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Chemical Composition of Essentia

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					                  Chemical Composition of Essential Oils from the Rhizomes of

                           Hedychium ellipticum and Etlingera littoralis

                  Sineenard Songsri, Iyared Kumrit and Nuchnipa Nuntawong



    Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai , Thailand,



ABSTRACT
       Essential oils isolated by hydrodistillation from the rhizomes of Hedychium ellipticum
and Etlingera littoralis were analyzed by GC/MS. Forty-seven and seventeen components
representing 52.22 % and 21.11 % of the total oil of H. ellipticum and E. littoralis were
respectively identified. A single major component of H. ellipticum rhizome oil was 1,8-cineol
(83.90%) while spathulenol (34.79%), 1,8-cineol (19.57%), n-hexadecanoic acid (8.51%) and
α-terpineol (4.73%) were the major components of rhizome oil of E. littoralis.


Keywords: Zingiberaceae, Hedychium ellipticum, Etlingera littoralis, Essential oil composition


INTRODUCTION
       Zingiberaceae or a Ginger family is a family of flowering plants consisting of aromatic
perennial herbs with creeping horizontal or tuberous rhizome. It is a large family comprising of more
than 200 species. The large general found in Thailand are Curcuma, Hedychium, Zingiber, Alpinia,
Kaempferia and Etlingera(1). They are important natural resources that provide many useful products
for food, spices, medicines, dyes, perfume and aesthetics to man. Rhizome of ginger plants are eaten
raw or cooked as vegetables, used for flavoring food and in traditional forms of medicine to treat a
variety of diseases, for example, in Peninsular Malaysia decoction of the boiled leaves of difference
Hedychiuym species is eaten for indigestion. In Moluccas and the Philippines, the juice of the chewed
stem is applied to swellings(2). The rhizome of Etlingera punicea is used as spice and ingredient in
noodle and curry in Thailand(3). The essential oils from several Hedychium species; H. venustum, H.
spicatum, H. coronarium and H. flavescens have been reported to possess significant antibacterial
acivities. Monoterpenes, 1,8-cineole was the major component present in the rhizome oils of H.
venustum, H. spicatum and H. coronarium, while β-pinene was the major constituent in the oil of H.
flavescens(4). 1,8-cineole, sabinene and terpen-4-ol were the major constituents of rhizome oils of H.
ellipticum(5). The leaves, stems, flowers and rhizomes essential oils of Etlingera elatior were
investigated. β-pinene, caryophyllene and (E)-β-farnesene were reported to be the major components
in the leaves(6), 1,1-dodecanediol diacetate, (E)-5-dodecane and cyclododecane were rich in the stems,
flowers and rhizomes(7). Methyleugenol and methylisoeugenol are prominent in the oils obtained from
the rhizomes of Etlingera cevuga. To our knowledge, there are no previous reports on the chemical
composition of the volatile oils of E. littoralis in the literature. The present study is therefore aimed to
investigate the essential oils constituents of the rhizomes of H. ellipticum and E. littoralis with respect
to seeking major components by GC/MS.



MATERIALS AND METHODS

       Plant Materials: Hedychium ellipticum and Etlingera littoralis used in this study were
collected from Chiang Mai province in January 2007. The samples were identified by J. F. Maxwell of
the CMU Herbarium, where a voucher specimen was deposited (06-609 and 06-367 J.F. Maxwell).

       Isolation of oils: Dried rhizomes of H. ellipticum (50.47 g) and E. littolaris (50.35 g) were
hydrodistilled in Clevenger-type apparatus for 4 h to obtained the corresponding rhizome oils. The
yields were 52.22 % and 21.11 % for H. ellipticum and E. littolaris, respectively.

        Essential Oil analysis: The essential oils were analyzed using Agilent-HP 5973 Mass
Spectrometer equipped with Alltech 15897 AT-1 MS capillary column (30 m x 0.25 mm, 0.25 µm
film thickness). The oven temperature was programmed from 45-250 oC at the rate of 2 oC/min with
final hold 12.5 min, using helium gas as a carrier gas. Individual components were identified by Wiley
275 and NIST database matching. Relative percentage of individual components were calculated
based on GC peak areas without using correction factors. The injector and detector temperatures were
200 oC and 230 oC, respectively. MS were taken at 70 eV with mass range of m/z 29-550.

RESULTS AND DISCUSSION
       Essential oils isolated by hydrodistillation from the rhizomes of H. ellipticum and E. littolaris
were analyzed by GC/MS. Chemical compositions of the rhizome oils of H. ellipticum and E.
littolaris are summarized in Table I. Forty-seven components representing 52.22 % of the total oil
were identified in H. ellipticum essential oil. The only main constituent of the oil was 1,8-cineol
(83.90%) and the other components were terpinen-4-ol (1.37%) α-terpineol (1.26%) and β-Pinene
(1.20%). The chemical compositions of the rhizome oils of H. ellipticum under present study were
different from previous report in India(8). 1,8-cineole (33.0%), sabinene (22.2%), and terpin-4-ol
(14.3%) being major constituents, while in our study, only 1,8-cineole was a principal component.
Terpinen-4-ol was found only a small amount wheras sabinene was not even determined in the oils of
present work. However, 1,8-Cineole remained the major constituent in the oils of several Hedychium
species, such as H. acuminatum (76.0%), H. venustum (45.4%), H. spicatum (44.3%), H. coronarium
(48.7%) and H. gardnerianum (27.0%) (4, 9, 10).
       Nineteen components were identified in the essential oil of E. littolaris which made up
21.11% of total content. The major components were spathulenol (33.79%), 1,8-cineol (19.57%),
n-hexadecanoic acid (8.51%) and α-terpineol (4.73%). All of these components are reported from the
essential oil of E. littolaris for the first time. The compositions of oils of E. littoralis quite differed
from the oils investigated from previous report in some Etlingera species. Methyleugenol (47.4%) and
methylisoeugenol (18.4%) are major constituents of the rhizomes essential oils of E. cevuga(7), while
methyl chavicol was the major component of the essential oil E. punicea(3). The essential oils of the
flowers and rhizomes of E. elatior contained 1,1-dodecanediol diacetate (24.38% and 40.37%,
respectively) and cyclododecane (47.28% and 34.45% respectively)(6).



Conclusion

       The oils from the rhizomes of H. ellipticum and E. littolaris consisted mainly of monoterpenes
and sesquiterpene hydrocarbons as well as oxygenated monoterpenes and sesquiterpenes. The high
percetage of 1,8-cineol in the rhizome oils of H. ellipticum may be used as an indicator of the Genus.
To the best of our knowledge, this is the first report for the chemical compositions of the rhizome oils
of E. littolaris and may be used as foundation for further chemotaxonomic studies on the genus.



        Table 1 Chemical composition of the essential oils from H. ellipticum and E. littoralis
                                                                                   Content (%)
          Compounds
                                                                   MW      H. ellipticum   E. littolaris
          Origanene                                               136.13       0.11               -
          α-Pinene                                                136.13       0.83              0.91
          Camphene                                                136.13       0.11              0.56
          2,4(10)-Thujadiene                                      134.11       0.06               -
          β-Pinene                                                136.14       1.20               -
          1,8-Cineole                                             154.14      83.90           19.57
          γ-Terpinene                                             136.13       0.20               -
          cis-Linalool oxide                                      170.13       0.21               -
          L-Fenchone                                              152.12       0.05               -
          α-Terpinolene                                           136.13       0.07               -
          β-Linalool                                              154.14       0.27              0.85
          Thujone                                                 152.12       0.12              1.72
          Fenchol, exo-                                           154.14       0.14               -
          2-Cyclohexen-1-ol                                       154.14       0.07               -
          (1S)-Camphor                                            152.12       0.22               -
          Pinocarveol                                             152.12       0.55              1.75
          Sabina ketone                                           138.10       0.21               -
          Bicyclo[2.2.1]heptan-3-one, 6,6-dimethyl-2-methylene-   150.10       0.06               -
          Borneol                                                 154.14       0.14               -
          Terpinen-4-ol                                           154.14       1.37              2.51
          thymol                                                  150.10       0.75               -
         Table 1 Continued
                                                                          Content (%)
         Compounds
                                                        MW      H. ellipticum     E. littolaris
         α-terpineol (p-menth-1-en-8-ol)               154.14       1.26                4.73
         α-Pinene-10-ol                                152.12       0.64                 -
         trans-Carveol                                 152.12       0.17                0.37
         propanal, 2-methyl-3-phenyl-                  148.09       0.14                0.76
         carvone                                       150.10       0.10                 -
         2-Octen-1-ol, 3,7-dimethyl-                   156.15       0.06                0.41
         Piperitone                                    152.12       0.02                 -
         Carvenone                                     152.12       0.03                0.87
         Perillyl aldehyde                             150.10       0.04                0.16
         2-Caren-10-al                                 150.10       0.03                 -
         Cumyl alcohol                                 150.10       0.10                 -
         Perillic alcohol                              152.12       0.13                0.58
         Isothymol                                     150.10       0.17                 -
         1,4-p-Menthadien-7-ol                         152.12       0.04                 -
         Dihydro-.gamma.-ionone                        194.17       0.03                 -
         Methyl eugenol ether                          178.10       0.02                 -
         Cyperene                                      204.19         -                 2.14
         Dihydro-.alpha.-ionone                        205.19       0.03                 -
         allo-Aromadendrene                            206.19       0.04                 -
         α-Guaiene                                     207.19       0.03                1.35
         γ-Maaliene                                    208.19       0.03                0.33
         Spathulenol                                   209.19       0.33             34.79
         Ledol                                         210.19       0.07                2.06
         Germacrene B                                  211.19       0.56                 -
         Cadalin                                       212.19       0.08                 -
         2-Dodecanone                                  213.19       0.18                0.60
         n-Hexadecanoic acid                           214.19       0.04                8.51



ACKNOWLEDGEMENTS
       The financial supports from the Center of Excellence for Innovation in Chemistry (PERCH-
CIC) and the Graduate School Chiang Mai University are gratefully acknowledged.



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