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Planta Med 2022; 88(09/10): 826-837
DOI: 10.1055/a-1738-5648
Natural Product Chemistry and Analytical Studies
Original Papers

A Development Strategy of Tailor-made Natural Deep Eutectic Solvents for the Enhanced Extraction of Hydroxynaphthoquinones from Alkanna tinctoria Roots[ # ]

Elodie Bossard
Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, School of Health Sciences, National and Kapodistrian University of Athens, Athens, Greece
,
Nikolaos Tsafantakis
Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, School of Health Sciences, National and Kapodistrian University of Athens, Athens, Greece
,
Nektarios Aligiannis
Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, School of Health Sciences, National and Kapodistrian University of Athens, Athens, Greece
,
Nikolas Fokialakis 
Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, School of Health Sciences, National and Kapodistrian University of Athens, Athens, Greece
› Author AffiliationsSupported by: H2020 Marie Skłodowska-Curie Actions 721635
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Abstract

Natural hydroxynaphthoquinone enantiomers (HNQs) are well-described pharmaceutical and cosmeceutical agents especially present in the roots of Alkanna tinctoria (L.) Tausch, a species native to the Mediterranean region. In this work, eco-friendly natural deep eutectic solvents (NaDESs) were developed for the selective extraction of these compounds. An extensive screening was performed using more than sixty tailor-made NaDESs. The impact of the intrinsic physicochemical properties on the HNQs extraction efficiency as well as the specificity towards the different enantiomeric pairs was thoroughly investigated. As a result of a multivariate analysis and of the one factor-a-time solvent optimization, the eutectic mixture composed of levulinic acid and glucose (LeG) using a molar ratio of 5 : 1 (molHBA : molHBD) and 20% of water (w/w) was found as the most appropriate mixture for the highest extraction efficiency of HNQs. Further optimization of the extraction process was attained by response surface methodology, using a temperature of 45 °C, a solid-to-liquid ratio of 30 mg/mL, and an extraction time of 50 min. A maximum extraction output of 41.72 ± 1.04 mg/g was reached for HNQs, comparable to that of the commonly used organic solvents. A solid-phase extraction step was also proposed for the recovery of HNQs and for NaDESs recycling. Our results revealed NaDESs as a highly customizable class of green solvents with remarkable capabilities for the extraction of HNQs.

Key words

Natural Deep Eutectic Solvent (NaDES) - eco-friendly - Alkanna tinctoria - Boraginaceae - hydroxynaphthoquinone enantiomers

# Dedicated to Professor Dr. A. Douglas Kinghorn on the occasion of his 75th birthday.


Supporting Information

    1H-NMR and HRMS spectra of the seven isolated hydroxynaphthoquinone enantiomers: AS, AcAS, DeoxyAS, IsoBAS, DimetAAS, and IsoVAS-MetBAS (Figs 1S–12S), physicochemical properties of COaS based-, BOaS based-, POaS based-, OaS based-, and OaAG based-NaDESs (Tables 1S–5S), validation of the quantification method as linearity, specificity, limit of detection, limit of quantification, and intra- and inter-day precision (Tables 6S–9S), biplots of the principal component analysis of the extracts from A. tinctoria for COaS based-, BOaS based-, OaS based-, and OaAG based-NaDES categories separately (Fig. 14S), effect of molar ratio and water content on the amount of AS, AcAS, DeoxyAS, IsoBAS, DimetAAS, and IsoVAS-MetBAS extracted from A. tinctoria roots powder (Figs 15S and 16S), and BBD based statistical optimization results and response surface plots of the seven hydroxynaphthoquinone enantiomers (Tables 10S–11S and Fig. 17S) are available as Supporting information.

  • Supporting Information


Publication History

Received: 16 September 2021

Accepted after revision: 12 January 2022

Accepted Manuscript online:
12 January 2022

Article published online:
11 July 2022

© 2022. Thieme. All rights reserved.

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