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Germacrene D Chemotype of Essential Oils of Leonurus cardiaca L. Growing Wild in Vilnius District (Lithuania)

DOI:10.1080/10412905.2006.9699169
Authors:
Danute Mockute
Danute Mockute
Danute Mockute
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Genovaite Bernotiene
Genovaite Bernotiene
Genovaite Bernotiene
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Asta Judzentiene at State Research Institute Center for Physical Sciences and Technology
Asta Judzentiene
  • State Research Institute Center for Physical Sciences and Technology
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Abstract

The essential oils of wild Leonurus cardiaca L. collected at full flowering in six habitats in Vilnius district were analyzed by GC and GC/MS. About the half of the oils were consisted of sesquiterpene hydrocarbons (48.8–62.2%). The oils from fresh dried plants were of the germacrene D (26.6–35.1%) chemotype. The other main constituents were β-caryophyllene (5.8–9.0%) and α-humulene (6.4–9.2%). Forty-nine identified compounds made up 73.1–84.8% of the oils.
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Mockute et al.
566/Journal of Essential Oil Research Vol. 18, September/October 2006
Received: May 2005
Revised: July 2005
Accepted: October 2005
1041-2905/06/0005-0566$14.00/0—© 2006 Allured Publishing Corp.
J. Essent. Oil Res., 18, 566-568 (September/October 2006)
*Address for correspondence
Introduction
Leonurus cardiaca L. was described in medicinal literature
from the 10
th
century as an herb healing nervous and functional
cardiac disorders (1-4). The local names in France, German,
Russia, Hungary, Lithuania and some other countries included
words which showed connection with the word heart. The healing
of heart diseases is mainly connected with flavonoids (5). Some
local names of L. cardiaca included the word mother, for example
the name motherwort is used in English-speaking countries,
the name ‘matere’ in Latvia. The healing of women’s diseases
is connected with alkaloids. Leonurus cardiaca is an oil-poor
plant producing only <0.01-0.05% of volatile compounds (6).
The plants growing in countries of North America produced
α-humulene and β-caryophyllene as the major constituents
of the oils (6). The amount of germacrene D in the oil of wild
L. cardiaca from Canada was only 0.05% (6). Germacrene D
(24.0%) dominated in the oil of L. masrubiastrum L. grown
in an experimental garden in southern Ontario (seeds from
the Bonn Botanic Garden) (6). The marked percentage of
germacrene D (16.3%) was determined in the oil of L. sibiricus
L. grown in the above experimental garden (seeds collected
in Brazil). Lawrence after analysis of a great number of plant
oils and data from literature on oils composition indicated that
the oil of oil-poor plant species were rich in sesquiterpene
hydrocarbons, with germacrene D often being of predominant
compound (6).
Germacrene D Chemotype of Essential Oils of
Leonurus cardiaca L. Growing Wild in Vilnius District
(Lithuania)
Danute Mockute, Genovaite Bernotiene* and Asta Judzentiene
Institute of Chemistry, A.Gostauto 9, LT-01108 Vilnius, Lithuania
Abstract
The essential oils of wild Leonurus cardiaca L. collected at full flowering in six habitats in Vilnius district were
analyzed by GC and GC/MS. About the half of the oils were consisted of sesquiterpene hydrocarbons (48.8-62.2%).
The oils from fresh dried plants were of the germacrene D (26.6-35.1%) chemotype. The other main constituents
were β-caryophyllene (5.8-9.0%) and α-humulene (6.4-9.2%). Forty-nine identified compounds made up 73.1-84.8%
of the oils.
Key Word Index
Leonurus cardiaca, Labiatae, essential oil composition, germacrene D.
There are no data on the composition of the oils of L.
cardiaca growing wild in Lithuania (7). The aim of the present
paper is to study oils of motherwort growing wild in Vilnius
district (Lithuania).
Experimental
Plant material: The aerial parts of Leonurus cardiaca
were collected at full flowering in six localities in Vilnius district
(Lithuania) in 2000-2004: A – Rokantišk˙es, B – Sapiegyn˙e, C
– Verkiu˛ ežeras, D – Antakalnis, E – Nemencˇin˙e, F – Zuju¯ nai.
The voucher specimen has been deposited in the Herbarium
of Institute of the Botany (Bilas), Vilnius, Lithuania (Numbers:
A-67292, B-67290, C-67293, D-67287, E-67303, F-67304).
The plant samples dried at room temperature (~20°C) were
used for analysis. The oils (0.01-0.02%) were collected in
mixture of hexane and diethyl ether (1:1) during hydrodistil-
lation for 2 h.
Analysis of the oils and identification of the compo-
nents: GC/MS analyses were performed using a chromatograph
interfaced with an HP 5971 mass spectrometer (ionization
voltage 70 eV) and equipped with a CP-Sil 8 CB capillary
column (50 m x 0.32 mm, film thickness 0.25 µm). The oven
temperature was held at 60°C for 2 min, then programmed
from 60°-160°C at a rate of 5°C/min, and then programmed
to 250°C
at a rate of 10°C/min, held for 5 min, using He as a
L. cardiaca
Vol. 18, September/October 2006 Journal of Essential Oil Research/567
Table I. Chemical composition of essential oils of wild Leonurus cardiaca L. from Vilnius district (Lithuania)
Compound RI
a
A B C D E F
2000 2000 2004 2003 2003 2004 2004 2004
α-pinene 939 0.3 1.0 1.1 0.2 0.7 2.3 2.4 0.8
1-octen-3-ol 979 0.3 1.2 1.8 0.6 0.5 0.5 2.1 1.3
(Z)-β-ocimene 1037 0.1 0.2 0.3 0.4 0.3 0.1 0.6 0.3
phenylacetaldehyde 1042 0.2 0.4 0.3 0.3 0.4 0.2 0.7 0.2
cis-sabinene hydrate 1070 t 0.1 t 0.1 0.1 0.1 0.1 t
p-mentha-2,4(8)-diene 1088 - - - t - - 0.6 -
δ-elemene 1338 0.1 0.2 0.2 t 0.2 0.1 0.1 0.6
eugenol 1359 t 0.4 0.9 0.4 0.5 0.2 0.6 0.1
α-copaene 1376 0.4 0.6 0.6 0.4 0.4 0.1 0.5 0.5
β-bourbonene 1384 1.8 0.8 0.8 0.6 0.9 1.6 0.9 0.7
β-elemene 1391 1.1 1.9 1.6 2.1 1.9 0.3 1.9 1.8
n-tetradecane 1400 t 0.9 1.5 - 1.0 t - t
β-caryophyllene 1419 8.9 5.8 6.0 8.7 7.4 9.0 8.7 6.3
β-ylangene 1421 t 0.2 t 0.3 0.2 0.1 0.2 t
β-gurjunene 1434 2.6 2.5 2.2 2.6 2.5 1.3 2.4 2.3
γ-elemene 1437 0.1 - 0.4 t - t 0.1 0.9
β-copaene 1432 0.5 1.1 1.0 1.5 1.0 0.2 1.1 0.1
α-humulene 1454 8.8 6.5 6.5 8.2 7.3 9.2 7.7 6.4
(E)-2-dodecenal 1466 0.2 - 0.7 0.2 - t 0.3 0.1
cis-muurola-4(14),5-diene 1467 1.0 1.0 - 1.0 1.0 t 0.6 0.8
germacrene D 1485 28.3 32.0 28.7 35.1 30.3 26.6 29.7 30.5
bicyclogermacrene 1494 0.4 0.2 t 0.2 0.2 0.2 t 1.2
trans-muurola-4(14),5-diene 1494 0.2 0.4 t 0.4 2.0 0.1 1.6 1.2
δ-cadinene 1523 1.0 1.0 1.1 1.1 0.8 t 1.2 1.0
(Z)-3-hexenyl benzoate 1567 t 0.2 t - t - - 0.2
germacrene D-ol 1576 0.2 0.6 0.6 0.8 1.0 0.5 0.6 0.8
spathulenol 1578 0.2 0.2 0.5 0.2 0.3 1.0 t 0.1
caryophyllene oxide 1580 3.8 0.6 1.0 0.7 0.7 2.2 0.9 1.2
humulene epoxide II 1608 t 0.7 0.9 0.2 0.7 - 0.7 0.9
epi-α-cadinol 1640 0.1 - 0.3 t 0.1 t 0.5 0.6
epi-α-muurolol 1642 0.2 0.6 0.1 0.1 0.2 0.1 t 0.3
α-eudesmol 1652 - t - - t - 0.2 0.9
α-cadinol 1654 0.5 1.0 1.0 0.8 0.6 0.1 0.5 1.1
selin-11-en-4-α-ol 1660 t 0.6 0.1 t 0.6 t - -
heptadecane 1700 0.2 0.9 1.3 1.7 1.7 1.0 0.2 0.3
(E,Z)-farnesol 1725 0.5 0.2 0.2 t 0.1 1.1 0.3 0.6
(Z,Z)-farnesol 1746 0.2 0.3 t 0.2 0.2 t - 0.1
dibutyl phthalate 1790 9.9 11.2 12.4 4.2 7.1 15.4 7.1 13.8
octadecane 1800 1.7 0.2 0.8 0.1 t t 1.6 2.7
(2Z,6E)-farnesyl acetate 1822 t t 2.1 t t t 0.9 1.1
(2E,6E)-farnesyl acetate 1847 0.8 t t 0.1 t 0.1 - t
nonadecane 1900 t 0.6 0.8 t 0.8 1.2 0.8 0.6
phytol 1943 2.5 4.6 4.1 3.8 4.1 4.0 7.2 4.6
eicosane 2000 0.7 0.2 0.3 0.2 1.1 1.9 0.4 0.1
heneicosane 2100 t 1.5 1.9 0.8 0.2 t 1.9 1.9
docasane 2200 2.2 0.2 0.2 0.9 0.1 3.1 0.2 0.1
tricosane 2300 1.1 0.2 1.0 0.7 0.3 1.8 1.5 1.5
tetracosane 2400 1.8 0.4 0.1 0.6 0.2 1.6 t 0.1
pentacosane 2500 0.1 1.9 5.4 0.1 1.2 4.8 2.1 2.4
Total 83.0 85.7 89.8 79.6 81.0 92.1 91.7 93.1
Monoterpene hydrocarbons 0.4 2.2 1.4 0.6 1.0 2.4 3.6 1.1
Oxygenated monoterpenes t 0.5 0.9 0.5 0.6 0.3 0.7 0.1
Sesquiterpene hydrocarbons 55.2 54.2 49.1 62.2 56.1 48.8 56.7 54.3
Oxygenated sesquiterpenes 6.5 4.8 6.8 3.1 4.5 5.1 4.6 7.7
Terpenoids 64.6 66.3 63.3 70.2 66.3 60.6 72.8 67.8
a
RI – retention index on nonpolar column CP-Sil 8CB; the letters indicate growing locations; t = trace (< 0.05%)
Mockute et al.
568/Journal of Essential Oil Research Vol. 18, September/October 2006
carrier gas (1.0 mL/min). The injector and detector temperatures
were 250°C.
GC analysis was performed with a HP 5890II chromatograph
equipped with a FID and a capillary column HP-FFAP (30 m
x 0.25 mm, film thickness 0.3 µm) was used for quantitative
analysis. The GC oven temperature was set at 70°C for 10 min
and then programmed from 70°-210°C at a rate of 3°C/min,
using He as a carrier gas (0.7 mL/min). The injector and detector
temperatures were 200°C and 250°C, respectively.
The percentage composition of the oils was computed from
GC peak areas without correction factors (8). Qualitative analysis
was based on the comparison of retention times and the mass
spectra with corresponding data in the literature (9) and the
computer mass spectra libraries (Wiley and NBS 54K).
Results and Discussion
The flowering tops (30-40 cm) of L. cardiaca were collected
in six localities during 2000-2004 (Table 1, A-E). The herbs
were oil-poor (~ 0.01-0.02%). The plants in two habitats (B,
D) were collected twice in different years. The variations of
chemical composition of the oils from the same locality were not
marked. The dominant constituent germacrene D in population
B varied from 28.7-32.0% and in habitat D from 26.6-30.3%.
The differences in the amounts of the first major constituent
germacrene D in localities under study were more marked
(26.6-35.1%) than corresponding differences in the one habitat.
The amounts of the second and the third main constituents
sesquiterpene hydrocarbons β-caryophyllene and α-humulene
varied from 6.0-9.0% and from 6.4-9.2%, respectively. About
the half of the investigated oils consisted of sesquiterpene
hydrocarbons (48.8-62.2%). Monoterpenoids made up only
0.4-4.3%. The amount of oxygenated sesquiterpenes (3.1-7.7%)
and the oxygenated diterpene phytol (2.5-7.2%) exceeded the
amount of monoterpenoids in all the oils under study. The sum
of terpenoids varied from 60.6-72.8% in the oils, along with
some aliphatic and aromatic compounds in low percentages.
All identified constituents made up 81.1-93.1%. The origin of
dibutyl phthalate (4.2-15.4%) is an artifact (10,11), it could
be accumulated by plants from polluted soils and/or enviro-
ment. The amount of 49 identified constituents comprised
73.1-84.8% of the oils.
The amounts of mono- and sesquiterpene hydrocarbons
decreased by evaporation and/or transformation during plant
storage. The smaller part of β-caryophyllene and α-humulene
was oxygenated in plants during long storage. The changes in
solution (hexane + diethyl ether, 1:1) of the oils during storage
in refrigerator in stoppered glass vessels containing air differed
from those of the oils from stored plants. A large part of β-
caryophyllene and α-humulene was oxygenated in the above
vessels. The amounts of compounds with caryophylane (β-caryo-
phyllene + caryophyllene oxide) and humulane (α-humulene +
humulene oxide II) carbon skeletons were nearly the same in
the fresh and stored oils. The part of mono- and sesquiterpene
hydrocarbons might be evaporated and/or transformed to their
derivatives during storage of the oils.
The composition of L. cardiaca oils depended on storage
of the plants and the oils prior to analysis.
References
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3. S. Mills, K. Bone. Principles and Practice of Phytotherapy. pp.204, 233,
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Fitoterapia. pp.37,170, 312. Biznio mašinu˛ kompanija, Vilnius (2002). (in
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the Concil of Europe (EDQM), Strasbourg, France (2003).
6. B.M. Lawrence, Essential oils 1988-1991. pp.188-206, Allured Publishing
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7. Lekavicˇius, Leonurus L. In: Flora of Lithuania. Edit., M.Natkevicˇaite˙-
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Book
  • Jan 2012
The authoritative and comprehensive modern textbook on western herbal medicine - now in its second edition This long-awaited second edition of Principles and Practice of Phytotherapy covers all major aspects of herbal medicine from fundamental concepts, traditional use and scientific research through to safety, effective dosage and clinical applications. Written by herbal practitioners with active experience in clinical practice, education, manufacturing and research, the textbook is both practical and evidence based. The focus, always, is on the importance of tailoring the treatment to the individual case. New insights are given into the herbal management of approxiately 100 modern ailments, including some of the most challenging medical conditions, such as asthma, inflammatory bowel disease and other complex autoimmune and inflammatory conditions, and there is vibrant discussion around the contribution of phytotherapy in general to modern health issues, including health ageing. Fully referenced throughout, with more than 10, 000 citations, the book is a core resource for students and practitioners of phytotherapy and naturopathy and will be of value to all healthcare professionals - pharmacists, doctors, nurses - with an interest in herbal therapeutics.
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Volatile compounds isolated from edible Korean Chamchwi (Aster scaber Thunb)
Article
  • Oct 1993
The volatile concentrate obtained from the edible Korean chamchwi plant (Aster scaber Thunb) by a distillation-extraction system was separated into hydrocarbon and oxygen-containing fractions, and the latter was further separated into eight subfractions by silica gel column chromatography. Gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS) were utilized to identify 119 volatile compounds in the fractions. The volatile compounds included 55 hydrocarbons, 37 alcohols, 11 aldehydes, 5 oxides, 4 esters, 4 ketones, 2 acids, and 1 phenol. Myrcene, a monoterpene hydrocarbon, was the most abundant volatile compound identified in chamchwi (18.80%). Chamchwi oil was found to possess a woody or herbaceous aroma following sensory evaluation of each fraction and individual volatile component using a GC-sniff apparatus.
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Identification of major components of the oil essential of mace
Article
Gas chromatographic and combined gas chromatographic-mass spectrometric analysis of the essential oil of mace has shown that it consists of a mixture of approximately 87.5% monoterpenes, 5.5% monoterpene alcohols, 6.5% aromatic ethers, together with 0.5% other components. Nine-monoterpene hydrocarbons, six monoterpene alcohols, two aromatic hydrocarbons, one sesquiterpene and six aromatic ethers have been identified.
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Pharmacological effects of lavandulifolioside from Leonurus cardiaca
Article
Lavandulifolioside was detected for the first time in Leonurus cardiaca var. vulgaris [Moench] Briquet (Lamiaceae). The isolation was performed from the butanolic extract of the aerial parts and the identification by NMR and MS. The pharmacological properties of lavandulifolioside consist of significant negative chronotropism, prolongation of the P-Q, Q-T intervals and QRS complex, and decrease of blood pressure. Contrary to the butanolic extract lavandulifolioside did not reduce the spontaneous locomotor activity. In conclusion, the pharmacological pattern of lavandulifolioside did not explain the pharmacological effects of L. cardiaca L. alone.
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Handbook of medicinal plants. Prevencijos
  • Jan 2002
  • 265-267
  • V Sasnauskas
V. Sasnauskas. Handbook of medicinal plants. Prevencijos, pp. 265-267 Dajalita, Kaunas (2002). (in Lithuanian)
Essential oils 1981-1987
  • Jan 1998
  • B M Lawrence
B.M. Lawrence, Essential oils 1981-1987. p.7, Allured Publishing Corporation, Carol Stream, IL (1998).
Address for correspondence References
  • Oct 2006
  • 566-568
  • Accepted
Accepted: October 2005 1041-2905/06/0005-0566$14.00/0—© 2006 Allured Publishing Corp. J. Essent. Oil Res., 18, 566-568 (September/October 2006) *Address for correspondence References
  • Jan 1976
  • 331-333
  • Leonurus L Lekavičius
Lekavičius, Leonurus L. In: Flora of Lithuania. Edit., M.Natkevičaitė-Ivanauskienė, Vol. 5., pp. 331-333, Mokslas, Vilnius (1976).
  • Jan 2002
  • 312
  • P Dagilis
  • B Dagilytė
  • A Juocevičius
  • B Mackevičienė
  • A Mackevičius
P. Dagilis, B. Dagilytė, A. Juocevičius, B. Mackevičienė and A. Mackevičius, Fitoterapia. pp.37,170, 312. Biznio mašinų kompanija, Vilnius (2002). (in Lithuanian)