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[PMID]: 29229205 [Au] Autor: Li SG; Wang KB; Gong C; Bao Y; Qin NB; Li DH; Li ZL; Bai J; Hua HM [Ad] Endereço: Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China. [Ti] Título: Cytotoxic quinazoline alkaloids from the seeds of Peganum harmala. [So] Source: Bioorg Med Chem Lett;28(2):103-106, 2018 01 15. [Is] ISSN: 1464-3405 [Cp] País de publicação: England [La] Idioma: eng [Ab] Resumo: Seventeen quinazoline alkaloids and derivatives, containing two pairs of new epimers, named as (S)- and (R)-1-(2-aminobenzyl)-3-hydroxypyrrolidin-2-one ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside (1, 2), (S)- and (R)-vasicinone ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside (3, 4), and a new enantiomer (12b), together with six known ones (5-8, 10, and 12a), and three pairs of known enantiomers (9, 11, and 13), were isolated from the ethanol extracts of the seeds of Peganum harmala L.. Their structures including the absolute configuration were elucidated by using 1D and 2D NMR, and ECD calculation approaches. The cytotoxic activities of all isolated compounds were evaluated. 11 showed moderate cytotoxicity against PC-3 cells with an IC value of 15.41 µM. [Mh] Termos MeSH primário: Alcaloides/farmacologia Antineoplásicos Fitogênicos/farmacologia Peganum/química Quinazolinas/farmacologia Sementes/química [Mh] Termos MeSH secundário: Alcaloides/química Alcaloides/isolamento & purificação Antineoplásicos Fitogênicos/química Antineoplásicos Fitogênicos/isolamento & purificação Linhagem Celular Tumoral Proliferação Celular/efeitos dos fármacos Relação Dose-Resposta a Droga Ensaios de Seleção de Medicamentos Antitumorais Seres Humanos Estrutura Molecular Quinazolinas/química Quinazolinas/isolamento & purificação Relação Estrutura-Atividade [Pt] Tipo de publicação: JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T [Nm] Nome de substância: 0 (Alkaloids); 0 (Antineoplastic Agents, Phytogenic); 0 (Quinazolines) [Em] Mês de entrada: 1802 [Cu] Atualização por classe: 180216 [Lr] Data última revisão: 180216 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 171213 [St] Status: MEDLINE

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[PMID]: 28279698 [Au] Autor: Herraiz T; Guillén H; Arán VJ; Salgado A [Ad] Endereço: Instituto de Ciencia y Tecnología de Alimentos y Nutrición (ICTAN-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain. Electronic address: therraiz@ictan.csic.es. [Ti] Título: Identification, occurrence and activity of quinazoline alkaloids in Peganum harmala. [So] Source: Food Chem Toxicol;103:261-269, 2017 May. [Is] ISSN: 1873-6351 [Cp] País de publicação: England [La] Idioma: eng [Ab] Resumo: Peganum harmala L. is a medicinal plant from the Mediterranean region and Asia currently used for recreative psychoactive purposes (Ayahuasca analogue), and increasingly involved in toxic cases. Its psychopharmacological and toxicological properties are attributed to quinazoline and ß-carboline alkaloids. In this work three major quinazoline alkaloids were isolated from P. harmala extracts and characterized as peganine (vasicine), deoxypeganine (deoxyvasicine) and a novel compound identified by HPLC-DAD-MS and NMR as peganine ß-d-glucopyranosyl-(1 â†’ 6)-ß-d-glucopyranoside (peganine glycoside). Peganine appeared in flowers and leaves in high levels; high amounts of deoxypeganine and peganine were found in immature and green fruits whereas peganine and peganine glycoside accumulated in high amount in dry seeds reaching up to 1 and 3.9% (w/w), respectively. Roots and stems contained low amount of quinazolines. Seeds extracts containing both quinazoline and ß-carboline alkaloids potently inhibited human monoamine oxidase (MAO)-A. However, quinazoline alkaloids did not contribute to MAO inhibition that was due to ß-carbolines, suggesting that MAO-related psychoactive or toxic actions do not arise from quinazolines. Quinazoline alkaloids were poor radical scavengers in the ABTS assay whereas seed extracts had good activity. Quinazoline alkaloids are known to exert bronchodilator and abortifacient actions, and could contribute to such effects reported in P. harmala. [Mh] Termos MeSH primário: Alcaloides/química Alcaloides/farmacologia Peganum/química Quinazolinas/química Quinazolinas/farmacologia [Mh] Termos MeSH secundário: Alcaloides/análise Antioxidantes/química Antioxidantes/farmacologia Cromatografia Líquida de Alta Pressão Dissacarídeos/análise Dissacarídeos/farmacologia Avaliação Pré-Clínica de Medicamentos/métodos Espectroscopia de Ressonância Magnética Estrutura Molecular Inibidores da Monoaminoxidase/química Inibidores da Monoaminoxidase/farmacologia Plantas Medicinais/química Quinazolinas/análise Espectrometria de Massas por Ionização por Electrospray [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Alkaloids); 0 (Antioxidants); 0 (Disaccharides); 0 (Monoamine Oxidase Inhibitors); 0 (Quinazolines); 495-59-0 (3-deoxyvasicine); 6C2ZBI733P (vasicine) [Em] Mês de entrada: 1707 [Cu] Atualização por classe: 170726 [Lr] Data última revisão: 170726 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 170311 [St] Status: MEDLINE

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[PMID]: 28128938 [Au] Autor: Wang KB; Li DH; Bao Y; Cao F; Wang WJ; Lin C; Bin W; Bai J; Pei YH; Jing YK; Yang D; Li ZL; Hua HM [Ad] Endereço: Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University , West Lafayette, Indiana 47907, United States. [Ti] Título: Structurally Diverse Alkaloids from the Seeds of Peganum harmala. [So] Source: J Nat Prod;80(2):551-559, 2017 Feb 24. [Is] ISSN: 1520-6025 [Cp] País de publicação: United States [La] Idioma: eng [Ab] Resumo: Investigation of the alkaloids from Peganum harmala seeds yielded two pairs of unique racemic pyrroloindole alkaloids, (±)-peganines A-B (1-2); two rare thiazole derivatives, peganumals A-B (3-4); six new ß-carboline alkaloids, pegaharmines F-K (5-10); and 12 known analogues. Their structures, including stereochemistry, were elucidated through spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray diffraction. Notably, the incorporation of pyrrole and indole moieties in peganines A-B, thiazole fragments in peganumals A-B, and a C-1 α,ß-unsaturated ester motif in pegaharmine F (5) are all rare, and their presence in the genus Peganum were demonstrated for the first time. All isolates were tested for antiproliferative activities against the HL-60, PC-3, and SGC-7901 cancer cell lines, and compounds 9, 11, 12, and 13 exhibited moderate cytotoxicity against HL-60 cancer cell lines with IC values in the range of 4.36-9.25 µM. [Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/química Antineoplásicos Fitogênicos/isolamento & purificação Medicamentos de Ervas Chinesas/química Medicamentos de Ervas Chinesas/isolamento & purificação Alcaloides de Indol/química Alcaloides de Indol/isolamento & purificação Peganum/química Sementes/química [Mh] Termos MeSH secundário: Antineoplásicos Fitogênicos/farmacologia Carbolinas/química Ensaios de Seleção de Medicamentos Antitumorais Medicamentos de Ervas Chinesas/farmacologia Células HL-60 Seres Humanos Alcaloides de Indol/farmacologia Concentração Inibidora 50 Estrutura Molecular Ressonância Magnética Nuclear Biomolecular [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Antineoplastic Agents, Phytogenic); 0 (Carbolines); 0 (Drugs, Chinese Herbal); 0 (Indole Alkaloids) [Em] Mês de entrada: 1707 [Cu] Atualização por classe: 170721 [Lr] Data última revisão: 170721 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 170128 [St] Status: MEDLINE [do] DOI: 10.1021/acs.jnatprod.6b01146

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[PMID]: 27377797 [Au] Autor: Tascón M; Benavente F; Vizioli NM; Gagliardi LG [Ad] Endereço: Laboratorio de Investigación y Desarrollo de Métodos Analíticos, LIDMA and División Química Analítica, Facultad de Ciencias Exactas, UNLP-CONICET, La PlataLaboratorio de Investigación y Desarrollo de Métodos Analíticos, LIDMA and División Química Analítica, Facultad de Ciencias Exactas, UNLP-CONICET [Ti] Título: A rapid and simple method for the determination of psychoactive alkaloids by CE-UV: application to Peganum Harmala seed infusions. [So] Source: Drug Test Anal;9(4):596-602, 2017 Apr. [Is] ISSN: 1942-7611 [Cp] País de publicação: England [La] Idioma: eng [Ab] Resumo: The ß-carboline alkaloids of the harmala (HAlks) group are compounds widely spread in many natural sources, but found at relatively high levels in some specific plants like Peganum harmala (Syrian rue) or Banisteriopsis caapi. HAlks are a reversible Mono Amino Oxidase type A Inhibitor (MAOI) and, as a consequence, these plants or their extracts can be used to produce psychotropic effects when are combined with psychotropic drugs based on amino groups. Since the occurrence and the levels of the HAlks in natural sources are subject to significant variability, more widespread use is not clinical but recreational or ritual, for example B. caapi is a known part of the Ayahuasca ritual mixture. The lack of simple methods to control the variable levels of these compounds in natural sources restricts the possibilities to dose in strict quantities and, as a consequence, limits its use with pharmacological or clinical purposes. In this work, we present a fast, simple, and robust method of quantifying simultaneously the six HAlks more frequently found in plants, i.e., harmine, harmaline, harmol, harmalol, harmane, and norharmane, by capillary electrophoresis instruments equipped with the more common detector UV. The method is applied to analyze these HAlks in P. Harmala seeds infusion which is a frequent intake form for these HAlks. The method is validated in three different instruments in order to evaluate the transferability and to compare the performances between them. In this case, harmaline, harmine, and harmol were found in the infusion samples. Copyright © 2016 John Wiley & Sons, Ltd. [Mh] Termos MeSH primário: Eletroforese Capilar/métodos Harmalina/análise Harmina/análogos & derivados Harmina/análise Inibidores da Monoaminoxidase/análise Peganum/química Sementes/química [Mh] Termos MeSH secundário: Alcaloides/análise Carbolinas/análise Eletroforese Capilar/economia Harmalina/análogos & derivados Limite de Detecção Extratos Vegetais/química Psicotrópicos Fatores de Tempo [Pt] Tipo de publicação: EVALUATION STUDIES; JOURNAL ARTICLE [Nm] Nome de substância: 0 (Alkaloids); 0 (Carbolines); 0 (Monoamine Oxidase Inhibitors); 0 (Plant Extracts); 0 (Psychotropic Drugs); 2NQN80556Q (harmalol); 487-03-6 (harmol); 4FHH5G48T7 (Harmine); 94HMA1I78O (norharman); CN58I4TOET (Harmaline) [Em] Mês de entrada: 1707 [Cu] Atualização por classe: 170718 [Lr] Data última revisão: 170718 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 160706 [St] Status: MEDLINE [do] DOI: 10.1002/dta.1989

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[PMID]: 28476704 [Au] Autor: Ghaffar S; Afridi SK; Aftab MF; Murtaza M; Syed SA; Begum S; Waraich RS [Ad] Endereço: Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan. [Ti] Título: Attenuation of palmitate induced insulin resistance in muscle cells by harmala, clove and river red gum. [So] Source: Pak J Pharm Sci;29(5 Suppl):1795-1800, 2016 Sep. [Is] ISSN: 1011-601X [Cp] País de publicação: Pakistan [La] Idioma: eng [Ab] Resumo: The present study aimed to decipher the mechanism of action of selected anti-diabetic plants extracts on palmitic acid mediated insulin resistance in muscle cells. Our results showed that extract from Peganum harmala seeds, Eucalyptus camaldulensis and Syzygium aromaticum leaves, showed significant antioxidant activity. We found that these extracts were able to affect stress signalling by reducing p-38 MAP kinase phosphorylation. They also reduced phosphorylation of substrate for insulin receptor (IRS) at serine residues and increased its phosphorylation at tyrosine residues and also enhanced PKB phosphorylation. Glucose uptake was also enhanced in muscle cells after treatment with these extracts. Extracts from Lantana camara, Psidium gujava fruit and different parts of Cassia alata did not affect FFA mediated down-regulation of insulin signalling. The study conclude that seeds of Peganum harmala and leaves of Eucalyptus camaldulensis and Syzygium aromaticum enhanced insulin signal transduction and glucose uptake in muscle cells via reducing oxidative stress. As a result, these herbal extracts may be considered useful to protect from insulin resistance. [Mh] Termos MeSH primário: Hipoglicemiantes/administração & dosagem Resistência à Insulina Ácido Palmítico/administração & dosagem Peganum/química Extratos Vegetais/administração & dosagem Syzygium/química [Mh] Termos MeSH secundário: Animais Linhagem Celular Glucose/metabolismo Insulina/metabolismo Proteínas Substratos do Receptor de Insulina/química Proteínas Substratos do Receptor de Insulina/metabolismo Camundongos Fosforilação Espécies Reativas de Oxigênio/metabolismo Transdução de Sinais [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Hypoglycemic Agents); 0 (Insulin); 0 (Insulin Receptor Substrate Proteins); 0 (Plant Extracts); 0 (Reactive Oxygen Species); 2V16EO95H1 (Palmitic Acid); IY9XDZ35W2 (Glucose) [Em] Mês de entrada: 1706 [Cu] Atualização por classe: 170626 [Lr] Data última revisão: 170626 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 170507 [St] Status: MEDLINE

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[PMID]: 28375115 [Au] Autor: Shohaib HM; Nawaz S; Matin A [Ad] Endereço: Department of Medical Lab Technology, University of Haripur, Hattar Road, Haripur, Khyber Pakhtunkhwa, Pakistan. [Ti] Título: Methanolic extract of Peganum harmala exhibit potent activity against Acanthamoeba castellanii cysts and its encystment in vitro. [So] Source: Pak J Pharm Sci;29(6):1993-1996, 2016 Nov. [Is] ISSN: 1011-601X [Cp] País de publicação: Pakistan [La] Idioma: eng [Ab] Resumo: Acanthamoeba castellanii is member of free living amoeba that may cause painful sight-threatening keratitis and life threatening encephalitis which involves central nervous system. Treatments for both infections are problematic because of the amoebic cysts resistance to therapeutic agents. Here we evaluated in vitro strength of methanolic seed extract of Peganum harmala on Acanthamoeba cysts and its encystment mechanism. Our results revealed seed extracts (1 to 30mg/ml) exhibited amoebicidal effects against Acanthamoeba cysts. Furthermore Acanthamoeba encystment was also inhibited in concentration dependent manner with maximum inhibition at 2µg/ml after 48h incubation. In conclusion, we demonstrated for the first time that methanolic extracts exhibit remarkable inhibition of Acanthamoeba cysts and encystment in vitro which could serve a potential new natural agent against Acanthamoeba. [Mh] Termos MeSH primário: Acanthamoeba castellanii/efeitos dos fármacos Amebíase/tratamento farmacológico Amebicidas/farmacologia Metanol/química Peganum/química Extratos Vegetais/farmacologia Solventes/química [Mh] Termos MeSH secundário: Acanthamoeba castellanii/crescimento & desenvolvimento Amebíase/parasitologia Amebicidas/química Amebicidas/isolamento & purificação Relação Dose-Resposta a Droga Fitoterapia Extratos Vegetais/química Extratos Vegetais/isolamento & purificação Plantas Medicinais Sementes/química Fatores de Tempo [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Amebicides); 0 (Plant Extracts); 0 (Solvents); Y4S76JWI15 (Methanol) [Em] Mês de entrada: 1711 [Cu] Atualização por classe: 171103 [Lr] Data última revisão: 171103 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 170405 [St] Status: MEDLINE

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[PMID]: 27649128 [Au] Autor: Apostolico I; Aliberti L; Caputo L; De Feo V; Fratianni F; Nazzaro F; Souza LF; Khadhr M [Ad] Endereço: Department of Pharmacy, University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano (Salerno), Italy. i.apostolico1@studenti.unisa.it. [Ti] Título: Chemical Composition, Antibacterial and Phytotoxic Activities of Peganum harmala Seed Essential Oils from Five Different Localities in Northern Africa. [So] Source: Molecules;21(9), 2016 Sep 15. [Is] ISSN: 1420-3049 [Cp] País de publicação: Switzerland [La] Idioma: eng [Ab] Resumo: Peganum harmala L., also known as Syrian rue or Pègano, is a herbaceous plant belonging to the Zygohpyllaceae family, and is widely used in traditional medicine. The chemical composition of essential oils of P. harmala seeds from five different regions of Northern Africa (Algeria, Egypt, Libya, Morocco and Tunisia) was studied by GC and GC-MS analyses. A total of 105 compounds were identified, the main components being oxygenated monoterpenes and oxygenated sesquiterpenes. Eugenol is the main component in all oils. The antimicrobial activity of the essential oils was assayed against some bacterial strains: Staphylococcus aureus (DSM 25693), Bacillus cereus (DSM 4313), Bacillus cereus (DSM4384), Escherichia coli (DMS 857) and Pseudomonas aeruginosa (ATCC 50071). All the oils showed different inhibitory activity. In the twentieth century this is an important result; we need possible new botanical drugs because the problem of resistance to antimicrobial drugs has become apparent. Moreover, the essential oils were evaluated for their possible in vitro phytotoxic activity against germination and initial radicle growth of Raphanus sativus L., Lepidium sativum L., and Ruta graveolens L. The results showed that both germination and radical elongation were sensitive to the oils. [Mh] Termos MeSH primário: Antibacterianos Bactérias/crescimento & desenvolvimento Herbicidas Lepidium sativum/crescimento & desenvolvimento Óleos Voláteis Peganum/química Raphanus/crescimento & desenvolvimento Ruta/crescimento & desenvolvimento Sementes/química [Mh] Termos MeSH secundário: África do Norte Antibacterianos/química Antibacterianos/isolamento & purificação Antibacterianos/farmacologia Herbicidas/química Herbicidas/isolamento & purificação Herbicidas/farmacologia Óleos Voláteis/química Óleos Voláteis/isolamento & purificação Óleos Voláteis/farmacologia [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Anti-Bacterial Agents); 0 (Herbicides); 0 (Oils, Volatile) [Em] Mês de entrada: 1704 [Cu] Atualização por classe: 170417 [Lr] Data última revisão: 170417 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 160921 [St] Status: MEDLINE

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[PMID]: 27452655 [Au] Autor: Shang X; Guo X; Li B; Pan H; Zhang J; Zhang Y; Miao X [Ad] Endereço: Key Laboratory of New Animal Drug Project, Gansu Province, Key Laboratory of Veterinary Pharmaceutical Development of Ministry of Agriculture, Lanzhou Institute of Husbandry and Pharmaceutical Sciences of Chinese Academy of Agricultural Science, Lanzhou 730050, PR China. Electronic address: shangxf9 [Ti] Título: Microwave-assisted extraction of three bioactive alkaloids from Peganum harmala L. and their acaricidal activity against Psoroptes cuniculi in vitro. [So] Source: J Ethnopharmacol;192:350-361, 2016 Nov 04. [Is] ISSN: 1872-7573 [Cp] País de publicação: Ireland [La] Idioma: eng [Ab] Resumo: ETHNOPHARMACOLOGICAL RELEVANCE: Peganum harmala L. is a perennial herbaceous, glabrous plant that grows in semi-arid conditions, steppe areas and sandy soils. It is used to treat fever, diarrhoea, subcutaneous tumours, arthralgia, rheumatism, cough, amnesia and parasitic diseases in folk medicines. In this paper, we aimed to develop a simpler and faster method for the extraction of three alkaloids from Peganum harmala L. than other conventional methods by optimizing the parameters of a microwave-assisted extraction (MAE) method, and to investigate the acaricidal activities of three compounds against Psoroptes cuniculi. MATERIALS AND METHODS: After optimizing the operating parameters with the single factor experiment and a Box-Behnken design combined with a response-surface methodology, a MAE method was developed for extracting the alkaloids from the seeds, and a high-performance liquid chromatography was used to quantify these compounds. An in vitro experiments were used to study the acaricidal activities. RESULTS: The optimal conditions of MAE method were as follows: liquid-to-solid ratio 31.3:1mL/g, ethanol concentration 75.5%, extraction time 10.1min, temperature 80.7°C, and microwave power 600W. Compared to the heat reflux extraction (HRE, 60min) and the ultrasonic-assisted extraction (UAE, 30min) methods, MAE method require the shortest time (10min) and obtain the highest yield of three compounds (61.9mg/g). Meanwhile, the LT values for the vasicine (1.25 and 2.5mg/mL), harmaline (1.25 and 2.5mg/mL), harmine (1.25 and 2.5mg/mL) and MAE extract (100mg/mL) against Psoroptes cuniculi were 12.188h, 9.791h, 11.994h, 10.095h, 11.293h, 9.273h and 17.322h, respectively. CONCLUSIONS: The MAE method developed exhibited the highest extraction yield within the shortest time and thus could be used to extract the active compounds from Peganum harmala L. on an industrial basis. As the active compounds of Peganum harmala L., vasicine, harmalin and harmine presented the marked acaricidal activities against Psoroptes cuniculi, and could be widely applied for the treatments of acariasis in animals. [Mh] Termos MeSH primário: Acaricidas/farmacologia Alcaloides/farmacologia Fracionamento Químico/métodos Micro-Ondas Peganum/química Extratos Vegetais/farmacologia Psoroptidae/efeitos dos fármacos [Mh] Termos MeSH secundário: Acaricidas/isolamento & purificação Alcaloides/isolamento & purificação Animais Cromatografia Líquida de Alta Pressão Cromatografia de Fase Reversa Relação Dose-Resposta a Droga Harmalina/isolamento & purificação Harmalina/metabolismo Harmina/isolamento & purificação Harmina/farmacologia Temperatura Alta Testes de Sensibilidade Parasitária Fitoterapia Extratos Vegetais/isolamento & purificação Plantas Medicinais Quinazolinas/isolamento & purificação Quinazolinas/farmacologia Sementes/química Fatores de Tempo Ultrassom [Pt] Tipo de publicação: COMPARATIVE STUDY; JOURNAL ARTICLE; VALIDATION STUDIES [Nm] Nome de substância: 0 (Acaricides); 0 (Alkaloids); 0 (Plant Extracts); 0 (Quinazolines); 4FHH5G48T7 (Harmine); 6C2ZBI733P (vasicine); CN58I4TOET (Harmaline) [Em] Mês de entrada: 1705 [Cu] Atualização por classe: 170912 [Lr] Data última revisão: 170912 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 160726 [St] Status: MEDLINE

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[PMID]: 27273342 [Au] Autor: Wang C; Zhang Z; Wang Y; He X [Ad] Endereço: School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China. [Ti] Título: Cytotoxic Constituents and Mechanism from Peganum harmala. [So] Source: Chem Biodivers;13(7):961-8, 2016 Jul. [Is] ISSN: 1612-1880 [Cp] País de publicação: Switzerland [La] Idioma: eng [Ab] Resumo: Peganum harmala L. is a traditional Chinese and Uygur medicine used to treat cancer. Bioactivity-guided fractionation was applied to determine the cytotoxic constituents from P. harmala. A novel triterpenoid and a phenolic glycoside were isolated and identified, as well as seven known compounds. The novel metabolites were elucidated to be 3α-acetoxy-27-hydroxyolean-12-en-28-oic acid methyl ester (1, OA) and N-acetyl-9-syringinoside (9). Some compounds exhibited potent cytotoxicity against human tumor cells. Among them, OA showed the highest cytotoxicity against human lung cancer cells A549 with an IC50 value of 8.03 ± 0.81 µm. OA had a potent anti-NSCLC cell activity by interfering with the epidermal growth factor receptor (EGFR) activation and its downstream signaling, and could exert an antiproliferative effect by inactivation of EGFR-driven antiapoptotic pathway followed by the release of mitochondrial cytochrome c, which might prove to be a promising leading compound for the development of an anti-lung cancer drug. [Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/farmacologia Peganum/química Inibidores de Proteínas Quinases/farmacologia [Mh] Termos MeSH secundário: Antineoplásicos Fitogênicos/química Antineoplásicos Fitogênicos/isolamento & purificação Apoptose/efeitos dos fármacos Linhagem Celular Tumoral Proliferação Celular/efeitos dos fármacos Relação Dose-Resposta a Droga Ensaios de Seleção de Medicamentos Antitumorais Seres Humanos Conformação Molecular Inibidores de Proteínas Quinases/química Inibidores de Proteínas Quinases/isolamento & purificação Receptor do Fator de Crescimento Epidérmico/antagonistas & inibidores Receptor do Fator de Crescimento Epidérmico/metabolismo Relação Estrutura-Atividade [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Antineoplastic Agents, Phytogenic); 0 (Protein Kinase Inhibitors); EC 2.7.10.1 (Receptor, Epidermal Growth Factor) [Em] Mês de entrada: 1701 [Cu] Atualização por classe: 170117 [Lr] Data última revisão: 170117 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 160609 [St] Status: MEDLINE [do] DOI: 10.1002/cbdv.201500384

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[PMID]: 26362768 [Au] Autor: Filali I; Romdhane A; Znati M; Jannet HB; Bouajila J [Ti] Título: Synthesis of New Harmine Isoxazoles and Evaluation of their Potential Anti-Alzheimer, Anti-inflammatory, and Anticancer Activities. [So] Source: Med Chem;12(2):184-90, 2016. [Is] ISSN: 1875-6638 [Cp] País de publicação: Netherlands [La] Idioma: eng [Ab] Resumo: Harmine 1 was extracted from the seeds of Peganum harmala. From this natural molecule, a new series of isoxazole derivatives with complete regiospecificity were prepared using 1,3-dipolar cycloaddition reactions with various arylnitrile oxides. Harmine and its derivatives were characterized by (1)H NMR, (13)C NMR and HRMS. The evaluation of their anti-acetylcholinesterase (AChE), anti-5-lipoxygenase (5-LOX), anti-xanthine oxidase (XOD) and anticancer activities were studied in vitro against AChE, 5-LOX and XOD enzymes, respectively, and in HTC-116, MCF7 and OVCAR-3 cancer cell lines. The prepared derivatives were shown to be inactive against the XOD enzyme (0-38.3 ± 1.9% at 100 µM). Compound 2 exhibited the best anti-AChE activity (IC50=1.9 ± 1.5 µM). Derivatives 3a, 3b and 3d had moderate cytotoxic activities (IC50=5.0 ± 0.3 µM (3a) and IC50=6.3 ± 0.4 µM (3b) against HCT 116 cells, IC50=5.0 ± 1.0 µM (3d) against MCF7 cells). [Mh] Termos MeSH primário: Doença de Alzheimer/tratamento farmacológico Anti-Inflamatórios não Esteroides/farmacologia Antineoplásicos/farmacologia Harmina/análogos & derivados Harmina/farmacologia Isoxazóis/farmacologia [Mh] Termos MeSH secundário: Anti-Inflamatórios não Esteroides/síntese química Antineoplásicos/síntese química Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 Inibidores da Colinesterase/síntese química Inibidores da Colinesterase/farmacologia Reação de Cicloadição Células HCT116 Harmina/síntese química Seres Humanos Isoxazóis/síntese química Inibidores de Lipoxigenase/síntese química Inibidores de Lipoxigenase/farmacologia Células MCF-7 Peganum Espectroscopia de Prótons por Ressonância Magnética Relação Estrutura-Atividade Tamoxifeno/farmacologia Xantina Oxidase/antagonistas & inibidores [Pt] Tipo de publicação: JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T [Nm] Nome de substância: 0 (Anti-Inflammatory Agents, Non-Steroidal); 0 (Antineoplastic Agents); 0 (Cholinesterase Inhibitors); 0 (Isoxazoles); 0 (Lipoxygenase Inhibitors); 094ZI81Y45 (Tamoxifen); 4FHH5G48T7 (Harmine); EC 1.17.3.2 (Xanthine Oxidase) [Em] Mês de entrada: 1703 [Cu] Atualização por classe: 170302 [Lr] Data última revisão: 170302 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 150913 [St] Status: MEDLINE

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