FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fra`r[ J[ 1999^ 04] 266Ð271

Essential oils of Satureja boliviana and S. parvifolia

growing in the region of Jujuy, Argentina
Carmen I. Viturro,1 Ana Molina,1 Isabelle Guy,2 Brigitte Charles,2 Hélène Guinaudeau2 and Alain Fournet3
1
Facultad de Ingeneria, Universidad Nacional de Jujuy, Gorriti 237 (4600), San Salvador de Jujuy, Argentina
2
Substances d’Origine Naturelle et Analogues Structuraux, Faculté de Pharmacie, Université d’Angers, 16 boulevard Daviers, 49000
Angers, France
3
Institut de Recherche pour le Développement (IRD), Département ‘Sociétés et Santé’, 213 rue La Fayette, 75480 Paris cédex 10,
France

Received 29 November 0888

Revised 05 May 1999
Accepted 06 May 1999

ABSTRACT] Essential oils of aerial parts of Satureja parvifolia and S[ boliviana of Argentina were analysed by
GCÐMS and GCÐFID[ Fifty!six components were identi_ed[ The main compound of S[ parvifolia essential oil
is piperitenone oxide[ The most abundant constituents identi_ed in S[ boliviana essential oil were g!terpinene\ b!
caryophyllene\ germacrene!D\ bicyclogermacrene\ 0\7!cineol and linalool[ Copyright Þ 1999 John Wiley + Sons\
Ltd[

KEY WORDS] Satureja parvifolia "Phil[# Epl[^ Satureja boliviana Briq[^ Lamiaceae^ essential oil composition^
piperitenone oxide^ g!terpinene^ b!caryophyllene^ bicyclogermacrene^ germacrene!D^ linalool

Introduction vious investigations of essential oil of S[ boliviana and

Satureja boliviana Briq[ and S[ parvifolia "Phil[# Epl[ are
medicinal plants growing in the Andean countries "Peru\
Bolivia and Argentina#[ They are known as {mun½a| or
{khoa| by Kechuas Indians and {poleo| by Spanish
people[0
Both species are traditionally used in medicine and in
cooking[ An infusion of the leaves of S[ boliviana is used
to relieve rheumatism pains\ while the stems are also
employed to relieve migraines or as a stomachic\ sudo!
ri_c or insecticide[1 The branches are used as fuel[ The
aerial parts are widely used] an infusion is employed as
a digestive or antispasmodic or in the treatment of colds^
a decoction is used as a vermifuge and the essential oil
is sprayed on potatoes to project them from pests[2Ð4
S[ parvifolia is traditionally used in Argentina against
digestive disorders\ colds and female sterility[ This plant
is also known as an aphrodisiac and emmenagogue[4\5
It is employed to relieve a disease of the region called
puna\ due to altitude5 "personal communication#[
In the present work we examined the chemical com!
position of two essential oil samples from Argentinian
S[ boliviana and S[ parvifolia collected in the Quebrada
and Valley of Jujuy in the North West of Argentina[
Analysis were performed simultaneously in Argentina
"GCÐFID\ GCÐMS# and in France "GCÐMS#[ Pre!
 Correspondence to] A[ Fournet\ Departement {Societes et Sante|\ 102 rue La
Fayette\ 64379 Paris Cedex 09\ France[ E!mail] alain[fournetÝwanadoo[fr
S[ parvifolia indicated that the chemical composition
varied with origin[3\6Ð05
Experimental
Plant Material
Aerial parts of S[ boliviana were collected by Ana
Molina at the ~owering stage in Argentina near San
Salvador de Jujuy in the Valley area "altitude above
0999 m#[ Aerial parts of S[ parvifolia were collected at
the full ~owering period by Carmen Ines Viturro in
Quebrada of Jujuy "altitude above 2299 m#[ The samples
were identi_ed by O[ Ahumada "Professor at National
University of Jujuy#[ Voucher specimens "Ahumada
5539 and Ahumada 8048\ respectively# have been
deposited at the Herbarium of the Faculty of Agrarian
Sciences\ National University of Jujuy\ Argentina
"JUA#[
Oil Isolation
Fresh aerial parts of the plants were hydrodistilled for
2 h using a Clevenger!type apparatus[ The oils obtained
were dried over anhydrous sulphate[ Essential oil yields
were 9[16) in S[ boliviana and 9[46) in S[ parvifolia
"v:w of fresh sample#[ Samples have been stored after
reception[

Copyright Þ 1999 John Wiley + Sons\ Ltd[

267 C[ I[ VITURRO ET AL[
Essential Oil Analysis
Both samples were investigated by GCÐMS and GC
using fused silica columns of equivalent stationary
phases[ These phases were 4) diphenyl\ 84) dime!
thylpolysiloxane "SPB!4\ HP!4MS\ HP!4\ DB!4#\ 4)
phenyl equivalent\ 84) polysilphenylenesiloxan
"BPX4#[ Complementary analyses were performed on
an apolar DB!0 column to con_rm the identi_cation of
the compounds[
GC–MS Analysis
In France\ S[ boliviana and S[ parvifolia essential oils
were analysed in a ATI UNICAM 509 instrument
linked to a mass spectrometer\ ATI UNICAM 019\
under the following conditions] column BPX4 "14
m×9[11 mm\ _lm thickness 0 mm# programmed at 59Ð
149>C "09 min# at 2>C:min^ carrier gas\ helium "04 psi^
injector temperature\ 139>C^ detector temperature\
149>C^ mass spectra\ electronic impact[ The samples
were diluted in chloroform "0 ] 09# and 9[2Ð9[4 ml were
injected[
In Argentina\ S[ boliviana and S[ parvifolia fresh
essential oils were analysed by GCÐMS using two
di}erent apparatuses with a column of equivalent
stationary phase[ The S[ boliviana sample was analysed
in a GC HP 5789 apparatus linked to a MS HP 4861
spectrometer with a HPÐ4MS column "29 m×9[14 mm\
_lm thickness 9[14 mm#^ carrier gas\ helium "04 psi#^
injector temperature\ 139>C "splitless mode#^ detector
temperature\ 299>C^ column temperature\ 59Ð179>C at
3>C:min^ the sample was diluted with acetone "3 ml:ml#[
The S[ parvifolia sample was analysed by GCÐMS
Shimadzu QP!4999\ using a SPB!4 column "29 m×9[14
mm\ _lm thickness 9[14 mm# under the following con!
ditions] oven temperature\ 59>C "9 min#Ð179>C "09 min#
at 3>C:min\ injector 139>C\ split ratio 0 ] 14^ carrier gas\
helium^ interface temperature\ 179>C^ detector tem!
perature\ 299>C[
GC–FID Analysis
Both samples were investigated in Argentina by GCÐ
FID in a KNK 2999 G "KONIK# equipped with a ~ame
ionization detector "FID#\ using a HP!4 column "29
m×9[14 mm\ _lm thickness 9[14 mm#[ GC Analytical
conditions were as follows] injector temperature\ 149>C^
split ratio 0 ] 49^ column temperature] 59Ð179>C at
5>C:min^ carrier gas hydrogen\ ~ow rate 0 ml:min\
detector temperature 299>C[ Complementary analysis
of S[ parvifolia sample was performed in the KNK 2999
G using a DB!0 column "29 m×9[14 mm\ _lm thickness
9[14 mm# under the following conditions] 59Ð179>C at
3>C:min\ carrier gas helium\ injector temperature
139>C\ detector temperature 299>C[
Copyright Þ 1999 John Wiley + Sons\ Ltd[
Components were identi_ed by comparison of their
Kovats indices06\07 and their mass spectra with those of
several databases[06\08 Kovats indices were calculated on
the basis of a linear regression programme relating the
indices of n!alkanes to the number of scans of the spec!
trometer obtained by analysis of an alkane mixture in
the same conditions[ Kovats indices given by the data!
bases are speci_c for DB!4 and OV!090 columns\ whose
stationary phase are similar to those used here[06\07
Component concentrations were calculated from
GCÐFID areas[
Results and Discussion
The identi_ed compounds of S[ boliviana and S[ parvi!
folia essential oils are listed in Table 0 in order of their
elution from the DB!4 column[
Fifty!six volatile components\ representing 88[5) of
the total oil were identi_ed in the S[ boliviana sample[
The main components and their percentages of S[ boli!
viana essential oils from di}erent origins are listed in
Table 1[ At _rst\ chemical composition of this essential
oil di}ers with those of Bolivian and Peruvian species
whose main components are menthone\ isomenthone
and pulegone[ None of these compounds is identi_ed
in the studied Argentinian sample[ In addition\ this
essential oil contains nearly equal amounts of mono!
terpenes "49[0)# and sesquiterpenes "38[2)#[ The main
compounds are g!terpinene "04[3)#\ b!caryophyllene
"09[1)#\ germacrene!D "7[8)# and bicyclogermacrene
"7[2)#[ Monoterpene hydrocarbons represent 16[6)\
oxygenated monoterpenes 11[3)\ sesquiterpene hydro!
carbones 27[3) and oxygenated sesuiterpenes 09[8)[
Consequently\ the chemical composition of this sample
is di}erent from the Tucuman Argentinian one studied
by Tomasini et al[ "0862#[8 The latter was richer in
monoterpenes\ and the main components were mono!
terpene hydrocarbons "camphene\ 6[8) and p!cymene\
16[4)# and esters "bornyl acetate\ 8[7)\ neryl acetate\
07[5) and geranyl acetate\ 00[7)#[ The chemical com!
position di}erences of these essential oils seem to indi!
cate chemotype existence and show the high in~uence
of environmental factors such as geographic location
and light intensity[
Fifty!six compounds\ representing 86[4) of the
essential oil\ were identi_ed in S[ parvifolia[ This sample
is richer in monoterpene compounds "82[8)#\ essen!
tially in oxygenated monoterpenes "78[6)#[ It contains
only 2) of sesquiterpene compounds "oxygenated\
0[8)^ hydrocarbons\ 1[0)#[ These proportions are in
accordance with those previously calculated in essential
oils of the same species\ as mentioned in Table 2[03Ð05
The main compounds were piperitenone oxide "58[7)#\
piperitenone "4[5)# and pulegone "3[3)#[ Argentinian
Flavour Fra`r[ J[ 1999^ 04] 266Ð271
 ESSENTIAL OILS OF SATUREJA BOLIVIANA AND S[ PARVIFOLIA 268

Table 1. Comparative percentage composition of S. boliviana and S. parvifolia collected

in the region of Jujuy, Argentina
Compounds S[ boliviana ")# S[ parvifolia ")#
Tricyclene 9[6
a!Thujene 9[0 9[0
a!Pinene 9[5 9[2
Camphene 0[3 t
Sabinene 9[7 9[3
b!Pinene 9[3 9[4
Myrcene 9[1 9[8
0!Octen!2!ol 9[5
2!Ocanol t t
o!Cymene 0[3
p!Cymene 1[7 9[0
Limonene 9[5 9[8
0\7!Cineole 6[3 0[1
cis!b!Ocimene 9[0
trans!b!Ocimene 2[3 9[3
g!Terpinene 04[3
cis!Sabinene hydrate t
cis!Linalool oxide t
m!Cymenene t
Linalool 3[7 0[9
trans!Pinan!1!ol 2[8
trans!Thujone 9[0
Dihydrolinalool 9[0
trans!Verbenol 9[0
Isopulegol t
Isoborneol t t
trans!a!Dihydroterpineol t
Borneol 0[9
Menthol t
Terpin!3!ol 9[5 t
p!Cymen!7!ol 9[5
a!Terpineol 9[3
Myrtenal¦myrtenol 9[5
Verbenone t
Cuminaldehyde 9[5
trans!Carveol t
Citronellol 9[5
Pulegone 3[3
Carvone 9[5
Piperitone 9[7
Linalyl acetate 9[3
Geraniol 9[2
trans!Myrtanol 9[7
Citronellyl formiate 0[3
Methyl nerolate 9[5
Bornyl acetate 1[1
Thymol t
Pinocarvyl acetate 9[2
5!Hydroxy!carvotanacetone 9[0
cis!Pinocarvyl acetate¦isoamyl benzyl ether t
trans!Carvyl acetate t
d!Elemene 9[8
Piperitenone 4[5
Piperitenone oxide 58[7
Neryl acetate 9[0
a!Copaene 9[1
b!Bourbonene 9[0
b!Elemene 9[2
a!Gurjunene 9[0
trans!Caryophyllene 09[1 9[8
b!Gurjunene 9[0
Aromadendrene 9[1
cis!b!Farnesene 9[0
a!Humulene 9[8
cis!Muurola!3"03#\4!diene 9[0
allo!Aromadendrene 9[1
g!Muurolene 9[4 t
Germacrene D 7[8
b!Selinene t

Copyright Þ 1999 John Wiley + Sons\ Ltd[ Flavour Fra`r[ J[ 1999^ 04] 266Ð271
279 C[ I[ VITURRO ET AL[

Table 1. Continued
Compounds S[ boliviana ")# S[ parvifolia ")#
Bicyclogermacrene 7[2 0[9
b!Dihydroagarofuran 0[6
a!Muurolene 0[0
g!Cadinene 9[6 9[0
"Z#!Calamenene 0[6
d!Cadinene 1[7
Germacrene!D!3!ol 9[2
Spathulenol 1[0 0[6
Caryophyllene oxide 0[7 9[1
Viridi~orol 9[5
cis!Dihydro!occidentalol 9[0
cis!Isolongifolanone 9[0
b!Oplopenone¦humulene epoxide II 9[3
b!Acorenol t
epi!a!Cadinol 0[3
Cubenol 9[2
a!Cadinol 0[3 t
Oplopanone 9[0
cis!Dihydro!occidentalol acetate 9[0
trans!Dihydro occidentalol acetate 9[0
Compounds are listed in order of elution on a DB!4 column[ ttrace "³9[94)#[

Table 2. Comparative composition of the essential oils of S. boliviana from different regions
Origin Peru3 Peru6 Peru7 Peru7 Argentina Argentina
"aerial parts\ )# "aerial parts\ )# "aerial parts\ )# "aerial parts\ )# "Tucuman#8 "Jujuy#
"leaves\ )# "aerial parts\ )#
a!Pinene 9[2 9[4 9[2 9[6 2[9 9[0
Camphene 9[0 t 9[1 6[8 0[3
p!Cymene 2[3 0[7 3[2 4[3 16[4 1[7
0\7!Cineole 3 3[1 3[1 8[7 0[7 6[3
trans!b!Ocimene 9[0 t 2[3
g!Terpinene 9[7 1[2 9[3 04[3
Linalool 2[0 0[7 2[9 0[3 01[4 3[7
Menthone 13[1 43[0 01[5 9[6
Isomenthone 18[6 04[0 18[9 16[9
Isopulegone 4[4 1[2 9[5
cis!Dihydrocarvone 5[2
Pulegone 09[6 1[1 01[5 19
Piperitone 1[0 0[6 0[2 9
Linalyl acetate 9[0 t 2[7
Bornyl acetate 9[7 8[7 1[1
Thymol 3[4 9[1 5[7 03[6 ¦
Carvacrol 9[0 5[7 9[3 9[6 ¦
Neryl acetate 07[5 9[0
Geranyl acetate 9[0 00[7
b!Caryophyllene 0[5 0[7 9[6 09[1
g!Elemene 0[2
Germacrene D 9[1 9[1 7[8
Bicyclogermacrene 2[9 7[2
d!Cadinene 9[6 9[5 9[0 1[7
Spathulenol 0[2 9[2 1[2 1[0
Caryophyllene oxide t 0[9 9[1 0[7
b!Bourbanol 1[3

Monoterpenes 76[8 77[6 49[0

Monoterpene hydro! 5[3 2[6 00[9 09[8 16[6
carbons
Oxygenated monoterpenes 70[4 74[9 67[4 66[5 11[3

Sesquiterpenes 38[2
Sesquiterpene 3[7 0[8 0[2 1[2 27[3
hydrocarbons
Oxygenated sesquiterpenes 0[9 0[6< 2[0 2[0 09[8

Copyright Þ 1999 John Wiley + Sons\ Ltd[ Flavour Fra`r[ J[ 1999^ 04] 266Ð271
 ESSENTIAL OILS OF SATUREJA BOLIVIANA AND S[ PARVIFOLIA 270

Table 3. Comparative composition of the essential oils of Argentinian S. parvifolia from

different regions
Origin Tucuman03 Tucuman04 Cordoba05 Jujuy
"leaves\ )# "leaves\ )# "leaves\ )# "aerial parts\ )#

a!Pinene 1[2 9[2 9[3 9[2

b!Pinene 0[1 9[1 9[3 9[4
Myrcene 0[9 9[1 9[4 9[8
p!Cymene 03[9 1[7
Limonene 3[3 9[6 4[0 9[8
0\7!Cineole 1[4 t 0[0 0[1
g!Terpinene 00[2 04[3
Menthone 9[0 5[0
Isopulegone 9[4
Menthol 19[1 t
Pulegone 9[8 2[5 3[3
Piperitone 01[7 0[8 9[7
Thymol 7[8
Carvacrol 23[9
Carvacryl acetate 03[6
Pipertenone oxide 30[4 04[9 58[7
Piperitonone 4[5
Piperitone oxide 08[2 29[0
b!Caryophyllene 8[0 9[8
Bicyclogermacrene 0[9

Monoterpenes
Monoterpene hydrocarbons 20[3 5[9 2[6
Oxygenated monoterpenes 52[7 77[0 78[1

Sesquiterpenes
Sesquiterpene hydrocarbons 9[0 1[0
Oxygenated sesquiterpenes 9[6 2[9 0[8

species have been investigated previously[ The chemical References

composition of this sample di}ers with those of Tucu!
man samples studied respectively by de Iglesias03 and
Muschietti[04 The main components of the _rst sample
obtained from leaves were piperitone "01[7)#\ pip!
eritone oxide "30[4)# and piperitenone oxide "08[2)#\
while those found in second sample obtained from
leaves were carvacrol "23[9)#\ carvacryl acetate
"03[6)#\ p!cymene "03[9)# and g!terpinene "00[2)#[
In addition\ the chemical composition of the sample
analysed di}ers also from those of the leaf essential oil
of the same species from area of Cordoba] the main
components of the Cordoba sample were piperitone
oxide "29[0)#\ menthol "19[1)# and piperitenone oxide
"04[9)#[05 The di}erence in oil composition of these
Satureja oils is probably due to the existence of di}erent
chemotypes or to the in~uence of soil\ altitude and
weather conditions[ These in~uences are widely known
in the chemical composition of essential oils from plants
of the Lamiaceae[19Ð11
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Fitoterapia 0884^ 55] 336Ð350[
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Copyright Þ 1999 John Wiley + Sons\ Ltd[ Flavour Fra`r[ J[ 1999^ 04] 266Ð271
271 C[ I[ VITURRO ET AL[
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Copyright Þ 1999 John Wiley + Sons\ Ltd[
Fra`rance Volatiles by Glass Capillary Chromato`raphy[ Aca!
demic Press] New York\ 0879^ 361[
ATI UNICAM 019 database\ nitasci:nbsrbase[
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Flavour Fra`r[ J[ 1999^ 04] 266Ð271