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.
Highlights
The majority of natural antioxidants are phenolic compounds, mainly including flavonoids, phenolic acids, tannins, coumarins, and anthraquinone [1,2], while none of these contain a nitrogen atom (N-atom) in their molecular scaffolds
As phenolic alkaloids naturally present in the dried root bark of Lycium chinense, kukoamines A (KukA) and B (KukB) (Figure 1) possess nitrogen
It has been reported that oxidative damage lowers the viability of bone marrow-derived mesenchymal stem cells (bmMSCs) and limits their
Summary
The majority of natural antioxidants are phenolic compounds, mainly including flavonoids, phenolic acids, tannins, coumarins, and anthraquinone [1,2], while none of these contain a nitrogen atom (N-atom) in their molecular scaffolds. As phenolic alkaloids naturally present in the dried root bark of Lycium chinense, kukoamines A (KukA) and B (KukB) (Figure 1) possess nitrogen. Kukoamines A (KukA) and B (KukB) (Figure 1) possess nitrogen atoms in atoms in their molecular structures, are derivatives with dihydrocaffeoyl their molecular structures, and theyand are they sperminespermine derivatives with dihydrocaffeoyl groups groups [3,4]. It is well known that dihydrocaffeic acid and their analogs are potent natural antioxidants [3,4]. It is well known that dihydrocaffeic acid and their analogs are potent natural antioxidants with with multiple mechanisms involving radical scavenging metal chelation. Spermine multiple mechanisms involving freefree radical scavenging andand metal ionion chelation [5].[5]. Spermine is ais anatural naturalantioxidant, antioxidant,which whichplays playsan animportant importantrole rolein inmany manycellular cellularprocesses processesincluding includingprotection protection ofofcells damage byby free radicals, andand regulation of transcription and and translation [5,6]
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