Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle

Abstract

Methanolic extract from lyophilized roots of Impatiens glandulifera Royle was analyzed by high performance liquid chromatography using DAD and FLD detection and this revealed one dominant highly fluorescent very unstable substance. The stability of this derivative is strongly dependent on the plant material drying procedure and extraction procedure used. The structure of the substance was established as 1,2,4-trihydroxynaphthalene-1-O-glucoside (THNG) according LC-MS and NMR measurements. When lyophilized plant material was extracted with methanol an almost four times higher amount of THNG was found in the extract, compared to the amount of 2-hydroxy-1,4-naphthoquinone obtained, while in the case of the same lyophilized plant material extracted with water there was no THNG in the extract. The main compounds in this case was 2-hydroxy-1,4-naphthoquinone. In the plant material dried at the laboratory temperature and extracted by methanol there are only traces of THNG.

Biosynthesis and molecular actions of specialized 1,4-naphthoquinone natural products produced by horticultural plants

“…Lawsone is also found in the flowering aerial parts and roots of several Impatiens species. 81–83 Similar to juglone, lawsone is a simple hydroxylated 1,4-NQ, though its biosynthesis is quite different. This idea first emerged after feeding studies with I. balsamina showed that labeled shikimate incorporated into juglone and lawsone in different patterns.…”

“…Lawsone is also precursor to other 1,4-NQ natural products. An allelopathic methylated lawsone derivative, 2-methoxy-1,4-NQ (2-MNQ; Figure 2 ), is found in many tissues of several Impatiens species, 81 , 83–85 and is almost certainly formed via an S -adenosylmethionine-dependent O -methyltransferase. 86 In several native Central and South American trees, including the Pau d’arco tree (Red Lapacho; Tabebuia impetiginosa , syn.…”

Varietal Distributions of Stilbenes in Grape Cane of Vitis vinifera L.

“…Two detectors were used for analysing: a diode array detector G1315B (DAD, Agilent, Prague, the Czech Republic) with the detection of wavelengths at 220 and 315 nm and a scanning range of 190-600 nm, and a fluorescence detector G1321A (FLD, Agilent, Prague, the Czech Republic) with excitation wavelength of 315 nm, emission wavelength of 395 nm, and scanning of emission in the 300-600 nm range. Finally, the method of quantification was validated in terms of linearity, limits of detection, and repeatability (Tříska et al, 2012(Tříska et al, , 2013. Identifications of stilbenes (trans-resveratrol, transe-viniferin and r2-viniferin) were done previously by HRMS (High Resolution Mass Spectrometr) and H-NMR (Nuclear Magnetic Resonance) as presented by Soural et al (2015).…”

Lipophilic components and evaluation of the cytotoxic and antioxidant activities of <em>Impatiens glandulifera</em> Royle and <em>Impatiens noli – tangere</em> L. (Balsaminaceae)

“…Impatiens glandulifera Royle and Impatiens nolitangere L. are an annual herbaceous species which belongs to the Balsaminaceae family. These plants are native to North-Western, Central Europe and Asia (Tříska et al, 2013). In Poland, I. noli-tangere and I. glandulifera are two of the top 25 invasive alien plants (Tokarska-Guzik et al, 2010).…”

“…From a chemical point of view, I. glandulifera and I. noli-tangere have been the subject of few studies which have reported on the isolation or identification of flavonoids (Szewczyk et al, 2016a), phenolic acids (Szewczyk and Olech, 2017), essential oils (Szewczyk et al, 2016b), triterpenoid saponins (Grabowska et al, 2017), glucosylated steroids (Cimmino et al, 2016), and naphthoquinones (Lobstein et al, 2001;Tříska et al, 2013).…”