Theoretical study of fast repair of DNA damage by cistanoside C and analogs: Mechanism and docking

Abstract

Experiments show that the natural substances phenylpropanoid glycosides (PPGs) extracted from pelicularis spicata are capable of repairing DNA damaged by oxygen radicals. Based on kinetic measurements and experiments on tumor cells, a theoretical study of the interaction between PPG molecules and isolated DNA bases, as well as a DNA fragment has been performed. An interaction mechanism reported early has been refined. The docking calculations performed using junction minimization of nucleic acids (JUMNA) software showed that the PPG molecules can be docked into the minor groove of DNA and form complexes with the geometry suitable for an electron transfer between guanine radical and the ligand. Such complexes can be formed without major distortions of DNA structure and are further stabilized by the interaction with the rhamnosyl side-groups.

Ultraviolet B induced bioactive changes of enzymatic and non-enzymatic antioxidants and lipids in Trigonella foenum-graecum L. (Fenugreek)

“…Hence, the phenolics considered as idyllic for maintaining the cellular redox level during photooxidative stress. Studies also showed that phenolics quickly repair DNA damage during the attack of free radical anions through electron transfer reaction (36). Flavonoids such as anthocyanin are the class of phenolics that enabled photo-oxidative stress tolerance in plants (37).…”

In vivo non‐enzymatic repair of DNA oxidative damage by polyphenols

“…The rapid electron transfer reaction between the thymidine anion and caffeic acid has been reported by Zou et al (1995). Our previous studies (Li et al, 1997;Shi et al, 1999aShi et al, ,b, 2000Zhao et al, 2001Zhao et al, , 2003Gao et al, 2003;Sperandio et al, 2002) in chemical system also showed that many natural polyphenols can undergo electron transfer to ROSdamaged sites on DNA, finally repairing them and thereby eliminating the amount of both base damage and strand breaks. This mechanism for the reduction of DNA dysfunction arising from ROS attack could be significant at all different constituent levels of damaged DNA (Shi et al, 2008), from deoxynucleoside, deoxynucleotide, polydeoxynucleotide, single-stranded DNA, double-stranded DNA, to the integral DNA, which is more similar to cellular status.…”

Comparative Study of Activities between Verbascoside and Rutin by Docking Method

“…We carried out two series of docking studies using one of the PPGs, Cistanoside C with two DNA fragments respectively, decamer ATGACGTCAT [23] and telomere (TTAGGG) n [24]. The following conclusions have been drawn from our studies: 1.…”

“…In our preceding works [23,24], we have studied a proposed mechanism of interaction between PPG molecules and DNA fragments from both experimental and theoretical view points. We carried out two series of docking studies using one of the PPGs, Cistanoside C with two DNA fragments respectively, decamer ATGACGTCAT [23] and telomere (TTAGGG) n [24].…”

“…We have reported that the repair mechanism of damaged DNA by PPG molecules is believed through an electron transfer process by the formation of drug-receptor complex in minor groove of the double helix [23,24,45]. The exocyclic nitrogen atom (N2) of guanine in DNA double helix and one of phenolic groups of PPG are involved in electron transfer process.…”