Elucidation of reactive oxygen species scavenging pathways of norbergenin utilizing DFT approaches

Kautsar Ul Haq; Rahmanto Aryabraga Rusdipoetra; Imam Siswanto; Hery Suwito

doi:10.1098/rsos.221349

Elucidation of reactive oxygen species scavenging pathways of norbergenin utilizing DFT approaches

R Soc Open Sci. 2022 Dec 21;9(12):221349. doi: 10.1098/rsos.221349. eCollection 2022 Dec.

Authors

Kautsar Ul Haq^{1

2}, Rahmanto Aryabraga Rusdipoetra², Imam Siswanto^{1

2}, Hery Suwito²

Affiliations

¹ Bioinformatics Division, University CoE-Research Center for Bio-Molecule Engineering, Universitas Airlangga, Surabaya 60115, Indonesia.
² Department of Chemistry, Faculty of Science and Technology, Universitas Airlangga, Indonesia.

Abstract

Bergenin is a polyphenolic compound that contains isocoumarin skeletal derived from C-glycosylated 4-O-methylgallic acid. The biological activities of this compound and its derivatives are quite diverse. Recent studies reveal neuroprotective effects in vitro and in vivo in Alzheimer's. Norbergenin is a demethylated form of bergenin, known for better antioxidant capacity and associated with neuroprotective properties through oxidative stress inhibition. This study focused on investigating the scavenging mechanism of norbergenin with the ^•OH, ^•OOH, and $O_{2}^{∙ -}$ as a radical model under physiological and lipid environments. The thermodynamic and kinetic parameters of the hydrogen transfer (HT), single electron transfer (SET), sequential proton lost-electron transfer (SPLET) and radical adduct formation (RAF) mechanisms were determined theoretically by the density functional theory (DFT) at M06-2X/6-311 + + G(d,p) level of theory. Based on the computational results, this compound has proved as an excellent ^•OOH and ^•OH scavenger under physiological conditions better than Trolox and vitamin C, whereas its radical demonstrated as an efficient $O_{2}^{∙ -}$ scavenger.

Keywords: Alzheimer's; antioxidant; density functional theory; kinetic; norbergenin; scavenging mechanism.

Associated data

figshare/10.6084/m9.figshare.c.6350059