ArticlePDF Available

Abstract and Figures

Fireweed (Epilobium angustifolium L., Onagraceae) is one of important medicinal plants used especially in the treatment of urogenital disorders, including benign prostatic hyperplasia (BPH) and prostatitis. The therapeutic effects of E. angustifolium extracts comprise antiproliferative, anti-inflammatory, immunomod-ulatory, antioxidant, and also antimicrobial activities. The aim of the present review was to provide the information on the botany, phytochemistry and traditional uses of E. angustifolium. This plant is a widespread circumboreal species of North America and Eurasia, tolerant in terms of habitat conditions, and often occupying man-made open habitats. Phytochemical studies on E. angustifolium resulted in the identification of about 250 different metabolites, including about 170 substances found for the first time in this plant in the last six years (2014-2019). Fireweed has an abundance of polyphenolic compounds, particularly ellagi-tannins. Oenothein B and quercetin-3-O-glucuronide are proposed as markers for the identification and standardization of the plant raw material. E. angustifolium exhibits significant phytochemical variability in relation to the geographical origin, plant part and time of harvest/vegetation phase. Survey of the ethnobo-tanical literature showed that the above-mentioned species has been widely used not only as a medicinal, but also as an edible, honey and decorative plant. botanical part, we described taxonomy, synonyms, and also morphology, ploidy, distribution and habitats of fireweed. The phytochemistry included the composition of the bioactive substances found in the plant raw material, with particular emphasis on the newly identified metabolites and with the description of the phytochemical variability of this species. In turn, the ethnobotanical characteristic aimed to present the traditional uses of E. angustifolium as a medicinal, edible, honey and decorative plant.
Content may be subject to copyright.
Vol. 65 No. 3 2019
International journal edited by the Institute of Natural Fibres and Medicinal Plants
DOI: 10.2478/hepo-2018-000
DOI: 10.2478/hepo-2018-000
REVIEW PAPER
Herba Pol 2019; 65(3): 51-63
Fireweed (Epilobium angustifolium L.): botany,
phytochemistry and traditional uses. A review
ARTUR ADAMCZAK1*, MARIOLA DREGER2, KATARZYNA SEIDLERŁOŻYKOWSKA1,
KAROLINA WIELGUS2
1Department of Botany, Breeding and Agricultural Technology of Medicinal Plants
Institute of Natural Fibres and Medicinal Plants
Kolejowa 2
62-064 Plewiska, Poland
2Department of Biotechnology
Institute of Natural Fibres and Medicinal Plants
Wojska Polskiego 71B
60-630 Poznań, Poland
*corresponding author: phone: +48 (61) 665-95-50, e-mail: artur.adamczak@iwnirz.pl
Summary
Fireweed (Epilobium angustifolium L., Onagraceae) is one of important medicinal plants used especially in
the treatment of urogenital disorders, including benign prostatic hyperplasia (BPH) and prostatitis. The
therapeutic effects of E. angustifolium extracts comprise antiproliferative, anti-inflammatory, immunomod-
ulatory, antioxidant, and also antimicrobial activities. The aim of the present review was to provide the in-
formation on the botany, phytochemistry and traditional uses of E. angustifolium. This plant is a widespread
circumboreal species of North America and Eurasia, tolerant in terms of habitat conditions, and often oc-
cupying man-made open habitats. Phytochemical studies on E. angustifolium resulted in the identification
of about 250 different metabolites, including about 170 substances found for the first time in this plant in
the last six years (2014–2019). Fireweed has an abundance of polyphenolic compounds, particularly ellagi-
tannins. Oenothein B and quercetin-3-O-glucuronide are proposed as markers for the identification and
standardization of the plant raw material. E. angustifolium exhibits significant phytochemical variability in
relation to the geographical origin, plant part and time of harvest/vegetation phase. Survey of the ethnobo-
tanical literature showed that the above-mentioned species has been widely used not only as a medicinal, but
also as an edible, honey and decorative plant.
Received: 2019-08-01
Accepted: 2019-09-20
Available online: 2019-09-30
DOI: 10.2478/hepo-2019-0018
52 A. Adamczak, M. Dreger, K. Seidler-Łożykowska, K. Wielgus
botanical part, we described taxonomy, synonyms,
and also morphology, ploidy, distribution and habi-
tats of reweed. e phytochemistry included the
composition of the bioactive substances found in the
plant raw material, with particular emphasis on the
newly identied metabolites and with the descrip-
tion of the phytochemical variability of this species.
In turn, the ethnobotanical characteristic aimed to
present the traditional uses of E. angustifolium as a
medicinal, edible, honey and decorative plant.
BOTANY
Taxonomy
Epilobium (Chamerion) angustifolium is classied to
the Onagraceae family, which consists of 22 genera
and approximately 650 species. e genus Chamer-
ion (Raf.) Raf. ex Holub (syn. Chamaenerion Ség.)
with eight species restricted to the northern hemi-
sphere (mainly in Eurasia) belongs to the Onagroi-
deae subfamily and Epilobieae tribe [18]. Relatively
oen, it is included in Epilobium L., which is the
largest genus in the Onagraceae [19-22]. However,
Chamerion clearly diers from Epilobium in terms
of ower structure, leaf arrangement and other
features [18, 23-25]. Molecular data also show that
Chamerion is a separate monophyletic group of
plants [26-28].
Synonyms
e Plant List [22] provides more than 40 synonyms
of the species described, with three of these being the
most commonly used: Epilobium angustifolium L.,
Chamerion angustifolium (L.) Holub and Chamae-
nerion angustifolium (L.) Scop. According to Holub
[23], Chamerion should be considered the correct
Latin name of this genus, while Chamaenerion is
an illegitimate name. On the other hand, Sennikov
[25] recently presented arguments for the restora-
tion of the older name Chamaenerion. However, in
INTRODUCTION
Nowadays, the consumption of herbal products and
the popularity of dietary supplements are growing
throughout the world. Nutraceuticals or functional
foods are intended to improve the state of health and
well-being and to reduce the risk of nutrition-asso-
ciated diseases, including cancer prevention. Fire-
weed (Epilobium angustifolium L.) is an important
medicinal plant used in the pharmaceutical, food
and cosmetic industries. It is particularly utilized
in the treatment of benign prostatic hyperplasia
(BPH) and prostatitis [1]. Today, dietary supple-
ments or nutraceuticals containing E. angustifolium
components are widely available in many countries
in the form of tea, capsules, pills, water and alcohol
extracts/tonics. Fireweed extracts are also utilized
in creams, shampoos and other cosmetic products,
especially for acne.
E. angustifolium is a rich source of phenolic com-
pounds, especially hydrolysable tannins (ellagitan-
nins), avonoids, and phenolic acids [2-4]. Medici-
nal properties of reweed extracts have been attrib-
uted to the synergic eect of polyphenols and the
presence of the most abundant, compound – oeno-
thein B. is substance shows various pharmacolog-
ical activities, including anti-androgenic, antiprolif-
erative, anticancer, antioxidant, anti-inammatory,
and immunomodulatory properties [5-10]. Addi-
tionally, E. angustifolium exhibits antimicrobial [11-
15], analgesic [16] as well as photoprotective and
antiaging [17] activities.
Recently, the number of publications concerning
the above-mentioned species has increased signi-
cantly. Screening of the Scopus database with the
keywords of 'Epilobium/Chamerion/Chamaenerion
angustifolium' found 416 document results, includ-
ing 80 articles published in the years of 2014–2019.
A new detailed summary is required not only for
phytochemistry and pharmacology of E. angustifoli-
um, but also in the case of scattered data on reweed
botany and ethnobotany.
e aim of the study was to provide an overview
of information available on the botany, phytochem-
istry and traditional uses of E. angustifolium. In the
Key words: rosebay willowherb, phytochemical composition and variability, ellagitannins, oenothein B,
ethnobotany
Słowa kluczowe: wierzbówka kiprzyca, skład i zmienność fitochemiczna, elagotaniny, oenoteina B,
etnobotanika
53
Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review
Vol. 65 No. 3 2019
subentire margin, and glabrous abaxial midribs,
as well as subglabrous stems and usually triporate
pollen. e polyploid plants of subsp. circumvagum
(n=36, 54) are generally luxuriant with taller stems,
larger leaves, owers and pollen. ey have leaves
with petioles 2–7 mm long, a cuneate base, denticu-
late margin, glabrous to very pubescent midribs, as
well as strigillose stems, at least in the upper section,
while pollen is usually a mixture of triporate and
quadriporate grains [36, 37].
Distribution and habitats
E. angustifolium is a widespread circumboreal spe-
cies occurring in the temperate zone of North Amer-
ica and Eurasia at a latitude from 25o to 70o north. It
grows both in the lowlands and in the mountains: in
Switzerland to 2530 m, in North America to 3960 m,
and in the Himalayas to an altitude of 4850 m a.s.l.
Diploid populations occur in colder climates: in
Greenland, Canada, Alaska, Siberia and northern
Europe, and also tend to develop at higher altitudes.
Tetraploids grow in warmer and drier habitats oc-
cupying the southern part of the range in Eurasia
and North America [18, 38, 39]. In turn, triploids
(n=27) appear in mixed-ploidy populations of bor-
der areas [40]. e hexaploid cytotype was reported
only in central Japan and the Yunnan province of
China [36, 41].
Fireweed is a common plant occupying man-
made open habitats, such as deforested or burned
this review, the name appearing most frequently in
the references will be used: Epilobium angustifolium.
E. angustifolium is commonly known as reweed
in the United States and rosebay willowherb in Brit-
ain [25]. Other names mentioned include: peren-
nial reweed, narrow-leaved reweed, great willow-
herb, willow herb, owering willow, French willow,
etc. [29, 30].
Morphology and ploidy
Fireweed is an herbaceous perennial with long
branched rhizomes and eshy stolons. Green stems,
frequently reddish, glabrous below and pubescent
above, are erect up to 2 m high. e willow-like
leaves are alternate, 3–20 cm long. E. angustifolium
blooms from June to September, developing large
raceme inorescences consist of a number of pink
(rarely white) owers (gure 1). ey are up to 3 cm
in diameter, zygomorphic, epigynous with a small
nectar-secreting disc, markedly protandrous. e
capsules, 4–8 cm long, contain small light brown
seeds (1.0–1.3 mm in length) with greyish white
hairs up to 13 mm long. One plant could produce
76 000 wind-dispersed seeds per year [31-33]. e
weight of 1 000 seeds is about 0.07 g [34] and with-
out the pappus reaches about 0.05 g [35].
E. angustifolium is a variable species diverse in
terms of morphology and ploidy. e diploid rep-
resenting subsp. angustifolium (n=18) has sub-
sessile leaves with an obtuse or subrounded base,
Figure 1
Epilobium angustifolium in the blooming phase (Krajewice, Poland)
54 A. Adamczak, M. Dreger, K. Seidler-Łożykowska, K. Wielgus
areas, roadsides and railway embankments. is
species also occurs on the edge of forests and thick-
ets, along streams, on rocky and scree slopes, as well
as in mountain meadows. E. angustifolium prefers
nutrient-rich and mesic-moist soils, but it is tolerant
in terms of habitat conditions [31-33, 36].
PHYTOCHEMISTRY
Chemical composition
Phytochemical studies on E. angustifolium result-
ed in the identication of about 250 dierent me-
tabolites, of which about 170 substances have been
found for the rst time in this plant in the last six
years [2, 3, 8, 42-50] (table 1). Polyphenols are the
most abundant and are represented by avonoids,
phenolic acids, and hydrolysable tannins (ellagitan-
nins). Other constituents such as lignans, steroids,
triterpenoids, fatty acids, and essential oils, have
also been identied. e structures of some bioac-
tive compounds are given in gures 2 and 3.
Flavonoids
About 50 dierent avonoids and their derivatives
have been identied in reweed extracts. ey in-
clude avonol aglycones: kaempferol, quercetin and
myricetin, which contain a single sugar moiety of
glucuronic acid, rhamnose, glucose, arabinose or
galactose. Quercetin-3-O-glucuronide is the most
dominant and characteristic avonoid of E. angus-
tifolium, contrary to myricetin-3-O-rhamnoside
(myricitrin), which is the main avonoid of the
other Epilobium species [51]. Recently, avonol gly-
coconjugates acylated with hydroxycinnamic acids
were also detected [50].
Phenolic acids
Phenolic acids and their derivatives are one of the
dominant groups of phenolics found in E. angus-
tifolium, and are important contributors to the
antioxidant [48] and therapeutic potential against
BPH of this species [49]. A great variety of these
compounds, including 39 substances (e.g., caeic,
ellagic, ferulic, gallic, protocatechuic acids and caf-
feoylquinic acid isomers), has been found in the
reweed [8, 43, 48-50].
Hydrolysable tannins
E. angustifolium contains a high level of ellagitan-
nins, which represent about 15% of the dry mass of
the herb [2]. Ellagitannins are bioactive polyphe-
nols belonging to the class of hydrolysable tannins,
characterized as hexahydroxydiphenoyl (HHDP)
esters of sugar, mainly glucose. Both monomeric
(e.g., tellimagrandin I, gemin D) and macrocyclic
ellagitannins have been isolated from E. angusti-
folium herb [2, 3]. Oenothein B is a dimer which
includes two molecules of tellimagrandin I mono-
mers. Other macrocyclic ellagitannins – oenothein
A (trimer) and larger ellagitannins up to heptam-
ers were also detected and characterized using
the UPLC-MS/MS method [2]. Oenothein B is a
principal bioactive compound and the most abun-
dant ellagitannin, whose content ranges up to 50%
of the total mass of oligomeric ellagitannins in the
extract [2]. Depending on the plant origin and
harvest time, oenothein B concentration in the raw
material varies from 2 to 4.5% [50, 52, 53]. is
compound has been considered to be the main
contributor to the anti-androgenic, antiprolifera-
tive and anticancer, antioxidant, anti-inammato-
ry as well as antimicrobial eects of E. angustifo-
lium extracts [4]. erefore, analysis of oenothein
B and quercetin-3-O-glucuronide contents is rec-
ommended to provide markers and a basis for the
plant raw material standardization [4, 6, 43, 51].
Lignans
Recently, phytochemical analyses of ethyl acetate
and n-butanol extracts obtained from the aerial
parts of E. angustifolium resulted in the identica-
tion of ve lignans, including pinoresinol and its
derivatives, and salicifoliol. However, these com-
pounds did not show the anti-BPH activity [49].
Steroids, terpenoids and fatty acids
Besides polyphenols, the aerial parts of E. angusti-
folium contain a lipophilic fraction rich in steroids,
terpenoids and fatty acids. e presence of campes-
terol, cholesterol, stigmasterol as well as β-sitosterol
and its derivatives was reported [49, 50, 54-56]. Fat-
ty acids (41 identied compounds) as well as triter-
penes (e.g., oleanolic, pomolic and ursolic acids) are
the main components of the lipophilic fraction of
E. angustifolium extracts [42].
55
Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review
Vol. 65 No. 3 2019
Figure 2
Chemical structures of tellimagrandin I (a), oenothein B (b), and oenothein A (c)
56 A. Adamczak, M. Dreger, K. Seidler-Łożykowska, K. Wielgus
Figure 3
Chemical structures of quercetin-3-O-glucuronide (a), myricetin-3-O-rhamnoside (b), kaempherol-3-O-arabinoside (c), caeic acid
(d), ellagic acid (e), 3-O-caeoylquinic acid (f), 5-O-caeoylquinic acid (g), campesterol (h) cholesterol (i), and β-sitosterol (j)
57
Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review
Vol. 65 No. 3 2019
Group of
compounds Compounds
Flavonoids Annulatin-O-arabinoside*, annulatin-O-glucoside*, annulatin-O-rhamnoside*
Kaempferol, kaempferol-3-O-arabinoside (juglalin), kaempferol-3-O-glucoside*, kaempferol-7-O-p-
coumaroylglucoside*, kaempferol-3-O-(6''-p-coumaroyl)-glucoside, kaempferol-3-O-glucuronide, kaempferol-7-O-
glucuronide*, kaempferol-3-O-rhamnoside, kaempferol-7-O-rhamnoside*, kaempferol-3-O-rhamnopyranoside*,
kaempferol-3-O-galloylhexoside*, kaempferol 8-O-methyl ether, kaempferol-3-O-[6"-(E)-p-coumaroyl]-
mannopyranoside*
Myricetin, myricetin-3-O-arabinoside, myricetin-3-O-galactoside, myricetin-3-O-galactopyranoside*, myricetin-
3-O-glucoside (isomyricitrin), myricetin-7-O-glucoside*, myricetin-3,5-O-diglucoside*, myricetin-3-O-
caeoylglucoside*, myricetin-3-O-glucuronide, myricetin-3-O-rhamnoside (myricitrin), myricetin-3-O-pentoside*,
myricetin-3-O-hexoside*, myricetin-3-O-galloylhexoside*
Quercetin, quercetin-3-O-arabinoside (guajaverin), 3-O-methylquercetin-O-arabinoside*, quercetin-3-O-
arabinofuranoside (avicularin)*, quercetin-3-O-galactoside (hyperoside), quercetin-3-O-(6''-galloyl)-galactoside,
quercetin-3-O-glucoside (isoquercetin), quercetin-7-O-glucoside*, quercetin-7-O-caeoylglucoside*, quercetin-
caeoylhexoside*, quercetin-7-O-p-coumaroylglucoside*, quercetin-3-O-p-coumaroylhexoside*, quercetin-3-
O-feruloylglucoside*, quercetin-7-O-[galloyl]-glucoside*, quercetin-O-[digalloyl]-glucoside*, quercetin-3-O-
galloylhexoside*, quercetin-3-O-glucuronide (miquelianin), quercetin-3-O-glucuronide-6''-methyl ester*, quercetin
3-O-(6”-n-butyl glucuronide)*, quercetin-3-O-rhamnoside (quercitrin), quercetin-7-O-rhamnoside*, quercetin-3-
O-rutinoside (rutin)*
Phenolic acids and
their derivatives Benzoic acid*, 3-hydroxy-4-methoxybenzoic acid*, 3,4-dihydroxybenzoic acid (protocatechuic acid),
protocatechuic acid methyl ester*, 4-glucosyloxy-3-hydroxybenzoic acid*, p-hydroxybenzaldehyde*, methyl
p-hydroxy benzeneacetate*, benzyl 1-O-glucopyranoside*, caeic acid, digalloyl caeic acid*, cinnamic acid,
p-hydroxycinnamic acid (p-coumaric acid)*, p-hydroxycinnamic methyl ester*, ellagic acid, ferulic acid,
gallic acid, digallic acid*, methyl gallate*, octyl gallate, gentisic acid, 3-O-caeoylquinic acid (chlorogenic
acid), 4-O-caeoylquinic acid (cryptochlorogenic acid)*, 5-O-caeoylquinic acid (neochlorogenic acid),
4-O-caeoylquinic acid methyl ester*, ethyl 4-O-caeoylquinate*, methyl chlorogenat*, 3-O-p-coumaroylquinic
acid, 4-O-p-coumaroylquinic acid, 5-O-p-coumaroylquinic acid, 5-O-coumaroylquinic acid methyl ester*,
3-O-feruloylquinic acid, 5-O-feruloylquinic acid, 3-O-feruloylquinic acid methyl ester*, galloylshikimic acid*,
syringoylquinic acid*, valoneic acid dilactone, valoneic acid dilactone methyl ester*, 1'-monodecarboxyvaloneic acid
dilactone*, vanillic aldehyde*
Hydrolysable
tannins 1,6-di-O-Galloylglucose*, 1,2,6-tri-O-galloylglucose, 1,4,6-tri-O-galloylglucose*, 1,2,3,6-tetra-O-galloylglucose,
1,2,3,4,6-penta-O-galloylglucose, 1,2,6-tri-O-galloyl-4,6-HHDP-glucose, 2,3-di-O-galloyl-4,6-HHDP-glucose,
β-glucogallin*, digalloylglucose* and its isomer*, galloylconiferolglucose*, digalloylrhamnoside*, gemin D* and its
isomer*, isostrictinin*, oenothein A* and B, oxidized oenothein A derivative*, pedunculagin*, tellimagrandin I* and
II*, tellimagrandin I oligomers* from tetramer to heptamer
Lignans* Pinoresinol, pinoresinol-4-O-glucopyranoside, 4-ketopinoresinol, salicifoliol,
(7R, 8S)-3,5'-dimethoxy-4',7-epoxy-8,3'-neolignane-5,9,9'-triol
Steroids Campesterol, cholesterol, β-sitosterol, β-sitosterol caprate, β-sitosterol capronate, β-sitosterol caprylate, β-sitosterol
glucoside (daucosterol), β-sitosterol (6"-O-acetyl)-glucoside, β-sitosterol palmitate, β-sitosterol propionate,
stigmasterol
Triterpenes Betulinic acid*, corosolic acid, maslinic acid, oleanolic acid, acetyl oleanolic acid*, oleanonic acid*, pomolic acid*,
ursolic acid, acetyl ursolic acid*, ursonic acid*, urs-12-ene-2α,3-diol*
Fatty acids Arachic acid*, arachidic acid, behenic acid, capric acid, caproic acid, caprylic acid, cerotic acid, tricosanic acid*,
tetracosanic acid*, pentacosanic acid*, hexacosanic acid*, heptacosanic acid*, octacosanic acid*, nonacosanic
acid*, heneicosanic acid*, 2-hydroxytricosanic acid*, 2-hydroxytetracosanic acid*, 2-hydroxyhexacosanic acid*,
2-hydroxyoctacosanic acid*, pentadecanoic acid*, nonadecanoic acid*, hexadecanedioic acid*, octadecanedioic
acid*, pentadecenic acid*, triacontanic acid*, 2-hydroxytriacontanic acid*, eicosenoic acid, eicosandioic acid*, lauric
acid, lignoceric acid, linoleic acid, α-linolenic acid, γ-linolenic acid*, margaric acid*, melissic acid, montanic acid,
myristic acid, oleic acid, palmitic acid, palmitoleic acid*, stearic acid
Essential oil* ε-Amorphene, anethole, cis-anethole, trans-anethole, dihydroapofarnesal, cis-arbusculone, benzyl alcohol,
β-bisabolene, β-bourbonene, γ-cadinene, δ-cadinene, α-caryophyllene, β-caryophyllene, α-copaene, β-cubebene,
decanal, tridecane, tetradecane, n-decane, 2,6-dimethyl-7-octen-4-one, n-dodecane, γ-elemene, estragole, eugenol,
trans-α-farnesene, n-hexadecanol, trans-2-hexenal, cis-3-hexenol, cis-3-hexenyl hexanoate, cis-3-hexenyl pentanoate,
β-ionone, isogermacrene D, isopentyl butyrate, 3-methylbutyl-2-methylbutyrate, 2-methyl-cis-3-hexenylbutanoate,
cis-3-hexenyl isobutanoate, cis-3-hexenyl butyrate, linalool, pelargol, menthol, nonanal, cis-3-hexenol propanoate,
cis-3-hexen-1-yl-2-methylcrotonate, phenethyl alcohol, phenylacetaldehyde, dihydromyrcenol, tetrahydrofurfuryl
propionate, γ-terpinen-7-al, vomifoliol
Others Abscisic acid*, L-ascorbic acid, 2-hydroxybenzothiazole*, 1H-indole-3-carboxylic acid methyl ester*, ceryl alcohol,
chamaenerolide A*, charenol, chanerozan, choline, excavatine B*, benzofuran-2-carboxaldehyde*, 5-hydroxymethyl-
2-furancarboxaldehyde*, (E)-4-(5-(hydroxymethyl) furan-2-yl)but-3-en-2-one*, methyl 1-(2-oxo-4-quinolyl)
formate*, hematinic acid methyl ester*, loliolide*, n-nonacosan, n-butyl pyroglutamate*, serine, threonine
Table 1
Chemical compounds identied in Epilobium angustifolium
* – chemical compounds identied in E. angustifolium for the rst time in the last six years (2014–2019) [2, 3, 8, 42-50].
58 A. Adamczak, M. Dreger, K. Seidler-Łożykowska, K. Wielgus
Essential oils
Kaškonienė et al. [8, 45] identied nearly 50 dier-
ent compounds in essential oils of reweed (table
1). Anethole and caryophyllenes were the most fre-
quent constituents of the essential oil obtained from
plants growing in Lithuania, and they divided speci-
mens into two chemotypes [45].
Phytochemical variability
Fireweed is characterized by signicant inter-pop-
ulation variability. Investigations of Kaškonienė et
al. [8, 45] showed that the total content of phenolics
and avonoids in E. angustifolium herb harvested in
the massive blooming phase from dierent Lithu-
anian populations varies from 70.6 to 144.5 mg/g
and from 14.3 to 41.0 mg/g, respectively. In turn, the
levels of these compounds in the samples consisting
of leaves and owers, and obtained from 10 Finnish
populations, were 151–206 mg/g and 5.8–16.6 mg/g.
Additionally, the inter-population variability was
strongly expressed in the ratio of oenothein B and A
as well as in avonoid abundance, especially myric-
etin-3-O-glucoside and myricetin-3-O-glucuronide
[3]. e phytochemical variation of E. angustifo-
lium increases when dierent plant parts are ana-
lyzed, and the raw material is collected in various
development phases (table 2). Generally, the high-
est polyphenol content was recorded in the massive
owering phase [3, 44, 47, 50, 57]. Flowers and in-
orescences are distinguished by high amounts of
avonoids [3, 44, 47]. It was found that avonoids
and ellagitannins exhibit the most specic distri-
bution pattern within the whole plant [3]. Flowers
contained 10% more oenothein B and half as much
oenothein A as leaves.
TRADITIONAL USES
E. angustifolium is an interesting medicinal and wild
edible plant of the Northern Hemisphere. Its aerial
parts (herb and leaves) have been used in European
folk medicine to treat stomach disorders, liver and
prostate gland inammation as well as kidney and
urinary tract diseases [58, 59]. Traditional appli-
cation of this plant in phytotherapy also includes
migraine headaches, insomnia, anaemia, delirium
tremens, infections, colds, etc. Externally, reweed
is used as antiphlogistic and antiseptic agent for
treating mycoses, minor burns, skin rashes, ulcers,
wounds as well as inammation of the ear, nose, and
throat [4, 12].
In the USA, usage of E. angustifolium is
rec
ommended by herbalists in the case of colic with
chronic, non-inammatory diarrhea, gastroenteri-
tis, vomiting, dysentery, and prostatitis [60]. In Rus-
sia, reweed tea is oen consumed as a remedy for
stomach ulceration, gastritis, and sleeping disorders
[61, 62]. In the 19th century, an infusion prepared
from fermented leaves of E. angustifolium, called
Ivan or Koporye tea, was popular in England and
other Western European countries, and it constitut-
ed a very important export commodity of the Rus-
sian Empire. In turn, reweed roots and stems are
used in Chinese medicine for treatment of traumatic
injury, subduing inammation, and menstrual dis-
orders [49].
A survey of ethnobotanical literature shows that
medicinal properties of E. angustifolium have been
well known by the North American indigenous
peoples, especially in Canada and Alaska. e First
Nations in northern Ontario used it to treat inam-
mation, burns, boils, sores, rashes, mouth ulcers,
and yeast infections [63]. Among the Cree, macer-
ated roots were applied to boils or infections, and
leaves of this species were plastered on bruises. A
tea from the whole plant was prepared by the Woods
Cree of Saskatchewan against intestinal parasites,
and crushed roots were used to boils, abscesses, and
wounds. A decoction of reweed herb was made in
parts of Alaska and throughout the Arctic to initi-
ate secretion of breast milk. In turn, the Cheyenne
of Montana applied a tea from roots and leaves to
rectal haemorrhage [64].
E. angustifolium has been widely utilized as a veg-
etable. Its young shoots, harvested in spring before
blooming, were the source of the sweet and succulent
raw pith or aer cooking they were eaten like aspara-
gus [30]. e unopened buds were added to salads,
or pickled like capers [64], whereas the petals were
used for jelly [65]. e Inuit consumed underground
plant parts, aer boiling [64]. In turn, the Saami oc-
casionally collected the leaves of reweed, mainly for
mixing it with reindeer milk. In famine years, this
plant has been eaten by the settlers in northern Swe-
den. Fireweed was also reported in the 19th century
among emergency bread additives [66].
Due to the mass occurrence and blooming,
E. angustifolium belongs to the important honey
plants in Canada and Russia (especially Siberia).
In Alaska, a sugar syrup prepared with boiled clo-
ver and fireweed blossoms is also known under
the same name of fireweed honey [67]. In this
59
Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review
Vol. 65 No. 3 2019
region, rhubarb candy with fireweed vodka, jelly
from fireweed blossoms and ice cream with its
petals are made, too.
The stem fibres of E. angustifolium were used to
weave of fishing nets [30]. The fresh leaves were
utilized for preserving of bowstrings, whereas
flowers for waterproofing of mittens and rawhide
thongs [64].
Among the plants occurring in the North, E. an-
gustifolium is one of the most attractive species. Be-
cause of its easy cultivation, large and numerous
purple owers and deep red autumn foliage, it occa-
sionally grows as an ornamental. Fireweed was also
chosen as the oral emblem of Yukon, and it is on
the ag of this territory of Canada [65].
CONCLUSIONS
E. angustifolium is a valuable medicinal plant, used
especially in the treatment of urogenital disorders:
benign prostatic hyperplasia (BPH) and prostati-
tis. In the North (Canada, Alaska, Scandinavia,
and Siberia), it has been traditionally used as an
edible, honey and decorative species, too. E. angus-
tifolium is a rich source of polyphenols: avonoids,
phenolic acids and ellagitannins. Phytochemi-
cal analyses resulted in the identication of about
250 metabolites, including about 170 substances
found for the rst time in this plant in the last six
years. Two bioactive compounds: oenothein B and
quercetin-3-O-glucuronide are proposed for the
identication and standardization of the reweed
raw material. E. angustifolium is characterized by
Source of
variability
Content of Plant part Harvest time Reference: [57]
Polyphenols Tannins Flavonoids
Plant part
and harvest
time
40.6–85.0 77.2–162.8 0.05–0.19 Roots
From May to
October (Estonia)
Conclusion:
Summer (July-August) is the
optimal time of harvest of
the plant raw material.
55.9–83.3 27.3–149.9 0.06–0.21 Stems
27.6–63.8 160.6–414.2 1.63–2.35 Leaves
34.1–34.7 279.0–361.5 1.55–2.09 Flowers
35.4–46.7 175.4–202.1 0.68–1.22 Fruits
Source of
variability
Content in herb during vegetation Content in dierent parts of plants Reference: [44]
Flavonoids Vegetation phase Flavonoids Plant part Vegetation phase
Vegetation
phase and
plant part
3.39 Intensive growing 12.57 Flowers
Massive blooming
phase
Conclusion:
Flowers and the herb in the
massive blooming phase
are the most valuable raw
material.
Conclusion:
Myricetin is the dominant
avonoid in owers.
9.03 Flower buds 6.27 Leaves
11.12 Massive blooming 2.26 Stems
9.10 Ripening of fruits
7.56 End of vegetation
Content of individual avonoids during the massive blooming phase Plant
part
Hyperoside Myricetin Quercitrin Quercetin Kaempferol
Plant part
2.34 8.75 1.45 0.02 0.02 Flowers
4.43 0.65 1.14 0.04 0.02 Leaves
1.76 0.12 0.37 0.01 0.01 Stems
Source of
Variability
Content of
Plant part Reference: [3]
Oenothein B Oenothein A Neochlorogenic
acid
Quercetin-3-
O-GlcA
Plant part
83.37 25.12 1.11 1.61 Flowers Conclusion:
e inorescence apex
exhibits the highest content
of oenothein B and A, while
the leaves are the richest in
neochlorogenic acid and
quercetin-3-O-glucuronide.
75.44 22.83 1.10 1.49 Flower buds
66.09 43.18 4.71 5.23 Leaves
148.28 52.14 1.36 1.48 Apex of inorescence
51.32 24.32 0.47 0.81 Bottom of inorescence
17.01–26.61 11.50–16.34 0.02–0.29 0.09–0.34 Vegetative part of stem
Quercetin-3-O-GlcA – quercetin-3-O-glucuronide.
Table 2
Phytochemical variability of Epilobium angustifolium (mg/g) in relation to the plant part and time of harvest/vegetation phase
60 A. Adamczak, M. Dreger, K. Seidler-Łożykowska, K. Wielgus
signicant phytochemical variability in relation
to the geographical origin, plant part and time of
harvest/vegetation phase. Flowers and the herb in
the massive blooming phase are the most valuable
plant raw material. e inorescence apex exhibits
the highest content of oenothein B and A, while the
leaves are the richest in neochlorogenic acid and
quercetin-3-O-glucuronide.
ACKNOWLEDGEMENTS
is work was funded by the Polish National Cen-
tre of Research and Development (grant no. PBS2/
A8/23/2013) and the Polish Ministry of Science and
Higher Education (contract number 205710/E-198/
SPUB/2016/1).
Ethical approval: e conducted research is not re-
lated to either human or animal use.
Conflict of interest: Authors declare no conflict
of interest.
REFERENCES
1. Allkanjari O, Vitalone A. What do we know
about phytotherapy of benign prostatic hyperpla-
sia? Life Sci J 2015; 126:42-56. doi: http://dx.doi.
org/10.1016/j.lfs.2015.01.023
2. Baert N, Karonen M, Salminen JP. Isolation,
characterisation and quantication of the main
oligomeric macrocyclic ellagitannins in Epilo-
bium angustifolium by ultra-high performance
chromatography with diode array detection and
electrospray tandem mass spectrometry. J Chro-
matogr A 2015; 1419:26-36. doi: http://dx.doi.
org/10.1016/j.chroma.2015.09.050
3. Baert N, Kim J, Karonen M, Salminen JP. Inter-
population and inter-organ distribution of the
main polyphenolic compounds of Epilobium
angustifolium. Phytochemistry 2017; 134:54-
63. doi: http://dx.doi.org/10.1016/j.phyto-
chem.2016.11.003
4. Schepetkin IA, Ramstead AG, Kirpotina LN, Voy-
ich JM, Jutila MA, Quinn MT. erapeutic poten-
tial of polyphenols from Epilobium angustifolium
(reweed). Phytother Res 2016; 30(8):1287-97.
doi: http://dx.doi.org/10.1002/ptr.5648
5. Kiss A, Kowalski J, Melzig MF. Induction of
neutral endopeptidase activity in PC-3 cells
by an aqueous extract of Epilobium angustifo-
lium L. and oenothein B. Phytomedicine 2006;
13(4):284-9. doi: http://dx.doi.org/10.1016/j.
phymed.2004.08.002
6. Kiss AK, Bazylko A, Filipek A, Granica S, Jaszewska
E, Kiarszys U et al. Oenothein B’s contribu-Oenothein B’s contribu-
tion to the anti-inammatory and antioxidant
activity of Epilobium sp. Phytomedicine 2011;
18(7):557-60. doi: http://dx.doi.org/10.1016/j.
phymed.2010.10.016
7. Stolarczyk M, Piwowarski JP, Granica S, Stefańska
J, Naruszewicz M, Kiss AK. Extracts from Epilo-
bium sp. herbs, their components and gut mi-
crobiota metabolites of Epilobium ellagitannins,
urolithins, inhibit hormone-dependent prostate
cancer cells-(LNCaP) proliferation and PSA se-
cretion. Phytother Res 2013; 27(12):1842-8. doi:
http://dx.doi.org/10.1002/ptr.4941
8. Kaškonienė V, Stankevičius M, Drevinskas T,
Akuneca I, Kaškonas P, Bimbiraitė-Survilienė K
et al. Evaluation of phytochemical composition
of fresh and dried raw material of introduced
Chamerion angustifolium L. using chromato-
graphic, spectrophotometric and chemomet-
ric techniques. Phytochemistry 2015; 115:184-
93. doi: http://dx.doi.org/10.1016/j.phyto-
chem.2015.02.005
9. Piwowarski JP, Bobrowska-Korczak B, Stanisławska
I, Bielecki W, Wrzesi R, Granica S et al. Evaluation
of the eect of Epilobium angustifolium aqueous ex-
tract on LNCaP cell proliferation in in vitro and in
vivo models. Planta Med 2017; 83(14-15):1159-68.
doi: http://dx.doi.org/10.1055/s-0043-109372
10. Yoshida T, Yoshimura M, Amakura Y. Chemical
and biological signicance of oenothein B and
related ellagitannin oligomers with macrocyclic
structure. Molecules 2018; 23(3):552. doi: http://
dx.doi.org/10.3390/molecules23030552
11. Rauha JP, Remes S, Heinonen M, Hopia A, Käh-
könen M, Kujala T et al. Antimicrobial eects of
Finnish plant extracts containing avonoids and
other phenolic compounds. Int J Food Microbiol
2000; 56(1):3-12. doi: http://dx.doi.org/10.1016/
S0168-1605(00)00218-X
12. Battinelli L, Tita B, Evandri MG, Mazzanti G.
61
Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review
Vol. 65 No. 3 2019
Antimicrobial activity of Epilobium spp. extracts.
Farmaco 2001; 56(5-7):345-8. doi: http://dx.doi.
org/10.1016/S0014-827X(01)01047-3
13. Webster D, Taschereau P, Belland RJ. Antifun-
gal activity of medicinal plant extracts; prelimi-
nary screening studies. J Ethnopharmacol 2008;
115:140-6. doi: http://dx.doi.org/10.1016/j.
jep.2007.09.014
14. Bartfay WJ, Bartfay E, Johnson JG. Gram-negative
and Gram-positive antibacterial properties of the
whole plant extract of willow herb (Epilobium an-
gustifolium). Biol Res Nurs 2012; 14(1):85-9. doi:
http://dx.doi.org/10.1177/1099800410393947
15. Kosalec I, Kopjar N, Kremer D. Antimicrobial
activity of willowherb (Epilobium angustifolium
L.) leaves and owers. Curr Drug Targets 2013;
14(9):986-91. doi: http://dx.doi.org/10.2174/1389
4501113149990177
16. Tita B, Abdel-Haq H, Vitalone A, Mazzanti
G, Saso L. Analgesic properties of Epilobium
angustifolium, evaluated by the hot plate test
and the writhing test. Farmaco 2001; 56(5-
7):341-3. doi: http://dx.doi.org/10.1016/S0014-
827X(01)01046-1
17. Ruszová E, Cheel J, Pávek S, Moravcová M, Her-
mannová M, Matějková I et al. Epilobium angus-
tifolium extract demonstrates multiple eects on
dermal broblasts in vitro and skin photo-protec-
tion in vivo. Gen Physiol Biophys 2013; 32(3):347-
59. doi: http://dx.doi.org/10.4149/gpb_2013031
18. Wagner WL, Hoch PC, Raven PH. Revised clas-
sication of the Onagraceae. Syst Bot Monogr
2007; 83:1-240.
19. Kubát K, Hrouda L, Chrtek J, Kaplan Z, Kirschn-
er J, Štěpánek J, eds. Klíč ke květeně České re-
publiky. [Key to the ora of the Czech Republic].
Praha. Academia, 2002:436-40.
20. Rutkowski L. Klucz do oznaczania roślin na-
czyniowych Polski niżowej. [Key to the vascu-
lar plants of Lowland Poland]. Warsaw. PWN,
2008:323-6
21. Jäger EJ, ed. Exkursionsora von Deutschland.
Band 3. Gefäßpanzen: Atlasband. [Flora of Ger--
many. Vol. 3. Vascular plants: atlas]. 11th ed. Hei-Vol. 3. -
delberg. Elsevier Spektrum Akademischer Ver-
lag, 2009:347-51.
22. e Plant List. Epilobium angustifolium L.
2013. http://theplantlist.org/tpl1.1/record/kew-
2790112. Accessed 12 July 2019.
23. Holub J. Taxonomic and nomenclatural remarks
on Chamaenerion auct. Folia Geobot Phytotaxon
1972; 7:81-90.
24. Chen C-J, Hoch PC, Raven PH. Systema t--
ics of Epilobium (Onagraceae) in China. Syst
Bot Monogr 1992; 34:1-209. doi: http://dx.doi.
org/10.2307/25027806
25. Sennikov AN. Chamerion or Chamaenerion
(Onagraceae)? e old story in new words. Taxon
2011; 60(5):1485-8.
26. Baum DA, Sytsma KJ, Hoch PC. A phyloge-
netic analysis of Epilobium (Onagraceae) based
on nuclear ribosomal DNA sequences. Syst
Bot 1994; 19(3):363-88. doi: http://dx.doi.
org/10.2307/2419763
27. Levin RA, Wagner WL, Hoch PC, Nepokroe M,
Pires JC, Zimmer EA et al. Family-level relation-
ships of Onagraceae based on chloroplast rbcL
and ndhF data. Am J Bot 2003; 90(1):107-15. doi:
http://dx.doi.org/10.3732/ajb.90.1.107
28. Levin RA, Wagner WL, Hoch PC, Hahn WJ, Ro-
driguez A, Baum DA et al. Paraphyly in tribe On-
agreae: Insights into phylogenetic relationships
of Onagraceae based on nuclear and chloroplast
sequence data. Syst Bot 2004; 29(1):147-64. doi:
http://dx.doi.org/10.1600/036364404772974293
29. Nowick E. Historical common names of Great
Plains Plants, with Scientic Names Index. Vol-
ume II: Scientic Names Index. Lincoln. Zea E-
Books, 2015:1-452.
30. Fleenor R. Plant Guide for Fireweed (Chamer-
ion angustifolium). Spokane. USDA-Natural Re-
sources Conservation Service, 2016:1-5.
31. Tacik T. Rząd: Myrtales, Mirtowce. [Order: Myr--
tales]. In: Szafer W, Pawłowski B, eds. Flora Pol--
ska. Rośliny naczyniowe Polski i ziem ościennych.
Tom VIII [Flora of Poland. Vascular plants of
Poland and neighboring lands. Vol. 8], Warsaw.
PWN, 1959:184-269.
62 A. Adamczak, M. Dreger, K. Seidler-Łożykowska, K. Wielgus
32. Myerscough PJ. Biological ora of the British
Isles. Epilobium angustifolium L (Chamaenerion
angustifolium (L) Scop). J Ecol 1980; 68:1047-74.
33. Broderick DH. e biology of Canadian weeds.
93. Epilobium angustifolium L. (Onagraceae). Can
J Plant Sci 1990; 70(1):247-59. doi: http://dx.doi.
org/10.4141/cjps90-027
34. Wiese JL, Meadow JF, Lapp JA. Seed weights for
northern Rocky Mountain native plants with an
emphasis on Glacier National Park. Native Plants
J 2012; 13:39-49. doi: http://dx.doi.org/10.3368/
npj.13.1.39
35. Buchwald W, Kozłowski J, Szczyglewska D, Fory-
cka A. Biology of germination of medicinal plant
seeds. Part XXII: Seeds of Chamaenerion angus-
tifolium (L.) Scop. from Oenotheraceae family.
Herba Pol 2006; 52:16-21.
36. Mosquin T. A new taxonomy for Epilobium an-
gustifolium L. (Onagraceae). Brittonia 1966;
18:167-88.
37. Chen C-J, Hoch PC, Raven PH, Bouord DE,
Wagner WL. Onagraceae. Flora of China. Beijing.
Science Press, 2007:400-27.
38. Martin SL, Husband BC. Adaptation of diploid
and tetraploid Chamerion angustifolium to
elevation but not local environment. Evolution
2013; 67:1780-91. doi: http://dx.doi.org/10.1111/
evo.12065
39. ompson KA, Husband BC, Maherali H. Cli-
matic niche dierences between diploid and
tetraploid cytotypes of Chamerion angustifolium
(Onagraceae). Am J Bot 2014; 101:1868-75. doi:
http://dx.doi.org/10.3732/ajb.1400184
40. Husband BC, Schemske DW. Cytotype distribu-
tion at a diploid-tetraploid contact zone in Cha-
merion (Epilobium) angustifolium (Onagraceae).
Am J Bot 1998; 85(12):1688-94. doi: http://dx.doi.
org/10.2307/2446502
41. Guo W, Yang J, Sun X-D, Chen G-J, Yang Y-P,
Duan Y-W. Divergence in eco-physiological re--
sponses to drought mirrors the distinct distri-
bution of Chamerion angustifolium cytotypes
in the Himalaya-Hengduan Mountains region.
Front Plant Sci 2016; 7:1329. doi: http://dx.doi.
org/10.3389/fpls.2016.01329
42. Frolova TS, Sal’nikova OI, Dudareva TA, Kukina
TP, Sinitsyna OI. Isolation of pomolic acid from
Chamaenerion angustifolium and the evaluation of
its potential genotoxicity in bacterial test systems.
Russ J Bioorganic Chem 2014; 40(1):82-8. doi:
http://dx.doi.org/10.1134/S1068162013060046
43. Granica S, Piwowarski JP, Czerwińska ME, Kiss
AK. Phytochemistry, pharmacology and tradi--
tional uses of dierent Epilobium species (Ona-
graceae): A review. J Ethnopharmacol 2014;
156:316-46. doi: http://dx.doi.org/10.1016/j.
jep.2014.08.036
44. Maruška A, Ragažinskienė O, Vyšniauskas O,
Kaškonienė V, Bartkuvienė V, Kornyšova O et al.
Flavonoids of willow herb (Chamerion angusti-
folium (L.) Holub) and their radical scavenging
activity during vegetation. Adv Med Sci 2014;
59(1):136-41. doi: http://dx.doi.org/10.1016/j.ad-
vms.2013.10.002
45. Kaškonienė V, Maruška A, Akuņeca I,
Stankevičius M, Ragažinskienė O, Bartkuvienė V
et al. Screening of antioxidant activity and volatile
compounds composition of Chamerion angusti-
folium (L.) Holub ecotypes grown in Lithuania.
Nat Prod Res 2016; 30(12):1373-81. doi: http://
dx.doi.org/10.1080/14786419.2015.1058792
46. Moilanen J, Koskinen P, Salminen JP. Distribution
and content of ellagitannins in Finnish plant spe-
cies. Phytochemistry 2015; 116:188-97. doi: http://
dx.doi.org/10.1016/j.phytochem.2015.03.002
47. Monschein M, Jaindl K, Buzimkić S, Bucar F.
Content of phenolic compounds in wild popula-
tions of Epilobium angustifolium growing at dif-
ferent altitudes. Pharm Biol 2015; 53(11):1576-
82. doi: http://dx.doi.org/10.3109/13880209.201
4.993039
48. Deng LQ, Zhou SY, Mao JX, Liu S, Lan XZ, Liao
ZH et al. HPLC-ESI-MS/MS analysis of pheno-
lics and in vitro antioxidant activity of Epilobium
angustifolium L. Nat Prod Res 2018; 32(12):1432-
5. doi: http://dx.doi.org/10.1080/14786419.2017.
1344659
49. Deng L, Zong W, Tao X, Liu S, Feng Z, Lin Y et
al. Evaluation of the therapeutic eect against
benign prostatic hyperplasia and the active con-
stituents from Epilobium angustifolium L. J Eth-
nopharmacol 2019; 232:1-10. doi: http://dx.doi.
63
Fireweed (Epilobium angustifolium L.): botany, phytochemistry and traditional uses. A review
Vol. 65 No. 3 2019
org/10.1016/j.jep.2018.11.045
50. Gryszczyńska A, Dreger M, Piasecka A, Kachlicki
P, Witaszak N, Sawikowska A et al. Qualitative
and quantitative analyses of bioactive compounds
from ex vitro Chamaenerion angustifolium (L.)
(Epilobium angustifolium) herb in dierent har-
vest times. Ind Crops Prod 2018; 123:208-20. doi:
http://dx.doi.org/10.1016/j.indcrop.2018.06.010
51. Hevesi TB, Blazics B, Kéry Á. Polyphenol com-
position and antioxidant capacity of Epilobium
species. J Pharm Biomed Anal 2009; 49(1):26-31.
doi: http://dx.doi.org/10.1016/j.jpba.2008.09.047
52. Ducrey B, Marston A, Göhring S, Hartmann
RW, Hostettmann K. Inhibition of 5α-reductase
and aromatase by the ellagitannins oenothein
A and oenothein B from Epilobium species.
Planta Med 1997; 63(2):111-4. doi: http://dx.doi.
org/10.1055/s-2006-957624
53. Granica S, Bazylko A, Kiss AK. Determination of
macrocyclic ellagitannin oenothein B in plant ma-
terials by HPLC-DAD-MS: method development
and validation. Phytochem Anal 2012; 23(6):582-
7. doi: http://dx.doi.org/10.1002/pca.2358
54. Hiermann A, Mayr K. e investigation of active
compounds from Epilobium species. e occur-
rence of sitosterol derivatives in Epilobium angus-
tifolium L. and Epilobium parviorum Schreb. Sci
Pharm 1985; 53:39-44.
55. Nowak R, Krzaczek T. Sterole w zielu Epilobium
angustifolium L. [Sterols in the herb of Epilobium
angustifolium L.]. Herba Pol 1998; 44(4):297-9.
56. Węglarz Z, Kosakowska O, Pelc M, Geszprych A,
Przybył JL, Bączek K. Intraspecic variability of
reweed (Chamaenerion angustifolium /L./ Scop.)
and evening primrose (Oenothera biennis L.) in re-
spect of sterol content. Herba Pol 2011; 57(2):7-15.
57. Jürgenson S, Matto V, Raal A. Vegetational varia-
tion of phenolic compounds in Epilobium angus-
tifolium. Nat Prod Res 2012; 26(20):1951-3. doi:
http://dx.doi.org/10.1080/14786419.2011.643310
58. Redžić SS. e ecological aspect of ethnobotany and
ethnopharmacology of population in Bosnia and
Herzegovina. Coll Antropol 2007; 31(3):869-90.
59. Vogl S, Picker P, Mihaly-Bison J, Fakhrudin N,
Atanasov AG, Heiss EH et al. Ethnopharmaco-
logical in vitro studies on Austria’s folk medicine
– An unexplored lore in vitro anti-inammatory
activities of 71 Austrian traditional herbal drugs.
J Ethnopharmacol 2013; 149:750-71. doi: http://
dx.doi.org/10.1016/j.jep.2013.06.007
60. Moore M. Specic indications for herbs in gen-
eral use. 3rd ed. Bisbee. Southwest School of bo-
tanical Medicine, 1997:1-58. http://www.swsbm.
com/ManualsMM/SpecIndic3.pdf. Accessed 12
July 2019.
61. Shikov AN, Poltanov EA, Dorman HJD, Makarov
VG, Tikhonov VP, Hiltunen R. Chemical compo-
sition and in vitro antioxidant evaluation of com-
mercial water-soluble willow herb (Epilobium an-
gustifolium L.) extracts. J Agric Food Chem 2006;
54(10):3617-24. doi: http://dx.doi.org/10.1021/
jf052606i
62. Galambosi B, Galambosi Z, Shikov AN, Kosman
VM, Pozharitskaya ON, Kauppinen S et al. Optimi-
zation of the fermentation of reweed (Epilobium
angustifolium) shoot. In: Kauppinen S, Galambosi
B, eds. Fireweed, roseroot, bergenia and choke-
berry – joint research for supporting the herb pro-
duction. Nat Res Bioeconomy Stud 2016; 72:11-22.
http://urn./URN:ISBN:978-952-326-338-3. Ac-
cessed 12 July 2019.
63. Hassan HM, Jiang Z-H, Syed TA, Qin W. Re-
view: Northern Ontario medicinal plants. Can J
Plant Sci 2012; 92(5):815-28. doi: http://dx.doi.
org/10.4141/cjps2012-006
64. Rogers RD. Fireweed – a treasured medicine of the
boreal forest. Discov Phytomed 2014; 1:10-5. doi:
http://dx.doi.org/10.15562/phytomedicine.2014.16
65. Small E, Catling PM. Canadian medicinal crops.
Ottawa. NRC Research Press, 1999:1-240.
66. Svanberg I. e use of wild plants as food in pre-in-
dustrial Sweden. Acta Soc Bot Pol 2012; 81(4):317-
27. doi: http://dx.doi.org/10.5586/asbp.2012.039
67. Petersen S, Bryant VM. Fireweed – a premier (but
ckle) honey plant. Am Bee J 2010; 150(4):395-8.
... Therapeutic plants are of major importance in human life due to their bioactive phytochemicals, which provide potential health benefits and possess commercial value [1][2][3]. ...
... Many Onagraceae species, including In the last decade, the chemistry and biological activity of Chamaenerion species have been studied intensively, highlighting the significance of fireweed as an important medicinal plant widely utilized in the pharmaceutical, food, and cosmetic industries [10,11]. C. angustifolium,commonly known as willowherb or rosebay willowherb, Chamaenerion angustifolium (L.) Holub, Chamaenerion angustifolium (L.) Scop., Epilobium angustifolium L.,is a perennial herbaceous plant widely distributed across various habitats in the Northern Hemisphere [3,11,12]. Traditional medicine has used fireweed plants to treat a variety of ailments, such as wound healing, infections, skin diseases, colds, urinary problems like prostatitis, gastric disorders, migraine headaches, and sleep disturbances [13,14]. In northern and eastern Europe, it is utilized as a food plant, particularly in the form of tea or as a traditional herbal remedy. ...
... These polyphenolic compounds are vital for scavenging free radicals, reducing oxidative stress, and protecting cells from damage due to their potent antioxidant properties. The potent antioxidant capacity of these extracts increases the likelihood of many health benefits, including antiinflammatory and disease-preventive qualities against oxidative stress [3,107]. The greatest radical scavenging activity was demonstrated by oenothein B in an HPLC-DPPH assay [23]. ...
Article
Full-text available
The Chamaenerion genus, particularly Chamaenerion angustifolium and Chamaenerion latifolium, is recognized for its rich phytochemical composition and extensive medicinal properties. These species are abundant in polyphenols, flavonoids, and tannins, which contribute to their potent antioxidant, antimicrobial, and anticancer activities. This review provides a comprehensive analysis of their phytochemical constituents, with an emphasis on how processing methods, including fermentation, influence bioactivity. Notably, fermentation enhances the levels of key bioactive compounds, such as oenothein B, gallic acid, and ellagic acid, thereby increasing their pharmacological potential. Additionally, this review evaluates the biological activities of Chamaenerion species in relation to their chemical composition, while also considering the limitations of current studies, such as the lack of in vivo or clinical trials. The literature for this review was sourced from scientific databases, including PubMed, Scopus, and ScienceDirect, covering research from 2010 to 2024. Future studies should focus on optimizing extraction methods, elucidating synergistic bioactivities, and conducting in-depth clinical trials to validate their efficacy and safety.
... Epilobium angustifolium L. (=Chamerion angustifolium Scop.) (Onagraceae) is renowned for its usage in nutraceuticals, diet supplements, and cosmetic products [1]. The species is distributed widely in the temperate zones of Europe, Asia, and North America [2]. E. angustifolium is commonly referred to as rosebay willowherb, fireweed, or great-willowherb [3]. ...
... E. angustifolium is commonly referred to as rosebay willowherb, fireweed, or great-willowherb [3]. It is a perennial plant with an erect stem up to 2 m high and which develops large racemes with a number of pink flowers [2]. ...
... Overall, more than 250 secondary metabolites, especially flavonoids, ellagitannins, and phenolic acids, have been reported in E. angustifolium extracts [1,2,4]. Fireweed also contains lignans, triterpenoids, steroids, fatty acids, essential oil, and alkaloids [1]. ...
Article
Full-text available
The aerial parts of Epilobium angustifolium L. (fireweed) (Onagraceae) are renowned for their use in the treatment of prostatic, kidney and urinary tract diseases, and skin infections. In this work, a comprehensive phytochemical profiling of the methanol-aqueous extract from E. anfustifolium aerial parts was performed by the means of liquid chromatography–Orbitrap high-resolution mass spectrometry. Annotation and dereplication of 121 secondary metabolites were achieved, including acylquinic acids, gallo- and ellagitannins, flavonoids, phenolic acids, and their glycosides. Forty-six compounds are reported for the first time in the species. Total phenolic and flavonoid content were 85.04 ± 0.18 mg GAE/g and 27.71 ± 0.74 mg QE/g, respectively. Antioxidant capacity assessment revealed that the extract actively scavenged DPPH and ABTS radicals (310.74 and 466.82 mg TE/g) along with a high reducing power in CUPRAC and FRAP assay (442.83 and 291.50 mg TE/g), respectively, and metal chelating (48.20 mg EDTA/g). The extract also had a distinct impact on α-glucosidase (3.48 mmol ACAE/g) and moderate activity towards α-amylase (0.44 mmol ACAE/g) and lipase (8.03 OE/g). It inhibited acetyl- and butyrylcholinesterase (2.05 and 1.67 mg GALE/g) and had a prominent anti-tyrosinase effect (61.91 mg KA/g). Our results contribute to establishing fireweed as a multifunctional agent for use in herbal preparations.
... The leaves and flowers of Epilobium L. species are a rich source of secondary metabolites, especially polyphenols, including flavonoids, phenolic acids, and tannins [5-7], which possess antioxidant, antimicrobial, anticancer, and anti-inflammatory properties [4]. In addition to polyphenols, there are lipophilic compounds such as steroid triterpenoids and fatty acids [7,8]. The macrocyclic ellagitannins, especially oenothein B, are considered to be the major active compounds determining the biological activity of E. angustifolium extracts [9]. ...
... The macrocyclic ellagitannins, especially oenothein B, are considered to be the major active compounds determining the biological activity of E. angustifolium extracts [9]. Several triterpene acids were also found in the E. angustifolium raw materials, namely, oleanolic, pomolic, and ursolic acids [7]. The presence of both triterpenoids and polyphenols (especially oenothein B) in herbal raw material of E. angustifolium and their mutual potentiation determines the presence of pronounced antioxidant potential [10], which helps neutralize free radicals, protecting cells from oxidative damage and inflammation, which underlie all diseases [11]. ...
... Rutin, hyperoside, isoquercitrin, quercetin, oenothein A, oenothein B, and all polyphenolic acids were among the most abundant metabolites. Gallic acid, ellagic acid, quercetin, and kaempferol were frequently determined in the leaves and upper part of E. angustifolium shoots [5,7,15,31]. These flavonoids with antioxidant and anti-inflammatory properties are responsible for the pharmacological potential of the plant [4,15,16]. ...
Article
Full-text available
The composition of secondary metabolites undergoes significant changes in plants depending on the growth phase and the influence of environmental factors. Therefore, it is important to determine the harvesting time of plant material for the optimum secondary metabolite profile and therapeutic activity of the primary material. The shoots of Epilobium angustifolium are used as a healing tea due to the presence of polyphenolic compounds. The aim of this study was to assess the composition of phenolic compounds and triterpenoid saponins in E. angustifolium leaves and flowers and to estimate the dynamics of their content depending on the flowering phase. Qualitative and quantitative characterisation of polyphenols and triterpenoids in E. angustifolium samples from Ukraine of three flowering phases were performed using the high-performance liquid chromatography photo diode array (HPLC-PDA) method. During the present study, 13 polyphenolic compounds and seven triterpenoids were identified in the plant material. It was noted that the largest content and the best polyphenol profile was in late flowering. The most important polyphenolic compounds in the plant material were chlorogenic acid, hyperoside, isoquercitin, and oenothein B. The triterpenoid profile was at its maximum during mass flowering, with corosolic and ursolic acids being the dominant metabolites. The results of the analysis revealed that the quantity of many of the tested metabolites in the raw material of E. angustifolium is dependent on the plant organ and flowering phase. The largest content of most metabolites in the leaves was in late flowering. In the flowers, the quantity of the metabolites studied was more variable, but decreased during mass flowering and increased significantly again in late flowering. The results show that E. angustifolium raw material is a potential source of oenothein B and triterpenoids.
... Fireweed, Chamaenerion angustifolium (L.) Holub (also called Chamerion angustifolium and Epilobium angustifolium), is a well-known medicinal plant found in many countries of the Northern Hemisphere, including Lithuania. Like any other medicinal plant, C. angustifolium has an abundance of polyphenols, especially ellagitannins, flavonoids, and phenolic acids [5]. Research on C. angustifolium raw materials has received considerable attention in the last twenty years. ...
... (36.19-100.15 ± 6.07 RE mg/g), and in stem samples by 22. 5 The biologically active compound's stability was highest when frozen in liquid nitrogen (−196 °C). The total content of phenolic compounds in leaf samples decreased only by 1.7-6.6% ...
Article
Full-text available
The study evaluates different preparation methods for identifying the best strategy for extracting biologically active compounds from raw Chamaenerion angustifolium (L.) Holub plant material. The methodologies include direct aqueous methanol extraction with a combination of natural aerobic and anaerobic fermentation for 24–72 h, followed by 35 °C and 60 °C drying. Furthermore, the study also focuses on determining the different temperature storage conditions on the stability of biologically active compounds. UV-VIS spectroscopy was used to quantitatively evaluate the total content of phenolic compounds, flavonoids, and radical scavenging activity. For qualitative analysis, chromatographic separation with electrochemical detection (ED) of extracted compounds, a gradient high-performance liquid chromatography (HPLC) system was used. Study results indicate that 48 h natural aerobic fermentation followed by 35 °C drying and 75% (v/v) aqueous methanol extraction yielded the maximum amount of biologically active compounds in Chamaenerion angustifolium (L.) Holub leaves, blossom, and stem samples. Freezing samples in liquid nitrogen had the lowest impact on the total content of phenolic compounds, flavonoids, and radical scavenging activity. HPLC-ED system results identified chlorogenic acid, oenothein B, trans-p-Coumaric acid, ellagic acid, and rutin in Chamaenerion angustifolium (L.) Holub leave samples.
... It has a flavour of sweet cucumber with a peppery aftertaste (Kirtley, 2024). Dry stems can be used as twine or to light fires while extracts are used in some creams, shampoos and other cosmetic products, especially for acne (Adamczak et al., 2019). It is also widely used in traditional medicine as it is reported to have anti-cancer, anti-bacterial, anti-inflammatory, and anti-aging properties due to the presence of a diversity of polyphenols and secondary metabolites (reviewed in Prasad et al., 2018). ...
... Here we present the first high-quality genome of C. angustifolium. Its genome will not only provide an important baseline resource for studying the evolution of autopolyploids in this model species, but also for helping to dissect the biochemical pathways that lead to the production of over 250 metabolites that may be bioactive and explain the widespread use of this species in traditional medicine (Adamczak et al., 2019;Kadam et al., 2018). ...
Article
Full-text available
We present a genome assembly from an individual Chamaenerion angustifolium (fireweed; Tracheophyta; Magnoliopsida; Myrtales; Onagraceae). The genome sequence is 655.9 megabases in span. Most of the assembly is scaffolded into 18 chromosomal pseudomolecules. The mitochondrial and plastid genome assemblies have lengths of 495.18 kilobases and 160.41 kilobases in length, respectively.
... (rosemary fireweed), Onagraceae, grows in disturbed environments, especially in mine waste dumps (Ranđelović et al. 2016). It is an edible, honey-producing, medicinal and ornamental plant (Adamczak et al. 2019;Vlase et al. 2023), with various polyphenols, including flavonoids, phenolic acids, and tannins (Granica et al. 2014). ...
... Өз кезегінде Chamaenerion Seg. тамырлары мен сабағы қытай медицинасында әртүрлі жарақаттар мен қабынуды емдеу үшін қолданылады [7]. Бұл өсімдікті фитотерапияда дәстүрлі, бас ауруы, ұйқысыздық, анемия, жұқпалы, суық тию аурулары және т.б. ...
Article
Бұл мақалада жабайы өсетін дәрілік өсімдік жіңішке жапырақты күреңот туралы ақпарат берілген, оның ботаникалық атауы – Chamaenerion Seg. Chamaenerion Seg. антипролиферативті, қабынуға қарсы, иммуномодуляциялық, антиоксидантты, сондай-ақ микробқа қарсы белсенділікті қамтитын емдік қасиеттеріне байланысты ежелден бері белгілі. Жіңішке жапырақты күреңоттың биохимиялық құрамы зерттелді, оның дәрілік қасиеттері туралы мәліметтер келтірілген. Күреңот биологиялық белсенді заттардың, дәрумендердің, өмірлік маңызды макро- және микроэлементтердің құнды көзі болып табылады және дәстүрлі медицинада қолданылады. Әр түрлі мамандар жүргізген қолданыстағы зерттеулердің нәтижелерін, ғылыми және тарихи фактілерді талдау, жоғарыда аталған түр дәрілік ғана емес, сонымен қатар құнды өсімдік шикізаты ретінде де кеңінен қолданылатынын көрсетті. Функционалды тағамдық қоспалардың құнды көзі ретінде жіңішке жапырақты күреңотты пайдалану туралы мәліметтер бар. Chamaenerion Seg. шөп сығындысы «Качотта» түріндегі жартылай қатты ірімшікті байыту үшін, қанықпаған және қаныққан май қышқылдарының құрамын арттыру үшін айран өндіру технологиясында қолданылған. Сондай-ақ, Chamaenerion Seg. шикізаты геродиетикалық тамақтану үшін фитошай мен кофе сусынын өндіру үшін қолданылады.
Article
The recent outbreak of Omicron strains of coronavirus disease urged the search for novel treatments from natural products such as Epilobium species. The present work reports a comparative HPLC‐DAD study of the polyphenolic composition of the crude extracts of Epilobium angustifolium and Epilobium hirsutum . Oenothein B, gallic acid, hyperoside, and isoquercitin were the dominant phenolic compounds. E. hirsutum methanol extract showed a high radical scavenging activity as demonstrated by the HPLC‐ABTS assay due to its richness in phenolic compounds. The polysaccharide‐rich extracts and water extracts of E. hirsutum showed potent anti‐coronavirus SARS‐CoV‐2 activity against the Omicron strain at 10 μg/mL with inhibition percentages of 38.4% and 46.1%, respectively. In contrast, the methanol (50% v/v) extract was inactive. Rutin and chlorogenic acid docked well into the binding pocket of the coronavirus spike protein. Emerging evidence suggests that suppressing excessive neutrophilic inflammation during the late stage of coronavirus infection benefits patients’ survival. The methanol extracts of both plants completely inhibited fMLF/CB‐induced elastase release in human neutrophils at 10 μg/mL (IC 50 2.44 μg/mL), while the water extract showed an IC 50 of 5.67 μg/mL. While several compounds docked well into the spike protein, the major and marker compound oenothein B showed promising in vitro anti‐coronavirus activity with an IC 50 of 6.08 µM in hACE2‐overexpressing HEK293 cells, mimicking the entry of wild‐type SARS‐CoV‐2 into human host cells. The results indicated that E. hirsutum might be helpful in the treatment of coronavirus infections and related inflammatory syndromes.
Article
Relevance. Nowadays the popularity of Chamaenerion angustifolium as a medicinal plant and as a tea is growing noticeably. Fireweed is an eclogically plastic species, that does not require high soil fertility and is widespread in Russia. Medical and food industries use leafs as a row material of fireweed. Series of phytochemical studies of Chamaenerion raw material have shown that it contains a wide variety of pharmacologically significant compounds, that accumulate as a result of both primary and secondary metabolism. The most important groups, formed as a result of secondary metabolism, are polyphenols, including flavonoids, phenolic acids and ellagitannins (including enothein B). Concentration of these chemical compounds equals 15% and even hither of the raw material (leaf). The aim . Identification of variability and relationships between the content of various groups of phenolic compounds in raw material of Chamaenerion angustifolium, depending on ecological conditions. Methods. At the first stage of our work was used the cartographic method. Were studied specimens from 27 points, growing in ecologically different areas of the Moscow, Kaluga and Yaroslavl regions. Phenolic compounds were determined using a spectrophotometer: flavonoids in terms of rutin, tannins and the amount of phenolic compounds, using the Folin-Ciocalteu reagent in terms of gallic acid. Results. The content of polyphenols, tannins and flavonoids in raw material of fireweed, collected in different ecological and soil aspects, was measured. Measurement results were compared, using correlation analysis. As the result of content analysis, it was found that the content of polyphenols in the leaves ranged from 9 to 11%, the content of flavonoids fell within the chain range of 2.5-3.5%, tannin content – 5.0-6.5%. A close correlation was found between the content of phenolic compounds and tannins (R=0.972). It indicates, that the shikimate pathway is the main process of biosynthesis secondary metabolites in the Chamaenerion angustifolium plant. Also it means the leading role of local ecological conditions of the studied areas.
Article
Full-text available
In 1990, Okuda et al. reported the first isolation and characterization of oenothein B, a unique ellagitannin dimer with a macrocyclic structure, from the Oenothera erythrosepala leaves. Since then, a variety of macrocyclic analogs, including trimeric–heptameric oligomers have been isolated from various medicinal plants belonging to Onagraceae, Lythraceae, and Myrtaceae. Among notable in vitro and in vivo biological activities reported for oenothein B are antioxidant, anti-inflammatory, enzyme inhibitory, antitumor, antimicrobial, and immunomodulatory activities. Oenothein B and related oligomers, and/or plant extracts containing them have thus attracted increasing interest as promising targets for the development of chemopreventive agents of life-related diseases associated with oxygen stress in human health. In order to better understand the significance of this type of ellagitannin in medicinal plants, this review summarizes (1) the structural characteristics of oenothein B and related dimers; (2) the oxidative metabolites of oenothein B up to heptameric oligomers; (3) the distribution of oenotheins and other macrocyclic analogs in the plant kingdom; and (4) the pharmacological activities hitherto documented for oenothein B, including those recently found by our laboratory.
Article
Full-text available
The aerial parts of Epilobium plants are widely used as folk medicine and food around the world. The present study was aimed to investigate the antioxidant activities and active chemical constituents from Epilobium angustifolium L. The results revealed that the EtOAc extract, rich in phenolic compounds and flavonoids (16.81 ± 0.67 g GAE/100 g extract and 4.95 ± 0.21 g QE/100 g extract, respectively), possessed significantly antioxidant activities in reducing power, DPPH radical scavenging activity, ABTS radical scavenging activity and highly in inhibiting lipid peroxidation activity. Simultaneously, active fractions F to H from EtOAc extracts showing potent in vitro antioxidant activities also contained high content of total phenolic and flavonoid. Twenty-eight compounds were identified as phenolic compounds and flavonoids by LC-MS/MS. The results illustrate that the E. angustifolium L., which is rich in phenolics, could be used as a natural resource of antioxidant ingredient.
Article
Full-text available
Polyploid species generally occupy harsher habitats (characterized by cold, drought and/or high altitude) than diploids, but the converse was observed for Chamerion angustifolium, in which diploid plants generally inhabit higher altitudes than their polyploid derivatives. Plants at high altitudes may experience cold-induced water stress, and we therefore examined the physiological responses of diploid and hexaploid C. angustifolium to water stress to better understand the ecological differentiation of plants with different ploidy levels. We conducted a common garden experiment by subjecting seedlings of different ploidy levels to low, moderate, and severe water stress. Fourteen indicators of physiological fitness were measured, and the anatomical characteristics of the leaves of each cytotype were determined. Both cytotypes were influenced by drought, and diploids exhibited higher fitness in terms of constant root:shoot ratio (R:S ratio) and maximum quantum yield of PS II (Fv/Fm), less reduced maximal photosynthetic rate (Amax), transpiration rate (E), intercellular CO2 concentration (Ci) and stomatal conductance (gs), and higher long-term water use efficiency (WUEL) under severe water stress than did hexaploids. Analysis of leaf anatomy revealed morphological adjustments for tolerating water deficiency in diploids, in the form of closely packed mesophyll cells and small conduits in the midvein. Our results indicate that diploid C. angustifolium is more tolerant of drought than hexaploid plants, ensuring the successful survival of the diploid at high altitudes. This eco-physiological divergence may facilitate the species with different cytotypes to colonize new and large geographic ranges with heterogeneous environmental conditions.
Article
Full-text available
Epilobium angustifolium is a medicinal plant used around the world in traditional medicine for the treatment of many disorders and ailments. Experimental studies have demonstrated that Epilobium extracts possess a broad range of pharmacological and therapeutic effects, including antioxidant, anti-proliferative, anti-inflammatory, antibacterial, and anti-aging properties. Flavonoids and ellagitannins, such as oenothein B, are among the compounds considered to be the primary biologically active components in Epilobium extracts. In this review, we focus on the biological properties and the potential clinical usefulness of oenothein B, flavonoids, and other polyphenols derived from E. angustifolium. Understanding the biochemical properties and therapeutic effects of polyphenols present in E. angustifolium extracts will benefit further development of therapeutic treatments from this plant. Copyright © 2016 John Wiley & Sons, Ltd.
Article
Ethnopharmacological relevance Plants of Epilobium angustifolium are popular in China to treatment of traumatic injury, subduing inflammation and menstrual disorders. In European, the preparations or extracts containing E. angustifolium are popular to treat prostate diseases. Recent research suggested that E. angustifolium showed therapeutic effects in early stage of BPH, inflammation of urethra and prostate, as well as micturition problems. And the related researches were focus on aqueous extract and its main constituent of oenothein B. Aim of the study This study aims to evaluate the therapeutic effect against BPH of the ethyl acetate extracts (EAE) and n-butanol extracts (BUE) from E. angustifolium and to chemical investigation of the active constituents. Materials and methods The in vitro anti-BPH activity was assessed by determining the benign prostatic hyperplasia epithelial-1 (BPH-1) cell viability using MTT assay as well as suppressing of prostate specific antigen (PSA) secretion in prostate epithelial cancer hormone-dependent (LNCaP) cells measured by ELISA method. The in vivo anti-BPH was evaluated by testosterone propionate induced BPH SD rats. After oral administration of BUE at 100, 200 and 400 mg/kg B.W. for 28 days, the prostate weight and index, plasma androgen level, histopathological alteration, oxidative and inflammatory-related factors in prostate were assessed. Phytochemical investigation on active extracts was carried by chromatographic and spectroscopic techniques. Anti-BPH activities of the isolates were evaluated in vitro. Results BUE and EAE from E. angustifolium exhibited significant anti-BPH effect in vitro. Further in vivo study demonstrated that BUE exhibited therapeutic effects against TP-induced BPH in SD rats via down-regulating of the androgen level, suppressing the expression of NF-κB and eventually alleviating the inflammatory responses and oxidative stress. Phytochemical research on BUE and EAE extracts led to the isolation and identification of 50 compounds. In vitro anti-BPH screening revealed that 26 compounds exhibited anti-proliferation in BHP-1 cell and 36 compounds showed PSA inhibition in LNCap cell, in which 7 compounds exhibited very significant anti-BPH activities in both two cell lines (P < 0.01), 5 compounds with extremely significant activities in one of the cell lines (P < 0.001), and compound 25 exhibited the most potent anti-BPH activity (P < 0.001). Conclusions E. angustifolium exhibited the therapeutic potential against BPH, and its active compounds may be used as candidate for treatment of BPH.
Article
The rosebay willowherb (Chamaenerion angustifolium (L.) Scop. syn. Epilobium angustifolium L.) from Onagraceae family is a valuable medicinal plant. The aim of our research was to measure the effect of different harvest times on the profile and concentration of oenothein B, polyphenols, flavonoids and sterols after ex vitro Chamaenerion angustifolium multiplication. For this purpose, we compared phytochemical properties of the herb in two ex vitro lines: German (DE) and Polish (PL), collected in two different harvest times: during and after the flowering period-in June and in September respectively. The qualitative and quantitative analyses were conducted using advanced LC-MS systems, including: HPLC-DAD-MS n , UPLC-PDA-MS/MS, HPLC-DAD, UPLC-MS/MS and the spectrophotometric methods. In the course of the qualitative analysis of herb samples, 45 phenolic metabolites were identified, from which gallic acid, oenothein B and quercetin 3-O-arabinoside were the principal compounds. In both lines, the quantitative determination with the use of two chromatographic methods showed the highest concentration of oenothein B, β−sitosterol and ellagic acid, whereas in the analysis with the spectro-photometric method, it was the total polyphenols content that predominated (expressed as gallic acid). In most cases, the flowering period was a better source of active compounds. The chemical characteristics of ex vitro raw material is similar to the field crop plants profile, confirming the positive application of the ex vitro cultivation method.
Article
Epilobium sp. are commonly used in traditional medicine in the treatment of early stages of benign prostatic hyperplasia and inflammation. It is suggested that a dominating constituent, oenothein B, is responsible for the extracts therapeutic effects. Several bioactivities were established for extracts and oenothein B in various in vitro models, but due to the questionable bioavailability of this dimeric macrocyclic ellagitannin, their significance in the in vivo effects remains unresolved. We have thus focused our attention on a complex comparative investigation of the in vitro and in vivo activities of phytochemically characterized Epilobium angustifolium aqueous extract and oenothein B on prostate cancer cells proliferation. Incubation of different cell lines with E. angustifolium aqueous extract resulted in a significant reduction of proliferation of PZ-HPV-7 and LNCaP cells, which was partly associated with antiandrogenic activity. These effects were fully congruent with oenothein B, examined in parallel. Oral supplementation of rats implanted with LNCaP cells with E. angustifolium aqueous extract 50–200 mg/kg b. w. resulted in a reduction of the occurrence of prostatic adenoma up to 13 %. Oenothein B was not detected in the urine and feces of the E. angustifolium aqueous extract-treated group, however, conjugates of nasutins gut microbiota metabolites of ellagitannins were detected in the urine, while in human volunteers supplemented with Epilobium tea, only urolithin conjugates were present. Despite observing significant and consistent effects in vitro and in vivo, we were unable to point out unequivocally the factors contributing to the observed E. angustifolium aqueous extract activity, facing the problems of an unknown metabolic fate of oenothein B and interspecies differences in E. angustifolium aqueous extract gut microbiota metabolism.
Article
Rosebay willowherb (Epilobium angustifolium) contains large amounts of polyphenolic compounds, including tellimagrandin I-based oligomeric ellagitannins (ETs). The aim of this study was to assess the interpopulational and inter-organ variability of the polyphenol fingerprint of E. angustifolium. Seven ETs, 11 flavonol glycosides and neochlorogenic acid were quantified by UHPLC-DAD-ESI-QqQ-MS in the leaves, flowers and stem parts of plants from 10 populations. Total polyphenol content of leaves and flowers ranged from 150 to 200 mg/g dry wt, of which 90% was constituted by dimeric to heptameric ETs. Flowers contained, on average, 10% more oenothein B (dimeric ET) and 2 times less oenothein A (trimeric ET) than leaves. Tetrameric and pentameric ETs exhibited rather similar levels in leaves and flowers whereas hexameric and heptameric were 3-4 times more abundant in flowers than in leaves. Quercetin-3-O-rhamnoside, myricetin-3-O-rhamnoside and kaempferol-3-O-rhamnoside were specific to flower tissue and were absent from leaves. The inflorescence stem showed the highest content in total polyphenols with an average of 250 mg/g dry wt and contained remarkably large amounts of oenothein B and A. Polyphenol content steadily decreased along the inflorescence stem and reached its lowest level in the vegetative part of the stem. The interpopulational variability of most polyphenols was within a two- to threefold range across the 10 sampled populations. Myricetin-3-O-glucoside and myricetin-3-O-glucuronide, however, showed a more population-specific distribution with concentrations varying from 0 to 2.3 mg/g dry wt. Finally, this study showed that the levels of oenothein B and A in the plant are not interdependent but that their relative abundance is constant within a population.
Article
Containing thousands of entries of both vernacular and scientific names of Great Plains plants, the literature that informs this exhaustive listing spans nearly 300 years. Author Elaine Nowick has drawn from sources as diverse as Linnaeus, Lewis and Clark, and local university extension publications to compile the gamut of practical, and often fanciful, common plant names used over the years. Each common name is accompanied by a definitive scientific name with references and authority information. Interspersed with scientifically-correct botanical line drawings, the entries are written in standard ICBN format, making this a useful volume for scholars as well as lay enthusiasts alike. Volume 2 indexes the scientific names of those species, followed by listings of all the common names applied to them. Both volumes refer the common and scientific names back to a list of 190 pertinent authoritative sources.