Inhibition of squalene synthase of rat liver by abietane diterpenes derivatives

Abstract

In the current study, chemical composition of cultivated Salvia canariensis L was determined. In this work, carnosol was the main product isolated, and the concentration of rosmanol is also significant. We prepared more lipophilic derivatives from carnosol, and both isolated and semisynthetic abietane diterpenes were evaluated in vitro as inhibitors of squalene synthase isolated from rat liver.Among the compounds tested, carnosol was the most potent inhibitor with an IC 50 value of 17.6 μM. These results highlight the great potential of this species for the commercial production of extracts of interest for their possible uses as ingredients in nutritional supplements for the treatment of hyperlipidemia. 2 1. EXPERIMENTAL General experimental proceduresThe NMR spectra were recorded on BrukerAvance 300 MHz and Bruker Avance 400 MHz spectrometers in CDCl 3, unless otherwise noted. Chemical shifts are given in ppm with TMS as the internal standard. IR spectra were obtained on a Bruker IFS 28/55 (FTIR) spectrometer and UV spectra on a JASCO V-560. Low resolution mass spectra were run on a VG Micromass ZAB-2F and high-resolution mass spectra on a VG Micromass ZAB-2F at 70 eV. Merck silica gel 60 Å 0.063-0.200 mm (70-230 mesh) was used for column chromatography. Analytical thin-layer chromatography (TLC) and preparative TLC were carried out on precoated Schleicher and Schüll plates.

Environmental Influence of growth regulators and light condition on some callus traits of rosemary (Rosmarinus officinalis L. ) in vitro

“…The plant parts were sterilized before planting using ethyl alcohol at a concentration of 70% for 1 minute. Then the plant parts were sterilized with sodium hypochlorite following the experimental design with three concentrations (4,8,12) % and at intervals of 15-20 minutes, and the best result was using an 8% concentration for 15 minutes, which gave the lowest percentage of contamination. After the sterilization, the plant parts were washed by sterile distilled water 3 times for 5 minutes in in laminar flow.…”

“…Its medical importance is due to the fact that it contains essential oil, as the chemical composition of these secondary metabolites varies with different environmental conditions [11]. Recent studies have shown that plant extracts are an effective inhibitor of food pathogens [12]. Its biological properties are due to its high content of secondary metabolism such as carnosic acid, carnosol, rosmanol, rosmarinic acid [13].…”

Diterpenoids: Natural Distribution, Semisynthesis at Room Temperature and Pharmacological Aspects‐A Decade Update

“…The main diterpenoid carnosol ( 19 ) was obtained from the acetone extract of Salvia canariensis by Alonso and his group to follow the protocol designed by Marrero et al [25] The design and semisynthesis were started from natural diterpenoid ( 19 ) to enhance the lipophilicity of semisynthetic derivatives through the chemical transformations of the hydroxyl group of carnosol ( 19 ) in 2019 [26] . The parent compound ( 19 ) in CH 2 Cl 2 undergoes the acetylation reaction in the presence of the acetic anhydride (Ac 2 O), DMAP, and triethanolamine (TEA) to afford ester ( 20 ) at room temperature in 92.5 % yield.…”

In Vitro Culture of Rosmarinus officinalis L. in a Temporary Immersion System: Influence of Two Phytohormones on Plant Growth and Carnosol Production

“…Rosmarinus officinalis L. is a medicinal plant used since ancient times, whose biological properties are attributable to its high content in phytochemicals as carnosol, carnosic acid, rosmarinic acid, rosmanol or ursolic acid, among others [ 4 ]. Of particular interests are carnosic acid and its oxidized derivatives, exhibiting various interesting biological activities [ 5 , 6 ].…”