Sri Atun
a, Nurfina Aznam
a, Retno Arianingrum
a, Takaya Y
b, Niwa
Masatake
ba
Department Chemistry education, Universitas Negeri Yogyakarta, Karangmalang, Depok,
Sleman, Yogyakarta, 55281
b
Faculty of Pharmacy, Meijo University, Tempaku, Nagoya, Japan
Hopea is one the main genus of Dipterocarpaceae, consisting of approximately 100 species and widely distributed in Indonesia specially in Kalimantan
The local name is “ cengal,
merawan hitam or pengarawan”. The plant ussually can be used as material building, plywood etc.
This family of plant is known to produce a variety of resveratrol oligomer
These structures are very interesting and showed
interesting biological activity,
such as antibacterial, anticancer, antihepatotoxic, and anti-HIV
METHODE OF
RESEARCH
Sample: milled dried stem bark
Extraction by organic solvent : acetone or methanol
EXTRACT
By fractionated (VLC)
Fr A Fr B Fr C Fr D
Pure compounds S-1, S-2, … etc
Repeated
Chromatography elusidasion structure by Spectroscophy methode (UV, FT-IR, NMR, MS)
BIOACTIVE COMPOUNDS
Methylation & Acethylation
STRUCTURE MOLECULE
DERIVATIVES COMPOUNDS
Isolated compounds from
H. mengarawan
(5 Kg)
O
OH H H HO
OH HO
OH
OH H
H
O HO
OH
OH
OH
HO OH
H
H H
H
HO
HO
HO
HO OH
OH OH HO
HO
H H H H H
H
O O
HO HO
HO HO
HO HO
OH
OH
OH H
H H H H
HH H
OH
Balanocarpol (300 mg)
Heimiol A (200 mg)
Vaticanol G (70 mg)
vaticanol B (200 mg)
Isolated compounds from
H. odorata
(3.8
Kg)
O
OH H H HO
OH HO
OH
OH H
H
Balanocarpol (300 mg)
O HO
HO
HO
OH OH
H H
H
O
OH OH
HO HO
HO
H H
H
H H
Hopeaphenol (1500 mg)
O
O
HO HO
OH
H H
OH OH H
H HO
HO OH
OH
OH H
H
H H
A1 A2
B1
B2 1a
4a
7a 8a 10a
12a 7b
8b 1b 4b
12b 14b
Ampelopsin H (250 mg)
O O
H H HO
OH
HO
OH
OH H H
H
H H
H
OH HO
OH OH
OH
A1
A2
B2
B1
C1
C2
D1 D2 1a
4a
7a 8a 10a 12a
7b 8b
4b 12b
7c 8c
12c
7d 8d
4d 12d 4c
Hemlesyanol C (120 mg)
Isolated compounds from
H. nigra
(3.5
Kg)
HO
HO HO
HO OH
OH OH HO
HO
H H
H H H H
vaticanol G (200 mg)
Spectrum UV and IR of Vaticanol B
O O
HO HO
HO
HO HOHO
OH OH
OH
H H
H H HH
H H
OH
Spectrum 1H and 13C NMR of vaticanol B
O
O
HO HO
HO
HO HO
HO
OH
OH
OH
H H
H H
H H
H H
OH
D1 D2
A1 A2 B1
B2 C1
C2
7a 8a
7d 8d
7b
Spectrum 1H-1H COSY NMR of vaticanol B
Methode identification structure by modern
spectroscophy
Cytotoxicity test by
Hela S3 cell lines
Hela S3 cell lines before experiment
Hela S3 cell lines after experiment
Cytotoxicity test by
Raji cell lines
Raji cell lines before experiment Raji cell lines after experiment
No Sample LC50 µg/mL
Hela- S3 Raji Myeloma
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
235.29 > 1000 > 1000 34.45 781.49
34.69 292.14 > 1000 > 1000 > 1000 594,29 242,10
197.61 > 1000 > 1000
* 250,15 119.62 756.43 > 1000 > 1000 533.85 298,06
*
Table 1. The cytotoxic effects of resveratrol oligomers and their
derivatives in human cancer cell lines
*Note : not finished yet
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.
