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

Abstract

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).

Biological evaluation of Safrole oil and Safrole oil Nanoemulgel as antioxidant, antidiabetic, antibacterial, antifungal and anticancer

“…Some safrole derivatives demonstrated better antiproliferative effects than the parent compound on breast cancer cell lines (MCF-7) and a colorectal cancer cell line (DLD-1). These findings support the findings of the current study since safrole showed anticancer activity on different cancer cell lines [ 62 ]. In another study carried out by Song et al on safrole from Cinnamomum longepaniculatum leaf and its activity against cancer cell growth on human hepatoma cell line (BEL-7402).…”

Response of serum biochemical profile, antioxidant enzymes, and gut microbiota to dietary Hong-bailanshen supplementation in horses

“…CAT could decompose hydrogen peroxide in the body and block the formation of free radicals ( Shi et al, 2023 ). MDA is one of the products of lipid peroxidation, exhibits cytotoxicity and genotoxicity, is an essential indicator of oxidative stress status, and indicates various diseases in the body ( Catalan et al, 2010 ; Mohideen et al, 2023 ). These results of serum indicators suggested that HBLS could enhance the antioxidant ability of horses.…”

Chemical Analysis and In Vitro Bioactivity of Essential Oil of Laurelia sempervirens and Safrole Derivatives against Oomycete Fish Pathogens

“…Safrole derivatives can be synthesized by chemical modification, and some of these derivatives have been proved to have better antimicrobial activity; indeed, in the last decade, this research group reported some safrole derivatives obtained by traditional organic chemistry protocols with a series of modifications [24,25].…”

“…Standard pure compounds for co-injection in GC/MS, α-pinene, β-phellandrene, safrole, isosafrole, and piperonal were purchased from Sigma-Aldrich Co. (St. Louis, MO, USA). The separation and identification of the synthesized compounds was carried out by previously performed methods [24,25].…”

“…Safrole derivatives (Figure 2) obtained from the natural compound 1 were synthesized and characterized by standard methods [24,25], except for compound 9, 4-allylbenzene-1,2-diol.…”