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Molecules 2015, 20(5), 7454-7473; doi:10.3390/molecules20057454

Flavonoids from Sideritis Species: Human Monoamine Oxidase (hMAO) Inhibitory Activities, Molecular Docking Studies and Crystal Structure of Xanthomicrol

1
Department of Pharmaceutical Botany, Faculty of Pharmacy, Hacettepe University, Ankara 06100, Turkey
2
Department of Biochemistry, Faculty of Pharmacy, Hacettepe University, Ankara 06100, Turkey
3
Department of Bioinformatics and Genetics, Faculty of Engineering and Natural Sciences, Cibali Campus, Kadir Has University, Fatih, Istanbul 34083, Turkey
4
Science and Technology Application and Research Center, Faculty of Pharmacy, Dicle University, Diyarbakir 21280, Turkey
5
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Dicle University, Diyarbakir 21280, Turkey
6
Department of Pharmacognosy, Faculty of Pharmacy, Near East University, Lefkoşa, Mersin-10, Turkey
*
Author to whom correspondence should be addressed.
Academic Editor: Peter Koulen
Received: 16 March 2015 / Revised: 9 April 2015 / Accepted: 15 April 2015 / Published: 23 April 2015
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Abstract

The inhibitory effects of flavonoids on monoamine oxidases (MAOs) have attracted great interest since alterations in monoaminergic transmission are reported to be related to neurodegenerative diseases such as Parkinson’s and Alzheimer’s diseases and psychiatric disorders such as depression and anxiety, thus MAOs may be considered as targets for the treatment of these multi-factorial diseases. In the present study, four Sideritis flavonoids, xanthomicrol (1), isoscutellarein 7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (2), isoscutellarein 7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (3) and salvigenin (4) were docked computationally into the active site of the human monoamine oxidase isoforms (hMAO-A and hMAO-B) and were also investigated for their hMAO inhibitory potencies using recombinant hMAO isoenzymes. The flavonoids inhibited hMAO-A selectively and reversibly in a competitive mode. Salvigenin (4) was found to be the most potent hMAO-A inhibitor, while xanthomicrol (1) appeared as the most selective hMAO-A inhibitor. The computationally obtained results were in good agreement with the corresponding experimental values. In addition, the x-ray structure of xanthomicrol (1) has been shown. The current work warrants further preclinical studies to assess the potential of xanthomicrol (1) and salvigenin (4) as new selective and reversible hMAO-A inhibitors for the treatment of depression and anxiety. View Full-Text
Keywords: Sideritis; flavonoid; xanthomicrol; salvigenin; monoamine oxidase; inhibition; molecular docking; X-ray diffraction investigation Sideritis; flavonoid; xanthomicrol; salvigenin; monoamine oxidase; inhibition; molecular docking; X-ray diffraction investigation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Turkmenoglu, F.P.; Baysal, İ.; Ciftci-Yabanoglu, S.; Yelekci, K.; Temel, H.; Paşa, S.; Ezer, N.; Çalış, İ.; Ucar, G. Flavonoids from Sideritis Species: Human Monoamine Oxidase (hMAO) Inhibitory Activities, Molecular Docking Studies and Crystal Structure of Xanthomicrol. Molecules 2015, 20, 7454-7473.

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