92834-90-7Relevant academic research and scientific papers
Novel caffeic acid amide antioxidants: Synthesis, radical scavenging activity and performance under storage and frying conditions
Aladedunye, Felix,Catel, Yohann,Przybylski, Roman
, p. 945 - 952 (2012)
Twelve novel dihydro-caffeic acid amides were synthesised in good yields and fully characterised by 1H NMR, 13C NMR, and MS. Their radical scavenging activities were assessed by DPPH assay. Additionally, their abilities to protect polyunsaturated oils under accelerated storage and frying conditions were evaluated. All the new compounds possessed significantly higher radical scavenging activities than α-tocopherol and butylated hydroxytoluene (BHT). The radical scavenging activity of N-decyl-N-(3,5- dimethoxy-4-hydroxybenzyl)-3-(3,4-dihydroxyphenyl) propanamide was 1.7 and 4 times higher than α-tocopherol and BHT, respectively. At the end of the storage period, the respective amounts of hydroperoxides in canola oil triacylglycerols (CTAG) fortified with α-tocopherol and BHT was 6.1 and 1.4 times higher, respectively, than CTAG containing the amide. The frying test showed that CTAG containing N-decyl-N-benzyl-3-(3,4-dihydroxybenzyl) propanamide was 1.3, 1.4, and 1.6 times more stable compared to oil fortified with dihydro-caffeic acid, α-tocopherol and BHT, respectively, as assessed by the amounts of the total polar compounds. Moreover, these compounds were remarkably thermally stable, making them suitable for frying applications.
Marine-derived 2-aminoimidazolone alkaloids. Leucettamine B-related polyandrocarpamines inhibit mammalian and protozoan DYRK & CLK kinases
Loa?c, Nadège,Attanasio, Eletta,Villiers, Beno t,Durieu, Emilie,Tahtouh, Tania,Cam, Morgane,Davis, Rohan A.,Alencar, Aline,Roué, Mélanie,Bourguet-Kondracki, Marie-Lise,Proksch, Peter,Limanton, Emmanuelle,Guiheneuf, Solène,Carreaux, Fran ois,Bazureau, Jean-Pierre,Klautau, Michelle,Meijer, Laurent
, (2017/11/10)
A large diversity of 2-aminoimidazolone alkaloids is produced by various marine invertebrates, especially by the marine Calcareous sponges Leucetta and Clathrina. The phylogeny of these sponges and the wide scope of 2-aminoimidazolone alkaloids they produce are reviewed in this article. The origin (invertebrate cells, associated microorganisms, or filtered plankton), physiological functions, and natural molecular targets of these alkaloids are largely unknown. Following the identification of leucettamine B as an inhibitor of selected protein kinases, we synthesized a family of analogues, collectively named leucettines, as potent inhibitors of DYRKs (dual-specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases) and potential pharmacological leads for the treatment of several diseases, including Alzheimer’s disease and Down syndrome. We assembled a small library of marine sponge- and ascidian-derived 2-aminoimidazolone alkaloids, along with several synthetic analogues, and tested them on a panel of mammalian and protozoan kinases. Polyandrocarpamines A and B were found to be potent and selective inhibitors of DYRKs and CLKs. They inhibited cyclin D1 phosphorylation on a DYRK1A phosphosite in cultured cells. 2-Aminoimidazolones thus represent a promising chemical scaffold for the design of potential therapeutic drug candidates acting as specific inhibitors of disease-relevant kinases, and possibly other disease-relevant targets.
