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Open AccessArticle

Extraction of Anthraquinones from Japanese Knotweed Rhizomes and Their Analyses by High Performance Thin-Layer Chromatography and Mass Spectrometry

Department of Food Chemistry, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia
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Author to whom correspondence should be addressed.
Plants 2020, 9(12), 1753; https://doi.org/10.3390/plants9121753
Received: 25 November 2020 / Revised: 1 December 2020 / Accepted: 9 December 2020 / Published: 11 December 2020
(This article belongs to the Special Issue Structural and Functional Analysis of Extracts in Plants)
Anthraquinones (yellow dyes) were extracted from Japanese knotweed rhizomes with twelve extraction solvents (water; ethanol(aq) (20%, 40%, 60%, 70% and 80%), ethanol, 70% methanol(aq), methanol, 70% acetone(aq), acetone and dichloromethane). The obtained sample test solutions (STSs) were analyzed using high-performance thin-layer chromatography (HPTLC) coupled to densitometry and mass spectrometry (HPTLC–MS/MS) on HPTLC silica gel plates. Identical qualitative densitometric profiles (with anthraquinone aglycones and glycosylated anthraquinones) were obtained for STSs in all the solvents except for the STS in dichloromethane, which enabled the most selective extractions of anthraquinone aglycones emodin and physcion. The highest extraction efficiency, evaluated by comparison of the total peak areas in the densitograms of all STSs scanned at 442 nm, was achieved for 70% acetone(aq). In STS prepared with 70% acetone(aq), the separation of non-glycosylated and glycosylated anthraquinones was achieved with developing solvents toluene–acetone–formic acid (6:6:1, 3:6:1 and 3:3:1 v/v) and dichloromethane–acetone–formic acid (1:1:0.1, v/v). Non-glycosylated anthraquinones were separated only with toluene–acetone–formic acid, among which the best resolution between emodin and physcion gave the ratio 6:6:1 (v/v). This solvent and dichloromethane–acetone–formic acid (1:1:0.1, v/v) enabled the best separation of glycosylated anthraquinones. Four HPTLC-MS/MS methods enabled the identification of emodin and tentative identification of its three glycosylated analogs (emodin-8-O-hexoside, emodin-O-acetyl-hexoside and emodin-O-malonyl-hexoside), while only the HPTLC-MS/MS method with toluene-acetone-formic acid (6:6:1, v/v) enabled the identification of physcion. Changes of the shapes and the absorption maxima (bathochromic shifts) in the absorption spectra after post-chromatographic derivatization provided additional proof for the detection of physcion and rejection of the presence of chrysophanol in STS. View Full-Text
Keywords: Japanese knotweed; Reynoutria; Polygonum; Polygonaceae; anthraquinones; emodin; physcion; HPTLC; HPTLC-MS; densitometry Japanese knotweed; Reynoutria; Polygonum; Polygonaceae; anthraquinones; emodin; physcion; HPTLC; HPTLC-MS; densitometry
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MDPI and ACS Style

Glavnik, V.; Vovk, I. Extraction of Anthraquinones from Japanese Knotweed Rhizomes and Their Analyses by High Performance Thin-Layer Chromatography and Mass Spectrometry. Plants 2020, 9, 1753. https://doi.org/10.3390/plants9121753

AMA Style

Glavnik V, Vovk I. Extraction of Anthraquinones from Japanese Knotweed Rhizomes and Their Analyses by High Performance Thin-Layer Chromatography and Mass Spectrometry. Plants. 2020; 9(12):1753. https://doi.org/10.3390/plants9121753

Chicago/Turabian Style

Glavnik, Vesna; Vovk, Irena. 2020. "Extraction of Anthraquinones from Japanese Knotweed Rhizomes and Their Analyses by High Performance Thin-Layer Chromatography and Mass Spectrometry" Plants 9, no. 12: 1753. https://doi.org/10.3390/plants9121753

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