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  1 / 648 MEDLINE  
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PMID:28813645
Autor:Tan JW; Israf DA; Md Hashim NF; Cheah YK; Harith HH; Shaari K; Tham CL
Endereço:Department of Biomedical Science, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, Serdang 43300, Malaysia.
Título:LAT is essential for the mast cell stabilising effect of tHGA in IgE-mediated mast cell activation.
Fonte:Biochem Pharmacol; 144:132-148, 2017 Nov 15.
ISSN:1873-2968
País de publicação:England
Idioma:eng
Resumo:Mast cells play a central role in the pathogenesis of allergic reaction. Activation of mast cells by antigens is strictly dependent on the influx of extracellular calcium that involves a complex interaction between signalling molecules located within the cells. We have previously reported that tHGA, an active compound originally isolated from a local shrub known as Melicope ptelefolia, prevented IgE-mediated mast cell activation and passive systemic anaphylaxis by suppressing the release of interleukin-4 (IL-4) and tumour necrosis factor (TNF)-α from activated rat basophilic leukaemia (RBL)-2H3 cells. However, the mechanism of action (MOA) as well as the molecular target underlying the mast cell stabilising effect of tHGA has not been previously investigated. In this study, DNP-IgE-sensitised RBL-2H3 cells were pre-treated with tHGA before challenged with DNP-BSA. To dissect the MOA of tHGA in IgE-mediated mast cell activation, the effect of tHGA on the transcription of IL-4 and TNF-α mRNA was determined using Real Time-Polymerase Chain Reaction (qPCR) followed by Calcium Influx Assay to confirm the involvement of calcium in the activation of mast cells. The protein lysates were analysed by using Western Blot to determine the effect of tHGA on various important signalling molecules in the LAT-PLCγ-MAPK and PI3K-NFκB pathways. In order to identify the molecular target of tHGA in IgE-mediated mast cell activation, the LAT and LAT2 genes in RBL-2H3 cells were knocked-down by using RNA interference to establish a LAT/LAT2 competition model. The results showed that tHGA inhibited the transcription of IL-4 and TNF-α as a result of the suppression of calcium influx in activated RBL-2H3 cells. The results from Western Blot revealed that tHGA primarily inhibited the LAT-PLCγ-MAPK pathway with partial inhibition on the PI3K-p65 pathway without affecting Syk. The results from RNAi further demonstrated that tHGA failed to inhibit the release of mediators associated with mast cell degranulation under the LAT/LAT2 competition model in the absence of LAT. Collectively, this study concluded that the molecular target of tHGA could be LAT and may provide a basis for the development of a mast cell stabiliser which targets LAT.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Adaptor Proteins, Signal Transducing); 0 (Lat protein, rat); 0 (Membrane Proteins); 0 (Phosphoproteins); 0 (Plant Extracts); 37341-29-0 (Immunoglobulin E)


  2 / 648 MEDLINE  
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PMID:28763644
Autor:Aratikatla EK; Valkute TR; Puri SK; Srivastava K; Bhattacharya AK
Endereço:Division of Organic Chemistry, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune, 411 008, India; Academy of Scientific and Innovative Research (AcSIR), CSIR-NCL, Pune, 411 008, India.
Título:Norepinephrine alkaloids as antiplasmodial agents: Synthesis of syncarpamide and insight into the structure-activity relationships of its analogues as antiplasmodial agents.
Fonte:Eur J Med Chem; 138:1089-1105, 2017 Sep 29.
ISSN:1768-3254
País de publicação:France
Idioma:eng
Resumo:Syncarpamide 1, a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC values of 2.04 µM (D6 clone), 3.06 µM (W2 clone) and observed by us 3.90 µM (3D7 clone) and 2.56 µM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, (R)-2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds (3-57), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer (S)-58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, (S)-41 and its enantiomer, (R)-42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC values of 3.16, 2.28 µM (3D7) and 1.78, 2.07 µM (K1), respectively than the natural product, syncarpamide 1. Three compounds (S)-13, (S)-17, (S)-21 exhibited antiplasmodial activities with IC values of 6.39, 6.82, 6.41 µM against 3D7 strain, 4.27, 7.26, 2.71 µM against K1 strain and with CC values of 147.72, 153.0, >200 µM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1. The natural product syncarpamide 1 and four analogues/homologues out of the synthesized library of 55, (S)-41, (R)-42, (S)-55 and (S)-57 were assayed in vivo assay against chloroquine-resistant P. yoelii (N-67) strain of Plasmodium. However, none of the five molecules, 1, (S)-41, (R)-42, (S)-55 and (S)-57 exhibited any promising in vivo antimalarial activity against P. yoelii (N-67) strain. Compounds 4, 6, 7 and 11 showed high cytotoxicities with CC values of 5.87, 5.08, 6.44 and 14.04 µM, respectively. Compound 6 was found to be the most cytotoxic as compared to the standard drug, podophyllotoxin whereas compounds 4 and 7 showed comparable cytotoxicities to podophyllotoxin.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Alkaloids); 0 (Antimalarials); X4W3ENH1CV (Norepinephrine)


  3 / 648 MEDLINE  
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PMID:28762091
Autor:Sarker SD; Nahar L
Endereço:Medicinal Chemistry and Natural Products Research Group, School of Pharmacy and Biomolecular Sciences, Faculty of Science, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK. S.Sarker@ljmu.ac.uk.
Título:Progress in the Chemistry of Naturally Occurring Coumarins.
Fonte:Prog Chem Org Nat Prod; 106:241-304, 2017.
ISSN:2191-7043
País de publicação:Austria
Idioma:eng
Resumo:Coumarins are the largest group of 1-benzopyran derivatives found in plants. The initial member of this group of compounds, coumarin (2H-1-benzopyran-2-one), a fragrant colorless compound, was first isolated from the Tonka bean (Dipteryx odorata, family Fabaceae) in 1820. The name coumarin comes from a French term for the tonka bean, coumarou. Since the discovery of coumarin, several of its derivatives, with umbelliferone (7-hydroxycoumarin) being the most common one, have been reported from various natural sources. The families Apiaceae, Asteraceae, and Rutaceae are the three major plant sources of coumarins.Generally, these plant secondary metabolites may be classified into simple, simple prenylated, simple geranylated, furano, pyrano, sesquiterpenyl and oligomeric coumarins. Using this standard classification, this chapter aims to present an account on the advances of the chemistry of naturally occurring coumarins, as reported in the literature during the period 2013-2015.In Sect. 1, the coumarins are introduced and their generic biosynthetic route discussed briefly. In Sect. 2, the largest of the three sections, various classes of natural coumarins are detailed, with their relevant structures and the citation of appropriate references. In a concluding section, it is highlighted that during the last 3 years, more than 400 coumarins have been reported in the literature. Many of these coumarins have been re-isolations of known compounds from known or new sources, most often associated with various biological activities. However, a substantial number of coumarins bearing new skeletons, especially dimers, prenylated furanocoumarins, sesquiterpenyl, and some unusual coumarins were also reported during the period of 2013-2015.Coumarin chemistry remains one of the major interest areas of phytochemists, especially because of their structural diversity and medicinal properties, along with the wide-ranging bioactivities of these compounds, inclusive of analgesic, anticoagulant anti-HIV, anti-inflammatory, antimicrobial, antineoplastic, antioxidant, and immunomodulatory effects. Despite significant advancements in the extraction, isolation, structure elucidation and bioactivity testing of naturally occurring coumarins, only a marginal advancement has been observed recently in relation to the study of their biosynthesis.
Tipo de publicação: JOURNAL ARTICLE; REVIEW
Nome de substância:0 (Anti-Infective Agents); 0 (Antineoplastic Agents); 0 (Antioxidants); 0 (Coumarins); 0 (Plant Extracts)


  4 / 648 MEDLINE  
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PMID:28726400
Autor:Nguyen NT; Dang PH; Vu NXT; Le TH; Nguyen MTT
Endereço:Faculty of Chemistry, VNUHCM-University of Science , 227 Nguyen Van Cu Street, District 5, Ho Chi Minh City, Vietnam.
Título:Quinoliniumolate and 2H-1,2,3-Triazole Derivatives from the Stems of Paramignya trimera and Their α-Glucosidase Inhibitory Activities: In Vitro and in Silico Studies.
Fonte:J Nat Prod; 80(7):2151-2155, 2017 Jul 28.
ISSN:1520-6025
País de publicação:United States
Idioma:eng
Resumo:From a CHCl -soluble extract of the stems of Paramignya trimera, two new alkaloids, (E)-2-(prop-1-enyl)-N-methylquinolinium-4-olate (1) and (R)-2-ethylhexyl 2H-1,2,3-triazole-4-carboxylate (2), were isolated. Their structures were elucidated based on the spectroscopic data interpretation. Compound 2 possesses α-glucosidase inhibitory activity, with an IC value of 137.9 µM. Molecular docking studies of 1 and 2 with human maltase-glucoamylase (MGAM) were performed for the first time; thus, the 2,3-diH -1H-1,2,3-triazolium cation (2i) showed good interactions with both MGAM-N (2QMJ) and -C (3TOP) terminal subunits.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Alkaloids); 0 (Glycoside Hydrolase Inhibitors); 0 (Triazoles)


  5 / 648 MEDLINE  
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PMID:28693595
Autor:Al-Zuaidy MH; Mumtaz MW; Hamid AA; Ismail A; Mohamed S; Razis AFA
Endereço:Department of Food Science, Faculty of Food Science and Technology, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia.
Título:Biochemical characterization and H NMR based metabolomics revealed Melicope lunu-ankenda leaf extract a potent anti-diabetic agent in rats.
Fonte:BMC Complement Altern Med; 17(1):359, 2017 Jul 10.
ISSN:1472-6882
País de publicação:England
Idioma:eng
Resumo:BACKGROUND: Type 2 diabetes mellitus (T2DM) is a metabolic disorder characterized by continuous hyperglycemia associated with insulin resistance and /or reduced insulin secretion. There is an emerging trend regarding the use of medicinal plants for the treatment of diabetes mellitus. Melicope lunu-ankenda (ML) is one of the Melicope species belonging to the family Rutaceae. In traditional medicines, its leaves and flowers are known to exhibit prodigious health benefits. The present study aimed at investigating anti-diabetic effect of Melicope lunu-ankenda (ML) leaves extract. METHODS: In this study, anti-diabetic effect of ML extract is investigated in vivo to evaluate the biochemical changes, potential serum biomarkers and alterations in metabolic pathways pertaining to the treatment of HFD/STZ induced diabetic rats with ML extract using H NMR based metabolomics approach. Type 2 diabetic rats were treated with different doses (200 and 400 mg/kg BW) of Melicope lunu-ankenda leaf extract for 8 weeks, and serum samples were examined for clinical biochemistry. The metabolomics study of serum was also carried out using H NMR spectroscopy in combination with multivariate data analysis to explore differentiating serum metabolites and altered metabolic pathways. RESULTS: The ML leaf extract (400 mg/kg BW) treatment significantly increased insulin level and insulin sensitivity of obese diabetic rats, with concomitant decrease in glucose level and insulin resistance. Significant reduction in total triglyceride, cholesterol and low density lipoprotein was also observed after treatment. Interestingly, there was a significant increase in high density lipoprotein of the treated rats. A decrease in renal injury markers and activities of liver enzymes was also observed. Moreover, metabolomics studies clearly demonstrated that, ML extract significantly ameliorated the disturbance in glucose metabolism, tricarboxylic acid cycle, lipid metabolism, and amino acid metabolism. CONCLUSION: ML leaf extract exhibits potent antidiabetic properties, hence could be a useful and affordable alternative option for the management of T2DM.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Blood Glucose); 0 (Cholesterol, HDL); 0 (Hypoglycemic Agents); 0 (Insulin); 0 (Lipids); 0 (Plant Extracts); 0 (Triglycerides)


  6 / 648 MEDLINE  
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PMID:28614729
Autor:Fernandes TS; Copetti D; do Carmo G; Neto AT; Pedroso M; Silva UF; Mostardeiro MA; Burrow RE; Dalcol II; Morel AF
Endereço:Department of Chemistry, Federal University of Santa Maria, Rio Grande do Sul, Brazil.
Título:Phytochemical analysis of bark from Helietta apiculata Benth and antimicrobial activities.
Fonte:Phytochemistry; 141:131-139, 2017 Sep.
ISSN:1873-3700
País de publicação:England
Idioma:eng
Resumo:Extraction and characterization of natural products from the bark of the trunk of Helietta apiculata Benth (Rutaceae) afforded nine alkaloids, eight furoquinoline and one quinolone, limonine, three cinnamic acid derivatives, three neolignans, tetracosanoic acid, six coumarins, of which apiculin A and apiculin B (neolignans), and tanizin (coumarin) are previously undescribed compounds. The structures of all compounds were determined by spectroscopic methods, and the crystal structures of two of the newly undescribed compounds, apiculin A and apiculin B, were determined by X-ray analysis. Extracts and pure compounds isolated from Helietta apiculata showed promising antimicrobial activities.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Anti-Bacterial Agents); 0 (Antifungal Agents); 0 (Coumarins); 0 (Lignans); 0 (Phytochemicals); 0 (Plant Extracts)


  7 / 648 MEDLINE  
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PMID:28476158
Autor:Kabir MF; Mohd Ali J; Abolmaesoomi M; Hashim OH
Endereço:Department of Molecular Medicine, Faculty of Medicine, University of Malaya, 50603, Kuala Lumpur, WP, Malaysia.
Título:Melicope ptelefolia leaf extracts exhibit antioxidant activity and exert anti-proliferative effect with apoptosis induction on four different cancer cell lines.
Fonte:BMC Complement Altern Med; 17(1):252, 2017 May 05.
ISSN:1472-6882
País de publicação:England
Idioma:eng
Resumo:BACKGROUND: Melicope ptelefolia is a well-known herb in a number of Asian countries. It is often used as vegetable salad and traditional medicine to address various ailments. However, not many studies have been currently done to evaluate the medicinal benefits of M. ptelefolia (MP). The present study reports antioxidant, anti-proliferative, and apoptosis induction activities of MP leaf extracts. METHOD: Young MP leaves were dried, powdered and extracted sequentially using hexane (HX), ethyl acetate (EA), methanol (MeOH) and water (W). Antioxidant activity was evaluated using ferric reducing antioxidant power (FRAP), 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-Diphenyl-2-picryl-hydrazyl (DPPH) radicals scavenging and cellular antioxidant activity (CAA) assays. Anti-proliferative activity was evaluated through cell viability assay, using the following four human cancer cell lines: breast (HCC1937, MDA-MB-231), colorectal (HCT116) and liver (HepG2). The anti-proliferative activity was further confirmed through cell cycle and apoptosis assays, including annexin-V/7-aminoactinomycin D staining and measurements of caspase enzymes activation and inhibition. RESULT: Overall, MP-HX extract exhibited the highest antioxidant potential, with IC values of 267.73 ± 5.58 and 327.40 ± 3.80 µg/mL for ABTS and DPPH radical-scavenging assays, respectively. MP-HX demonstrated the highest CAA activity in Hs27 cells, with EC of 11.30 ± 0.68 µg/mL, while MP-EA showed EC value of 37.32 ± 0.68 µg/mL. MP-HX and MP-EA showed promising anti-proliferative activity towards the four cancer cell lines, with IC values that were mostly below 100 µg/mL. MP-HX showed the most notable anti-proliferative activity against MDA-MB-231 (IC = 57.81 ± 3.49 µg/mL) and HCT116 (IC = 58.04 ± 0.96 µg/mL) while MP-EA showed strongest anti-proliferative activity in HCT116 (IC = 64.69 ± 0.72 µg/mL). The anticancer potential of MP-HX and MP-EA were also demonstrated by their ability to induce caspase-dependent apoptotic cell death in all of the cancer cell lines tested. Cell cycle analysis suggested that both the MP-HX and MP-EA extracts were able to disrupt the cell cycle in most of the cancer cell lines. CONCLUSIONS: MP-HX and MP-EA extracts demonstrated notable antioxidant, anti-proliferative, apoptosis induction and cancer cell cycle inhibition activities. These findings reflect the promising potentials of MP to be a source of novel phytochemical(s) with health promoting benefits that are also valuable for nutraceutical industry and cancer therapy.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Plant Extracts)


  8 / 648 MEDLINE  
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PMID:28333075
Autor:Huang A; Xu H; Zhan R; Chen W; Liu J; Chi Y; Chen D; Ji X; Luo C
Endereço:Key Laboratory of Ministry of Education, Research Center of Chinese Herbal Resources and Engineering, Guangzhou University of Chinese Medicine, Guangzhou 510006, China. hah2008@gzucm.edu.cn.
Título:Metabolic Profile of Skimmianine in Rats Determined by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry.
Fonte:Molecules; 22(4), 2017 Mar 23.
ISSN:1420-3049
País de publicação:Switzerland
Idioma:eng
Resumo:Skimmianine is a furoquinoline alkaloid present mainly in the Rutaceae family. It has been reported to have analgesic, antispastic, sedative, anti-inflammatory, and other pharmacologic activities. Despite its critical pharmacological function, its metabolite profiling is still unclear. In this study, the in vivo metabolite profiling of skimmianine in rats was investigated using ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS). The metabolites were predicted using MetabolitePilot software. These predicted metabolites were further analyzed by MS² spectra, and compared with the detailed fragmentation pathway of the skimmianine standard and literature data. A total of 16 metabolites were identified for the first time in rat plasma, urine, and feces samples after oral administration of skimmianine. Skimmianine underwent extensive Phase I and Phase II metabolism in rats. The Phase I biotransformations of skimmianine consist of epoxidation of olefin on its furan ring (M1) followed by the hydrolysis of the epoxide ring (M4), hydroxylation (M2, M3), -demethylation (M5-M7), didemethylation (M14-M16). The Phase II biotransformations include glucuronide conjugation (M8-M10) and sulfate conjugation (M11-M13). The epoxidation of 2,3-olefinic bond followed by the hydrolysis of the epoxide ring and -demethylation were the major metabolic pathways of skimmianine. The results provide key information for understanding the biotransformation processes of skimmianine and the related furoquinoline alkaloids.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Quinolines); 4E1KLC380B (skimmianine)


  9 / 648 MEDLINE  
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PMID:28276762
Autor:He W; Jiang Y; Zhao MB; Zeng KW; Tu PF
Endereço:a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences , Peking University Health Science Center , Beijing 100191 , China.
Título:Ruticarpsides A-C, three new ester glycosides from the fruits of Tetradium ruticarpum.
Fonte:J Asian Nat Prod Res; 19(7):659-665, 2017 Jul.
ISSN:1477-2213
País de publicação:England
Idioma:eng
Resumo:In the course of our ongoing phytochemical investigation on the n-butanol extract of the fruits of Tetradium ruticarpum (Rutaceae), three new compounds, ruticarpsides A-C (1-3), were obtained and their structures were elucidated by a comprehensive analysis of NMR and MS data. Compound 3 showed a weak inhibition effect on nitric oxide production in BV-2 microglial cells stimulated with lipopolysaccharide.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (Glycosides); 0 (Lipopolysaccharides); 0 (ruticarpside C); 31C4KY9ESH (Nitric Oxide)


  10 / 648 MEDLINE  
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PMID:28273098
Autor:Morton CM
Endereço:Pittsburgh Parks Conservancy, Pittsburgh, PA.
Título:Phylogenetic relationships of Vepris (Rutaceae) inferred from chloroplast, nuclear, and morphological data.
Fonte:PLoS One; 12(3):e0172708, 2017.
ISSN:1932-6203
País de publicação:United States
Idioma:eng
Resumo:The tribe Toddalieae Hook. F. (Rutaceae) has been controversial since its inception by Bentham and Hooker. The nine taxa examined, Acronychia J.R. & G.Foster, Diphasia Pierre, Diphasiopsis Mendonca, Fagaropsis Mildbr.ex. Siebenl., Oricia Pierre, Teclea Delile, Toddaliopsis Engl., Toddalia Juss. and Vepris Comm. ex. A. Juss, have been recognized under the tribe Toddalieae or Tribes Acronychia, Phellodendron and Toddalia. More recently Araliopsis Engl., Diphasia, Diphasiopsis, Oricia, Teclea, and Toddaliopsis have been incorporated into the genus Vepris, while Toddalia and Fagaropsis have continued to be recognized as closely related. For this study, sequence data of one non-coding chloroplast region (trnL-F) and one nuclear region (ITS) and various morphological characters, based on Mziray's taxonomic studies were examined to try to elucidate these relationships. This study found that the taxa Diphasia, Diphasiopsis, Oricia, Teclea, Toddaliopsis, Vepris, Toddalia eugeniifolia Engl. and Toddalia glomerata F. Hoffm. form a monophyletic group. Due to the amount of intrageneric and intraspecific variation, species delimitations were difficult to determine; however, these genera should be united into Vepris. The analyses also confirmed that Toddalia asiatica (L.) Lam., Zanthoxylon sp. and Fagaropsis angolensis (Engl.) H.M. Gardner are the closest relatives to this group.
Tipo de publicação: JOURNAL ARTICLE
Nome de substância:0 (DNA, Intergenic); 0 (DNA, Plant)



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