Phenolic constituents of the aerial parts of Impatiens glandulifera Royle (Balsaminaceae) and their antioxidant activities

Article abstract of DOI:10.1080/14786419.2018.1499644

As a continuation of investigating Impatiens L. genus, eight flavonoids, eriodyctiol, eriodyctiol 7-O-β-?-glucoside, kaempferol 3-O-β-?-glucoside, kaempferol 3-O-β-?-galactoside, kaempferol 3-rhamnosyl-di-glucoside, kaempferol 3-O-β-?-rutinoside, quercetin 3-O-β-?-glucoside and quercetin 3-O-β-?-galactoside, two phenolic acids–p-hydroxybenzoic acid and protocatechuic acid, and 2-methoxynaphthalene-1,4-dione were isolated from the aerial parts of I. glandulifera collected in Poland. The structures of the compounds were established by analysis of their spectroscopic (¹H and ¹³C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. Quercetin 3-O-β-?-glucoside, kaempferol 3-O-β-?-galactoside and kaempferol 3-O-β-?-rutinoside were isolated for the first time from the investigated taxon. In addition, the antioxidant activities in different tests of all obtained compounds were evaluated. The results clearly showed that among analyzed constituents, quercetin 3-O-β-?-glucoside exhibited antioxidant activity comparable or better than ascorbic acid and Trolox which were used as a positive control.

Full text of DOI:10.1080/14786419.2018.1499644

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Phenolic constituents of the aerial parts of
Impatiens glandulifera Royle (Balsaminaceae) and
their antioxidant activities
Katarzyna Szewczyk, Serhat Sezai Cicek, Christian Zidorn & Sebastian
Granica
To cite this article: Katarzyna Szewczyk, Serhat Sezai Cicek, Christian Zidorn & Sebastian
Granica (2018): Phenolic constituents of the aerial parts of Impatiensꢀglandulifera
Royle (Balsaminaceae) and their antioxidant activities, Natural Product Research, DOI:
10.1080/14786419.2018.1499644
To link to this article: https://doi.org/10.1080/14786419.2018.1499644
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NATURAL PRODUCT RESEARCH
https://doi.org/10.1080/14786419.2018.1499644
SHORT COMMUNICATION
Phenolic constituents of the aerial parts of Impatiens
glandulifera Royle (Balsaminaceae) and their
antioxidant activities
Katarzyna Szewczyka, Serhat Sezai Cicekb, Christian Zidornb and
Sebastian Granicac
aChair and Department of Pharmaceutical Botany, Medical University of Lublin, Lublin, Poland;
bDepartment of Pharmaceutical Biology, Christian-Albrechts-University of Kiel, Kiel, Germany;
cDepartment of Pharmacognosy and Molecular Basis of Phytotherapy, Warsaw Medical University,
Warsaw, Poland
ABSTRACT
ARTICLE HISTORY
Received 24 June 2018
Accepted 9 July 2018
As a continuation of investigating Impatiens L. genus, eight
flavonoids, eriodyctiol, eriodyctiol 7-O-b-ᴅ -glucoside, kaempferol
3-O-b-ᴅ -glucoside, kaempferol 3-O-b-ᴅ -galactoside, kaempferol
KEYWORDS
3-rhamnosyl-di-glucoside,
kaempferol
3-O-b-ᴅ -rutinoside,
Impatiens glandulifera;
Balsaminaceae; phenolics;
flavonoids; antioxidant
activity
quercetin 3-O-b-ᴅ -glucoside and quercetin 3-O-b-ᴅ -galactoside,
two phenolic acids – p-hydroxybenzoic acid and protocatechuic
acid, and 2-methoxynaphthalene-1,4-dione were isolated from
the aerial parts of I. glandulifera collected in Poland. The
structures of the compounds were established by analysis of their
spectroscopic (1H and 13C NMR) and spectrometric (MS) data,
as well as by comparison of these with those reported in the
literature. Quercetin 3-O-b-ᴅ -glucoside, kaempferol 3-O-b-ᴅ
-galactoside and kaempferol 3-O-b-ᴅ -rutinoside were isolated
for the first time from the investigated taxon. In addition, the
antioxidant activities in different tests of all obtained compounds
were evaluated. The results clearly showed that among analyzed
constituents, quercetin 3-O-b-ᴅ -glucoside exhibited antioxidant
activity comparable or better than ascorbic acid and Trolox which
were used as a positive control.
CONTACT Katarzyna Szewczyk
k.szewczyk@umlub.pl
Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2018.1499644.
ß 2018 Informa UK Limited, trading as Taylor & Francis Group

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K. SZEWCZYK ET AL.
1. Introduction
Impatiens glandulifera Royle (Himalayan balsam), belonging to the Balsaminaceae
family, is perennial plant growing in riparian zones along rivers on humid soils and in
wet woodlands (Vieira et al. 2016). The species is among the invasive plants, originally
ꢀꢁ
native to Asia, that is rapidly spreading across Europe (Trıska et al. 2013).
It has been reported that some species in the genus, I. balsamina L. and I. walleriana
Hook.f. especially, have valuable biological activities. I. balsamina have been applied for
a very long time in traditional Asian and American medicine. Depending on the kind of
disease, dried herb and leaves of the species have been used as a compresses on the
skin or as a tea (Yang et al. 2001). The specimen found also an application in Chinese
medicine in rheumatism therapy, and in fractures, swellings, contusions, as well as in
the beriberi disease (Fukumoto et al. 1996; Jiang et al. 2017).
In our previous study, we confirmed that the methanol extract from the aerial parts
of I. glandulifera contained significant amounts of phenolics and flavonoids and has
antimicrobial and antioxidant activities (Szewczyk et al. 2016).
The present study deals with the isolation and identification of phenolic
constituents from the aerial parts of I. glandulifera collected in Poland. The antioxidant
activity of the isolated compounds was also evaluated.
2. Results and discussion
2.1. Identification of isolated compounds
In the course of a phytochemical study of the methanolic extracts from the aerial parts of
I. glandulifera, eight flavonoids, two phenolic acids and 2-methoxy-1,4-naphthoquinone
were isolated using column chromatography and preparative HPLC.
The compounds were identified as 3,4-dihydroxybenzoic acid, protocatechuic acid
(1) (Chang et al. 2009), p-hydroxybenzoic acid (2) (Cornelius et al. 2010), eriodictyol
7-O-b-ᴅ-glucoside (3) (Ragab et al. 2010), quercetin 3-O-b-ᴅ-galactoside, hiperoside (4)
(Ye and Huang 2006), quercetin 3-O-b-ᴅ-glucoside, isoquercitrin (5) (Zinsmeister et al.
ꢁ
1977), kaempferol 3-O-b-ᴅ -galactoside, trifolin (6) (Wolbis et al. 2007), kaempferol
3-O-b-ᴅ-rutinoside, nicotiflorin (7) (Nishina et al. 2017), kaempferol 3-O-b-ᴅ-glucoside,
astragalin (8) (Demirezer et al. 2006), eriodictyol (9) (Ye and Huang 2006), kaempferol
3-rhamnosyl-diglucoside (10) (Fukumoto et al. 1994), and 2-methoxynaphthalene-1,
4-dione (11) (Ortin and Evans 2013) based on NMR and MS data as well as by
comparison with literature data of the above and related compounds. The structures
of all isolated compounds are shown in Figure S1.
The presence of compounds 1 and 2 were previously described in the leaves,
flowers, and roots of I. glandulifera (Szewczyk and Olech 2017) but these acids were
isolated for the first time in this study. Moreover, Vieira and co-authors (2016) isolated
3, 4, 8 and 10 from the the flowers of I. glandulifera, collected in Germany. Compound
11, isolated in this study, was earlier identified in the leaves (Chapelle 1974; Lobstein
et al. 2001), flowers (Lobstein et al. 2001; Ortin and Evans 2013), seed pods (Ortin and
Evans 2013), stems (Lobstein et al. 2001; Cimmino et al. 2016) and methanol extract
ꢀꢁ
from the roots (Trıska et al. 2013; Cimmino et al. 2016) of I. glandulifera.

NATURAL PRODUCT RESEARCH
3
Isoquercitrin (5), trifolin (6) and nicotiflorin (7) were isolated for the first time from
the investigated species. Although, 5 was earlier described in the leaves and stems of
I. balsamina (Chua 2016), leaves of I. bicolor Royle (Hasan and Tahir 2005), herb of
I. noli-tangere L. (Paun et al. 2018), and the aerial parts of I. parviflora DC. (Szewczyk
et al. 2016). Trifolin (6) was only found in the leaves of I. bicolor (Hasan and Tahir 2005).
2.2. Antioxidant activities
In our earlier report (Szewczyk et al. 2016), methanolic extract from the aerial parts of
I. glandulifera showed the highest antiradical activity among six species studied. Based
on these results, we decided to verify the antioxidant potential of isolated compounds
from this taxon.
The antioxidant activities of all isolated compounds were determined employing
the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2-azino-bis-(3-ethyl-benzthia-6-sulfonic
acid) (ABTS) radical scavenging assays. For all samples it was found that the radical
scavenging activity depended on concentration. At a dose of 1.0 mg/mL, the DPPH
scavenging abilities were the highest for compound 2 (98.69%), 5 (97.95%) and 3
(95.75%), and in the ABTSꢀ test for 5 (99.05%), 2 (97.26%) and 4 (96.32%). The EC50
values for scavenging DPPH and ABTS radicals are presented in Supplementary
Table S1. Among the analyzed compounds, isoquercitrin (5) (EC50 ¼ 0.01 0.03 mg/mL
for ABTS and 0.11 0.01 mg/mL for DPPH radicals) exhibited antioxidant activity com-
parable or better than ascorbic acid (EC50 ¼ 0.18 0.01 for ABTS and 0.11 0.01 mg/mL
for DPPH radicals) and Trolox (EC50 ¼ 0.20 0.01 for ABTS and 0.09 0.01 mg/mL for
DPPH radicals) which were used as a positive control.
The most active compound, 5 showed even up to eighteen-times higher EC50 value
than the Trolox. This is not in accordance with results reported for this compound
reported by Lee et al. (2015). The authors studied antioxidant activity of pure chemical
compounds, e.g. hiperoside and isoquercitrin, and these compounds also showed high
activity, however worse than ascorbic acid used as positive control.
3. Conclusions
The phytochemical investigation of the aerial parts of I. glandulifera let to isolation
and identification eleven phenolic compounds. Among these, hiperoside was the
predominant compound. Isoquercitrin, trifolin and nicotiflorin were isolated for the
first time from the investigated species.
Moreover, our findings demonstrated that isolated compounds, especially
p-hydroxybenzoic acid, eriodictyol 7-O-b-ᴅ -glucoside, hiperoside and isoquercitrin,
exhibit a strong activity against DPPH and ABTS radicals.
Taking into account results of present as well as previously published studies, it is
reasonable to conclude that I. glandulifera, is an abundant source of health benefitial
secondary metabolites.
Disclosure statement
No potential conflict of interest was reported by the authors.

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K. SZEWCZYK ET AL.
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