Resveratrol derivatif and biological activity
RESVERATROL DERIVATIVE
COMPOUNDS FROM STEM BARK OF
HOPEA AND THEIR BIOLOGICAL
ACTIVITY TEST
Sri Atuna, Nurfina Aznama, Retno Arianingruma,
Takaya Yb, Niwa Masatakeb
a
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
Objective
Phytochemical study of resveratrol oligomers from
Hopea mengarawan, H. odorata, and H. nigra
METHOD OF
RESEARCH
Sample: milled dried stem bark
Extraction by organic solvent :
acetone or methanol
EKSTRAK
By fractionated (VLC)
Fr. A
Fr. B
Fr. C
Fr. D
Repeated Chromatography
Activity test
BIOACTIVE
COMPOUNDS
Pure compounds
S-1, S-2, … dst
elusidasion structure by
spektroskopi methode
(UV, FT-IR, NMR, MS)
STRUCTURE
MOLECULE
HOW TO ISOLATED COMPOUNDS FROM NATURAL PRODUCT
Maserated by
organic solvent
removal of the
solvent under
reduced
pressure
Prepared for VLC
VLC
Series of fraction
chromatogram from chromatography coloumn
1
4
2
3
5
Isolated compounds from H. mengarawan (5 Kg)
HO
H
HO
O
OH
H
O H
H
HO
OH
OH
H
HO
OH
HO
OH
HO
H
H
OH
H
OH
HO
OH
H
HO H
OH
OH
OH
heimiol A (200 mg),
balanocarpol (300 mg)
H
H H
HO
H
HO
vaticanol G (70 mg)
OH
OH
HO HO
H
HO
HO
H H
H
H H
O
OH
HO
H
H
OH
O
HO
vaticanol B (200 mg)
Isolated compounds from H. odorata (3,8 Kg)
HO
H
O
HO
H O
HO
OH
H
OH
O H
H
HO
HO
OH
H
OH
H
HO
H
H
H
H
H
HO
HO
OH
OH
OH
OH
hopeaphenol (1500 mg)
balanocarpol (300 mg)
HO
4b
HO
HO
H
A2
10a
H
H
OH
7b
H H
8b
H
A1
HO
1a
7a
HO
12b
O
7a
OH
4c OH
B2
H
8a
A2
12a
8a
HO
H
1a
H
1b
OH
12a
A1
OH
O H
B1
4a
H
H
10a
7b
C1
7c
8b 8c
12d
H
H
OH
B2
O
12b
14b
H
OH
4a
OH
OH
B1
4b HO
OH
D2
OH
8d
7d
C2
12c
OH
O
H
ampelopsin H (250 mg)
hemlesyanol C (120 mg)
D1
4d
OH
Isolated compounds from H. odorata (3,8 Kg)
HO
HO
OH
HO
H
H H
OH
H
OH
HO H
HO
H
HO
vaticanol G (200 mg)
Spektrum UV dan IR Vaticanol B
Spectrum 1H and 13C NMR of vaticanol B
OH
HO HO
HO
HH
OH
H
H
HH
O
HO
OH
HO
H
HO
O
H
OH
Spectrum H-H COSY NMR of vaticanol B
12b
7a
7d
7b
8d 8c
8a
7c
8b
8b
OH
HO
HO
D2
C1
H
HO
7c
D1
H
B1
HO
8d
7d
7a
12b
HO
B2
O
C2
H
8a
H 7a O
H
A1
7b
H
7b
A2
HO
7d
8d
H H
8a
8c
OH
OH
OH
Table 3. Data activity test as hydroxyl radical scavenger
IC50
( g/ml)
Note
Balanocarpol
1802,3
Less active
Heimiol A
4575.3
Less active
Vaticanol G
683.96
active
Vaticanol B
2146.6
Less active
Hopheaphenol
61,8
High active
Ampelopsin H
4840,0
Less active
Hemlesyanol C
425,5
active
Ascorbat acid
83,9
High active
1328,1
Less active
Sample
Butylated Hydroxy Toluene
(BHT)
Table. 4. LC50 of some compounds from steam bark of Hopea
against HeLa-S3 cell
No
Sample
LC50 g/ml
Note
682,16
Less active
1
Balanocarpol
2
Heimiol A
Very high
Not active
3
Vaticanol G
Very high
Not active
4
Ampelopsin H
8,12
Very active
5
Vaticanol B
92,04
Very active
6
Hopeaphenol
1931,52
Less active
7
Hemsleyanol C
531,00
Active
8
Doksorubisin
control)
96,27
Very active
(positif
Table. 5. LC50 of some compounds from steam bark of
Hopea against Raji cell
No
Sample
LC50
g/ml
Note
277,58
Active
1
Balanocarpol
2
Heimiol A
Very high
Not active
3
Vaticanol G
11050,96
Not active
4
Ampelopsin H
91,07
Very active
5
Vaticanol B
107,00
Very active
6
Hopeaphenol
135,64
Active
7
Hemsleyanol C
166,84
Active
8
Doksorubisin (positif control)
156,64
Active
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
Conclusion
This research we concluded that resveratrol derivative isolated from the
stem bark of Hopea consist of dimer, trimer, and tetramer resveratrol. Some
compounds have biological activity as antioxidant and cytotoxic effect against
Raji and HeLa-S3 lines cell. Hopeaphenol showed the highest activity as
antioxidant. Whereas ampelopsin H and vaticanol B gives the highest
cytotoxic effect against HeLa-S3 and Raji.
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.
COMPOUNDS FROM STEM BARK OF
HOPEA AND THEIR BIOLOGICAL
ACTIVITY TEST
Sri Atuna, Nurfina Aznama, Retno Arianingruma,
Takaya Yb, Niwa Masatakeb
a
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
Objective
Phytochemical study of resveratrol oligomers from
Hopea mengarawan, H. odorata, and H. nigra
METHOD OF
RESEARCH
Sample: milled dried stem bark
Extraction by organic solvent :
acetone or methanol
EKSTRAK
By fractionated (VLC)
Fr. A
Fr. B
Fr. C
Fr. D
Repeated Chromatography
Activity test
BIOACTIVE
COMPOUNDS
Pure compounds
S-1, S-2, … dst
elusidasion structure by
spektroskopi methode
(UV, FT-IR, NMR, MS)
STRUCTURE
MOLECULE
HOW TO ISOLATED COMPOUNDS FROM NATURAL PRODUCT
Maserated by
organic solvent
removal of the
solvent under
reduced
pressure
Prepared for VLC
VLC
Series of fraction
chromatogram from chromatography coloumn
1
4
2
3
5
Isolated compounds from H. mengarawan (5 Kg)
HO
H
HO
O
OH
H
O H
H
HO
OH
OH
H
HO
OH
HO
OH
HO
H
H
OH
H
OH
HO
OH
H
HO H
OH
OH
OH
heimiol A (200 mg),
balanocarpol (300 mg)
H
H H
HO
H
HO
vaticanol G (70 mg)
OH
OH
HO HO
H
HO
HO
H H
H
H H
O
OH
HO
H
H
OH
O
HO
vaticanol B (200 mg)
Isolated compounds from H. odorata (3,8 Kg)
HO
H
O
HO
H O
HO
OH
H
OH
O H
H
HO
HO
OH
H
OH
H
HO
H
H
H
H
H
HO
HO
OH
OH
OH
OH
hopeaphenol (1500 mg)
balanocarpol (300 mg)
HO
4b
HO
HO
H
A2
10a
H
H
OH
7b
H H
8b
H
A1
HO
1a
7a
HO
12b
O
7a
OH
4c OH
B2
H
8a
A2
12a
8a
HO
H
1a
H
1b
OH
12a
A1
OH
O H
B1
4a
H
H
10a
7b
C1
7c
8b 8c
12d
H
H
OH
B2
O
12b
14b
H
OH
4a
OH
OH
B1
4b HO
OH
D2
OH
8d
7d
C2
12c
OH
O
H
ampelopsin H (250 mg)
hemlesyanol C (120 mg)
D1
4d
OH
Isolated compounds from H. odorata (3,8 Kg)
HO
HO
OH
HO
H
H H
OH
H
OH
HO H
HO
H
HO
vaticanol G (200 mg)
Spektrum UV dan IR Vaticanol B
Spectrum 1H and 13C NMR of vaticanol B
OH
HO HO
HO
HH
OH
H
H
HH
O
HO
OH
HO
H
HO
O
H
OH
Spectrum H-H COSY NMR of vaticanol B
12b
7a
7d
7b
8d 8c
8a
7c
8b
8b
OH
HO
HO
D2
C1
H
HO
7c
D1
H
B1
HO
8d
7d
7a
12b
HO
B2
O
C2
H
8a
H 7a O
H
A1
7b
H
7b
A2
HO
7d
8d
H H
8a
8c
OH
OH
OH
Table 3. Data activity test as hydroxyl radical scavenger
IC50
( g/ml)
Note
Balanocarpol
1802,3
Less active
Heimiol A
4575.3
Less active
Vaticanol G
683.96
active
Vaticanol B
2146.6
Less active
Hopheaphenol
61,8
High active
Ampelopsin H
4840,0
Less active
Hemlesyanol C
425,5
active
Ascorbat acid
83,9
High active
1328,1
Less active
Sample
Butylated Hydroxy Toluene
(BHT)
Table. 4. LC50 of some compounds from steam bark of Hopea
against HeLa-S3 cell
No
Sample
LC50 g/ml
Note
682,16
Less active
1
Balanocarpol
2
Heimiol A
Very high
Not active
3
Vaticanol G
Very high
Not active
4
Ampelopsin H
8,12
Very active
5
Vaticanol B
92,04
Very active
6
Hopeaphenol
1931,52
Less active
7
Hemsleyanol C
531,00
Active
8
Doksorubisin
control)
96,27
Very active
(positif
Table. 5. LC50 of some compounds from steam bark of
Hopea against Raji cell
No
Sample
LC50
g/ml
Note
277,58
Active
1
Balanocarpol
2
Heimiol A
Very high
Not active
3
Vaticanol G
11050,96
Not active
4
Ampelopsin H
91,07
Very active
5
Vaticanol B
107,00
Very active
6
Hopeaphenol
135,64
Active
7
Hemsleyanol C
166,84
Active
8
Doksorubisin (positif control)
156,64
Active
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
Conclusion
This research we concluded that resveratrol derivative isolated from the
stem bark of Hopea consist of dimer, trimer, and tetramer resveratrol. Some
compounds have biological activity as antioxidant and cytotoxic effect against
Raji and HeLa-S3 lines cell. Hopeaphenol showed the highest activity as
antioxidant. Whereas ampelopsin H and vaticanol B gives the highest
cytotoxic effect against HeLa-S3 and Raji.
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.