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Isolation of Myricitrin and 3,5-di-O-Methyl Gossypetin from Syzygium samarangense and Evaluation of their Involvement in Protecting Keratinocytes against Oxidative Stress via Activation of the Nrf-2 Pathway

1
Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, 69120 Heidelberg, Germany
2
AgroBioSciences Research Division, Mohammed VI Polytechnic University, Lot 660–Hay Moulay Rachid, Ben-Guerir 43150, Morocco
3
Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte Sant’Angelo, via Cinthia 4, 80126 Naples, Italy
4
Department of Pharmacognosy, Faculty of Pharmacy, October 6 University, Giza 12585, Egypt
5
Department of Phytochemistry and Plant Systematics, National Research Center, Dokki, Cairo 12622, Egypt
*
Authors to whom correspondence should be addressed.
The authors contributed equally to this work.
Molecules 2019, 24(9), 1839; https://doi.org/10.3390/molecules24091839 (registering DOI)
Received: 23 April 2019 / Revised: 8 May 2019 / Accepted: 10 May 2019 / Published: 13 May 2019
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Abstract

The wax apple (Syzygium samarangense) is traditionally employed as an antibacterial and immunostimulant drug in traditional medicine. This plant is rich in different flavonoids and tannins. In this study, we isolated two compounds from S. samarangense leaves: myricitrin and 3,5-di-O-methyl gossypetin. Then, we investigated the mechanisms of action of the two compounds against oxidative stress (induced by sodium arsenite) and inflammation (induced by UV light) on human keratinocytes. We could clearly demonstrate that the pre-treatment of cells with both compounds was able to mitigate the negative effects induced by oxidative stress, as no alteration in reactive oxygen species (ROS) production, glutathione (GSH) level, or protein oxidation was observed. Additionally, both compounds were able to modulate mitogen-activated protein kinase (MAPK) signaling pathways to counteract oxidative stress activation. Finally, we showed that 3,5-di-O-methyl gossypetin exerted its antioxidant activity through the nuclear transcription factor-2 (Nrf-2) pathway, stimulating the expression of antioxidant proteins, such as HO-1 and Mn-SOD-3. View Full-Text
Keywords: Syzygium samarangense; antioxidants; myricitrin; 3,5-di-O-methyl gossypetin; eukaryotic cells; sodium arsenite Syzygium samarangense; antioxidants; myricitrin; 3,5-di-O-methyl gossypetin; eukaryotic cells; sodium arsenite
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Sobeh, M.; Petruk, G.; Osman, S.; El Raey, M.A.; Imbimbo, P.; Monti, D.M.; Wink, M. Isolation of Myricitrin and 3,5-di-O-Methyl Gossypetin from Syzygium samarangense and Evaluation of their Involvement in Protecting Keratinocytes against Oxidative Stress via Activation of the Nrf-2 Pathway. Molecules 2019, 24, 1839.

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