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Chemical Polymorphism of Essential Oils of Artemisia vulgaris

Growing Wild in Lithuania
Asta Judzentiene,* and Jurga Budiene
State Research Institute, Center for Physical Sciences and Technology, Sauletekio Ave. 3, LT–10222, Vilnius, Lithuania,
e-mail: asta.judzentiene@ftmc.lt

Compositional variability of mugwort (Artemisia vulgaris L.) essential oils has been investigated in the study. Plant
material (over ground parts at full flowering stage) was collected from forty-four wild populations in Lithuania. The
oils from aerial parts were obtained by hydrodistillation and analyzed by GC(FID) and GC/MS. In total, up to 111
components were determined in the oils. As the major constituents were found: sabinene, 1,8-cineole, artemisia
ketone, both thujone isomers, camphor, cis-chrysanthenyl acetate, davanone and davanone B. The compositional
data were subjected to statistical analysis. The application of PCA (Principal Component Analysis) and AHC
(Agglomerative Hierarchical Clustering) allowed grouping the oils into six clusters. AHC permitted to distinguish an
artemisia ketone chemotype, which, to the best of our knowledge, is very scarce. Additionally, two rare cis-
chrysanthenyl acetate and sabinene oil types were determined for the plants growing in Lithuania. Besides,
davanone was found for the first time as a principal component in mugwort oils. The performed study revealed
significant chemical polymorphism of essential oils in mugwort plants native to Lithuania; it has expanded our
chemotaxonomic knowledge both of A. vulgaris species and Artemisia genus.

Keywords: Artemisia vulgaris, chemical variability, essential oils, Lithuania, statistical data analysis.

Fresh plants have a strong odor and a spicy-bit-

Introduction
Artemisia L. (Asteraceae family, Anthemideae tribe) is a
genus containing numerous species of small herbs
and shrubs largely found in Northern temperate
regions.
Artemisia vulgaris L. (often called as mugwort) is
a perennial herb common in Europe, Siberia, Central
Asia, N. Africa; it has been naturalized in N. Amer-
ica.[1] Mugwort has been identified as an aggressive
weed, mostly because of its ability to propagate
easily from small rhizome fragments.[2] The plant
can reach even up to 2.0 m in height; strong and
erect red-purplish stems are grooved, branched or
simple. The dark green leaves are deeply cut with
silvery-downy beneath, small aromatic flower heads
are symmetrical with many yellow or dark red
petals; its blooming season is from July to Septem-
ber with sporadic seedling. The plant grows in the
open fields and waste grounds, along roadsides, on
the skirts of the wood and river banks, very often
forming dense colonies.[2] A. vulgaris exhibits wide
morphological and genetic variability. Several vari-
eties of A. vulgaris growing in Lithuania have been
described.[1]
ter taste. Mugwort has been used as an herbal rem-
edy and for flavoring purposes, as a spice (mainly
for fatty meat dishes), for preparation of some bev-
erages, its young shoots are edible. A. vulgaris syn-
thesizes many bioactive compounds, such as
terpenoids, sesquiterpene lactones, flavonoid glyco-
sides, coumarins, carotenoids, resins, alkaloids, and
polysaccharides. Essential oil (EO) makes a significant
contribution to plant biological activity as well, and
for that reason the chemical composition was a sub-
ject of many studies[2 – 39] (and references cited
therein). The most important and characteristic com-
ponents of mugwort oils are a-, b-pinene, myrcene,
phellandrene, cis-, trans-thujone, camphor, 1,8-
cineole, artemisia ketone, borneol, verbenone,
caryophyllene and its oxide, isobornyl isobutyrate,
artemisia alcohol, chrysanthenol, cis-, trans-chry-
santhenyl acetate, lyratol, a-humulene, davanone B,
and elemol (Table 1).
The composition varied not only by individual prin-
cipal components, but also by the quantity of differ-
ent compound classes. EOs are used for their
allelopathic,[2][27][36] antimalarial,[7][36] anthelmintic,[10]
antifungal,[35][36] antimicrobial,[10][18][20][27][29][36]

DOI: 10.1002/cbdv.201700257 Chem. Biodiversity 2018, 15, e1700257 © 2018 Wiley-VHCA AG, Zurich, Switzerland
 Table 1. Previously reported main composition of essential oil of mugwort (Artemisia vulgaris L.) plants grown in different countries worldwidea
Main constituents ([%]) Plant material Origin of mugwort plants

trans-Chrysanthenyl acetate (≤24.6), b-thujone (≤20.8), 2,2,4- Aerial parts, at various stages of development Croatia (Dalmatia)[13]
trimethylcyclohexenecarboxaldehyde (≤16.6), 1,8-cineole (≤15.2),
a-pinene (≤15.1), a-phellandrene (≤12.9), camphor (≤8.7),

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a-thujone (≤8.5), c-cadinene (≤7.0), b-caryophyllene (≤6.4)
Borneol (≤27.0), 1,8-cineole (≤15.1), artemisia ketone (≤14.9), Aerial parts, different stages of development France (Provence)[13]
camphor (≤12.9), b-thujone (≤9.0), b-caryophyllene oxide (≤8.7), (vegetative, flower-buds, flowering, seeding)
b-caryophyllene (≤8.2), methyl eugenol (≤6.8), c-cadinene (≤6.8),
thujol (≤6.2), cis-chrysanthenol (≤5.6)
a-Thujone (35.5), camphor (26.0), 1,8-cineole (8.2) Leaves and twigs France[7]
Sabinene (15.9), myrcene (13.7), 1,8-cineole (9.8) Germany (Erlangen Botanical garden)[3]
Camphor (47.7), a-fenchene (9.1), verbenone (8.6), trans-verbenol Flowers and leaves in equal proportions, at full Italy (North-West Italian Alps, Piedmont)[6]
(7.0) blooming
cis-Chrysanthenyl acetate (≤23.6), b-thujone (≤20.2), 1,8-cineole Aerial parts, at earlier flowering stage Lithuania (Northern, seven different locations)[17]
(≤17.6), germacrene D (≤15.1), b-pinene (≤12.9), a-thujone
(≤12.9), caryophyllene (≤12.2), sabinene (≤8.4), artemisia ketone
(≤7.8)
Davanone B (≤44.4), germacrene D (≤30.5), camphor (18.9), 1,8- Aerial parts, at flowering stage Lithuania (fifteen different collecting sites)[37]
cineole (16.4), trans-thujone (≤10.9), cis-chrysanthenyl acetate

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(10.4)
1,8-Cineole (18.0), cis-chrysanthenyl acetate (15.0), terpinen-4-ol Aerial parts, during blooming Romania (Timisoara, Bencecul de Sus)[35]
(13.5), borneol (13.2), spathulenol (7.1), a-terpineol (6.6),
camphor (5.6)
1,8-Cineole (≤28.9), sabinene (13.7), b-thujone (13.5), neryl Entire herb, aerial part and root oils Serbia (Ni
s, Ni
sava riverside)[18]
2-methylbutanoate (13.2), b-eudesmol (10.0), bornyl 3-
Chem. Biodiversity 2018, 15, e1700257

methylbutanoate (8.4), caryophyllene oxide (6.5), a-bisabolol

(6.0), a-pinene (≤5.9), valeranone (5.5)
a-Pinene (53.7), trans-chrysanthenol (13.1), b-pinene (7.4),
b-myrcene (8.8)
1,8-Cineole (46.5), borneol (10.2), piperitol (9.5), a-cadinene (8.9),
camphor (6.2), a-humulene (5.5), 1,4-cineole (4.3)
a-Thujone (56.3), b-thujone (7.5), camphor (3.0)
b-Thujone (≤34.1), camphor (≤17.6), 1,8-cineole (≤12.1),
chrysanthenone (≤9.5), a-thujone (≤8.9), terpinen-4-ol (≤8.0)
Camphor (16.8), a-thujone (11.3), germacrene D (7.2), camphene
(6.5), 1,8-cineole (5.8), b-caryophyllene (5.4)
Camphor (≤38.7), isoborneol (≤20.9), artemisia alcohol (≤17.7),
a-thujone (≤16.0), b-eudesmol (13.9), 1,8-cineole (≤12.2),
b-caryophyllene (≤10.6), a-pinene (8.0), sabinene (≤6.1)
Artemisia ketone (≤29.4), a-thujone (≤21.7), p-cymene (7.6), trans-
caryophyllene (≤6.9), yomogi alcohol (5.5), 1,8-cineole (≤5.1)
Aerial parts, during flowering
Fresh material, leaves and stems
Leaves
Aerial parts, seasonal variation
Greenhouse grown plants, fresh leaves
Harvested at different growth periods (early
and late vegetative, budding, flowering (leaf
and flower oils), fruit initiation and
maturation)
Aerial parts
Russia, The Republic of Bashkortostan (Southern
Ural)[11]
China (Central, experimental farm in Wuhan)[19]
India (South, Nilgiri hills, Kodaikanal)[4]
India (Northern, Uttarakhand: Srinagar, Augustmuni,
Joshimath)[21]
Seeds of Indian origin, plantlets mass propagated
through in vitro liquid culture technology[22]
India (cultivated under subtropical conditions,
Lucknow experimental farm)[14]
India (different locations of Uttarakhand Himalaya:
Jhanjhar, Kaditalla, Chakrata)[39]

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 Table 1. (cont.)

Main constituents ([%]) Plant material Origin of mugwort plants

Elemol (8.9), 1,8-cineole + limonene (7.5), a-eudesmol (6.6) Aerial parts, at full flowering stage Iran (Northern, Gilan Province)[15]
Isobornyl isobutyrate (38.1), b-pinene (30.1), limonene (6.2) Aerial parts Iran (Imam zadeh Hashem, from Manjil to Rasht
road)[26]

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trans-Caryophyllene (24.8), 1,8-cineole (18.6), trans-salvene (14.9), Aerial parts Iran (Central, around the Kashan area)[24]
b-cubebene (11.8), a-humulene (5.5)
a-Pinene (23.6), menthol (9.7), b-eudesmol (8.3) Aerial parts Iran (West Azerbaijan, Nazlo, in the west of
Urmia)[32][34]
a-Thujone (30.5), 1,8-cineole (12.4), camphor (10.3), b-thujone Fresh leaves Nepal (Hetauda Makwanpur, 1550 m above sea level)[27]
(7.1)
Camphor (8.7), trans-pinocarvyl acetate (7.7), davanone (7.0), Aerial parts Syria[28]
trans-anethole (6.5), d-3-carene (5.7)
a-Thujone (56.1), b-thujone (12.0), caryophyllene oxide (10.2), Aerial parts, during flowering Turkey (Western and Southwestern Anatolia)[29]
1,8-cineole (8.5)
1,8-Cineole (≤24.3), camphor (≤14.7), b-pinene (≤11.7), a-terpineol Fresh plant material, Aerial parts during Vietnam (cultivated near Hanoi)[16]
(≤9.8), a-pinene (≤9.7), borneol (5.6) different vegetative cycle stages: before
flowering, beginning of the flowering (in
bud), flowering stage, end of flowering
Caryophyllene (24.1), b-cubebene (12.0), b-elemene (6.0) var. indica Maxim, leaves Vietnam[5]

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cis-Chrysanthenyl acetate (39.6), p-cymene (17.2), b-phellandrene Aerial parts Canada (Montreal)[33]
(11.4), trans-2-hexenal (5.0)
Caryophyllene oxide (31.1), hexadecanoic acid (6.3), isobornyl Aerial parts, at the beginning of the blooming Cuba (La Habana, Experimental Station in Guira de
2-methylbutyrate (5.3), 2-heptadecanone (5.1) stage Melena)[9]
1,8-Cineole (≤32.2), germacrene D (≤25.3), caryophyllene (≤19.6), Aerial parts, leaf and bud oils the USA (Pennsylvania, Erie)[30]
a-zingiberene (≤14.9), camphor (≤16.3), borneol (≤10.8),
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terpinen-4-ol (≤6.2), ar-curcumene (≤6.0)

a-Thujone (≤24.3), b-caryophyllene (≤17.5), santolina triene (10.0), Aerial parts the USA (various locations in North Eastern
Z,b-farnesene (≤8.1), p-cymene (≤7.0), germacrene D (≤6.7), Pennsylvania: Woodbridge, New Jersey, Wilmington,
b-thujone (≤6.1), b-mycene (≤5.9), a-pinene (≤5.7) Delaware)[33]
a-,b-Pinene, 1,8-cineole, camphor, camphene, santolina triene Aerial parts the USA (Ithaca, NY)[2]
Camphor (≤38.2), camphene (21.4), unidentified compounds Leaves and flowering stems, at flower bud Egypt (Giza)[25]
(≤21.6), verbenone (≤15.2), trans-verbenol (≤9.1), estragol (≤7.8) and opened flowers stages
Thujone (36.9) Fresh aerial parts, cultivated Egypt[10]
a-Phellandrene (17.3), lyratol (15.1), trans-isoelemicin (15.1), Leaves and stems Egypt[8]
c-elemene (8.8), humulene (8.8)
Camphor (13.8), 3,5-dimethylcyclohexene (13.8), germacrene D Fresh aerial parts, cultivated Experimental farm (Cairo University, Giza) Egypt;
(10.4), a-cubebene (10.4) seeds from Russia (St. Petersburg)[38]
a-Thujone (65.5), camphor (13.6), b-thujone (9.0) Commercial mugwort oil Moroccan origin[35]
a
Available data of mugwort EOs from European, Asian, American and African countries listed in an alphabetic order.

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 Chem. Biodiversity 2018, 15, e1700257
insecticidal,[19][31][34][36] antioxidant,[20][29][36] antibacte-
rial[23] and other properties.[27][36][37]
Previous limited studies of the volatile components
from mugwort grown in Lithuania were rather frag-
mentary,[17][37] and unfortunately no comprehensive
study on the native populations of A. vulgaris is avail-
able. This is the first detailed report on the analysis of
the EO compositions of mugwort (160 individual
plants collected at full flowering) from forty-four dif-
ferent accessions distributed all over the territory of
Lithuania (Figure 1).
Results and Discussion
The composition of EOs from mugwort plants can be
related to the genetic, phenological characteristics
and environmental factors, such as soil type, tempera-
ture, humidity, intensity of solar radiation and day
length, interspecies interactions in ecosystems, impact
of damaging factors, etc. Full compositions of twelve
characteristic mugwort EOs are presented in Table 2.
In total, up to 111 components were identified and
Figure 1. Geographical distribution of the forty-four Artemisia vulgaris L. sampling sites in Lithuania (detail description of them is
presented in Table 3).
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they comprised 78.8 – 99.3% of the total oils content.
The quantity of monoterpene hydrocarbons varied
from 0.4 to 58.6%, the amount of oxygenated
monoterpenes was 10.2 – 66.4%, the percentage of
sesquiterpene hydrocarbons differed from 5.2 to
36.6% and the quantity of oxygenated sesquiterpenes
was 6.5 – 36.8%. Only 20 compounds were found in
appreciable amounts (≥ 5.0%, at least in one sample).
The principal constituents (sabinene, 1,8-cineole,
trans-thujone, artemisia ketone, cis-chrysanthenyl acet-
ate, camphor and davanone) determined in A. vulgaris
EOs in this study are presented in Figure 2.
The data of the principal chemical composition of
44 oils were subjected to statistical analysis [Principal
Component Analysis (PCA) and Agglomerative Hierar-
chical Clustering (AHC)].
PCA was done by Pearson and Spearman methods,
the last one type was chosen and data were pre-
sented in Figure 3.
PCA has shown that the highest positive correla-
tion coefficients in the correlation matrix (Spearman,
significance level a = 0.05) were between cis- and
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 Table 2. Detailed chemical composition of twelve typical mugwort (A. vulgaris) essential oils
Compounda RInLitb RInexpc RIpexpd 31 30 23 4 9 11 18 21 28 39 42 41e

OctaneRef 800 800 5.0 0.6 0.7

(2E)-Hexanal 855 855 1215 0.6
Santolina triene 908 909 1030 0.8

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Artemisia triene 929 929 1047 0.6
a-Thujene 930 930 1025 0.2 tr. 0.1 tr. 0.3
a-PineneRef 939 945 1035 0.5 0.3 0.5 5.1 2.3 0.1 1.4 4.3 0.3 0.9 4.1 0.1
Camphene 954 950 1069 2.1 tr. 0.8 0.3 2.0
SabineneRef 975 975 1129 1.1 1.9 40.0 7.9 10.9 6.0 11.8 0.8 9.9 3.5 0.1
b-PineneRef 979 980 1114 0.3 0.5 15.2 0.3 1.4 0.2 5.2 0.2
MyrceneRef 990 990 1160 0.2 1.0 1.9 1.3 0.2 1.0
Yomogi alcohol 999 999 1405 3.9
a-Phellandrene 1002 1005 1205 0.5
a-TerpineneRef 1017 1017 1180 0.4 0.6 tr. 0.2 tr. 0.6
p-CymeneRef 1024 1028 1272 0.1 tr. 2.8 0.2 1.3 1.7
1,8-CineoleRef 1031 1032 1218 2.5 12.5 0.9 32.7 14.5 24.9 12.3 6.9 0.5 12.1 8.4 3.3
cis-b-Ocimene 1037 1039 1238 0.4 0.3 0.9 0.6
Benzene acetaldehyde 1042 1042 1648 tr. 0.7 0.5
trans-b-Ocimene 1050 1050 1250 1.7 0.5 1.2 0.2 1.9 1.2

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c-Terpinene 1059 1060 1255 1.7 0.9 0.8 1.0 1.9 0.4 1.9
Artemisia ketone 1062 1062 1357 41.0 0.2
cis-Sabinene hydrate 1070 1072 1468 1.6 0.8 tr. 0.5 tr.
Artemisia alcohol 1083 1084 1510 1.3
Terpinolene 1088 1086 1268 tr. 0.4 tr.
LinaloolRef 1096 1096 1550 0.9 tr.
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trans-Sabinene hydrate 1098 1098 1559 1.8

Nonanal 1100 1099 1395 tr. 0.5 tr.
cis-ThujoneRef 1102 1104 1428 0.1 0.1 3.6 19.6 3.2
2,6-Dimethylphenol 1108 1107 1.1
trans-ThujoneRef 1114 1117 1445 0.3 5.5 8.0 14.6 5.6
Chrysanthenone 1123 1128 1498 0.4 0.8 0.6
3-iso-Thujenol 1139 1138 1573 0.8 1.8 3.2
trans-Sabinol 1142 1144 1721 0.2 1.1
CamphorRef 1146 1146 1520 0.6 2.1 8.4 8.0 1.6 2.2 1.5 3.7 21.7 3.1
Sabina ketone 1159 1160 1685 0.2
Isoborneol 1160 1162 1660 0.5 0.1 0.6
Pinocarvone 1164 1164 1585 tr. tr. 0.3
cis-Chrysanthenol 1164 1166 1682 1.3 3.6 0.2
Borneol 1169 1169 1695 5.0 1.1 4.3 7.1 2.8 1.4 1.9 1.3
Terpinen-4-ol 1177 1178 1604 tr. tr. 5.7 3.4 1.0 1.4 1.4 0.3 4.5 0.7
a-Terpineol 1188 1188 1698 tr. 0.8 0.6 2.7 1.4 1.5 0.9 0.2 1.4 1.1
Myrtenol 1195 1196 1786 0.3

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 Table 2. (cont.)

Compounda RInLitb RInexpc RIpexpd 31 30 23 4 9 11 18 21 28 39 42 41e

Myrtenal 1195 1198 1645 0.3

VerbenoneRef 1205 1206 1710 0.3
Dihydro-iso-Carveol 1214 1215 0.3

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trans-CarveoRef 1216 1217 1839 1.0
Z-Ocimenone 1229 1230 0.3
Cumin aldehyde 1241 1239 0.2
Carvotanacetone 1247 1247 0.5
cis-Chrysanthenyl acetate 1265 1266 1560 55.7 0.2 0.2
Perilla aldehydeRef 1271 1272 1795 0.5 0.2
Bornyl acetate 1288 1289 1576 0.2 1.2 tr. 0.2
trans-Sabinyl acetate 1290 1291 1640 0.2 tr.
d-Elemene 1339 1338 0.7 0.9 1.0 0.8
7-epi-Silphiperfol-5-ene 1348 1348 1462 0.2
a-Terpinyl acetate 1349 1354 tr. tr. 0.1 tr.
a-Ylangene 1375 1375 1492 0.3
a-Copaene 1376 1376 1498 0.5 tr. 1.6 0.4 0.5 0.9 1.4 0.4 1.0
b-Patchoulene 1381 1384 1488 0.3
b-Bourbonene 1388 1388 1524 tr. 0.4 tr. tr. 0.7 2.6 0.4 1.1

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b-Elemene 1390 1391 1585 1.3 0.4 2.2 1.0 1.9 1.6 0.8 3.2 4.8 0.1 1.0 4.1
b-CaryophylleneRef 1419 1414 1608 1.0 1.8 0.6 1.3 3.3 1.3 0.7 2.7 3.0 0.5 5.2 4.2
b-Ylangene 1420 1420 1570 0.7 0.5 0.6 3.0 2.9 3.0
b-Copaene 1432 1432 1555 tr. 0.4 tr. 1.0 1.4 1.1 1.1
(Z)-b-Farnesene 1442 1442 1645 0.1 0.4 0.9
Aromadendrene 1441 1444 1615 0.5
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a-HumuleneRef 1454 1456 1680 0.5 0.5 tr. 0.6 0.4 0.7 2.0 2.4 1.3 2.2 4.0 3.0
allo-Aromadendrene 1460 1461 1659 1.0 0.1
cis-Cadina-1(6),4-diene 1463 1463 0.2 tr.
a-Acoradiene 1466 1466 1670 0.6
c-Himachalene 1476 1705 0.9
c-Gurjunene 1477 1478 1678 0.9 0.7
c-Muurolene 1479 1480 1690 0.1 0.2 0.3 0.5
Germacrene DRef 1485 1485 1719 5.1 1.6 5.4 2.2 7.0 2.2 9.1 11.3 11.5 3.7 10.6 7.5
(E)-b-Ionone 1488 1488 1955 0.1 0.4 tr.
b-Selinene 1490 1490 1735 0.6 tr. 0.9 0.8 3.9 0.2 2.7
Neryl isobutyrate 1491 1494 1842 0.4
Bicyclogermacrene 1500 1500 1763 0.2 0.4 1.3 0.4 1.3 1.6 1.0 2.3
trans-b-Guaiene 1503 1502 1537 0.2
(E,E)-a-Farnesene 1505 1505 1761 0.6
a-Cuprenene 1505 1507 0.6
c-Cadinene 1513 1515 1765 0.4 0.7 1.0 0.6 0.3
d-Cadinene 1523 1525 1760 1.6 tr. 0.3 0.7 1.9 1.5 1.6 2.4 0.6 0.8 1.6 2.4

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 Table 2. (cont.)

Compounda RInLitb RInexpc RIpexpd 31 30 23 4 9 11 18 21 28 39 42 41e

a-Cadinene 1538 1538 1775 0.1

a-Calacorene 1545 1546 tr. 0.2 0.2
(E)-Nerolidol 1563 1564 2050 1.6 0.5 0.3 1.1 0.3 0.6 0.8 0.2

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Davanone B 1566 1565 1966 7.0 3.0 1.3 0.6 16.1 1.0
b-Calacorene 1565 1566 1942 tr. 0.1 0.5
Germacrene-D-4-ol 1575 1570 2059 1.3
Spathulenol 1578 1578 2139 2.8 2.0 2.9 1.8 4.0 3.6 3.0 3.0 5.3 3.6 3.7
Sesquisabinene hydrate 1579 1579 0.6
Caryophyllene oxideRef 1583 1585 1999 7.2 2.1 3.7 2.9 4.1 5.4 2.2 5.1 3.6 2.2 7.2 3.2
Davanone 1587 1588 2032 11.4 27.9
Salvial-4(14)-en-1-one 1594 1595 0.1 1.0 tr. 0.4 1.5 0.8 0.5 0.5 0.3 0.5
Humulene epoxide II 1608 1620 2053 2.3 0.5 1.1 0.5 1.0 1.1 1.9 0.5 3.2 1.2
Caryophylla-4(14),8(15)-dien-5a-ol 1640 1640 0.7 0.5 0.5 1.5
3-iso-Thujopsanone 1642 1642 0.6 1.0
a-epi-Muurolol 1642 1643 2180 tr. 1.0 1.5 0.5 3.2 2.0 0.6
Vulgarone B 1651 1652 2160 5.0
a-Cadinol 1654 1654 2230 tr. 0.9 2.0
Khusinol 1680 1680 1.3

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Eudesma-4(15),7-dien-1b-ol 1688 1688 0.7 0.9 1.5 1.8 1.0
Germacra-4(15),5,10(14)-trien-1a-ol 1686 1689 1.4 3.0 4.0
Total 99.3 92.1 93.6 90.4 82.9 78.8 84.4 83.9 91.9 81.9 93.0 79.8
Monoterpene hydrocarbons 1.9 2.7 58.6 19.1 14.1 3.1 11.8 20.6 2.9 18.4 16.5 0.4
Oxygenated monoterpenes 59.2 66.4 12.3 56.3 23.7 42.8 35.7 12.3 40.5 43.3 10.2 19.7
Sesquiterpene hydrocarbons 12.5 5.2 10.9 7.6 16.5 12.1 24.1 36.1 28.7 7.7 36.6 21.7
Chem. Biodiversity 2018, 15, e1700257

Oxygenated sesquiterpenes 24.4 16.4 6.6 6.5 28.6 17.5 8.4 13.1 17.2 12.5 27.1 36.8
a
Constituents are listed in order of their elution from a non-polar DB-5 column; compounds are identified by their mass spectra and retention indices on both (polar DB-Wax
and nonpolar DB-5) columns. b RInLit: Kovat’s indices for a nonpolar column DB-5 taken from the literature.[40] cRInexp: Retention indices determined experimentally on the non-
polar column DB-5. d RIpexp: Retention indices determined experimentally on the polar column DB-Wax. e Numbers indicate mugwort essential oils and corresponding sam-
pling sites of the plants in Lithuania (the same indication is in Table 3 and Figures 1, 3, and 4). Ref Additional identification with reference compound; tr. – traces (<0.05%).
Compounds determined only in traces: a-campholenal, trans-pinocarveol, carvone, geraniol, geranial, cis-carvyl acetate, Z-nerolidol, trans-cadina-1,4-diene and trans-calame-
nen-10-ol. Principal constituents and their percentages are indicated in bold.

© 2018 Wiley-VHCA AG, Zurich, Switzerland

 Chem. Biodiversity 2018, 15, e1700257
Figure 2. The major compounds determined in essential oils of A. vulgaris L. plants growing in Lithuania.
Figure 3. Principal component analysis of the 44 essential oils
of Artemisia vulgaris L. from Lithuania.
trans-thujone isomers (0.826), germacrene D and
b-caryophyllene (0.595); and between davanone B and
cis-chrysanthenol (0.508). The lowest values of nega-
tive correlation were noted between 1,8-cineole and
thujones (
0.469 and
0.486, for cis and trans iso-
mers, respectively).
Data clustering (AHC) was performed by various
methods; and the Euclidean distance weighted pair-
group average method was chosen as the most
demonstrative one. According to this clustering tech-
nique, six clusters were distinguished (Figure 4,
I – VI).
Cluster I contained two individual oils indicated by
numbers 31 and 34 (Figure 4). These oils differed from
all the rest samples by exceptionally large amounts of
cis-chrysanthenyl acetate (55.7 and 62.0%). As the sec-
ond and third main constituents were caryophyllene
oxide 7.2% and davonone B 7.0% in the sample 31
(for full composition, see Table 2). In oil 34, the only
predominant compound was cis-chrysanthenyl acetate
(62.0%), whereas the quantities of none of the other
constituents exceeded 5% level. The mugwort
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essential oils of chrysanthenyl chemotype are quite
rare. cis-Chrysanthenyl acetate has been determined
among the principal components in the mugwort oils
from Canada (Montreal) (39.6%),[33] Northern Lithuania
(23.6%),[17] and Romania (Timisoara, Bencecul de Sus)
(15.0%),[35] while the trans isomer of this compound
was predominant in the oils from Croatia (Dalmatia)
(24.6%).[13]
Mugwort oil 30, containing 41.0% of artemisia
ketone and 12.5% of 1,8-cineole was attributed to
cluster II (Figure 4; Table 2). Artemisia ketone was
found to be the predominant constituent only in
this sample out of all forty-four investigated oils. To
the best of our knowledge, A. vulgaris oil of the
artemisia ketone chemotype is very scarce. The
mugwort oil of this type, containing 29.4% of arte-
misia ketone followed by p-cymene (7.6%) and
yomogi alcohol (5.5%) was described very recently
in plants grown in Uttarakhand Himalaya (India).[39]
Appreciable quantity (14.9%) of this ketone was
determined in the French mugwort oils obtained
from the plants collected at seeding stage, while
during flowering this compound was not
detected.[13]
Cluster III contained sample 23 (Figure 4), where an
appreciable amount of sabinene (40.0%) was deter-
mined. b-Pinene (15.2%) and terpinen-4-ol (5.7%) were
found as the second and third compounds (Table 2),
respectively. A. vulgaris EOs of sabinene type are not
common. Sabinene has been determined as the major
compound in an amount of only 15.9% [other main
components with close quantities were myrcene
(13.7%) and 1,8-cineole (9.8%)] in mugwort oils from
plants cultivated in Erlangen Botanical Garden,
Germany.[3]
Cluster IV, composed of twenty-two oils, is the lar-
gest one (Figure 4). Samples 1 – 19 were characterized
by 1,8-cineole as the first main component, whose
percentage varied from 9.9 to 32.7%. The following
compounds were detected as the second or third
main components: b-pinene, sabinene, trans-thujone,
camphor, borneol, cis-chrysanthenyl acetate, germa-
crene D, c-muurolene, caryophyllene and its oxide,
© 2018 Wiley-VHCA AG, Zurich, Switzerland
 Chem. Biodiversity 2018, 15, e1700257

Figure 4. Dendrogram by AHC of the 44 essential oils of Artemisia vulgaris L. from Lithuania clustered by Euclidean distance weighted
pair-group average method. AHC formed six clusters (I – VI), n-number of samples in every cluster.

spathulenol, and davanone. 1,8-Cineole has been
described as a common compound among principal
constituents in the mugwort oils from Croatia,[13]
France,[7][13] Romania,[35] Serbia,[18] the USA,[2][30]
India,[14][21] Iran,[24] and Nepal.[27] Oils 20, 21, and 24,
containing sabinene (11.8 – 16.4%) as the first princi-
pal compound; 1,8-cineole (6.9 – 7.5%) and germa-
crene D (6.8 – 14.4%) as other two main constituents,
were attributed to the same subcluster in cluster IV.
Detailed compositions of oils 4, 9, 11, 18, and 21 are
presented in Table 2.
Seven essential oils, namely, 22, 25 – 29, and 32
formed cluster V (Figure 4). Oil 22 contained: sabi-
nene (12.0%), cis-chrysanthenyl acetate (10.4%), and
germacrene D (9.5%) as main constituents. Oils
25 – 29 distinguished from the rest in this cluster
by appreciable amounts of thujone, the quantity of
both isomers varied from 11.2 to 34.2%. Oil 28 was
characterized by cis- and trans-thujone, 19.6 and
14.6%, respectively (for full composition see
Table 2). Sample 26 contained 20.2% of trans-
thujone and a significant amount of artemisia
ketone (7.8%), as the second principal compound.
The main composition of oil 32 was as follows: cis-
chrysanthenyl acetate (10.4%), germacrene D (9.5%),
and trans-thujone (9.4%). Thujone has been deter-
mined among main constituents in numerous mug-
wort oils form the plants growing in Croatia,[13]
France,[7][13] Lithuania,[17][37] Serbia,[18] the USA,[33]
India,[4][14][21] Nepal,[27] Turkey,[29] Egypt,[10] and
Morocco.[35]
As for cluster VI, it comprises eleven essential oils
33, 35 – 44. Camphor (12.0 – 30.0%) was determined
as a major constituent in the oils 35 – 40 (detailed
composition of the oil 39 is presented in Table 2).
Camphor is one of the most frequently found main
components in EOs of A. vulgaris native to various
word countries.[2][6][7][13][14][21][22][25][27][28][30][38] Oils
41 – 44 attributed to the same subcluster were
characterized by major compound one of the dava-
nones isomers, davanone (7.0 – 27.9%, numbers 41,
43, and 44) or davanone B (16.1%, Table 2, sample
42). In the previous research on A. vulgaris volatile
secondary metabolites, performed in our labora-
tory,[37] mugwort EOs predominantly contained dava-
none B ranging from 13.3 to 44.4%. This study
confirmed the davanone B chemotype once again.
Besides, the presence of mugwort oils of davanone
type (Table 2, sample 41) has been revealed for the
first time.

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 Chem. Biodiversity 2018, 15, e1700257

Table 3. Collecting sites of Artemisia vulgaris L. in Lithuania

Site codea Name of natural growing localityb Latitude (N) Longitude (E) Soil typec Number of plantsd

1 Rokiskis d., Aleknos v. 56° 60 55.34″ 25° 390 53.43″ Cl 5

2 Kedainiai d., Labunava 55° 110 46.44″ 23° 540 9.56″ Ml 3
3 Vilnius d., Nemezis 54° 370 11.84″ 25° 200 58.1″ SLm 4
4 Trakai d., Streva 54° 350 19.42″ 24° 420 22.71″ SLm 3
5 Neringa c., Curonian Splite 55° 280 27.2″ 21° 40 52.34″ SLm 5
6 Moletai c. 55° 130 26.5″ 25° 250 5″ Gr 4
7 Rokiskis d., Aleknos v. 56° 60 57.53″ 25° 390 33.61″ Ml 4
8 Vinius c., Rastinenai 54° 450 15.94″ 25° 20 49.62″ Sl 4
9 Vilnius c., Sapiegine 54° 420 38.74″ 25° 190 41.68″ Cl 3
10 Vilnius d., Raudondvaris 54° 520 38.18″ 25° 330 34.56″ Lm 3
11 Klaipeda d., Plikiai v. 55° 470 30.82″ 21° 160 57.74″ Ml 3
12 Svencionys d., Zeimenys l. 55° 160 34.46″ 26° 30 36.09″ Gr 4
13 Siauliai d., Kairiai 55° 550 47.44″ 23° 250 35.3″ Ml 5
14 Kretinga d., Kartena 55° 560 6.25″ 21° 280 56.34″ Lm 4
15 Ignalina c., Meksrinis l. 55° 210 1.9″ 26° 100 17.9″ Gr 5
16 Mazeikiai d., Tirksliai 56° 150 40.59″ 22° 180 53.33″ Ml 4
17 Panevezys d., Medeliai 55° 410 11.32″ 24° 250 57.13″ Lm 3
18 Alytus d., Raitininkai v. 54° 140 7.9″ 24° 70 14.25″ Cl 4
19 Jonava c. 55° 40 58.23″ 24° 160 32.57″ SLm 3
20 Svencionys d., Zeimenys l. 55° 160 21.68″ 26° 20 15.42″ Gr 3
21 Kretinga d., Kretingale 55° 500 16.88″ 21° 110 4″ Ml 4
22 Panevezys d., Staniunai v. 55° 430 1.39″ 24° 240 18.7″ Sl 4
23 Klaipeda c. 55° 430 11.21″ 21° 70 48.64″ SLm 3
24 Neringa c., Pervalka 55° 240 59.87″ 21° 50 45.1″ SLm 4
25 Rokiskis d., Salos v. 55° 480 40.59″ 25° 210 58.22″ Ml 4
26 Birzai d., Kvietkeliai v. 56° 130 15.70″ 24° 430 25.05″ Ml 3
27 Kelme c. 55°370 40″ 22°550 15.2″ Lm 4
28 Klaipeda c., Dane r. 55° 420 43.21″ 21° 80 19.88″ SLm 3
29 Alytus d., Raitininkai v. 54° 140 17.44″ 24° 70 17.89″ Cl 5
30 Sventoji c., Palanga d. 56° 10 54.8″ 21° 50 14.52″ SLm 3
31 Utena d., Griutys v. 55° 270 31″ 25° 380 23.04″ SLm 3
32 Panevezys d., Staniunai v. 55° 420 57.58″ 24° 240 16.83″ Ml 4
33 Naujoji Akmene d., Venta 56° 110 56.45″ 22° 410 15.77″ Cl 3
34 Kaunas d., Babtai 55° 50 15.39″ 23° 490 29.92″ Lm 3
35 Vievis d., Varliskes v. 54° 460 24.8″ 24° 510 52.12″ Gr 3
36 Ukmerge d., Sventupe 55° 190 31.7″ 24° 530 27.74″ SLm 3
37 Kaisiadoriai d., Zelva l. 54° 490 6.98″ 24° 470 57.9″ Ml 3
38 Rokiskis d., Aleknos v. 56° 70 1.25″ 25° 390 44.94″ Ml 3
39 Rokiskis d., Aleknos v. 56° 60 56.42″ 25° 390 45.5″ Ml 3
40 Klaipeda d., Slikiai v. 55° 500 49.83″ 21° 120 31″ Lm 3
41 Radviliskis d., Grinkiskis v. 55° 330 17.15″ 23° 370 45.44″ Gr 3
42 Skuodas d., Mosedis 56° 90 53.66″ 21° 340 24.21″ Sl 4
43 Trakai d., Rudiskes 54° 310 47.08″ 24° 500 12.4″ SLm 4
44 Trakai d., Aukstadvaris 54° 340 53.46″ 24° 310 45″ SLm 5
a
A. vulgaris sampling sites are shown in the map (Figure 1) and corresponding mugwort EOs are indicated in the dendrogram (Fig-
ure 4). b Abbreviations: d.-district, c.-city, v.-village, l.-lake shore, r.-riverside. c Soil type: Cl-clay; Lm-Loam, SLm-sandy loam, Gr-gravel,
Ml-mould, Sl-silt loam. dOne representative plant from every collecting location has been deposited to the Herbarium (BILAS).

A. vulgaris in Lithuania. A significant genetic variability

Conclusions
Artemisia vulgaris L. is characterized by a wide
intraspecific variability caused both by high genetic
diversity and good environmental adaptability. The
data obtained indicated the presence of remarkable
chemical polymorphism within the populations of
impacts on the variation of EO components observed.
Besides, environmental factors possibly may affect this
variation. The investigated essential oils were attribu-
ted to six different types. 1,8-Cineole, both thujone
isomers and camphor, whose are common in mug-
wort oils, were determined among major components.

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 Chem. Biodiversity 2018, 15, e1700257
Moreover, some uncommon or very rare oil types
were revealed. Among all the forty-four essential oils
studied, the unique sample of artemisia ketone
chemotype drastically diverged from the rest oils.
Besides, two rare oil chemotypes of cis-chrysanthenyl
acetate and sabinene were determined for mugwort
plants growing in Lithuania. Four oil samples were
characterized by one of the davanones isomers. The
present investigation once again confirmed the pres-
ence of davanone B chemotype, which has previously
been determined in our laboratory[37]; and revealed
the existence of mugwort oils of another davanone
isomer type.
The report of the new chemical profiles of volatile
oils has expanded our chemotaxonomic knowledge
both of A. vulgaris species and Artemisia genus.
Experimental Section
Surveyed Populations, Plant Material
The aerial parts of Artemisia vulgaris plants (160
individuals) were collected at full flowering stage
(July – August, during several years) from 44 sites of
natural populations in Lithuania. Raw material
(mainly leaves and flowering tops) was taken imme-
diately to the laboratory to be dried at room tem-
perature (20 – 25 °C) under shade conditions. Plant
material has been identified and voucher specimens
of representative individuals from the most acces-
sions were deposited in the Herbarium (BILAS) of
the Institute of Botany of the Nature Research Cen-
tre (Vilnius, Lithuania). Identity of herbal material
has been verified by Dr. V. Rasomavicius. Code num-
bers of the growing localities were as follows:
65257, 65259, 65262, 65263, 65265 – 65269, 68935,
68936, 68938 – 68941, 68942, 68944, 68948 – 68953,
68955, 68958, 68964, 68968, 68970 – 68975. The
spatial distribution of investigated populations was
depicted on the geographic information system map
(Figure 1). A detailed description of the collecting
sites of A. vulgaris in Lithuania is presented in
Table 3.
Essential Oil Isolation
The essential oils were prepared by hydro-distillation
for 2 h and 30 min of air-dried material in a Cle-
venger-type apparatus according to the European
Pharmacopoeia. The yields of yellow oils with a strong
characteristic odor ranged from 0.15 to 0.3% (v/w, on
a dry weight basis). The obtained oils were dried over
anhydrous sodium sulphate, kept in closed dark vials
and stored in a refrigerator, before analysis the
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samples were diluted with a mixture of pentane and
diethyl ether (1:1).
GC (Flame-Ionization Detector) Analysis
Quantitative analyses of the essential oils were carried
out by GC on a DB-Wax capillary column (polyethy-
lene glycol 30 m 9 0.25 mm i.d., film thickness
0.25 lm) using a Perkin-Elmer Clarus 500 chro-
matograph equipped with an FID. The oven tempera-
ture was programmed from 60 °C to 280 °C at a rate
of 3 °C/min. The injector and detector temperatures
were 250 °C; carrier gas helium (1 mL/min); split 1:60.
At least two repetitions (n ≥ 2) per analysis were per-
formed and the results are presented as an average
composition.
GC/MS Analysis
Analyses were performed using a chromatograph Shi-
madzu GC/MS-QP2010 equipped with a capillary column
DB-5 (5%-phenyl)-methylpolisiloxane (50 m 9 0.32
mm 9 0.25 lm). The GC oven temperature was pro-
grammed from 60 °C (isothermal for 2 min) to 160 °C
(isothermal for 1 min) at a rate of 5 °C/min, then
increased to 250 °C at a rate of 10 °C/min, and the final
temperature was kept for 3 min. The temperature of
the injector and detector was 250 °C. The flow rate of
carrier gas (helium) was 1 mL/min, split 1:40. Mass spec-
tra in electron impact mode were generated at 70 eV,
0.97 scans/second, mass range 35 – 650 m/z.
Identification of Compounds
Qualitative analysis was based on the comparison of
retention indexes on both columns, co-injection of
some terpene references and C8 – C28 n-alkane ser-
ies; and mass spectra with corresponding data in
the literature[40] and computer mass spectra libraries
(using ‘GC/MS solution’ v. 2.71 software from Shi-
madzu and Wiley). Identification has been approved
when computer matching with the mass spectral
libraries was with probability above 90%. The rela-
tive proportions of the oil constituents were
expressed as percentages obtained by peak area
normalization, all relative-response factors being
taken as one.
Statistical Data Analysis
Principal Component Analysis (PCA) and Agglomera-
tive Hierarchical Clustering (AHC) were performed
using XLSTAT (Addinsoft, 2014). Both methods were
© 2018 Wiley-VHCA AG, Zurich, Switzerland
 Chem. Biodiversity 2018, 15, e1700257
applied using a percentage of forty-four oils and
twenty variables (individual constituents with an
amount ≥5%, at least in one sample). PCA was per-
formed by Pearson and Spearman methods. AHC was
done using various methods and aggregation criteria,
and the final definition of the oil groups was based
on Euclidean distance, weighted pair-group average as
a criterion.
Author Contribution Statement
A. Judzentiene designed and executed the experiment,
interpreted results and wrote text of the manuscript.
J. Budiene performed experimental data analysis and
did technical works of the text.
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Received May 25, 2017
Accepted November 17, 2017
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