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Nat Prod Res. 2017 Dec 29:1-9. doi: 10.1080/14786419.2017.1419229. [Epub ahead of print]

1,2,4-trihydroxynaphthalene-2-O-β-D-glucopyranoside: A new powerful antioxidant and inhibitor of Aβ42 aggregation isolated from the leaves of Lawsonia inermis.

Author information

1
a Faculté des Sciences de Tunis , Université de Tunis El Manar , Tunis , Tunisia.
2
b Laboratoire des Plantes Aromatiques et Médicinales (LPAM- LR15CBBC06), Centre de Biotechnologie de Borj-Cédria , Hammam-Lif , Tunisia.
3
c Laboratoire de Chimie des Substances Naturelles et de Synthèse Organique (99/UR/12-26), Faculté des Sciences de Monastir , Université de Monastir , Monastir , Tunisia.
4
d Laboratoire de chimie , Institut supérieur agronomique de Chott Meriem , Sousse , Tunisia.
5
e Department of Biomedical, Experimental and Clinical Sciences 'Mario Serio' , University of Florence , Florence , Italy.
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f Department of Neuroscience, Psychology, Drug Research and Child Health , University of Florence , Florence , Italy.
7
g Institut de Chimie des Milieux et Matériaux de Poitiers, IC2MP, UMR CNRS 7285 , Poitiers Cedex 9 , France.

Abstract

Mounting evidence indicates free radicals as toxic species causing damage to human cells leading to the pathogenesis of many diseases such as neurodegenerative disease. Plant derived antioxidants are considered as promising strategy to prevent free radical toxicity. In this study, the crude extract (CE), 50%MeOH, Petroleum Ether (PE) and Ethyl acetate (EA) fractions of Lawsonia inermis leaves were investigated for their antioxidant activity and their ability to counteract amyloid-β42 (Aβ42) aggregation. Elution of the most bioactive fraction (EA) on silica gel column chromatography led to six sub-fractions. The most active sub-fraction (1) was further resolved on silica gel column chromatography. A new compound with powerful antioxidant and anti-Aβ42 aggregation properties was purified and characterised by spectroscopic methods as 1,2,4-trihydroxynaphthalene-2-O-β-D-glucopyranoside (THNG). This finding suggests that the antioxidant and anti-Aβ42 aggregation activities of L. inermis leaves are strongly correlated to this compound.

KEYWORDS:

50% MeOH, 50% methanolic fraction; AD, Alzheimer disease; CE, Crude extract; Alzheimer disease; Antioxidant; Aβ42 aggregation; Aβ42, Amyloid-β42; DPPH, 2,2- diphenyl-1-picrylhydrazyl; EA, Ethyl acetate fraction; EC50, effective concentration at which the absorbance was 0.5; HFIP, hexafluoroisopropanol; IC50, Inhibition Concentration at 50%; Lawsonia inermis; PE, Petroleum ether fraction; ROS, Reactive oxygen species; THNG, 1, 2, 4-trihydroxynaphthalene-2-O-β-D-glucopyranoside; ThT, Thioflavine T; Res, Resveratrol; bioguided fractionation; phenolic glycoside

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