A practical synthesis of 28a-homo-28a-selenolupane triterpenes and the corresponding selenosaponins containing d-mannose, l-arabinose, l-rhamnose, and d-idose moieties is described. Selenium containing triterpenes were obtained from the readily available 3-O-allyl-homobetulin mesylate by nucleophilic substitution with the selenocyanate ion which upon reduction of the -SeCN group afforded the free selenol. Glycosylation using classical Schmidt donors gave 1,2-trans selenosaponins as the main product as well as minute amounts of 1,2-cis isomers. This is one of the very few examples of the synthesis of selenoglycosides by direct glycosylation of free selenols. The studied selenol showed high resistance to air oxidation resulting in good stability during the synthesis of selenolupane derivatives. Cytotoxic activities of new homoselenolupane derivatives were also evaluated in vitro and revealed that some triterpenes exhibited an interesting profile against human cancer cell lines.
A series of lupane-type saponins bearing OSW-1 disaccharide unit as well as its regio- and stereoisomers were prepared and used for the structure-activity relationships (SAR) study. Unexpected preference for 1→4-linked regioisomers and an unusual inversion of the conformation of the sugar rings were noted. Cytotoxic activity of new lupane compounds was evaluated in vitro and revealed that some saponins exhibited an interesting bioactivity profile against human cancer cell lines. Influence of the protecting groups on the cytotoxicity was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds.
- MeSH
- antitumorózní látky chemická syntéza chemie farmakologie MeSH
- arabinosa chemie MeSH
- disacharidy chemická syntéza chemie farmakologie MeSH
- glykosylace MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- saponiny chemie MeSH
- stereoizomerie MeSH
- techniky syntetické chemie MeSH
- triterpeny chemie MeSH
- vodíková vazba MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Leaf extracts of Hedera helix L. are widely used in the treatment of upper respiratory diseases. The saponins a-hederin and hederacoside C are considered to be the main compounds responsible for the biological activity. a-Hederin and hederacoside C were determined in H. helix leaf extracts using a fast, simple and validated HPLC method. An XTerra MS C18 column and mobile phase composed of 10 mM ammonium acetate at pH 8.5 (adjusted with triethylamine) and acetonitrile were used for the chromatography at 1.2 mL min(-1). The column was kept at 30°C. Detection was performed at 220 nm. An approach utilizing a basic pH of the aqueous part of the mobile phase enabled analysis in 5 minutes in isocratic mode. The method was validated and used for the quality control of H. helix leaf ethanolic extracts.
- MeSH
- břečťan chemie MeSH
- kyselina olenalová analogy a deriváty chemie MeSH
- listy rostlin chemie MeSH
- reprodukovatelnost výsledků MeSH
- rostlinné extrakty chemie MeSH
- saponiny chemie MeSH
- vysokoúčinná kapalinová chromatografie metody MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Geografické názvy
- Česká republika MeSH
- Polsko MeSH
- Klíčová slova
- astragalan I, II, cykloastragenol, astragalosidy I-VIII, Astragalus mongholicus Bunge, Astragalus propinquus Schisch., huangqí (čín.), Astragali radix (Jap XI, ChinP IX),
- MeSH
- Astragalus propinquus * anatomie a histologie chemie MeSH
- autoimunitní nemoci MeSH
- dítě MeSH
- kořeny rostlin MeSH
- laktace MeSH
- lékové interakce MeSH
- lidé MeSH
- polysacharidy * aplikace a dávkování farmakologie chemie kontraindikace terapeutické užití MeSH
- preklinické hodnocení léčiv MeSH
- saponiny * aplikace a dávkování farmakologie chemie izolace a purifikace kontraindikace terapeutické užití MeSH
- těhotenství MeSH
- terapeutické užití MeSH
- zvířata MeSH
- Check Tag
- dítě MeSH
- lidé MeSH
- těhotenství MeSH
- zvířata 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
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.
Práce uvádí charakteristiku rodu Solidago (Asteraceae) a botanické popisy čtyř u nás se vyskytujících druhů včetně dvou subspecií druhu Solidago virgaurea L. Shrnuje dosavadní experimentální poznatky, které vedly na poli saponinů k objasnění struktur sapogeiůnů, monodesmosidických prosapogeninů, deacylovaných virgaureasaponinů 1 až 3, genuinních acylovaných saponinů 1 až 4 a solidagosaponinů I až XXIX. Genuinní saponiny druhu Solidago virgaurea L. jsou různě acylované estery převážně polygalakové kyseliny mono-, bi- a tridesmosidového typu. Práce také informuje o izolaci dvou fenolických biglukosidů leiocarposidu a virgaureasapoiúnu a referuje o prokázaných biologických aktivitách.
The review characterizes the plants of the genus Solidago (Asteraceae) and presents botanical descriptions of four species which occur in the Czech Republic, including two subspecies of Solidago uirgaurea L. It summarizes experimental data which resulted in the elucidation of the structure of sapogeiúns, monodesmosidic prosapogenins, deacylated virgauresaponins 1 to 3, genuine acylated triterpenoid sapomns 1 to 4, and solidagosaponins I to XXIX. Saponins of the species Solidago virgaurea are various acylated esters of prevalently polygalacic acid of mono-, bi- and tridesmosidic types. The paper also reports information about the isolation of two phenolic biglucosides leiocarposide and virgaureoside A and about demonstrated biological activities.
