Cytotoxic triterpene saponins from the mangrove Aegiceras corniculatum

Article abstract of DOI:10.1080/14786419.2017.1402320

Using various chromatographic separations, sixteen compounds, including one new triterpene saponin named aegicoroside A (1), were isolated from the leaves of the Vietnamese mangrove Aegiceras corniculatum. Their structures were determined by spectroscopic methods such as 1D and 2D NMR and HR-ESI-MS. The cytotoxic activities of the isolated compounds against MCF7 (breast), HCT116 (colon), B16F10 (melanoma), and A549 (adenocarcinoma) cancer cell lines were also evaluated. Strong cytotoxicity was observed for sakurasosaponin (2) against all four cancer cell lines and for sakurasosaponin methyl ester (3) against MCF7, A549, and HCT116 cell lines with IC₅₀ values ranging from 2.89?±?0.02 to 9.86?±?0.21?μM.

Full text of DOI:10.1080/14786419.2017.1402320

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Cytotoxic triterpene saponins from the mangrove
Aegiceras corniculatum
Le Ba Vinh, Nguyen Thi Minh Nguyet, Seo Young Yang, Jang Hoon Kim,
Nguyen Van Thanh, Nguyen Xuan Cuong, Nguyen Hoai Nam, Chau Van
Minh, Inkyu Hwang & Young Ho Kim
To cite this article: Le Ba Vinh, Nguyen Thi Minh Nguyet, Seo Young Yang, Jang Hoon Kim,
Nguyen Van Thanh, Nguyen Xuan Cuong, Nguyen Hoai Nam, Chau Van Minh, Inkyu Hwang &
Young Ho Kim (2017): Cytotoxic triterpene saponins from the mangrove Aegiceras corniculatum,
Natural Product Research, DOI: 10.1080/14786419.2017.1402320
To link to this article: http://dx.doi.org/10.1080/14786419.2017.1402320
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Published online: 16 Nov 2017.
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Date: 16 November 2017, At: 18:33

Natural Product research, 2017
ꢁꢁpꢂ://ꢃꢄi.ꢄꢅg/10.1080/14786419.2017.1402320
ꢀ
Cytotoxic triterpene saponins from the mangrove Aegiceras
corniculatum
a,b
a
a
c
Le Ba Vinh , Nguyen Thi Minh Nguyet , Seo Young Yang , Jang Hoon Kim ,
b
b
b
b
Nguyen Van Thanh , Nguyen Xuan Cuong , Nguyen Hoai Nam , Chau Van Minh ,
Inkyu Hwang and Young Ho Kim
a
a
ꢆ
b
cꢄꢇꢇꢈgꢈ ꢄf Pꢀꢆꢅmꢆꢉy, cꢀꢊngnꢆm Nꢆꢁiꢄnꢆꢇ univꢈꢅꢂiꢁy, dꢆꢈjꢈꢄn, rꢈpꢊbꢇiꢉ ꢄf Kꢄꢅꢈꢆ; Inꢂꢁiꢁꢊꢁꢈ ꢄf Mꢆꢅinꢈ
ꢉ
Biꢄꢉꢀꢈmiꢂꢁꢅy (IMBc), Viꢈꢁnꢆm aꢉꢆꢃꢈmy ꢄf sꢉiꢈnꢉꢈ ꢆnꢃ tꢈꢉꢀnꢄꢇꢄgy (Vast), hꢆnꢄi, Viꢈꢁnꢆm; Kꢄꢅꢈꢆ aꢁꢄmiꢉ
enꢈꢅgy rꢈꢂꢈꢆꢅꢉꢀ Inꢂꢁiꢁꢊꢁꢈ, Jꢈꢄngꢈꢊp, rꢈpꢊbꢇiꢉ ꢄf Kꢄꢅꢈꢆ
ABSTRACT
ARTICLE HISTORY
Using various chromatographic separations, sixteen compounds,
including one new triterpene saponin named aegicoroside A (1),
were isolated from the leaves of the Vietnamese mangrove Aegiceras
corniculatum. Their structures were determined by spectroscopic
methods such as 1D and 2D NMR and HR-ESI-MS. The cytotoxic
activities of the isolated compounds against MCF7 (breast), HCT116
rꢈꢉꢈivꢈꢃ 6 sꢈpꢁꢈmbꢈꢅ 2017
aꢉꢉꢈpꢁꢈꢃ 17 oꢉꢁꢄbꢈꢅ 2017
KEYWORDS
Aegiceras corniculatum;
ꢁꢅiꢁꢈꢅpꢈnꢈ ꢂꢆpꢄnin; ꢉyꢁꢄꢁꢄxiꢉ
ꢆꢉꢁiviꢁy
(colon), B16F10 (melanoma), and A549 (adenocarcinoma) cancer
cell lines were also evaluated. Strong cytotoxicity was observed
for sakurasosaponin (2) against all four cancer cell lines and for
sakurasosaponin methyl ester (3) against MCF7, A549, and HCT116
cell lines with IC values ranging from 2.89 ± 0.02 to 9.86 ± 0.21 μM.
5
0
1
. Introduction
Aegiceras corniculatum (L.) Blanco (Myrsinaceae) is a shrub or small tree that grows up to 4 m
high and is mainly distributed in Vietnam, China, Cambodia, Malaysia, Singapore, and
Australia (Chi 2012). This plant has been traditionally used as an antiasthamatic, antidiabetic,
and antirheumatic agent (Bandaranayake 2002). The major chemical constituents of
A. corniculatum are terpenoids, alkaloids, fatty acids, and flavonoids (Chandrasekaran et al.
2010; Rajeswari and Rao 2015). The plant and its constituents have also been found to
CONTACT sꢈꢄ Yꢄꢊng Yꢆng
ꢂyyꢆng@ꢉnꢊ.ꢆꢉ.kꢅ; Yꢄꢊng hꢄ Kim
yꢀk@ꢉnꢊ.ꢆꢉ.kꢅ
sꢊppꢇꢈmꢈnꢁꢆꢇ ꢃꢆꢁꢆ fꢄꢅ ꢁꢀiꢂ ꢆꢅꢁiꢉꢇꢈ ꢉꢆn bꢈ ꢆꢉꢉꢈꢂꢂꢈꢃ ꢆꢁ ꢀꢁꢁpꢂ://ꢃꢄi.ꢄꢅg/10.1080/14786419.2017.1402320.
©
2017 Infꢄꢅmꢆ uK limiꢁꢈꢃ, ꢁꢅꢆꢃing ꢆꢂ tꢆyꢇꢄꢅ & Fꢅꢆnꢉiꢂ Gꢅꢄꢊp

2
L. B. VINH ET AL.
have various pharmacological effects such as antibacterial, analgesic, antidiabetic, anti-
inflammatory, cytotoxic, and antioxidant activities (Rajeswari and Rao 2015). As part of our
recent studies on the chemical constituents and biological activities of Vietnamese man-
groves (Huong et al. 2014; Dat et al. 2015; Thao et al. 2015; Vinh et al. 2017), we report herein
the isolation and structural determination of one new triterpene saponin, aegicoroside
A (1), and 15 known compounds from the methanol extract of A. corniculatum, as well as
evaluation of their cytotoxic activity.
2
. Results and discussion
Fractionation and purification of the ethyl acetate (EtOAc) fraction from A. corniculatum led
to isolation of one new saponin termed aegicoroside A (1) and 15 known compounds (2–16,
see Figure 1), namely sakurasosaponin (2) (Ohtani et al. 1993; Lavaud et al. 1999), sakurasos-
aponin methyl ester (3) (Ohtani et al. 1993), (3β, 16α, 20α)-3,16,28-trihydroxyolean-12-en-29-
oic acid 3-{O-β-D-glucopyranosyl (1→2)-O-[β-D-glucopyranosyl (1→4)]-α-L-arabinopyranoside}
(
4) (Zou et al. 2008), rutin (5) (Li et al. 2008), nicotiflorin (6) (Han et al. 2004), oleanolic acid
β-D-glucopyranosyl ester (7) (Lee et al. 2006), isoquecitrin (8) (Guo et al. 2017), quercitrin (9)
Fossen et al. 1998), isomyricitrin (10) (Mansour et al. 2017), hyperoside (11) (Zhang et al.
014), myricitroside (12) (Chung et al. 2004), astragalin (13) (Park et al. 2008), quercetin-3-D-xy-
loside (14) (Kalegari et al. 2011), chondrillasterol (15) (Akjhisa et al. 1987), and stigmasterol
16) (Habib et al. 2007). The known compounds were identified by detailed analysis of their
(
2
(
spectroscopic data and comparison with previously reported values.
Aegicoroside A (1) was obtained as a white amorphous powder. The molecular formula
(
1
C H O ) was determined by HR-ESI-MS with a protonated molecular ion peak at m/z
54 86 22
+
+
109.5496 [M + Na] (calcd for C H NaO , 1109.5503). The IR spectrum of compound 1
54 86
22
−1
−1
showed absorption due to hydroxyl (3349.8 cm ) and ketone (1740.5 cm ) groups. The NMR
spectra (see Supplementary material) are indicative of a triterpene saponin with seven tert-me-
thyl proton signals at δ 0.76, 0.86, 0.92, 0.93, 1.16, 1.19, and 1.28 (each, 3H, s) as well as four
H
1
13
anomeric carbon signals at δ 100.8, 104.5, 104.7, and 107.3. The H and C NMR spectra for
C
4
R1
R2
H
R3
H
1
2
3
OH
OH
Glc
Glc
H
R1
Rut
Rut
Glc
Rha
Glc
Gal
Rha
Glc
Xyl
R2
OH
H
R3
H
CH
3
5
6
8
9
H
OH
OH
OH
OH
OH
H
H
H
1
0
1
2
OH
H
1
1
OH
H
7
5
13
14
1
1
5
6
7
OH
H
Figure 1. tꢀꢈ ꢂꢁꢅꢊꢉꢁꢊꢅꢈꢂ ꢄf ꢉꢄmpꢄꢊnꢃꢂ 1–16.

NATURAL PRODUCT RESEARCH
3
the aglycon exhibited signals of one oxymethylene [δ 75.7/δ 3.56 and 3.94 (each, 1H, d,
C
H
J = 8.4 Hz)], one oxygenated quaternary carbon [δ 86.9], one oxymethine [δ 89.6/δ 3.28
H
C
H
(
1H, dd, J = 4.2 and 12.0 Hz)] and one ketone group [δ 213.7]. The aglycon of 1 was identified
C
as 13,28-epoxy-3β-hydroxy-16-oleanaone (aegicerin) previously reported from A. corniculatum
1
13
(
(
Zhang et al. 2005) by good agreement of its H and C NMR data with those of aegicerin
Machocho et al. 2003) and clethroidoside C (Liang et al. 2011) as well as further confirmation
by 2D NMR spectra (see Supplementary material). The relative configurations for the aglycon
of 1 were also identified by NOESY experiment. Proton H-3 (δ 3.28) had a NOESY correlation
H
with H-5 (δ 0.65) indicating α-orientation of H-3. In addition, NOESY correlations of H -15
H
b
(
δ 2.86) with H-26 (δ 1.28) and H -28 (δ 3.94) as well as H-18 (δ 2.06) with H -28 (δ 3.56)
H H b H H a H
and H-30 (δ 0.86) confirmed β-orientation of the epoxy bridge between C-13 and C-28 (see
H
1
1
Figure S8). Detailed analysis of HMQC, HMBC, and H- H COSY correlations led to assignment
of the H and C NMR data for all four sugar moieties (see section 3.3.1 and Table S1).
1
13
13
Comparison of the C NMR data for sugar moieties of 1 (Table S1) with those of sakurasos-
aponin (2) (Ohtani et al. 1993) and caryocaroside III-7 (Alabdul et al. 2006) in combination
with 2D NMR data indicated that the tetrasaccharide chain was α-L-rhamnopyrano-
syl-(1→2)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-β-D-glucuronopyranoside.
Furthermore, absolute configurations of the sugar moieties were identified as D-glucuronic
acid, D-galactose, and L-rhamnose by acid hydrolysis of 1 followed by TLC and HPLC analysis
in comparison with the authentic samples (Supplementary material). Attachment of the tet-
rasaccharide chain at C-3 of the aglycon was confirmed by HMBC correlation of the anomeric
proton H-1′ (δ 4.88) with C-3 (δ 89.6). Consequently, the structure of 1 was identified as
H
C
3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)-
β-D-glucuronopyranosyl]-13β,28-epoxy-3β-hydroxy-olean-16-one.
The cytotoxic activities of compounds 1–15 against human cancer cell lines such as MCF7
(
breast), HCT116 (colon), B16F10 (melanoma), and A549 (adenocarcinoma) were evaluated
by MTT assays following previously reported protocols (Vinh et al. 2017) as described in the
Supplementary materials. The results (Table 1) show that sakurasosaponin (2) exhibited
strong cytotoxicity against all the four tested cancer cell lines (MCF7, A549, B16F10, and
HCT116) with IC values of 9.85 ± 0.14, 2.89 ± 0.02, 4.96 ± 0.67, and 3.40 ± 0.48 μM, respec-
50
tively, relative to the positive control, mitomycin C (Table 1). Sakurasosaponin methyl ester
3) also exhibited strong cytotoxicity on MCF7, A549, and HCT116 cell lines with IC values
(
5
0
of 9.86 ± 0.21, 5.45 ± 0.13, and 2.21 ± 0.05 μM, respectively. Significant cytotoxicity was
observed for aegicoroside A (1) against all the cancer cell lines (IC ranging from 20.75 ± 0.06
50
to 41.84 ± 0.64 μM) and for 3 against the B16F10 cell line (IC = 18.27 ± 0.04 μM). The other
5
0
compounds showed no (IC > 100 μM) or weak cytotoxicity (IC from 62.30 ± 0.13 to
5
0
50
90.50 ± 0.60 μM) against the tested cancer cell lines. Given the potential cytotoxicity of 2
and 3, these two compounds might be potential candidates for further investigation on the
molecular mechanisms of action on specific anticancer targets.
3
. Experimental
3
.1. Biological material
The leaves of A. corniculatum were collected at Bai Tu Long bay, Quang Ninh Province,
Vietnam in July 2016, and were identified by Dr Nguyen The Cuong (Institute of Ecology and

4
L. B. VINH ET AL.
Table 1. cyꢁꢄꢁꢄxiꢉ ꢈffꢈꢉꢁ ꢄf ꢉꢄmpꢄꢊnꢃꢂ 1–15.
IC50 values (μM)
Compounds
MCF7
A549
B16F10
HCT116
1
2
3
4
5
6
7
8
9
41.84 ± 0.64
9.85 ± 0.14
9.86 ± 0.21
>100
37.71 ± 0.43
2.89 ± 0.02
5.45 ± 0.13
>100
20.75 ± 0.64
4.96 ± 0.67
18.27 ± 0.04
>100
31.61 ± 1.20
3.40 ± 0.48
2.21 ± 0.05
>100
>100
>100
77.08 ± 5.90
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
>100
5.67 ± 0.70
>100
78.38 ± 3.18
>100
10
11
12
13
14
15
>100
>100
>100
66.37 ± 2.41
>100
>100
2.73 ± 1.37
>100
>100
90.50 ± 0.60
0.74 ± 0.05
62.30 ± 0.13
2.82 ± 0.08
ꢆ
Mitomicin C
ꢆPꢄꢂiꢁivꢈ ꢉꢄnꢁꢅꢄꢇ. Vꢆꢇꢊꢈꢂ ꢆꢅꢈ pꢅꢈꢂꢈnꢁꢈꢃ ꢆꢂ mꢈꢆn ± sd (n = 3).
Biological Resources, VAST, Vietnam). The voucher specimens (ĐTCB-HSB 15) have been
deposited at the herbarium of Institute of Marine Biochemistry, VAST, Vietnam.
3
.2. Extraction and isolation
The dried leaves of A. corniculatum (2 kg) were extracted three times (each 5 L) with MeOH
by sonication for 1 h. The MeOH extract was concentrated under reduced pressure to obtain
a residue (200 g). This residue was suspended in water (3 L) and successively partitioned
with n-hexane (4 × 3 L) and EtOAc (3 × 3 L) to give: n-hexane (H, 15 g), EtOAc (E, 25 g) and a
water layer after removal of the solvents.
The EtOAC fraction (E, 25 g) was separated by VLC using gradient concentrations of MeOH
in CH Cl (from 0 to 100%) to give six fractions (E1 to E6). Fraction E4 (9 g) was separated
2
2
into four subfractions (E4.1–E4.4) using silica gel column chromatography (CC) with CH Cl -
2
2
MeOH-H O (3.5:1:0.07, v/v). Subfraction E4.3 (3 g) was separated byYMC RP-18 and Sephadex
2
LH-20 CC using solvent acetone-H O (1:1, v/v) and further purified by silica gel CC with
2
CH Cl -MeOH-H O (2.5:1:0.1, v/v) to afford compounds 1 (30 mg) and 4 (39 mg). Repeating
2
2
2
the same steps as for subfraction E4.3, compounds 2 (200 mg) and 3 (47 mg) were obtained
from subfraction E4.4 (2 g). Subfraction E4.2 (2 g) was separated byYMC RP-18 and Sephadex
LH-20 CC using solvent acetone-water (1:1, v/v) to give compounds 9 (9 mg), 10 (15.7 mg),
and 11 (4.3 mg). Similarly, fraction E3 (7 g) was separated into five subfractions (E3.1–E3.5)
using silica gel CC with EtOAc–MeOH (7:1, v/v). Subfraction E3.4 (3 g) was isolated and puri-
fied by silica gel CC using EtOAc–MeOH (5:1, v/v), followed by Sephadex LH-20 CC to give
compounds 5 (20 mg), 6 (3.7 mg), 7 (3.2 mg), and 8 (25 mg). Subfraction E3.3 (2 g) was puri-
fied by YMC CC using an eluent of MeOH-H O (1.3:1, v/v), followed by Sephadex LH-20 CC
2
to obtain compounds 12 (17 mg), 13 (18 mg), and 14 (11 mg). Fraction E1 (3 g) was separated
by silica gel CC using gradient elution of n-hexane-acetone (20:1–3:1, v/v) to give compounds
1
5 (20 mg) and 16 (3.0 mg).

NATURAL PRODUCT RESEARCH
5
3
.2.1. Aegicoroside A (1)
2
0
White amorphous powder,[ꢀ]C –34.8 (c 0.1, MeOH); IR (KBr) νmax: 3349, 2931, 1740, 1306 and
−
1 1
1
079 cm ; H NMR (pyridine-d , 600 MHz): δ 0.72 (1H, m, H -1), 1.46 (1H, m, H -1), 1.80
5 H a b
(
1H, m, H -2), 2.24 (1H, m, H -2), 3.28 (1H, dd, J = 4.2, 12.0 Hz, H-3), 0.65 (1H, d, J = 10.8 Hz,
a b
H-5), 1.30 (1H, m, H -6), 1.34 (1H, m, H -6), 1.22 (1H, m, H -7), 1.34 (1H, m, H -7), 1.13
a
b
a
b
(
1H, d, J = 13.0 Hz, H-9), 1.48 (1H, m, H -11), 1.75 (1H, m, H -11), 1.58 (1H, br d, J = 12.0 Hz,
a
b
H -12), 2.00 (1H, m, H -12), 2.02 (1H, d, J = 15.6 Hz, H -15), 2.86 (1H, d, J = 15.6 Hz, H -15), 2.06
a
b
a
b
(
1H, dd, J = 5.0, 11.5 Hz, H-18), 1.50 (2H, m, H-19), 1.24 (1H, m, H -21), 1.84 (1H, m, H -21),
a
b
1
1
.22 (1H, m, H -22), 2.29 (1H, m, H -22), 1.19 (3H, s, H-23), 0.92 (3H, s, H-24), 0.76 (3H, s, H-25),
a b
.28 (3H, s, H-26), 1.16 (3H, s, H-27), 3.56 (1H, d, J = 8.4 Hz, H -28), 3.94 (1H, d, J = 8.4 Hz,
a
H -28), 0.93 (3H, s, H-29), 0.86 (3H, s, H-30), 4.88 (1H, d, J = 8.0, H-1′), 4.15 (1H, H-0032′), 4.23
b
(
4
1H, t, J = 9.0 Hz, H-3′), 4.41 (1H, t, J = 9.0 Hz, H-4′), 4.50 (1H, H-5′), 5.20 (1H, d, J = 8.0 Hz, H-1″),
.66 (1H, dd, J = 8.0, 9.0 Hz, H-2″), 4.20 (1H, dd, J = 2.5, 9.0 Hz, H-3″), 4.37 (1H, br d, J = 2.5 Hz,
H-4″), 4.12 (1H, m, H-5″), 4.50 (1H, H -6″), 4.30 (1H, H -6″), 6.25 (1H, br s, H-1″′), 4.76 (1H, br d,
a
b
J = 2.5 Hz, H-2″′), 4.88 (1H, dd, J = 2.0, 9.0 Hz, H-3″′), 4.16 (1H, H-4″′), 5.04 (1H, m, H-5″′), 1.45
3H, d, J = 6.0 Hz, H-6″′), 5.96 (1H, br s, H-1″″), 4.84 (1H, dd, J = 0.5, 3.0 Hz, H-2″″), 4.58 (1H, dd,
J = 3.0, 9.0 Hz, H-3″″), 4.30 (1H, H-4″″), 4.55 (1H, dd, J = 6.0, 9.0 Hz, H-5″″) and 1.68 (3H, d,
(
1
3
J = 6.0 Hz, H-6″″); C NMR (pyridine-d , 150 MHz): δ 39.5 (C-1), 27.2 (C-2), 89.6 (C-3), 40.2
5
C
(
8
(
C-4), 56.0 (C-5), 18.3 (C-6), 34.5 (C-7), 43.5 (C-8), 50.7 (C-9), 37.3 (C-10), 19.5 (C-11), 32.4 (C-12),
6.9 (C-13), 50.5 (C-14), 46.4 (C-15), 213.7 (C-16), 56.8 (C-17), 55.3 (C-18), 40.7 (C-19), 32.5
C-20), 36.3 (C-21), 25.7 (C-22), 28.7 (C-23), 17.3 (C-24), 16.7 (C-25), 19.4 (C-26), 22.5 (C-27),
7
1
5.7 (C-28), 34.0 (C-29), 24.1 (C-30), 107.3 (C-1′), 74.3 (C-2′), 88.7 (C-3′), 72.7 (C-4′), 77.7 (C-5′),
74.5 (C-6′), 104.7 (C-1″), 75.8 (C-2″), 76.7 (C-3″), 71.2 (C-4″), 77.6 (C-5″), 62.6 (C-6″), 100.8
(
7
(
C-1″′), 79.2 (C-2″′), 71.9 (C-3″′), 75.2 (C-4″′), 68.9 (C-5″′), 19.0 (C-6″′), 104.5 (C-1″″), 72.6 (C-2″″),
+
3.2 (C-3″″), 74.6 (C-4″″), 70.9 (C-5″″) and 19.0 (C-6″″); HR-ESI-MS m/z 1109.5496 [M + Na]
+
calcd for C H NaO , 1109.5503).
54 86
22
Supplementary material
General experimental procedures, acid hydrolysis and sugar identification, cytotoxicity MTT assay, 1D
1
13
and 2D NMR spectra, and table of H and C NMR data for the new compound 1.
Disclosure statement
No potential conflict of interest was reported by the author.
Funding
This work was supported by Vietnam Academy of Science and Technology [grant number VAST.
ĐTCB 01/16-17], and the Priority Research Center Program [grant number 2009‒0093815] through
the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and
Technology, Republic of Korea.

6
L. B. VINH ET AL.
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of Caryocar glabrum. J Nat Prod. 69:196–205.
Bandaranayake WM. 2002. Bioactivities, bioactive compounds and chemical constituents of mangrove
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