The Antioxidant Capability of Higenamine: Insights from Theory.

Nino Russo,Angela Parise,Tiziana Marino,Annia Galano,Isabella Romeo,Juan Raúl Alvarez-Idaboy

doi:10.3390/antiox9050358

Nino Russo, Angela Parise + Show 4 more

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https://doi.org/10.3390/antiox9050358

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Abstract

Density functional theory was employed to highlight the antioxidant working mechanism of higenamine in aqueous and lipid-like environments. Different reaction mechanisms were considered for the reaction of higenamine with the •OOH radical. The pH values and the molar fraction at physiological pH were determined in aqueous solution. The results show that the preferred reaction mechanism was the hydrogen atom transfer from the catecholic ring. The computed kinetic constants revealed that, in order to obtain reliable results, it is important to consider all the species present in water solution derived from acid–base equilibria. From the present investigation, it emerges that at physiological pH (7.4), the scavenging activity of higenamine against the •OOH radical is higher than that of Trolox, chosen as a reference antioxidant. Furthermore, higenamine results to be more efficient for that purpose than melatonin and caffeine, whose protective action against oxidative stress is frequently associated with their reactive oxygen species (ROS) scavenging activity.

Highlights

Higenamine [1-(40 -hydroxybenzyl)−6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline] (Figure 1), known as norcoclaurine or dl-demethylcoclaurine, is a plant-based alkaloid belonging to the structural class of protoberberines
3), our results indicated that the first deprotonation occurred at the OH in position C6
Figure 3), our results indicated that the first deprotonation occurred at the OH in position C6

Summary

Introduction

Higenamine [1-(40 -hydroxybenzyl)−6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline] (Figure 1), known as norcoclaurine or dl-demethylcoclaurine, is a plant-based alkaloid belonging to the structural class of protoberberines It is present in many plants such as Aconitum japonicum, Nandina. A protective effect on ischemia/reperfusion injuries (it activates the Phosphatidylinositol3-kinase–Protein kinase B known as Akt (PI3K/AKT) pathway) [5] and, more recently, it has been proposed as pharmacological stress agent for myocardial perfusion imaging. In addition to these properties, higenamine exhibits pharmacological activity towards other diseases, such as sepsis, heart failure, breathing difficulties, erectile dysfunction (ED), bradyarrhythmia, arthritis, and disseminated intravascular coagulation [1]. This multi-target activity led researchers to focus on the mechanisms and on the pathways implicated in higenamine action in different diseases

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