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

Autor: Viktor Ilkei, András Spaits, Anita Prechl, Áron Szigetvári, Zoltán Béni, Miklós Dékány, Csaba Szántay Jr, 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
Jazyk: angličtina
Rok vydání: 2016
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2523-2534 (2016)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.12.247
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.
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