scholarly journals Chemo-enzymatic synthesis of 3-O- (β-d-glycopyranosyl)-sn-glycerols and their evaluation as preservative in cosmetics

2017 ◽  
Vol 89 (9) ◽  
pp. 1295-1304 ◽  
Author(s):  
Laure Guillotin ◽  
Perrine Cancellieri ◽  
Pierre Lafite ◽  
Ludovic Landemarre ◽  
Richard Daniellou

Abstractd-Glycopyranosyl glycerols are common natural products and exhibit strong biological properties, notably as moisturizing agents in cosmetics. Their chemical synthesis remains tedious thus decreasing their potential industrial and economic development, as well as the study of their structure-function relationships. In this work, the chemo-enzymatic synthesis of three enantiopure 3-O-(β-d-glycopyranosyl)-sn-glycerols was efficiently performed using an original glycosidase from Dictyoglomus thermophilum and their preservatives properties were assessed using a challenge test method. Amongst them, the 3-O-(β-d-glucopyranosyl)-sn-glycerol exhibited a specific anti-fungus activity.

Marine Drugs ◽  
2018 ◽  
Vol 16 (9) ◽  
pp. 294 ◽  
Author(s):  
Iván Cheng-Sánchez ◽  
Francisco Sarabia

Glycolipids represent a broad class of natural products structurally featured by a glycosidic fragment linked to a lipidic molecule. Despite the large structural variety of these glycoconjugates, they can be classified into three main groups, i.e., glycosphingolipids, glycoglycerolipids, and atypical glycolipids. In the particular case of glycolipids derived from marine sources, an impressive variety in their structural features and biological properties is observed, thus making them prime targets for chemical synthesis. In the present review, we explore the chemistry and biology of this class of compounds.


Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 765
Author(s):  
Nan Hu ◽  
Lorenzo V. White ◽  
Ping Lan ◽  
Martin G. Banwell

The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic targets since the mid-1950s. Such efforts continue unabated and more recent studies on these alkaloids have focused on using them as vehicles for showcasing the utility of new synthetic methods. This review provides a comprehensive survey of the nearly seventy-year history of these synthetic endeavors.


2013 ◽  
Vol 55 (1) ◽  
pp. 87-93 ◽  
Author(s):  
Cinzia Cancellieri ◽  
Nicoletta Caronni ◽  
Alessandro Vacchini ◽  
Benedetta Savino ◽  
Elena M. Borroni ◽  
...  

2006 ◽  
pp. 51-89 ◽  
Author(s):  
Steven V. Ley ◽  
Ian R. Baxendale ◽  
Deborah A. Longbottom ◽  
Rebecca M. Myers

2021 ◽  
Vol 18 ◽  
Author(s):  
Sarah Kappler ◽  
Andreas Siebert ◽  
Uli Kazmaier

Introduction: Miuraenamides belong to marine natural compounds with interesting biological properties. Materials and Methods: They initiate polymerization of monomeric actin and therefore show high cytotoxicity by influencing the cytoskeleton. New derivatives of the miuraenamides have been synthesized containing a N-methylated amide bond instead of the more easily hydrolysable ester in the natural products. Results: Incorporation of an aromatic side chain onto the C-terminal amino acid of the tripeptide fragment also led to highly active new miuraenamides. Conclusion: We could show that the ester bond of the natural product miuraenamide can be replaced by an N-methyl amide. The yields in the cyclization step are high and generally much better that with the corresponding esters. On the other hand, the biological activity of the new amide analogs are lower compared to the natural products, but the activity can significantly be increased by incorporation of a p-nitrophenyl group at the C-terminus of the peptide fragment.


Synlett ◽  
2021 ◽  
Author(s):  
Gustav J. Wørmer ◽  
Thomas Bjørnskov Poulsen

Piperidine alkaloids continue to challenge the synthetic community by featuring densely functionalized scaffolds which often requires careful chemical orchestration. Streptazone A and abikoviromycin are small and highly functionalized piperidine alkaloids both accommodating Michael acceptors and a labile epoxide. These moieties are loaded into a [4.3.0] bicyclic core also present in other structurally related natural products including the well-known piperidine alkaloid streptazolin. Herein, we cover ring-closing strategies employed in prior streptazolin syntheses, provide a concise overview of structures, biological properties and biosyntheses of selected [4.3.0] piperidine alkaloids, and finally we disclose a complete coverage of our recent asymmetric syntheses of streptazone A and abikoviromycin.


Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 492 ◽  
Author(s):  
Susana Cardoso

Antioxidants are under the research spotlight because of their potential to prevent oxidative stress as well as for their versatile biological properties that grant them multiple industrial applications [...]


2019 ◽  
Vol 45 (1) ◽  
pp. 15-28 ◽  
Author(s):  
Murugan Rajan ◽  
Allen Joseph Anthuvan ◽  
Kasipandi Muniyandi ◽  
Naveen Kumar Kalagatur ◽  
Saravanan Shanmugam ◽  
...  

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