GC-MS and NMR Analysis of ethyl-p-methoxycinnamte Isolated from Kaempferia galanga L Using Distillation Method
ｾ＠ ｾ｡Ｍ
ｳｾＧ
\.,
I
Basic Science International Conference
PROCEEDINGS
2 nd BASIC SC I ENCE
International Co
Malang
th
February 24-25 , 201
2
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 t he
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 ethylpmethoxycinnamate
--%) [2J.
Recently a lot of research established to led
_ ...li lization of the main components of K. galanga
,u ·h as ethylpmethoxycinnamate. Ethyl p_ oxycinnamate eQuId inhibit the proliferation of
_
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
ｾＮ＠
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 95105 "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 280°C; ion source
temperature 280°C; inject volume I!tl; column
Assaat, L. D., T. T. Irawadi. I. Batubara
temperature 60°C240°C. The spectra were recorded
and compared with the terpene library.
Compound were identified by 'HNMR,
COSY, HMQC, and HMBC. Methanold3 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. GCMS spectra showed that white crystal
is a pure compound (Fig I).
Basic Science International Conference 2012
Table. I. The result of ' HNMR spectrum analysis
;\0
Carbon
2
Chemical
sh ifts
(0 . ppm)
Coupling
Integration Multiplicity constant
IJ, Hz)
63176
7.5 87 1
Duple!
Duplet
16.5
7.1 908
69015
Duplet
Duplet
6. 9
6.9
3.7861
4.1898
l.280 i
Singlet
QU311et
Triplet
5.9
6.S
7
10
II
ｉｾ＠
Below is a figure of a complete analytical result
analysis of ethylpmethoxycinnamate.
Fig. 2. The result of 'HNMR, COSY, HMQC. all
HMBC
IV.CONCLUSION
Fig. I. The spectra for K galanga L essential oil (upper)
and white crystal (down).
GCMS spectra sl10wed that main compound
c. ent ial oi l were cthylpmethoxycinnamate, ethyl
ﾷ ｬｏｮ｡ｭｾ
ｷ Ｎ＠ and 6cnrcne (upper). Chromatogram
fr m \\hite crystals spectra showed at retention
:10 3 . min. CiC'vlS :E I;mlz :206 (MI) (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 'HNMR, COSY,
HMQC, and HMBC. White crystals: 'HNMR
0:6.3176 (I H, d, J= 16.5Hz H2), 0: (I H, d, J= 16.5 Hz
H3) , 0:7.4908 (2H., d, J=6.9Hz H5 , H9), 6:6.9045
(2H, d, J=6.9Hz H6, H8), 0:3.7861 (3H, s, HIO),
0:4.1898 (2H, k, HII), 0:1.2807 (3H, t, H12). 13C _
NMR 0:167 .74 (CI), 0:114.97 (C2), 0:144.56 (C3), 0:127.01 (C4), 0:129.59 (C5), 0:114.08 (C6),
0:161.79 (C7), 0:114.08 (C8), 0:129.59 (C9),
0:54.52 (CI 0),0:60.12 (CII), 0: 13 .30 (C12).
Overall analysis is summarized in the following
table:
Ｑ＠ ｾ＠ ＶＮ＠
-I
Ethylpmethoxycinnamate compound
isolated from K. galunga L (2 .distillation method. The result of GC I
showed that the white crystals obtai _
distillation is ethylpmethoxyeinnamate ＧＭＺＡ［ ｾＺｬ｡ｯ＠
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/.
ｾ＠ I ' 506.
Basic Science International Conference 2012
[3] Lill B , Liu F , Chen C, Gao H. Supercritical carbon
dioxide extraction of ethyl pmethoxycinnamate from
Kaell1p{eria galanga L. rhi zome and its apoptotic
induction in human HepG2 cells. 2010. Natura/
Product Research. Vol. 24, No. 20 , 15 December
ｾ＠ ＹＳＲＮ＠
2010: ＱＹＲＷＭ
ｳｾＧ
\.,
I
Basic Science International Conference
PROCEEDINGS
2 nd BASIC SC I ENCE
International Co
Malang
th
February 24-25 , 201
2
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 t he
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 ethylpmethoxycinnamate
--%) [2J.
Recently a lot of research established to led
_ ...li lization of the main components of K. galanga
,u ·h as ethylpmethoxycinnamate. Ethyl p_ oxycinnamate eQuId inhibit the proliferation of
_
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
ｾＮ＠
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 95105 "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 280°C; ion source
temperature 280°C; inject volume I!tl; column
Assaat, L. D., T. T. Irawadi. I. Batubara
temperature 60°C240°C. The spectra were recorded
and compared with the terpene library.
Compound were identified by 'HNMR,
COSY, HMQC, and HMBC. Methanold3 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. GCMS spectra showed that white crystal
is a pure compound (Fig I).
Basic Science International Conference 2012
Table. I. The result of ' HNMR spectrum analysis
;\0
Carbon
2
Chemical
sh ifts
(0 . ppm)
Coupling
Integration Multiplicity constant
IJ, Hz)
63176
7.5 87 1
Duple!
Duplet
16.5
7.1 908
69015
Duplet
Duplet
6. 9
6.9
3.7861
4.1898
l.280 i
Singlet
QU311et
Triplet
5.9
6.S
7
10
II
ｉｾ＠
Below is a figure of a complete analytical result
analysis of ethylpmethoxycinnamate.
Fig. 2. The result of 'HNMR, COSY, HMQC. all
HMBC
IV.CONCLUSION
Fig. I. The spectra for K galanga L essential oil (upper)
and white crystal (down).
GCMS spectra sl10wed that main compound
c. ent ial oi l were cthylpmethoxycinnamate, ethyl
ﾷ ｬｏｮ｡ｭｾ
ｷ Ｎ＠ and 6cnrcne (upper). Chromatogram
fr m \\hite crystals spectra showed at retention
:10 3 . min. CiC'vlS :E I;mlz :206 (MI) (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 'HNMR, COSY,
HMQC, and HMBC. White crystals: 'HNMR
0:6.3176 (I H, d, J= 16.5Hz H2), 0: (I H, d, J= 16.5 Hz
H3) , 0:7.4908 (2H., d, J=6.9Hz H5 , H9), 6:6.9045
(2H, d, J=6.9Hz H6, H8), 0:3.7861 (3H, s, HIO),
0:4.1898 (2H, k, HII), 0:1.2807 (3H, t, H12). 13C _
NMR 0:167 .74 (CI), 0:114.97 (C2), 0:144.56 (C3), 0:127.01 (C4), 0:129.59 (C5), 0:114.08 (C6),
0:161.79 (C7), 0:114.08 (C8), 0:129.59 (C9),
0:54.52 (CI 0),0:60.12 (CII), 0: 13 .30 (C12).
Overall analysis is summarized in the following
table:
Ｑ＠ ｾ＠ ＶＮ＠
-I
Ethylpmethoxycinnamate compound
isolated from K. galunga L (2 .distillation method. The result of GC I
showed that the white crystals obtai _
distillation is ethylpmethoxyeinnamate ＧＭＺＡ［ ｾＺｬ｡ｯ＠
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/.
ｾ＠ I ' 506.
Basic Science International Conference 2012
[3] Lill B , Liu F , Chen C, Gao H. Supercritical carbon
dioxide extraction of ethyl pmethoxycinnamate from
Kaell1p{eria galanga L. rhi zome and its apoptotic
induction in human HepG2 cells. 2010. Natura/
Product Research. Vol. 24, No. 20 , 15 December
ｾ＠ ＹＳＲＮ＠
2010: ＱＹＲＷＭ