Biomimetic synthesis and HPLC-ECD analysis of the isomers of dracocephins A and B
| Autor: | György Kalaus, László Hazai, Ádám Szappanos, Sándor Antus, Áron Szigetvári, Ana Martins, Judit Müller, András Spaits, Anita Prechl, Zoltán Béni, Viktor Ilkei, György T. Balogh, Tibor Kurtán, Árpád Könczöl, Attila Mándi, Csaba Szántay, Attila Hunyadi, Miklós Dékány, Hedvig Bölcskei |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Naringenin
flavonoid alkaloids Flavonoid 010402 general chemistry dracocephins A–B 01 natural sciences ECD calculation Full Research Paper lcsh:QD241-441 chemistry.chemical_compound Dracocephalum rupestre lcsh:Organic chemistry Természettudományok Biomimetic synthesis HPLC–ECD Structural isomer Organic chemistry lcsh:Science Kémiai tudományok chemistry.chemical_classification Natural product Chromatography biology 010405 organic chemistry Chemistry Organic Chemistry Absolute configuration biology.organism_classification 0104 chemical sciences Chiral column chromatography absolute configuration lcsh:Q |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2523-2534 (2016) Beilstein Journal of Organic Chemistry |
| Popis: | Starting from racemic naringenin ((±)-1), a mixture of dracocephin A stereoisomers 6-(2”-pyrrolidinone-5”-yl)naringenin (±)-2a–d and its regioisomer, dracocephin B 8-(2”-pyrrolidinone-5”-yl)naringenin (±)-3a–d originally isolated from Dracocephalum rupestre, have been synthesized in a one-pot reaction. The separation of 2a–d and 3a–d was achieved by preparative HPLC. The four stereoisomers of each natural product were separated by analytical chiral HPLC and their absolute configuration was studied by the combination of HPLC–ECD measurements and TDDFT–ECD calculations. The synthesized flavonoid alkaloids were further characterized by physicochemical and in vitro pharmacological studies. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|