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Int. J. Mol. Sci. 2017, 18(8), 1685; doi:10.3390/ijms18081685

Isorhamnetin and Quercetin Derivatives as Anti-Acetylcholinesterase Principles of Marigold (Calendula officinalis) Flowers and Preparations

1
Institute of General and Experimental Biology, Siberian Division, Russian Academy of Science, Sakh’yanovoy Street 6, Ulan-Ude 670047, Russia
2
Department of Biochemistry and Biotechnology, North-Eastern Federal University, 58 Belinsky Street, Yakutsk 677027, Russia
3
Pamir Biological Institute, Kholdorova Street 1, Khorog 736002, Tajikistan
4
All-Russian Institute of Medical and Aromatic Plants, Greena Street 7/1, Moscow 117216, Russia
5
Regulatory and Medical Scientific Affairs, Padma AG, 1 Underfeldstrasse, CH-8340 Hinwil, Switzerland
*
Author to whom correspondence should be addressed.
Received: 19 June 2017 / Revised: 25 July 2017 / Accepted: 1 August 2017 / Published: 2 August 2017
(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2018)
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Abstract

Marigold (Calendula officinalis L.) is one of the most common and widespread plants used medicinally all over the world. The present study aimed to evaluate the anti-acetylcholinesterase activity of marigold flowers, detect the compounds responsible and perform chemical analysis of marigold commercial products. Analysis of 23 varieties of C. officinalis flowers introduced into Siberia allowed us to select the Greenheart Orange variety due to the superior content of flavonoids (46.87 mg/g) and the highest inhibitory activity against acetylcholinesterase (IC50 63.52 µg/mL). Flavonoids, isorhamnetin and quercetin derivatives were revealed as potential inhibitors with the application of high-performance liquid chromatography (HPLC) activity-based profiling. Investigation of the inhibitory activity of isorhamnetin glycosides demonstrated the maximal potency for isorhamnetin-3-О-(2′′,6′′-di-acetyl)-glucoside (IC50 51.26 μM) and minimal potency for typhaneoside (isorhamnetin-3-O-(2′′,6′′-di-rhamnosyl)-glucoside; IC50 94.92 µM). Among quercetin derivatives, the most active compound was quercetin-3-О-(2′′,6′′-di-acetyl)-glucoside (IC50 36.47 µM), and the least active component was manghaslin (quercetin-3-O-(2′′,6′′-di-rhamnosyl)-glucoside; IC50 94.92 µM). Some structure-activity relationships were discussed. Analysis of commercial marigold formulations revealed a reduced flavonoid content (from 7.18–19.85 mg/g) compared with introduced varieties. Liquid extract was the most enriched preparation, characterized by 3.10 mg/mL of total flavonoid content, and infusion was the least enriched formulation (0.41 mg/mL). The presented results suggest that isorhamnetin and quercetin and its glycosides can be considered as potential anti-acetylcholinesterase agents. View Full-Text
Keywords: Calendula officinalis; marigold; acetylcholinesterase inhibition; quercetin; isorhamnetin; HPLC Calendula officinalis; marigold; acetylcholinesterase inhibition; quercetin; isorhamnetin; HPLC
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MDPI and ACS Style

Olennikov, D.N.; Kashchenko, N.I.; Chirikova, N.K.; Akobirshoeva, A.; Zilfikarov, I.N.; Vennos, C. Isorhamnetin and Quercetin Derivatives as Anti-Acetylcholinesterase Principles of Marigold (Calendula officinalis) Flowers and Preparations. Int. J. Mol. Sci. 2017, 18, 1685.

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