A utilização do safrol, principal componente químico do óleo de sassafráz, na síntese de substâncias bioativas na cascata do ácido araquidônico: antiinflamatórios, analgésicos e anti-trombóticos

Barreiro, Eliezer J.; Fraga, Carlos A.M.

doi:10.1590/s0100-40421999000500019

Cited by 47 publications

(26 citation statements)

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“…As in the previous oxidation, the primary alcohol 5 was obtained with a 59.4% and the secondary alcohol 6 with 1.1%w/w yield 11,[16][17][18] (scheme 1). In In the 1 H NMR spectrum of isomer 8, the presence of signal at d = 4.11 ppm (m, 1H') was to assigned at carbinolic hydrogen in C-2' position (secondary alcohol).…”

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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“…As an example, leaves of Sassafras albidum (Nutt.) Ness show analgesic, antiinflammatory, and anti-thrombotic potential and is source of safrole, a precursor of several bioactive compounds (Barreiro & Fraga, 1999). Other species, Ocotea indecora (Shott) Mez, showed sudorific, anti-rheumatic, and anti-syphilitic activities (Marques, 2001).…”

Section: Introductionmentioning

confidence: 99%

Chemical composition andin vitrocytotoxic effects of the essential oil fromNectandra leucanthaleaves

Grecco

Martins

Girola

et al. 2014

Pharmaceutical Biology

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Context: Nectandra (Lauraceae) species have been used in folk medicine as an antidiarrheal, analgesic, antifungal, etc., and have many pharmacological proprieties. Objective: Investigation of the chemical composition and cytotoxicity of essential oil from Nectandra leucantha Nees & Mart. leaves. This is the first study involving N. leucantha reported in the literature. Material and methods: The essential oil of N. leucantha leaves was obtained by hydrodistillation. Its chemical composition was determined using a combination of GC/FID, GC/MS, and determination of Kovats index (KI). In vitro cytotoxic activity was evaluated against six cancer cell lines -murine melanoma (B16F10-Nex2), human glioblastome (U-87), human cervical carcinoma (HeLa), human colon carcinoma (HCT), human breast adenocarcinoma (MCF7), and human cervical tumor (Siha) as well as against one non-tumorigenic cell line -human foreskin fibroblast (HFF). Results: Thirty-three compounds were identified primarily sesquiterpenes (81.41%), the main compounds being bicyclogermacrene (28.44%), germacrene A (7.34%), spathulenol (5.82%), and globulol (5.25%). Furthermore, monoterpenes were also found in the analyzed oil (12.84%), predominantly a-and b-pinenes (6.59 and 4.57%, respectively). The crude essential oil displayed significant cytotoxic activity against B16F10-Nex2 (IC 50 33 ± 1 lg/mL) and U87 (IC 50 75.95 ± 0.03 lg/mL) and HeLa (IC 50 60 ± 12 lg/mL) cell lines. The main identified compound, bicyclogermacrene, displayed IC 50 ranging from 3.1 ± 0.2 to 21 ± 6 lg/mL. Discussion and conclusion: The results indicate that the crude oils from leaves of N. leucantha displayed cytotoxic activity being bicyclogermacrene, the main compound identified in the crude oil responsible, at least in part, for this potential.

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A utilização do safrol, principal componente químico do óleo de sassafráz, na síntese de substâncias bioativas na cascata do ácido araquidônico: antiinflamatórios, analgésicos e anti-trombóticos

Cited by 47 publications

References 0 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

Chemical composition andin vitrocytotoxic effects of the essential oil fromNectandra leucanthaleaves

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