Sri Atuna, Nurfina Aznama, Retno Arianingruma, Takaya Yb, Niwa Masatakeb

a Department Chemistry education, Universitas Negeri Yogyakarta, Karangmalang, Depok, Sleman, Yogyakarta, 55281b 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 DFr C

Pure compounds S-1, S-2, … etc

Repeated Chromatography

elusidasion structure by Spectroscophy methode(UV, FT-IR, NMR, MS)

BIOACTIVE COMPOUNDS

Methylation & Acethylation

STRUCTURE MOLECULEDERIVATIVES COMPOUNDS

Isolated compounds from H. mengarawan (5 Kg)

O

OH

HH

HOOH

HO

OH

OH

H

H

O

HO

OH

OH

OHHO

OH

HH

H

H

HO

HO

HO

HO

OH

OH

OH

HO

HO

H

H

H HH

H

O

O

HO

HO

HO

HO

HO HO

OHOH

OH

HH

H HHH

H

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

HH

HOOH

HO

OH

OH

H

H

Balanocarpol (300 mg)

OHO

HO

HO

OH

OH

H

H

H

O

OH

OHHOHO

HO

H

H

H

HH

Hopeaphenol (1500 mg)

O

O

HO

HO

OH

H

H

OH OH

HH

HOHO OH

OH

OH

H

H

H

H

A1

A2

B1

B2

1a

4a

7a

8a

10a12a7b

8b

1b

4b

12b

14b

Ampelopsin H (250 mg)

O

OH

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

10a12a7b

8b

4b

12b

7c

8c

12c

7d8d

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 HH

H

vaticanol G (200 mg)

Spectrum UV and IR of Vaticanol B

O

O

HO

HO

HO

HO

HO HO

OH OH

OH

H

H

H HHH

H

H

OH

Spectrum 1H and 13C NMR of vaticanol B

O

O

HO

HO

HO

HO

HOHO

OHOH

OH

H

H

H H

H

H

H

H

OH

D1D2

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/mLHela- S3 Raji Myeloma

123456789101112

Balanocarpol Heimiol AVaticanol 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> 100092.81

> 1000129.71557.44> 1000> 1000> 1000594,2996,87

235.29> 1000> 100034.45

781.4934.69

292.14> 1000> 1000> 1000594,29242,10

197.61> 1000> 1000

*250,15119.62756.43> 1000> 1000533.85298,06

*

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.

e-mail : Atun_1210@yahoo.com