The subject of this review article refers to the recent achievements in the investigation of pharmacological activity and supramolecular characteristics of betulinic acid and its diverse derivatives, with special focus on their cytotoxic effect, antitumor activity, and antiviral effect, and mostly covers a period 2015-2018. Literature sources published earlier are referred to in required coherences or from historical points of view. Relationships between pharmacological activity and supramolecular characteristics are included if such investigation has been done in the original literature sources. A wide practical applicability of betulinic acid and its derivatives demonstrated in the literature sources is also included in this review article. Several literature sources also focused on in silico calculation of physicochemical and ADME parameters of the developed compounds, and on a comparison between the experimental and calculated data.
A new and relatively simple method for purification of betulin from birch bark extract was developed in this study. Its five purification steps are based on the differential solubility of extract components in various solvents and their crystallization and/or precipitation, on their affinity for Ca(OH)2 in ethanol, and on the affinity of some impurities for silica gel in chloroform. In addition, all used solvents can be simply recycled. Betulin of more than 99% purity can be prepared by this method with minimal costs. Various observations including crystallization of betulin, changes in crystals during heating, and attempt of localization of betulin in outer birch bark are also described in this work. The original extract, fraction without betulinic acid and lupeol, amorphous fraction of pure betulin, final crystalline fraction of pure betulin and commercial betulin as a standard were employed to determine the antiproliferative/cytotoxic effect. We used WST-1 tetrazolium-based assays with triple negative breast cancer cell line BT-549. The decrease in cell survival showed clear relationship with the purity of the samples, being most pronounced using our final product of pure crystalline betulin. WST-1 proliferation/cytotoxicity test using triple negative breast cancer cell line BT-549 clearly showed the importance of purity of betulin for biological experiments and, apparently, for its medicinal use.
- MeSH
- bříza chemie MeSH
- krystalizace MeSH
- kůra rostlin chemie MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- proliferace buněk účinky léků MeSH
- triple-negativní karcinom prsu farmakoterapie patologie MeSH
- triterpeny chemie izolace a purifikace farmakologie terapeutické užití MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
The aim of our study was to increase the extraction efficiency of carvacrol, rosmarinic, oleanolic and ursolic acid from the different species of oregano herbs (Origanum onites L., Origanum vulgare spp. hirtum and Origanum vulgare L.). Various extraction methods (ultrasound-assisted, heat-reflux, continuous stirring, maceration, percolation) and extraction conditions (different solvent, material:solvent ratio, extraction temperature, extraction time) were used, and the active substances were determined by HPLC. The lowest content of carvacrol, rosmarinic, oleanolic and ursolic acid was obtained by percolation. During heat-reflux extraction, the content of active substances depended on the solvent used: ethanol/non-aqueous solvent (glycerol or propylene glycol) mixture was more effective compared with ethanol alone. The results showed that for each species of oregano the most optimal extraction method should be selected to maximize the content of biologically active substances in the extracts.
- MeSH
- cinnamáty izolace a purifikace MeSH
- depsidy izolace a purifikace MeSH
- dobromysl (rod) chemie klasifikace MeSH
- kyselina olenalová izolace a purifikace MeSH
- molekulární struktura MeSH
- monoterpeny izolace a purifikace MeSH
- rostlinné extrakty chemie MeSH
- rozpouštědla MeSH
- triterpeny izolace a purifikace MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
Identification of molecular species of various N-acylated bacteriohopanehexol-mannosamides from the thermophilic bacterium Alicyclobacillus acidoterrestris by semipreparative HPLC and by RP-HPLC with ESI is described. We used triple-quadrupole type mass spectrometer, (1)H and (13)C NMR for analyzing this complex lipid. CD spectra of two compounds (model compound--7-deoxy-D: -glycero-D: -allo-heptitol obtained by stereospecific synthesis, and an isolated derivative of hopane) were also measured and the absolute configuration of both compounds was determined. On the basis of all the above methods, we identified the full structure of a new class of bacteriohopanes, represented by various N-acylated bacteriohopanehexol-mannosamides.
- MeSH
- acylace MeSH
- Alicyclobacillus chemie růst a vývoj MeSH
- amidy analýza chemie izolace a purifikace MeSH
- hmotnostní spektrometrie s elektrosprejovou ionizací MeSH
- magnetická rezonanční spektroskopie MeSH
- mannosa analýza chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- tandemová hmotnostní spektrometrie MeSH
- teplota MeSH
- triterpeny analýza chemie izolace a purifikace MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Twelve lupane, 18alpha-oleanane, and des-E-lupane derivatives (1a-5b) were either extracted from natural sources or synthesized from betulinic acid (1a) and betulin (2). Compounds 1b, 1c, 3b, 3c, 4b, 4c, 5a, and 5b were then used as starting materials for further synthesis of a series of pyrazines and benzopyrazines (6a-18); 20 of them are new (6a-6e, 7a-7d, and 10a-18). Activity of pyrazine 6a against the T-lymphoblastic leukemia cell line CEM encouraged us to synthesize several new esters (6b-6d) to study structure-activity relationships with respect to substitution of the carboxyl group at position 28. The synthesized compounds were tested for cytotoxicity against a variety of cancer cell lines of different histogenetic origin, and the results were compared with cytotoxicity of the known starting compounds. Significant cytotoxic activity against A 549, K 562, and multidrug-resistant K 562-tax cell lines was found in pyrazines 6a, 6d, and 6e.
- MeSH
- chemorezistence MeSH
- financování organizované MeSH
- fytogenní protinádorové látky farmakologie chemická syntéza chemie MeSH
- leukemie T-buněčná MeSH
- lidé MeSH
- mnohočetná léková rezistence MeSH
- molekulární struktura MeSH
- nádorové buňky kultivované MeSH
- pyraziny farmakologie chemická syntéza chemie MeSH
- screeningové testy protinádorových léčiv MeSH
- triterpeny farmakologie chemie izolace a purifikace MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- MeSH
- akridinová oranž toxicita MeSH
- antimutagenní látky farmakologie izolace a purifikace MeSH
- Cynara chemie MeSH
- Euglena gracilis genetika účinky léků MeSH
- finanční podpora výzkumu jako téma MeSH
- molekulární struktura MeSH
- ofloxacin analýza toxicita MeSH
- saponiny chemie izolace a purifikace MeSH
- triterpeny izolace a purifikace MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
Práca sa zaoberá izoláciou látok z petroléterového a chloroformového extraktu listov pajazmínuvencového (Philadelphus coronarius L., Saxifragaceae). Z petroléterového extraktu listov tejtorastliny bol izolovaný uvaol a 3b,28-dihydroxyolean-11(12),13(18)-dién. Z chloroformového extraktuboli izolované kumaríny (umbeliferón a skopolín), stigmasteryl-3b-D-glukozid a uhľovodík alkánového typu C29 H60. Látky boli identifikované na základe spektrálnych údajov, porovnaním soštandardami a literatúrnymi údajmi.
The paper deals with the isolation of constituents from light petrol and chloroform extracts of theleaves of Philadelphus coronarius L., Saxifragaceae. From the light petrol extract uvaol and3b,28-dihydroxyoleanane-11(12),13(18)-diene were isolated, while coumarins (umbelliferone, scopolin), stigmasteryl-3b-D-glucoside and the alcane type carbohydrate-C29H60 were isolated from thechloroform extract. The isolated compounds were identified by spectroscopic means and by comparison with standards and the literature data.
Z etanolového extraktu nerozvinutých púčikov Cynara cardunculus L (Asteraceae) sa izolovali dvamonodezmozidové saponíny-cynarasaponín B a nový cynarasaponín K. Ich štruktúra bola určenána základe spektrálnych meraní, porovnaním údajov v literatúre a chromatografickým porovnanímso štandardami.
From an ethanolic extract of the flower buds of Cynara cardunculus L. (Asteraceae), two monodes-mosidic saponins, cynarasaponin B and a new cynarasaponin K, were isolated. The isolatedcompounds were identified by spectroscopic means and by comparison with standards and theliterature data.
