ISOLATION AND STRUCTURE IDENTIFICATION OF BIOACTIVE COMPOUNDS
FROM LEAVES AND TWIGS OF Garcinia succifolia Kurz (GUTTIFERAE)
Rangsinee Hamkool1,*, Pawinee Piyachaturawat2, Surawat Jariyawat2, Kanoknetr Suksen2,
Darunee Soorukram1, Manat Pohmakot1 , Vichai Reutrakul1, Patoomratana Tuchinda1
1Department
of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of
Science, Mahidol University, Bangkok 10400, Thailand.
2
Department of Physiology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
*e-mail: rhamkool@gmail.com, #e-mail: patoomratana.tuc@mahidol.ac.th.
Abstract
Plants of the genus Garcinia were found to possess a wide range of biological activities,
such as antimicrobial, cytotoxic, antitumor, antimalarial, antifungal and antioxidant activities.
Garcinia succifolia Kurz (Guttiferae) is an endemic plant, found in Northern Thailand (Chiang
Mai Province). Therefore, we are interested in the isolation and identification of compounds
from a methanol extract of leaves and twigs. The crude extracts, fractions and isolated pure
compounds were evaluated for their cytotoxic activities against a panel of mammalian cancer
cell lines.
Keywords: Garcinia succifolia, xanthones, benzophenone, triterpenoids
Introduction
Garcinia is the most numerous genus with about 400 species widely distributed in
Tropical Asia, Africa, New Caledonia and Polynesia, being widespread throughout the tropical
and subtropical regions of the world.1 In Thailand, there are twenty six species of Garcinia
having been reported, namely, G. acuminata, G. atroviridis, G. bancana, G. cambogia, G.
costata, G. cowa, G. dulcis, G. forbesii, G. fusca, G. garcilis, G. hanburyi, G. hombroniana, G.
lanessanii, G. mackeaniana, G. mangostana, G. merguensis, G. nervosa, G. nigrolineata, G.
parvifolia, G. rostrata, G. schomburgkiana, G. speciosa, G. succifolia, G. thorelii, G.
vilersianaand, and G. xanthochymus.2
The studies of several Garcinia species indicated the presence of a variety of chemical
constituents. The genus Garcinia (Guttiferae family) is known as a rich source of
polyisoprenylated, benzophenones, xanthones, biflavonoids, triterpenoids and biphenyl
derivatives. Several Garcinia species were found to possess a wide range of biological activities
such as antimicrobial3, cytotoxic5,7, antitumor9, antimalarial8, antifungal4 and
antioxidant5,6activities.
Methodology
The air-dried and finely ground powder from leaves and twigs of Garcinia succifolia
were extracted with methanol at room temperature, followed by filtration. The filtrates were
combined and evaporated to dryness under reduced pressure to give a crude methanol extract.
The extract was evaluated for the cytotoxic activity. The crude methanol extract was dissolved
with EtOAc:MeOH (1:1) at room temperature, followed by MeOH. The crude EtOAc:MeOH
(1:1) was first separated by column chromatography. Further purification by repeated column
chromatography and crystallization afforded macluraxanthone (1), friedelin (2), caloxanthone C
(3), lichexanthone (4), stigmasterol (5) and dichromene II (6).
Results and Discussion
The bioactive MeOH:EtOAc (1:1) soluble fraction (see Table 1), obtained from a crude
MeOH extract of leaves and twigs of G. succifolia, was separated by column chromatography
and recrystallization to yield six known compounds 1-6.
Table 1. Cytotoxic activities of the extract, fractions and pure isolated compounds
Code
a
Cell line
P-388
KB
HT 29
MCF-7
A 549
ASK
Hek 293
Ellipticine
0.10
0.53
0.49
0.45
0.45
0.66
0.45
MeOH extract
10.6
16.29
>20
11.93
>20
>20
17.17
MeOH:EtOAc (1:1)
10.41
16.45
>20
11.88
>20
>20
11.28
MeOH
>20
>20
>20
>20
>20
>20
>20
Residue
>20
>20
>20
>20
>20
>20
>20
F1
>20
>20
>20
>20
>20
>20
>20
F2
8.18
>20
>20
>20
>20
>20
>20
F3
<4
11.46
12.78
9.29
13.38
18.53
11.23
F4
<4
<4
10.28
<4
<4
10.72
<4
F5
3.95
16.04
>20
13.24
>20
>20
15.91
F6
14.87
>20
>20
>20
>20
>20
>20
F7
>20
>20
>20
>20
>20
>20
>20
Ellipticine
0.43
0.54
0.56
0.56
0.51
0.47
0.57
1
1.45
2.16
7.8
1.26
2.22
1.8
5.25
2
>20
>20
>20
>20
>20
>20
>20
3
>20
>20
>20
>20
>20
>20
>20
Results are expressed as ED50 (µg/mL): ED50 < 4 µg/mL is considered active for pure compound. *P-388 = Murine lymphocytic leukemia,
KB = Human nasopharyngeal carcinoma, HT29 = Human colorectal adenocarcinoma, MCF-7 = Human breast cancer, A549 = Human lung
carcinoma, ASK = Cell line from rat glioma, Hek 293= Non-cancerous human embryonic kidney cell line.
Conclusion
Investigation of the MeOH extract of leaves and twigs of Garcinia succifolia has led to the
isolation of macluraxanthone (1), friedelin (2), caloxanthone C (3), lichexanthone (4),
stigmasterol (5) and dichromene II (6).
Fig1. The structures of compounds 1-6 isolated from leaves and twigs of Garcinia succifolia Kurz.
References:
1.
2.
3.
4.
5.
6.
7.
8.
9.
Whitmore TC. Guttiferae. Free flora of Malaya.Vol. 2, Forest Research Institute, Kepong. 1973;2:162-165.
Smitinand T. Thai plant names; Pra Cha Chon Co., Ltd.: Bangkok, 2001, Revised Edition by The Forest
Herbarium Royal Forest Department, 246-248.
Pattalung PN, Wiriyachitra P, Ongsakul M. The antimicrobial activities of rubraxanthone isolated from
Garcinia parvifolia (Miq) Miq. J Sci Soc. Thailand. 1988;14:67-71.
Diserens IS, Marston A, Hamburger M, Rogers C, Hostettmann K. Novel prenylated xanthones from
Garcinia gerrardii Harvey. Helv Chim Acta. 1989;72:1001-1007.
Lin LJ, Lin ZL, Pezzuto JM, Coedell GA. Isogambogic acid and isomorellinol from Garcinia hanburyi.
Magn Reson Chem. 1993;31:340-347.
Minami H, Kuwayama A, Yoshizawa T, Fukuyama Y. Novel prenylated xanthones with antioxidant
property from the wood of Garcinia subelliptica. Chem Pharm Bull. 1996;44(11):2103-2106.
Asano J, Chiba K, Tada M, Yoshii T. Cytotoxic xanthones from Garcinia hanburyi. Phytochemistry. 1996;
41(30):815-820.
Iio C, Miyamoto Y, Nakayama M, Kawai Y, Rao K , Furukawa H. A novel depsidone and some new
xanthones from Garcinia species. Chem Pharm Bull. 1997;45(9):1403-1413.
Nilar, Harrrison LJ. Xanthones from the heartwood of Garcinia mangostana. Phytochemistry. 2002;60(5):
541-548.
Acknowledgement:
This research project is supported by Mahidol University, the Office of the Higher Education Commission
and Mahidol University under the National Research Universities Initiative and Center for Innovation in Chemistry
(PERCH-CIC).