62442-62-0Relevant articles and documents
Metabolomic profiling of the immune stimulatory effect of eicosenoids on PMA-differentiated THP-1 cells
Alqarni, Abdulmalik M.,Dissanayake, Tharushi,Nelson, David J.,Parkinson, John A.,Dufton, Mark J.,Ferro, Valerie A.,Watson, David G.
, (2019)
Honey bee venom has been established to have significant effect in immunotherapy. In the present study, (Z)-11-eicosenol-a major constituent of bee venom, along with its derivations methyl cis-11-eicosenoate and cis-11-eicosenoic acid, were synthesised to investigate their immune stimulatory effect and possible use as vaccine adjuvants. Stimuli that prime and activate the immune system have exerted profound effects on immune cells, particularly macrophages; however, the effectiveness of bee venom constituents as immune stimulants has not yet been established. Here, the abilities of these compounds to act as pro-inflammatory stimuli were assessed, either alone or in combination with lipopolysaccharide (LPS), by examining the secretion of tumour necrosis factor-α (TNF-α) and the cytokines interleukin-1β (IL-1β), IL-6 and IL-10 by THP-1 macrophages. The compounds clearly increased the levels of IL-1β and decreased IL-10, whereas a decrease in IL-6 levels suggested a complex mechanism of action. A more in-depth profile of macrophage behaviour was therefore obtained by comprehensive untargeted metabolic profiling of the cells using liquid chromatography mass spectrometry (LC-MS) to confirm the ability of the eicosanoids to trigger the immune system. The level of 358 polar and 315 non-polar metabolites were changed significantly (p 0.05) by all treatments. The LPS-stimulated production of most of the inflammatory metabolite biomarkers in glycolysis, the tricarboxylic acid (TCA) cycle, the pentose phosphate pathway, purine, pyrimidine and fatty acids metabolism were significantly enhanced by all three compounds, and particularly by methyl cis-11-eicosenoate and cis-11-eicosenoic acid. These findings support the proposed actions of (Z)-11-eicosenol, methyl cis-11-eicosenoate and cis-11-eicosenoic acid as immune system stimulators.
Asymmetric synthesis of cytotoxic sponge metabolites R-strongylodiols A and B and an analogue
Kirkham, James E.D.,Courtney, Timothy D.L.,Lee, Victor,Baldwin, Jack E.
, p. 7219 - 7232 (2007/10/03)
The asymmetric synthesis of the marine sponge natural products R-strongylodiols A R-1 and B R-2, using a minimum protection strategy, is described. Two approaches were examined and the Noyori asymmetric reduction of ynones was found to be successful for installing the chirality of the natural products. Analogue R-32 was also prepared. In addition, asymmetric alkynylation of aldehydes is briefly reviewed.
Enantioselective total synthesis of (R)-strongylodiols A and B
Reber, Stefan,Kn?pfel, Thomas F.,Carreira, Erick M.
, p. 6813 - 6817 (2007/10/03)
We describe an expeditious enantioselective total synthesis of the acetylenic marine natural products (R)-strongylodiols A and B. Central to the strategy is the use of Zn(OTf)2, amine base, and N-methyl ephedrine to mediate the direct addition of a 1,3-diyne to two long-chain aliphatic aldehydes in useful selectivities and yields.
