Poster Thailand 09 jadi
Sri Atuna, Nurfina Aznama, Retno Arianingruma, Takaya Yb, Niwa
Masatakeb
Department Chemistry education, Universitas Negeri Yogyakarta,
Sleman, Yogyakarta, 55281
b
Faculty of Pharmacy, Meijo University, Tempaku, Nagoya, Japan
Karangmalang, Depok,
a
METHODE OF
RESEARCH
Sample: milled dried stem bark
Hopea is one the main genus of
Dipterocarpaceae, consisting of
approximately 100 species and
widely distributed in Indonesia
specially in Kalimantan
Extraction by organic solvent : acetone or methanol
EXTRACT
The local name is “ cengal,
merawan hitam or pengarawan”.
The plant ussually can be used
as material building, plywood
etc.
By fractionated (VLC)
Fr A
This family of plant is known to
produce a variety of resveratrol
oligomer
Fr B
Fr C
Fr D
Repeated
Chromatography
elusidasion structure by
Spectroscophy methode
(UV, FT-IR, NMR, MS)
These structures are very
interesting and showed
interesting biological activity,
such as antibacterial, anticancer,
antihepatotoxic, and anti-HIV
Pure compounds S-1, S-2, … etc
Methylation & Acethylation
BIOACTIVE COMPOUNDS
STRUCTURE MOLECULE
DERIVATIVES COMPOUNDS
Isolated compounds from H. odorata (3.8
Kg)
Isolated compounds from H. mengarawan
(5 Kg)
HO
HO
H
O
HO
OH
OH
H
H
O H
OH
H
H
HO
OH
HO
H
OH
OH
H
HO H
HO
OH
H H
H
H H
HO
H
HO
HO
H
H
HO
HO
O
OH
OH
OH
OH
H
H
HO
H
H
H
H
HO
H
HO
Balanocarpol
(300 mg)
Heimiol A
(200 mg)
Vaticanol G
(70 mg)
OH
12a
A2
OH
10a
H
H
A1
vaticanol B
(200 mg)
HO
HO
Hopeaphenol (1500 mg)
4a
A1
H
OH
7b
HO
7a
1a
B2
O
12b
4a
14b
12a
O
7a
OH
7b
4b HO
OH
Ampelopsin H (250 mg)
4c OH
B2
B1
OH
OH
H
H
H
10a
OH
OH
H
HO
12b
8a
A2
H H
8b
H
1a
H
8a
HO
O
Balanocarpol
(300 mg)
OH
O H
1b
H
OH
HO
HO
OH
OH
OH
4b
B1
O H
H
H
OH
OH
OH
HO
HO
H O
HO
H
O
H
HO
H
H H
OH
OH
HO
OH
HO HO
HO
H
HO
OH
Isolated compounds from H. nigra (3.5
Kg)
C1
7c
8b 8c
H
C2
12c
O
OH
D2
H
D1
OH
H
H H
12d
OH
H
OH
8d
7d
H
HO
HO
4d
OH
Hemlesyanol C (120 mg)
HO H
HO
OH
H
HO
vaticanol G (200 mg)
Methode identification structure by modern
spectroscophy
OH
HO HO
HO
HO
HH
OH
H
H
HH
OH
HO
H
OH
O
OH
HO
HO
D2
C1
H
HO
O
H
HO
H H
HO
H 7a O
H
Cytotoxicity test by Raji cell lines
Cytotoxicity test by Hela S3 cell lines
Hela S3 cell lines before experiment
Hela S3 cell lines after experiment
Raji cell lines before experiment
experiment
Table 1. The cytotoxic effects of resveratrol oligomers and their
derivatives in human cancer cell lines
No
Sample
Hela- S3
1
2
3
4
5
6
7
8
9
10
11
12
Balanocarpol
Heimiol A
Vaticanol G
Vaticanol B
Hopeaphenol
Ampelopsin H
Hemlesyanol
Deca-methyl-O-hopeaphenol
Deca-acethyl-hopeaphenol
Penta-methyl-O-balanocarpol
Hexa-acethyl-balanocarpol
Doxorobicin (positif control)
Spectrum 1H-1H COSY NMR of vaticanol B
692.78
> 1000
> 1000
92.81
> 1000
129.71
557.44
> 1000
> 1000
> 1000
594,29
96,87
LC50 µg/mL
Raji
235.29
> 1000
> 1000
34.45
781.49
34.69
292.14
> 1000
> 1000
> 1000
594,29
242,10
Myeloma
197.61
> 1000
> 1000
*
250,15
119.62
756.43
> 1000
> 1000
533.85
298,06
*
Raji cell lines after
Conclusion
In this paper we conclusion that isolated compound from steam bark of H.
mengarawan, H.odorata and H. nigra have cytotoxic effect against Raji, HeLa-S3,
and Myeloma cell lines. Vaticanol B (4) and ampelopsin H (6) give the highest
cytotoxic effect against HeLa-S3 and Raji, while the derivative resveratrol, methyl
and acethyl balanocarpol and hopheaphenol showed not active.
Acknowledgements
This work has been supported by competitive grant (Insentif Riset Dasar, Ristek2008), Ministry Reseach and Technology, Republic of Indonesia. The authors are
grateful to the experimental Garden in Carita, Pandeglang, Banten, Indonesia and
Herbarium Bogoriensis for supported the sample and identification of the plant
specimen.
*Note : not finished yet
e-mail : [email protected]
B2
O
C2
H
HO
Spectrum 1H and 13C NMR of vaticanol B
H
8a
A1
Spectrum UV and IR of Vaticanol B
7d
8d
7b
A2
D1
H
B1
HO
OH
OH
OH
Masatakeb
Department Chemistry education, Universitas Negeri Yogyakarta,
Sleman, Yogyakarta, 55281
b
Faculty of Pharmacy, Meijo University, Tempaku, Nagoya, Japan
Karangmalang, Depok,
a
METHODE OF
RESEARCH
Sample: milled dried stem bark
Hopea is one the main genus of
Dipterocarpaceae, consisting of
approximately 100 species and
widely distributed in Indonesia
specially in Kalimantan
Extraction by organic solvent : acetone or methanol
EXTRACT
The local name is “ cengal,
merawan hitam or pengarawan”.
The plant ussually can be used
as material building, plywood
etc.
By fractionated (VLC)
Fr A
This family of plant is known to
produce a variety of resveratrol
oligomer
Fr B
Fr C
Fr D
Repeated
Chromatography
elusidasion structure by
Spectroscophy methode
(UV, FT-IR, NMR, MS)
These structures are very
interesting and showed
interesting biological activity,
such as antibacterial, anticancer,
antihepatotoxic, and anti-HIV
Pure compounds S-1, S-2, … etc
Methylation & Acethylation
BIOACTIVE COMPOUNDS
STRUCTURE MOLECULE
DERIVATIVES COMPOUNDS
Isolated compounds from H. odorata (3.8
Kg)
Isolated compounds from H. mengarawan
(5 Kg)
HO
HO
H
O
HO
OH
OH
H
H
O H
OH
H
H
HO
OH
HO
H
OH
OH
H
HO H
HO
OH
H H
H
H H
HO
H
HO
HO
H
H
HO
HO
O
OH
OH
OH
OH
H
H
HO
H
H
H
H
HO
H
HO
Balanocarpol
(300 mg)
Heimiol A
(200 mg)
Vaticanol G
(70 mg)
OH
12a
A2
OH
10a
H
H
A1
vaticanol B
(200 mg)
HO
HO
Hopeaphenol (1500 mg)
4a
A1
H
OH
7b
HO
7a
1a
B2
O
12b
4a
14b
12a
O
7a
OH
7b
4b HO
OH
Ampelopsin H (250 mg)
4c OH
B2
B1
OH
OH
H
H
H
10a
OH
OH
H
HO
12b
8a
A2
H H
8b
H
1a
H
8a
HO
O
Balanocarpol
(300 mg)
OH
O H
1b
H
OH
HO
HO
OH
OH
OH
4b
B1
O H
H
H
OH
OH
OH
HO
HO
H O
HO
H
O
H
HO
H
H H
OH
OH
HO
OH
HO HO
HO
H
HO
OH
Isolated compounds from H. nigra (3.5
Kg)
C1
7c
8b 8c
H
C2
12c
O
OH
D2
H
D1
OH
H
H H
12d
OH
H
OH
8d
7d
H
HO
HO
4d
OH
Hemlesyanol C (120 mg)
HO H
HO
OH
H
HO
vaticanol G (200 mg)
Methode identification structure by modern
spectroscophy
OH
HO HO
HO
HO
HH
OH
H
H
HH
OH
HO
H
OH
O
OH
HO
HO
D2
C1
H
HO
O
H
HO
H H
HO
H 7a O
H
Cytotoxicity test by Raji cell lines
Cytotoxicity test by Hela S3 cell lines
Hela S3 cell lines before experiment
Hela S3 cell lines after experiment
Raji cell lines before experiment
experiment
Table 1. The cytotoxic effects of resveratrol oligomers and their
derivatives in human cancer cell lines
No
Sample
Hela- S3
1
2
3
4
5
6
7
8
9
10
11
12
Balanocarpol
Heimiol A
Vaticanol G
Vaticanol B
Hopeaphenol
Ampelopsin H
Hemlesyanol
Deca-methyl-O-hopeaphenol
Deca-acethyl-hopeaphenol
Penta-methyl-O-balanocarpol
Hexa-acethyl-balanocarpol
Doxorobicin (positif control)
Spectrum 1H-1H COSY NMR of vaticanol B
692.78
> 1000
> 1000
92.81
> 1000
129.71
557.44
> 1000
> 1000
> 1000
594,29
96,87
LC50 µg/mL
Raji
235.29
> 1000
> 1000
34.45
781.49
34.69
292.14
> 1000
> 1000
> 1000
594,29
242,10
Myeloma
197.61
> 1000
> 1000
*
250,15
119.62
756.43
> 1000
> 1000
533.85
298,06
*
Raji cell lines after
Conclusion
In this paper we conclusion that isolated compound from steam bark of H.
mengarawan, H.odorata and H. nigra have cytotoxic effect against Raji, HeLa-S3,
and Myeloma cell lines. Vaticanol B (4) and ampelopsin H (6) give the highest
cytotoxic effect against HeLa-S3 and Raji, while the derivative resveratrol, methyl
and acethyl balanocarpol and hopheaphenol showed not active.
Acknowledgements
This work has been supported by competitive grant (Insentif Riset Dasar, Ristek2008), Ministry Reseach and Technology, Republic of Indonesia. The authors are
grateful to the experimental Garden in Carita, Pandeglang, Banten, Indonesia and
Herbarium Bogoriensis for supported the sample and identification of the plant
specimen.
*Note : not finished yet
e-mail : [email protected]
B2
O
C2
H
HO
Spectrum 1H and 13C NMR of vaticanol B
H
8a
A1
Spectrum UV and IR of Vaticanol B
7d
8d
7b
A2
D1
H
B1
HO
OH
OH
OH