Jurnal Kimia VALENSI: Jurnal Penelitian dan Pengembangan
Ilmu Kimia, 4(1), Mei 2018, 7-13
Available online at Website: http://journal.uinjkt.ac.id/index.php/valensi
Dammarane-Type Triterpenoids from The Stembark of Aglaia argentea
(Meliaceae)
Ace Tatang Hidayat1,2, Kindi Farabi1, Ida Nur Farida2, Kansy Haikal2, Nurlelasari1,
Desi Harneti1, Rani Maharani1,2, Unang Supratman1,2, Yoshihito Shiono3
1
Department of Chemistry, Faculty of Mathematics and Natural Sciences,
Universitas Padjadjaran, Jatinangor 45363, Indonesia
2
Central Laboratory of Universitas Padjadjaran, Jatinangor 45363, Indonesia
3
Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka,
Yamagata 997-8555, Japan
E-mail: unang.supratman@unpad.ac.id
Received: January 2018; Revised: February 2018; Accepted: February 2018; Available Online: May 2018
Abstract
Two dammarane-type triterpenoids, 20S,24S-epoxy-3α,25-dihydroxydammarane (1) and 3α-acetyl-20S,24Sepoxy-3α,25-dihydroxydammarane (2), have been isolated from the stembark of Aglaia argentea. The chemical
structure of compounds (1 and 2) were identified by spectroscopic evidences including UV, IR, 1D-NMR, 2DNMR and MS as well as by comparing with previously reported spectral data. Those compounds were isolated
from this plant for first time. Compounds (1 and 2) showed cytotoxic activity against P-388 murine leukemia
cells with IC50 values of 23.96 and 8.14 M, respectively.
Keywords: Aglaia argentea, Aglaia, dammarane-type triterpenoids, Meliaceae, P-388 Murine leukemia cells.
DOI: http://dx.doi.org/10.15408/jkv.v4i1.7065
1. INTRODUCTION
Dammarane-type triterpenoids widely
distributed in various medicinal plants and
have a great amount of interest in the field of
new drug research and development (Zhao et
al., 2007). Dammarane-type triterpenoids
belong to tetracyclic ring triterpenoids and
their structural characteristic is with H-5α,
CH3-8, H-9α, CH3-10β, H-13β, CH3-14α,
C-17β side chain, and 20R or S configuration
and usually, C-3, C-6, C-7, C-12, C-20, C-23,
C-24, or C-25 are replaced by hydroxyl group;
C-3, C-6, or C-20 are substituted by saccharide
groups and olefinic bond are formatted
between C-5 and C-6, C-20 and C-21, C-20
and C-22, C-22 and CC-23, C-24 and C-25 or
C-25 and C-26 (Liu et al., 2011). Moreover,
cyclization generally displays at C17-side
chain. Specifically, a five-membered ring with
epoxy bond is usually formed between C-20
and C-24, a five-membered lactone ring
usually appears between C-21 and C-23, and a
six-membered ring with epoxy bond displays
between C-20 and C-25 for dammarane-type
triterpenoids (Phan et al., 2011). They are
usually classified into protopanaxdiol and
protopanaxtriol (with 6-OH) groups based on
their aglycone moieties. Furthermore, in
pharmacological research, dammarane-type
triterpenoids, as well as their derivatives,
showed various bioactivities such as antitumor,
antiinflammatory,
immunostimulatory,
neuronal
cell
proliferatory,
antiaging,
antibacterial, antidiabetes, and antiosteoporosis
abilities (Jin et al., 2011).
The genus Aglaia is the largest genus
of the family of Meliaceae comprises more
than 100 species distributed mainly in India,
Indonesia, Malaysia, and parts of the Western
Pacific region (Leong et al., 2016). Some
species of Aglaia have been phytochemically
investigated previously with major constituents
Copyright©2018, Published by Jurnal KimiaVALENSI: Jurnal Penelitian dan Pengembangan Ilmu Kimia,
P-ISSN: 2460-6065, E-ISSN: 2548-3013
Jurnal Kimia VALENSI, Vol. 4, No. 1, Mei 2018 [7-13]
of dammarane-type triterpenoids (Zhang et al.,
2010; Harneti et al., 2012) and cycloartanetype triterpenoids (Awang et al., 2012; Leong
et al., 2016) and glabretal-type triterpenoids
(Su et al., 2006). In our continous search for
novel secondary metabolites from Indonesian
Aglaia plants, we isolated and described
triterpenoids, aglinone and aglinin E, from the
bark of A. smithii (Harneti et al., 2012), and
protolimonoid from the stembark of
A. argentea (Farabi et al., 2017). In the further
screening for novel triterpenoid compounds
from Indonesia Aglaia plants, we found that
the n-hexane of A. argentea exhibited the
presence of triterpenoids. We report herein the
isolation, structural elucidation of dammaranetype triterpenoid compounds (1-2).
2. MATERIAL AND METHODS
General Experimental Prosedure
Melting points were measured on an
electrothermal melting point apparatus and are
uncorrected. The IR spectra were recorded on
a Perkin-Elmer spectrum-100 FT-IR in KBr.
Mass spectra were obtained with a Synapt G2
mass spectrometer instrument. NMR data
were recorded on a JEOL ECZ-600
spectrometer at 600 MHz for 1H and 150 MHz
for 13C and JEOL JNM A-500 spectrometer at
500 MHz for 1H and 150 MHz for 13C,
chemical shifts are given on a (ppm) scale
and tetramethylsilane (TMS) as an internal
standard. Column chromatography was
conducted on silica gel 60 (Kanto Chemical
Co., Inc., Japan). TLC plates were precoated
with silica gel GF254 (Merck, 0.25 mm) and
detection was achieved by spraying with 80%
H2SO4 in water, followed by heating.
Plant Material
The stembark of A. argentea were
collected in Bogor Botanical Garden, Bogor,
West Java Province, Indonesia in June 2015.
The plant was identified by the staff of the
Bogoriense Herbarium, Bogor, Indonesia and a
voucher specimen (No. Bo-1288718) was
deposited at the Herbarium.
Extraction and Isolation
The dried and powdered of A.
argentea (2.5 kg) was extracted with methanol
(14 L) at room temperature for 5 days. After
removing the solvent, the methanol extract
(133.5 g) was recovered. The extract was then
8
P-ISSN : 2460-6065, E-ISSN : 2548-3013
suspended to water (500 mL) and successively
extracted with n-hexane (2×1 L), ethyl acetate
(2×1 L) and n-butanol (2×1 L) to afford nhexane (27 g), ethyl acetate (16 g) and nBuOH (36 g) extracts, respectively. The nhexane soluble fraction (26.3 g) was separated
by vacum liquid chromatography on silica gel
60 using a gradient n-hexane and EtOAc to
give nine fractions (A–I). Fraction B (2.50 g)
was chromatographed on a column of silica
gel, eluted with a gradient of n-hexane–EtOAc
(10:0–1:1), to give six subfractions (C01–
C06). Subfraction C03 (250 mg) was
chromatographed on a column of silica gel,
eluted with CH2Cl2:CHCl3 (9.5:0.50), to give
five subfractions (C03A-C03D). Subfraction
C03C was separated on preparative TLC on
silica gel GF254, eluted with n-hexane:EtOAc
(8.5:1.5), to give 1 (15.2 mg). Fraction C and
D were combined (1.80 g) and was
chromatographed on a column of silica gel,
eluted with a gradient of n-hexane–EtOAc
(10:1–1:10), to give seven subfractions (D01–
D07). Subfraction D05 (340 mg) was
chromatographed on a column of silica gel,
eluted with a gradient of n-hexane–EtOAc
(10:1–1:10) to afford four subfractions (D05AD05D).
Subfraction
D05C
was
chromatographed on a column of silica gel,
eluted with a gradient of CHCl3–EtOAc (10:1–
1:10) to give 2 (10.5 mg).
3. RESULTS AND DISCUSSION
The methanolic extract from the dried
stembark of A. argentea was concentrated and
extracted successively with n-hexane, ethyl
acetate, and n-butanol. The n-hexane exhibited
the presence of triterpenoid compounds. By
using triterpenoid test to guide separations, the
n-hexane fraction was separated by
combination of column chromatography on
silica gel and preparative TLC on silica gel
GF254 to afford two dammarane-type
triterpenoids (1-2).
20S,24S-epoxy-3α,25-dihydroxydammarane
(1)
White crystal, melting points 166-167
°C; IR (KBr) vmax 2866, 3457, 1457, 1380,
1055 cm-1;1H-NMR (CDCl3, 600 MHz), 13CNMR (CDCl3, 150 MHz), See Table 1; ESIMS m/z 461.36 [M+H]+, (calcd. for C30H52O3
m/z 460.39).
Dammarane-Type Triterpenoids from the Stembark of Aglaia argentea (Meliaceae)
3α-acetyl-20S,24Sepoxy-3α,25dihydroxydammarane (2)
Solid amorphous powder; IR (KBr)
vmax 3200, 2949, 1705, 1457, 1380, 1080 cm-1;
1
H-NMR (CDCl3, 500 MHz); 13C-NMR
(CDCl3, 125 MHz), see Table 1; HR-TOFMS
m/z 501.3770 [M-H]-, (calcd. for C32H54O4 m/z
502,4022).
Compound (1) was isolated as a white
needle crystal, melting points, 166-167 oC. The
molecular formula of (1) was established to be
C30H52O3 based on of ESI-MS spectra (m/z
461.36 [M+H]+, calcd. for C30H52O3 m/z
460.39) along with NMR data (Tabel 1), thus
requiring five degrees of unsaturation. The UV
spectrum showed no conjugated double based
on the absorption maximum above 200 nm. IR
spectrum of (1) showed the presence of a
hydroxyl group (3457 cm-1), an aliphatic bands
(2866 cm-1), a gem-dimethyl (1457 and 1380
cm-1) and an ether group (1055 cm-1).
1
H-NMR spectrum showed the
presence of eight tertiary methyl signals at H
0.82 (3H, s, CH3-28), 0.84 (3H, s, CH3-18),
0.87 (3H, s, CH3-19), 0.92 (3H, s, CH3-29),
0.95 (3H, s, CH3-30), 1.09 (3H, s, CH3-26),
1.13 (3H, s, CH3-21) and 1.17 (3H, s, CH3-27),
which characteristic for dammarane-type
triterpenoid (Harneti et al., 2014). An
Hidayat, et. al.
oxygenated sp3 methine at H 3.38 (1H, t,
J=3.0 Hz) and an oxygenated sp3 methine in
part of tetrahydrofuran ring at H 3.62 (1H, dd,
J=4.8, 10.2 Hz) were also obsereved in the 1HNMR spectra, supporting the presence of
dammarane-type triterpenoid structure in
compound (1) (Roux et al., 1998).
13
C-NMR spectrum of (1) showed
thirty carbon resonances which were classified
by their chemical shifts and the DEPT
spectrum as eight methyls, ten methylenes, six
methines and six quarternary carbons,
indicating the presence of dammarane-type
triterpenoid (Harneti et al., 2014). The
presence of eight methyl resonances at C15.6
(CH3-30), 16.2 (CH3-18), 16.6 (CH3-19), 22.2
(CH3-28), 24.1 (CH3-26), 27.3 (CH3-21), 27.9
(CH3-27), and 28.4 (CH3-29), as well as two
oxygenated quartenary carbon at C 86.7 and
70.3, supporting the presence of dammaranetype
triterpenoid
with
addition
of
tetrahydrofuran ring (Roux et al., 1998).
In order to clarify the position of
functional groups in compound (1), 1H-1H
COSY and HMBC experiments were carried
out and the results was shown in Figure 1. The
1
H-1H COSY spectrum of 1 displayed the
correlations in C1-C2-C3, C5-C6-C7, C9-C11-C12C13,
C14-C15-C16-C17,
and
C22-C23-C24,
supporting the presence of dammaran-type
triterpenoid structure in (1). In the HMBC
spectrum, the correlations arising from the
tertiary methyl protons to their neighboring
carbons enabled the assignment of the eight
singlet methyls at C-4 (2), C-8, C-10, C-14,
C-20, C-26, and C-27, respectively. A
methylene protons at H 1.55 and methyl
protons at H 0.82 (CH3-29) were correlated to
oxygenated carbon at C 76.4 (C-3), indicated
that a secondary hydroxyl group was attached
at C-3. Methyl protons at H 1.17 and 1.09, as
well as an oxygenated methine at H 3.62 were
correlated to oxygenated carbon at C 70.3
(C-25), indicated that a tertiary alcohol and an
isopropyl group were attached at C-25 and
C-24, respectively. A methine proton at H
1.44 was correlated to C-20 (C 86.7), whereas
the methyl proton at H 1.13 was correlated to
C-20 (C 86.7), C-17 (C 49.8), and C-22 (C
35.3), indicated that a tetrahydrofuran ring was
attached at C-17. The presence of a
tetrahydrofuran ring at C-17 was supported
also by correlation between a methylene proton
at H 1.85 and C-24 (C 86.3).
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Jurnal Kimia VALENSI, Vol. 4, No. 1, Mei 2018 [7-13]
(1)
P-ISSN : 2460-6065, E-ISSN : 2548-3013
(2)
Figure 1. Selected 1H-1H COSY and HMBC correlations for Compounds (1) and (2)
Relative stereochemistry of compound
(1) was determined on the basis of coupling
constant (3J) and chemical shift in the 1H and
13
C-NMR spectra. A methine proton at C-3 has
a 3J 3.0 Hz, indicating that H-2 and H-3 has
axial-equatorial orientation, consequently
3-OH has -orientation (Zhang et al., 2010;
Farabi et al., 2017). A detail analysis of NMR
spectra with side chain of 20,34-epoxy-25hydroxy, indicated that C values can be used
for determining of 24R and 24S isomer, where
C 83.2 for R isomer and 86.5 for S isomer. In
addition, the chemical shift and coupling
constant of H-2 can be used also for
determining 24R and 24S isomer with chemical
shift H 3.7 (1H, t, J=7.0 Hz) and H 3.6 (1H,
dd, J=5.5, 10.0 Hz), respectively (Roux et al.,
1998; Harneti et al., 2012; Harneti et al.,
2014). Compound (1) showed the chemical
shift for C-23 and H-24 [C 86.3 and H 3.62
(1H, dd, J=4.8, 10.2 Hz), as well as C 86.7 for
C-20, consequently configuration for C-20 and
C-24 are S orientation.
A comparison of the NMR data of (1)
with
those
of
20S,24R-epoxy-25hydroxydammarane isolated from A. foveolata
(Roux et al., 1998) revealed that the structures
of the two compounds are closely related, the
main differences is the chemical shift of C-24
(C 83.3), whereas compound (1) was C 86.3,
consequently compound (1) was identified as
20S,24S-epoxy-25-hydroxydammarane, which
showed from this plant for the first time.
Compound (2) was isolated as a solid
amorphous powder. The molecular formula of
(2) was established to be C32H54O4 based on of
10
ESI-HRTOFMS spectra (m/z 502.4022
[M+H]+, calcd. for C30H52O3 m/z 502.4022)
together with NMR data (Tabel 1), thus
requiring six degrees of unsaturation. The UV
spectrum showed no conjugated double based
on the absorption maximum above 200 nm. IR
spectrum of (2) showed the presence of a
hydroxyl group (3200 cm-1), an aliphatic bands
(2949 cm-1), a gem-dimethyl (1457 and 1380
cm-1) and an ether group (1080 cm-1).
A NMR spectra of (2) was very similar
to those of (1), the main differences are the
absence one of the hydroxyl group and the
presence of an acetyl group at [C 171.1 (s),
21.5 (q) and H 2.08 (3H, s)]. In order to
determine the position of newly acetyl group,
HMBC experiment was carried, as the results
was shown in Figure 1. In the HMBC
spectrum, a methyl proton at H 2.08 was
correlated to carbonyl ester at C 171.1,
whereas the oxygenated methine at H 4.61
was correlated also to carbonyl ester at C
171.1, indicating that an acetyl group was
attached at C-3.
A detailed comparison of the NMR
spectra of (2) to those of 3α-acetil-20S,24Sepoxy-25-hydroxydammarane isolated from
A. foveolata (Roux et al., 1998) revealed that
the structures of the two compounds are very
similar, consequently compound (2)
was
identified as 3α-asetil-20S,24S-epoxy-25hydroxydammarane, which showed from this
plant for the first time.
The cytotoxicity effects of the two
isolated compounds (1 and 2) against the
P-388 murine leukemia cells were conducted
Dammarane-Type Triterpenoids from the Stembark of Aglaia argentea (Meliaceae)
Hidayat, et. al.
25-hydroxydammarane (2) showed stronger
activity
than
20S,24S-epoxy-25hydroxydammarane (1), indicated that the
presence of an acetyl group increase the
cytotoxic
activity
in
dammarane-type
triterpenoid sctructure.
according to the method described in previous
paper (Harneti et al., 2012; Harneti et al.,
2014; Farabi et al., 2017) and were used an
Artonin E (IC50 0.75 µg/mL) as a positive
control (Farabi et al., 2018; Hidayat et al.,
2017). Cytotoxic activity of two dammaranetype triterpenoids, 3α-asetil-20S,24S-epoxy-
Table 1. NMR data for Compounds (1 and 2)
Position of
Carbon
13
1
C NMR
C (mult.)
33.7 (t)
2
25.4 (t)
3
4
5
6
76.4 (d)
37.3 (s)
49.6 (d)
18.3 (t)
7
34.8 (t)
8
9
10
11
40.7 (s)
50.7 (d)
37.7 (s)
21.7 (t)
12
27.1 (t)
13
14
15
42.8 (d)
50.2 (s)
31.5 (t)
16
25.9 (t)
17
18
19
20
21
22
49.8 (d)
16.2 (q)
16.6 (q)
86.7 (s)
27.3 (q)
35.3 (t)
23
26.4 (t)
24
25
26
27
28
29
30
1
86.3 (d)
70.3 (s)
27.9 (q)
24.1 (q)
28.4 (q)
22.2 (q)
15.6 (q)
(1)*
H NMR
H (Integ. Mult., J=Hz)
1.42 (1H, m)
1.54 (1H, m)
1.55 (1H, m)
1.62 (1H, m)
3.38 (1H, t, 3.0)
1.24 (1H, m)
1.39 (1H, m)
1.54 (1H, m)
1.63 (1H, m)
1.74 (1H, m)
1.44 (1H, dd, 2.4, 5.2)
1.53 (1H, m)
1.24 (1H, dd, 5.2, 7.0)
1.75 (1H, m)
1.82 (1H, dd, 4.4, 7.0)
1.62 (1H, dd, 4.4, 6.2)
1.04 (1H, m)
1.24 (1H, m)
1.51 (1H, m)
1.56 (1H, m)
1.44 (1H, dd, 2.5, 6.2)
0.84 (3H, s)
0.87 (3H, s)
1.13 (3H, s)
1.22 (1H, m)
1.34 (1H, m)
1.85 (1H, m)
1.76 (1H, m)
3.62 (1H, dd, 4.8, 10.2)
1.17 (3H, s)
1.09 (3H, s)
0.92 (3H, s)
0.82 (3H, s)
0.95 (3H, s)
1
13
C NMR
C (mult.)
34.3 (t)
24.8 (t)
78.5 (d)
36.8 (s)
50.6 (d)
18.2 (t)
35.3 (t)
40.6 (s)
50.8 (d)
37.2 (s)
21.7 (t)
27.1 (t)
42.8 (d)
50.2 (s)
31.6 (t)
25.9 (t)
49.9 (d)
15.6 (q)
16.1 (q)
86.7 (s)
27.4 (q)
35.2 (t)
26.4 (t)
86.4 (d)
70.4 (s)
28.0 (q)
24.1 (q)
27.9 (q)
21.8 (q)
16.7 (q)
171.1 (s)
21.5 (q)
(1)**
H NMR
H (Integ. Mult., J=Hz)
1.40 (1H, m)
1.56 (1H, m)
1.56 (1H, m)
1.61 (1H, m)
4.61 (1H, t, 3.0)
1.42 (1H, dd, 3.0, 12.0)
1.38 (1H, m)
1.53 (1H, m)
1.65 (1H, m)
1.76 (1H, m)
1.20 (1H, dd, 2.6, 5.8)
1
1.52 (1H, m)
1.27 (1H, dd, 4.6, 6.5)
1.78 (1H, m)
1.84 (1H, dd, 6.5, 7.2)
1.65 (1H, dd, 7.2, 10.8)
1.05 (1H, dd, 6.2, 9.8)
1.48 (1H, m)
1.87 (1H, m)
1.92 (1H, m)
1.46 (1H, dd, 2.7, 6.8)
0.96 (3H, s)
0.85 (3H, s)
1.14 (3H, s)
1.22 (1H, m)
1.35 (1H, m)
1.87 (1H, m)
1.74 (1H, m)
3.63 (1H, dd, 4.8, 10.2)
1.18 (3H, s)
1.10 (3H, s)
0.82 (3H, s)
0.86 (3H, s)
0.90 (3H, s)
2.08 (3H, s)
*(600 MHz for 1H and 150 MHz for 13C in CDCl3)
** (500 MHz for 1H and 125 MHz for 13C in CDCl3)
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Jurnal Kimia VALENSI, Vol. 4, No. 1, Mei 2018 [7-13]
4. CONCLUSIONS
Two dammarane-type triterpenoid,
20S,24S-epoxy-25-hydroxydammarane (1) and
3α-asetil-20S,24S-epoxy-25hydroxydammarane (2) have been isolated
from the stembark of Chisocheton pentandrus.
This results supported the presence of
dammarane-type triterpenoid in Aglaia genus.
Compound (2) showed stronger cytotoxic
activity against P-388 murine leukemia cells,
indicated that the presence of an acetyl group
in dammarane-type triterpenoid structure can
increase cytotoxic activity.
ACKNOWLEDGEMENTS
This investigation was supported by
Directorate General of Higher Education,
Ministry of Research, Technology, and Higher
Education, Indonesia (Postgraduate Grant,
2016-2018 by Unang Supratman). We thank
Mrs. Suzany Dwi Elita at Department of
Chemistry, Faculty of Mathemathics and
Natural Sciences, Institute Technology
Bandung, Indonesia for cytotoxicity bioassay.
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