A new method, reversed phase liquid chromatography with off-line surface-assisted laser desorption/ionization mass spectrometry (RPLC-SALDI MS) for the determination of brassicasterol (BR), cholesterol (CH), stigmasterol (ST), campesterol (CA) and β-sitosterol (SI) in oil samples has been developed. The sample preparation consisted of alkaline saponification followed by extraction of the unsaponificable fraction with diethyl ether. The recovery of the sterols ranged from 91 to 95% with RSD less than 4%. Separation of the five major sterols on a C18 column using methanol-water gradient was achieved in about 10min. An on-line UV detector was employed for the initial sterol detection prior to effluent deposition using a laboratory-built spotter with 1:73 splitter. Off-line SALDI MS was then applied for mass determination/identification and quantification of the separated sterols. Ionization of the nonpolar analytes was achieved by silver ion cationization with silver nanoparticles used as the SALDI matrix providing limits of detection 12, 6 and 11fmol for CH, ST and SI, respectively. Because of the incorporated splitter, the effective limits of detection of the RPLC-SALDI MS analysis were 4, 3 and 4pmol (or 0.08, 0.06 and 0.08μg/mL) for CH, ST and SI, respectively. For quantification, 6-ketocholestanol (KE) was used as the internal standard. The method has been applied for the identification and quantification of sterols in olive, linseed and sunflower oil samples. The described off-line coupling of RPLC to SALDI MS represents an alternative to GC-MS for analysis of nonpolar compounds.
- MeSH
- cholestadienoly chemie izolace a purifikace MeSH
- cholesterol analogy a deriváty chemie izolace a purifikace MeSH
- chromatografie s reverzní fází metody normy MeSH
- fytosteroly chemie izolace a purifikace MeSH
- ketocholesteroly chemie izolace a purifikace MeSH
- lněný olej analýza chemie MeSH
- oleje rostlin analýza chemie MeSH
- referenční standardy MeSH
- sitosteroly chemie izolace a purifikace MeSH
- spektrometrie hmotnostní - ionizace laserem za účasti matrice metody normy MeSH
- stigmasterol chemie izolace a purifikace MeSH
- stříbro chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Three new polyamine conjugates with stigmasterol [(3β,22E)-stigmasta-5,22-dien-3-ol] were synthesized and subjected to basic antimicrobial and cytotoxic tests. The conjugate derived from spermine, (3β,22E)-stigmasta-5,22-dien-3-yl 4(12-amino-4,9-diaza-dodecylamino)-4-oxobutanoate (5c), displayed considerable antimicrobial activity on Staphylococcus aureus at low concentration (50 μg mL(-1)). The cytotoxic activity was tested on cells of human T-lymfoblastic leukemia (IC(50)=35.8 ± 10.3 μM (5c) and IC(50)=35.9 ± 5.7 μM (5b)) and normal human fibroblasts (IC(50)=38.0 ± 2.8 μM (5c) and IC(50)=45.5 ± 1.9 μM (5b)). Conjugate 5a displayed no activity in both tests.
- MeSH
- antibakteriální látky chemická syntéza chemie farmakologie MeSH
- chemické jevy MeSH
- kyseliny karboxylové chemie MeSH
- lidé MeSH
- molekulární konformace MeSH
- molekulární modely MeSH
- nádorové buněčné linie MeSH
- polyaminy chemie MeSH
- protinádorové látky chemická syntéza chemie farmakologie MeSH
- racionální návrh léčiv MeSH
- Staphylococcus aureus účinky léků MeSH
- stigmasterol chemická syntéza chemie farmakologie MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Conjugates consisting of stigmasterol and L-phenylalanine, interconnected through short-chained dicarboxylic acyls by ester and amide bonds, respectively, were synthesized as potential low molecular weight/mass organic gelators (LMWGs/LMMGs). Their physico-chemical properties were subjected to investigation, especially their ability to form gels reversibly based on changes of the environmental conditions. Other self-assembly properties detectable by UV-VIS traces were measured in systems consisting of two miscible solvents (water/acetonitrile) with varying solvent ratios and using constant concentrations of the studied compounds. Partition and diffusion coefficients and solubility in water were calculated for the target conjugates. The conjugate 3a was the only compound from this series capable of forming a gel in 1-octanol. All three conjugates 3a-3c displayed supramolecular characteristics in the UV-VIS spectra.
- MeSH
- 1-oktanol chemie MeSH
- amidy chemie MeSH
- estery chemie MeSH
- fenylalanin chemie MeSH
- gely chemická syntéza chemie MeSH
- molekulární struktura MeSH
- molekulová hmotnost MeSH
- organické látky chemická syntéza chemie MeSH
- rozpouštědla chemie MeSH
- stigmasterol chemická syntéza chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
