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

• DOI: 10.3762/bjoc.12.247
• Publication Date: 2016-11-24T14:38:00Z
• Authors: Viktor Ilkei; András Spaits; Anita Prechl; Áron Szigetvári; Zoltán Béni; Miklós Dékány; Csaba Szántay; Judit Müller; Árpád Könczöl; Ádám Szappanos; Attila Mándi; Sándor Antus; Ana Martins; Attila Hunyadi; György Tibor Balogh; György Kalaus (†); Hedvig Bölcskei; László Hazai; Tibor Kurtán
• Keywords: Structural isomer; Natural product; Absolute Configuration

Starting from racemic naringenin ((±)- 1 ), a mixture of dracocephin A stereoisomers 6-(2”-pyrrolidinone-5”-yl)naringenin (±)- 2a–d and its regioisomer, B 8-(2”-pyrrolidinone-5”-yl)naringenin 3a–d originally isolated Dracocephalum rupestre , have been synthesized in one-pot reaction. The separation was achieved by preparative HPLC. four each natural product were separated analytical chiral HPLC their absolute configuration studied the combination HPLC–ECD measurements TDDFT–ECD calculations. flavonoid alkaloids further characterized physicochemical vitro pharmacological studies.