Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Abstract

The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol–ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were confirmed by spectral data. The anti-oxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines.

Antioxidant, antimicrobial and antiproliferative activities of fungal metabolite produced by Aspergillus flavus on in vitro study

“…In this regarding, presence of ether and pyrazole compounds in A. flavus extract play major roles as antioxidant and antimicrobial activities; this concurs with that reported in the previous studies (Jelena & Maja, 2015;Srivastava et al, 2015;Narra et al, 2017;Yadav et al, 2018). (Narra et al (2017) Moreover, the present investigation confirmed the presence of other bioactive compounds as Spirosten, Naphthalene, Trinolabdan and hexadecene that characterized by their antiproliferative activity, similarly with that reported previously (Huang et al, 2003;Sisa et al, 2003;Popova et al, 2009;Lu et al, 2015;Lemoreaux, 2017;Zheng et al, 2018).…”

Variability in metabolites produced by Talaromyces pinophilus SPJ22 cultured on different substrates

“…Furthermore, undecanoic acid methyl ester, another important metabolite released by T . pinophilus SPJ22 has been found to possess antioxidant and antimicrobial properties [ 40 , 41 ].…”

Evaluation of chemical constituents and in vitro antimicrobial, antioxidant and cytotoxicity potential of rhizome of Astilbe rivularis (Bodho-okhati), an indigenous medicinal plant from Eastern Himalayan region of India

“…The compound also showed antidiabetic effect by enhancing glucose uptake via activation of Akt and Erk1/2 in C2C12 myotubes. Undecanoic methyl esters are reported to have cytotoxic effect against breast, ovarian, prostrate and liver cancer cell lines with IC 50 values in the range of 10–140 μM [30].…”