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Mentha aquatica hypeuria Briq. a selection particularly rich in menthofuran.

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In continuation of our research on the genus Mentha, we have found a selection of Mentha aquatica that possesses both a high essential oil content and is rich in menthofuran. We refer to M. aquatica L. var hypeuria Briq (sensu Fiori), Strain No.8. The essential oil was analyzed using gas chromatography while the compounds were identified using gas chromatography-mass spectrometry. The main compounds found were: menthofuran (58.5%), caryophyllene, I,8-cineole, limonene and myrcene.
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DEVELOPMENTS
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18
FLAVORS
AND
FRAGRAN
C ES:
A
WORLD
PERSPECTIVE
Proceedi
ngs
of
th
e 10 t h
International
Congress
of
Essen
ti
a l
Oils,
Fragrances
and
Flav
o rs,
Washington,
DC,
U. S.
A.,
16-20
November
1986
Edited by
BRIAN M. LAWRENCE
R.J
Reynolds Tobacco Company, W i
nsto
n- Salem, NC
27
102,
US
.A.
BRAJA
D. MOOKHERJEE
I
nt
ernational Flavors and Fragrances, Union Beach, NJ 0 77
35
,
US
.A.
BR
IAN
J.
WILLIS
Quest International,
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, Kent TN24 OLT, U K.
ELSEVIER
Amsterdam
-
Oxford
- New Y
ork
- T
okyo
1988
B.M. Lawrence, B.D. Mookherjee
and
B.J. Willis (Editors), Flavors and Fragrances: 141
A World Perspective. Proceedings of
the
10th International Congress of Essential Oils,
Fragrances
and
Flavors, Washington, DC, U.S.A.,
16-20
November 1986
©1988 Elsevier Science Publishers B.V., Amsterdam -
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MENTHA
AQUATICA
VAR.
HYPEURIA
BRIQ.,
A
SELECTION
PARTICULARLY
RICH
IN
MENTHOFURAN
Tommasco
Sacco and
Massimo
Maffei
Istituto
di Botanica Speciale, Facolta di Medicina Veterinaria
dell'Universita
di Torino, Viale
Mattioli,
25
1-10125
Turin,
Italy
ABSTRACT
In continuation of our research on the genus
Mentha,
we
have
found
a
selection
of
Mentha
aquatica
that
possesses both a high
essential
oil
con-
tent
and
is rich in menthofuran.
We
refer
to
M.
aquatica L. var hypeuria
Briq (sensu
Fiori),
Strain
No.8.
The
essential
oil
was
analyzed using gas
chromatography while the
compounds
were
identified
using gas chromato-
graphy-mass spectrometry.
The
main
compounds
found
were: menthofuran
(58.5%), caryophyllene,
I,8-cineole,
limonene
and
myrcene.
INTRODUCTION
Mentha
aquatica
L.,
or watermint as
it
is
commonly
known,
is
a
fairly
common
European
Mentha
species
which
can be
found
almost everywhere in
Eu-
rope, especially in the extreme North.
Most
of
its
known
hybrids
and
vari-
eties
have
been
associated with the presence of menthofuran (1). For
exam-
p1e, menthofuran has
been
characterized as the major
constituent
of
M.
aquatica by a
number
of authors,
e.g.
56.4-89.9% (2), 70.0-89.2% (3), 49.0-
51.0%
(4), 51.3-83.0% (5), 17.1-35.4% (6), 33.0-73.9% (1)
and
43.5-57.8%
(7). Menthofuran has also
been
identified
as a major
constituent
of a
num-
ber of natural
M.
aquatica hybrids as
shown
in Table 1. In addition,
men-
thofuran has
been
found
as a major
component
of
oil
of
specific
genotypes
of
Mentha
arvensis L. var. piperascens Malinv.
40%
(8)
and
M.
x
genti]is
L.
18.1-28.6% (9), 16.2-29.2% (10).
Now,
pulegone is considered to be the only precursor of menthofuran;
142
Table 1. Variation
Found
in Natural
Mentha
Hybrids That
Have
M.
aquatica as
One
of the Parents
Natural
Mentha
Hybrid
Menthofuran Percentage Reference
M.
x
dumetorum
Schultes
M.
x
maximi7anea
F.
W.
Schultz
M.
x
piperita
L. Flowers
Flowers
M.
xvertici77ata
L.
25.1
24.3 - 27.3
24.8 - 33.0
1.0 - 37.4
2 -
12
20.1
21.5
41.4 - 73.5
o - 33.4
5
1
7
1
13
14
1
15
1
although
it
is almost
always
absent in
distilled
oils
of
M.
aquatica.
However,
this
supports the idea
that
conversion of pulegone to menthofuran
is
an
efficient
reaction (11).
According to Furia
and
Bellanca (12), menthofuran
which
has a sweet
men-
thol-like
flavour, is used in flavouring non-alcoholic beverages, ice
cream
and
candy
by
the flavour industry.
Mentha
aquatica L. var. hypeuria Briq.
(sensu Fiori)
strain
no. 8,
which
can be
found
growing spontaneously in the
Piedmont
(Italy)
was
selected over other
members
of the Capitatae section
because of
its
richness in menthofuran.
It
has a
chromosome
number
of
2n=96,
in accordance with the Karyological reference to
M.
aquatica data.
Morpho
1ogi
cally
thi
s
strain
possesses asuberect branched hairy stem.
The
slight
hairy
and
serrated leaves are ovate-lanceolate.
The
inflores-
cences are
composed
of congested
verticillasters,
while the flowers
have
a
purplish corrola.
Over
the years, the
morphology
of the plant
and
chemical
composition of the oil has
been
found
to be very
stable.
EXPERIMENTAL
The
plants were harvested at
random
when
they were in
full
bloom
and
then steam
distilled.
Dry
and
fresh
yields
were
calculated.
The
essential
oils
were analyzed chromatographically using a Carlo Erba
4160
gas chromat-
143
ograph with a flame ionization
detector.
Separation
was
done using a 30-
meter fused
silica
column
coated with
Carbowax
20M.
Operating conditions:
Injection temperature:
230
0C,
hydrogen
carrier
gas flow: 1.5
ml
min-I.
Temperature
programming
was
as follows: 3
min
isothermal
at
60 °C, then a
linear
temperature
rise
of 3 0c
min-
1to
180
0C.
The
compounds
were iden-
tified
using gas chromatography-mass spectrometry. A Hewlett-Packard
5995B
GC/MS
system with a 50-meter fused
sil
ica col
umn
coated with
Carbowax
20M
and a helium
carrier
gas flow
rate
of 1.5
ml
min-I.
The
mass
spectra
were
obtained
at
70
eV.
The
injector
temperature
was
230
°C
and the ion source
temperature
was
250
°C.
RESULTS
AND
DISCUSSION
The
oil
composition of M.
aquatica
var.
hypeuria
Strain
No.
8 can be
seen in Table 2.
The
main
components
were menthofuran (58.5%), caryophyl-
lene (8.39%), 1,8-cineole (5.45%), limonene (4.65%),
viridiflorol
(2.13%)
and
myrcene
(1.66%).
It
is of
interest
to note
that
the
oil
lacks both
menthol
and pulegone,
and
only contains a very small
amount
of
menthyl
ace-
tate
(0.35%).
The
%plant dry weight
was
28.98 (s2=.072; +/- .815, at
P=.05). Fresh and the dry
yields
were 1.43 ml/kg and 4.93 ml/kg
respectively.
Strain
no. 8 of
this
cultivar
reflects
our previous
investigations
on
other menthofuran-rich
varieties
of M.
aquatica
L. (16). This
strain
is
particularly
interesting
because of the presence of high percentage of
men-
thofuran, beta-caryophyllene and 1
imonene.
This
compos
it ion suggests the
possibil
ity
of
employing
it
in hybridization techniques
for
breeding
and
selecting
new
interesting
mint
cultivars,
which
could be
utilizable
in the
aroma
industry such as M.
arvensis
var.
piperascens
(which
is
rich
in
menthol).
SUMMARY
An
Italian
strain
of Mentha
aquatica
was
found
to possess a high
oil
content
which
was
menthofuran-rich. Because of
this,
we
sugg.est
that
it
be
used in hybridization studies with menthol-rich M.
arvensis
var.
piperas-
cens to obtain
new
and
interesting
mint progeny
which
could produce
oils
of
144
value to the flavour
and
fragrance industry.
Table 2.
Chemical
Composition of the Oil of Mentha
aquatica
var.
hypeuria
(Strain
No.8)
Peal<
No.
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
Name
a-pinene
a-pinene
sabinene
myrcene
1
imonene
1,8-cineole
s-phel Iandrene
ocimene
p-cymene
l-octen-3-yl acetate
menthofuran
menthyl
acetate
neryl acetate
s-caryophyllene
trans-S-farnesene
a-humulene
germacrene D
sesqui alcohol
unl<nown
carophyllene oxide
viri
difl
orol
Area Percentage
0.21
0.58
0.30
1.66
4.65
5.45
0.84
0.20
0.17
0.22
58.50
0.35
0.46
8.39
1.11
1.13
0.96
0.28
0.25
0.61
2.13
REFERENCES
1. B.
M.
Lawrence,
A Study of the
Monoterpene
Interrelationship
in the
Genus
Mentha with Special Reference to the Origin of Pulegone and
Men-
thofuran.
PhD
Thesis,
Groningen
State
Univ., (1978).
2. F.
W.
Hefendehl, Arch. Pharm., 300,
438
(1967).
3.
O.
Sticher and
H.
Fluecl<,
Pharm.
Acta Helv., 43,
411
(1968).
... Data are expressed as ranges of area percentage. Reference data are from: M. aquatica (Malingré & Maarse 1974; Sacco & Maffei 1988; Stafford et al. 2008; van Staden et al. 2007; Zebelo et al. 2011), M. spicata (Gershenzon et al. 1989; Maffei et al. 1986; Maffei 1990), M. arvensis (Lawrence 2007b), M. longifolia (Gulluce et al. ...
Article
Full-text available
The genus Mentha is of particular economic importance. The development of new methods for the characterisation of Mentha species is crucial for their unequivocal identification. Amplification of the non-transcribed spacer (NTS) of the 5S-rRNA gene was used to characterise some Mentha species, which revealed a high-specific variability. Cloning and sequencing of all amplified NTS fragments enabled the discrimination among almost all species. In silico and experimental analyses identified specific restriction sites on the amplified 5S-NTS regions, facilitating the rapid and unambiguous discrimination of all the different species by polymerase chain reaction–restriction fragment length polymorphism. A direct comparison between essential oil composition and DNA fingerprinting confirmed a relationship between chemical and molecular data.
Chapter
The genus Mentha belongs to the family Lamiaceae; it occurs in all five continents, although its native occurrence in the New World is restricted to a single species in the North. It is infrequent in the Tropics, and in Australia there are a number of species, with unclear relationships to the rest of the genus. Although the genus consists of approximately 25 species and rather fewer hybrids, one can find more than 900 binomials listed in the Index Kewensis.
Article
Full-text available
The effect of the herbicide paraquat was studied in the menthofuran-rich Mentha x verticillata strain No. 60 leaf discs, cuttings and rooted plants in pots. Application of paraquat affected the menthofuran biosynthetic pathway, with a clearly different response in wounded tissues. The mechanism of regulation of menthofuran biosynthesis after paraquat treatment was at the transcriptional level. The role of monoterpene turnover in stress response is also discussed.
Article
Hybridization of species belonging to the genus Mentha is quite common. However, the indicators of hybridity are many and make difficult Mentha hybrids identification. By using the same molecular strategy that allowed us to unequivocally identify some Mentha species, we amplified the NTS (Not-Transcribed-Spacer) of the 5S-rRNA gene to characterise the industrial crop peppermint, M. x piperita, and some important Mentha interspecific hybrids: M. x dalmatica, M. x dumetorum, M. x rotundifolia, M. x maximilianea, M. x smithiana, M. x verticillata, M. x villosa. DNA amplification, sequence and cluster analysis revealed differences in the 5S-rRNA NTS region of Mentha hybrids. Peppermint and all other hybrids were unequivocally discriminated by RFLP analysis by using TaqI restriction enzyme, while a further discrimination between M. x dumetorum and M. x verticillata was obtained by XhoI restriction enzyme. Essential oil composition showed clustering patterns similar to DNA fingerprint, with a clear discrimination between plants producing menthofuran (e.g., M. aquatica and its related hybrids, including peppermint) and those containing piperitenone oxide (M. longifolia and its related hybrids). Download at http://www.tandfonline.com/eprint/FaaxdmkX4a2tTv6vUX9v/full
Article
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