Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні
The component composition and the quantitative content of compounds distilled with water vapor in the thalli of Cetraria islandica (L.) Ach. harvested in Ukraine were determined using the method of gas chromatography with mass spectrometric detection (GC/MS). 24 compounds distilled with water vapor...
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| author | Shpychak, Alina O. Khvorost, Olga P. |
| author_facet | Shpychak, Alina O. Khvorost, Olga P. |
| author_institution_txt_mv | [
{
"author": "Alina O. Shpychak",
"institution": "National University of Pharmacy of the Ministry of Health of Ukraine",
"orcid": ""
},
{
"author": "Olga P. Khvorost",
"institution": "National University of Pharmacy of the Ministry of Health of Ukraine",
"orcid": ""
}
] |
| author_sort | Shpychak, Alina O. |
| baseUrl_str | https://ophcj.nuph.edu.ua/oai |
| collection | OJS |
| container_end_page | 57 |
| container_issue | 4 |
| container_start_page | 51 |
| container_title | Журнал органічної та фармацевтичної хімії |
| container_volume | 21 |
| datestamp_date | 2026-08-23T18:33:04Z |
| description | The component composition and the quantitative content of compounds distilled with water vapor in the thalli of Cetraria islandica (L.) Ach. harvested in Ukraine were determined using the method of gas chromatography with mass spectrometric detection (GC/MS). 24 compounds distilled with water vapor were identified with the prevalence of fatty acids and their derivatives (57.86±2.00% of the total compounds), terpenoids and their derivatives (23.57±0.97% of the total compounds) and acyclic saturated hydrocarbons (10.99±0.45% of the total compounds). The highest percentage was observed for octadecadienoic (linoleic) acid (20.08±0.67% of the total compounds), hexadecanoic (palmitic) acid (19.21±0.77% of the total compounds) and 9,17-octadecadienal (18.57±0.56% of the total compounds). The presence of 4 monoterpenoids and 6 sesquiterpenoids in the raw material studied was determined for the first time. |
| doi_str_mv | 10.24959/ophcj.23.299297 |
| first_indexed | 2025-07-23T04:43:26Z |
| format | Article |
| fulltext |
ISSN 2308-8303 (Print) / 2518-1548 (Online) 51
Original Research
http://ophcj.nuph.edu.ua
UDC 615.322:582.29
A. O. Shpychak, O. P. Khvorost
National University of Pharmacy of the Ministry of Health of Ukraine, 53 Pushkinska str., 61002 Kharkiv, Ukraine
The Study of Compounds Distilled with Water Vapor in Cetraria
islandica (L.) Ach. Thalli Harvested in Ukraine
Abstract
The component composition and the quantitative content of compounds distilled with water vapor in the thalli of Cetraria
islandica (L.) Ach. harvested in Ukraine were determined using the method of gas chromatography with mass spectrometric
detection (GC/MS). 24 compounds distilled with water vapor were identified with the prevalence of fatty acids and their de-
rivatives (57.86 ± 2.00 % of the total compounds), terpenoids and their derivatives (23.57 ± 0.97 % of the total compounds)
and acyclic saturated hydrocarbons (10.99 ± 0.45 % of the total compounds). The highest percentage was observed for octa-
decadienoic (linoleic) acid (20.08 ± 0.67 % of the total compounds), hexadecanoic (palmitic) acid (19.21 ± 0.77 % of the total
compounds) and 9,17-octadecadienal (18.57 ± 0.56 % of the total compounds). The presence of 4 monoterpenoids and 6
sesquiterpenoids in the raw material studied was determined for the first time.
Keywords: Cetraria islandica; thalli; compounds distilled with water vapor; GC/MS
А. О. Шпичак, О. П. Хворост
Національний фармацевтичний університет Міністерства охорони здоров’я України,
вул. Пушкінська, 53, м. Харків, 61002, Україна
Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach.
слані, заготовленої в Україні
Анотація
За допомогою методу газової хроматографії з мас-спектрометричним детектуванням (ГХ/МС) визначено компонент-
ний склад та кількісний вміст дистильованих з водяною парою сполук, що наявні у слані Cetraria islandica (L.) Ach.,
заготовленої в Україні. Ідентифіковано 24 сполуки, дистильовані з водяною парою, серед яких переважали жирні кис-
лоти та їхні похідні (57,86 ± 2,00 % від суми сполук), терпеноїди та їхні похідні (23,57 ± 0,97 % від суми сполук), ацикліч-
ні насичені вуглеводні (10,99 ± 0,45 % від суми сполук). Найвищий відсотковий вміст виявлено для октадекадієнової
(лінолевої) кислоти (20,08 ± 0,67 % від суми сполук), гексадеканової (пальмітинової) кислоти (19,21 ± 0,77 % від суми
сполук) та 9,17-октадекадієнового альдегіду (18,57 ± 0,56 % від суми сполук). Уперше для досліджуваної сировини
виявлено наявність 4 монотерпеноїдів та 6 сесквітерпеноїдів.
Ключові слова: Cetraria islandica; слань; сполуки, дистильовані з водяною парою; ГХ/МС
Citation: Shpychak, A. O.; Khvorost, O. P. The Study of Compounds Distilled with Water Vapor in Cetraria islandica (L.) Ach. Thalli
Harvested in Ukraine. Journal of Organic and Pharmaceutical Chemistry 2023, 21 (4), 51 – 57.
https://doi.org/10.24959/ophcj.23.299297
Received: 25 October 2023; Revised: 11 November 2023; Accepted: 15 November 2023
Copyright© 2023, A. O. Shpychak, O. P. Khvorost. This is an open access article under the CC BY license
(http://creativecommons.org/licenses/by/4.0).
Funding: The authors received no specific funding for this work.
Conflict of interests: The authors have no conflict of interests to declare.
■ Introduction
It is known from the literature that lichen raw
material has been an important component of tra-
ditional medicine, has long been used as a food
product for humans and livestock, a source of
spices, dyes and fragrances in the cosmetic and
perfume industry in many cultures, mainly in
Europe, South Asia and North America [1 – 3].
The widespread use of lichens for medical pur-
poses and in different industries is due to the pre-
sence of various groups of biologically active sub-
stances (BAS) in their composition, such as poly-
saccharides, lichen acids, amino acids, proteins,
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Журнал органічної та фармацевтичної хімії 2023, 21 (4)
fatty acids, vitamins, which have been the study
subject of many scientific works [1, 4 – 6].
The group of compounds distilled with water
vapor is not the main group of compounds that
cause the pharmacological effect of the lichen raw
material, but it is worth paying attention to it for
deepening the knowledge about the qualitative
composition and the quantitative content of the
BAS groups of the medicinal raw material. Some
representatives of this group of compounds, such
as aliphatic acids and aromatic compounds, are
synthesized in lichens in the same way as lichen
substances – specific secondary metabolites, some
of them are unique to lichens and rarely occur in
higher plants or fungi [1]. According to some data,
the number of secondary metabolites found in li-
chens exceeds 1000 and includes aliphatic and aro-
matic acids, depsides, depsidones, dibenzofurans
[3, 7]. Their presence causes antibacterial, antifun-
gal, antiviral, antiproliferative, antioxidant, and
other types of pharmacological activity [2, 3, 7, 8].
It has been demonstrated that essential oils
obtained from lichens of the genus Evernia (Par-
meliaceae) and Ramalina (Ramalinaceae), which
include, in particular, such substances as β-pinene,
α-pinene, camphene, limonene, myrcene, α-phelland-
rene, p-cymene, have antimicrobial and antifun-
gal effects [7, 9].
One of the most known representatives of the
Parmeliaceae family, Cetraria islandica (L.) Ach.
has been used in folk medicine in Central and
Northern Europe for centuries [10]. In pharma-
cognostic texts and handbooks of folk medicine,
there are examples of the use of this lichen as an
ingredient for the dishes of traditional cuisine
and food supplements in case of the gastrointesti-
nal tract disorders and for the treatment of res-
piratory diseases [2, 11].
Nowadays thalli of C. islandica are the phar-
macopoeial medicinal raw material in many coun-
tries; they are applied to manufacture drugs with
the proven efficiency used in the treatment of the
respiratory system inflammatory processes, cont-
ribute to the regulation of respiratory organs, have
antibacterial, anti-inflammatory, antitussive, sof-
tening and antioxidant effects [8, 12, 13].
Using gas chromatography with mass spectro-
metric detection it was possible to detect 23 com-
pounds in the raw material of C. islandica, 16 of
them were identified. Their composition included
fatty acids, aldehydes, phenols, and their ethers,
olefins, and lichen acids [14].
Since we have found only fragmentary data
on the component composition of compounds
distilled with water vapor in the thalli of C. islan-
dica in the literature available to us, the study
of this group of BAS as a part of a comprehen-
sive phytochemical study of the raw material of
C. islandica harvested in Ukraine is expedient,
relevant and has practical importance for the de-
velopment of modern effective medicinal products.
The aim of this work was to study the compo-
nent composition and determine the quantitati-
ve content of compounds distilled with water va-
por in the raw material of C. islandica harvested
in Ukraine to deepen knowledge about the qua-
litative composition and quantitative content of
BAS in the domestic raw material and for fur-
ther obtaining new substances and medicinal
products based on it.
■ Materials and methods
Plant raw material
For the study, thalli of C. islandica harvest-
ed in late summer/early autumn 2019 in the ter-
ritory of the Rakhiv district of the Zakarpattia
region were used. The raw material was dried
in the open air under a cover to an air-dry con-
dition and stored in paper bags in a dry place
protected from direct sunlight.
Equipment and conditions of chromato-
graphic separation
The determination of the component compo-
sition of compounds distilled with water vapor in
the raw material was carried out by the method
of gas chromatography with mass spectrometric
detection (GC/MS) [15, 16].
The chromatographic separation was perfor-
med on an Agilent 6890N gas chromatograph with
a 5973 inert mass detector (Agilent Technologies,
USA). A HP-5ms capillary column (length – 30 m,
inner diameter – 0.25 mm, diameter of the sorbent
grain – 0.25 μm) was used. The separation was
carried out in the gradient mode. The initial tem-
perature of 50 °C was maintained for 5 min, then
increased to 220 °C with the rate of 4 °C per mi-
nute, then with the rate of 10 °C to 300 °C was main-
tained for 10 min. The flow rate of the carrier gas
(helium) through the column was 1.0 mL min–1.
The temperature of the evaporator was 300 °C,
the sample was injected in a split mode with the
rate of 1:50, and the injection volume was 2 μL.
The detection was carried out in the SCAN mode
in the range of 38 – 400 m/z [17, 18].
Preparation of the raw material sample
The raw material previously crushed with a
laboratory mill LGM-1 (Olis, Ukraine) was ground
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Journal of Organic and Pharmaceutical Chemistry 2023, 21 (4)
to a powdery state in a glass mortar. After that,
300 mL of water was added to 5.00 g (accurate
weight) of the raw material and refluxed at a tem-
perature of 100 °C for 3 h. The distilled water was
extracted with heptane. The extract was evapo-
rated to 100 – 200 μL in a stream of nitrogen [19].
Identification and quantification
The identification of compounds distilled with
water vapor in the samples studied was perform-
ed using the NIST 02 mass spectrum library.
The match percentage of the compounds detect-
ed with the compounds from the NIST 02 mass
spectrum library was 80 – 99 % [20, 21].
The quantitative content (%) of the total com-
pounds was calculated by comparing the peak
area of the components with the sum of the ar-
eas of all peaks on the chromatogram [15, 17].
■ Results and discussion
The GC/MS chromatogram obtained for com-
pounds distilled with water vapor is shown in
Figure. The results of the determination of the
component composition and the quantitative con-
tent of compounds distilled with water vapor in the
raw material of C. islandica, as well as their chro-
matographic parameters, are given in Table.
As a result of the study, 24 compounds dis-
tilled with water vapor were identified in the thalli
of C. islandica harvested in Ukraine, including
terpenoids and their derivatives, acyclic satura-
ted hydrocarbons, dienes, fatty acids, esters.
Some of the compounds identified (2,2,4,4,6,6-
hexamethyl-1,3,5,2,4,6-trioxatrisilinane, diisobu-
tyl phthalate, 5-methyl-2-phenylindolizine) pro-
bably could have entered the samples studied from
the outside during harvesting or transportation.
A significant part of the substances identified
were terpenoids represented by 10 compounds and
made up 23.57 ± 0.97 % of the total quantitative
content of compounds distilled with water vapor.
Among them, 3 monocyclic monoterpenoids (cis-
menthone, trans-menthone, menthol), bicyclic mo-
noterpenoid trans-carane and 6 sesquiterpenoids
(caryophyllene, β-cubebene, γ-muurolene, δ-amor-
phene, sesquiterpene ketone mayurone, hexa-
hydrofarnesyl acetone) were found.
Among the compounds detected, the highest
quantitative content was observed for polyunsa-
turated ω-6 fatty octadecadienoic (linoleic) acid –
20.08 ± 0.67 % of the total compounds, saturated
n-hexadecanoic (palmitic) acid – 19.21 ± 0.77 %
of the total compounds and 9,17-octadecadienal
– 18.57 ± 0.56 % of the total compounds.
Figure. The GC/MS chromatogram of compounds distilled with water vapor in the thalli of C. islandica harvested in Ukraine
ISSN 2308-8303 (Print) / 2518-1548 (Online) 54
Журнал органічної та фармацевтичної хімії 2023, 21 (4)
Table. The component composition and the quantitative content of compounds distilled with water vapor in the thalli
of C. islandica (n = 5)
Retention time,
min The structure of the compound The name of the compound Content, %
1 2 3 4
13.83
O
Me
Me
Me
cis-menthone 1.59 ± 0.04
14.20
O
Me
Me
Me
trans-menthone 1.03 ± 0.05
14.51
HO
Me
Me
Me
menthol 11.95 ± 0.49
18.80
Me
Me
Me
H
H
trans-carane 1.27 ± 0.06
22.70
Me
Me
Me H
H
caryophyllene 1.73 ± 0.08
24.63
MeMe
Me
H
H
ϐ-cubebene 0.38 ± 0.02
25.65
Me Me
Me
H
H
γ-muurolene 1.27 ± 0.06
25.95
Me Me
Me
Me
H
(+)-δ-amorphene 2.99 ± 0.12
26.55 Me
12
Me hentriacontane 0.69 ± 0.03
27.87
O
H
mayurone 0.79 ± 0.02
28.67 OO
cyclohexylmethyl formate 0.98 ± 0.04
30.19
4
1,13-tetradecadiene 1.24 ± 0.06
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Journal of Organic and Pharmaceutical Chemistry 2023, 21 (4)
1 2 3 4
31.26
Me Me
Me
33
10-methylnonadecane 0.47 ± 0.02
32.41 Me
Me
12
triacontane 0.68 ± 0.03
34.80
MeMe
OMe Me
2
6,10,14-trimethylpentadecan-2-one 0.57 ± 0.03
35.37
CO2iBu
CO2iBu
diisobutyl phthalate 0.97 ± 0.04
37.81
Me
O
OH
5
palmitic acid 19.21 ± 0.77
41.68 CO2H
Me
2 3
linoleic acid 20.08 ± 0.67
41.80 O
33
9,17-octadecadienal 18.57 ± 0.56
47.81 Me Me
9
pentacosane 2.38 ± 0.12
48.73 Me
Me
7
eicosane 3.99 ± 0.15
49.13
Si
O
Si
O
Si
O
2,2,4,4,6,6-hexamethyl-1,3,5,2,4,6-
trioxatrisilinane 2.28 ± 0.11
49.25 N
Ph
Me
5-methyl-2-phenylindolizine 2.13 ± 0.8
49.52 MeMe
Me
8
3-methylheneicosane 2.78 ± 0.10
Table (continued)
Six acyclic saturated hydrocarbons (10.99 ±
0.45 % of the total compounds) were found in the
raw material, namely hentriacontane, 10-methyl-
nonadecane, triacontane, pentacosane, eicosa-
ne, 3-methyl-heneicosane, among them eicosane
(3.99 ± 0.15 % of the total compounds) dominated.
Such groups of BAS as fatty acid derivatives,
aldehydes and dienes, which were detected as a
result of our study, were also found in the results
of the previous studies of the raw material of
C. islandica conducted by the GC/MS method [14].
However, these researchers did not mention the
presence of terpenoids and their derivatives in
the raw material studied. Therefore, there is no
data on the presence of cis-menthone, trans-mentho-
ne, menthol, trans-carane, caryophyllene, β-cube-
bene, γ-murolene, δ-amorphene, mayurone, hexa-
hydrofarnesyl acetone; these data are provided
for the first time.
According to literature data, phenols and their
ethers, aldehydes, and lichen acids dominated
among the compounds identified in the raw ma-
terial, while according to the results of our study,
fatty acids and their derivatives prevailed in
percentage.
The presence of terpenoids and their deriva-
tives, aldehydes in the raw material studied sug-
gests that these compounds play a certain role
in the anti-inflammatory, antiseptic, and expecto-
rant pharmacological activity, which should be
taken into account when developing new substan-
ces and medicinal products based on them.
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Журнал органічної та фармацевтичної хімії 2023, 21 (4)
■ Conclusions
The component composition of compounds dis-
tilled with water vapor in the raw material of C. is-
landica harvested in Ukraine has been studied
by the GC/MS method. 24 compounds distilled
with water vapor have been identified; among
them fatty acids and their derivatives (57.86 ±
2.00 % of the total compounds), terpenoids and
their derivatives (23.57 ± 0.97 % of the total com-
pounds) and acyclic saturated hydrocarbons
(10.99 ± 0.45 % of the total compounds) predo-
minate. For the first time, the presence of 4 mono-
terpenoids and 6 sesquiterpenoids has been de-
termined in the raw material studied. The re-
sults obtained regarding the compounds distil-
led with water vapor in the raw material of C. is-
landica harvested in Ukraine indicate the need
for further research, considering the batches of
the raw material and places of harvesting, pos-
sibly in comparison with the raw material har-
vested outside the country.
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ISSN 2308-8303 (Print) / 2518-1548 (Online) 57
Journal of Organic and Pharmaceutical Chemistry 2023, 21 (4)
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Information about the authors:
Alina O. Shpychak (corresponding author), Ph.D. Student of the Department of Chemistry of Natural Compounds
and Nutritiology, National University of Pharmacy of the Ministry of Health of Ukraine; https://orcid.org/0000-0001-6847-7655;
e-mail for correspondence: shpichakalina@gmail.com; tel. +380 99 4910210.
Olga P. Khvorost, D.Sc. in Pharmacy, Professor of the Department of Chemistry of Natural Compounds and Nutritiology,
National University of Pharmacy of the Ministry of Health of Ukraine; https://orcid.org/0000-0002-9534-1507.
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| id | oai:ojs.journals.uran.ua:article-299297 |
| institution | Journal of Organic and Pharmaceutical Chemistry |
| issn | 2518-1548 |
| keywords_txt_mv | |
| language | English |
| last_indexed | 2026-08-24T01:00:55Z |
| publishDate | 2023 |
| publisher | National University of Pharmacy |
| record_format | ojs |
| resource_txt_mv | ophcjnupheduua/e4/a0cb02f3cc7f211a3ee55c3643d8fce4.pdf |
| spelling | oai:ojs.journals.uran.ua:article-2992972026-08-23T18:33:04Z The Study of Compounds Distilled with Water Vapor in Cetraria islandica (L.) Ach. Thalli Harvested in Ukraine Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні Shpychak, Alina O. Khvorost, Olga P. Cetraria islandica thalli compounds distilled with water vapor GC/MS Cetraria islandica слань сполуки, дистильовані з водяною парою ГХ/МС The component composition and the quantitative content of compounds distilled with water vapor in the thalli of Cetraria islandica (L.) Ach. harvested in Ukraine were determined using the method of gas chromatography with mass spectrometric detection (GC/MS). 24 compounds distilled with water vapor were identified with the prevalence of fatty acids and their derivatives (57.86±2.00% of the total compounds), terpenoids and their derivatives (23.57±0.97% of the total compounds) and acyclic saturated hydrocarbons (10.99±0.45% of the total compounds). The highest percentage was observed for octadecadienoic (linoleic) acid (20.08±0.67% of the total compounds), hexadecanoic (palmitic) acid (19.21±0.77% of the total compounds) and 9,17-octadecadienal (18.57±0.56% of the total compounds). The presence of 4 monoterpenoids and 6 sesquiterpenoids in the raw material studied was determined for the first time. За допомогою методу газової хроматографії з мас-спектрометричним детектуванням (ГХ/МС) визначено компонентний склад та кількісний вміст дистильованих з водяною парою сполук, що наявні у слані Cetraria islandica (L.) Ach., заготовленої в Україні. Ідентифіковано 24 сполуки, дистильовані з водяною парою, серед яких переважали жирні кислоти та їхні похідні (57,86±2,00% від суми сполук), терпеноїди та їхні похідні (23,57±0,97% від суми сполук), ациклічні насичені вуглеводні (10,99±0,45% від суми сполук). Найвищий відсотковий вміст виявлено для октадекадієнової (лінолевої) кислоти (20,08±0,67% від суми сполук), гексадеканової (пальмітинової) кислоти (19,21±0,77% від суми сполук) та 9,17-октадекадієнового альдегіду (18,57±0,56% від суми сполук). Уперше для досліджуваної сировини виявлено наявність 4 монотерпеноїдів та 6 сесквітерпеноїдів. National University of Pharmacy 2023-12-11 Article Article application/pdf https://ophcj.nuph.edu.ua/article/view/299297 10.24959/ophcj.23.299297 Journal of Organic and Pharmaceutical Chemistry; Vol. 21 No. 4 (2023); 51-57 Журнал органической и фармацевтической химии; Том 21 № 4 (2023); 51-57 Журнал органічної та фармацевтичної хімії; Том 21 № 4 (2023); 51-57 2518-1548 2308-8303 en https://ophcj.nuph.edu.ua/article/view/299297/292488 Copyright (c) 2024 Alina O. Shpychak, Olga P. Khvorost http://creativecommons.org/licenses/by/4.0 |
| spellingShingle | Cetraria islandica слань сполуки дистильовані з водяною парою ГХ/МС Shpychak, Alina O. Khvorost, Olga P. Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні |
| title | Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні |
| title_alt | The Study of Compounds Distilled with Water Vapor in Cetraria islandica (L.) Ach. Thalli Harvested in Ukraine |
| title_full | Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні |
| title_fullStr | Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні |
| title_full_unstemmed | Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні |
| title_short | Дослідження сполук, дистильованих з водяною парою, що наявні у Cetraria islandica (L.) Ach. слані, заготовленої в Україні |
| title_sort | дослідження сполук, дистильованих з водяною парою, що наявні у cetraria islandica (l.) ach. слані, заготовленої в україні |
| topic | Cetraria islandica слань сполуки дистильовані з водяною парою ГХ/МС |
| topic_facet | Cetraria islandica thalli compounds distilled with water vapor GC/MS Cetraria islandica слань сполуки дистильовані з водяною парою ГХ/МС |
| url | https://ophcj.nuph.edu.ua/article/view/299297 |
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