Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

Sidoryk, Katarzyna; Rárová, Lucie; Oklešťková, Jana; Pakulski, Zbigniew; Strnad, Miroslav; Cmoch, Piotr; Luboradzki, Roman

doi:10.1039/c6ob01938b

Cited by 25 publications

(13 citation statements)

References 59 publications

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“…They do this apoptotic activity through mechanism encompassing both microtubule and Akt inhibition (Krishnegowda et al 2011). A compound selenocyanate containing triterpenes based on homobetulin scaffold was developed and showed antiproliferative activity in the low µM range against non-tumor cells (Sidoryk et al 2016).…”

Section: Selenocyantesmentioning

confidence: 99%

Selenium and selenoproteins: it’s role in regulation of inflammation

2020

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Selenium is an essential immunonutrient which holds the human's metabolic activity with its chemical bonds. The organic forms of selenium naturally present in human body are selenocysteine and selenoproteins. These forms have a unique way of synthesis and translational coding. Selenoproteins act as antioxidant warriors for thyroid regulation, male-fertility enhancement, and anti-inflammatory actions. They also participate indirectly in the mechanism of wound healing as oxidative stress reducers. Glutathione peroxidase (GPX) is the major selenoprotein present in the human body, which assists in the control of excessive production of free radical at the site of inflammation. Other than GPX, other selenoproteins include selenoprotein-S that regulates the inflammatory cytokines and selenoprotein-P that serves as an inducer of homeostasis. Previously, reports were mainly focused on the cellular and molecular mechanism of wound healing with reference to various animal models and cell lines. In this review, the role of selenium and its possible routes in translational decoding of selenocysteine, synthesis of selenoproteins, systemic action of selenoproteins and their indirect assimilation in the process of wound healing are explained in detail. Some of the selenium containing compounds which can acts as cancer preventive and therapeutics are also discussed. These compounds directly or indirectly exhibit antioxidant properties which can sustain the intracellular redox status and these activities protect the healthy cells from reactive oxygen species induced oxidative damage. Although the review covers the importance of selenium/selenoproteins in wound healing process, still some unresolved mystery persists which may be resolved in near future.

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Section: Selenocyantesmentioning

confidence: 99%

Selenium and selenoproteins: it’s role in regulation of inflammation

2020

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“…Selenoglycosides comprise a subset of selenium‐containing compounds and are known to possess a diverse set of useful biological activities (Figure ). Their potential application in the development of novel carbohydrate‐based therapeutics is suggested by their anti‐metastatic ( 1 ), immunostimulatory ( 2 ), and anti‐tumor activities. Additionally, selenoglycosides demonstrate their utility as probes for studying carbohydrate–protein interactions .…”

Section: Figurementioning

confidence: 99%

Stereoretentive Reactions at the Anomeric Position: Synthesis of Selenoglycosides

et al. 2018

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Reported is the stereospecific cross-coupling of anomeric stannanes with symmetrical diselenides, resulting in the synthesis of selenoglycosides with exclusive anomeric control. The reaction proceeds without the need for directing groups and is compatible with free hydroxy groups as demonstrated in the preparation of glycoconjugates derived from mono-, di-, and trisaccharides and peptides (35 examples). Given its generality and broad substrate scope, the glycosyl cross-coupling method presented herein can find use in the synthesis of selenium-containing glycomimetics and glycoconjugates.

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“…Recently, Baran and co-workers have developed a late-stage diversication approach for improving the pharmacokinetic properties of BA via C-H oxidation through a combination of chemical and enzymatic reactions. 11 In parallel to these pioneering studies, we 1,12-18 and others [19][20][21][22][23] have been interested in coupling diverse hydrosoluble sugar moieties at the C-3 and/or C-28 positions of BA and other members of the lupane-type triterpenoid family such as betulin and lupeol. Among other things, we have shown that synthetic BA saponins bearing L-rhamnopyranose (Rha) residues at the C-3 position were potent cytotoxic agents 15 devoid of hemolytic activity 12 as compared to oleanane-type saponins.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins

et al. 2019

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Betulinic acid and ursolic acid are ubiquitous, naturally-occurring triterpenoids exhibiting various pharmacological activities including cytotoxic and anti-inflammatory activities. However, these triterpenoids display unfavorable pharmacokinetic properties as well as low aqueous solubility. It has been shown that the presence of a-L-rhamnose moieties positively modulates the anticancer activity of secondary metabolites. Herein we report the synthesis and in vitro evaluation of cytotoxic and antiinflammatory activities of a series of rhamnose-containing ursolic and betulinic acid saponins. Relying on Schmidt's normal and inverse procedures, monorhamnosides, (1/4)-linked dirhamnosides as well as branched trirhamnosides and tetrarhamnosides were synthesized in high yields with full control of stereoselectivity. A betulinic acid saponin bearing a 3-O-a-L-rhamnopyranosyl-(1/4)-a-Lrhamnopyranosyl residue was found to be a potent cytotoxic agent against human colorectal adenocarcinoma cells without damaging the healthy cells (selectivity ratio > 20) whereas rhamnosecontaining ursolic acid saponins potently inhibited NO overproduction induced by LPS-stimulated macrophages. Our results reveal that rhamnose-containing ursolic and betulinic acid saponins represent promising therapeutic agents.

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Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

Cited by 25 publications

References 59 publications

Selenium and selenoproteins: it’s role in regulation of inflammation

Selenium and selenoproteins: it’s role in regulation of inflammation

Stereoretentive Reactions at the Anomeric Position: Synthesis of Selenoglycosides

Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins

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