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1.
Phytochemistry ; 220: 114008, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38346545

RESUMO

From the 95% ethanol aqueous extract of the roots of Clausena lansium, six previously undescribed alkaloids (1, 2a, 2b, 15, 24a, 24b), a pair of prenylated phenylpropenols (26a, 26b), two coumarins (27, 28), and two undescribed sesquiterpenes (37, 38) were isolated and identified using spectroscopic and electron circular dichroism data, together with thirty-two known compounds. The absolute configurations of three alkaloids (3a, 3b, 4a) were determined for the first time. In vitro assay showed that alkaloids 7, 10, 12, 19, and furanocoumarins 34, 35 displayed inhibitory effects on the production of nitric oxide in lipopolysaccharide (LPS)-induced BV-2 microglial cells, which were stronger than that of the minocycline (positive control). RT-PCR results indicated that indizoline (7) could inhibit the expression of pro-inflammatory factors (IL-1ß, TNF-α, and IL-6) in LPS-treated BV-2 cells.


Assuntos
Alcaloides , Clausena , Estrutura Molecular , Clausena/química , Microglia , Lipopolissacarídeos/farmacologia , Carbazóis/química , Alcaloides/química , Óxido Nítrico
2.
Int J Biol Macromol ; 254(Pt 3): 128029, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-37952330

RESUMO

Four main water-soluble wampee fruit pulp polysaccharides, named CSP-I, CSP-II, CSP-III and CSP-IV, were isolated from Clausena lansium (Lour.) Skeels Guifei, therein CSP-IV content was higher than the others. All components possess certain anticoagulant activity demonstrated by prolonged activated partial thromboplastin time, especially CSP-IV, which suggests that CSP-IV plays anticoagulant effect through disturbing intrinsic coagulation pathway. The wampee polysaccharide CSP-IV with Mw of 510.1 kDa was mainly composed of Gal, Ara and GalA. Backbone of CSP-IV contains Gal, Ara and GalA, two kinds of side chains contain one monosaccharide Gal or Ara, both branch on Gal residue of backbone. CSP-IV has no the conformation of triple helix demonstrated by Congo red test. These results showed that CSP-IV is an acidic polysaccharide with potential anticoagulant activity via targeting intrinsic coagulation pathway.


Assuntos
Clausena , Frutas , Frutas/química , Água/análise , Polissacarídeos/química , Anticoagulantes/farmacologia
3.
Molecules ; 28(24)2023 Dec 12.
Artigo em Inglês | MEDLINE | ID: mdl-38138542

RESUMO

Infections caused by Candida albicans (C. albicans) and increasing resistance to commonly used drugs lead to a variety of mucosal diseases and systemic infectious diseases. We previously confirmed that the essential oil of Clausena lansium (Lour.) Skeels seeds (CSEO) had antifungal activity against C. albicans, but the detailed mechanism between the chemical components and antifungal activity is unclear. In this study, a quantitative analysis of five volatile components of CSEO, including sabinene, α-phellandrene, ß-phellandrene, 4-terpineol, and ß-caryophyllene, was carried out using the gas chromatography-mass spectrometry (GC-MS) method. Both the broth dilution and kinetic growth methods proved that the antifungal activity of CSEO against fluconazole-resistant C. albicans was better than that of its main components (sabinene and 4-terpineol). To further investigate the inhibitory mechanism, the transcriptional responses of C. albicans to CSEO, sabinene, and 4-terpineol treatment were determined based on RNA-seq. The Venn diagram and clustering analysis pattern of differential expression genes showed the mechanism of CSEO and 4-terpineol's anti-C. albicans activity might be similar from the perspective of the genes. Functional enrichment analysis suggested that CSEO regulated adherence-, hyphae-, and biofilm-formation-related genes, which may be CSEO's active mechanism of inhibiting the growth of fluconazole-resistant C. albicans. Overall, we preliminarily revealed the molecular mechanism between the chemical components and the antifungal activity of CSEO against C. albicans. This study provides new insights to overcome the azole resistance of C. albicans and promote the development and application of C. lansium (Lour.) Skeels seeds.


Assuntos
Clausena , Óleos Voláteis , Candida albicans/genética , Óleos Voláteis/química , Antifúngicos/química , Clausena/química , Cromatografia Gasosa-Espectrometria de Massas , Fluconazol , RNA-Seq , Sementes/química , Perfilação da Expressão Gênica , Testes de Sensibilidade Microbiana
4.
Food Chem Toxicol ; 181: 114087, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37804914

RESUMO

Wampee (Clausena lansium) is a common fruit in South Asia. The pulp is a tasty food, and the seed is a typical traditional herb in China. However, we identified a primary toxic compound, Lansamide I, by NMR and X-ray diffraction of single-crystal. The compound occurred at 4.17 ± 0.16 mg/kg of dried seed and 0.08 ± 0.01 g/kg of fresh fruit. In our phenotype-based toxicity investigation, the compound caused decreased hatchability of zebrafish eggs, increased malformations such as enlarged yolk sacs and pericardial edema, and delayed body length development. Moreover, the compound also caused nerve cell damage and decreased locomotor activity. The compound caused an increase in peroxidation levels in vivo, with increases in both malondialdehyde and superoxide dismutase levels, but did not interfere with acetylcholinesterase levels. Metabolomic studies found that the compound caused significant up-regulation of 16 metabolites, mainly amino acids and peptides, which were involved in the nucleotide metabolism pathway and the betaine biosynthesis module. The qRT-PCR revealed that the substance interfered with the mRNA expression of tat and dctpp. These discoveries offer fresh perspectives on the toxicity mechanisms and metabolic response to the primary harmful molecules in wampee, which could inform the rational usage of wampee resources.


Assuntos
Clausena , Animais , Clausena/química , Frutas/química , Acetilcolinesterase , Peixe-Zebra , Extratos Vegetais/análise
5.
Int J Biol Macromol ; 253(Pt 8): 127683, 2023 Dec 31.
Artigo em Inglês | MEDLINE | ID: mdl-37890311

RESUMO

Chitosan (Ch)-based edible composite films were prepared by incorporating blending wampee seed essential oil (WSEO) into a Ch matrix, using the incorporation ratio as a variable. The physical, mechanical properties, structure morphology and rheological properties were determined using tensile strength (TS), elongation at break (EB), water vapor permeability (WVP) tests together with Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM) observations and apparent viscosity and shear rate. In addition, the antimicrobial, antioxidant activities were investigated by the DPPH & ABTS radicals scavenging and inhibition zone assays, respectively. Compared with Ch, the incorporation of WSEO significantly decreased (P < 0.05) the TS, EB, and WVP values, especially when the WSEO ratio reached 1.0 % or higher. Meanwhile, the films exhibited greatly improved visible light barrier performance after WSEO incorporation. Both FTIR spectroscopy and SEM observations reflected the crosslinking between WSEO and Ch. Meanwhile, the composite films demonstrated smaller particle size and weaker rheological viscosities, which enhanced the antimicrobial and antioxidant capabilities when compared with those of Ch. Therefore, this study suggested that WSEO incorporated with Ch is an effective ingredient for the preparation of edible films with enhanced physicochemical and biological properties.


Assuntos
Anti-Infecciosos , Quitosana , Clausena , Filmes Comestíveis , Óleos Voláteis , Antioxidantes/farmacologia , Antioxidantes/química , Óleos Voláteis/farmacologia , Quitosana/química , Anti-Infecciosos/farmacologia , Permeabilidade , Embalagem de Alimentos
6.
Food Res Int ; 173(Pt 1): 113274, 2023 11.
Artigo em Inglês | MEDLINE | ID: mdl-37803586

RESUMO

To investigate the changes in phenolics, flavonoids, and their bio-activities of wampee (Clausena lansium (Lour.) Skeels) during digestion, the peel and pulp were subjected to simulated in vitro digestion, encompassing oral, gastric, small intestine, and large intestine digestion stages. The peel exhibited a total release of 91.93 mg GAE/g DW of phenolics and 61.86 mg RE/g DW of flavonoids, whereas the pulp displayed a release of 27.83 mg GAE/g DW of phenolics and 8.94 mg RE/g DW of flavonoids. Notably, the phenolics and flavonoids were mostly released during the oral digestion stage for peel, while they were mostly released during the small intestine digestion stage for pulp. The results of the targeted flavonoids analysis indicated that rutin and l-epicatechin were the two most widely released compounds in each digestion step. Moreover, myricetin has been identified as the best inhibitor against α-glucosidase, probably because it formed the most H-bonds, 8, with 6 catalytic residues, which was the highest number. Furthermore, the soluble substances released from the peel exhibited significantly higher antioxidant activities and inhibitory activity against α-glucosidase (p < 0.05) compared to those from the pulp. Positive correlations were observed between the total phenolic content or total flavonoid content and the antioxidant activities (r > 0.73 (peel), > 0.61 (pulp)), as well as α-glucosidase inhibitory activity (r <  - 0.48 (peel), < -0.64 (pulp)) of peel and pulp. In conclusion, these findings provide valuable insights into the digestive characteristics and health benefits of both wampee peel and pulp.


Assuntos
Antioxidantes , Clausena , Antioxidantes/farmacologia , Antioxidantes/química , Clausena/química , alfa-Glucosidases , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Fenóis/química , Flavonoides/química , Digestão
7.
Malar J ; 22(1): 264, 2023 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-37689679

RESUMO

BACKGROUND: The erythrocytic stage of the life cycle of the malaria parasite, Plasmodium falciparum, consists of trophozoite, schizont and gametocyte stages in humans. Various anti-malarial agents target different stages of the parasite to produce treatment outcomes. This study reports on the stage-specific anti-malarial activity of heptaphylline and imperatorin against human P. falciparum in addition to their cytotoxicity and selectivity indices (SI). METHODS: The compounds were isolated from Clausena anisata using column chromatography and their structures elucidated using NMR spectroscopy. The anti-malarial activity was determined by measuring the trophozoitocidal, schizonticidal and gametocytocidal activities of the compounds using the SYBR green assay. Cytotoxicity was evaluated using the tetrazolium-based colorimetric assay. RESULTS: Heptaphylline and imperatorin produced trophozoitocidal, schizonticidal and gametocytocidal activities with IC50s of 1.57 (0.2317)-26.92 (0.3144) µM with those of artesunate (the standard drug) being 0.00024 (0.0036)-0.0070 (0.0013) µM. In the cytotoxicity assay, the compounds produced CC50S greater than 350 µM and SI of 13.76-235.90. Also, the trophozoitocidal and schizonticidal activities of the compounds were more pronounced than their gametocytocidal activity. Imperatorin was 42.04% more trophozoitocidal than hepthaphyline. However, hepthaphyline has more schizonticidal and gametocytocidal properties than imperatorin. CONCLUSION: Heptaphylline and imperatorin are promising anti-malarial agents, since they possess potent anti-malarial activity with weak cytotoxicity on RBCs. However, imperatorin is a better anti-malarial prophylactic agent whereas heptaphylline is a better malaria treatment agent.


Assuntos
Alcaloides , Antimaláricos , Antiprotozoários , Clausena , Furocumarinas , Malária Falciparum , Parasitos , Humanos , Animais , Antimaláricos/farmacologia , Furocumarinas/farmacologia , Malária Falciparum/tratamento farmacológico
8.
Molecules ; 28(14)2023 Jul 14.
Artigo em Inglês | MEDLINE | ID: mdl-37513285

RESUMO

Induced by the spread of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), the COVID-19 pandemic underlined the clear need for antivirals against coronaviruses. In an effort to identify new inhibitors of SARS-CoV-2, a screening of 824 extracts prepared from various parts of 400 plant species belonging to the Rutaceae and Annonaceae families was conducted using a cell-based HCoV-229E inhibition assay. Due to its significant activity, the ethyl acetate extract of the leaves of Clausena harmandiana was selected for further chemical and biological investigations. Mass spectrometry-guided fractionation afforded three undescribed phenolic lipids (1-3), whose structures were determined via spectroscopic analysis. The absolute configurations of 1 and 2 were determined by analyzing Mosher ester derivatives. The antiviral activity against SARS-CoV-2 was subsequently shown, with IC50 values of 0.20 and 0.05 µM for 2 and 3, respectively. The mechanism of action was further assessed, showing that both 2 and 3 are inhibitors of coronavirus entry by acting directly on the viral particle. Phenolic lipids from Clausena harmandiana might be a source of new antiviral agents against human coronaviruses.


Assuntos
COVID-19 , Clausena , Humanos , SARS-CoV-2 , Clausena/química , Pandemias , Antivirais/farmacologia , Folhas de Planta , Lipídeos
9.
Planta Med ; 89(12): 1165-1169, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37414059

RESUMO

Clausena excavata is a medicinal plant widely distributed in Southeast Asia. It is used for a variety of indications, including to treat malaria. In our present study, a phytochemical study of the methanol extract from the stem bark of C. excavata led to the isolation of five pyranocoumarins, nordentatin (1: ), dentatin (2: ), kinocoumarin (3: ), clausarin (4: ), and clausenidin (5: ), and a coumarin, 8-hydroxy-3″,4″-dihydrocapnolactone-2',3'-diol (6: ). The isolation of compound 6: from C. excavata and the antiplasmodial activities against a multidrug-resistant K1 strain of Plasmodium falciparum of 1, 3: , and 5: were reported for the first time. Compounds 3: and 4: exhibited potent antiplasmodial activities with EC50 values of 1.10 and 0.58 µM, respectively, while 1: and 5: had EC50 values of 5.62 and 7.15 µM, respectively. A prenyl group attached to the C-3 or C-12 position on the pyranocoumarin ring probably plays an important role on the activity. A hydroxyl group at the C-10 position is also likely to enhance the activity.


Assuntos
Antimaláricos , Clausena , Plantas Medicinais , Clausena/química , Antimaláricos/farmacologia , Antimaláricos/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Casca de Planta , Plantas Medicinais/química , Plasmodium falciparum
10.
Sci Rep ; 13(1): 6053, 2023 04 13.
Artigo em Inglês | MEDLINE | ID: mdl-37055457

RESUMO

Anti-oxidant stress is a potential strategy for the treatment of ischemic stroke. Here, we found a novel free radical scavenger termed as CZK, which is derived from alkaloids contained in Clausena lansium. In this study, we first compared cytotoxicity and biological activity between CZK and its parent's compound Claulansine F. It was found that CZK had lower cytotoxicity and improved anti-oxygen-glucose deprivation/reoxygenation (OGD/R) injury than its parent's compound. Free radical scavenging test showed that CZK had a strong inhibitory effect on hydroxyl free radicals with the IC50 of 77.08 nM. Intravenous injection of CZK (50 mg/kg) significantly alleviated ischemia-reperfusion injury, manifested by reduced neuronal damage and decreased oxidative stress. Consistent with the findings, the activities of superoxide dismutase (SOD) and reduced glutathione (GSH) were increased. Molecular docking predicted that CZK might be combined with nuclear factor erythroid 2-related factor 2 (Nrf2) complex. Our results also confirmed that CZK upregulated the contents of Nrf2 and its target gene products Heme Oxygenase-1 (HO-1), and NAD(P)H: Quinone Oxidoreductase 1 (NQO1). In conclusion, CZK had a potential therapeutic effect for ischemic stroke by activating Nrf2-mediated antioxidant system.


Assuntos
Alcaloides , Clausena , AVC Isquêmico , Traumatismo por Reperfusão , Antioxidantes/farmacologia , Antioxidantes/uso terapêutico , Fator 2 Relacionado a NF-E2/metabolismo , AVC Isquêmico/tratamento farmacológico , Simulação de Acoplamento Molecular , Estresse Oxidativo , Heme Oxigenase-1/metabolismo , Alcaloides/farmacologia , Traumatismo por Reperfusão/tratamento farmacológico , Glucose/farmacologia , Apoptose
11.
Pest Manag Sci ; 79(8): 2675-2685, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-36889932

RESUMO

BACKGROUND: The rational utilization of botanical secondary metabolites is one of the strategies to reduce the application of chemical fungicides. The extensive biological activities of Clausena lansium indicate that it has the potential to develop botanical fungicides. RESULTS: A systematic investigation on the antifungal alkaloids from C. lansium branch-leaves following bioassay-guided isolation was implemented. Sixteen alkaloids, including two new and nine known carbazole alkaloids, one known quinoline alkaloid and four known amides, were isolated. Compounds 4, 7, 12 and 14 showed strong antifungal activity on Phytophthora capsiciwith EC50 values ranging from 50.67 to 70.82 µg mL-1 . Compounds 1, 3, 8, 10, 11, 12 and 16 displayed different degrees of antifungal activity against Botryosphaeria dothidea with EC50 values ranging from 54.18 to 129.83 µg mL-1 . It was reported for the first time that these alkaloids had antifungal effects on P. capsici or B. dothidea, and their structure-activity relationships were further discussed systematically. Additionally, among all alkaloids, dictamine (12) had the strongest antifungal activities against P. capsici (EC50  = 50.67 µg mL-1 ) and B. dothidea (EC50  = 54.18 µg mL-1 ), and its physiological effects on P. capsici and B. dothidea also were further evaluated. CONCLUSION: Capsicum lansium is a potential source of antifungal alkaloids, and C. lansium alkaloids had the potential as lead compounds of botanical fungicides in the development of new fungicides with novel action mechanism. © 2023 Society of Chemical Industry.


Assuntos
Alcaloides , Clausena , Fungicidas Industriais , Rutaceae , Clausena/química , Antifúngicos/farmacologia , Estrutura Molecular , Fungicidas Industriais/farmacologia , Fungicidas Industriais/análise , Alcaloides/farmacologia , Alcaloides/química , Folhas de Planta/química
12.
Plant Dis ; 107(5): 1613-1616, 2023 May.
Artigo em Inglês | MEDLINE | ID: mdl-36444142

RESUMO

Pantoea anthophila CL1 is a causal agent of soft rot disease in Clausena lansium (wampee) in China and has inhibitory activity against the bacterial wilt pathogen Ralstonia solanacearum. Here we report the genome sequencing and analysis of P. anthophila CL1, representing the first complete genome resource of the species. The CL1 genome consists of four circular replicons (one chromosome and three plasmids), with a total size of 4,594,065 bp, and contains 4,109 protein-coding genes and 106 RNA genes. Our bioinformatic analysis of CL1 predicted 228 virulence factors, two Type VI Secretion Systems, and six secondary metabolite biosynthesis gene clusters producing saccharides, siderophores, and terpene. The complete genome sequence of P. anthophila CL1 provides a solid foundation for further investigation of its pathogenesis and antimicrobial activity and also represents a valuable resource for the comparative genomics of Pantoea.


Assuntos
Clausena , Pantoea , Pantoea/genética , Clausena/genética , Genômica , Genoma Bacteriano/genética
13.
Sci Rep ; 12(1): 9978, 2022 06 15.
Artigo em Inglês | MEDLINE | ID: mdl-35705583

RESUMO

Anethole, a widely used industrial flavoring agent is majorly sourced from anise and star anise. The present study is aimed to the in-depth pharmacological analysis i.e. anti-diabetic, skin whitening, neurodegenerative disorder inhibitory activities of anethole-rich Clausena heptaphylla leaf essential oil (ARCHEO) (88.59%) as revealed by the Gas Chromatography/Mass Spectrometry (GC/MS) analysis and further confirmed by proton nuclear magnetic resonance 1H-NMR as well as to compare with standard compound anethole. ARCHEO (ABTS EC50 6.97 ± 0.004 µg/mL; Protease assay 4.51 ± 0.004 µg/mL) outperformed the standard compound anethole (ABTS EC50 9.48 ± 0.048 µg/mL; Protease assay EC50 22.64 ± 0.016 µg/mL) in antioxidant and anti-inflammatory experiments. ARCHEO was also shown to be more effective than the reference compound anethole in terms of anti-diabetic activity (EC50 22.35 ± 0.121 µg/mL), tyrosinase inhibitory activity (EC50 16.45 ± 0.012 µg/mL), and anti-cholinesterase activity (EC50 22.32 ± 0.016 µg/mL). However, ARCHEO exhibited lower antimicrobial activity towards all the tested microbes compared to standard compound anethole and as for the MIC, ARCHEO was effective only towards Salmonella typhimurium (60 µg/mL), Streptococcus mutans (20 µg/mL), and Aspergillus fumigatus (75 µg/mL). ARCHEO (11.11%) and anethole (12.33%) showed no genotoxic effect based on Allium cepa assay mitotic index value. Thus, ARCHEO could be a commercially viable and widely available cheaper source of anethole, which has buoyant demand in the field of food flavoring, fragrance, and pharmaceutical industries.


Assuntos
Clausena , Óleos Voláteis , Derivados de Alilbenzenos , Anisóis , Dano ao DNA , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Peptídeo Hidrolases
14.
Food Chem ; 386: 132834, 2022 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-35509166

RESUMO

Effects of different extraction acids on physicochemical, structural, and functional properties of wampee fruit peel pectin (WFPP) were comparatively investigated. The hydrochloric acid extracted WFPP (HEP) exhibited the highest degrees of methylation (67.79%) and acetylation (86.29%) coupling with abundant monosaccharides and rhamnogalacturonan branches, but lowest molecular weight (5.58 × 105 Da). The results of SEM, X-ray diffraction, and Fourier transform infrared spectroscopy analyses showed that acid types had little effect on the surface morphology of WFPP. However, compared to commercial citrus pectin (CCP), several specific absorbance peaks (1539, 1019, 920 cm-1) were found in WFPPs, which corresponds to aromatic skeletal stretching, pyranose, and d-glucopyranosyl, respectively. Moreover, the rheological behavior revealed that WFPP solution was pseudoplastic fluid and affected by acid types. And the WFPPs exhibited higher emulsifying activity and emulsion stability than CCP. All these WFPPs presented well antioxidant activity and promoting probiotics ability, especially for HEP.


Assuntos
Clausena , Antioxidantes/análise , Clausena/química , Emulsões/química , Frutas/química , Compostos Orgânicos/análise , Pectinas/química
15.
BMC Complement Med Ther ; 22(1): 108, 2022 Apr 19.
Artigo em Inglês | MEDLINE | ID: mdl-35439990

RESUMO

BACKGROUND: Alzheimer's disease (AD) pathogenesis is associated with amyloid-ß (Aß)-induced neuroinflammation. In AD, the activation of microglia caused by Aß accumulation is followed by the synthesis and release of pro-inflammatory cytokines, including interleukin-1ß (IL-1ß) and tumor necrosis factor-α (TNFα), and ultimately leads to cognitive impairments. Clausena harmandiana (CH) is a medicinal plant in the Rutaceae family and has been used in folk medicine to relieve illnesses such as stomachache and headache, and as a health tonic. Interestingly, CH root extract (CHRE) has several anti-inflammatory and other pharmacological activities, but there are no studies in AD-like animal models. OBJECTIVES: This study aims to evaluate the effects of CHRE on cognitive impairments, increased Aß1-42 protein levels, and neuroinflammation in Aß1-42-induced rats. METHODS: Forty-eight adult male Sprague-Dawley rats (250-300 g) were randomly divided into 6 groups (n = 8) of the sham control, V + Aß, CB + Aß CHRE125 + Aß, CHRE250 + Aß, and CHRE500 + Aß. Sodium carboxymethylcellulose, Celebrex (10 mg/kg BW) and CHRE (125, 250, and 500 mg/kg BW) were given orally or without any treatment for 35 days. On day 21, aggregated Aß1-42 at a concentration of 1 µg/µl were injected into both lateral ventricles (1 µl/side) of all treated rats, while sterilized normal saline were injected to untreated rats. Ten days later, the novel object recognition test was performed to assess their recognition memory. At the end of the test period, an overdose of thiopental sodium (120 mg/kg BW) and transcardial perfusion with 0.9% normal saline solution were used to euthanize all rats. Then Aß1-42 protein levels and the expression of inflammatory markers (CD11b-positive microglia, IL-1ß, and TNFα) were investigated in the cerebral cortex and hippocampus. RESULTS: Pretreatment with CHRE at all doses could attenuate short- and long-term impairments in recognition memory. Additionally, CHRE also inhibited the increase of Aß1-42 protein levels and the expression of inflammatory markers in both brain regions as well as receiving Celebrex. CONCLUSIONS: This suggests that preventive treatment of CHRE might be a potential therapy against cognitive impairments via reducing Aß1-42 protein levels and neuroinflammation caused by Aß1-42.


Assuntos
Doença de Alzheimer , Clausena , Disfunção Cognitiva , Doença de Alzheimer/tratamento farmacológico , Peptídeos beta-Amiloides/toxicidade , Animais , Celecoxib , Clausena/metabolismo , Disfunção Cognitiva/tratamento farmacológico , Modelos Animais de Doenças , Masculino , Doenças Neuroinflamatórias , Fragmentos de Peptídeos/toxicidade , Extratos Vegetais/uso terapêutico , Ratos , Ratos Sprague-Dawley , Fator de Necrose Tumoral alfa/metabolismo
16.
Molecules ; 27(6)2022 Mar 18.
Artigo em Inglês | MEDLINE | ID: mdl-35335333

RESUMO

Clausena lenis Drake (C. lenis) is a folk medicinal herb to treat influenza, colds, bronchitis, and malaria. The 95% and 50% ethanol extract of C. lenis showed significant nitric oxide (NO) inhibition activity in BV-2 microglial cells stimulated by lipopolysaccharide (LPS). Bio-guided isolation of the active extract afforded five new compounds, including a chlorine-containing furoquinoline racemate, (±)-claulenine A (1), an amide alkaloid, claulenine B (2), a prenylated coumarin, claulenin A (3), a furocoumarin glucoside, clauleside A (4), and a multi-prenylated p-hydroxybenzaldehyde, claulenin B (5), along with 33 known ones. Their structures were determined via spectroscopic methods, and the absolute configurations of new compounds were assigned via the electronic circular dichroism (ECD) calculations and single-crystal X-ray diffraction analysis. Compounds 2, 23, 27, 28, 33, and 34 showed potent anti-neuroinflammatory effects on LPS-induced NO production in BV-2 microglial cells, with IC50 values in the range of 17.6-40.9 µM. The possible mechanism was deduced to interact with iNOS through molecular docking.


Assuntos
Clausena , Linhagem Celular , Microglia , Simulação de Acoplamento Molecular , Óxido Nítrico
17.
Molecules ; 27(3)2022 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-35164038

RESUMO

Essential oils (EOs) of Clausena indica fruits, Zanthoxylum rhetsa fruits, and Michelia tonkinensis seeds were analyzed for their phytochemical profiles and biological activities, including anti-diabetes, anti-gout, and anti-leukemia properties. Sixty-six volatile compounds were identified by gas chromatography-mass spectrometry (GC-MS), in which, myristicin (68.3%), limonene (44.2%), and linalool (49.3%) were the most prominent components of EOs extracted from C. indica, Z. rhetsa, and M. tonkinensis, respectively. In addition, only EOs from C. indica inhibited the activities of all tested enzymes comprising α-amylase (IC50 = 7.73 mg/mL), α-glucosidase (IC50 = 0.84 mg/mL), and xanthine oxidase (IC50 = 0.88 mg/mL), which are related to type 2 diabetes and gout. Remarkably, all EOs from C. indica, Z. rhetsa (IC50 = 0.73 mg/mL), and M. tonkinensis (IC50 = 1.46 mg/mL) showed a stronger anti-α-glucosidase ability than acarbose (IC50 = 2.69 mg/mL), a known anti-diabetic agent. Moreover, the growth of leukemia cell Meg-01 was significantly suppressed by all EOs, of which, the IC50 values were recorded as 0.32, 0.64, and 0.31 mg/mL for EOs from C. indica, Z. rhetsa, and M. tonkinensis, respectively. As it stands, this is the first report about the inhibitory effects of EOs from C. indica and Z. rhetsa fruits, and M. tonkinensis seeds on the human leukemia cell line Meg-01 and key enzymes linked to diabetes and gout. In conclusion, the present study suggests that EOs from these natural spices may be promising candidates for pharmaceutical industries to develop nature-based drugs to treat diabetes mellitus or gout, as well as malignant hematological diseases such as leukemia.


Assuntos
Antineoplásicos/uso terapêutico , Clausena/química , Supressores da Gota/uso terapêutico , Hipoglicemiantes/uso terapêutico , Leucemia/tratamento farmacológico , Magnoliaceae/química , Óleos Voláteis/uso terapêutico , Zanthoxylum/química , Humanos , Óleos Voláteis/química
18.
Nat Prod Res ; 36(2): 501-507, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-32643406

RESUMO

In this work, we isolated a new benzofuran glycoside, 6-ß-d-glucosyl-6,7-dihydroxy-5-benzofuranpropanoic acid methyl ester (1), together with six known compounds (2-7) from the fruits of Clausena lansium (Lour.) Skeels. Extensive spectroscopic methods were employed to elucidate their structures. Herein, compounds 2, 3, 5 and 6 were reported from Clausena lansium (Lour.) Skeels for the first time. Moreover, compounds 1, 2, 4 and 6 showed comparable 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical scavenging activity to l-ascorbic acid, and compound 4 also exhibited potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and ferric reducing antioxidant power (FRAP). All of the compounds showed oxygen radical absorbance capacity (ORAC) values ranging from 0.3 to 3.6 µmol trolex equivalent/µmol. In addition, compounds 3 and 5 also demonstrated good α-amylase inhibitory activity.


Assuntos
Benzofuranos , Clausena , Antioxidantes , Benzofuranos/farmacologia , Frutas , Glicosídeos/farmacologia
19.
Int J Biol Macromol ; 194: 412-421, 2022 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-34813784

RESUMO

Pectins have proven to be advantageous for human health as they regulate beneficial microbial communities and enhance immunity. The fruit of Clausena lansium (Lour.) Skeels (Wampee), also referred to as "treasure in fruit", is rich in pectin polysaccharides. In this study, a homogalacturonan-type pectin (CCP2) with a molecular weight of 8.9 × 104 Da and degree of esterification of 42.86% was isolated from Wampee fruit. The gut microbiota regulation and phagocytosis-enhancing properties of CCP2 were examined in vivo and in vitro, respectively. Oral administration of CCP2 dramatically decreased the abundance of Bacteroidetes and increased the abundance of Firmicutes in intestinal bacteria in mice. The content of short-chain fatty acids in the feces also significantly improved. Moreover, CCP2 exhibited excellent phagocytosis-enhancing activities on RAW 264.7 macrophages. These results suggested that CCP2 could be a potential gut microbiota regulator and phagocytosis-enhancer, which could be used in food products to promote health through beneficial manipulation of gut microbiota.


Assuntos
Clausena/metabolismo , Frutas/metabolismo , Microbioma Gastrointestinal/efeitos dos fármacos , Pectinas/uso terapêutico , Prebióticos/microbiologia , Animais , Animais não Endogâmicos , Camundongos , Células RAW 264.7
20.
J Appl Biomed ; 19(1): 40-47, 2021 03.
Artigo em Inglês | MEDLINE | ID: mdl-34907714

RESUMO

CONTEXT: Clausena excavata Burm. f is a plant used in folklore medicine for the treatment of various ailments in South East Asia. The plant parts contain chemical components that are cytotoxic to many cancer cells. OBJECTIVE: The study investigated the cytotoxic effects of ethyl acetate, methanol and chloroform C. excavata leaf extracts on the non-small-lung cancer, NCI-H460, cell line. METHODS: Based on the 3-(4,5-dimethylthiazol-2-yl)-2,5,-diphenyltetrazolium bromide (MTT) assay, among extracts, ethyl acetate C. excavata leaf extract (EACE) was the most potent anti-NCI-H460 cells, with IC50 value of 47.1 ± 6.1 µg/ml. The effects of EACE on NCI-H460 cells were also determined by clonogenic, 4', 6-diamidino-2-phenylindole (DAPI), and annexin-V-fluorescein isothiocyanate/propidium iodide-PI flow cytometric assays. Reactive oxygen species (ROS) production and apoptotic gene expressions was determined via flow cytometry and real-time quantitative PCR, respectively. RESULTS: EACE-treated NCI-H460 cells after 48 h underwent apoptosis as evident by loss of cell viability, cell shrinkage, and chromatin condensation. The results also showed EACE mediated increase in ROS production by the NCI-H460 cells. After 48 h treatment, EACE increased the pro-apoptotic BAX and decreased the anti-apoptotic Bcl-2, Survivin and c-Myc gene expressions. CONCLUSIONS: EACE is a potential anti-lung cancer by increasing cancer cell ROS production and apoptosis.


Assuntos
Clausena , Neoplasias Pulmonares , Acetatos , Apoptose , Linhagem Celular , Clausena/metabolismo , Neoplasias Pulmonares/tratamento farmacológico , Espécies Reativas de Oxigênio/metabolismo
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