A new triterpene glycoside from the stems of Lagerstroemia indica

Article abstract of DOI:10.1007/s12272-016-0746-4

A bioassay-guided fractionation and chemical investigation of the stems of Lagerstroemia indica resulted in the isolation and identification of a new triterpene glycoside, lagerindiside (1), along with nine known triterpenes (2–10). The structure of this new compound was elucidated on the basis of 1D and 2D nuclear magnetic resonance spectroscopic data analysis as well as chemical method. The cytotoxic activities of the isolates (1–10) were evaluated by determining their inhibitory effects on four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) using a sulforhodamine B bioassay. Compounds 3 and 4 showed potent cytotoxicity on the tumor cell lines with IC₅₀values ranging from 3.38 to 6.29?μM.

Full text of DOI:10.1007/s12272-016-0746-4

Arch. Pharm. Res.
DOI 10.1007/s12272-016-0746-4
RESEARCH ARTICLE
A new triterpene glycoside from the stems of Lagerstroemia indica
1
1
2
1
Kyeong Wan Woo
•
Joon Min Cha
•
Sang Un Choi
•
Kang Ro Lee
Received: 6 January 2016 / Accepted: 17 April 2016
Ó The Pharmaceutical Society of Korea 2016
Abstract A bioassay-guided fractionation and chemical
investigation of the stems of Lagerstroemia indica resulted
in the isolation and identification of a new triterpene gly-
coside, lagerindiside (1), along with nine known triterpenes
detoxicant and diuretic (Lee et al. 2011). Previous phyto-
chemical investigations on L. indica have reported the
isolation of alkaloids (Kim et al. 2009b), triterpenes (Lee
et al. 2011), and flavonoids (Vinod et al. 2010). In our
continuing search for bioactive constituents from Korean
medicinal plants, we recently reported the isolation of
phenolic derivatives and their anti-inflammatory and
cytotoxic activities (Woo et al. 2015). Our interest in the
research on new bioactive constituents from the stems of L.
indica further led us to investigate this plant since the our
(
2–10). The structure of this new compound was elucidated
on the basis of 1D and 2D nuclear magnetic resonance
spectroscopic data analysis as well as chemical method.
The cytotoxic activities of the isolates (1–10) were evalu-
ated by determining their inhibitory effects on four human
tumor cell lines (A549, SK-OV-3, SK-MEL-2, and
HCT15) using a sulforhodamine B bioassay. Compounds 3
and 4 showed potent cytotoxicity on the tumor cell lines
with IC50 values ranging from 3.38 to 6.29 lM.
screening test confirmed that CHCl and EtOAc fraction of
3
the source showed significant cytotoxicity against A549,
SK-OV-3, SK-MEL-2, and HCT-15 using a sulforho-
damine B (SRB) bioassay. Using the bioactivity-guided
isolation techniques, a new triterpene glycosides (1), along
with nine known triterpenes (2–10) were isolated from the
active fractions (Fig. 1) and evaluated the cytotoxicities of
all isolates (1–10). In this paper, we report the isolation,
structural elucidation (1–10), and cytotoxicity of all the
isolated compounds.
Keywords Lagerstroemia indica Á Lythraceae Á
Triterpene glycoside Á Cytotoxicity
Introduction
Lagerstroemia indica (Lythraceae) is a decorative shrub,
widely distributed in Korea, Japan, and China (Lee 1996).
The root of this plant has been used as an astringent,
Materials and methods
General experimental procedure
Electronic supplementary material The online version of this
article (doi:10.1007/s12272-016-0746-4) contains supplementary
material, which is available to authorized users.
Thin-layer chromatography (TLC) was performed using
Merck precoated Silica gel F254 plates and reversed-phase
(RP)-18 F254s plates. Spots were detected on TLC under
ultraviolet (UV) light or by heating after spraying with
10 % H SO in C H OH (v/v). Packing material of
&
Kang Ro Lee
krlee@skku.edu
1
2
4
2 5
Natural Products Laboratory, School of Pharmacy,
Sungkyunkwan University, 2066 Seobu-Ro, Jangan-ku,
Suwon, Gyeonggi-do 440-746, Republic of Korea
molecular sieve column chromatography was Sephadex
LH-20 (Pharmacia Co. Ltd). Low-pressure LC was per-
formed over a LiChroprep Lobar-A RP-C18 (240 9 10 mm
i.d.) column with a FMI QSY-O pump (ISCO). Semi-
2
Korea Research Institute of Chemical Technology,
Daejeon 305-600, Republic of Korea
123

K. W. Woo et al.
3
0
HO
2
0
2
9
1
1
O
O
O
25
26
1
28
HO
HO
OH
HO
OH
O
O HO
OH
1
5
HO
OH
O
OH
OH
O
6
27
1
'
OH HO
HO
OH
OH
24
23
1
2
3
O
O
O
HO
HO
HO
O
OH
O
OH
OH
O
O
HO
OH
OH
OH
OH
4
5
6
O
OH
O
OH
O
O
O
HO
HO
HO
HO
OH
OH
HO
HO
OH
10
OH
7
8
9
Fig. 1 Structures of compounds 1–10
preparative high performance liquid chromatography
HPLC) was performed using a Gilson 306 pump (Gilson,
Middleton, WI) with a Shodex refractive index detector
were authenticated by one of the authors (K. R. Lee). A
voucher specimen (SKKU-NPL-1203) of the plant was
deposited in the herbarium of the School of Pharmacy,
Sungkyunkwan University, Suwon, Korea.
(
Ò
(
Shodex, New York, NY) and Econosil RP- C18 10 l
column (250 9 10 mm). Optical rotations were obtained
on a JASCO P-1020 Polarimeter (Jasco, Easton, MD).
Infrared (IR) spectra were recorded on a Bruker IFS-66/S
FT-IR spectrometer. Nuclear magnetic resonance (NMR)
Extraction and isolation
The stems of L. indica (5 kg) were extracted with 80 %
MeOH (60 L) three times under reflux. The filtrate was
evaporated under reduced pressure to yield a MeOH extract
(300 g), which was suspended in water (800 mL, 5 times)
and solvent-partitioned to afforded n-hexane (17.3 g, yield
1
1
spectra, including
H– H correlation spectroscopy
(
(
(
COSY), heteronuclear multiple quantum coherence
HMQC), hetero nuclear multiple bond correlation
HMBC), were recorded on a Varian UNITY INOVA
1
NMR spectrometer operating at 700 MHz ( H) and
1
1
5.73 %), CHCl (9.1 g, yield 3.03 %), EtOAc (8.9 g, yield
3
3
75 MHz ( C), with chemical shifts given in ppm (d).
2.96 %), and BuOH (55.0 g, yield 18.33 %) fractions.
Each fraction was evaluated for cytotoxicity against human
tumor cell lines A549, SK-OV-3, SK-MEL-2, and HCT-15,
High resolution (HR)-fast atom bombardment (FAB) mass
spectrometry (MS) and FABMS spectra were obtained on a
JEOL JMS 700 mass spectrometer.
using the SRB bioassay. It was found that the CHCl and
3
ethyl acetate-soluble fractions showed cytotoxic activity
against all the cell lines.
Plant materials
The CHCl fraction (9.1 g) was separated over a silica
3
The stems of L. indica (5 kg) were collected from Goesan
gel column (230–400 mesh, 300 g) with a solvent system
in Chungcheongbuk-do, Korea, in May 2012. The plants
of CHCl /MeOH (30:1 to 1:1) to obtain four fractions (A–
3
1
23

A new triterpene glycoside from the stems of Lagerstroemia indica
1
13
D). Fraction A (2.2 g) was chromatographed on a silica gel
5 5
Table 1 H- and C-NMR data of compound 1 in C D N
column eluted with CHCl /MeOH (60:1 to 1:1) to yield
3
Position
d
H
d
C
Position
d
H
d
C
four fractions (A1–A4). Fraction A2 (1.0 g) was separated
over a RP-C18 open column (230–400 mesh, 150 g) with a
solvent system of 100 % MeOH to obtain seven subfrac-
tions (A21–A27). Subfraction A25 (35 mg) was purified by
1
2.41 m, 1.30 m 50.5 19
2.69 m
–
50.0
72.3
30.8
36.9
28.9
19.2
19.5
17.7
15.7
2
4.27 m
3.42 d (9.0)
–
69.1 20
84.3 21
40.8 22
56.6 23
68.0 24
3
2.21 m
semi-preparative reversed-phase HPLC using
a
4
2.13 m, 1.65 m
1.45 s
2
2
50 9 10 mm i.d., 10 lm, Econosil RP-C18 column
Alltech) with a solvent system of 97 % MeOH (1 L, flow
rate; 2 mL/min) to isolate compounds 3 (5 mg, yield
.00167 %) and 8 (4 mg, yield 0.00134 %). Subfraction
5
1.09 m
4.81 brs
(
6
1.76 s
7
1.98 m, 1.77 m 42.9 25
1.62 s
0
8
–
44.0 26
52.1 27
38.7 28
22.4 29
1.86 s
A26 (15 mg) was purified by semi-preparative reversed-
phase HPLC with a solvent system of 97 % MeOH to
afford compound 4 (3 mg, yield 0.001 %). Fraction A4
9
1.65 m
–
1.13 s
10
11
12
–
175.6
31.6
27.3
95.5
74.2
79.4
71.2
78.9
62.2
13
1.78 m
1.75 m
3.01 m
–
1.43 s
(
900 mg) was separated over a RP-C18 open column
230–400 mesh, 150 g) with a solvent system of 90 %
29.2 30
1.36 s
(
0
1
1
1
1
1
1
3
4
5
6
7
8
37.9
41.1
30.8
1
2
3
4
5
6
6.44 d (8.5)
4.21 m
4.05 m
4.40 m
4.32 m
4.44 m
MeOH to obtain five subfractions (A41–A45). Subfraction
A44 (10 mg) and A45 (17 mg) were purified by semi-
preparative reversed-phase HPLC with a solvent system of
0
0
0
0
0
2.38 m
2.73 m, 1.60 m 32.6
7
0 % MeOH to afford compounds 6 (4 mg, yield
.00134 %) and 9 (3 mg, yield 0.001 %), respectively.
The EtOAc fraction (8.9 g) was separated over a RP-C18
–
57.1
49.1
0
2.02 m
1
NMR data were obtained at 700 MHz for H and 175 MHz for
C
open column (230–400 mesh, 300 g) with a solvent system
of 30–100 % MeOH to obtain ten fractions (A–J). Fraction
E (1.0 g) was chromatographed on a Sephadex LH-20
column (450 g, 3 9 90 cm) and eluted with 80 % MeOH
to yield five subfractions (E1–E5). Subfraction E2
H-2), 2.91 (1H, d, J = 10.0 Hz, H-3), 1.17 (3H, s, Me-23),
1
3
.02 (3H, s, Me-27), 1.01 (3H, s, Me-24), 0.95 (3H, s, Me-
(
220 mg) was chromatographed on a Sephadex LH-20
0), 0.91 (3H, s, Me-25), 0.82 (3H, s, Me-26), 0.81 (3H, s,
13
column (80 % MeOH) and purified by semi-preparative
reversed-phase HPLC with a solvent system of 40 %
MeCN to afford compound 1 (9 mg, yield 0.003 %).
Subfraction E3 (22 mg) was applied to LPLC on a
LiChroprep Lobar-A RP-C18 column eluted with 80 %
MeOH and purified by semi-preparative reversed-phase
HPLC with a solvent system of 70 % MeOH to afford
compound 5 (7 mg, yield 0.00234 %). Fraction F (470 mg)
was separated over a RP-C18 open column (230–400 mesh,
Me-29); C-NMR (500 MHz, CD OD) d 179.0 (C-28),
1
3
44.4 (C-13), 121.7 (C-12), 83.2 (C-3), 68.0 (C-2), 55.4 (C-
5
), 47.7 (C-9), 47.3 (C-1), 46.2 (C-17), 46.0 (C-19), 41.7
(
C-14), 41.5 (C-18), 39.4 (C-4), 39.3 (C-8), 38.0 (C-10),
3.8 (C-21), 32.8 (C-7, 29), 32.7 (C-22), 30.5 (C-20), 28.9
C-23), 27.8 (C-15), 25.7 (C-27), 23.5 (C-11), 23.3 (C-16,
0), 18.4 (C-6), 17.2 (C-26), 17.1 (C-24), 16.4 (C-25);
3
(
3
?
FAB-MS m/z 473 [M?H] .
3
b,23-Dihydroxy-1-oxo-olean-12-en-28-oic acid (10):
1
00 g) with a solvent system of 70–100 % MeOH and
1
colorless gum, H-NMR (500 MHz, C D N) d 5.50 (1H, t,
5
5
purified by semi-preparative reversed-phase HPLC (55 %
MeCN) to afford compound 2 (25 mg, yield 0.00834 %).
Fraction G (40 mg) was purified by semi-preparative
reversed-phase HPLC with a solvent system of 60 %
MeCN to afford compounds 7 (2 mg, yield 0.00067 %) and
J = 3.5 Hz, H-12), 4.55 (1H, dd, J = 12.0, 5.0 Hz, H-3),
.12 (1H, d, J = 11.0 Hz, H-23a), 3.71 (1H, d,
J = 11.0 Hz, H-23b), 3.44 (1H, t, J = 12.0 Hz, H-2b),
.26 (1H, dd, J = 14.0, 4.0 Hz, H-18b), 2.79 (1H, dd,
J = 11.5, 5.0 Hz, H-2a), 2.72 (1H, dt, J = 18.0, 5.5,
.5 Hz, H-11a), 2.65 (1H, dd, J = 11.0, 6.0 Hz, H-9), 1.36
4
3
1
0 (2 mg, yield 0.00067 %).
4
2
D
5
Compound (1): colorless gum, ½aŠ —8.5 (c 0.09,
(3H, s, Me-25), 1.23 (3H, s, Me-27), 1.17 (3H, s, Me-24),
MeOH); IR (KBr) m
2973, 2944, 2870, 2830, 1707,
1.08 (3H, s, Me-26), 0.99 (3H, s, Me-30), 0.93 (3H, s, Me-
13
max
1
-
052, 1032, 1022 cm ; H NMR (700 MHz, C D N) and
1
1
29); C-NMR (500 MHz, C D N) d 212.9 (C-1), 179.8 (C-
5
5
5 5
1
3
C NMR (175 MHz, C D N) data, see Table 1; HR-FAB-
5
28), 143.9 (C-13), 123.1 (C-12), 72.6 (C-3), 65.8 (C-23),
52.2 (C-10), 47.2 (C-5), 46.6 (C-17), 45.9 (C-19), 44.9 (C-
2), 43.6 (C-4), 42.2 (C-18), 42.0 (C-14), 39.5 (C-8), 39.4
(C-9), 34.1 (C-21), 33.1 (C-29), 32.9 (C-22), 32.7 (C-7),
30.7 (C-20), 28.1 (C-15), 25.8 (C-27), 25.5 (C-11), 23.6 (C-
5
?
MS 691.4033 m/z [M ? Na] (calcd for C H O Na,
3
6 60 11
6
91.4033).
Maslinic acid (9): colorless gum, H-NMR (500 MHz,
CD OD) d 5.27 (1H, t, J = 3.5 Hz, H-12), 3.62 (1H, m,
1
3
123

K. W. Woo et al.
3
0), 23.5 (C-16), 17.9 (C-26), 17.7 (C-6), 15.4 (C-25), 13.5
(s, Me-30) and 1.13 (s, Me-27) and three oxygenated
?
C-24); FAB-MS m/z 487 [M?H] .
(
methine protons at d 4.81 (brs, H-6), 4.27 (m, H-2), and
H
1
3
3
.42 (d, J = 9.0 Hz, H-3). In the C NMR (including
DEPT) spectrum, a total of 30 carbon signals, composed of
methyls (d 31.6 28.9, 27.3, 19.5, 19.2, 17.7, and 15.7), 3
Acid hydrolysis of 1 and sugar determination
7
C
Compound 1 (1.0 mg) was refluxed with 1 mL of 1 N HCl
for 2 h at 100 °C. The hydrolysate was extracted with
oxygenated methines (d 84.3, 69.1, and 68.0), oxygenated
C
quaternary carbon (dC 72.3), carbonyl carbon (dC 175.6)
were observed, together with the sugar group (dC 95.5,
79.4, 78.9, 74.2, 71.2, and 62.2). From these data, com-
pound 1 was deduced to be lupane-type triterpene gly-
EtOAc and the extract was evaporated in vacuo. The H O
2
layer was neutralized by passage through an Amberlite
IRA-67 column (Sigma, St. Louis, MO) and evaporated to
give D-glucose identified by co-TLC (CHCl :MeOH:H
1
13
coside (El-Gamal 2008). Comparison of the H- and C-
NMR data of 1 with those of 2 indicated that the only
difference was the presence of 2-hydroxy isopropyl moiety
in 1, instead of allylic methyl group in 2. The HMBC
correlations of Me-29/C-19, Me-29/C-20, Me-30/C-19, and
Me-30/C-20 confirmed 2-hydroxy isopropyl moiety to be
located at C-19 (Fig. 2). The relative configuration of
aglycone was determined to be the same as compound 2 by
NOESY cross-peaks of H-23/H-3, H-23/H-5, H-5/H-6,
H-24/H-2, H-24/H-25, H-27/H-9, H-27/H-18, H-13/H-19,
and H-13/H-26 (Adnyana et al. 2000) (Fig. 3). Acid
hydrolysis of 1 afforded D-glucose, which was detected by
co-TLC and identified by the sign of its specific rotation
value (Kim et al. 2009a). The J coupling (d, J = 8.5 Hz) of
the anomeric proton signal at dH 6.44 indicated b-orien-
tation. Thus, the structure of compound 1 was determined
as shown in Fig. 1 and named lagerindiside.
3
2-
O = 2:1:0.2, R value 0.2) with an authentic sample and
f
25
measurement of optical rotation {½aŠ ?54.0 (c = 0.05,
D
H O)}.
2
Cytotoxicity assay
A sulforhodamine B bioassay (SRB) was used to determine
the cytotoxicity of each compound on four cultured human
cancer cell lines (Skehan et al. 1990). The assays were
performed at the Korea Research Institute of Chemical
Technology. The cell lines used were A549 (non small cell
lung adenocarcinoma), SK-OV-3 (ovarian cancer cells),
SK-MEL-2 (skin melanoma), and HCT15 (colon cancer
cells). Doxorubicin (Sigma Chemical Co., C98 %) was
used as a positive control.
Cytotoxic activity
Results
The cytotoxic activities of the isolates (1–10) were evaluated
by determining their inhibitory effects on human tumor cell
lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) using the
SRB bioassay (Skehan et al. 1990). Compounds 3 and 4
showed significant cytotoxicity on all tested tumor cell lines
with IC50 values (Table 2). The linked acetoxyl moiety at
C-3 in 4 significantly increased cytotoxic activity when
compared to the compound 8. Compounds 1, 2, and 5, which
combined the glucose at C-28 has a result that not show
Structure elucidation
Purification of the CHCl and EtOAc-soluble fractions by
3
multiple chromatographic steps isolated a new triterpene
glycoside (1), together with nine known triterpenes (2–10).
The known compounds were identified as quadranoside I
(
2) (Adnyana et al. 2000), betulinic acid (3) (Choi et al.
006), 3b-acetoxyolean-12-en-28-acid (4) (Kwon et al.
008), arjunolic acid 28-O-glucopyranoside (5) (Jayas-
2
2
inghe et al. 1993), hederagenin (6) (He et al. 2003),
arjunolic acid (7) (Kim et al. 2008), oleanolic acid (8)
HO
(
Seebacher et al. 2003), maslinic acid (9) (Taniguchi et al.
002), and 3b,23-dihydroxy-1-oxo-olean-12-en-28-oic acid
10) (Okada et al. 2003) by comparing the H-, C-NMR,
2
1
13
(
O
HO
and MS spectral data with the literature values.
Compound 1 was obtained as a colorless gum. The
molecular formula was determined to be C H O Na
HO
HO
OH
O
3
6
60 11
O
?
OH
OH
from the molecular ion peak [M?Na] at m/z 691.4033
calcd for C H O Na, 691.4033) in the positive-ion HR-
(
3
6 60 11
OH
1
FAB-MS. The H-NMR spectrum showed signals for seven
tertiary methyl groups at d 1.86 (s, Me-26), 1.76 (s, Me-
H
Fig. 2 COSY (bold lines) and HMBC (arrow) correlations of
compound 1
2
4), 1.62 (s, Me-25), 1.45 (s, Me-23), 1.43 (s, Me-29), 1.36
1
23

A new triterpene glycoside from the stems of Lagerstroemia indica
Korea (NRF), funded by the Ministry of Education, Science and
Technology (2013R1A1A2A10005315). We are thankful to the Korea
Basic Science Institute (KBSI) for the measurements of NMR and MS
spectra.
O
O
H
H
2
5
26
H
HO
13
H
Compliance with ethical standards
2
4
H
OH
1
8
HO
HO
Conflict of interest All authors have no conflict of interest to
declare.
9
5
H
H
2
3
H
27
H
H
H
H
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1
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13
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8a-oleanolic acid, ursolic acid and their 11-oxo derivatives.
This study elucidated the structures of one new triterpene
glycoside, lagerindiside (1) and nine known triterpene
present in the stems of L. indica using bioactivity-guided
isolation, spectroscopic data analysis, and chemical meth-
ods. To evaluate compounds 1–8 as cytotoxic agents,
compounds 3 and 4 had significant cytotoxicity on all of
the tested cell lines, with IC50 values ranging from 3.38 to
6.29 lM. These results implied that triterpene derivatives
from L. indica could be used as candidates for the treat-
ment of various cancer diseases.
Woo KW, Suh WS, Subedi L, Kim SY, Choi SU, Kim KH, Lee KR
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Acknowledgments This research was supported by the Basic Sci-
ence Research Program through the National Research Foundation of
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