The structures of steroidal glycosides from Veronica Chamaedrys L
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MARCENCO-CICANCI, Alexandra. The structures of steroidal glycosides from Veronica Chamaedrys L. In: International Conference of Young Researchers , Ed. 8, 11-12 noiembrie 2010, Chişinău. Chişinău: Tipogr. Simbol-NP SRL, 2010, Ediția 8, p. 25. ISBN 978-9975-9898-4-8..
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International Conference of Young Researchers
Ediția 8, 2010
Conferința "International Conference of Young Researchers "
8, Chişinău, Moldova, 11-12 noiembrie 2010

The structures of steroidal glycosides from Veronica Chamaedrys L


Pag. 25-25

Marcenco-Cicanci Alexandra
 
Institute of Genetics, Physiology and Plant Protection of the Moldovan Academy of Sciences
 
 
Disponibil în IBN: 14 aprilie 2021


Rezumat

The genus Veronica is widely distributed in Europe and Asia and belongs to the family Scrophulariaceae [1-2]. Previously we had reported phenylethanoid and iridoid glycosides isolated from Veronica chamaedrys L. plants [3]. To our knowledge, this plant has never been studied before on steroidal glycosides. That is why the aim of our work was the isolation of steroidal glycosides from Veronica chamaedrys L. and elucidation of their chemical structures. From 1600 g of fresh plants by extraction with boiling water 10.3 g of steroidal glycosides were obtained, which is 0.64 % from the weight of raw plant material. The content of steroidal glycosides on the over dry weight is 4.29 %. After full acid hydrolysis of the sum of glycosides the obtained aglycones were analyzed by physicochemical methods and 1H and 13C-NMR spectroscopy. In the result of these analyses, sarsasapogenin, yamogenin, isonuatigenin and nuatigenin were identified as aglycones. In the hydrolysate part by paper and TLC chromatography glucose and rhamnose were identified as units of monosaccharides. The sum of glycosides was subjected to gel filtration on Sephadex G–50 and G–25 and then chromatografied on silica gel column (70–230 mesh, Merck). As a result, a number of chromatographic fractions was received [I (210 mg), II (500 mg), III (470 mg), IV (300 mg)], differing by their chromatographic mobility. Low-polarity fractions I and II were submitted to HPLC on a Waters XTerra Prep MS C18 column (C-18, μ-Bondapack, 300 x 7.8 mm i.d., the flow rate was 1.5 μL/min), using MeOH:H2O 80:20 for I, and 85:15 for II (isocratic conditions). Individual glycosides, named by us chamaedrosides A, A1, A2 and B were obtained from fraction I, and chamaedrosides C, C1, C2 and E – from II. Chamaedrosides A, A1, A2, C, C1, C2 give a positive reaction with Sannie and negative with Ehrlich reagents that allowed us to include them to the glycosides of spirostane series. Chamaedrosides B and E give positive Sannie and Ehrlich test, on this basis we have assigned them to the glycosides of furostane series. According to the physicochemical constants, IR- and MS-spectroscopy data and data of 1H- and 13C-NMR spectral analysis (HMBC, HSQC, ROESY, 1H-1H COSY), the structure of chamaedroside A was elucidated as 3-Oβ-D-glucopyranoside-(25S)-5β-spirostan-3β-ol, chamaedroside A1 – 3-O-β-D-glucopyranoside-(25S)-spirost-5-en3β-ol, chamaedroside A2 – 3-O-β-D-glucopyranoside-22,25-epoxy-(22S,25S)-furost-5-en-3β,26-diol, chamaedroside B – 3-O-β-D-glucopyranoside-(25S)-5β-furostan-3β, 22α, 26-triol-26-O-β-D-glucopyranoside, chamaedroside C – 3-O-β-D-glucopyranosyl(1→4)-β-D-glucopyranoside-(25S)-5β-spirostan-3β-ol, chamaedroside C1 – 3-O-βD-glucopyranosyl(1→4)-β-D-glucopyranoside-(25S)-spirost-5-en-3β-ol, chamaedroside C2 – 3-O-β-Dglucopyranosyl (1→4)-β-D-glucopyranoside-22,25-epoxy-(22S,25S)-furost-5-en-3β,26-diol and chamaedroside E – 3-O-β-D-glucopyranosyl(1→4)-β-D-glucopyranoside-(25S)-5β-furostan-3β,22α,26-triol-26-O-β-D-glucopyranoside. Chamaedrosides A, A1 and B are known steroidal glycosides identified in Veronica chamaedrys L. plants for the first time. Chamaedrosides A2, C, C1, C2 and E are new compounds and data about these compounds are absent in the literature.

Cuvinte-cheie
steroidal glycosides, Veronica chamaedrys L., NMR