Mechanistic and Kinetic Studies of the Radical Scavenging
Activity of 5‑O‑Methylnorbergenin:
Theoretical and Experimental Insights
Posted on 14.01.2022 - 21:30
5-O-Methylnorbergenin (5-OMB), a
natural compound isolated from Rourea harmandiana, is a compound with potential antioxidant activity based on its
chemical structure; however, this activity has not been investigated
thus far. In this study, the antioxidant activity of 5-OMB was evaluated by experimental and computational methods. 5-OMB exhibited high activity in DPPH (IC50 = 7.25 ± 0.94
μM) and ABTS•+ (IC50 = 4.23 ±
0.12 μM) assays, higher than the reference compound Trolox.
The computational results consistently show that 5-OMB is an excellent HOO• radical scavenger (koverall = 8.14 × 108 M–1 s–1) in water at physiological pH, however it
only exerts weak activity in lipid medium (koverall = 3.02 × 102 M–1 s–1). The reaction follows the formal hydrogen transfer
mechanism in nonpolar solvents, whereas both the sequential proton
loss electron transfer and the formal hydrogen transfer pathways contribute
to the activity in aqueous solution. There is a good agreement between
experimental and computational data, suggesting that 5-OMB is a promising natural radical scavenger in aqueous physiological
environment.
CITE THIS COLLECTION
Ngoc, Thuc Dinh; Le, Thanh Nguyen; Nguyen, Thi Van Anh; Mechler, Adam; Hoa, Nguyen Thi; Nam, Nguyen Linh; et al. (1753): Mechanistic and Kinetic Studies of the Radical Scavenging
Activity of 5‑O‑Methylnorbergenin:
Theoretical and Experimental Insights. ACS Publications. Collection. https://doi.org/10.1021/acs.jpcb.1c09196
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AUTHORS (7)
TN
Thuc Dinh Ngoc
TL
Thanh Nguyen Le
TN
Thi Van Anh Nguyen
AM
Adam Mechler
NH
Nguyen Thi Hoa
NN
Nguyen Linh Nam
QV
Quan V. Vo
KEYWORDS
radical scavenger (<lipid medium (<investigated thus far25 ± 023 ± 014 × 1002 × 10rourea harmandiana </sup >•</ supsup >•+</ supradical scavenging activityexhibited high activityexerts weak activity2 </ supreference compound troloxnatural compound isolatedaqueous physiological environmentoverall </ sub50 </ subomb </ b8 </ supk </physiological phaqueous solutionantioxidant activity>< subreaction followsnonpolar solventskinetic studiesgood agreementexcellent hoocomputational methodscomputational datachemical structure>‑ methylnorbergenin94 μm12 μm