Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00473961" target="_blank" >RIV/61388963:_____/17:00473961 - isvavai.cz</a>

Alternative codes found

RIV/61389030:_____/17:00473961 RIV/61389013:_____/17:00473961 RIV/60461373:22330/17:43902756

Result on the web

<a href="http://dx.doi.org/10.1016/j.steroids.2016.09.009" target="_blank" >http://dx.doi.org/10.1016/j.steroids.2016.09.009</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.steroids.2016.09.009" target="_blank" >10.1016/j.steroids.2016.09.009</a>

Result language

angličtina

Original language name

Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol

Original language description

Naturally occurring acylated beta-sitostetyl glucosides have been investigated for their novel properties. The synthetic protocol based on the literature data was improved and optimized. The main improveinent consists in employing systems of ionic liquids combined with organic solvents in lipase-mediated esterification of (3 beta)-stigmast-5-en-3-yl beta-D-glucopyranoside to get (3 beta)-stigmast-5-en-3-yl 6-O-acyl-beta-D-glucopyranosides. Maximum yields of these products were achieved with Candida antarctica lipase B immobilized on Immobead 150, recombinant from yeast, in absolute THE and in the presence of either ionic liquid [1-butyl-3-methyl imidazolium tetrafluoroborate ([BMIM]BF4) or 1-butyl-3-methyl imidazolium hexafluorophosphate ([BMIM]PF6)] employed. Pharmacological activity of (3 beta)-stigmast-5-en3-yl 6-O-acyl-beta-D-glucopyranosides was studied in tests on MCF7 tumor cell lines, the compounds displayed moderate activity which was higher than the activity of B-sitosterol. Supramolecular characteristics were discovered at (3 beta)-stigmast-5-en-3-yl 6-O-dodecanoyl-beta-D-glucopyranoside that formed supramolecular polymer through multiple H-bonds in a methanol/water system (60/40). Its formation was confirmed by the independent UV-vis measurements during certain time period, by variable temperature DOSY-NMR measurement in deuteriochloroform, and visualized by transmission electron microscopy (TEM) and atomic force microscopy (AFM) showing chiral helical structures and complex superassembly systems based on fibrous supramolecular polymer. In contrary, no such properties have been observed for the other two (3 beta)-stigmast-5-en-3-yl 6-O-acyl-beta-D-glucopyranosides under the given experimental conditions.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Steroids

ISSN

0039-128X

e-ISSN

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Volume of the periodical

117

Issue of the periodical within the volume

JAN

Country of publishing house

US - UNITED STATES

Number of pages

6

Pages from-to

38-43

UT code for WoS article

000392566800007

EID of the result in the Scopus database

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