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Planta Med 2018; 84(09/10): 710-715
DOI: 10.1055/s-0044-100187
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Phenylethanoid Glycosides from Cistanche phelypaea and Their Activity as Inhibitors of Monoacylglycerol Lipase (MAGL)

Khadidja Aya Beladjila
1   Laboratoire dʼObtention des Substances Thérapeutiques (LOST), Département de Chimie, Université des Frères Mentouri-Constantine, Constantine, Algeria
,
Djemaa Berrehal
1   Laboratoire dʼObtention des Substances Thérapeutiques (LOST), Département de Chimie, Université des Frères Mentouri-Constantine, Constantine, Algeria
,
Nunziatina De Tommasi
2   Dipartimento di Farmacia, Università di Salerno, Fisciano, Italy
,
Carlotta Granchi
3   Dipartimento di Farmacia, Università di Pisa, Italy
,
Giulia Bononi
3   Dipartimento di Farmacia, Università di Pisa, Italy
,
Alessandra Braca
3   Dipartimento di Farmacia, Università di Pisa, Italy
4   Centro Interdipartimentale di Ricerca "Nutraceutica e Alimentazione per la Salute”, Università di Pisa, Italy
,
Marinella De Leo
3   Dipartimento di Farmacia, Università di Pisa, Italy
4   Centro Interdipartimentale di Ricerca "Nutraceutica e Alimentazione per la Salute”, Università di Pisa, Italy
› Author Affiliations
Further Information

Publication History

received 30 October 2017
revised 21 December 2017

accepted 27 December 2017

Publication Date:
10 January 2018 (online)

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Abstract

Four new phenylethanoid glycosides (1–4), 1-β-p-hydroxyphenyl-ethyl-2-O-acetyl-3,6-di-α-l-rhamnopyranosyl-β-d-glucopyranoside (1), 1-β-p-hydroxyphenyl-ethyl-3,6-O-di-α-l-rhamnopyranosyl-β-d-glucopyranoside (2), 1-β-p-hydroxyphenyl-ethyl-2-O-acetyl-3,6-di-α-l-rhamnopyranosyl-4-p-coumaroyl-β-d-glucopyranoside (3), and 1-β-p-hydroxyphenyl-ethyl-3,6-di-α-l-rhamnopyranosyl-4-p-coumaroyl-β-d-glucopyranoside (4), together with three known compounds, were isolated from the n-butanol extract of Cistanche phelypaea aerial parts. The structural characterization of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The isolated compounds were assayed for their inhibitory activity on two enzymes involved in the peculiar glycolytic or lipidic metabolism of cancer cells, human lactate dehydrogenase (LDH), and monoacylglycerol lipase (MAGL), respectively. All the compounds showed negligible activity on LDH, whereas some of them displayed a certain inhibition activity on MAGL. In particular, compound 1 was the most active on MAGL, showing an IC50 value of 88.0 µM, and modeling studies rationalized the supposed binding mode of 1 in the MAGL active site.

Key words

Cistanche phelypaea - Orobanchaceae - phenylethanoid glycosides - cancer - monoacylglycerol lipase - lactate dehydrogenase

Supporting Information

    HRESIMS and NMR spectra of compounds 1–4 and data for the IC50 determination of compound 1 in MAGL enzymatic assays are available as Supporting Information.

  • Supporting Information
 

  • References

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