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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Bibliographic Details
Main Authors: Ilkei Viktor
Spaits András
Prechl Anita
Szigetvári Áron
Béni Zoltán
Dékány Miklós
Szántay Csaba, ifj
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
Format: Article
Published: 2016
Series:BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 12
doi:10.3762/bjoc.12.247

mtmt:3143287
Online Access:http://publicatio.bibl.u-szeged.hu/10062
Description
Summary: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.
Physical Description:2523-2534
ISSN:1860-5397