Safrol e eugenol: estudo da reatividade química e uso em síntese de produtos naturais biologicamente ativos e seus derivados

Costa, Paulo R. R.

doi:10.1590/s0100-40422000000300013

Cited by 42 publications

(31 citation statements)

References 14 publications

(19 reference statements)

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“…Cleavage of the methylenedioxy ring of nitrosafrol took place during the conversion into the catechol 4 (57.4% yield) using the AlCl 3 /CH 2 Cl 2 /H 2 O method [12][13][14][15] . In the 1 H NMR spectrum, the absence of the methylenedioxy singlet between 5.90-6.05 ppm confirmed the presence of catechol coupled with a broad signal at d=8.99 (brs, 2H).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Espinoza

Madrid

Liber

et al. 2010

J. Chil. Chem. Soc.

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Safrole from sassafras oil (Ocotea pretiosa Mez., Lauraceae), is an abundant natural product showing interesting functionality and chemical structure. Starting from safrole, nine derivatives were prepared and assessed for antiproliferative effect using different human cell lines. The in vitro growth inhibition assay was based on the sulphorhodamine dye to quantify cell viability. Some safrole derivatives, (2E)-3-(3',4'-methylenedioxi)phenyl acrylaldehyde (3) and 4-allyl-5-nitrobenzene-1,2-diol (4) presented better antiproliferative effect than the parent compound on two breast cancer cell lines (MCF-7 and MDA-MB-231) and one human colorectal cancer cell line (DLD-1) with IC 50 values of 55.0 + 7.11 µM, 37.5 + 2.65 µM and 44.0 + 6.92 µM, respectively, without toxicity towards dermal human fibroblast (DHF cells).

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Section: Resultsmentioning

confidence: 99%

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Espinoza

Madrid

Liber

et al. 2010

J. Chil. Chem. Soc.

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“…DC., popularly known as long pepper, is rich in safrole, a phenylpropanoid that is currently being used as a raw material for the manufacture of heliotropin, an important component of some perfumes, and piperonyl butoxide, a pesticide synergist for natural insecticides (Fazolin et al, 2007). Studies by Barreiro and Fraga (1999) and Costa (2000) on the chemical reactivity of safrole (2) and the acquisition of synthetic analogues have indicated great synthetic variability and excellent opportunities for their derivation.…”

Section: Research Articlementioning

confidence: 99%

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Parise-Filho

Pastrello

Camerlingo

et al. 2011

Pharmaceutical Biology

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“…Além de ser utilizado na aromatização de alimentos e perfumaria, pode ser usada como uma importante fonte de eugenol, substância utilizada para produzir a vanilina. Além da vanilina, o eugenol pode ser usado como precursor para a preparação de naftoquinonas, antraquinonas, dentre outras (Costa, 2000). O óleo essencial da P. dioica, também exibe várias atividades biológicas.…”

Section: Introductionunclassified

Constituintes químicos voláteis de especiarias ricas em eugenol

Oliveira¹,

Reis²,

Sacramento³

et al. 2009

Rev. bras. farmacogn.

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RESUMO: Utilizando a técnica de hidrodestilação, usando um adaptador Clevenger, foram extraídos óleos essenciais das espécies Pimenta dioica (folhas e frutos) e Syzygium aromaticum (botões florais, talos e folhas). A composição química dos óleos foi determinada através da analise CG-EM. Os teores de óleos essenciais variaram de 0,97 a 1,41% e 2,30 a 15,40% nas espécies Pimenta dioica e Syzygium aromaticum, respectivamente. O componente majoritário presente nessas espécies foi o eugenol, variando de 72,87 a 90,41%. Syzygium aromaticum forneceu maior teor de óleo essencial rico em eugenol. Em quantidades menores foram também encontrados chavicol e β-cariofileno.Unitermos: Syzygium aromaticum, Pimenta dioica, Myrtaceae, eugenol, Brasil, óleo essencial.ABSTRACT: "Volatile chemical constituents of rich spices in eugenol". Essential oils were extracted from the leaves and fruits of Pimenta dioica and leaves, stalks and floral buttons from Syziguim aromaticum by hydrodistillation using a Clevenger apparatus. The essential oil compositions were determined by CG-MS analyses. The yield varied from 0.97 to 1.41% and from 2.30 to 15.40% in the P. dioica and S. aromaticum, respectively. In both species the major component was the eugenol, varied from 72.87 to 90.41%, being richer the essential oil extracted from S. aromaticum. Chavicol and β-caryophyllene were identified in low percentage.

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Safrol e eugenol: estudo da reatividade química e uso em síntese de produtos naturais biologicamente ativos e seus derivados

Cited by 42 publications

References 14 publications

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Constituintes químicos voláteis de especiarias ricas em eugenol

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