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Basic Science International Conference

PROCEEDINGS
2 nd BASIC SC I ENCE
International Co
Malang
th
February 24-25 , 201

nd

Basic Science International Conference 2012

th
February 24 - 25 ,2012

Proceedings

RESEARCH INNOVATION ON MODELlN6 , SIMULATION ,

AND ITS APPLICATIONS

Editors
Dr. Wuryansari Muharini Kusumawinahyu

Danny Prasetyo Hartanto

Rizka Firdausi

Mutya Fani Atsomya

Mathematics Department on Behalf of Faculty of Sciences

Brawijaya University

Basic Science International Conference 2012

L. D., T. T. Irawadi, I. Batuhara

GC-MS and NMR Analysis of ethyl-p-methoxycinnamate

I olated From Kaemp/eria ga/anga L Using Distillation Method

. Lusiani Dewi Assaat' *, Tun Tedja Ira wadi 2, Irmanida Batubara 3

Faculty a/Mathematics and Natural Sciences Education. Sultan Ageng Tirtayasa University. Serang.
Indonesia. ussaal@Fuhoo.cull1
p Irtmenf o/Chemistry, Faculty o/Mathematics and Nalllral Sciences , Bogor Agriculture Uni versity,
Indon esia, 11111 ledja @wd1Ou. CUI1l
partment 0/ Chemistry, Faculty 0/ Mathematics and Natllral Sciences, Bogor Agriculture University,
Indon esia, imeba Illba ra(al gl1lu il.com

Abstract
' poses of this research were to isolate and analyze ethyl-p-methoxycinnamate which is the main
lit 0/ Kaemp/eria g alangu L. Volatile oil 0/ K. ga/anga L obtained by distilled fresh rhizome using
' tillation method. The main components of K. galanga L volatile oil were ethy l-p-methoxycinnamate,
1/ Jmate, and o-3-carel/c. The ethy l-p-methmJ'cinnamate compound analyzed using gas chromatography
't!clrometry (GC-MS) alld nuclear magnetic resonance (NMR). The result 0/ GC-MS analysis showed
-p -methoxycinllamatc is the main component in the volatile oil (26.4%). Th e structure then conJirmed
- ' vIR, COSY, HMQC, and HMBC analysis in NMR .
. . -p-lIIelh oxycinnamate. GC-MS. NMR
.u DlJCTlON

Kencur (Kael7Jl2/eria galOl?ya L) is one of the

mes commonly used by people of Indonesia to

_ I swelling, rheumatism , cough , abdominal pain,

'""'?\: torant, bacterial' infection, and used as

ients for preparing' Jamu' , a local health tonic

The main components of kencur volatile oils are

(1.28%), camphene (2.47%), carvone
' o,IQ ) , benzene (1.33%), eucalyptol (9.59%),
col (2.87%), methyl cinnamate (23.23%),
Mcane (6.41%) and ethyl-p-methoxycinnamate

--%) [2J.

Recently a lot of research established to led

_ ...li lization of the main components of K. galanga
,u h as ethyl-p-methoxycinnamate. Ethyl p
_ oxycinnamate eQuId inhibit the proliferation of
_-<J2 cells in a dose-dependent manner by
~: i ng cells to enter into apoptosis. Therefore, it is
rlant to choose the method how to isolate ethylfrom
K.
galanga
L.
_lh oxyci nnamate
- rc ritical CO 2 extraction method was used to
; ethyl p-methoxycinnamate with yield about

_ :

[3 ].

[n this study, the distillation method used to

eth yl p-methoxycinnamate. By using this
_ od on K. galanga L rhizome, essential oil from
~i.JI(/nga L will be obtained which is expected to

in eth yl p-methoxycinnamate with the highest

_ 1. On other hand, distillation method is a simple
because it is only use water as a solvent,
::ad of the other chemical solvents. By using the
_ :r solvent is expected that isolated compound
_I>

have a high 1 \ 1 f,.;at;

medicine.
II. MATERIAL ;\"\D l ETH D_
Plant materiab

Tht:: 1.0- 1.: y 3L

wcre collected from pa ar md
rhizome determined b; Herbanur"
Biology research cenrer Ll PI. Bogor. lnel n

_I ~.

Preparation of K. gaiallga L distillate

About 500 g K. galanga L rhizome washed

und cut into small pieces. The rhizomes were
distillated for 4 hours. During the process, solvent
temperature is set at 95-105 "e.
Water favor will carry the components of
volatile oil, then the essential oil is collected. From
the essential oil and residue, we can collect a white
crystals after left over night. This white chrystals
collected in the bottles for further analysis.

Identification of compound

The chemical components of wh ite crystals

was determined by Agilent Technologies 6890 Gas
Chromatograph with Auto Sampler and 5973 1as.

Selective Detector and Chemstation data sy rem.Th e

operating parameters were as follows:Column: HP 5
WAX. Ionization mode EI; electron energy 70 eV;
Capillary Column 30 m x 0.25 mm x 0.25 !-tm Film
Thickness; interface temperature 280C; ion source
temperature 280C; inject volume I!-tl; column

Assaat, L. D., T. T. Irawadi. I. Batubara

temperature 60C-240C. The spectra were recorded

and compared with the terpene library.
Compound were identified by 'H-NMR,
COSY, HMQC, and HMBC. Methanol-d3 was used
as the NMR solvent. These NMR measurements was
performed by using JEOL EC600NMR.

III. RESULT AND DISCUSSION

Disti lation process of K. galangal rhizome
resulted K. galanga L essential oil. [n cold
conditions, a white crystal formed in the essential
oil. Its yield of white crystal is about 0.28%. the
white crystals were collected in a vial for further
analysis. GC-MS spectra showed that white crystal
is a pure compound (Fig I).

Basic Science International Conference 2012

Table. I. The result of ' H-NMR spectrum analysis

;\0

Carbon
2

Chemical
sh ifts
(0 .ppm)

Integration

Coupling
Multiplicity constant
IJ, Hz)

63176
7.5 87 1

Duple!
Duplet

16.5

7.-1 908
690-15

Duplet
Duplet

6. 9
6.9

3.7861
4.1898
l.280 i

Singlet
QU311et
Triplet

1 6. ~

-I

5.9
6.S
7
10
II
I~

Below is a figure of a complete analytical result

analysis of ethyl-p-methoxycinnamate.

Fig. 2. The result of 'H-NMR, COSY, HMQC.

all

HMBC

IV.CONCLUSION

Fig. I. The spectra for K galanga L essential oil (upper)

and white crystal (down).

GC-MS spectra sl10wed that main compound

c.- ent ial oi l were cthyl-p-methoxycinnamate, ethyl
lOnam~w . and 6-cnrcne (upper). Chromatogram
fr m \\hite crystals spectra showed at retention
:10 3 .
min. CiC-'vlS :E I;mlz :206 (M-I) (down) .
R ult f mass spectrulll analysis compared with
Ii rar;, inde.\ mass spectrum. Therefore, the analysis
\\"as continucd using Nuclear Magnetic Resonance
(NMR).
White crystals analyzed using 'H-NMR, COSY,
HMQC, and HMBC. White crystals: 'H-NMR
0:6.3176 (I H, d, J= 16.5Hz H-2), 0: (I H, d, J= 16.5 Hz
H-3) , 0:7.4908 (2H., d, J=6.9Hz H-5 , H-9), 6:6.9045
(2H, d, J=6.9Hz H-6, H-8), 0:3.7861 (3H, s, H-IO),
0:4.1898 (2H, k, H-II), 0:1.2807 (3H, t, H-12). 13C _
NMR 0:167 .74 (C-I), 0:114.97 (C-2), 0:144.56 (C
3), 0:127.01 (C-4), 0:129.59 (C-5), 0:114.08 (C-6),
0:161.79 (C-7), 0:114.08 (C-8), 0:129.59 (C-9),
0:54.52 (C-I 0),0:60.12 (C-II), 0: 13 .30 (C-12).
Overall analysis is summarized in the following
table:

Ethyl-p-methoxycinnamate compound
isolated from K. galunga L (2 .
distillation method. The result of GC- I
showed that the white crystals obtai _
distillation is ethyl-p-methoxyeinnamate - '-::!;~::lao
ACKNOWLEDGEME:\T
We gratefully acknowledge the fun d =
Directorate General of Higher Edueat
of Indonesia for BPPS program and .
Mitsunaga and Kosei Yamauchi lor
spectroscopic analysis at Gifu Uni\'ers
REFERENCES
[1) Tara S, Chandra kala S, Sachidananda
Smita S, Ganesh S. Wound healing :J.C
alcoholic extract of Ka empferia galallga
rats . 2006. [ndioll J Physinl Plwl'//1L/ cv l 20'
3ti4-J90.

L. D., T. T. Irawadi, I. Batubara

s, Yuenyongsawad S, Kummee S,
jarllwan S. Chemical components and
19ical activities of volatile oil of Kaemp/eria
.III Linn. 2005. Songk/anakarin J. Sci. Techno/.
~ I ' -506.

Basic Science International Conference 2012

[3] Lill B , Liu F , Chen C, Gao H. Supercritical carbon

dioxide extraction of ethyl p-methoxycinnamate from
Kaell1p{eria galanga L. rhi zome and its apoptotic
induction in human HepG2 cells. 2010. Natura/
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