Beilstein Journal of Organic Chemistry (Nov 2016)
Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B
- 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
Affiliations
- Viktor Ilkei
- Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest, Hungary
- András Spaits
- Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest, Hungary
- Anita Prechl
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- Áron Szigetvári
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- Zoltán Béni
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- Miklós Dékány
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- Csaba Szántay Jr
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- Judit Müller
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- Árpád Könczöl
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- Ádám Szappanos
- Department of Organic Chemistry, University of Debrecen, P. O. Box 400, H-4002 Debrecen, Hungary
- Attila Mándi
- Department of Organic Chemistry, University of Debrecen, P. O. Box 400, H-4002 Debrecen, Hungary
- Sándor Antus
- Department of Organic Chemistry, University of Debrecen, P. O. Box 400, H-4002 Debrecen, Hungary
- Ana Martins
- Department of Medical Microbiology and Immunobiology, University of Szeged, Dóm tér 9, H-6720 Szeged, Hungary
- Attila Hunyadi
- Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary
- György Tibor Balogh
- Gedeon Richter Plc., Gyömrői út 19-21, H-1103 Budapest, Hungary
- György Kalaus (†)
- Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest, Hungary
- Hedvig Bölcskei
- Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest, Hungary
- László Hazai
- Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest, Hungary
- Tibor Kurtán
- Department of Organic Chemistry, University of Debrecen, P. O. Box 400, H-4002 Debrecen, Hungary
- DOI
- https://doi.org/10.3762/bjoc.12.247
- Journal volume & issue
-
Vol. 12,
no. 1
pp. 2523 – 2534
Abstract
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.
Keywords
- absolute configuration
- Dracocephalum rupestre
- dracocephins A–B
- ECD calculation
- flavonoid alkaloids
- HPLC–ECD
