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. 2018 Apr 2;23(4):816.
doi: 10.3390/molecules23040816.

Antioxidant Activities of Phenolic Metabolites from Flemingia philippinensis Merr. et Rolfe and Their Application to DNA Damage Protection

Jeong Yoon Kim  1 , Yan Wang  2 , Yeong Hun Song  3 , Zia Uddin  4 , Zuo Peng Li  5 , Yeong Jun Ban  6 , Ki Hun Park  7
Affiliations

Antioxidant Activities of Phenolic Metabolites from Flemingia philippinensis Merr. et Rolfe and Their Application to DNA Damage Protection

Jeong Yoon Kim et al. Molecules. .

Abstract

F. philippinensis Merr. et Rolfe has been cultivated on a large scale and is widely consumed by local inhabitants as an important nutraceutical, especially against rheumatism which has a deep connection with antioxidants. In this study, a total of 18 different phenolic metabolite compounds in F. philippinensis were isolated and identified, and evaluated for their antioxidant and DNA damage protection potential. The antioxidant activity of the 18 identified compounds was screened using DPPH, ORAC, hydroxyl and superoxide radical scavenging assays. The antioxidant potential of the compounds was found to differ by functionality and skeleton. However, most compounds showed a good antioxidant potential. In particular, seven of the identified compounds, namely, compounds 2, 3, 6, 10, 11, 15 and 16, showed significant protective effects on pBR322 plasmid DNA against the mutagenic and toxic effects of Fenton's reaction. The most active compound, compound 2, displayed a dose-dependent DNA damage protection potential in the range of 7.5~60.0 μM. The DNA damage protective effect of the identified compounds was significantly correlated with the hydroxyl radical scavenging activity. Compounds that exhibited effective (IC50 = 5.4~12.5 μg/mL) hydroxyl radical scavenging activity were found to be the ones with higher DNA damage protection potential.

Keywords: DNA damage protective effects; Flemingia philippinensis; electron spin resonance spectroscopy; phenolic metabolites; radical scavenging activity.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of phenolic metabolites (1–18) from F. philippinensis.
Figure 2
Figure 2
DPPH radical scavenging activity of compounds 1–18 and Trolox.
Figure 3
Figure 3
(a) Correlation between ORAC values and superoxide radical scavenging activity; (b) correlation between hydroxyl radical scavenging activity and DNA strand damage.
Figure 4
Figure 4
(a) Hydroxyl radical scavenging activity of the identified compounds 1–18 and trolox; (b) ESR spectra of hydroxyl radical according to dose of compound 2 (0, 6.0, 12.0 and 24.0 μg/mL); inset (I): chemical structure of 2 showing the most active hydroxyl radical scavenging effect; inset (II): plot of ESR signal ratio versus concentration of 2.
Figure 5
Figure 5
Protective effect of metabolites (1–9) against pBR322 DNA cleavage induced by hydroxyl radical oxidative injury. Lane 1: pBR322 plasmid DNA control; lane 2: pBR322 DNA + 1 mM FeSO4 + 30% H2O2; lane 3: compound 1, 60 μM; lane 4: compound 2, 60 μM; lane 5: compound 3, 60 μM; lane 6: compound 4, 60 μM; lane 7: compound 5, 60 μM; compound 6, 60 μM; lane 9: compound 7, 60 μM; lane 10: compound 8, 60 μM; lane 11: compound 9, 60 μM; lane 12: Trolox (positive control), 60 μM.
Figure 6
Figure 6
Protective effects of metabolites (10–18) against pBR322 DNA cleavage induced by hydroxyl radical oxidative injury. Lane 1: pBR322 plasmid DNA control; lane 2: pBR322 DNA + 1 mM FeSO4 + 30% H2O2; lane 3: compound 10, 60 μM; lane 4: compound 11, 60 μM; lane 5: compound 12, 60 μM; lane 6: compound 13, 60 μM; lane 7: compound 14, 60 μM; lane 8: compound 15, 60 μM; lane 9: compound 16, 60 μM; lane 10: compound 17, 60 μM; lane 11: compound 18, 60 μM; lane 12: Trolox (positive control), 60 μM.
Figure 7
Figure 7
Dose-dependent protective effect of auriculasin (2) against pBR322 DNA cleavage induced by hydroxyl radical oxidative injury. Lane 1: pBR322 plasmid DNA control; lane 2: pBR322 DNA + 1 mM FeSO4 + 30% H2O2; lane 3: compound 2, 7.5 μM; lane 4: compound 2, 15 μM; lane 5: compound 2, 30 μM; lane 6: compound 2, 60 μM.
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