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Molecules 2018, 23(4), 973; https://doi.org/10.3390/molecules23040973

Antioxidant and Cytoprotective Effects of Kukoamines A and B: Comparison and Positional Isomeric Effect

1,2,†,* , 3,4,†
,
1,2
,
1,2
and
3,4,*
1
School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2
Innovative Research & Development Laboratory of TCM, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
3
School of Basic Medical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
4
Research Center of Basic Integrative Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Susana M. Cardoso
Received: 26 March 2018 / Revised: 13 April 2018 / Accepted: 17 April 2018 / Published: 21 April 2018
(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products)
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Abstract

In this study, two natural phenolic polyamines, kukoamine A and B, were comparatively investigated for their antioxidant and cytoprotective effects in Fenton-damaged bone marrow-derived mesenchymal stem cells (bmMSCs). When compared with kukoamine B, kukoamine A consistently demonstrated higher IC50 values in PTIO•-scavenging (pH 7.4), Cu2+-reducing, DPPH•-scavenging, •O2-scavenging, and •OH-scavenging assays. However, in the PTIO•-scavenging assay, the IC50 values of each kukoamine varied with pH value. In the Fe2+-chelating assay, kukoamine B presented greater UV-Vis absorption and darker color than kukoamine A. In the HPLC–ESI–MS/MS analysis, kukoamine A with DPPH• produced radical-adduct-formation (RAF) peaks (m/z 922 and 713). The 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl (MTT) assay suggested that both kukoamines concentration-dependently increased the viabilities of Fenton-damaged bmMSCs at 56.5–188.4 μM. However, kukoamine A showed lower viability percentages than kukoamine B. In conclusion, the two isomers kukoamine A and B can protect bmMSCs from Fenton-induced damage, possibly through direct or indirect antioxidant pathways, including electron-transfer, proton-transfer, hydrogen atom transfer, RAF, and Fe2+-chelating. Since kukoamine B possesses higher potentials than kukoamine A in these pathways, kukoamine B is thus superior to kukoamine A in terms of cytoprotection. These differences can ultimately be attributed to positional isomeric effects. View Full-Text
Keywords: positional isomeric effect; antioxidant mechanisms; cytoprotective effect; kukoamine A; kukoamine B; phenolic polyamine positional isomeric effect; antioxidant mechanisms; cytoprotective effect; kukoamine A; kukoamine B; phenolic polyamine
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Li, X.; Lin, J.; Chen, B.; Xie, H.; Chen, D. Antioxidant and Cytoprotective Effects of Kukoamines A and B: Comparison and Positional Isomeric Effect. Molecules 2018, 23, 973.

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