Sri Atuna, Nurfina Aznama, Retno Arianingruma, Takaya Yb, Niwa Masatakeb

Department Chemistry education, Universitas Negeri Yogyakarta, Karangmalang, Depok, Sleman, Yogyakarta, 55281
b Faculty of Pharmacy, Meijo University, Tempaku, Nagoya, Japan
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)
This family of plant is known to
produce a variety of resveratrol
oligomer
Fr A
Fr B
Fr C
Fr D
Repeated
Chromatography
These structures are very interesting
and showed interesting biological
activity, such as antibacterial,
anticancer, antihepatotoxic, and antiHIV
elusidasion structure by
Spectroscophy methode
(UV, FT-IR, NMR, MS)
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
H
H
OH
HO
H
H
H
HO
H
OH
OH
H
HO H
HO
OH
H H
H
H H
HO
OH
OH
OH
H
HO
H
H
HO
HO
H
H
H
H
HO
HO
H
H
H
HO
Balanocarpol
(300 mg)
Heimiol A
(200 mg)
Vaticanol G
(70 mg)
OH
A2
OH
4a
A1
H
H
7a
1a
H
OH
7b
A2
12a
14b
H
OH
HO
12b
O
7a
12b
OH
4c OH
B2
H
H
H
10a
7b
C1
7c
8b 8c
OH
4b HO
H
OH
H
H H
OH
H
OH
8d
7d
HO H
OH
O
OH
Ampelopsin H (250 mg)
OH
D2
H
C2
12c
HO
HO
12d
OH
B1
O
OH
8a
H H
8b
B2
HO
4a
HO
Hopeaphenol (1500 mg)
HO
1a
H
8a
HO
A1
vaticanol B
(200 mg)
10a
H
12a
O
Balanocarpol
(300 mg)
OH
O H
1b
H
OH
HO
HO
OH
OH
OH
4b
B1
O H
H
HO
O
OH
OH
OH
OH
H
H
HO
H
H H
OH
OH
OH
HO HO
HO
O H
O
HO
HO
H O
HO
H
OH
OH
OH
HO
HO
OH
Isolated compounds from H. nigra (3.5 Kg)
HO
H
D1
4d
OH
Hemlesyanol C (120 mg)
HO
H
vaticanol G (200 mg)
Methode identification structure by modern spectroscophy
OH
HO HO
HO
HH
OH
H
H
HH
HO
OH
HO
H
OH
O
OH
HO
HO
D2
C1
H
HO
O
H
D1
H
B1
H H
HO
H 7a O
H
HO
Spectrum
1H
Hela S3 cell lines after 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)
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
Spectrum 1H-1H COSY NMR of vaticanol B
NMR of vaticanol B
Cytotoxicity test by Raji cell lines
Cytotoxicity test by Hela S3 cell lines
Hela S3 cell lines before experiment
and
13C
Myeloma
197.61
> 1000
> 1000
*
250,15
119.62
756.43
> 1000
> 1000
533.85
298,06
*
Raji cell lines before experiment
C2
H
8a
A1
Raji cell lines after experiment
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, Ristek- 2008), 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 : Atun_1210@yahoo.com
O
H
7b
A2
Spectrum UV and IR of Vaticanol B
7d
8d
HO
HO
OH
B2
OH
OH