New Acacetin Glycosides and Other Phenolics from Agastache foeniculum and Their Influence on Monoamine Oxidase A and B

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Abstract

Monoamine oxidase (MAO) inhibitors are effective therapeutic agents for the treatment of neurodegenerative diseases, and natural flavonoids found in Agastache species belong to them. In the present study, six new acylated flavone-O-glycosides were isolated from A. foeniculum and identified using UV, NMR spectroscopy and mass spectrometry as agastoside A (acacetin 7-O-(2′′-O-malonyl)-β-D-glucopyranoside), B (acacetin 7-O-(4′′-O-malonyl)-β-D-glucopyranoside), C (acacetin 7-O-(2′′,6′′-di-O-malonyl)-β-D-glucopyranoside), D (acacetin 7-O-(4′′,6′′-di-O-malonyl)-β-D-glucopyranoside), E (acacetin 7-O-(2′′-O-malonyl-6′′-O-acetyl)-β-D-glucopyranoside), and F (acacetin 7-O-(4′′-O-acetyl-6′′-O-malonyl)-β-D-glucopyranoside). Using flash chromatography and liquid chromatography-mass spectrometry, an additional 34 known phenolic compounds were detected. A study of biological activity showed that A. foeniculum flavonoids had an inhibitory effect on MAO-A and MAO-B, with the greatest effect noted for acacetin 7-O-glucoside acetate and malonate esters, which may be promising compounds for the development new drugs.

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D. N. Olennikov

Institute of General and Experimental Biology SB RAS

Author for correspondence.
Email: olennikovdn@mail.ru
Russian Federation, Ulan-Ude, 670047

N. I. Kashchenko

Institute of General and Experimental Biology SB RAS

Email: olennikovdn@mail.ru
Russian Federation, Ulan-Ude, 670047

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Supplementary files

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1. JATS XML
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2. 1. The structure of known flavonoids i–xiv isolated from A. foenicilum: Ac – acetyl, Mal – malonyl.

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3. 2. Mass spectra of compounds I (a), II (b) and III (c): Ac – acetyl, Mal – malonyl.

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4. 3. Structure of carbohydrate fragments of new acacetin glycosides I–VI. The arrows indicate the key correlations in the HMBC spectra.

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5. 4. Chromatogram (HPLC-DMD, λ = 330 nm) of the extract of A. foenicilum flowers and the absorption spectrum of acacetin glycosides (inset).The connection numbers are shown as in Table 4.

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