulis were synthesized and critically discussed by summarizing, for the first time, its botany, traditional medicinal uses, active components, and pharmacological properties. We employed the databases of ScienceDirect, Scopus, Online Wiley library, PubMed, and Google Scholar to retrieve data on S. filicaulis from inception till February 2024, resulting in more than 70 electronic references. Based on literature reports, S. filicaulis has rich ethnopharmacological uses in different disease areas but their scientific validations are still in early stage, or not verified yet. In general, 16 phytochemicals have been identified so far. They include spilanthol, piperine, erucic acid, and isoquinoline derivative among others. The plant extracts possess anticancer, antioxidant, antimicrobial, anti-inflammatory, hepato-protective, anthelminthic, and analgesic activities. In the future, the phytochemical components, and biological activities of S. filicaulis need to be further investigated. Similarly, mechanistic studies need to be incorporated to the biological testing, to uncover the modes of actions of the species extracts and active components. Considering the species' rich ethnopharmacological applications, and the dearth of robust and established toxicity reports, the study on the safety of S. filicaulis would be an interesting and rewarding approach for further research.


Asunto(s)
Asteraceae , Etnofarmacología , Extractos Vegetales , Humanos , Extractos Vegetales/farmacología , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , Asteraceae/química , Animales , Medicina Tradicional , Plantas Medicinales/química , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoterapia
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