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1.
Nat Prod Rep ; 41(9): 1346-1367, 2024 Sep 18.
Artículo en Inglés | MEDLINE | ID: mdl-38717742

RESUMEN

Covering 2016 up to the end of 2023Alpinia is the largest genus of flowering plants in the ginger family, Zingiberaceae, and comprises about 500 species. Many Alpinia are commonly cultivated ornamental plants, and some are used as spices or traditional medicine to treat inflammation, hyperlipidemia, and cancers. However, only a few comprehensive reviews have been published on the phytochemistry and pharmacology of this genus, and the latest review was published in 2017. In this review, we provide an extensive coverage of the studies on Alpinia species reported from 2016 through 2023, including newly isolated compounds and potential biological effects. The present review article shows that Alpinia species have a wide spectrum of pharmacological activities, most due to the activities of diarylheptanoids, terpenoids, flavonoids, and phenolics.


Asunto(s)
Alpinia , Flavonoides , Fitoquímicos , Alpinia/química , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Estructura Molecular , Flavonoides/farmacología , Flavonoides/química , Flavonoides/aislamiento & purificación , Terpenos/farmacología , Terpenos/química , Terpenos/aislamiento & purificación , Humanos , Diarilheptanoides/farmacología , Diarilheptanoides/química , Diarilheptanoides/aislamiento & purificación , Fenoles/farmacología , Fenoles/química
2.
Metab Brain Dis ; 39(6): 1065-1084, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38954241

RESUMEN

The growing incidence of diabetes mellitus (DM) and depression is a global public health issue. Alpiniae oxyphyllae Fructus (AOF) is a kind of medicinal and edible plant which be found with anti-diabetic property, and could improve depression-like symptoms. This study aimed to screen active targets and potential mechanisms of AOF in treating DM with depression. Injection of streptozotocin (STZ) and exposure to chronic unpredictable mild stress (CUMS) for 4 weeks were used to conduct the DM with depression mice model. Behavioral tests, indexes of glucose metabolism, monoamine neurotransmitters, inflammatory cytokine and oxidative stress were measured. Histopathological change of hippocampus tissue was observing by HE and Nissl staining. UPLC-Q-Exactive Orbitrap/MS, network pharmacology and molecular docking were used to explore the chemical components and mechanisms of AOF on the DM with depression. AOF showed a reversed effect on body weight in DM with depression mice. Glucose metabolism and insulin resistance could be improved by treatment of AOF. In addition, AOF could alleviate depression-like behaviors based on the results of behavior tests and monoamine neurotransmitters. AOF also attenuated STZ-CUMS induced neuron injury in hippocampus. Next, a total of 61 chemical components were identified in the UPLC-Q-Exactive Orbitrap/MS analysis of the extract of AOF. Network pharmacology analysis suggested that 12 active components and 227 targets were screened from AOF, and 1802 target genes were screened from DM with depression, finally 126 intersection target genes were obtained. Drug-disease targets network was constructed and implied that the top five components with a higher degree value includes quercetin, nootkatone, baicalein, (-)-epicatechin and nootkatol. Protein-protein interaction (PPI) network showed that MAPK1, FOS, AKT1, IL6 and TP53 may be the core intersection targets. The mechanism of the effect of AOF on DM with depression was analyzed through gene ontology (GO), and kyoto encyclopedia of genes and genomes (KEGG) enrichment analysis, mainly involved in AGE/RAGE, PI3K/AKT, and MAPK signaling pathways. The results of molecular docking indicated that quercetin, nootkatone, baicalein, (-)-epicatechin and nootkatol all had good binding to the core intersection targets. Overall, our experimental researches have demonstrated that AOF could exert the dual effects of anti-diabetic and anti-depression on DM with depression mice, through multi-targets and multi-pathways.


Asunto(s)
Alpinia , Depresión , Diabetes Mellitus Experimental , Simulación del Acoplamiento Molecular , Farmacología en Red , Animales , Ratones , Masculino , Depresión/tratamiento farmacológico , Depresión/metabolismo , Diabetes Mellitus Experimental/tratamiento farmacológico , Alpinia/química , Extractos Vegetales/farmacología , Extractos Vegetales/uso terapéutico , Cromatografía Líquida de Alta Presión , Hipocampo/efectos de los fármacos , Hipocampo/metabolismo , Antidepresivos/uso terapéutico , Antidepresivos/farmacología
3.
Altern Ther Health Med ; 30(5): 6-13, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38581340

RESUMEN

Objectives: Continuous and excessive secretion of pro-inflammatory and anti-inflammatory chemicals and cytokines may further deteriorate inflammation. Anti-inflammatory drugs play an imperative role in inhibiting the evolution of inflammatory diseases. As per the Unani doctrine, a holistic treatment approach is used to treat illnesses. Therefore, drugs having different actions are used to achieve the synergic effect. Three drugs (Cinnamomum zeylanicum, Alpinia galanga, and Withania somnifera), which are frequently used in Unani medicine for joint disorders were selected to evaluate the anti-inflammatory activity of the extract derived from them. Methods: We used RAW 264.7 macrophage cells to see the expression of inflammatory markers IL-1ß, IL-6, and TNF-α. Cytotoxic activity was assessed with MTT assay and Nitric Oxide (NO) was evaluated using Griess reagent. Further, anti-inflammatory activity was evaluated in Wistar Albino rats using carrageenan-induced paw oedema and immunohistochemistry assays for Cyclooxygenase-2 (COX-2). All the data were analyzed using ANOVA and Dunnett t test for multiple comparisons. Results: This extract did not show any cytotoxic effect and the gene expression was significantly reduced for IL-1ß, IL-6, and TNF-α in a dose-dependent manner. Further, NO production was also significantly reduced in the test groups. Immunohistochemistry revealed that the test groups had less inflammation as compared to the control group. Conclusion: It may be inferred that the ethanolic extract of the three herbs has strong anti-inflammatory activity in the tested inflammatory models and the extract is safe as it did not show any cytotoxic effects in both in vitro and in vivo conditions.


Asunto(s)
Alpinia , Antiinflamatorios , Cinnamomum zeylanicum , Extractos Vegetales , Ratas Wistar , Withania , Animales , Withania/química , Extractos Vegetales/farmacología , Antiinflamatorios/farmacología , Ratas , Alpinia/química , Ratones , Cinnamomum zeylanicum/química , Células RAW 264.7 , Masculino , Edema/tratamiento farmacológico , Carragenina
4.
Arch Pharm (Weinheim) ; 357(10): e2400383, 2024 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-39031533

RESUMEN

Glucagon-like peptide-1 (GLP-1) secretagogues are fascinating pharmacotherapies to overcome the defects of GLP-1 analogs and dipeptidyl peptidase-4 (DPP-4) inhibitors in treating diabetes and obesity. To discover new GLP-1 secretagogues from natural sources, alpigalangols A-Q (1-17), 17 new labdane diterpenoids including four unusual nor-labdane and N-containing ones, were isolated from the fruits of Alpinia galanga. Most of the isolates showed GLP-1 promotive effects in NCl-H716 cells, of which compounds 3, 4, 12, and 14-17 were revealed with high promoting rates of 246.0%-413.8% at 50 µM. A mechanistic study manifested that the most effective compound 12 upregulated the mRNA expression of Gcg and Pcsk1, and the protein phosphorylation of PKA, CREB, and GSK3ß, but was inactive on GPBAR and GPR119 receptors. Network pharmacology analysis indicated that the PI3K-Akt pathway was involved in the GLP-1 stimulation of 12, which was highly associated with AKT1, CASP3, PPARG, and ICAM1 proteins. This study suggests that A. galanga is rich in diverse labdane diterpenoids with GLP-1 promoting effects, representing a new type of antidiabetic candidates from natural sources.


Asunto(s)
Alpinia , Proteínas Quinasas Dependientes de AMP Cíclico , Diterpenos , Péptido 1 Similar al Glucagón , Fosfatidilinositol 3-Quinasas , Proteínas Proto-Oncogénicas c-akt , Transducción de Señal , Alpinia/química , Diterpenos/farmacología , Diterpenos/química , Diterpenos/aislamiento & purificación , Humanos , Proteínas Proto-Oncogénicas c-akt/metabolismo , Proteínas Proto-Oncogénicas c-akt/antagonistas & inhibidores , Péptido 1 Similar al Glucagón/metabolismo , Transducción de Señal/efectos de los fármacos , Fosfatidilinositol 3-Quinasas/metabolismo , Proteínas Quinasas Dependientes de AMP Cíclico/metabolismo , Proteína de Unión a Elemento de Respuesta al AMP Cíclico/metabolismo , Relación Estructura-Actividad , Frutas/química , Estructura Molecular , Relación Dosis-Respuesta a Droga
5.
Bioprocess Biosyst Eng ; 47(8): 1183-1196, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38509420

RESUMEN

With the advent of nanotechnology, the treatment of cancer is changing from a conventional to a nanoparticle-based approach. Thus, developing nanoparticles to treat cancer is an area of immense importance. We prepared silver nanoparticles (AgNPs) from methanolic extract of Alpinia galanga rhizome and characterized them by UV-Vis spectrophotometry, Fourier transform Infrared (FTIR) spectroscopy, Zetasizer, and Transmission electron Microscopy (TEM). UV-Vis spectrophotometry absorption spectrum showed surface plasmon between 400 and 480 nm. FTIR spectrum analysis implies that various phytochemicals/secondary metabolites are involved in the reduction, caping, and stabilization of AgNPs. The Zetasier result suggests that the particles formed are small in size with a low polydispersity index (PDI), suggesting a narrow range of particle distribution. The TEM image suggests that the particles formed are mostly of spherical morphology with nearly 20-25 nm. Further, the selected area electron diffraction (SAED) image showed five electron diffraction rings, suggesting the polycrystalline nature of the particles. The nanoparticles showed high anticancer efficacy against cervical cancer (SiHa) cell lines. The nanostructures showed dose-dependent inhibition with 40% killing observed at 6.25 µg/mL dose. The study showed an eco-friendly and cost-effective approach to the synthesis of AgNPs and provided insight into the development of antioxidant and anticancer agents.


Asunto(s)
Alpinia , Antineoplásicos , Tecnología Química Verde , Nanopartículas del Metal , Extractos Vegetales , Plata , Plata/química , Alpinia/química , Nanopartículas del Metal/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Humanos , Antineoplásicos/química , Antineoplásicos/farmacología , Línea Celular Tumoral , Metanol/química , Espectroscopía Infrarroja por Transformada de Fourier
6.
J Microencapsul ; 41(5): 327-344, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38829223

RESUMEN

AIM: The work reports a novel nanophytosomal gel encapsulating Alpinia galanga (L.) Willd leaf essential oil to treat periodontal infections. METHODS: Alpinia oil-loaded nanophytosomes (ANPs) were formulated by lipid layer hydration technique and were evaluated by FESEM, cryo-TEM, loading efficiency, zeta potential, particle size, release profile etc. Selected ANPs-loaded gel (ANPsG) was evaluated by both in vitro and in vivo methods. RESULTS: Selected ANPs were spherical, unilamellar, 49.32 ± 2.1 nm size, 0.45 PDI, -46.7 ± 0.8 mV zeta potential, 9.8 ± 0.5% (w/w) loading, 86.4 ± 3.02% (w/w) loading efficiency with sustained release profile. ANPsG showed good spreadability (6.8 ± 0.3 gm.cm/sec), extrudability (79.33 ± 1.5%), viscosity (36522 ± 0.82 cps), mucoadhesive strength (44.56 ± 3.5 gf) with sustained ex vivo release tendency. Satisfied ZOI and MIC was observed for ANPsG against periodontal bacteria vs. standard/control. ANPsG efficiently treated infection in ligature induced periodontitis model. Key pharmacokinetic parameters like AUC, MRT, Vd were enhanced for ANPsG. CONCLUSION: ANPsG may be investigated for futuristic clinical studies.


Asunto(s)
Alpinia , Geles , Aceites Volátiles , Hojas de la Planta , Aceites Volátiles/química , Aceites Volátiles/administración & dosificación , Aceites Volátiles/farmacocinética , Aceites Volátiles/farmacología , Alpinia/química , Animales , Geles/química , Hojas de la Planta/química , Antibacterianos/farmacocinética , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/administración & dosificación , Enfermedades Periodontales/tratamiento farmacológico , Masculino , Nanopartículas/química , Ratas , Periodontitis/tratamiento farmacológico , Simulación por Computador
7.
Molecules ; 29(12)2024 Jun 14.
Artículo en Inglés | MEDLINE | ID: mdl-38930910

RESUMEN

Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm is a perennial plant of the Zingiberaceae family widely distributed in the subtropical and tropical areas of South America, Oceania, and Asia. Multiple plant parts of A. zerumbet have been traditionally used as medicinal sources, each with different clinical uses. These variations may arise from differences among the chemical components and/or accumulations of the active compounds in each part. Therefore, this review summarizes previous studies on the phytochemicals in A. zerumbet and reveals the similarities and differences among the chemical constituents of its multiple medicinal parts, including the leaves, rhizomes, fruits, seeds, and flowers. The results contribute to the scientific validation of the traditional understanding that A. zerumbet possesses different medicinal properties in each plant part. In addition, this review provides directions for further studies on the phytochemicals of this plant.


Asunto(s)
Alpinia , Fitoquímicos , Alpinia/química , Fitoquímicos/química , Extractos Vegetales/química , Humanos , Plantas Medicinales/química
8.
Molecules ; 29(16)2024 Aug 18.
Artículo en Inglés | MEDLINE | ID: mdl-39202984

RESUMEN

Alpinae oxyphyllae fructus (AOF), the dried mature fruit of Alpinia oxyphylla Miquel of the Zingiberaceae family, shows many special pharmacological effects. In recent years, there has been an abundance of research results on AOF. In this paper, the new compounds isolated from AOF since 2018 are reviewed, including terpenes, flavonoids, diarylheptanoids, phenolic acid, sterols, alkanes, fats, etc. The isolation methods that were applied include the microwave-assisted method, response surface method, chiral high-performance liquid chromatography-multiple reaction monitoring-mass spectrometry (HPLC-MRM-MS) analytical method, ultra-high-performance liquid chromatography-quadrupole-electrostatic field orbitrap high-resolution mass spectrometry (UPLC-Orbitrap-HRMS) method, ultra-high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method, hot water leaching method, ethanol leaching method, and so on. Additionally, the pharmacological effects of AOF found from 2018 to 2024 are also summarized, including neuroprotection, regulation of metabolic disorders, antioxidant activity, antiapoptosis, antiinflammatory activity, antidiabetic activity, antihyperuricemia, antiaging, antidiuresis, immune regulation, anti-tumor activity, renal protection, hepatoprotection, and anti-asthma. This paper provides a reference for further research on AOF.


Asunto(s)
Alpinia , Alpinia/química , Humanos , Extractos Vegetales/química , Extractos Vegetales/farmacología , Frutas/química , Animales , Cromatografía Líquida de Alta Presión/métodos , Flavonoides/química , Flavonoides/farmacología , Flavonoides/farmacocinética , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/farmacocinética , Fitoquímicos/química , Fitoquímicos/farmacología , Fitoquímicos/farmacocinética , Espectrometría de Masas en Tándem/métodos
9.
Molecules ; 29(8)2024 Apr 16.
Artículo en Inglés | MEDLINE | ID: mdl-38675630

RESUMEN

AHP-3a, a triple-helix acidic polysaccharide isolated from Alpinia officinarum Hance, was evaluated for its anticancer and antioxidant activities. The physicochemical properties and structure of AHP-3a were investigated through gel permeation chromatography, scanning electron microscopy (SEM), Fourier transform infrared spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. The weight-average molecular weight of AHP-3a was 484 kDa, with the molar percentages of GalA, Gal, Ara, Xyl, Rha, Glc, GlcA, and Fuc being 35.4%, 21.4%, 16.9%, 11.8%, 8.9%, 3.1%, 2.0%, and 0.5%, respectively. Based on the results of the monosaccharide composition analysis, methylation analysis, and NMR spectroscopy, the main chain of AHP-3a was presumed to consist of (1→4)-α-D-GalpA and (1→2)-α-L-Rhap residues, which is a pectic polysaccharide with homogalacturonan (HG) and rhamnogalacturonan-I (RG-I) structural domains containing side chains. In addition, the results of the antioxidant activity assay revealed that the ability of AHP-3a to scavenge DPPH, ABTS, and OH free radicals increased with an increase in its concentration. Moreover, according to the results from the EdU, wound healing, and Transwell assays, AHP-3a can control the proliferation, migration, and invasion of HepG2 and Huh7 hepatocellular carcinoma cells without causing any damage to healthy cells. Thus, AHP-3a may be a natural antioxidant and anticancer component.


Asunto(s)
Alpinia , Antioxidantes , Compuestos de Bifenilo , Polisacáridos , Alpinia/química , Polisacáridos/química , Polisacáridos/farmacología , Polisacáridos/aislamiento & purificación , Humanos , Antioxidantes/farmacología , Antioxidantes/química , Proliferación Celular/efectos de los fármacos , Antineoplásicos/farmacología , Antineoplásicos/química , Células Hep G2 , Peso Molecular , Línea Celular Tumoral , Monosacáridos/análisis , Monosacáridos/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Picratos/química , Picratos/antagonistas & inhibidores , Espectroscopía Infrarroja por Transformada de Fourier
10.
Cell Mol Biol (Noisy-le-grand) ; 69(2): 12-18, 2023 Feb 28.
Artículo en Inglés | MEDLINE | ID: mdl-37224052

RESUMEN

Hepatic cancer was the third most prevalent cause of cancer-related death worldwide in 2018, and its incidence is increasing. While therapeutic agents for hepatic cancer have improved, these agents can cause serious side effects, including damage to healthy tissues. To overcome this limitation, more than 3,000 plants have been used globally as common alternatives for cancer treatment. The anti-cancer activity of Alpinia japonica, one of the traditional herbal medicines (Korean name: Kkot-yang-ha), was investigated. Water extract of A. japonica (AJ) decreased the cell viability of hepatic cancer cells. AJ extract showed greater than 70% loss of mitochondrial potential in HepG2 cells as demonstrated by JC-1 staining. Apoptosis was induced by treatment with AJ extract as shown through FACS analysis, and G0/G1 phase arrest of 76.66% HepG2 cells was confirmed through cell cycle analysis and quantitative RT-PCR. Improper regulation of ERK1/2 might contribute to cell death, and JNK activation is necessary for apoptosis induced by stress stimuli. AJ extract stimulated the phosphorylation of JNK and ERK1/2, mitogen-activated protein kinases (MAPKs), in HepG2 cells. AJ extract has anticancer activity by inhibiting cell cycle progression, leading to apoptosis of hepatic cancer cells. This extract could potentially be used as a therapeutic agent for hepatic cancer.


Asunto(s)
Alpinia , Carcinoma Hepatocelular , Neoplasias Hepáticas , Extractos Vegetales , Alpinia/química , Apoptosis , Carcinoma Hepatocelular/tratamiento farmacológico , Puntos de Control de la Fase G1 del Ciclo Celular , Neoplasias Hepáticas/tratamiento farmacológico , Humanos , Células Hep G2 , Extractos Vegetales/farmacología
11.
Bioorg Chem ; 134: 106431, 2023 05.
Artículo en Inglés | MEDLINE | ID: mdl-36857933

RESUMEN

The phytochemical investigation of the fruits of Alpinia oxyphylla led to the isolation and identification of 40 structurally diverse sesquiterpenoids, including 17 new eudesmane sesquiterpenoids (1-17) and 23 known analogues (18-40). Among the isolates, 14 and 17 were unusual rearranged eudesmane sesquiterpenoids, featuring rare 5/6-fused and 6/8-fused bicyclic carbon skeleton, respectively; 15 and 16 were the novel 6,7-seco-eudesmane sesquiterpenoids isolated from plant-origin for the first time, 1 and 3-6 were rare nor-eudesmane sesquiterpenoids. Their structures were elucidated by comprehensive spectroscopic data analysis (NMR, HRESIMS, IR, UV), single crystal X-ray diffraction, and quantum chemistry calculations (ECD and 13C NMR). Moreover, all isolates were evaluated by measuring their inhibitory effect on nitric oxide (NO) in LPS-stimulated BV-2 cells. As a result, compounds 11, 20, 24 and 40 showed moderate to strong inhibition on NO productions, with IC50 values ranging from 21.63 to 60.70 µM. Meanwhile, these compounds also partially decreased the secretion of TNF-α and IL-6 in LPS-stimulated BV-2 cells. Furthermore, 20 could down-regulate protein expressions (COX-2 and iNOS) and observably inhibit the mRNA expressions of TNF-α, IL-6, COX-2 and iNOS. In this study, the discovery of structurally diverse anti-inflammatory sesquiterpenoids from the fruits of A. oxyphylla could benefit the further development and utilization of this plant.


Asunto(s)
Alpinia , Sesquiterpenos de Eudesmano , Sesquiterpenos , Frutas/química , Alpinia/química , Factor de Necrosis Tumoral alfa , Lipopolisacáridos/farmacología , Ciclooxigenasa 2 , Interleucina-6 , Antiinflamatorios/farmacología , Sesquiterpenos de Eudesmano/farmacología , Sesquiterpenos de Eudesmano/química , Sesquiterpenos/farmacología , Sesquiterpenos/química , Estructura Molecular
12.
J Sep Sci ; 46(14): e2300156, 2023 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-37147276

RESUMEN

In this paper, an off-line combination method of supercritical fluid extraction and supercritical fluid chromatography was developed for the selective extraction and isolation of diphenylheptanes and flavonoids from Alpinia officinarum Hance. The enrichment of target components was successfully achieved using supercritical fluid extraction with the following conditions (8% ethanol as co-solvent at 45°C and 30 MPa for 30 min). Taking full advantage of the complementarity of supercritical fluid chromatography stationary phases, a two-step preparative supercritical fluid chromatography strategy was constructed. The extract was firstly divided into seven fractions on a Diol column (250 × 20 mm internal diameter, 10 µm) within 8 min by gradient elution increasing from 5% to 20% modifier (methanol) at 55 ml/min and 15 MPa. Then the seven fractions were separated by using a 1-AA or a DEA column (250 × 19 mm internal diameter, 5 µm) at 50 ml/min and 13.5 MPa. This two-step strategy showed superior separation ability for structural analogs. As a result, seven compounds, including four diphenylheptanes and three flavonoids with high purity, were successfully obtained. The developed method is also helpful for the extraction and isolation of other structural analogs of traditional Chinese medicines.


Asunto(s)
Alpinia , Cromatografía con Fluido Supercrítico , Cromatografía con Fluido Supercrítico/métodos , Alpinia/química , Flavonoides , Solventes/química , Metanol/química
13.
Chem Biodivers ; 20(12): e202301269, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37964691

RESUMEN

Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm. was extensively used in traditional medicine for its several properties, but continuous investigation is needed to discover the properties of its essential oils (EOs). This work evaluated the properties of an EO obtained by steam distillation (named ESD) as well as extracts obtained by petroleum ether (named EP) both from Alpinia zerumbet fruits. Gas chromatography-mass spectrometry (GC-MS) was chosen to identify the composition, and eleven compounds were identified as the main components of the EO and EP of Alpinia zerumbet fruits. The antimicrobial properties were investigated by minimum inhibitory concentration (MIC) and the inhibition area. The results identified the differences in antimicrobial activities attributed to different extraction methods. Enzyme-linked immunosorbent assay (ELISA) and Western Blot (WB) assay were conducted to assess the anti-inflammatory effects of ESD. In conclusion, our study suggested that EO from Alpinia zerumbet fruits might be a prospective candidate for antimicrobial and anti-inflammatory therapy.


Asunto(s)
Alpinia , Antiinfecciosos , Aceites Volátiles , Aceites Volátiles/farmacología , Aceites Volátiles/química , Alpinia/química , Frutas , Antiinfecciosos/farmacología , Antiinflamatorios/farmacología
14.
Bioorg Chem ; 120: 105653, 2022 03.
Artículo en Inglés | MEDLINE | ID: mdl-35149263

RESUMEN

Ten new diarylheptanoid dimers, katsumadainols C1 - C10 (1-10), were isolated from the seeds of Alpinia katsumada and elucidated by extensive spectroscopic methods, ECD calculations, and single-crystal X-ray diffraction. Their antidiabetic effects were evaluated by the stimulation of GLP-1 secretion in STC-1 cells and inhibition against four diabetes-related enzymes, GPa, α-glucosidase, PTP1B, and DPP4. Compounds 1-5 and 7-10 significantly stimulated GLP-1 secretion by 267.5-433.1% (25.0 µM) and 117.8-348.2% (12.5 µM). Compounds 1-4 exhibited significant inhibition on GPa with IC50 values of 18.0-31.3 µM; compounds 1-5 showed obvious inhibition on α-glucosidase with IC50 values of 6.9-18.2 µM; compounds 1-5 and 10 possessed PTP1B inhibitory activity with IC50 values ranging from 35.5 to 80.1 µM. This investigation first disclosed compounds 1-4 as intriguing GLP-1 secretagogues and GPa, α-glucosidase, and PTP1B inhibitors, which provided valuable clues for searching multiple-target antidiabetic candidates from Zingiberaceae plants.


Asunto(s)
Alpinia , Alpinia/química , Diarilheptanoides/química , Diarilheptanoides/farmacología , Inhibidores Enzimáticos/farmacología , Péptido 1 Similar al Glucagón , Inhibidores de Glicósido Hidrolasas/farmacología , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Extractos Vegetales/química , Secretagogos , alfa-Glucosidasas
15.
Planta Med ; 88(2): 163-178, 2022 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-33445186

RESUMEN

Estrogen receptor-positive breast cancer patients have a good prognosis, but 30% of these patients will experience recurrence due to the development of resistance through various signaling pathways. This study aimed to evaluate the mode of anticancer effects of 1'-acetoxychavicol acetate, which is isolated from the rhizomes of Alpinia galanga in estrogen receptor positive (MCF7) human epidermal growth factor receptor 2-overexpressed (MCF7/HER2), and endocrine-resistant breast cancer cells (MCF7/LCC2 and MCF7/LCC9). 1'-Acetoxychavicol acetate showed antiproliferation in a concentration- and time-dependent fashion and had higher potency in human epidermal growth factor receptor 2-overexpressed cell lines. This was associated with down-regulation of human epidermal growth factor receptor 2, pERK1/2, pAKT, estrogen receptor coactivator, cyclin D1, and MYC proto-oncogene while in vivo and significant reduction in the tumor mass of 1'-acetoxychavicol acetate-treated zebrafish-engrafted breast cancer groups. The anti-invasive effects of 1'-acetoxychavicol acetate were confirmed in vitro by the matrigel invasion assay and with down-regulation of C - X-C chemokine receptor type 4, urokinase plasminogen activator, vascular endothelial growth factor, and basic fibroblast growth factor 2 genes. The down-regulation of urokinase plasminogen activator and fibroblast growth factor 2 proteins was also validated by molecular docking analysis. Moreover, 1'-acetoxychavicol acetate-treated cells exhibited lower expression levels of the anti-apoptotic Bcl-2 and Mcl-1 proteins in addition to enhanced stress-activated kinases/c-Jun N-terminal kinase 1/2 and poly-ADP ribose polymerase cleavage, indicating apoptotic cell induction by 1'-acetoxychavicol acetate. Moreover, 1'-acetoxychavicol acetate had higher potency in human epidermal growth factor receptor 2-overexpressed cell lines regarding its inhibition on human epidermal growth factor receptor 2, pAKT, pERK1/2, PSer118, and PSer167-ERα proteins. Our findings suggest 1'-acetoxychavicol acetate mediates its anti-cancer effects via human epidermal growth factor receptor 2 signaling pathway.


Asunto(s)
Alpinia , Apoptosis , Alcoholes Bencílicos/farmacología , Neoplasias de la Mama , Alpinia/química , Animales , Neoplasias de la Mama/tratamiento farmacológico , Proliferación Celular , Femenino , Humanos , Células MCF-7 , Simulación del Acoplamiento Molecular , Transducción de Señal , Pez Cebra
16.
Lett Appl Microbiol ; 75(2): 281-292, 2022 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-35313037

RESUMEN

Essential oils encapsulated in a polymeric matrix can be used as an alternative method to control fungi and mycotoxins. The essential oils were extracted by hydrodistillation and characterized by gas chromatography. The nanofibres were produced from poly (acid lactic) (PLA) containing essential oils by the Solution Blow Spinning method. The antifungal and antimicotoxygenic properties were evaluated against Aspergillus ochraceus and Aspergillus westerdijkiae by the fumigation method. Terpinen-4-ol (20·23%), sabinene (20·18%), 1·8-cineole (16·69%) and γ-terpinene (11·03%) were the principal compounds present in the essential oil from Alpinia speciosa, whereas citral (97·67%) was dominant from Cymbopogon flexuosus. Microscopy images showed that the addition of essential oils caused an increase in the diameter of the nanofibres. The infrared spectroscopy results indicated the presence of essential oils in the PLA nanofibres. Differential scanning calorimetry curves also indicated the existence of interactions between the essential oils and polymeric macromolecules through their plasticizing action. The hydrophobic character of nanofibres was revealed by the contact angle technique. An antifungal effect was observed, the mycelial growths (3·25-100%) and the synthesis of ochratoxin A (25·94-100%) were inhibited by the presence of the nanofibres. The results suggest that bioactive nanofibres hold promise for application to control toxigenic fungi.


Asunto(s)
Alpinia , Cymbopogon , Nanofibras , Aceites Volátiles , Alpinia/química , Antifúngicos/farmacología , Aspergillus , Cymbopogon/química , Hongos , Aceites Volátiles/química , Aceites Volátiles/farmacología , Poliésteres
17.
Int J Mol Sci ; 23(7)2022 Apr 03.
Artículo en Inglés | MEDLINE | ID: mdl-35409351

RESUMEN

Yakuchinone A (1) is a bioactive diarylheptanoid isolated from the dried fruits of Alpinia oxyphylla. Microbial transformation has been recognized as an efficient method to produce new biologically active derivatives from natural products. In the present study, microbial transformation of yakuchinone A was performed with the fungus Mucor hiemalis KCTC 26779, which led to the isolation of nine new metabolites (2, 3a, 3b, and 4-9). Their structures were elucidated as (3S)-oxyphyllacinol (2), (3S,7R)- and (3S,7S)-7-hydroxyoxyphyllacinol (3a and 3b), (3S)-oxyphyllacinol-4'-O-ß-d-glucopyranoside (4), (3S)-4″-hydroxyoxyphyllacinol (5), (3S)-3″-hydroxyoxyphyllacinol (6), (3S)-2″-hydroxyoxyphyllacinol (7), (3S)-2″-hydroxyoxyphyllacinol-2″-O-ß-d-glucopyranoside (8), and (3S)-oxyphyllacinol-3-O-ß-d-glucopyranoside (9) based on the comprehensive spectroscopic analyses and the application of modified Mosher's method. All compounds were evaluated for their cytotoxic activities against melanoma, as well as breast, lung, and colorectal cancer cell lines. Compound 9, which was O-glucosylated on the diarylheptanoid alkyl chain, exhibited the most selective cytotoxic activities against melanoma cell lines with the IC50 values ranging from 6.09 to 9.74 µM, indicating that it might be considered as a possible anti-cancer lead compound.


Asunto(s)
Alpinia , Melanoma , Alpinia/química , Diarilheptanoides , Frutas , Humanos , Estructura Molecular , Extractos Vegetales/química
18.
Molecules ; 27(10)2022 May 19.
Artículo en Inglés | MEDLINE | ID: mdl-35630752

RESUMEN

This study aimed to investigate the chemical composition and reveal the selective inhibitory activity of Alpinia galanga (L.) Willd. essential oil (AGO) on acetylcholinesterase (AChE) compared to butyrylcholinesterase (BChE). The chemical composition of AGO was investigated by means of gas chromatography-mass spectrometry. Ellman's method was used to determine the inhibitory activities against AChE and BChE. Microemulsion systems with desirable anticholinesterase effects were developed. Methyl cinnamate and 1,8-cineole were reported as the major component of AGO. The IC50 values of A. galanga oil against AChE and BChE were 24.6 ± 9.6 and 825.4 ± 340.1 µg/mL, respectively. The superior selectivity of AGO on AChE (34.8 ± 8.9) compared to galantamine hydrobromide (6.4 ± 1.5) suggested AGO to be an effective ingredient with fewer side effects for Alzheimer's treatment. Interestingly, the microemulsion of AGO possessed significantly higher anticholinesterase activity than that of native oil alone. Therefore, microemulsion of AGO is a promising alternative approach for the treatment of Alzheimer's disease.


Asunto(s)
Alpinia , Aceites Volátiles , Acetilcolinesterasa , Alpinia/química , Butirilcolinesterasa , Inhibidores de la Colinesterasa/química , Aceites Volátiles/química , Aceites Volátiles/farmacología
19.
Molecules ; 27(13)2022 Jul 05.
Artículo en Inglés | MEDLINE | ID: mdl-35807553

RESUMEN

The rhizomes of Alpinia officinarum Hance (known as the smaller galangal) have been used as a traditional medicine for over 1000 years. Nevertheless, little research is available on the bacteriostatic activity of the herb rhizomes. In this study, we employed, for the first time, a chloroform and methanol extraction method to investigate the antibacterial activity and components of the rhizomes of A. officinarum Hance. The results showed that the growth of five species of pathogenic bacteria was significantly inhibited by the galangal methanol-phase extract (GMPE) (p < 0.05). The GMPE treatment changed the bacterial cell surface hydrophobicity, membrane fluidity and/or permeability. Comparative transcriptomic analyses revealed approximately eleven and ten significantly altered metabolic pathways in representative Gram-positive Staphylococcus aureus and Gram-negative Enterobacter sakazakii pathogens, respectively (p < 0.05), demonstrating different antibacterial action modes. The GMPE was separated further using a preparative high-performance liquid chromatography (Prep-HPLC) technique, and approximately 46 and 45 different compounds in two major component fractions (Fractions 1 and 4, respectively) were identified using ultra-HPLC combined with mass spectrometry (UHPLC-MS) techniques. o-Methoxy cinnamaldehyde (40.12%) and p-octopamine (62.64%) were the most abundant compounds in Fractions 1 and 4, respectively. The results of this study provide data for developing natural products from galangal rhizomes against common pathogenic bacteria.


Asunto(s)
Alpinia , Zingiberaceae , Alpinia/química , Antibacterianos/análisis , Antibacterianos/farmacología , Metanol/análisis , Extractos Vegetales/química , Rizoma/química
20.
Ceska Slov Farm ; 71(3): 103-115, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-36058639

RESUMEN

This study aimed to determine the amount of energy to damage the red galangal rhizome sliced cell tissue and the amount and quality of the essential oil obtained by steam-water distillation. This study was a randomized block design, with pulsed electric field (PEF) voltage treatment starting at 1000, 2000, 3000, 4000, and 5000 V and without PEF and repeated three times. The results showed that the voltage between 3000 and 4000 V (E = 120-160 V/cm) or equivalent to 271.5-365.0 kJ/cm3 had damaged the red galangal rhizome slice cell tissue. The increase in yield due to PEF ranged from 13% to 73%, and there was no change in the value of the refractive index and specific gravity, but there was a change in the chemical composition of the essential oil constituents. The benefits of research with PEF treatment are the increase in yield and shorter distillation time.


Asunto(s)
Alpinia , Aceites Volátiles , Alpinia/química , Rizoma
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