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Primula veris L. and Primula elatior (L.) Hill represent medicinal plants used for the production of herbal teas and preparations with antioxidant and expectorant activity. Flowers and roots of both species possess the same biological activity. In the presented study, raw materials of wild growing P. veris and P. elatior were compared in terms of the content and composition of phenolic compounds using a fast and simple HPLC-DAD method. The study showed that flowers of both species were rich in flavonoids. However, P. veris flowers were characterized with a distinctly higher content of isorhamnetin-3-O-glucoside, astragalin, and (+)-catechin, whereas P. elatior occurred to be a richer source of rutoside and isorhamnetin-3-O-rutinoside. Hyperoside was found exclusively in P. elatior flowers. Phenolic glycosides (primverin and primulaverin) were identified only in the roots. Their content was about ten times higher in P. veris in comparison with P. elatior underground organs. The obtained results clearly show that both Primula species differ distinctly in terms of the content and composition of phenolic compounds. The compounds differentiating both species to the highest degree (hyperoside, in flowers, as well as primverin and primulaverin, in the roots) may be useful chemical markers in the identification and evaluation of both species.
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Research Article
Phenolics in Primula veris L. and P. elatior (L.)
Hill Raw Materials
Katarzyna Bdczek, JarosBaw L. PrzybyB,MaBgorzata Mirgos, Olga Kosakowska,
Izabela Szymborska-Sandhu, and Zenon Wwglarz
Laboratory of New Herbal Products, Department of Vegetable and Medicinal Plants, Warsaw University of Life Sciences-SGGW,
Nowoursynowska 166, 02-787 Warsaw, Poland
Correspondence should be addressed to Katarzyna Bączek; katarzyna baczek@sggw.pl
Received 3 March 2017; Revised 7 June 2017; Accepted 27 June 2017; Published 1 August 2017
Academic Editor: Ravi Ramasamy
Copyright ©  Katarzyna Bączek et al. is is an open access article distributed under the Creative Commons Attribution
License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly
cited.
Primula veris L. and Primula elatior (L.) Hill represent medicinal plants used for the production of herbal teas and preparations with
antioxidant and expectorant activity. Flowers and roots of both species possess the same biological activity. In the presented study,
raw materials of wild growing P. v e r i s and P. e l a t i o r were compared in terms of the content and composition of phenolic compounds
using a fast and simple HPLC-DAD method. e study showed that owers of both species were rich in avonoids. However, P. v e r i s
owers were characterized with a distinctly higher content of isorhamnetin--O-glucoside, astragalin, and (+)-catechin, whereas P.
elatior occurred to be a richer source of rutoside and isorhamnetin--O-rutinoside. Hyperoside was found exclusively in P. e l a t i o r
owers. Phenolic glycosides (primverin and primulaverin) were identied only in the roots. eir content was about ten times
higher in P. v e r i s in comparison with P. e l a t i o r underground organs. e obtained results clearly show that both Primula species
dier distinctly in terms of the content and composition of phenolic compounds. e compounds dierentiating both species to
the highest degree (hyperoside, in owers, as well as primverin and primulaverin, in the roots) may be useful chemical markers in
the identication and evaluation of both species.
1. Introduction
Cowslip (Primula veris L., syn. P. o  c i n a l i s Hill) and oxlip
(Primula elatior (L.) Hill) are small, long-lived perennials
from the family Primulaceae, growing wild in temperate
Europe and Asia []. Cowslip grows on nutrient-poor grass-
lands, herb-rich meadows, and at the edges and in clearings of
warm and bright woodlands. Oxlip prefers moist and shaded
forests,butitalsogrowsinmountainmeadows[,].Both
species produce a rosette of leaves and leaess ower stalks,
up to – cm high. Cowslip owers are fragrant, bright-
yellow with orange spots at the edge of each lobe. ey are
formed at the top of the stalks in an umbel-like inorescence.
In turn, the pale-yellow, almost scentless, owers of oxlip
areproducedonseparatestalks.Inthecentralpartof
these owers an orange ring is visible [, ]. Underground
organs consist of slightly curved, grayish-brown rhizomes
with yellowish-white (P. veris) or brown (P. elatior) roots,
commonly called roots [, ].
Both species have a long history of medicinal use. In the
current (h) edition of the European Pharmacopeia, they
arelistedasasourceofPrimula roots []. However, in the
British Herbal Pharmacopeia [] as well as in Pharmacopee
Franc¸aise [], only P. v e r i s is mentioned as a source of Primula
raw materials.
Primula veris and P. e l a t i o r have mainly been exploited for
the production of herbal teas and preparations that are also
considered dietary supplements []. ey indicate various
pharmacological activities, for example, secretolytic, expec-
torant, anti-inammatory, diuretic, antimicrobial, antifungal,
and sedative [–]. According to EMA, Primula owers and
roots are used against coughs, bronchitis, and catarrhs of the
respiratory tract and also to treat nervousness, headache, or
rheumatism [, ]. In the past, Primula leaves and owers
Hindawi
International Journal of Analytical Chemistry
Volume 2017, Article ID 2871579, 7 pages
https://doi.org/10.1155/2017/2871579
International Journal of Analytical Chemistry
were also eaten raw or cooked as a source of vitamins
and microelements available in late winter []. Apart from
P. v e r i s and P. e l a t i o r ,otherPrimula species are described
as also revealing some medicinal potential. According to
Demir et al. [], P. v u l g a r i s demonstrates antioxidant activity.
Extracts from P. d e n t i c u l a t a show cytostatic properties, while
P. m a c r o p h y l l a shows antifungal ones [–].
e main active compounds of Primula owers and
roots are triterpene saponins as well as phenolic compounds,
including avonoids (about % in owers), phenolic acids,
and phenolic glycosides [, ]. Saponins are responsible
for secretolytic and expectorant activity. In turn, phenolic
compounds, present especially in Primula owers, reveal
antioxidant, antimicrobial, and cytostatic properties [, ].
Phenolic compounds can be easily separated on a C
reversed-phase (RP) column and detected using a UV or
diode array detector (DAD) [–]. All these substances
contain at least one aromatic ring and thus eciently absorb
UV light. So, the UV spectra obtained by the DAD are a
valuableindicatorinscreeningandpreliminaryqualitative
analyses of the dierent groups of phenolics. For better
structure elucidation of metabolites and/or unambiguous
identication of target compounds, liquid chromatography
mass spectrometry (LC-MS) techniques or even nuclear
magnetic resonance (NMR) detection are used [–].
BasedonEuropeanMedicinesAgency(EMA)andEuro-
pean Pharmacopeia monographs, Primula preparations are
produced exclusively out of P. v e r i s and P. e l a t i o r raw materi-
als, which are considered to possess the same values [, , ].
Due to the developmental and morphological similarities
between both species, they are hard to dierentiate on natural
sites, and aer the drying process the raw materials collected
from them are indistinguishable. Despite the above regu-
lations, some authors report dierences between these two
species in terms of their chemical composition [, , ]. Other
herbal raw materials, even those described in pharmacopeias,
are very oen provided by two or even three plant species. For
example, the lime ower is collected from Tilia platyphyllos
Scop., Tilia cordata Mill, and their hybrid Tilia ×vulgaris [].
Numerous studies conrm that the quality of such materials
may be highly diversied, which is undesirable from an
industrial point of view [–].
e aim of our study was to compare wild growing P.
veris and P. e l a t i o r in terms of the accumulation of phenolic
compounds as chemical markers for species identication
and more accurate assessment of raw materials, in the context
of their potential usage, by a simple, but reliable, analytical
method on a standard HPLC-DAD system.
2. Materials and Methods
2.1. Plant Material. Flowers and roots of P. v e r i s and P.
elatior werecollectedintheeasternpartofPolandfrom
eightwildgrowingpopulationsofeachspecies.eplant
material from one population was used as one replication for
chemical evaluation. Flowers were collected at the stage of full
owering (in May, Figures  and ) from randomly chosen
plants (about  g of fresh owers per population). Roots
F : Cowslip (Primula veris).
F : Oxlip (Primula elatior).
were harvested from the same populations in September, aer
seed setting (about  g of fresh roots per population). ey
were washed and cut into pieces. Both sets of raw materials
were dried at C. Voucher specimens were taken from each
population. ese are stored in the Department of Vegetable
and Medicinal Plants, WULS-SGGW.
2.2. HPLC Analysis. Air-dry, nely powdered, and homog-
enized raw material (. g) was extracted with  ml of
methanol (Sigma-Aldrich, Pozna´
n, Poland, reagent grade) in
aB
¨
uchi Labortechnik AG B- Extraction System. Soxhlet
hot extraction was used with twenty-ve extraction cycles,
ushing and drying. Aer evaporation of solvents, the residue
was dissolved in  ml of methanol. e obtained extracts
were ltered with a Supelco Iso-DiskSyringe Tip Filter
Unit, a PTFE membrane, diameter  mm, pore size . 𝜇m
and injected in triplicate. Separation was achieved using
a modern C reversed-phase, Kinetex. 𝜇m,  mm
×. mm column with a porous outer layer on solid
silica core particles (Phenomenex, USA). e analyses were
International Journal of Analytical Chemistry
T : Validation parameters of the HPLC-DAD analysis (𝑛=6).
Compound Purity
(%)
Precision
intraday
(CV, %)
Calibration equation Linearity
(𝑟2)
Linear range
(mg/mL)
LOD
(𝜇g/L)
LOQ
(𝜇g/L)
/+/-Catechin , . 𝑦 = 8216.4𝑥 −6069.3 . .–. . .
Luteolin -C-glucoside (orientin) , . 𝑦 = 2407.3𝑥 −2358.1 . .–. . .
Quercetin -O-rutinoside (rutoside) , . 𝑦 = 1434.0𝑥 − 5093.0 . .–. . .
Quercetin -O-galactoside (hyperoside) , . 𝑦 = 3435.5𝑥 −6882.2 . .–. . .
Isorhamnetin--O-rutinoside , . 𝑦 = 2096.1𝑥 − 904.8 . .–. . .
Isorhamnetin--O-glucoside , . 𝑦 = 1940.0𝑥 −897.4 . .–. . .
Kaempferol -O-glucoside (astragalin) , . 𝑦 = 2104.5𝑥− 2426.3 . .–. . .
-O-Caeoylquinic acid (chlorogenic acid) , . 𝑦 = 6517.4𝑥 −12016.6 . .–. . .
Primverin , . 𝑦 = 12488.0𝑥− 3594.7 . .–. . .
Primulaverin , . 𝑦 = 2785.4𝑥 −5313.2 . .–. . .
performed on a Shimadzu chromatograph equipped with an
SIL-A autosampler, an SPD-MA VP PDA photodiode
array detector, and CLASS VP. chromatography soware
(Shimadzu, Kyoto, Japan). e content of the determined
compounds was calculated in mg per  g of dry weight
(DW).
e analysis of ower extracts was carried out using a
binary gradient of deionized water adjusted to pH  with
phosphoric acid (Sigma-Aldrich, Pozna´
n, Poland, reagent
grade) (mobile phase A) and ACN (Sigma-Aldrich, Pozna´
n,
Poland, gradient grade) (mobile phase B) as follows: . min,
.% B; . min, % B; . min, % B; . min, .% B;
 min, stop. e ow rate was . ml/min, oven temperature
C and injection volume 𝜇l. Data were recorded at
wavelength of  nm for (+)-catechin,  nm for luteolin
-C-glucoside (orientin), quercetin -O-rutinoside (ruto-
side), quercetin -O-galactoside (hyperoside), isorhamnetin-
-O-rutinoside, isorhamnetin--O-glucoside,  nm for
kaempferol -O-glucoside (astragalin), and  nm for -O-
caeoylquinic acid (chlorogenic acid).
For separation of root extract compounds, a binary
gradient of deionized water adjusted to pH  with phosphoric
acid (Sigma-Aldrich, Pozna´
n, Poland, reagent grade) (mobile
phase A) and ACN (Sigma-Aldrich, Pozna´
n, Poland, gradient
grade) (mobile phase B) was used as follows: . min, % B;
. min, % B; . min, % B; . min, % B; . min,
% B,  min, stop. e ow rate was . ml/min, oven
temperature C, and injection volume 𝜇l. Compounds
were monitored at wavelength of  nm for primverin and
 nm for primulaverin.
Peak identication was conrmed by comparison of re-
tention time and UV spectra with adequate parameters of
standards. Commercially available standards of the investi-
gated compounds (ChromaDex, Irvine, USA) were
separately dissolved with methanol (Sigma-Aldrich, Pozna´
n,
Poland) in a  ml volumetric ask according to the Chro-
maDex’s Tech Tip : Reference Standard Recovery and
Dilutionandthenusedasstandardstocksolutions(https://
ww w.chromadex.com/media//techtip-recoverydilu-
tionprocedures nl pw.pdf). Working standard solutions were
prepared by dilution of , , , , , or  𝜇lstock
solutions of each compound with methanol in  ml
volumetric asks. e working solutions were injected
(. 𝜇l)onacolumninsixreplicates(𝑛=6)usingSIL-A
autosampler (Shimadzu, Kyoto, Japan) to generate a six-point
calibrationcurve.Standardcurveparameterswerecalculated
using Microso Excel  (Table ). e signal-to-noise (S/N)
ratio approach was used to determine LOD (S/N of : ) and
LOQ (S/N of  : ).
2.3. Statistical Analysis. Data were subjected to statistical
analysis using Statgraphics Plus for Windows v. . soware.
e mean values were compared using one-way analysis of
variance (ANOVA) and expressed as means with standard
deviation (SD) and coecients of variation (CV%). e
dierences between individual means were considered to be
signicant at 𝑝 < 0.01.
3. Results and Discussion
According to Wichtl [], the total content of avonoids in
Primula owers is up to about %. To date in P. v e r i s extracts,
quercetin, quercetin--O-rutinoside, quercetin--O-gentio-
bioside, quercetin-trihexoside, kaempferol, kaempferol--O-
diglucoside--O-glucoside, kaempferol--rutinoside, kaemp-
ferol--O-galactoside-rhamnoside--O-rhamnoside, luteolin,
isorhamnetin, isorhamnetin--O-glucoside, isorhamnetin-
-O-rutinoside, limocitrin--O-glucoside, limocitrin--O-
rutinoside, apigenin, catechin, epicatechin, and epigallocat-
echin, as well as some methoxylated avones, have been
identied using LC-MS and HPLC techniques [–, , ].
Data on the composition of P. e l a t i o r owers are much more
scarce. ese indicate the presence of rutoside, kaempferol-
-rutinoside, and isorhamnetin--glucoside [].
e above authors report only the chemical composition
of avonoids isolated from both Primula owers. ere
is little information on the content of those substances.
According to Wichtl [], owers of P. e l a t i o r are characterized
by a higher content of rutoside (.%) than the owers
of P. v e r i s (.%). Our results conrm the presence of six
International Journal of Analytical Chemistry
T : e content of identied phenolic compounds in P. v e r i s and P. e l a t i o r owers (mg/ g DW).
Identied phenolic compounds P. v e r i s P. e l a t i o r
Mean ±sd CV (%) Mean ±sd CV (%)
(+)-Catechin . ±.1∗∗ . . ±. .
Orientin . ±. ns . . ±. .
Rutoside . ±. . . ±.1∗∗ .
Hyperoside nd . ±. .
Isorhamnetin--O-rutinoside . ±. . . ±.6∗∗ .
Isorhamnetin--O-glucoside . ±.9∗∗ . . ±. .
Astragalin . ±.9∗∗ . . ±. .
Chlorogenic acid . ±. ns . . ±. .
Values are the mean ±standard deviation (𝑛=8); ∗∗𝑝<0.01, ns: insignicant dierence, nd: not detected, and CV: coecient of variation.
Orientin
Rutoside
Astragalin
(+)-Catechin
Isorhamnetin-3-O-rutinoside
Isorhamnetin-3-O-glucoside
Chlorogenic acid
Spectrum max plot
123456789100
(Minutes)
0
100
200
300
400
500
600
(mAu)
0
100
200
300
400
500
600
(mAu)
F : HPLC chromatogram of methanolic extract of the owers
of Primula veris.
avonoid compounds in the owers of both species, namely,
orientin (luteolin--C-glucoside), rutoside (quercetin -
O-rutinoside), isorhamnetin--O-rutinoside, isorhamnetin-
-O-glucoside, astragalin (kaempferol--O-glucoside), and
(+)-catechin. e contents of isorhamnetin--O-glucoside,
astragalin, and (+)-catechin were distinctly higher in the
owers of P. v e r i s , that is, ., ., and . mg/ g
DW,respectively.Inturn,rutosideandisorhamnetin--O-
rutinoside were detected in higher amounts in P. e l a t i o r
(. and . mg/ g DW, resp.). A clear dierence
between both species concerned the presence of hyperoside
(quercetin -O-galactoside), which was only identied in
P. e l a t i o r owers (. mg/ g DW) (Table , Figures
and ). Among the analyzed substances, the content of this
compound was also the most diversied (CV .%).
According to Kim et al. [], hyperoside indicates anti-
inammatory and antioxidant activities. Results obtained by
Wuetal.[]showthatthiscompoundrevealsantiviral
activity, while Kohlm˝
unzer [] also mentions diuretic and
hypotensiveeects.Inturn,rutosideisknownforitsstrong
antioxidant potential as well as antimicrobial and anti-
inammatory activities []. us, this may explain the appli-
cation of owers of both Primula species in the treatment
of coughs and respiratory tract diseases. e results of this
study show that both hyperoside and rutoside dierentiated
the investigated species to a considerable degree. erefore,
owers of P. e l a t i o r , which are rich in hyperoside and
Orientin
Rutoside
Hyperoside
Astragalin
(+)-Catechin
Isorhamnetin-3-O-rutinoside
Isorhamnetin-3-O-glucoside
Chlorogenic acid
Spectrum max plot
123456789100
(Minutes)
0
100
200
300
400
500
600
(mAu)
0
100
200
300
400
500
600
(mAu)
F : HPLC chromatogram of methanolic extract of the owers
of Primula elatior.
characterized by a higher content of rutoside in comparison
to P. v e r i s , may indicate stronger pharmacological activity.
Unlike in the data presented by Wichtl [], both species
contained isorhamnetin--glucoside in their owers (Table ,
Figures  and ). Similar to hyperoside, the diversity of
the content of both isorhamnetin derivatives was very high.
However, the content of isorhamnetin--O-rutinoside was
diversied to a higher degree for P. v e r i s (CV .%), while
for isorhamnetin--O-glucoside this was seen in P. e l a t i o r
(CV .%). According to Teng et al. [], isorhamnetin
aglycon reveals cytotoxic activity toward human hepatocellu-
lar carcinoma cells. In our study, the presence of one phenolic
acid (chlorogenic acid) in both Primula owers was also
conrmed, and its content was similar in P. v e r i s and P. e l a t i o r
(. and . mg/ g DW, resp.).
Primverin and primulaverin (phenolic glycosides) are
typical compounds of P. v e r i s and P. e l a t i o r underground
organs.epresenceofthesesubstancesinPrimula roots had
been previously conrmed by M¨
ulleretal.[].Accordingto
EMA [], their content in both species is very diversied and
maybeashighas.%.eyareresponsibleforthespecic
odor of the raw material, which appears during the drying
process []. In our study, the content of both compounds
was ten times higher in P. v e r i s (. and . mg/ g
DW, resp.) than in P. e l a t i o r (. and . mg/ g DW,
resp.) roots (Table , Figures  and ). Such a relationship had
previously been reported only for primverin []. In addition,
International Journal of Analytical Chemistry
T : e content of identied phenolic compounds in P. v e r i s and P. e l a t i o r roots (mg/  g DW).
Identied phenolic compounds P. v e r i s P. e l a ti o r
Mean ±sd CV (%) Mean ±sd CV (%)
Primverin . ±.2∗∗ . . ±. .
Primulaverin . ±.2∗∗ . . ±. .
Values are the mean ±standard deviation (𝑛=8); ∗∗𝑝<0.01, CV: coecient of variation.
Primverin
Primulaverin
0,25
0,50
0,75
1,00
1,25
1,50
1,75
2,00
2,25
2,50
2,75
3,00
3,25
3,50
3,75
4,00
4,25
4,50
4,75
5,00
0,00
(Minutes)
0
20
40
60
80
100
120
140
160
180
200
(mAu)
0
20
40
60
80
100
120
140
160
180
200
(mAu)
002 v
Detector 1–254 nm
F : HPLC chromatogram of methanolic extract of the roots
of Primula veris.
Primverin
Primulaverin
0,25
0,50
0,75
1,00
1,25
1,50
1,75
2,00
2,25
2,50
2,75
3,00
3,25
3,50
3,75
4,00
4,25
4,50
4,75
5,00
0,00
(Minutes)
0
20
40
60
80
100
120
140
160
180
200
(mAu)
0
20
40
60
80
100
120
140
160
180
200
(mAu)
Detector 1–254 nm
001 K
F : HPLC chromatogram of methanolic extract of the roots
of Primula elatior.
the results of our study conrm that the content of primverin
was much less diversied in both species than the content of
primulaverin (Table ).
According to our results, the use of a column with
porous outer layer on solid silica core particles signicantly
reduces the analysis time and mobile phase consumption
in comparison to existing methods [, ]. As a result, the
analysis of phenolics in Primula raw materials can be eected
faster and at lower cost and can be performed on standard
(older) chromatographic systems.
e data concerning the chemical prole of other Primula
species are fragmentary. Hashimoto et al. [] identied
three avonol glycosides in P. s i e b o l d i i owers and leaves,
that is, quercetin and kaempferol derivatives, as well as two
anthocyanins, that is, malvidin and petunidin glycosides,
which were detected only in the owers. In turn, Ozkan et
al. [] used HPLC to assess the content of catechin, rutin,
and some phenolic acids, namely, gallic, protocatechuic, p-
OH benzoic, vanillic, and p-coumaric acids in P. v u l g a r i s
owers. According to this analysis, rutin and p-coumaric
acidseemedtobethemainphenoliccompoundofthisraw
material. In other Primula species, that is, P. d e n t i c u l a t a ,P.
auricular,P. h a l l e r i ,P. m a l a c o i d e s ,andP. marginata,primetin
(,-dihydroxyavone), which is responsible for strong sen-
sitizing properties, was also detected []. Depending on
the chemical composition and content of biologically active
compounds, dierent plant species of the genus have been
used for various medicinal purposes, such as food poisoning,
indigestion, dysentery, and ulcers as well as coughs or
bronchitis, which are typical ailments treated with P. v e r i s and
P. e l a t i o r extracts.
4. Conclusions
Our results show distinct dierences in terms of the content
and composition of phenolic compounds identied in P. v e r i s
and P. e l a t i o r raw materials. Primula elatior owers seem to be
an interesting source of avonoids. ey are rich in rutoside
and hyperoside, which reveal numerous pharmacological
activities, that is, anti-inammatory, antioxidant, and antimi-
crobial. us, they can be considered more interesting for the
herbal medicine industry than P. v e r i s .Inturn,hyperoside
was only found in the owers of P. e l a t i o r ,whichmaybe
used in the identication of Primula species. Flowers of
neither species contained primverin or primulaverin. ese
substances were only identied in the roots. Primula veris was
characterized by a ten times higher content of both phenolic
glycosides in comparison with P. e l a t i o r .
Phenolic compounds identied in our study, especially
hyperoside, primverin, and primulaverin, may be applied as
chemical markers in the identication of Primula species as
well as quality markers for their raw materials sourced from
both natural sites and cultivated ones. e proposed analyt-
ical methods for the determination of these compounds in
plant material are fast and reliable and can be performed on
every standard HPLC system.
International Journal of Analytical Chemistry
Conflicts of Interest
e authors declare that there are no conicts of interest
regarding the publication of this paper.
Acknowledgments
e studies were supported by the Polish Ministry of Agri-
culture and Rural Development, within the Multiannual
Programme “Creating the Scientic Basis of the Biological
Progress and Conservation of Plant Genetic Resources as a
Source of Innovation to Support Sustainable Agriculture and
Food Security of the Country –.”
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... kiadás). A növény minden része, főleg a drogként alkalmazott gyökeres gyöktörzse szaponinban gazdag, a föld feletti részei, virága és levele polifenolos vegyületekben, flavonoidokban bővelkedik [1,2,3,4]. A múltban a Primula leveleit és virágait nyersen vagy főzve is fogyasztották vitamin-és mikroelem forrásként. ...
... A Primula veris drogok polifenoljai esetében az etanol bizonyult a leghatékonyabb kivonószernek mindhárom drog esetében. A kapott eredmények alapján legnagyobb mennyiségben a virágdrog etanolos kivonata tartalmaz polifenolokat (481,57 mg GAE/100 g), hasonlóan a szakirodalmi adatokhoz, melyek szintén a virágban lévő kiemelkedő polifenol tartalmat bizonyítják [3,9,10]. A virág polifenol tartalmát (481,57 mg GAE/100 g) a levéldrog etanolos kivonata követi (339,47 mg GAE/100 g) koncentrációval, míg a gyökér etanolos kivonata tartalmazza a legkevesebb hatóanyagot 256,05 mg/100 g. ...
... Az "in vitro" ABTS antioxidáns kapacitás vizsgálat eredményei szerint az etanolos kivonatok bizonyultak jobbnak a vizes kivonatokhoz képest. A legjobb szabadgyökfogó képeséggel a gyökér 50 %-os etanolos kivonatai rendelkeznek, ellentétben a szakirodalomi adatokkal, ahol a virágdrog antioxidáns hatása kiemelkedő [3,9]. ...
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... In turn, Müller et al. [43], in their studies covering methanolic extracts derived from the dried roots and flowers of two Primula species, showed the presence of five bioactive compounds, including three saponins and two phenolic glycosides, of which the predominant component was primeverine, found in the aerial parts of the test plant, while in the root extracts saponins were predominant, mainly priverosaponin B-22-acetate, which, according to the authors of these studies, confirms previous reports on the profile of saponins from the various morphological parts of Primula veris L. Similar studies were performed by Bączek et al. [4] by comparing the raw materials of wild Primula veris L. and Primula elatior (L.) Hill in terms of the profile of phenolic compounds and their concentrations using the HPLC-DAD method. The results of their analyses confirmed that the flowers of both species are rich in flavonoids, but Primula veris L. was characterized by a significantly higher content of isorhamnetin-3-O-glucoside, astragalin, and (+)-catechin, whereas Primula elatior proved to be a richer source of rutoside and isorhamnetin-3-O-rutinoside. ...
... The authors of the studies also pointed out that both species were characterized by a high rutinoside content in the range of 630.83 to 1025.96 mg/100 g dry weight, which is known to exhibit numerous anti-inflammatory, anti-oxidative, and anti-bacterial properties. In turn, our own studies showed twice the rutinoside content in the extracts analyzed compared to Bączek et al. [4], who additionally confirmed the presence of phenolic glycosides (primeverine and primulaverine) only in the plant's roots and not in aerial parts as other authors of research had determined [43], and their content was approximately ten times higher in Primula veris L. compared to the underground parts of Primula elatior. In the summary of the observations carried out, the same authors concluded that both Primula species were different in content and composition of phenolic compounds and that the substances most differentiating both species could be useful chemical markers for the identification and evaluation of these species. ...
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Our experiments may help to answer the question of whether cowslip (Primula veris L.) is a rich source of bioactive substances that can be obtained by efficient extraction with potential use as a food additive. A hypothesis assumed that the type of solvent used for plant extraction and the individual morphological parts of Primula veris L. used for the preparation of herbal extracts will have key impacts on the efficiency of the extraction of bioactive compounds, and thus, the health-promoting quality of plant concentrates produced. Most analysis of such polyphenolic compound contents in extracts from Primula veris L. has been performed by using chromatography methods such as ultra-performance reverse-phase liquid chromatography (UPLC−PDA−MS/MS). Experiments demonstrated that the most effective extraction agent for fresh study material was water at 100 °C, whereas for dried material it was 70% ethanol. The richest sources of polyphenolic compounds were found in cowslip primrose flowers and leaves. The aqueous and ethanol extracts from Primula veris L. were characterized by a quantitatively rich profile of polyphenolic substances, and a high antioxidative potential. Selective extraction with the use of mild conditions and neutral solvents is the first step to obtaining preparations from cowslip primrose with a high content of bioactive substances.
... Presently, cowslip is less abundant in Europe than in the past, and the sustainable supply of the source material has become more difficult [7,8]. The species is included in the European Red List of Medicinal plants under the category "Least Concern" [9]; however, according to the European Pharmacopoeia, it is still used as a source of Primula roots together with P. elatior [10]. In Poland, some of the natural populations of P. veris are endangered as a result of plowing, grazing, digging up for decorative purposes, and the species being under partial legal protection [11]. ...
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Primula veris is a valuable medicinal plant species with declining populations, protected in Bulgaria by the Biodiversity Act. The present study aimed to increase its extremely low seed germination rate, starting with seeds originating from two Bulgarian populations, and to set up an ex situ field collection. The stimulation effect of three factors was tested in in vivo and in vitro experiments: seeds treated with gibberellic acid (in different concentrations and exposure time), light quality (white, infrared, red, and blue or dark), and cold stratification. The combination of factors resulted in 36 treatment variants in vivo and 8 treatment variants in vitro. No germination was observed in control treatment variants. The highest germinating rate (95%) was noticed in vivo under blue monochromatic light after seed soaking into 0.2% GA3 for 10 h; however, the best results (55% of well-developed seedlings) were observed with a combination of blue light and 0.3% GA3 for 5 h. Seedlings were successfully strengthened in vermiculite in a phytotron, potted in soil and grown in a greenhouse, and then 75 plants were transferred to the field plot, where most of them bloomed at the first vegetation season. These results are intended to serve as a basis for establishing a pilot agriculture of the species.
... Valuable sources of biologically active substances are members of the Primulaceae family, in particular the genus Primula (Primula L.), species of which are used in many countries around the world [1], [2]. Plants of the genus Primrose have played an important role in the treatment of diseases of the upper respiratory tract [3], primarily due to the diverse number of active substances: saponins, flavonoids, essential oil, tannins, vitamins, and unlimited base of raw materials [4], [5]. ...
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BACKGROUND: At present, coughing can be regulated by medications such as dextromethorphan and codeine, which are associated with side effects, including drug drowsiness or dependency. Thus, there is an increasing demand for drugs that promote expectorant activities with fewer adverse effects. The root of Primula veris L. (Primulaceae) is an herbal medicine that has been used as an expectorant drug for thousands of years in folk medicine. AIM: The present study aims to create an in-depth pharmacological study of the expectorant activity of P. veris to create new drugs in different directions which are appropriate and promising. MATERIALS AND METHODS: The expectorant effect of thick extracts of the study plant was studied on the influence of the motor activity of the ciliated epithelium and the secretory function of the bronchi. The expectorant activities of the ethanol extracts of leaves and rhizomes with roots from P. veris were evaluated using classical animal models. The expectorant assay was performed with phenol red secretion in the mouse trachea. After gastric administration of the test extracts in mice, 2.5% phenol red solution was injected intraperitoneally. The trachea was dissected and the optical density of tracheal secretion was measured. RESULTS: The results of the studies showed that a thick extract of primrose rhizomes with roots has a high ability to secrete sputum, which is almost not inferior to the Hedelix drops comparator (ivy extract) – 126.6% and 146.4%, respectively. Extract from the leaves of P. veris is characterized by less pronounced activity, which, at a dose of 200 mg/kg, was 74.5%. CONCLUSION: The results of the present study provide evidence that P. veris can be used as an expectorant herbal medicine and that triterpene saponins may be the main active ingredients of Primula veris responsible for its bioactivities.
... Most recently, for the first time discovered in a natural source, several flavones, substituted only in the B ring, have been found in the wax of P. veris (Budzianowski et al., 2005). The waxes/farinas of this taxon have been investigated for the presence/structural elucidation of flavonoids from several regions (Valant-Vetschera et al., 2009;Shostak et al., 2016;Apel et al., 2017;Bᶏczek et al., 2017), but never previously from Serbia. ...
Article
Herein, the results of the first study of non-flavonoid constituents of aboveground surface-wax washings of Primula veris L. (Primulaceae) are presented. Chromatography of the washings yielded a minor fraction composed of n-, iso-, and anteiso-series of long-chained syn-1-phenylalkane-1,3-diyl diacetates, 3-oxo-1-phenylalkan-1-yl acetates, 1-phenylalkane-1,3-diones, 1-hydroxy-1-phenylalkan-3-ones, sec-alcohols (2- to 10-alkanols), and n-, iso-, anteiso-, 2-methylalkanoic and 3-methylalkanoic acids; 118 of these constituents represent up to now unreported natural compounds. The structural/stereochemical elucidation was accomplished by the synthesis of authentic standards, derivatization reactions, the use of gas chromatographic retention data and detailed 1D and 2D-NMR analyses of the obtained complex chromatographic fraction. Primula veris produces unusually high amounts of branched long-chained metabolites (>60%) except for the fatty acids where the percentage of branched isomers is comparable to the ones with n-chains. Noteworthy is the fact that long-chained α- and β-methyl substituted fatty acids were detected herein for the first time in the kingdom Plantae.
... Chemical composition. Saponins (e.g., primulasaponin I, primulasaponin II) (Müller et al., 2006); flavonoids (e.g., quercetin, luteolin, kaempferol, and isorhamnetin derivatives); phenolic acids (e.g., chlorogenic acid) (Bączek et al., 2017). ...
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Background: Current recommendations for the self-management of SARS-Cov-2 disease (COVID-19) include self-isolation, rest, hydration, and the use of NSAID in case of high fever only. It is expected that many patients will add other symptomatic/adjuvant treatments, such as herbal medicines. Aims: To provide a benefits/risks assessment of selected herbal medicines traditionally indicated for “respiratory diseases” within the current frame of the COVID-19 pandemic as an adjuvant treatment. Method: The plant selection was primarily based on species listed by the WHO and EMA, but some other herbal remedies were considered due to their widespread use in respiratory conditions. Preclinical and clinical data on their efficacy and safety were collected from authoritative sources. The target population were adults with early and mild flu symptoms without underlying conditions. These were evaluated according to a modified PrOACT-URL method with paracetamol, ibuprofen, and codeine as reference drugs. The benefits/risks balance of the treatments was classified as positive, promising, negative, and unknown. Results: A total of 39 herbal medicines were identified as very likely to appeal to the COVID-19 patient. According to our method, the benefits/risks assessment of the herbal medicines was found to be positive in 5 cases (Althaea officinalis, Commiphora molmol, Glycyrrhiza glabra, Hedera helix, and Sambucus nigra), promising in 12 cases (Allium sativum, Andrographis paniculata, Echinacea angustifolia, Echinacea purpurea, Eucalyptus globulus essential oil, Justicia pectoralis, Magnolia officinalis, Mikania glomerata, Pelargonium sidoides, Pimpinella anisum, Salix sp, Zingiber officinale), and unknown for the rest. On the same grounds, only ibuprofen resulted promising, but we could not find compelling evidence to endorse the use of paracetamol and/or codeine. Conclusions: Our work suggests that several herbal medicines have safety margins superior to those of reference drugs and enough levels of evidence to start a clinical discussion about their potential use as adjuvants in the treatment of early/mild common flu in otherwise healthy adults within the context of COVID-19. While these herbal medicines will not cure or prevent the flu, they may both improve general patient well-being and offer them an opportunity to personalize the therapeutic approaches.
Article
Primula vulgaris Huds. leaves and roots were used to treat skin damage and inflammation in Anatolian Folk Medicine. This study aimed to assess the ethnopharmacological use of the plant using in vivo, in vitro, and in silico test models. Linear incision and circular excision wound models were used to determine the in vivo wound‐healing potential of the plant extracts and fractions. In vitro assays including hyaluronidase, collagenase, and elastase inhibitory activities were carried out for the active compounds to discover their activity pathways. Structure‐based molecular modeling was performed to understand inhibitory mechanisms regarding collagenase and elastase at the molecular level. The n‐butanol fraction of the roots of P. vulgaris showed the highest wound‐healing activity. Through activity‐guided fractionation and isolation techniques, primulasaponin I (1) and primulasaponin I methyl ester (2) were stated as the major active compounds. These compounds exerted their activities through the inhibition of collagenase and elastase enzymes. Primulasaponin I methyl ester isolated from n‐butanol fraction was found to be the strongest agent, especially with the values of 29.65% on collagenase and 38.92% on elastase inhibitory activity assays, as well as molecular docking studies. The present study supports scientific data for the traditional use of P. vulgaris and the wound healing properties of the plant can be referred to secondary metabolites as especially saponins found in the roots.
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Primula veris (Primulaceae) is a valuable medicinal plant. The main characteristics for assessing the reproductive potential (embryological features; mode of reproduction; pollen and seed viability) and the genetic diversity of populations of the species from Bulgaria were studied. The anthers are tetrasporangiate. Their wall development follows the Dicotyledonous-type and consists of: epidermis, a fibrous endothecium, an ephemeral middle layer and a secretory (glandular) tapetum. After meiosis in pollen mother cells and simultaneous microsporogenesis tetrahedral tetrads are formed predominantly in the anthers. Many ovules (approximately 20) develop in the unilocular ovary and are anatropous, tenuinucellate and bitegmic. The embryo sac (ES) develops after Polygonum (monosporic)-type from the chalazal cell of linear megaspore tetrad in the ovule. After double fertilization, a Caryophyllad-type embryo and initially nuclear endosperm form. In the studied populations, high pollen viability of more than 95% was established. Extremely low viability (about 4%) of the seeds obtained from natural populations was established. The results reveal P. veris to be a predominantly amphimictic (sexually reproducing) species, although rare vegetative propagation is also observed. As a result of this study, essential data were obtained about the reproductive structures and processes and for assessing the reproductive potential of P. veris.
Article
An HPLC-PDA method was developed for the determination of the flavonoids in the flowers of Primula veris from Epirus, Greece. The aim was to investigate the chemical content of the over-harvested P. veris populations of Epirus and to develop and optimize an extraction protocol to allow fast, exhaustive, and repeatable extraction. Qualitative analysis revealed that the P. veris flowers from Epirus were particularly rich in flavonoids, especially flavonol triglycosides including derivatives of quercetin, isorhamnetin, and kaempferol. A phytochemical investigation of a 70% hydromethanolic extract from the flowers afforded a new flavonoid, namely, isorhamnetin-3-Ο-β-glucopyranosyl-(1 → 2)-β-glucopyranosyl-(1 → 6)-β-glucopyranoside, which is also the main constituent of the flower extracts. Its structure elucidation was carried out by means of 1D and 2D NMR and mass spectrometry analyses. The HPLC-PDA method was developed and validated according to the International Council for Harmonisation guidelines. Since the main flavonol glycoside of the plant is not commercially available, rutin was used as a secondary standard and the response correction factor was determined. Finally, the overall method was validated for precision (% relative standard deviation ranging between 1.58 and 4.85) and accuracy at three concentration levels. The recovery ranged between 93.5 and 102.1% with relative standard deviation values < 5%, within the acceptable limits. The developed assay is fast and simple and will allow for the quality control of the herbal drug.
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Primula veris L. is an important medicinal plant with documented use for the treatment of gout, headache and migraine reaching back to the Middle Ages. Triterpenoid saponins from roots and flowers are used in up-to-date phytotherapeutic treatment of bronchitis and colds due to their expectorant and secretolytic effects. In addition to the wild type plants with yellow petals, a red variant and an intermediate orange form of Primula veris L. have recently been found in a natural habitat. The secondary metabolite profiles of roots, leaves and flowers of these rare variants were investigated and compared with the wild type metabolome. Two flavonoids, six flavonoid glycosides, four novel methylated flavonoid glycosides, five anthocyanins and three triterpenoid saponins were identified in alcoholic extracts from the petals, leaves and roots of the three variants by high performance liquid chromatography (HPLC)-diode array detection (DAD)/mass spectrometry (MSⁿ) analyses. Anthocyanins were detected in the petals of the red and orange variety, but not in the wild type. No other effects on the metabolite profiles of the three varieties have been observed. The possibility is discussed that a regulatory step of the anthocyanin biosynthetic pathway may have been affected by mutation thus triggering color polymorphism in the petals.
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The present study was designed to evaluate the phytochemical composition, antimicrobial and radical-scavenging activities of ethanolic extract of Primula denticulata- an important medicinal herb of Kashmir Himalaya. Phytochemical study was performed by using various standard phytochemical methods. Free radical scavenging activities of the extract was assessed by employing different in vitro assays such as DPPH free radical scavenging assay, hydrogen peroxide scavenging activity and lipid per oxidation assay. Calf thymus DNA was also monitored by TBARS formation. The results were compared with standard antioxidant (α-tocopherol). Antibacterial activity of the extract was determined by agar well diffusion method. DPPH free radical scavenging assay and hydrogen peroxide scavenging activity revealed plant extract to be an active radical scavenger. P.denticulata extract also dose dependently inhibited the MDA formation or lipid per oxidation and as such might intercept the free radical chain of oxidation. The leaf extract also prevents calf thymus DNA from oxidative damage induced by hydroxyl radical generated by FeSO4 and H2O2 in Fenton reaction. The hydroxyl radical quenching ability of polyphenolic compounds of Primula denticulata could be responsible for the protection against oxidative damage to DNA. The ethanolic extract showed anti-microbial activity which was visible as the zones of inhibition formed in the different cultures of Gram positive and Gram negative bacteria as well as in case of fungal cultures. Among all the maximum activity was seen for Escherichia coli with inhibition zone diameter of 23.53 ± 3.71mm followed by Klebsiella pneumoniae with inhibition zone diameter of 20.74 ± 3.33mm. These findings provide evidence that the considered plant possesses antimicrobial and antioxidant properties and may act as possible antioxidant for biological systems susceptible to free radical-mediated reactions.
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Primula is a plant genus which comprises about 400 species. It has been found in a number of pharmacological studies that primrose extracts are rich in saponins. Phenolic glycosides and saponins are characteristic compounds for the genus Primula. In this study several flower extracts from Primula veris L. has been tested for antibacterial activity and decoction from the flowers has been tested for antimitotic activity. Antibacterial activity was determined by the well diffusion method and Allium cepa L. has been used for evaluating cytotoxicity. Decoction of flowers was toxic on root number and root length in A. cepa L. and reduced the mitotic index significantly. All of the tested P. veris L. extracts showed inhibitory effect against both Gram positive and Gram negative microorganisms at varying degrees. The most effective fraction was found to be the ethanolic.
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In this research, essential oil yield and composition, total phenolic, flavonioid content and antioxidant activity of eight Achillea (A. vermicularis, A. nobilis, A. wilhelmsii, A. millefolium, A. filipendulina, A. tenuifolia, A. biebersteinii and A. eriophora) species were compared. The essential oil yield of the leaves ranged from 0.35 % in A. wilhelmsii to 1.5 % in A. biebersteinii. GC-MS analyses revealed 40 compounds in leaves of eight Achillea species. The main constituents were 1,8-cineole, germacrene-D, camphor, borneol and spathulenol. Total phenolic content (TPC) varied from 13.56 in A. biebersteinii to 188.66 mg/1g of dry weight in A. wilhelmsii while, total flavonoid content (TFC) ranged from 19.23 in A. eriophora to 79.16 (mg Quercetin/gdW) in A. biebersteinii. Antioxidant activity of methanolic extract was evaluated according to 1,1-diphenyl-2-picrylhydrazy (DPPH), ferric thiocyanate (FTC) and β-carotene-linoleic acid assay. In DPPH assay, A. eriophora showed the highest Ic50 (1172 µg/ml), while A. biebersteinii possessed the lowest one (179 µg/ml). For reducing power, the highest and the lowest absorbance in 700 nm belonged to A. tenuifolia (2.311) and A. wilhelmsii (0.306), respectively. Cluster analysis of Achillea species based on their major secondary metabolites were also classified the species in to three groups. Finally, comparison of studied species introduced A. biebresteinii as a good source of essential oil, flavonoid content and high antioxidant activity.
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Three flavonol glycosides were isolated from the leaves of Primula sieboldii. They were identified as quercetin 3-O-β-[xylopyranosyl-(1-->2)-β- glucopyranosyl-(1-->6)-β-glucopyranoside] (1), kaempferol 3-O-β-[glucopyranosyl-(1-->2)-β-glucopyranosyl-(1-->6)-β-glucopyranoside] (2) and kaempferol 3- O-β-[xylopyranosyl-(1-->2)-β-glucopyranosyl-(1-->6)-β-glucopyranoside] (3). Their chemical structures were determined by UV, 1H and 13C NMR spectroscopy, LC-MS and acid hydrolysis. Compounds 1 and 3 are found in nature for the first time. They were also detected in the flowers, together with two anthocyanins, malvidin 3,5-di-O-glucoside and a minor petunidin dihexoside.
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Hyperoside (quercetin-3-O-galactoside) is a flavonoid compound mainly found in the herb plants Hypericum perforatum L and Crataegus pinnatifida. Although hyperoside has a variety of pharmacological effects including anti-viral, anti-oxidative, and anti-apoptotic activities, the anti-inflammatory mechanism of hyperoside in mouse peritoneal macrophages remains unclear. In this study, hyperoside was shown to exert an anti-inflammatory action through suppressed production of tumor necrosis factor, interleukin-6, and nitric oxide in lipopolysaccharide-stimulated mouse peritoneal macrophages. The maximal inhibition rate of tumor necrosis factor-α, interleukin-6, and nitric oxide production by 5 μM hyperoside was 32.31 ± 2.8%, 41.31 ± 3.1%, and 30.31 ± 4.1%, respectively. In addition, hyperoside inhibited nuclear factor-κB activation and IκB-α degradation. The present study suggests that an important molecular mechanism by hyperoside reduces inflammation, which might explain its beneficial effect in the regulation of inflammatory reactions.
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Ethnopharmacological relevance: Rutin is a common dietary flavonoid that is widely consumed from plant-derived beverages and foods as traditional and folkloric medicine worldwide. Rutin is believed to exhibit significant pharmacological activities, including anti-oxidation, anti-inflammation, anti-diabetic, anti-adipogenic, neuroprotective and hormone therapy. Till date, over 130 registered therapeutic medicinal preparations are containing rutin in their formulations. This article aims to critically review the extraction methods for plant-based rutin and its pharmacological activities. This review provides comprehensive data on the performance of rutin extraction methods and the extent of its pharmacological activities using various in vitro and in vivo experimental models. Materials and methods: Literatures including journals, patents, books and leaflets reporting on rutin from natural resources are systematically reviewed, particularly in the aspect of its extraction methods and biological activities. Factors affecting the efficiency of rutin extraction such as extraction temperature, duration and solvent to sample ratio are presented based on the findings of previous studies. The observed biological activities followed by clear explanation are also provided accordingly. Results: The biological activities of rutin varied largely dependent on the geographical and plant origins. The complexity of natural rutin has impeded the development of rutin derived drugs. The detail mechanism of rutin in human body after consumption is still unclear. Therefore, studies are intensively carried out both in vitro and in vivo for the better understanding of the underlying mechanism. The studies are not limited to the pharmacological properties, but also on the extraction methods of rutin. Many studies have focused on the optimization of extraction method to increase the extraction yield of rutin. Currently, the performances of modern extraction approaches have also been compared to the conventional heat reflux method as a benchmark. Conclusion: There are various extraction methods for plant-based rutin ranging from conventional method up to the use of modern techniques such as ultrasound, mechanochemical, microwave, infrared and pressurized assisted methods. However, proper comparison between the methods is very difficult because of the variance in plant origin and extraction conditions. It is important to optimize the extraction method in order to produce high yield and acceptable purity of rutin with a reasonable cost. Even though rutin has been proven to be effective in numerous pharmacological activities, the dosage and toxicity of rutin for such activities are still unknown. Future research should relate the dosage and toxicity of rutin for the ethnobotanical claims based on the underlying mechanisms.
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Given the frequent movement of commercial plants outside their native location, the consistent and standard use of plant names for proper identification and communication has become increasingly important. This second edition of World Economic Plants: A Standard Reference is a key tool in the maintenance of standards for the basic science underlying the quest for security of food and other economic plant resources. Containing a substantial increase in content from the previous edition, this comprehensive and accessible work now documents more than 12,000 economically important vascular plants. This volume covers plants and plant products that are traded, regulated, or otherwise important to international commerce. The plant names and uses have been meticulously checked against the literature and by external peer reviewers, and names are up to date in their taxonomic classification and nomenclaturally correct according to international rules. Each entry includes the accepted scientific (Latin) name, synonyms, economic importance, common names in a variety of languages, and the geographical distribution of the species. The information on each plant can be accessed through either its scientific or common name, providing a global perspective on its native, introduced, or cultivated geographical distribution, and its economic usage or impacts. This reference covers all major groups of economic plants, including those used for human or animal food, materials, medicines, environmental purposes, gene sources for breeding, social purposes, as well as ones with negative impacts such as poisonous or disease-harboring plants or weeds. This compilation provides scientists, professionals, and students from various backgrounds with a global standard for communication regarding economically important plants. As collaboration across plant science increases, comprehensive standardized references such as this one are indispensable for addressing the global issues involved with agriculture and other human uses of plant diversity. Content is searchable at https://npgsweb.ars-grin.gov/gringlobal/taxon/taxonomysearcheco.aspx