PhD Scientific Days 2017

Oral Presentations: Pharmaceutical

Homonipecotic acid derivatives: new natural products isolated from spiny restharrow

Előadó neve

Gampe, Nóra

Előadó munkahelye

Department of Pharmacognosy

Előadó telefonszáma

06204280658

Előadó e-mail címe

gampe.nore@gmail.com

Az előadás címe

Homonipecotic acid derivatives: new natural products isolated from spiny restharrow

Szerző(k) neve és munkahelye

Nóra Gampe, András Darcsi, Szabolcs Béni, László Kursinszki
Semmelweis University, Department of Pharmacognosy, Budapest, Hungary

Szekció

Oral Presentations: Pharmaceutical

Data of the presenter

Doctoral School: Pharmaceutical Sciences Doctoral School
Program: Modern Trends in Pharmaceutical Scientific Research
Supervisors: Dr. Szabolcs Béni, Dr. László Kursinszki
E-mail addres: gampe.nora@gmail.com

Text of the abstract

The root of spiny restharrow (Ononis spinosa L.) is used as a diuretic remedy in traditional medicine and the drug is official in both the Hungarian and the European Pharmacopoeia. The most important secondary metabolites in restharrow root are isoflavonoids. These molecules can be found in the form of glucosides, glucoside malonates and rarely, glucoside acetates. During thorough HPLC-MS/MS investigations characteristic peaks of nitrogen containing isoflavonoid derivatives could be observed. Beforehand neither alkaloids nor nitrogen containing other secondary metabolites have been identified in the extract of restharrow root. Based on product ion spectra and literature information, the structure of the isoflavonoid moiety could be identified unambiguously, however, the elucidation of the nitrogen containing part could not be executed using mass spectrometry exclusively. For the preparative isolation of the molecules of interest the aqueous-methanolic extract was purified on weak cation-exchange cartridges. The eluted fraction was further separated by preparative and analytical HPLC. With the help of 1D and 2D NMR experiments six isoflavonoid glucoside azepane-3-carboxylates could be identified. Moreover, the homologous piperidine-3-carboxylate esters were also detected and tentatively identified in the extract based on the MS/MS spectra. The biosynthetic origin of these heterocyclic compounds is unknown as this is the first isolation of these unique beta amino acids from natural source. These molecules are however common structural motifs of anticonvulsive medicines suggesting their potential bioactivity.
Acknowledgement: OTKA-PD-109373

Kind

Szabad

Előadás fájl jóváhagyás

nem rendelkezett róla

Előadó

1097

Authors (legacy)

Nóra Gampe, András Darcsi, Szabolcs Béni, László Kursinszki
Semmelweis University, Department of Pharmacognosy, Budapest, Hungary