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2011
NPC Natural Product Communications Vol. 6
No. 10
Chemical Composition of the Essential Oil from Corsican 1479 - 1482
Mentha aquatica - Combined Analysis by GC(RI), GC-MS
and 13C NMR Spectroscopy
Sylvain Sutour, Félix Tomi*, Pascale Bradesi and Joseph Casanova
Université de Corse-CNRS, UMR 6134 SPE, Equipe Chimie et Biomasse, Route des Sanguinaires,
20000 Ajaccio, France
felix.tomi@univ-corse.fr
The essential oil (EO) of M. aquatica L. growing wild in Corsica was isolated by dry vapor distillation and submitted to combined analysis
by column chromatography over silica gel, GC(RI), GC-MS and 13C NMR spectroscopy. The composition was dominated by oxygenated
monoterpenes and characterized by the occurrence of menthofuran (50.7%) as the major component. In parallel, seven laboratory-distilled oil
samples isolated from individual plants collected in Corsica were analyzed by GC(RI) and 13C NMR spectroscopy. Only quantitative
differences were observed between the samples. Beside the usual terpenes, various p-menthane lactones (mintlactone, isomintlactone,
hydroxymintlactone, menthofurolactone and epimenthofurolactone) have been identified in all the oil samples.
Keywords: Mentha aquatica L., essential oil composition, menthofuran, 13C NMR, p-menthane lactone.
The genus Mentha L. (Labiatae family) includes 18 species combinations of menthofurane with sesquiterpenes
and various hybrids with several species being cultivated have been reported for Turkish oils: menthofurane/
for essential oil production [1a]. In Corsica, mints are -caryophyllenne (11.4-32.8%/9.6-20.2%); menthofurane/
represented by four species (M. aquatica, M. pulegium, M. elemol (11.1-34.2% /11.6-24.4%), as well as -
requienii and M. suaveolens). M. aquatica L., commonly caryophyllene/viridiflorol (15.0-19.1%/15.7-26.7%) [7b].
known as water mint, wild mint or marsh mint, is called Despite a different chemical composition, EOs from
“pedi rossu”. It grows in wet places, banks of rivers, Ethiopia [2b], Yugoslavia [4a] and Turkey [5] have shown
marshes, and sometimes directly in water [1b]. fair antibacterial activity, mostly against Gram+ bacteria.
The menthofuran/cineole-rich oil from Yugoslavia showed
The composition of the essential oil (EO) of M. aquatica significant fungistatic and fungicidal activity [4a]. The
has been investigated. Various compositions have been Ethiopian menthofuran-rich EO possessed a good radical
reported depending on the countries of harvest. According scavenging activity [2b]. M. aquatica oil containing
to the literature, three types of oils may be distinguished. sesquiterpene alcohols showed effective inhibition of
The first group contains samples where menthofuran is by acetylcholinesterase (AChE) activity and a potent
far the major component: oils from Germany, 70-89% inhibitory activity [8a]. Viridiflorol from the essential oil
[2a]; Ethiopia, 70.5% [2b]; USA, 66.4% [2c]; Italy, 38.4- has been isolated by bioassay-guided fractionation with
59.7% [2d,3a,3b]; Japan, 45.5% [3c]; and Croatia, 42.8% binding to the GABA-benzodiazepine site [8b].
[3d]. Other oil samples exhibited menthofuran (8.1-23.2%)
and cineole (14.2-27.2%) as major components: for In continuation of our previous studies on Corsican mints
instance, oils from the Netherlands) [3e], Yugoslavia [4a] [8c,8d], the aim of the present study was to characterize
and Iran [4b]. Finally, a third group emerged, containing M. aquatica growing wild in Corsica. An oil sample
oil samples with various compositions dominated either by isolated by dry-vapor distillation (pilot plant, commercial)
cineole (55.3%, Turkey) [5]; menthone (77.8%, Brazil) and seven individual samples isolated by water distillation
[6], or piperitenone oxide and -caryophyllene (25.7% and (laboratory scale) have been investigated using a
22.4%, respectively, Iran) [7a]. In addition, limonene combination of various chromatographic and spectroscopic
and terpinen-4-ol, as well as germacrene D, (Z)- and techniques.
(E)--caryophyllene, caryophyllene oxide, -elemol and
viridiflorol were present in substantial amounts in some Aerial parts of M. aquatica produced by dry vapor
samples [3b,3d,4a]. Moreover, -elemol and viridiflorol distillation give an almost colorless essential oil. The bulk
(14.8 and 9.1%, respectively) have been reported as major sample was analyzed by GC in combination with
components of a Japanese sample [3c]. In parallel, various Retention Indices (RI), by GC-MS and by 13C NMR
1480 Natural Product Communications Vol. 6 (10) 2011 Sutour et al.
spectroscopy (Table 1). Various compounds were an irregular monoterpene, rarely found in essential oils,
identified by comparison i) of their mass spectral data with was identified by 13C NMR spectroscopy in the more polar
those of reference compounds compiled in computerized fraction (F2-3) of the CC and quantified in the EO by
libraries [9a-9c]; ii) of their RIs with those of either comparison of its retention indices on both columns.
authentic compounds or literature data (Table 1); and iii) Interestingly, fraction F2-3 contained also five p-menthane
of their 13C NMR spectroscopic data with those of lactones, identified by 13C NMR spectroscopy by
authentic compounds compiled in our laboratory-made comparison of their spectral data with those reported in the
library, following a method developed by our group literature: mintlactone (23.5%), iso-mintlactone (2.5%),
[10-12]. Although all the major components were menthofurolactone (0.6%), epi-menthofurolactone (0.8%)
identified and allowed the classification of that oil among and hydroxymintlactone (3.1%) [13a,13b]. Their relative
the menthofuran-rich oils, various minor components contents in fraction F2 and in the EO were assessed
remained either unidentified or only suspected by MS with through their retention indices on apolar and polar GC
poor library fit. Therefore, the bulk sample was submitted columns (Table 1). Despite the similarity of the structures
to repeated column chromatography (CC) and all the of each pair of epimers, the number of overlapped signals
chromatographic fractions were analyzed by GC(RI) and in the 13C NMR spectrum of fraction F2-3 of the CC was
13
C NMR spectroscopy. In total 35 components (31 very low (only one overlap for each epimer). Although
monoterpenes and 4 sesquiterpenes), accounting for 97.0% these lactones, except hydroxymintlactone, have been
of the EO, were identified (Table 1). The composition of previously identified in an EO from M. piperita L.
the EO was dominated by oxygenated monoterpenes [13a,13b], it is the first time that they were identified in an
(74.6%), whereas monoterpene hydrocarbons (14.6%) and EO from M. aquatica and it could be supposed that they
sesquiterpenes (8.5%) were minor compounds. are volatile compounds produced by the plant. Indeed, the
Menthofuran (50.7%) was by far the major component of distilled oil samples had been stored in the refrigerator in
the EO while 1,8-cineole (5.9 %), limonene (5.3 %) and closed vials and analyzed 1-3 days after distillation.
borneol (3.5%) occurred in lesser amounts. The identified However, it is not possible to ascertain that the five
sesquiterpenes were viridiflorol (3.5%), (E)-- lactones are not (or are in part) artefacts resulting from the
caryophyllene (2.9%) and germacrene D (2.0%). Lyratol, oxidation of menthofuran. Indeed, it has been
Table 1: Volatile components of the leaf oil from Corsican Mentha aquatica.
N° Constituents Ri lit RI a RI p %a identification
1 -Pinene 932a 931 1026 2.2 RI, MS, 13C NMR
2 Camphene 948a 945 1071 2.4 13
RI, MS, C NMR
3 Sabinene 965a 966 1124 0.9 RI, MS, 13C NMR
4 -Pinene 970b 971 1114 1.6 RI, MS, 13C NMR
5 Myrcene 983a 981 1163 0.9 RI, MS, 13C NMR
6 p-Cymene 1015a 1012 1273 0.3 RI, MS, 13C NMR
7 Limonene 1022a 1021 1205 5.3* RI, MS, 13C NMR
8 1.8-Cineole 1017a 1021 1213 5.9* RI, MS, 13C NMR
9 (Z)--Ocimene 1026b 1025 1235 0.7 RI, 13
C NMR
10 -Terpinene 1053a 1049 1247 0.3 RI, 13
C NMR
11 trans-Sabinene hydrate 1059c 1053 1461 0.2 RI, 13
C NMR
12 Linalool 1086a 1083 1545 RI, 13
C NMR
.
13 cis-Sabinene hydrate 1091d 1083 1545 RI, 13
C NMR
14 trans-Verbenol 1124e 1128 1677 tr RI, 13
C NMR
15 Menthone 1136f 1134 1466 2.6 RI, MS, 13C NMR
16 Lyratol 1138g 1139 1776 tr RI, 13
C NMR
17 Isomenthone 1146f 1144 1495 1.3 RI, MS, 13C NMR
18 Menthofuran* 1150f 1152 1490 50.7 13
RI, MS, C NMR
19 Neomenthol* 1156f 1152 1599 tr RI, 13
C NMR
20 Borneol* 1164h 1152 1704 3.5 RI, MS, 13C NMR
21 Menthol 1166e 1158 1639 1.7 RI, 13
C NMR
22 Terpinen-4-ol 1170a 1163 1601 0.4 RI, MS, 13C NMR
23 -Terpineol 1177a 1172 1699 0.6 RI, MS, 13C NMR
24 Pulegone 1214b 1215 1649 2.3 RI, MS, 13C NMR
25 Bornyl acetate 1269b 1269 1580 0.5 RI, MS, 13C NMR
13
26 Menthofurolactone 0.3 RI, C NMR
1314/1316i 1315/1317 nd 13
27 epi-Menthofurolactone 0.3 RI, C NMR
28 cis-Jasmone 1378j 1366 1946 0.2 13
RI, MS, C NMR
29 (E)--caryophyllene 1421 k
1420 1596 2.9 RI, 13
C NMR
30 Mintlactone 1449i 1453 2323 1.6 RI, 13
C NMR
31 Germacrene D 1479k 1478 1711 2.0 RI, MS, 13C NMR
32 Isomintlactone 1502i 1487 nd 0.3 RI, 13
C NMR
13
33 Hydroxy-mintlactone # 1514 nd 0.3 RI, C NMR
34 Viridiflorol 1580b 1584 2089 3.5 13
RI, MS, C NMR
35 -Cadinol 1643 b
1639 2234 0.1 RI, 13
C NMR
Total : 97.0
Order of elution and percentages are given on apolar column (BP-1), except for compounds with an asterisk (*), percentage on BP-20; RIlitt: retention indices from literature; RIa,
RIp: retention indices measured on apolar and polar columns, respectively; tr, traces. a: ref [14a], b: ref [14b], c: ref [14c], d: ref [14d], e: ref [14e], f: ref [15a], g: ref [15b], h: ref [15c],
i
: ref [13a], j: ref [15d], k: ref [15e]. #RI not available. 13C NMR (italic): compound identified in a fraction of chromatography.
Essential oil of Mentha aquatica Natural Product Communications Vol. 6 (10) 2011 1481
7
1
1,8-cineole (0.1-11.6%) was in the same range as those of
6 2 oils from Germany, the USA and some samples from Italy
5
4
3 OH
(2.1-11.9%), but less than that in the oils from Croatia and
8
O O O O
Italy (16.2-21.6%). Corsican oils cannot be classified
10
9
among the sesquiterpene-rich oils like those of Croatia,
O O O O
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Natural Product Communications Vol. 6 (10) 2011
Published online (www.naturalproduct.us)
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Natural Product Communications
2011
Volume 6, Number 10
Contents
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