Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

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 reacti...

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Detalles Bibliográficos
Autores principales: Ilkei, Viktor, Spaits, András, Prechl, Anita, Szigetvári, Áron, Béni, Zoltán, Dékány, Miklós, Szántay, Csaba, Müller, Judit, Könczöl, Árpád, Szappanos, Ádám, Mándi, Attila, Antus, Sándor, Martins, Ana, Hunyadi, Attila, Balogh, György Tibor, Kalaus (†), György, Bölcskei, Hedvig, Hazai, László, Kurtán, Tibor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238559/
https://www.ncbi.nlm.nih.gov/pubmed/28144321
http://dx.doi.org/10.3762/bjoc.12.247
Descripción
Sumario: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.

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