Issue 33, 2024, Issue in Progress

Computational assessment of the radical scavenging activity of cleomiscosin

Abstract

Coumarinolignans such as cleomiscosin A (CMA), cleomiscosin B (CMB), and cleomiscosin C (CMC) are secondary metabolites that were isolated from diverse plant species. Cleomiscosins (CMs) have numerous interesting biological activities, including noteworthy cytotoxicity of cancer cell lines along with hepatoprotective and assumed antioxidant activities. In this present study, the antioxidant properties of three cleomiscosins were investigated with a focus on the structure–activity relationship using thermodynamic and kinetic calculations with the M06-2X/6-311++G(d,p) method. The results show that CMs, including CMA, CMB, and CMC, are weak antioxidants in apolar environments, with koverall of 7.52 × 102 to 6.28 × 104 M−1 s−1 for the HOO˙ radical scavenging reaction in the gas phase and 3.47 × 102 to 6.44 × 104 M−1 s−1 in pentyl ethanoate. Remarkably, the difference in the fusion of phenylpropanoid structure with coumarin via two ortho-hydroxyl groups (CMA and CMB) does not cause any noticeable effect on their antioxidant activity, while the presence of a methoxy substitute on the aromatic ring of phenylpropanoid units (CMC) increases the reaction rate to about 61 to 84 times faster than that of CMA. In contrast, the studied CMs exhibit a good antioxidant capacity in polar environments, with a koverall range from 4.03 × 107 to 8.66 × 107 M−1 s−1, 102–103 times faster than that of Trolox, equal to that of ascorbic acid and resveratrol. The angular fusion of the phenylpropanoid and coumarin structures, as well as the methoxy substitution on the aromatic ring of the phenylpropanoid unit of the studied CMs, do not have any considerable effect on their antioxidant activity under the studied conditions.

Graphical abstract: Computational assessment of the radical scavenging activity of cleomiscosin

Supplementary files

Article information

Article type
Paper
Submitted
03 May 2024
Accepted
22 Jul 2024
First published
29 Jul 2024
This article is Open Access
Creative Commons BY license

RSC Adv., 2024,14, 23629-23637

Computational assessment of the radical scavenging activity of cleomiscosin

T. Q. Nguyen, A. Mechler and Q. V. Vo, RSC Adv., 2024, 14, 23629 DOI: 10.1039/D4RA03260H

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