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54 results on '"Nemorosone"'

51. Bridgehead enolate or bridgehead organolithium? DFT calculations provide insights into a difficult bridgehead substitution reaction in the synthesis of the polycyclic polyprenylated acylphloroglucinol (PPAP) nemorosone

Author

Christopher J. Hayes and Nigel S. Simpkins

Subjects
Bridged-Ring Compounds, Models, Molecular, chemistry.chemical_classification, Substitution reaction, Ketone, Stereochemistry, Acylation, Organic Chemistry, Lithium, Phloroglucinol, Biochemistry, Benzophenones, chemistry, Reactivity (chemistry), Physical and Theoretical Chemistry, Nemorosone
Abstract

A computational study (B3LYP), of the metallation of a bridged ketone, an important step in the synthesis of a polycyclic polyprenylated acylphloroglucinol (PPAP), nemorosone, shows three energetically distinct structural possibilities for the lithiated intermediate. These findings, along with observations of the reactivity of the intermediates in bridgehead substitutions, suggest that different intermediates may be formed depending upon the type of process used for lithiation.

Published
2013
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53. Effects of nemorosone, isolated from the plant Clusia rosea, on the cell cycle and gene expression in MCF-7 BUS breast cancer cell lines.

Author

Camargo MS, Oliveira MT, Santoni MM, Resende FA, Oliveira-Höhne AP, Espanha LG, Nogueira CH, Cuesta-Rubio O, Vilegas W, and Varanda EA

Subjects
Female, Flowers chemistry, Gene Expression Regulation, Neoplastic drug effects, Humans, MCF-7 Cells drug effects, Antineoplastic Agents, Phytogenic pharmacology, Benzophenones pharmacology, Breast Neoplasms pathology, Cell Cycle drug effects, Clusia chemistry
Abstract

Background: Breast cancer is the cause of considerable morbidity and mortality in women. While estrogen receptor antagonists have been widely used in breast cancer treatment, patients have increasingly shown resistance to these agents and the identification of novel targeted therapies is therefore required. Nemorosone is the major constituent of the floral resin from Clusia rosea and belongs to the class of polycyclic polyisoprenylated benzophenones of the acylphloroglucinol group. The cytotoxicity of nemorosone in human cancer cell lines has been reported in recent years and has been related to estrogen receptors in breast cancer cells., Methods: Changes induced by nemorosone in the cell cycle and gene expression of the MCF-7 BUS (estrogen-dependent) breast cancer cell line were analyzed using flow cytometry and the RT(2) Profiler PCR array, respectively., Results: In comparison to breast cancer cells without treatment, nemorosone induced discrete cell cycle arrest in the G1 phase and significant depletion in the G2 phase. Moreover, the compound altered the expression of 19 genes related to different pathways, especially the cell cycle, apoptosis and hormone receptors., Conclusion: These promising results justify further studies to clarify mechanisms of action of nemorosone, in view of evaluate the possible use of this benzophenone as adjuvant in the treatment of breast cancer., (Copyright © 2014 Elsevier GmbH. All rights reserved.)

Published
2015
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54. Evaluation of estrogenic, antiestrogenic and genotoxic activity of nemorosone, the major compound found in brown Cuban propolis

Author

Flávia Aparecida Resende, Mariana Santoro de Camargo, Aline M. Prieto, Wagner Vilegas, José-Manuel Molina-Molina, Mariana F. Fernández, Osmany Cuesta-Rubio, Paula Karina Boldrin, Eliana Aparecida Varanda, Cássia Regina Primila Cardoso, Nicolás Olea, Universidade Estadual Paulista (Unesp), University of Granada, and Universidad de La Habana

Subjects
Drug Evaluation, Preclinical, Estrogen receptor, Pharmacology, medicine.disease_cause, Mass Spectrometry, chemistry.chemical_compound, estrogen, antineoplastic agent, Estrogen Antagonists, Cuba, General Medicine, unclassified drug, Comet Assay, Research Article, estrogen receptor, in vitro study, Estrogenicity, Biology, Propolis, Benzophenones, Breast cancer, Clusia rosea, breast cancer, comet assay, estradiol, Cell Line, Tumor, medicine, Humans, controlled study, drug screening, human, Cell Proliferation, Plant Extracts, human cell, genotoxicity, Cancer, Estrogens, nemorosone, medicine.disease, Antiestrogen, Comet assay, chemistry, Complementary and alternative medicine, breast cell, antiestrogen, Nemorosone, DNA damage, Phytoestrogens, Genotoxicity, hormone receptor interaction, DNA Damage, benzophenone, Mutagens
Abstract

Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-27T11:30:04Z No. of bitstreams: 0Bitstream added on 2014-05-27T14:32:48Z : No. of bitstreams: 1 2-s2.0-84880934126.pdf: 413883 bytes, checksum: ddc1db78ebb0aa9c3cb6b68e2eae5349 (MD5) Made available in DSpace on 2014-05-27T11:30:04Z (GMT). No. of bitstreams: 0 Previous issue date: 2013-07-31 Background: Brown propolis is the major type of propolis found in Cuba; its principal component is nemorosone, the major constituent of Clusia rosea floral resins. Nemorosone has received increasing attention due to its strong in vitro anti-cancer action. The citotoxicity of nemorosone in several human cancer cell lines has been reported and correlated to the direct action it has on the estrogen receptor (ER). Breast cancer can be treated with agents that target estrogen-mediated signaling, such as antiestrogens. Phytoestrogen can mimic or modulate the actions of endogenous estrogens and the treatment of breast cancer with phytoestrogens may be a valid strategy, since they have shown anti-cancer activity.Methods: The aim of the present investigation was to assess the capacity of nemorosone to interact with ERs, by Recombinant Yeast Assay (RYA) and E-screen assays, and to determine by comet assay, if the compound causes DNA-damaging in tumoral and non-tumoral breast cells.Results: Nemorosone did not present estrogenic activity, however, it inhibited the 17-β-estradiol (E2) action when either of both methods was used, showing their antiestrogenicity. The DNA damage induced by the benzophenone in cancer and normal breast cells presented negative results.Conclusion: These findings suggest that nemorosone may have therapeutic application in the treatment of breast cancer. © 2013 Camargo et al.; licensee BioMed Central Ltd. UNESP- Univ. Estadual Paulista Faculty of Pharmaceutical Sciencies of Araraquara Department of Biological Sciences, Rodovia Araraquara-Jaú, Km 1, 14801-902 Araraquara, São Paulo School of Pharmacy University of Granada, Granada UNESP- Univ. Estadual Paulista Unidade São Vicente, Campus do Litoral Paulista, CEP 11330-900 São Vicente, São Paulo Instituto de Farmacia y Alimentos (IFAL) Universidad de La Habana, La Habana UNESP- Univ. Estadual Paulista Faculty of Pharmaceutical Sciencies of Araraquara Department of Biological Sciences, Rodovia Araraquara-Jaú, Km 1, 14801-902 Araraquara, São Paulo UNESP- Univ. Estadual Paulista Unidade São Vicente, Campus do Litoral Paulista, CEP 11330-900 São Vicente, São Paulo

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