Fitokimia IB

Biochemical Systematics and Ecology 80 (2018) 94–121
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Biochemical Systematics and Ecology

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Phytochemistry of the genus impatiens (Balsaminaceae): A review T

Katarzyna Szewczyk
Department of Pharmaceutical Botany, Medical University of Lublin, Chodźki 1, 20-093, Lublin, Poland
A R T I C LE I N FO A B S T R A C T
Keywords: The genus Impatiens L. belongs to the Balsaminaceae family and includes more than 480 accepted species. This
Balsaminaceae genus grows in tropical and subtropical regions, mostly in tropical Africa, India, southwestern part of Asia, and
Impatiens southern China. Various phytochemical studies have been conducted; however, there are no recent reports that
Chemosystematics provide a comprehensive summary of the phytochemistry of Impatiens L. The review summarizes literature data
Flavonoids
on chemical components identified in the species of Impatiens L. The available information was collected from
Quinones
Terpenes
scientific databases through a search using the keyword ‘Impatiens’. Phytochemical studies led to the identifi-
cation and/or isolation of 300 different compounds that have been reported from 27 species. These compounds
encompass flavonoids, phenolic acids, coumarins, quinones, triterpenoid saponins, sterols, and alkaloids.
Additionally, phytochemical compositions of the essential oils of some species have been evaluated.
1. Introduction also in Japan, in the northern zone of Europe, Russia and North
America (Fischer, 2004; Grey-Wilson, 1980; Song et al., 2003; Utami,
The genus Impatiens, belonging to the Balsaminaceae family, en- 2012; Yu et al., 2016). The taxa occur from sea level to 4000 m altitude
compasses approximately 500 (Fischer, 2004; Grey-Wilson, 1980; Yu (Yu et al., 2016) and often grow in forests margins, in valleys, roadside
et al., 2016). In the eighteenth century, Carolus Linnaeus distinguished troughs, and along streams, generally on humid soils (Vrchotová et al.,
seven species of Impatiens (“Species Plantarum”, 1753). Early research 2011; Yu et al., 2016).
focused primarily on species found in Asia and eastern Africa, and then Some species in the genus, I. balsamina L. and I. walleriana Hook. f.
gradually began to include species from other parts of the world. in particular, have pharmaceutical importance. Furthermore, some taxa
Hooker (1908) presented the first thorough study of 158 species that are planted as ornamentals. However, due to such cultivations outside
was focused on plant morphology and encompassed a preliminary the respective home ranges, some species have become invasive pests,
classification. Apart from these early studies, attempts to describe the e.g. I. capensis Meerb., I. parviflora DC., and I. glandulifera Royle
whole genus were not performed for a long time. One of the reasons was (Bartomeus et al., 2010; Skálová Jarosik, 2013). On the other hand,
that Impatiens taxa were deemed particularly difficult research objects some species have become endangered in their native ranges and cur-
due to their morphology. Difficulties for scientists resulted primarily rently 32 species of Impatiens are listed in the Red List as threatened
from the large number of species and the inability to conduct com- (IUCN, 2018).
parative research on all of them. In addition, examination of herbarium In the present review, the phytochemistry of the genus Impatiens is
material is demanding due to semi-succulent stems, fleshy leaves, and discussed. For a comprehensive literature overview, published phyto-
fragile flowers. Moreover, capsules and seeds are heterogenous, and chemical data were retrieved from the ISI®Web of Science, ®Scopus,
due to the ballistic form of seed dispersal prevalent in the genus, ex- ®GoogleScholar, ®SciFinder, and ®Reaxys databases. Entries were con-
plosive dehiscence, mature seedpods are nearly impossible to study sidered until the end of February 2018. Exact spelling of scientific bo-
morphologically. These factors may affect the clarity of test results tanical names, including the abbreviations for botanical authors was
(Grey-Wilson, 1980; Lu and Chen, 1991; Yu et al., 2016). According to brought in line with standard usage as recommended by “The
the current listing in the taxonomical internet database (www. International Plant Names Index” (www.ipni.org) and “The Plant List”
theplantlist.org; accessed 05 February 2018), the genus comprises (www.theplantlist.org).
488 accepted taxa.
Impatiens species have been identified especially in tropical and 2. Summary of literature data
subtropical regions, primarily in the Old World flora in such areas as
tropical Africa, India, southwestern part of Asia, southern China, but The current literature contains studies describing the chemistry of
E-mail address: k.szewczyk@umlub.pl.
https://doi.org/10.1016/j.bse.2018.07.001
Received 18 April 2018; Received in revised form 1 July 2018; Accepted 4 July 2018
Available online 09 August 2018
0305-1978/ © 2018 Elsevier Ltd. All rights reserved.
K. Szewczyk Biochemical Systematics and Ecology 80 (2018) 94–121
Fig. 3. Chemical structure of compound 18 (R = H; MW = 732) and 19

(R = α-L-rha; MW = 878).
Fig. 4. Chemical structure of compound 20 (R = H; MW = 732) and 21

(R = α-L-rha; MW = 878).
Fig. 1. Kaempferol and kaempferol O-glycosides.
27 Impatiens species. In the phytochemically studied species, the fol-

lowing classes of compounds have been identified: phenolic com-
pounds, including flavonoids, phenols, coumarins; quinones, including
naphthoquinones and antraquinones; and triterpenes, consisting of
triterpenoid saponins. In the following sections these metabolites are
discussed.
2.1. Flavonoids
Phytochemical investigations of Impatiens species have led to the

isolation different types of flavonoids, represented mostly by flavonols,
flavones, and anthocyanins. Their structures are summarised in
Figs. 1–11.
One of the first study on the occurrence of flavonoids in taxa of the
genus Impatiens genus stems from 1958. Clevenger (1958) described the
occurrence of kaempferol (1), quercetin (27), and myricetin (45) in the
flowers of I. balsamina L.
Fig. 5. Quercetin and derivatives.
Hagen (1966) reported that stems of I. balsamina (genotype

1IHHPrPr) contained astragalin (2), isoquercitrin (28), and sepals
compounds 1 and 28.
From the 35% ethanol extract from fresh white petals of I. balsamina
(Japan) 1, 2, kaempferol-3-O-[2″-O-α-L-rhamnopyranosyl-3″-O-β-D-
glucopyranosyl]-β-D-glucopyranoside (3), nicotiflorin (4), 27, and rutin
(29) were isolated (Fukumoto et al., 1994, 1996). Among these com-
pounds, 2–4, and 27–28 were shown to significantly inhibit platelet-
activating factor (PAF) - induced hypotension (Oku and Ishiguro,
Fig. 2. Chemical structure of compound 17 [MW = 950].
95
Fig. 10. Chemical structure of compound 51 (MW = 432).
Fig. 6. Flavanones.
Fig. 7. Chemical structure of compound 45 (R = H; MW = 318) and 46 (R = β-

gal; MW = 480).
Fig. 11. Anthocyanidins.
Fig. 8. Apigenin and O-glucoside.

extract of the flowers of I. balsamina. In addition, it was established that
this compound inhibits tyrosinase in fungi, i.e. an enzyme involved in
the synthesis of melanin, and has an inhibitory effect on the growth of
Propionibacterium acnes.
Lei et al. (2010a) isolated two new flavone glycosides from the seeds
of I. balsamina and their structures were determined as quercetin 3-O-
[α-L-rhamnose-(1 → 2)-β-D-glucopyranosyl]-5-O-β-D-glucopyranoside
(30), and quercetin 3-O-[(6'''-O-caffeoyl)-α-L-rhamnose-(1 → 2)-β-D-
glucopyranosyl]-5-O-β-D-glucopyranoside (31). From the stems of I.
balsamina, purchased from Xuyi Herbal Slice Factory (China), 1, 2, 27,
and 28 were isolated (Chen et al., 2010). Mori et al. (2011) identified
compound 2 also in methanol extract of aerial parts of I. balsamina
collected from Khon Kaen in Thailand. In the 50% chloroform in me-
Fig. 9. Luteolin and chrysoeriol.
thanol extract of cultured roots of I. balsamina luteolin (49) was found
(Sakunphueak et al., 2013).
1999). Furthermore, from the flowers of I. balsamina, purchased from
Hua et al. (2001) used capillary electrophoresis to separation of 1, Nanjing Zelang Phar. CO. Ltd. (Nanjing, China), 1, 2, 4, kaempferol 3-
2, kaempferol 3-glucosyl-rhamnoside (5), and kaempferol 3-(p-cou- O-α-rhamnoside-7,4-di-O-β-galactoside (12), and 6-methoxykaemferol-
maroyl)-glucoside (6) in 80% methanolic extract from flowers of I. 3-O-β-D-glucosyl (1‴→2″)-β-D-glucopyranosyl-(6‴-(E)-caffeoyl)-7-O-β-
balsamina. Lim et al. (2006, 2007) also isolated 1 from the methanol D-glucopyranoside (17), 27, 29, ampelopsin (40), and 45 were isolated
96
using repeated column chromatography and semi-preparative HPLC (Li

et al., 2015b).
Chua (2016) used liquid chromatography coupled to tandem mass
spectrometer to identify metabolites extracted by water and aqueous
methanol (50% v/v) from the leaves and stems of I. balsamina. A higher
number of metabolites was extracted by 50% methanol than by pure
water, especially for phenolic acids and flavonoids. A few flavonols and
their derivatives such as 1, 27 and their glycosylated conjugates (2, 4,
28) were only detected in the plant leaf samples. decrease in response to PAF (platelet activiting factor), and also 1, 2,
Four new biflavonoid glycosides and nine known compounds were kaempferol 3-rhamnosyldiglucoside 3, 27, 28, apigenin 7-glucoside
isolated from the white flowers of I. balsamina growing in Asan, (48), and chrysoeriol (50) were obtained (Ueda et al., 2003).
Republic of Korea. Their structures were determined by means of Moreover, Szewczyk et al. (2016b) found that the aerial parts of I.
spectroscopic techniques as kaempferol 3-O-α-L-rhamnopyranosyl-(1 → walleriana Hook. f. contained 2, kaempferol di-O-rhamnoside-O-hexo-
2)-β-D-glucopyranoside (13), kaempferol 3-O-α-L-rhamnopyranosyl- side (26) and 28.
(1 → 6)-β-D-glucopyranoside (14), kaempferol 3-O-β-D-allopyranoside
(15), balsamiside A (18), balsamiside C (19), balsamiside B (20), bal- 2.1.1. Anthocyanidins
samiside D (21), quercetin 3-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glu- The genus Impatiens is rich in pelargonidin (60) and peonidin (64),
copyranoside (33), 1, 2, 27, 28, and 40 (Kim et al., 2017). which were isolated for the first time in the genus from the flowers of I.
The high performance countercurrent chromatography (HSCCC) balsamina. In this species cyanidin (52), delphinidin (54) (Alston and
method led to separation 1 and 27 in a hydroalcoholic extract from Hagen, 1958) and malvidin (55) (Forsyth and Simmonds, 1954;
stems of I. balsamina (Jiang et al., 2017). Hayashi et al., 1953) have been also described. Moreover, Klein and
Using UHPLC-DAD-MS3 analyzes, Szewczyk et al. (2016b) found Hagen (1961) detected compounds 52, 54, 60, 64 in the petals of I.
that aerial parts of I. balsamina and I. balfourii Hook. f. contained 2 and balsamina.
28. In I. balfourii kaempferol di-O-hexoside (10), kaempferol O-rhamno- Hagen (1966) reported that stems of I. balsamina (genotype
O-hexoside (22, MW = 594), kaempferol O-hexoside-O-mallonylhexo- 1IHHPrPr) contained cyanidin 3-glucoside (53) and pelargonidin 3-
side (23, MW = 696), kaempferol O-rhamnoside-O-mallonylhexoside glucoside (60). Moreover, sepals contained 1, 28, acylated pelargonidin
(24, MW = 680), and hyperoside (32) were also detected. 3-glucoside (61) and pelargonidin 3,5-diglucoside (62), and petals pe-
Three flavanone glycosides new for the genus, naringenin 4′-O-β-D- largonidin 3-glycoside-5-acetylglycoside (63).
glucuronopyranoside (41), naringenin 4′-O-α-L-rhamnopyranoside (42) Small amounts of 52 and leucocyanidin (66, Fig. 12) were obtained
and naringenin 4′-O-β-D-xylopyranoside (43), and six known, such as from I. capensis Meerb. (Clevenger, 1958). Bathe-Smith (1962) found
kaempferol 7-O-β-D-glucopyranoside (7), kaempferol 3-O-β-D-galacto- compound 66 in I. glandulifera Royle.
pyranoside (8), kaempferol 7-O-β-D-xylopyranoside (9), kaempferol 5- In the petals and stems of I. holstii, 52 and 55 were reported
O-β-D-xylopyranoside (25, MW = 418), 28, and naringenin 4′-O-β-D- (Klozová and Rokosavá, 1961).
glucopyranoside (44) were found in the buthanol extract from leaves of In the herb of I. noli-tangere 52, 55, and peonidin 3-O-glucoside (65)
I. bicolor Royle, collected in the Murree Hills, Pakistan. Structures were were identified using HPLC-MS analysis (Paun et al., 2018). The hy-
determined by means of co-chromatography, UV, HPLC, EI-MS, FAB-MS drolyzed leaf extracts of I. parviflora DC. yielded 66 and leucodelphi-
and 1H NMR spectroscopy (Hasan and Tahir, 2005). nidin (67, Fig. 13) (Bathe-Smith, 1962).
Small amounts of compounds 1 and 27 were obtained from I. ca- The occurrence of malvidin 3-glucoside (56) and malvidin 3,5-di-O-
pensis Meerb. (Clevenger, 1958). glucoside (58) has been identified in the flowers of I. textori (Ueno
Bathe-Smith (1962) found 1 and 27 in I. glandulifera Royle. From et al., 1969). Moreover, Tatsuzawa and co-authors (2009) found in the
the ethanol extract of the flowers of I. glandulifera, collected on the fresh purple flowers of I. textori (Fukagawa City, Hokkaido, Japan)
flooding shore areas of the river Oker in Braunschweig (Germany), 1, 2, immersed in 5% HOAc, two pigments describes as malvidin 3-O-[6-O-
kaempferol 3-O-6″-malonyl-glucoside (11), kaempferol 3-O-rhamnosyl- malonyl-β-D-glucopyranoside] (57) and malvidin 3-O-[6-O-(3-hydroxy-
diglucoside (16), 27, 32, quercetin 3-O-β-D-(6″-O-malonyl)-glucopyr- 3-methylglutaroyl)-β-glucopyranoside] (59).
anoside (36), eriodictyol 7-O-glucoside (38), 40, and myricetin 3-O-β-D- Clevenger (1971) confirmed the presence of 52 and 55 in the petals
galactopyranoside (46) were isolated using high performance coun- and shoots of nineteen Impatiens species. The author also identified 55
tercurrent chromatography (HSCCC) (Vieira et al., 2016). and 60 in 17 strains of Impatiens from New Guinea, belonging to the I.
In the aerial parts of I. glandulifera growing in Poland 1, 2 and 28, schlecteri – linearifolia and I. hawkeri – mooreana – nivea group
32, eriodictyol (37), and eriodictyol O-hexoside (39) were identified (Clevenger, 1978). Thakur and Nozzolillo. (1978) reported that red
using UHPLC-DAD-MS3 method (Szewczyk et al., 2016b). color of the root tips and mature roots of I. balsamina, I. balfouri, I.
The hybrid I. holstii Engl. et Warb. × I. sultani Hook. f. yielded 1 capensis, I. flaccida Arn., I. linearifolia Warb., I. platypetala Lindl., I. re-
(Bathe-Smith, 1962). pens Moon, I. schlechteri Warb., I. sultani Hook. f., and I. uguenensis
Quercetin 7,3′,4′-trimethylether-3-O-rutinoside (34) and 1, 27 were Warb. is associated mainly with the presence of leucocyanidins. The
also isolated from the herb of I. noli-tangere L. (Choi and Kim, 2002). main anthocyanin contained in I. balsamina and I. platypetala was 53.
Szewczyk et al. (2016b) reported that aerial parts of I. noli-tangere
contained 2, 28 and 32. Moreover, in the herb of I. noli-tangere, col- 2.2. Phenolic acids
lected from the Cluj region in Romania, 27–29, apigenin (47), 49, and
genistin (51) were identified using HPLC-MS analysis (Paun et al., Bohm and Towers (1962) investigated the phenols in the herb of 17
2018).
In the hydrolyzed leaf extracts of I. parviflora DC. 1 and 27 were
detected (Bathe-Smith, 1962). In the methanol extract of leaves of I.
parviflora DC. 2 and quercetin 3-O-hexoside (35) (Hromádková et al.,
2014), and in the aerial parts 2, 28 and 32 were identified (Szewczyk
et al., 2016b).
From the 35% ethanolic extract of flowers of I. textori Miq. (from
Gifu, Japan) flavones 47 and 49, which inhibited blood pressure Fig. 13. Chemical structure of compound 67 (MW = 322).
97
Table 1
Occurrence of phenolic acids in various species of Impatiens (Bohm and Towers,
1962).
Impatiens species Phenolic acid
69 71 72 73 74 76 79 82 83 84
I. balfourii Hook.f. (or I. insignis + + + + + +

DC.)
I. balsamina L. + + + + + +
I. capensis Meerb. + + + + + +
I. elegantissima Gilg + + + + +
I. flaccida Arn. + +
I. glandulifera Royle + + + + + + +
I. herzogii K.Schum. + + + + + +
I. mathildae Chiov. + + + + +
I. oliveri C.H.Wright ex W.Watson + + + + + +
(I. sodenii Engl. & Warb.)
I. pallida Nutt. + + + + + + +
I. parviflora DC. + + + + + +
I. platypetala Lindl. + + Fig. 16. Cinnamic acid derivatives.
I. repens Moon ex Wight + + + + + + +
I. scabrida DC. + + + + + + + +
I. schlechteri Warb. + + + Later, p-hydroxybenzoic acid (71) was also isolated from the 50%
I. sultani Hook.f. + chloroform in methanol extract from I. balsamina root cultures
I. walleriana Hook.f. + + + + + (Sakunphueak et al., 2013). From the methanol extract of the white
flowers of I. balsamina, 71, protocatechuic acid (72), vanilic acid (76),
69 - gentisic acid, 71 - p - hydroxybenzoic acid, 72 - protocatechuic acid, 73 -
p-hydroxybenzoic acid methyl ester (78, Fig. 15), and trans-p-coumaric
salicylic acid, 74 - syringic acid, 76 - vanillic acid, 79 – caffeic acid, 82 - p-
coumaric acid, 83 – ferulic acid, 84 - sinapic acid.
acid (82), trans-ferulic (83) acid were isolated (Kim et al., 2015).
Seven previously unknown and eleven previously reported com-
pounds were isolated from the flowers of I. balsamina, purchased from
Nanjing Zelang Phar. CO. Ltd. (Nanjing, China), through repeated
column chromatography and semi-preparative HPLC. Their structures
were elucidated using different spectroscopic methods, including 1D
and 2D-NMR, UV, IR, and HR–ESI–MS. The structures of isolated
compounds were identified as 2-O-(4- hydroxybenzoyl)-4-O-β-D-gluco-
pyranosyl-6-hydroxyphenylacetic acid (85), methyl 2-O-(4-hydro-
xybenzoyl)-4-O-β-D-glucopyranosyl-6-hydroxyphenylacetate (86), ethyl
2-O-(4-hydroxybenzoyl)-4-O-β-D-glucopyranosyl-6-hydro-
xyphenylacetate (87), butoxy 2-O-(4-hydroxybenzoyl)-4-O-β-D-gluco-
pyranosyl-6-hydroxyphenylacetate (88), butoxy 2-O-(4-hydro-
xybenzoyl)-4,6-dihydroxyphenylacetate (89), 1,2-O-(4-dihydroxy-
benzoyl)-2,4,6-trihydroxyphenylacetic acid (90), methyl 2-O-(4-hy-
droxybenzoyl)-2,4,6-trihydroxyphenylacetate (91), (6-O-p-coumaroyl)-
β-D-glucopyranosyl-2-O-(4-hydroxybenzoyl)-4-O-β-D-glucopyranosyl-6-
hydroxyphenylacetate (92, MW = 346), and 4-O-β-D-glucopyranosyl-
2,6-dihydroxyphenylacetic acid (93) (Li et al., 2015b). (see Figs. 17,
18).
Moreover, in the water and 50% methanol extract from leaves and
stems of I. balsamina salicylic acid (73), toluic acid (75), 79, 82, 83
were found. Furthermore, in a leaf water extract cinnamic acid (80) was
detected (Chua, 2016). The ultrasound assisted extraction was used to
determine the content of phenolic acids in leaves of I. balsamina. Gallic
acid (68), gentisic acid (69), 71, 72, syringic acid (74), 76, 79, 3-hy-
droxycinnamic acid (81), 82, 83, and cis-sinapic acid (84) were iden-
Fig. 14. Benzoic acid derivatives. tified in this species (Szewczyk and Olech, 2017).
From the ethyl acetate extract of I. bicolor (from Ayubia Park,
Muree, Pakistan) 83 was isolated and identified by X-ray analysis
(Shahwar et al., 2010).
Szewczyk and Olech (2017) studied various extraction methods for
the quantitative and qualitative analysis (LC-ESI-MS/MS) of phenolic
acids present in extracts obtained from leaves, flowers, and roots of I.
Fig. 15. Chemical structure of compound 78 (MW = 152). glandulifera collected in Poland. Using the ultrasound assisted extrac-
tion method, 3-hydroxybenzoic acid (70), 69, 71–74, 76, 79, 81, 83,
species of Impatiens. They were able to show that most of the phenolic and 84 were identified in all parts of studied species. Veratric acid (77)
compounds only become detectable after acidic or alkaline hydrolysis. was observed in the leaves and 80 in the flowers of I. glandulifera after
The phenolic acids detected after appropriate pretreatment of the ex- accelerated solvent extraction (ASE).
tracts are displayed in Table 1. Structures of benzoic acid derivatives in In the leaves of I. noli-tangere growing in Poland, 69, 71–74, 76, 79,
Fig. 14 andcinnamic acid derivatives in Fig. 16 are shown. and 81–83 were identified (Szewczyk and Olech, 2017).
98
Fig. 19. Coumarins.
Fig. 17. Depside derivatives.
from the ether extract from the flowers of I. balsamina. Yang and co-
authors (2001) isolated 100 from the 95% ethanol extract of the aerial
Fig. 18. Chemical structure of compound 93 (MW=346).
parts of I. balsamina using bioactivity-guided solvent–solvent parti-
tioning and column chromatography, followed by recrystallization from
Bathe-Smith (1962) found in hydrolyzed leaf extracts of I. parviflora methanol. The identification of the compound was achieved by UV, FT-
only 79, 82, and 83. The methanol extract of leaves of I. parviflora IR, MS and 1H and 13C NMR spectroscopy. Compound 100 was also
yielded 79 and 83 (Hromádková et al., 2014). In the leaves of I. par- determined from the methanol extract of aerial parts (Mori et al.,
viflora and I. walleriana (Poland) after the ultrasound assisted extrac- 2011), white flowers (Kim et al., 2015; Li et al., 2015a), pods, roots,
tion, 69, 71–74, 76, 79, 81, and 83 were observed. Compounds 69 and seeds (Wang et al., 2011), leaves (Ding et al., 2008; Wang et al., 2011),
82 were present in small quantities only in the leaves of I. walleriana stems (Jiang et al., 2017; Wang et al., 2011), and root cultures
(Szewczyk and Olech, 2017). (Panichayupakaranant et al. (1995) of I. balsamina.
The presence of another naphthoquinone, lawsone (101), was de-
2.3. Coumarins scribed for the first time in I. balsamina, I. capensis, and I. pallida by
Clevenger (1958). Later, 101 was achieved from leaves (Chua, 2016;
The first coumarin isolated from plants of the genus Impatiens was Sakunphueak and Panichayupakaranant, 2010; Sonandkar et al.,
scopoletin (94). The presence of this coumarin was noted in the leaves 2014a, 2014b), stems (Chua, 2016; Jiang et al., 2017), and root cultures
of the following species: I. balfourii, I. balsamina, I. capensis, I. ele- of I. balsamina (Panichayupakaranant et al., 1995).
gantissima, I. flaccida, I. glandulifera, I. herzogii, I. oliveri, I. pallida, I. Moreover, Panichayupakaranant et al. (1995) isolated the new
platypetala, I. repens, I. scabrida, I. schlechteri, I. sultani, I. walleriana bisnaphthoquinone, methylene-3,3′-bilawsone (104, MW = 360) from
(Hegnauer, 1964), the herb of I. noli-tangere (Choi and Kim, 2002), and the root cultures of I. balsamina. Ishiguro and co-authors (1998) isolated
in methanol extract from the lyophilized roots of I. glandulifera collected two new compounds, balsaminone A (106) and balsaminone B (107),
around Ceske Budejovice (Tříska et al., 2013). Later, from the root together with the known compound 100 from the pericarp of the fruit
cultures of I. balsamina 94 and isofraxidin (98) (Dawson and Holland, of I. balsamina. From the ethyl acetate-soluble parts of 35% ethanol
1999; Panichayupakaranant et al., 1995; Sakunphueak et al., 2013) extract from fresh corolla of I. balsamina two new 1,4-naphthoquinone
were extracted. From the same plant material, Panichayupakaranaut sodium salts, balsaminolate (103) and impatienolate (105) were iso-
and co-authors (1998) isolated a new biscoumarin, 4,4′-biisofraxidin lated (Oku and Ishiguro, 2002).
(96). From the flowers of I. balsamina two new quinones were isolated
The water and 50% aqueous methanol extract from the leaves and and their structures were elucidated as balsaminone D (109), balsa-
stems of I. balsamina contained 94 and fraxidin (97). In the water leaf minone E (110), 107 (Li et al., 2015a), and from the stems, 1α,2α-diol-
extract, coumarin (95) and glucosyl columbianetin (99, MW = 384) 4α-ethoxy-1,2,3,4-tetrahydronaphthalene (111) and 1α,2α,4β-triol-
were also present (Chua, 2016). The structures of coumarins are given 1,2,3,4-tetrahydronaphthalene (112) (Chen et al., 2010). Balsaminone
in Figs. 19, 20. C (108) and 106, 107 were also isolated from the seeds of I. balsamina
(Pei et al., 2012).
2.4. Quinones Sakunphueak et al. (2013) developed simple, rapid and sensitive
high-performance liquid chromatography (HPLC) and high-perfor-
The first derivative of naphtho-p-quinone was described by Little mance thin-layer chromatography (HPTLC) methods for quantification
et al. (1948) who isolated lawsone monomethyl ether (100, 2-MNQ) of 100, 101, and 104 in the leaves of I. balsamina. From the chloroform-
99
methanol (50:50,v/v) extract of I. balsamina root cultures 2,3-dihy-

droxy-1,4-napthoquinone (102) was isolated (Sakunphueak et al.,
2013) and from the roots and above-ground parts 1,2,4-trihydrox-
ynaphthalene-1-O-glucoside (117) were isolated (Tříska et al., 2013).
Kim et al. (2015) identified (3S, 4R)-3,4-dihydroxy-3,4-dihy-
dronapthalen-1(2H)-one (113), trans-(3S, 4R)-3,4-dihydroxy-1-tetra- Fig. 22. Chemical structure of compound 104 (R = OH; MW = 360) and 105
(R = ONa; MW = 418).
lone (114), hydroquinone (115), and tyrosol (116) in the white flowers
of I. balsamina growing in Asan, Korea.
Carboxyl lawsone (118, MW = 218) and 104 were detected in the
50% methanol extract from the leaves of I. balsamina (Chua, 2016).
Furthermore, 100 was identified in the leaves (Chapelle, 1974;
Lobstein et al., 2001; Ruckli et al., 2014), flowers (Lobstein et al., 2001;
Mitchell et al., 2007; Ortin and Evans, 2013), seed pods (Ortin and
Evans, 2013), stems (Cimmino et al., 2016; Lobstein et al., 2001; Ruckli
et al., 2014) and methanol extract from the roots (Cimmino et al., 2016; Fig. 23. Chemical structure of compound 106 (R = H; MW = 344) and 107
Ruckli et al., 2014; Tříska et al., 2013) of I. glandulifera. Lobstein et al. (R = glc; MW = 506).
(2001) developed a sensitive RP-HPLC method for the detection and
quantification of 100 and 101 in the leaves, stems and flowers of I.
glandulifera plants of different ages, and the flowering aerial parts of I.
capensis, I. noli-tangere, and I. parviflora. Ruckli et al. (2014) also found
101 in low quantities in the root tissue of I. glandulifera in the senescent
stage.
In the methanol extract of the roots and stems of I. glandulifera Fig. 24. Chemical structure of compound 108 (MW = 366).
plants, and in I. parviflora roots and above-ground parts of the plants
117 was identified (Tříska et al., 2013). The compound was also found
in the methanol extract of leaves of I. parviflora (Hromádková et al.,
2014). The structures of naphtho-p-quinone derivatives are given in
Figs. 21–32.
2.5. Terpenes
Shoji and co-authors (1994a, 1994b, 1994c) reported isolation and
structure determination of fifteen saponines named hosenkosides: A
(119), B (125), C (130), D (120), E (126), F (127), G (131), H (128), I
(129), J (121), K (122), L (123), M (124), N (132), and O (133) from
the 50% methanol extract from the seeds of I. balsamina purchased from
Sakata Seed Co., Yokohama, Japan. The structures of hosenkosides are
shown in Figs. 33–35. Tan et al. (2009) proposed a RP-HPLC-ELSD
method to quantify two baccharane glycosides – 119 and 122. In the Fig. 26. Chemical structure of compound 110 (MW = 361).
study using a high performance liquid chromatography (HPLC) com-
bined with electrospray ionization mass spectrometric detection (ESI –
MSD) and evaporative light scattering detection (ELSD), it was found
that the content of hosenkosides in seeds of I. balsamina can serve as a
marker for the qualitative determination of this raw material (Li et al.,
2011). Fu and co-authors (2012) performed a rapid-resolution liquid
chromatography coupled with electrospray ionization quadrupole time- Fig. 27. Chemical structure of compound 111 (MW = 209).
of-flight tandem mass spectrometry (RRLC/ESI-Q-TOF MS/MS) to in-
vestigate the fragmentation behaviours of baccharane glycosides from
seeds of I. balsamina. The authors devided analyzed compounds into
three types: hosenkol A (included 119, 120, 122–124), hosenkol B (125
and 127), and hosenkol C (130 and 131) type, which differ in the
Fig. 29. Chemical structure of compound 113 (R = α-OH; MW = 178) 114

(R = β-OH; MW = 178).
baccharane skeleton.
A new triterpene ester, α-amyrin caffeate (134) (Fig. 36), was iso-
lated from the seeds of I. balsamina (Lei et al., 2010b). From the
chloroform-methanol (50:50,v/v) extract of I. balsamina root cultures
Fig. 21. Chemical structure and molecular weight of compounds 100–103. echinocystic acid (135) (Fig. 37) was isolated (Sakunphueak et al.,
100
Fig. 34. Chemical structure and molecular weight of hosenkosides 125–129;

Ra = β-D-glc; Rb = β-D-glc (2 → 1)-β-D-glc; Rc = β-D-glc (2 → 1)-β-D-xyl.
Fig. 33. Chemical structure and molecular weight of hosenkosides 119–124;

Ra = β-D-glc; Rb = β-D-glucopyranosyl (2 → 1)-β-D-glucopyranosyl; Rc = β-D-
glucopyranosyl (2 → 1)-β-D-xylopyranosyl. Fig. 35. Chemical structure and molecular weight of hosenkosides 130–133;
Ra = β-D-glc; Rb = β-D-glc (2 → 1)-β-D-glc; Rc = β-D-glc (2 → 1)-β-D-xyl.
2013).
Four new triterpene saponins and six known compounds were iso-
lated from I. balsamina flowers through repeated column chromato-
graphy and semi-preparative HPLC. Their structures were elucidated by
the NMR (1D and 2D), and HR-ESIMS methods. The following new
compounds were determined: balsaminside A (136), balsaminside B
(137), balsaminside C (138), balsaminside D (139) (Fig. 38). Besides
these, the known compounds were identified as β-D-glucopyr-
anosiduronic acid, (3β)-norolean-3-yl-O-β-D-glucopyranosyl-(1 → 2)-O-
[β-D-xylopyranosyl-(1 → 4)] (140), 3-O-β-D-xylopyranosyl-(1 → 2)-β-D- Fig. 36. Chemical structure of compound 134 (MW = 586).
glucopyranosyl-28-O-β-D-glucopyranosyl oleanolic acid (141) (Fig. 39)
(Li et al., 2017). and HRESIMS data. The authors found also 100 and 142 in the stems,
α-Spinasterol (142, Fig. 40) was isolated from roots, stems, leaves leaves and roots (Cimmino et al., 2016). From the herb of I. noli-tangere
(Wang et al., 2011), and root cultures (Sakunphueak et al., 2013) of I. α-spinasterol-3-O-β-D-glucopyranoside (145, Fig. 43) was isolated (Choi
balsamina. and Kim, 2002).
From the stems of I. glandulifera collecting in Belgium, two new In the leaves of I. parviflora growing in Poland, two new triterpene
glucosylated steroids which structures were characterized as glanduli- were found and their structures were determined using 1D and 2D-
ferin A (143, Fig. 41) and glanduliferin B (144, Fig. 42) based on NMR NMR, and mass spectrometry as IPS-1 (146) and IPS-2 (147) (Fig. 44)
101

Fig. 38. Chemical structure and molecular weight of balsaminsides.
Fig. 44. Chemical structure of compound 146 (R = COCH3; MW = 1017) and

147 (R = H; MW = 975).
Fig. 39. Chemical structure of compound 140 (MW = 1100) and 141
(MW = 1076).
(Grabowska et al., 2017).

The phytochemical investigation of I. pritzellii have yielded 142,
145, spinasteryl-3-one (148, Fig. 45), α-spinasteryl-3β-O-palmitate
(149, Fig. 46), 3-O-[6′-O-palmitoyl-β-D-glucosyl]-spinasterol (150,
MW = 812), hentriacontane (151, Fig. 47), and 2′-acetamido-3′-phenyl
propyl 2-benzamido-3-phenyl propionate (152, MW = 444) (Zhao
102
Fig. 49. Chemical structure and molecular weight of triterpenoid saponins

identified in I. siculifer Hook. f.
Fig. 48. Chemical structure and molecular weight of compounds 153–158.
et al., 2005a, 2005b).

From the buthanol fraction of the rhizomes of I. pritzellii var. hupe-
hensis 3-O-β-D-glucuronopyranosyl echinocystic acid (153), 3-O-[(6-O-
methyl)-β-D-glucuronopyranosyl] echinocystic acid (154), 3-O-[(6-O-
ethyl)-β-D-glucuronopyranosyl] echinocystic acid (155), 3-O-[(6-O-
nbutyl)-β-D-glucuronopyranosyl] echinocystic acid (156), and 3-O-[(6-
O-n-butyl)-β-D-glucuronopyranosyl]-28-O-[β-D-xylopyranosyl-(1 → 4)-
α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl] echinocystic acid
(157) (Fig. 48), and 135 were isolated (Zhou et al., 2009a,b). It have
been shown that these compounds have an inhibitory effect on the
production of interleukin (IL) 18 (Zhou et al., 2009a,b).
Seven new triterpenoid saponins and twelve known saponins were
isolated from the whole plants of I. siculifer Hook. f. (Figs. 49 and 50).
Their structures were characterized based on 1D and 2D NMR and MS
analyses coupled with chemical degradation. The known saponins were
identified as 3-O-α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyr-
anosyl-soyasapogenol E (159), soyasaponin Bg (160), dehy-
drosoyasaponin I (161), sandosaponin A (162), soyasapogenol B
monoglucuronide (163), soyasaponin IV (164), soyasaponin I (165), Fig. 50. Chemical structure and molecular weight of triterpenoid saponins from
I. siculifer Hook. f.
soyasaponin I methyl ester (166), soyasaponin II (167), 22-O-β-D-glu-
copyranosyl-(1 → 3)-α-L-arabinopyranosyl-soyasapogenol A (169), 3-O-
α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranosyl-22-O-β-D-
103
glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-soyasapogenol A (170),

and soyasaponin A1 (171). The new triterpenoid saponins were de-
termined as impatienoside G (158), impatienoside A (168), im-
patienoside B (172), impatienoside C (173), impatienoside D (174),
impatienoside E (175), and impatienoside F (176) (Li et al., 2009).
2.6. Fatty acids Fig. 55. Chemical structure of fatty acids.
According to Kaufmann and Keller (1950), the Impatiens species

contain glycerides, in which fatty acids and parinaric acid (177, Fig. 51)
are found as fatty acids.
From the flowers of I. balsamina through repeated column chro-
matography and semi-preparative HPLC, glycerol 9(E),11(Z),13(E)-oc- Fig. 56. Chemical structure of compound 191 (R = H; MW = 189) and 192
(R = β-D-glc; MW = 351).
tadecatrienoyl ester (178, Fig. 52) (Li et al., 2017).
From the chloroform-methanol (50:50,v/v) extract of I. balsamina
root cultures methyl linolenate (179, Fig. 53) was isolated
(Sakunphueak et al., 2013). In the water and 50% methanol extract
from leaves and stems of I. balsamina 177 and chavicol acetate (180,
Fig. 54) were detected (Chua, 2016).
Compound 177 was found as a major constituent fatty acid from
seed oil of I. edgeworthii Hook. f. (Bagby et al., 1966). Fig. 57. Chemical structure of compound 193 (MW = 288) and 194
From the oil of I. glandulifera, an acetodiparinarine (181) was iso- (MW = 290).
lated. This seed oil has been extensively studied. Saponification yielded
13% glicerol (182, MW = 92), 10% acetic acid (183, MW = 60),
40–50% of 177, about 3% palmitic acid (184, MW = 256), about 3%
stearic acid (185, MW = 284), and about 20% oil plus linoleic (186,
MW = 280) plus linolenic acid (187, MW = 278) (Fig. 55). The seeds of
a number of other Impatiens species also contained oil with 177 and 183
containing glycerides (Kaufmann and Keller, 1950). Fig. 58. Chemical structure of compound 195 (MW = 155).
Ortin and Evans (2013) noticed that the hydrophobic extracts from
flower stalks with seed pods of I. glandulifera contained 184, 185, 187,
arachidic acid (188, MW = 312) and trans-tetradec-2-enoic acid (189,
MW = 226) and trans-tetradec-2-enoic acid methyl ester (190,
MW = 240) (Fig. 55).
104
Asan, Korea. Their structures were established as balsamitril (191) and

balsamitril-3-O-β-D-glucoside (192) (Fig. 56).
Chua (2016) found 8-ethyl-10-hydroxyethyl lobelionol (193) in the
Fig. 60. Chemical structure of compound 198 (MW = 714) and 199 (R = β- leaves and stems of I. balsamina, and 8-ethyl-10-phenyllobelionol (194)
OH; MW = 714).
(Fig. 57)in water extract from the leaves.
From the I. capensis seeds scopoline (195, Fig. 58) was determined
(Hegnauer, 1989).
Hypaphorine (196; Fig. 59), an α-N,N,N-trimethyltryptophan be-
Fig. 61. Chemical structure of compound 200 (MW = 395). taine with antihyperglycemic activity, was isolated as major constituent
from I. niamniamensis seeds. The structure of the compound was es-
tablished by spectroscopic data (Chand et al., 2011).
2′-acetamido-3′-phenyl propyl 2-benzamido-3-phenyl propionate
(197, MW = 207) (Zhao et al., 2005b), and soyacerebroside I (198) and
soyacerebroside II (199) from rhizomes of I. pritzellii Hook. f. var. hu-
pehensis Hook. f. were isolated (Zhou et al., 2009a,b). The structures of
two cerebrosides were identified by spectroscopic analysis as soyacer-
ebroside I (198) and soyacerebroside II (199) (Fig. 60) (Zhou et al.,
2009a,b).
Furthermore, from I. siculifer N-phenyl-2-naphthylamine (200,
Fig. 61) was determined (Du and Xu, 1995).
Fig. 62. Chemical structure of sugars.

2.8. Volatile compounds
Using optimal supercritical extraction Zhou et al. (2014) identified

in the whole plants of I. balsamina following compounds: 1-chloro-
hexadecane (201, MW = 260), 2-carbonyl-6,10-dimethy-5,9-un-
decadien (202, MW = 182), 5,6,7,7α-hydro-4,4,7α-trimethyl-tetr-
2(4H)-benzofuranone (203, MW = 180), 2-sulfonamide naphthalene
(204, MW = 207), 6,10,14-trimethyl-2-pentadecanone (205,
MW = 268), methyl hexadecanoate (206, MW = 270), decyl-3,4-di-
methyl-phenyl phthalic acid ester (207, MW = 374), [1,2,4]triazolo
[1,5-α]pyrimidine-6-carboxylic acid-4,7-dihydro-7-imino-ethyl ester
(208, MW = 207), N-butyl-cis-4-cyclohexene-1,2-dicarboximide (209,
MW = 207), [2-(2,5-dimethyl-1H-pyrrol-1-yl)ethyl]-1-piperazine (210,
Moreover, 185 was found in I. pritzellii (Zhao et al., 2005a). MW = 207), eicosane (211, MW = 282), 1-tricosane (212,
MW = 324), 2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetra-
2.7. Nitrogenous compounds cosahexaene (213, MW = 422), octadecane (214, MW = 254).
Forty two volatile components were characterized in the n-hexane
The nitrogenous compounds are rather rare in Balsaminaceae. extract of I. bicolor growing in Pakistan. The major ones were fatty acid
Nevertheless, Kim et al. (2015) isolated two new phenolic compounds methyl esters, such as trans-methyl 13-octadecenoate (215,
with nitrile group from the white flowers of I. balsamina growing in MW = 296), methyl heptadecanoate (216, MW = 284), methyl
105
Fig. 67. Chemical structure of amino acids.
octadecanoate (217, MW = 298), methyl docosanoate (218,

MW = 354), methyl tetracosanoate (219, MW = 382) and methyl ei-
cosanoate (220, MW = 326), and aliphatic hydrocarbons (Nisar et al.,
2012).
Essential oils from I. balsamina, I. glandulifera, I. noli-tangere and I.
parviflora growing in Poland were obtained by steam distillation from
air-dried herbs and roots. Seventy six compounds were identified in the
herb oil of I. glandulifera. The oil was dominated by oxygenated
Fig. 68. Chemical structure of organic acids. monoterpenes, and α-terpinyl acetate (221, MW = 196) was the major
constituent, followed by phellandral (222, MW = 152). Phthalides
were the most characteristic constituents of this oil: (Z)-ligustilide (223,
MW = 190) and (Z)-butylidenphthalide (224, MW = 188) were ac-
companied by small amounts of their (E)-isomers and butylphthalide
(225, MW = 190). This oil was the only one that contain pronounced
Fig. 69. Chemical structure of compounds 289 (MW = 146) and 290 amounts of monoterpene hydrocarbons, and β-phellandrene (226,
(MW = 131).
MW = 136) was the main one in this group. Three major groups of the
constituents of the root oil of I. glandulifera (94 compounds) were ali-
phatic, mono- and sesquiterpene oxygenated compounds. The main
component was sesquiterpene ketone, vulgarone B (227, MW = 218).
Linalool (228, MW = 154), borneol (229, MW = 154) and bornyl
acetate (230, MW = 196) were the major monoterpenes. Another im-
Fig. 70. Chemical structure of compound 291.
portant constituent was pentadecanal (231, MW = 226). The main
feature of this oil was the presence of sixteen sesquiterpene hydro-
carbons, with β-barbatene (232, MW = 204) being the major one.
106
(Gurusinghe and Bradford, 2001).

Furthermore, from I. balsamina flowers α-D-glucopyranosyl-(1 → 1′)-
3′-amino-3′-deoxy-β-D-glucopyranoside (256) was isolated (Fig. 64) (Li
et al., 2017).
Preliminary characterization of water-soluble polysaccharides from
I. balsamina, I. glandulifera, I. noli-tangere and I. parviflora were in-
vestigated by Szewczyk et al. (2018). The sugar composition analysis
revealed that Impatiens polysaccharides consisted primarily of
247–249, arabinose (250, MW = 150), mannose (251, MW = 180),
and rhamnose (252, MW = 164). All polysaccharide fractions, except
for I. parviflora roots, also contain galacturonic acid (253, MW = 194).
(see Fig. 62).
Hromádková et al. (2014) studied non-cellulosic polysaccharides
from the leaves of I. parviflora. From the pre-extracted leaves, poly-
saccharides were determined using five-step extraction procedure. For
this purpose cold water, 0,05 M EDTA, DMSO, and 1% and 5% NaOH
were used as extractants. Polysaccharide fractions contained 247–252,
and fucose (254, MW = 164). Moreover, first three fractions contained
methylglucuronoxylan (257) and arabinogalactan (258, Fig. 65). The
alkali-extracted fraction comprised a degraded 257 and type II 258 in
about equal amounts.
From rhizomes of I. pritzellii 2-amino-2-deoxy-D-glucose (259,
Fig. 66) was determined and identified using spectroscopic methods
such as IR, MS, 1D and 2D NMR (Zhou et al., 2007a,b).
2.10. Amino acids and amino derivatives
A high molecular weight protein has been isolated as a major

polypeptide in the fruit pericarp of the plant I. balsamina from Bose
Institute Garden in Calcutta (India). Amino acid analysis showed the
presence of more acidic amino acids, with an isoelectric point 5.8. The
major amino acids were aspartic acid (260, MW = 133) and glutamic
Fig. 72. Chemical structure of carotenoids.
acid (261, MW = 147), tyrosine (262, MW = 181), leucine (263,
MW = 131), glycine (264, MW = 75), proline (265, MW = 115) and
Eighteen constituents were identified in both herb and root oils of I. serine (266, MW = 105) (Fig. 67) (Pal and Biswas, 1994).
glandulifera, e.g., hexanal (233, MW = 100), heptanal (234, The leaves and stems of I. balsamina contained aminobutyric acid
MW = 114), nonanal (235, MW = 142), benzaldehyde (236, (267, MW = 103), valine (268, MW = 117), pyroglutamic acid (269,
MW = 106), 228, 229 and 230, terpinene-4-ol (237, MW = 154), α- MW = 129), alanyl alanine (270, MW = 160), hydroxyglycyl glycine
terpineol (238, MW = 154), β-ionone (239, MW = 192) and its ep- (271, MW = 166), hydroxytryptophan (272, MW = 220), glutaryl
oxide. Among the twelve sesquiterpene hydrocarbons only δ-cadinene deoxyalanyl alanine (273, MW = 273), and glutaryl alanylalanine
(240, MW = 204) was common for both oils. In the essential oil of I. (274, MW = 290). In the leaves isoleucine (275, MW = 131), hydro-
parviflora herb, seventy compounds were identified and among them, xylysine (276, MW = 162), phenylalanine (277, MW = 165), 1-deoxy-
(E)-hex-3-en-1-ol (241, MW = 100), 228 and 236 were the most pro- 1-fructosyl isoleucine (278, MW = 293), and caffeoyl leucine (279,
minent. The number of identified components in the oil of I. parviflora MW = 311) were also noticed (Chua, 2016).
roots was eighty nine and the major compounds were 228, citronellol
(242, MW = 156) and geranial (243, MW = 152). Eighty components 2.11. Others compounds
were identified in oil from I. balsamina herb. The major constituent was
hexahydrofarnesyl acetone (244, MW = 268). Pronounced contents of From the organic acid, in the leaves and stems of I. balsamina, gly-
ionones and damascones, as well as fatty acids C6-C16 and alkanes ceric acid (280, MW = 106), fumaric acid (281, MW = 116), succinic
were characteristic features of this oil. The main member of the first acid (282, MW = 118), tartronic acid (283, MW = 120), malic acid
group was 239, and of the second group, dodecanoic acid (245, (284, MW = 134), 2-hydroxyterpenylic acid (285, MW = 188), glu-
MW = 200), ionones and damascones. 239 and its epoxide were also conic acid (286, MW = 196), lauric acid (287, MW = 200), and tri-
found in other investigated oils, however in smaller amounts. Among hydroxyl caffeic acid (288, MW = 226) were identified (Fig. 68) (Chua,
54 identified constituents of the total essential oil from I. noli-tangere 2016).
herb, the main compounds were (Z)-hex-3-enol (246, MW = 100), 228 Lanza et al. (1995) found high nectar concentrations of glutamine
and 236 (Szewczyk et al., 2016a). (289) and hydroxyproline (290) in I. capensis (Fig. 69).
Li et al. (2017) isolated 6-O-(E)-p-hydroxy-cinnamoyl-β-D-glucose
2.9. Sugars (291, Fig. 70), 6-O-(E)-p-hydroxy-cinnamoyl-α-D-glucose (292, Fig. 70),
and autantiamide acetate (293, Fig. 71) from the flowers of I. balsa-
According to Earle and Jones (1962), the seeds of I. balsamina mina).
contain 3.3% ash, 16.2% protein and 21.8% fat oil. Hydrolysis yielded In I. noli-tangere the occurrence of carotenoids has been detected. In
glucose (247, MW = 216), galactose (248, MW = 180) and xylose the course of the studies cryptoxanthin (294, MW = 552), neoxanthin
(249, MW = 150). (295, MW = 600) and cryptoxanthin epoxide (296, MW = 568) have
Impatiens L. seeds contain oligosaccharide planteose (255, Fig. 63), been detected (Kleinig and Nietsche, 1968). In 1972, 295 was isolated
which was first described in the Balsaminaceae family in 1977.255 from petals of the taxa (Nitsche and Pleugel, 1972). The flower pig-
together with sucrose affects the longevity of I. balsamina seeds ments of I. noli-tangere have been also studied by Wrischer et al. (1999),
107
Table 2
The overview on the compounds identified in the Impatiens genus.
K. Szewczyk
Constituent name Species Part of plant References
1. Kaempferol I. capensis flowers Clevenger, 1958

I. glandulifera leaves Bathe-Smith, 1962
I. holstii x
I. sułtani
I. parviflora
I. balsamina sepals Hagen, 1966
I. balsamina petals Fukumoto et al., 1994, 1996
I. balsamina flowers Clevenger, 1958
Hua et al., 2001
Lim et al., 2006, 2007
Li et al., 2015b
Kim et al., 2017
I. noli-tangere herb Choi and Kim, 2002
I. textori flowers Ueda et al., 2003
I. balsamina stems Chen et al., 2010
Jiang et al., 2017
I. balsamina leaves Chua, 2016
I. glandulifera flowers Vieira et al., 2016
I. glandulifera aerial parts Szewczyk et al., 2016b
2. Astragalin I. balsamina flowers Hua et al., 2001
Li et al., 2015b
I. balsamina stems Hagen, 1966
Chen et al., 2010
I. parviflora leaves Hromádková et al., 2014
108
I. balfourii, aerial parts Szewczyk et al., 2016b
I. balsamina,
I. glandulifera,
I. noli-tangere,
I. parviflora,
I. walleriana
I. balsamina aerial parts Mori et al., 2011
3. Kaempferol 3-O-[2″-O-α-L-rhamnopyranosyl-3″-O-β-D -glucopyranosyl]-β-D-glucopyranoside I. balsamina petals Fukumoto et al., 1994, 1996
4. Nicotiflorin I. balsamina petals Fukumoto et al., 1994, 1996
I. balsamina flowers Li et al., 2015b
5. Kaempferol 3-glucosyl-rhamnoside I. balsamina flowers Hua et al., 2001
6. Kaempferol 3-(p-coumaroyl)glucoside I. balsamina flowers Hua et al., 2001
7. Kaempferol 7-O-β-D-glucopyranoside I. bicolor leaves Hasan and Tahir, 2005
8. Trifolin I. bicolor leaves Hasan and Tahir, 2005
9. Kaempferol 7-O-β-D-xylopyranoside I. bicolor leaves Hasan and Tahir, 2005
10. Kaempferol di-O-hexoside I. balfourii aerial parts Szewczyk et al., 2016b
11. Kaempferol 3-O-6″-malonyl-glucoside I. glandulifera flowers Vieira et al., 2016
12. Kaempferol 3-O-α-rhamnoside-7,4-di-O-β-galactoside I. balsamina flowers Li et al., 2015b
13. Kaempferol 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside I. balsamina flowers Kim et al., 2017
14. Kaempferol 3-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranoside I. balsamina flowers Kim et al., 2017
15. Kaempferol 3-O-β-D-allopyranoside I. balsamina flowers Kim et al., 2017
16. Kaempferol 3-O-rhamnosyl-diglucoside I. glandulifera flowers Kim et al., 2017
17.6-Methoxykaemferol-3-O-β-D-glucosyl (1‴→2″)-β-D-glucopyranosyl-(6‴-(E)-caffeoyl)-7-O-β-D-glucopyranoside I. balsamina flowers Li et al., 2015b
18. Balsamiside A I. balsamina flowers Kim et al., 2017
19. Balsamiside C I. balsamina flowers Kim et al., 2017
20. Balsamiside B I. balsamina flowers Kim et al., 2017
21. Balsamiside D I. balsamina flowers Kim et al., 2017
(continued on next page)
Table 2 (continued)

K. Szewczyk
22. Kaempferol O-rhamno-O-hexoside I. balfourii aerial parts Szewczyk et al., 2016b

23. Kaempferol O-hexoside-O-mallonylhexoside I. balfourii aerial parts Szewczyk et al., 2016b
24. Kaempferol O-rhamnoside-O-mallonylhexoside I. balfourii aerial parts Szewczyk et al., 2016b
25. Kaempferol 5-O-β-D-xylopyranoside I. bicolor leaves Hasan and Tahir, 2005
26. Kaempferol di-O-rhamnoside-O-hexoside I. walleriana aerial parts Szewczyk et al., 2016b
27. Quercetin I. balsamina flowers Clevenger, 1958
Li et al., 2015b
I. parviflora, leaves Bathe-Smith, 1962
I. glandulifera
I. balsamina petals Fukumoto et al., 1994, 1996
Paun et al., 2018
Jiang et al., 2017
I. balsamina leaves Chua, 2016
I. balsamina flowers Kim et al., 2017
28. Isoquercitrin I. textori flowers Ueda et al., 2003
I. bicolor leaves Hasan and Tahir, 2005
Hagen, 1966
I. balsamina,
I. glandulifera,
I. noli-tangere,
109
I. parviflora,
I. walleriana
I. balsamina flowers Kim et al., 2017
I. noli-tangere herb Paun et al., 2018
29. Rutin I. balsamina petals Fukumoto et al., 1994, 1996
I. balsamina flowers Li et al., 2015b
30. Quercetin 3-O-[α-L-rhamnose-(1 → 2)-β-D-glucopyranosyl]-5-O-β-D-glucopyranoside I. balsamina seeds Lei et al., 2010
31. Quercetin 3-O-[(6””-O-caffeoyl)-α-L-rhamnose-(1 → 2)-β-D-glucopyranosyl]-5-O-β-D-glucopyranoside I. balsamina seeds Lei et al., 2010
32. Hyperoside I. glandulifera flowers Vieira et al., 2016
I. glandulifera,
I. noli-tangere,
I. parviflora
33. Quercetin 3-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranoside I. balsamina flowers Kim et al., 2017
34. Quercetin 7,3′,4′-trimethylether-3-O-rutinoside I. noli-tangere herb Choi and Kim, 2002
35. Quercetin 3-O-hexoside I. parviflora leaves Hromádková et al., 2014
36. Quercetin 3-O-6″-malonyl-glucoside I. glandulifera flowers Vieira et al., 2016
37. Eriodictyol I. glandulifera aerial parts Szewczyk et al., 2016b
38. Eriodictyol 7-O-glucoside I. glandulifera flowers Vieira et al., 2016
39. Eriodictyol O-hexoside I. glandulifera aerial parts Szewczyk et al., 2016b
40. Ampelopsin I. balsamina flowers Li et al., 2015b; Paun et al., 2018
41. Naringenin 4′-O-β-D-glucuronopyranoside I. bicolor leaves Hasan and Tahir, 2005
42. Naringenin 4′-O-α-L-rhamnopyranoside I. bicolor leaves Hasan and Tahir, 2005
43. Naringenin 4′-O-β-D-xylopyranoside I. bicolor leaves Hasan and Tahir, 2005
44. Naringenin 4′-O-β-D-glucopyranoside I. bicolor leaves Hasan and Tahir, 2005
45. Myricetin I. balsamina flowers Clevenger, 1958
Li et al., 2015b
Table 2 (continued)

K. Szewczyk
46. Myricetin 3-O-galactoside I. glandulifera flowers Vieira et al., 2016

47. Apigenin I. textori flowers Ueda et al., 2003
48. Apigenin 7-glucoside I. textori flowers Ueda et al., 2003
49. Luteolin I. textori flowers Ueda et al., 2003
I. balsamina root cultures Sakunphueak et al., 2013
50. Chrysoeriol I. textori flowers Ueda et al., 2003
51. Genistin I. noli-tangere herb Paun et al., 2018
52. Cyanidin I. balsamina petals Klein and Hagen, 1961
I. capensis flowers Clevenger, 1958
I. holstii petals, stems Klozová and Rokosavá, 1961
53. Cyanidin 3-O-glucoside I. balsamina stems Hagen, 1966
I. platypetala roots Thakur and Nozzolillo., 1978
54. Delphinidin I. balsamina flowers Alston and Hagen, 1958
I. balsamina petals Klein and Hagen, 1961
55. Malvidin I. holstii petals, stems Klozová and Rokosavá, 1961
I. schlecteri – petals, shoots Clevenger, 1978
linearifolia
I.hawkeri – mooreana
– nivea
56. Malvidin 3-glucoside I. textori flowers Ueno et al., 1969
57. Malvidin 3-O-(6″-malonyl)glucoside I. textori flowers Tatsuzawa et al., 2009
58. Malvidin 3,5-di-O-glucoside I. textori flowers Ueno et al., 1969
110
59. Malvidin 3-O-[6″-O-(3-hydroxy-3-methylglutaryl)-β-glucopyranoside] I. textori flowers Tatsuzawa et al., 2009
60. Pelargonidin I. balsamina flowers Alston and Hagen, 1958
I. balsamina petals Klein and Hagen, 1961
I. balsamina stems Hagen, 1966
61. Pelargonidin 3-glucoside I. balsamina sepals Hagen, 1966
62. Pelargonidin 3,5-diglucoside I. balsamina sepals Hagen, 1966
63. Pelargonidin 3-glucoside-5-acetylglucoside I. balsamina sepals Hagen, 1966
64. Peonidin I. balsamina petals Klein and Hagen, 1961
65. Peonidin 3-O-glucoside I. noli-tangere herb Paun et al., 2018
66. Leucocyanidin I. capensis flowers Clevenger, 1958
I. glandulifera flowers Bathe-Smith, 1962
I. parviflora leaves
67. Leucodelphinidin I. parviflora leaves Bathe-Smith, 1962
68. Gallic acid I. balsamina leaves Szewczyk and Olech, 2017
I. walleriana
69. Gentisic acid I. balsamina, leaves Szewczyk and Olech, 2017
I. noli-tangere,
I. parviflora,
I. walleriana
70. m-Hydroxybenzoic acid I. glandulifera flowers, leaves, Szewczyk and Olech, 2017
roots
71. p-Hydroxybenzoic acid I. balsamina flowers Kim et al., 2015
I. balsamina, leaves Szewczyk and Olech, 2017
I. noli-tangere,
I. parviflora,
I. walleriana
Table 2 (continued)

K. Szewczyk
72. Protocatechuic acid I. balsamina flowers Kim et al., 2015

I. noli-tangere,
I. parviflora,
I. walleriana
73. Salicylic acid I. balsamina leaves, stems Chua, 2016
I. noli-tangere,
I. parviflora,
I. walleriana
74. Syringic acid I. balsamina, leaves Szewczyk and Olech, 2017
I. noli-tangere,
I. parviflora,
I. walleriana
75. Toluic acid I. balsamina leaves, stems Chua, 2016
76. Vanillic acid I. balsamina flowers Kim et al., 2015
I. noli-tangere,
I. parviflora,
I. walleriana
77. Veratric acid I. glandulifera leaves Szewczyk and Olech, 2017
78. p-Hydroxybenzoic acid methyl ester I. balsamina flowers Kim et al., 2015
79. Caffeic acid I. balsamina leaves, stems Chua, 2016
I. parviflora leaves Bathe-Smith, 1962; Hromádková et al.,
2014
111
I. noli-tangere,
I. parviflora,
I. walleriana
I. glandulifera flowers
80. Cinnamic acid I. balsamina leaves Chua, 2016
I. glandulifera flowers Szewczyk and Olech, 2017
81.3-Hydroxycinnamic I. balsamina leaves Szewczyk and Olech, 2017
I. glandulifera flowers, leaves,
roots
I. noli-tangere leaves
85.2-O-(4- hydroxybenzoyl)-4-O-β-D-glucopyranosyl-6-hydroxyphenylacetic acid I. balsamina flowers Li et al., 2015b
86. methyl 2-O-(4-hydroxybenzoyl)-4-O-β-D-glucopyranosyl-6-hydroxyphenylacetate I. balsamina flowers Li et al., 2015b
87. ethyl 2-O-(4-hydroxybenzoyl)-4-O-β-D-glucopyranosyl-6-hydroxyphenylacetate I. balsamina flowers Li et al., 2015b
88. butoxy 2-O-(4-hydroxybenzoyl)-4-O-β-D-glucopyranosyl-6-hydroxyphenylacetate I. balsamina flowers Li et al., 2015b
89. butoxy 2-O-(4-hydroxybenzoyl)-4,6-dihydroxyphenylacetate I. balsamina flowers Li et al., 2015b
90.1,2-O-(4-dihydroxy-benzoyl)-2,4,6-trihydroxyphenylacetic acid I. balsamina flowers Li et al., 2015b
91.1,2-O-(4-dihydroxy-benzoyl)-2,4,6-trihydroxyphenylacetic acid I. balsamina flowers Li et al., 2015b
92. methyl 2-O-(4-hydroxybenzoyl)-2,4,6-trihydroxyphenylacetate I. balsamina flowers Li et al., 2015b
93.4-O-β-D-glucopyranosyl-2,6-dihydroxyphenylacetic acid I. balsamina flowers Li et al., 2015b
Table 2 (continued)

K. Szewczyk
94. Scopoletin I. balfourii, leaves Hegnauer, 1964

I. balsamina,
I. capensis,
I. elegantissima,
I. flaccida,
I. glandulifera,
I. herzogii,
I. oliveri,
I. pallida,
I. platypetala,
I. repens,
I. scabrida,
I. schlechteri,
I. sultani,
I. walleriana
I. balsamina leaves, stems Chua, 2016
I. balsamina root cultures Dawson and Holland, 1999;
Panichayupakaranant et al., 1995;
Sakunphueak et al., 2013
I. glandulifera roots Tříska et al., 2013
95. Coumarin I. balsamina leaves, stems Chua, 2016
96.4,4′-Biisofraxidin I. balsamina root cultures Panichayupakaranant et al., 1998
97. Fraxidin I. balsamina leaves, stems Chua, 2016
98. Isofraxidin I. balsamina root cultures Dawson and Holland, 1999;
Panichayupakaranant et al., 1995;
112
99. Glucosyl columbianetin I. balsamina leaves, stems Chua, 2016
100.2-Methoxy-1,4-naphthoquinone I. balsamina aerial parts Mori et al., 2011;
Yang et al., 2001
flowers Kim et al., 2015;
Li et al., 2015a
leaves Ding et al., 2008;
Wang et al., 2011
pods, roots, seeds Wang et al., 2011
root cultures Panichayupakaranant et al., 1995
stems Jiang et al., 2017;
Wang et al., 2011
I. glandulifera flowers Lobstein et al., 2001;
Mitchell et al., 2007;
Ortin and Evans, 2013
leaves Chapelle, 1974; Lobstein et al., 2001;
Ruckli et al., 2014
roots Cimmino et al., 2016;
Ruckli et al., 2014;
Tříska et al., 2013
seed pods Ortin and Evans, 2013
stems Cimmino et al., 2016;
Lobstein et al., 2001;
Ruckli et al., 2014
Table 2 (continued)

K. Szewczyk
101.2-Hydroxy-1,4-naphthoquinone I. balsamina leaves Chua, 2016; Clevenger, 1958;

root cultures Panichayupakaranant et al., 1995
stems Chua, 2016
Jiang et al., 2017
I. capensis flowering aerial Lobstein et al., 2001
parts
I. glandulifera leaves, stems and Lobstein et al., 2001
flowers
root tissues Ruckli et al., 2014
I. noli-tangere flowering aerial Lobstein et al., 2001
parts
I. pallida leaves Clevenger, 1958
I. parviflora flowering aerial Lobstein et al., 2001
parts
102.2,3-Dihydroxy-1,4-napthoquinone I. balsamina root cultures Sakunphueak et al., 2013
103. Balsaminolate I. balsamina corolla Oku and Ishiguro, 2002
104. Methylene-3,3′-bilawsone I. balsamina leaves Chua, 2016
I. balsamina root cultures Panichayupakaranant et al., 1995
105. Impatienolate I. balsamina corolla Oku and Ishiguro, 2002
106. Balsaminone A I. balsamina pericarp of the Ishiguro et al., 1998
fruit
I. balsamina seeds Pei et al., 2012
107. Balsaminone B I. balsamina flowers Li et al., 2015a
I. balsamina pericarp of the Ishiguro et al., 1998
113
fruit
I. balsamina seeds Pei et al., 2012
108. Balsaminone C I. balsamina seeds Pei et al., 2012
109. Balsaminone D I. balsamina flowers Li et al., 2015a
110. Balsaminone E I. balsamina flowers Li et al., 2015a
111.1α,2α-diol-4α-ethoxy-1,2,3,4-tetrahydronaphthalene I. balsamina stems Chen et al., 2010
112.1α,2α,4β-triol-1,2,3,4-tetrahydronaphthalene I. balsamina stems Chen et al., 2010
113. (3S, 4R)-3,4-dihydroxy-3,4-dihydronapthalen-1(2H)-one I. balsamina flowers Kim et al., 2015
114. trans-(3S, 4R)-3,4-dihydroxy-1-tetralone I. balsamina flowers Kim et al., 2015
115. Hydroquinone I. balsamina flowers Kim et al., 2015
116. Tyrosol I. balsamina flowers Kim et al., 2015
117.1,2,4-Trihydroxynaphthalene-1-O-glucoside I. balsamina aerial parts, roots Tříska et al., 2013
I. glandulifera
I. parviflora
118. Carboxyl lawsone I. balsamina leaves Chua, 2016
119. Hosenkoside A I. balsamina seeds Fu et al., 2012
Shoji et al., 1994a
120. Hosenkoside D I. balsamina seeds Fu et al., 2012
Shoji et al., 1994a
121. Hosenkoside J I. balsamina seeds Shoji et al., 1994b
122. Hosenkoside K I. balsamina seeds Fu et al., 2012
Shoji et al., 1994b
123. Hosenkoside L I. balsamina seeds Fu et al., 2012
Shoji et al., 1994c
124. Hosenkoside M I. balsamina seeds Fu et al., 2012
Shoji et al., 1994c
125. Hosenkoside B I. balsamina seeds Fu et al., 2012
Shoji et al., 1994a
Table 2 (continued)

K. Szewczyk
126. Hosenkoside E I. balsamina seeds Shoji et al., 1994a

127. Hosenkoside F I. balsamina seeds Fu et al., 2012
Shoji et al., 1994b
128. Hosenkoside H I. balsamina seeds Shoji et al., 1994b
129. Hosenkoside I I. balsamina seeds Shoji et al., 1994b
130. Hosenkoside C I. balsamina seeds Fu et al., 2012
Shoji et al., 1994a
131. Hosenkoside G I. balsamina seeds Fu et al., 2012
Shoji et al., 1994b
132. Hosenkoside N I. balsamina seeds Shoji et al., 1994c
133. Hosenkoside O I. balsamina seeds Shoji et al., 1994c
134. α-Amyrin caffeate I. balsamina seeds Lei et al., 2010b
135. Echinocystic acid I. balsamina root cultures Sakunphueak et al., 2013
I. pritzellii var. rhizomes Zhou et al., 2009a,b
hupehensis
136. Balsaminside A I. balsamina flowers Li et al., 2017
137. Balsaminside B I. balsamina flowers Li et al., 2017
138. Balsaminside C I. balsamina flowers Li et al., 2017
139. Balsaminside D I. balsamina flowers Li et al., 2017
140. β-D-glucopyranosiduronic acid, (3β)-norolean-3-yl-O-β-D-glucopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 4)] I. balsamina flowers Li et al., 2017
141.3-O-β-D-xylopyranosyl-(1 → 2)-β-D-glucopyranosyl-28-O-β-D-glucopyranosyl oleanolic acid I. balsamina flowers Li et al., 2017
142. α-Spinasterol I. balsamina leaves, roots, Wang et al., 2011
stems
I. glandulifera leaves, roots, Cimmino et al., 2016
stems
114
I. pritzellii Zhao et al., 2005a, 2005b
143. Glanduliferin A I. glandulifera stems Cimmino et al., 2016
144. Glanduliferin B I. glandulifera stems Cimmino et al., 2016
145. α-Spinasterol-3-O-β-D-glucopyranoside I. noli-tangere herb Choi and Kim, 2002
146. IPS-1 I. parviflora leaves Grabowska et al., 2017
147. IPS-2 I. parviflora leaves Grabowska et al., 2017
148. Spinasteryl-3-one I. pritzellii Zhao et al., 2005a, 2005b
149. α-Spinasteryl-3β-O-palmitate I. pritzellii Zhao et al., 2005a, 2005b
150.3-O-[6′-O-palmitoyl-β-D-glucosyl]-spinasterol I. pritzellii Zhao et al., 2005a, 2005b
151. Hentriacontane I. pritzellii Zhao et al., 2005a, 2005b
151.2′-Acetamido-3′-phenyl propyl 2-benzamido-3-phenyl propionate I. pritzellii Zhao et al., 2005a, 2005b
153.3-O-β-D-glucuronopyranosyl echinocystic acid I. pritzellii var. rhizomes Zhou et al., 2009a,b
hupehensis
154.3-O-[(6-O-methyl)-β-D-glucuronopyranosyl] echinocystic acid I. pritzellii var. rhizomes Zhou et al., 2009a,b
hupehensis
155.3-O-[(6-O-ethyl)-β-D-glucuronopyranosyl] echinocystic acid I. pritzellii var. rhizomes Zhou et al., 2009a,b
hupehensis
156.3-O-[(6-O-nbutyl)-β-D-glucuronopyranosyl] echinocystic acid I. pritzellii var. rhizomes Zhou et al., 2009a,b
hupehensis
157.3-O-[(6-O-n-butyl)-β-D-glucuronopyranosyl]-28-O-[β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl] echinocystic acid I. pritzellii var. rhizomes Zhou et al., 2009a,b
hupehensis
158. Impatienoside G I. siculifer whole plant Li et al., 2009
159.3-O-α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranosyl-soyasapogenol E I. siculifer whole plant Li et al., 2009
160. Soyasaponin Bg I. siculifer whole plant Li et al., 2009
161. Dehydrosoyasaponin I I. siculifer whole plant Li et al., 2009
162. Sandosaponin A I. siculifer whole plant Li et al., 2009
163. Soyasapogenol B monoglucuronide I. siculifer whole plant Li et al., 2009
164. Soyasaponin IV I. siculifer whole plant Li et al., 2009
165. Soyasaponin I I. siculifer whole plant Li et al., 2009
Table 2 (continued)

K. Szewczyk
166. Soyasaponin I methyl ester I. siculifer whole plant Li et al., 2009

167. Soyasaponin II I. siculifer whole plant Li et al., 2009
168. Impatienoside A I. siculifer whole plant Li et al., 2009
169.22-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-soyasapogenol A I. siculifer whole plant Li et al., 2009
170.3-O-α-L-arabinopyranosyl-(1 → 2)-β-D-glucuronopyranosyl-22-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-soyasapogenol A I. siculifer whole plant Li et al., 2009
171. Soyasaponin A1 I. siculifer whole plant Li et al., 2009
172. Impatienoside B I. siculifer whole plant Li et al., 2009
173. Impatienoside C I. siculifer whole plant Li et al., 2009
174. Impatienoside D I. siculifer whole plant Li et al., 2009
175. Impatienoside E I. siculifer whole plant Li et al., 2009
176. Impatienoside F I. siculifer whole plant Li et al., 2009
177. Parinaric acid I. edgeworthii seed oil Bagby et al., 1966
I. glandulifera seed oil Kaufmann and Keller, 1950
I. balsamina leaves, stems Chua, 2016
178. Glycerol 9(E),11(Z),13(E)-octadecatrienoyl ester I. balsamina flowers Li et al., 2017
179. Methyl linolenate I. balsamina root cultures Sakunphueak et al., 2013
180. Chavicol acetate I. balsamina leaves, stems Chua, 2016
181. Acetodiparinarine I. glandulifera seed oil Kaufmann and Keller, 1950
182. Glicerol I. glandulifera seed oil Kaufmann and Keller, 1950
183. Acetic acid I. glandulifera seed oil Kaufmann and Keller, 1950
184. Palmitic acid I. glandulifera seed oil Kaufmann and Keller, 1950
185. Stearic acid I. glandulifera seed oil Kaufmann and Keller, 1950;
flower stalks with Ortin and Evans, 2013
seed pods
I. pritzellii Zhao et al., 2005a
186. Linoleic acid I. glandulifera seed oil Kaufmann and Keller, 1950
115
187. Linolenic acid I. glandulifera flower stalks with Ortin and Evans, 2013
seed pods
188. Arachidic acid I. glandulifera flower stalks with Ortin and Evans, 2013
seed pods
189. trans-Tetradec-2-enoic acid I. glandulifera flower stalks with Ortin and Evans, 2013
seed pods
190. trans-Tetradec-2-enoic acid methyl ester I. glandulifera flower stalks with Ortin and Evans, 2013
seed pods
191. Balsamitril I. balsamina flowers Kim et al., 2015
192. Balsamitril-3-O-β-D-glucoside I. balsamina flowers Kim et al., 2015
193.8-Ethyl-10-hydroxyethyl lobelionol I. balsamina leaves, stems Chua, 2016
194.8-Ethyl-10-phenyllobelionol I. balsamina Chua, 2016
195. Scopoline I. capensis seeds Hegnauer, 1989
196. Hypaphorine I. niamniamensis seeds Chand et al., 2011
197.2′-Acetamido-3′-phenyl propyl 2-benzamido-3-phenyl propionate I. pritzellii var. rhizomes Zhao et al., 2005b
hupehensis
198. Soyacerebroside I I. pritzellii var. rhizomes Zhao et al., 2009
hupehensis
199. Soyacerebroside II I. pritzellii var. rhizomes Zhao et al., 2009
hupehensis
200. N-phenyl-2-naphthylamine I. siculifer Du and Xu, 1995
201.1-Chloro-hexadecane I. balsamina whole plant Zhou et al., 2014
202.2-Carbonyl-6,10-dimethy-5,9-undecadien I. balsamina whole plant Zhou et al., 2014
203.5,6,7,7α-Hydro-4,4,7α-trimethyl-tetr-2(4H)-benzofuranone I. balsamina whole plant Zhou et al., 2014
204.2-Sulfonamide naphthalene I. balsamina whole plant Zhou et al., 2014
205.6,10,14-Trimethyl-2-pentadecanone I. balsamina whole plant Zhou et al., 2014
206. Methyl hexadecanoate I. balsamina whole plant Zhou et al., 2014
207. Decyl-3,4-dimethyl-phenyl phthalic acid ester I. balsamina whole plant Zhou et al., 2014
208. [1,2,4]Triazolo [1,5-α]pyrimidine-6-carboxylic acid-4,7-dihydro-7-imino-ethyl ester I. balsamina whole plant Zhou et al., 2014
Table 2 (continued)

K. Szewczyk
209. N-Butyl-cis-4-cyclohexene-1,2-dicarboximide I. balsamina whole plant Zhou et al., 2014

210. [2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl]-1-piperazine I. balsamina whole plant Zhou et al., 2014
211. Eicosane I. balsamina whole plant Zhou et al., 2014 Zhou et al., 2014
212.1-Tricosane I. balsamina whole plant Zhou et al., 2014
213.2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene I. balsamina whole plant Zhou et al., 2014
214. Octadecane I. balsamina whole plant Zhou et al., 2014
215. trans-Methyl 13-octadecenoate I. bicolor Nisar et al., 2012
216. Methyl heptadecanoate I. bicolor Nisar et al., 2012
217. Methyl octadecanoate I. bicolor Nisar et al., 2012
218. Methyl docosanoate I. bicolor Nisar et al., 2012
219. Methyl tetracosanoate I. bicolor Nisar et al., 2012
220. Methyl eicosanoate I. bicolor Nisar et al., 2012
221. α-Terpinyl acetate I. glandulifera herb Szewczyk et al., 2016a
222. Phellandral I. glandulifera herb Szewczyk et al., 2016a
223. (Z)-Ligustilide I. glandulifera herb Szewczyk et al., 2016a
224. (Z)-Butylidenphthalide I. glandulifera herb Szewczyk et al., 2016a
225. Butylphthalide I. glandulifera herb Szewczyk et al., 2016a
226. β-Phellandrene I. glandulifera herb Szewczyk et al., 2016a
227. Vulgarone B I. glandulifera roots Szewczyk et al., 2016a
228. Linalool I. glandulifera herb, roots Szewczyk et al., 2016a
I. parviflora herb, roots
229. Borneol I. glandulifera herb, roots Szewczyk et al., 2016a
230. Bornyl acetate I. glandulifera herb, roots Szewczyk et al., 2016a
231. Pentadecanal I. glandulifera herb, roots Szewczyk et al., 2016a
232. β-Barbatene I. glandulifera herb, roots Szewczyk et al., 2016a
233. Hexanal I. glandulifera herb, roots Szewczyk et al., 2016a
116
234. Heptanal I. glandulifera herb, roots Szewczyk et al., 2016a
235. Nonanal I. glandulifera herb, roots Szewczyk et al., 2016a
236. Benzaldehyde I. glandulifera herb, roots Szewczyk et al., 2016a
I. parviflora herb
237. Terpinene-4-ol I. glandulifera herb, roots Szewczyk et al., 2016a
238. α-Terpineol I. glandulifera herb, roots Szewczyk et al., 2016a
239. β-Ionone I. glandulifera herb, roots Szewczyk et al., 2016a
240. δ-Cadinene I. glandulifera herb, roots Szewczyk et al., 2016a
241. (E)-Hex-3-en-1-ol I. parviflora herb Szewczyk et al., 2016a
242. Citronellol I. parviflora roots Szewczyk et al., 2016a
243. Geranial I. parviflora roots Szewczyk et al., 2016a
244. Hexahydrofarnesyl acetone I. balsamina herb Szewczyk et al., 2016a
245. Dodecanoic acid I. balsamina herb Szewczyk et al., 2016a
246. (Z)-Hex-3-enol I. noli-tangere herb Szewczyk et al., 2016a
247. Glucose I. balsamina aerial parts Szewczyk et al., 2018
I. balsamina roots Szewczyk et al., 2018
I. balsamina seeds Earle and Jones, 1962
I. glandulifera aerial part Szewczyk et al., 2018
roots
I. noli-tangere aerial parts Szewczyk et al., 2018
roots
Table 2 (continued)

K. Szewczyk
248. Galactose I. balsamina aerial parts Szewczyk et al., 2018

roots
roots
249. Xylose I. balsamina aerial parts Szewczyk et al., 2018
roots
roots
250. Planteose I. balsamina seeds Gurusinghe and Bradford, 2001
251. α-D-Glucopyranosyl-(1 → 1′)-3′-amino-3′-deoxy-β-D-glucopyranoside I. balsamina flowers Li et al., 2017
252. Arabinose I. balsamina aerial parts, roots Szewczyk et al., 2018
I. glandulifera aerial parts, roots Szewczyk et al., 2018
I. noli-tangere aerial parts, roots Szewczyk et al., 2018
aerial parts, roots Szewczyk et al., 2018
253. Mannose I. balsamina aerial parts, roots Szewczyk et al., 2018
117
254. Rhamnose I. balsamina aerial parts, roots Szewczyk et al., 2018
255. Galacturonic acid I. balsamina, aerial parts, roots Szewczyk et al., 2018
I. glandulifera,
I. noli-tangere
256. Fucose I. parviflora leaves Hromádková et al., 2014
257. Methylglucuronoxylan I. parviflora leaves Hromádková et al., 2014
258. Arabinogalactan I. parviflora leaves Hromádková et al., 2014
259.2-Amino-2-deoxy-D-glucose I. pritzellii rhizomes Zhou et al., 2007a,b
260. Aspartic acid I. balsamina fruit pericarp Pal and Biswas, 1994
261. Glutamic acid I. balsamina fruit pericarp Pal and Biswas, 1994
262. Tyrosine I. balsamina fruit pericarp Pal and Biswas, 1994
263. Leucine I. balsamina fruit pericarp Pal and Biswas, 1994
264. Glycine I. balsamina fruit pericarp Pal and Biswas, 1994
265. Proline I. balsamina fruit pericarp Pal and Biswas, 1994
266. Serine I. balsamina fruit pericarp Pal and Biswas, 1994
267. Aminobutyric acid I. balsamina leaves, stems Chua, 2016
268. Valine I. balsamina leaves, stems Chua, 2016
269. Pyroglutamic acid I. balsamina leaves, stems Chua, 2016
270. Alanyl alanine I. balsamina leaves, stems Chua, 2016
271. Hydroxyglycyl glycine I. balsamina leaves, stems Chua, 2016
272. Hydroxytryptophan I. balsamina leaves, stems Chua, 2016
273. Glutaryl deoxyalanyl alanine I. balsamina leaves, stems Chua, 2016
274. Glutaryl alanylalanine I. balsamina leaves, stems Chua, 2016
Table 2 (continued)

K. Szewczyk
275. Isoleucine I. balsamina leaves Chua, 2016

276. Hydroxylysine I. balsamina leaves Chua, 2016
277. Phenylalanine I. balsamina leaves Chua, 2016
278.1-Deoxy-1-fructosyl isoleucine I. balsamina leaves Chua, 2016
279. Caffeoyl leucine I. balsamina leaves Chua, 2016
280. Glyceric acid I. balsamina leaves, stems Chua, 2016
281. Fumaric acid I. balsamina leaves, stems Chua, 2016
282. Succinic acid I. balsamina leaves, stems Chua, 2016
283. Tartronic acid I. balsamina leaves, stems Chua, 2016
284. Malic acid I. balsamina leaves, stems Chua, 2016
285. Hydroxyterpenylic acid I. balsamina leaves, stems Chua, 2016
286. Gluconic acid I. balsamina leaves, stems Chua, 2016
287. Lauric acid I. balsamina leaves, stems Chua, 2016
288. Trihydroxyl caffeic acid I. balsamina leaves, stems Chua, 2016
289. Glutamine I. capensis leaves, stems Lanza et al., 1995
290. Hydroxyproline I. capensis leaves, stems Lanza et al., 1995
291.6-O-(E)-p-hydroxy-cinnamoyl-β-D-glucose I. balsamina flowers Li et al., 2017
292.6-O-(E)-p-hydroxy-cinnamoyl-α-D-glucose I. balsamina flowers Li et al., 2017
293. Autantiamide acetate I. balsamina flowers Li et al., 2017
294. Cryptoxanthin I. noli-tangere Kleinig and Nietsche, 1968;
Nitsche and Pleugel, 1972
295. Neoxanthin I. noli-tangere Kleinig and Nietsche, 1968;
296. Cryptoxanthin epoxide I. noli-tangere Kleinig and Nietsche, 1968;
297. Violaxanthin I. noli-tangere flowers Wrischer et al., 1999
118
298. Lutein epoxide I. noli-tangere flowers Wrischer et al., 1999
299. Ib-AMP1 I. balsamina seeds Tailor et al., 1997
who found the intense yellow of the petals originates from unipolar plants in the pharmacology, food or cosmetic industries. Albeit, issues
carotenoids [(violaxanthin (297, MW = 600), lutein epoxide (298, relating to the variability of essential oil composition should be re-
MW = 584)] that accumulate in large quantities in chromoplasts. (see solved.
Fig. 72). The data in this review indicates that there are comprehensive
Many authors demonstrated the presence of low molecular weight studies concerning the chemical composition of different Impatiens
polypeptides (LMW) in I. balsamina (Fan et al., 2013; Fan et al., 2013a; species. However, phytochemical studies on more taxa are needed to
Fan et al., 2018; Tailor et al., 1997; Thevissen et al., 2005). Tailor et al., confirm the possibility of using these compounds as chemotaxonomic
1997 isolated four [(Ib-AMP1 (299, MW = 2464), Ib-AMP2 (300, markers.
MW = 2527), Ib-AMP3 (301, MW = 2536), and Ib-AMP4 (302,
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Biochemical Systematics and Ecology 80 (2018) 94–121

Contents lists available at ScienceDirect

Biochemical Systematics and Ecology

Phytochemistry of the genus impatiens (Balsaminaceae): A review T

E-mail address: k.szewczyk@umlub.pl.

Fig. 3. Chemical structure of compound 18 (R = H; MW = 732) and 19

Fig. 4. Chemical structure of compound 20 (R = H; MW = 732) and 21

Fig. 1. Kaempferol and kaempferol O-glycosides.

27 Impatiens species. In the phytochemically studied species, the fol-

Phytochemical investigations of Impatiens species have led to the

Fig. 5. Quercetin and derivatives.

Hagen (1966) reported that stems of I. balsamina (genotype

Fig. 10. Chemical structure of compound 51 (MW = 432).

Fig. 7. Chemical structure of compound 45 (R = H; MW = 318) and 46 (R = β-

Fig. 11. Anthocyanidins.

Fig. 8. Apigenin and O-glucoside.

using repeated column chromatography and semi-preparative HPLC (Li

I. balfourii Hook.f. (or I. insignis + + + + + +

Fig. 19. Coumarins.

Fig. 17. Depside derivatives.

Fig. 20. Chemical structure of compound 99 (MW = 408).

methanol (50:50,v/v) extract of I. balsamina root cultures 2,3-dihy-

Fig. 29. Chemical structure of compound 113 (R = α-OH; MW = 178) 114

Fig. 30. Chemical structure of compound 115 (MW = 110).

Fig. 31. Chemical structure of compound 116 (MW = 138).

Fig. 32. Chemical structure of compound 117 (MW = 338).

Fig. 34. Chemical structure and molecular weight of hosenkosides 125–129;

Fig. 33. Chemical structure and molecular weight of hosenkosides 119–124;

Fig. 37. Chemical structure of compound 135 (MW = 472).

Fig. 41. Chemical structure of compound 143 (MW = 632).

Fig. 38. Chemical structure and molecular weight of balsaminsides.

Fig. 42. Chemical structure of compound 144 (MW = 616).

Fig. 43. Chemical structure of compound 145 (MW = 574).

Fig. 44. Chemical structure of compound 146 (R = COCH3; MW = 1017) and

(Grabowska et al., 2017).

Fig. 46. Chemical structure of compound 149 (MW = 651).

Fig. 47. Chemical structure of compound 151 (MW = 436).

Fig. 49. Chemical structure and molecular weight of triterpenoid saponins

Fig. 48. Chemical structure and molecular weight of compounds 153–158.

et al., 2005a, 2005b).

Fig. 51. Chemical structure of compound 177 (MW = 276).

Fig. 52. Chemical structure of compound 178 (MW = 352).

Fig. 53. Chemical structure of compound 179 (MW = 292).

Fig. 54. Chemical structure of compound 180 (MW = 176).

glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-soyasapogenol A (170),

2.6. Fatty acids Fig. 55. Chemical structure of fatty acids.

According to Kaufmann and Keller (1950), the Impatiens species

Fig. 59. Chemical structure of compound 196 (MW = 246).

Fig. 64. Chemical structure of compound 256 (MW = 341).

Fig. 65. Chemical structure of compound 258 (MW = 500).

Fig. 66. Chemical structure of compound 259 (MW = 179).

Asan, Korea. Their structures were established as balsamitril (191) and

Fig. 62. Chemical structure of sugars.

Using optimal supercritical extraction Zhou et al. (2014) identiﬁed

Fig. 67. Chemical structure of amino acids.

Fig. 71. Chemical structure of compound 293 (MW = 444).

octadecanoate (217, MW = 298), methyl docosanoate (218,

(Gurusinghe and Bradford, 2001).

2.10. Amino acids and amino derivatives

A high molecular weight protein has been isolated as a major

Constituent name Species Part of plant References

1. Kaempferol I. capensis ﬂowers Clevenger, 1958

Constituent name Species Part of plant References

22. Kaempferol O-rhamno-O-hexoside I. balfourii aerial parts Szewczyk et al., 2016b