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.
Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities
Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto
supporting information, p. 2544 - 2550 (2019/11/13)
Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.
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.
Asymmetric synthesis of cytotoxic sponge metabolites R-strongylodiols A and B
Kirkham, James E. D.,Courtney, Timothy D. L.,Lee, Victor,Baldwin, Jack E.
, p. 5645 - 5647 (2007/10/03)
The asymmetric synthesis of the marine sponge natural products, R-strongylodiols A 1 and B 2 using a minimum protection strategy is described. The chirality of the natural products was introduced via the Noyori asymmetric reduction of ynones.
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.
Applications of olefin cross metathesis to commercial products
Pederson, Richard L.,Fellows, Ingrid M.,Ung, Thay A.,Ishihara, Hiroki,Hajela, Sharad P.
, p. 728 - 735 (2007/10/03)
In this paper, we will demonstrate the value of olefin cross metathesis as an effective synthetic tool for applications in the agrochemical and pharmaceutical industries. First, we will demonstrate the usefulness of cross metathesis reactions in the efficient synthesis of the major component of the Peach Twig Borer pheromone and the of Omnivorous Leafroller pheromone, insect pheromones are environmentally friendly pest-controlling agents. Second, we will demonstrate highly efficient cross metathesis routes into novel α,β-unsaturated carbonyl intermediates. These novel α,β-unsaturated carbonyl intermediates can be further functionalized into pharmaceutical compounds that are difficult to prepare by the traditional synthetic methodologies. This paper highlights key catalyst-substrate reactivity variations with different ruthenium olefin metathesis catalysts, highlights cross metathesis reactions and techniques and highlights an efficient ruthenium catalyst removal technique.
Pheromones via organoboranes: Part IV - Synthesis of (Z)-9-tricosene (Muscalure)
Dhillon, Ranjit S.,Singh, Rupinder P.,Singh, Jasvinder
, p. 718 - 721 (2007/10/03)
Synthesis of (Z)-9-tricosene (muscalure) (9) is reported starting from oleyl alcohol by two carbon homologation via dianion of phenoxyacetic acid followed by reduction (LAH), oxidation (PCC) and Grignard reaction.
