Isolation of lignans and neolignans from Pouzolzia sanguinea with their cytotoxic activity
Cite this paper: Vietnam J. Chem., 2021, 59(2), 146-152
DOI: 10.1002/vjch.202000120
Article
Isolation of lignans and neolignans from Pouzolzia sanguinea with their
cytotoxic activity
Le Thi Hong Nhung1,2, Nguyen Thi Hoang Anh1,3, Bui Huu Tai1,4, Phan Van Kiem1,4*
1Graduate University of Science and Technology, Vietnam Academy of Science and Technology (VAST), 18
Hoang Quoc Viet, Cau Giay, Hanoi 10000, Viet Nam
2Faculty of Chemical Technology, Hanoi University of Industry, Bac Tu Liem, Hanoi 10000, Viet Nam
3Institute of Chemistry, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi 10000, Viet Nam
4Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Cau Giay, Hanoi 10000, Viet Nam
Submitted July 13, 2020; Accepted August 5, 2020
Abstract
One lignan (7′S,8′R,8S)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (1) together with four
neolignans (7α,8α)-dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside (2), (7α,8α)-dihydrodehydro-
diconiferyl alcohol 9′-O-β-D-glucopyranoside (3), icariside E3 (4), and icariside E5 (5) were isolated from Pouzolzia
sanguinea. Their chemical structures were elucidated by ESI-MS, NMR spectra, as well as in comparison with the data
reported in literature. At concentration of 30 µM, compounds 1-5 exhibited weak cytotoxic activity with cell viability
percentages ranging from 59.9±0.98 % to 84.2±0.98 % and from 77.7±0.81 % to 100.3±0.78 % on CAL27 (oral
adenosquamous carcinoma cell) and MDA-MB-321 (breast cancer cell) cell lines, respectively.
Keywords. Pouzolzia sanguinea, lignan, neolignan, cytotoxicity.
1. INTRODUCTION
2. MATERIALS AND METHODS
2.1. Plant materials
Pouzolzia species have been used to treat ulcers in
traditional medicinal remedy in several countries such
reports indicated that methanolic extract of P. indica
significantly exhibited anti-proliferative effect and
induced apoptotic process on NB4 and HT93A acute
Pouzolzia genus revealed the presence of norlignans,
prenylated isoflavones, triterpenes which have shown
previous report, several norlignans were identified
from aerial parts of P. sanguinea. Their chemical
structures were remarkable not only by the loss of one
carbon in lignan skeleton but also the presence of an
report the isolation and identification of one lignan
and four neoligans from P. sanguinea. Cytotoxic
effects of the isolated compounds were evaluated on
CAL27 and MDA-MB-231 cell lines using 3-(4,5-
dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
Plant materials were collected at Da Lat, Lam
Dong, Vietnam in March 2018. Plant taxonomy,
Pouzolzia sanguinea (Blume) Merr. was identified
by Dr. Nguyen The Cuong, Institute of Ecology
and Biological Resources, VAST. Voucher
specimen (NCCT0318) was kept at the Institute of
Ecology and Biological Resources, VAST.
2.2. General experimental procedures
The used characterization techniques are the same as
described elsewhere.[14]
2.3. Extraction and isolation
The dried powdered P. sanguinea sample (5.0 kg)
was ultrasonic extracted with MeOH for three times
to get MeOH extract (350g). The MeOH extract was
suspended with water and successively separated in
n-hexane, dichloromethane, and ethyl acetate to give
bromide (MTT) assay.
146 Wiley Online Library © 2021 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH
Vietnam Journal of Chemistry
Phan Van Kiem et al.
corresponding soluble fractions and water layer. volume of methanol) to give four fractions PSW1-
Ethyl acetate extract (34 g) was separated on a silica PSW4. Fraction PSW3 (8 g) was separated on a
gel column, eluting with gradient solvent system of silica gel column chromatography, eluting with
dichloromethane/MeOH (0-100
%
volume of dichloromethane/methanol/water (6/1/0.1, v/v/v) to
methanol) to give 6 fractions, PSE1-PSE6. Fraction give three fractions PSW3A- PSW3C. Fraction
PSE2 was chromatographed on a RP-18 column and PSW3B was purified by preparative HPLC using
eluted with MeOH/water (1/1, v/v) to give 3 isocratic mobile phase 21 % acetonitrile in water to
fractions, PSE2A-PSE2C. PSE2B was purified by give compounds 3 (8.4 mg, tR 39.6 min) and 2 (3.6
preparative HPLC using isocratic mobile phase 25 % mg, tR 42.2 min). Finally, fraction PSW3C was
acetonitrile in water to give compound 1 (4.6 mg, tR purified by preparative HPLC using isocratic mobile
49.2 min). Water layer was loaded on diaion HP-20 phase 18 % acetonitrile in water to obtain
column, washed with water, and then eluted with compounds 4 (10.6 mg, tR 40.3 min) and 5 (23.9 mg,
water/methanol (25 %, 50 %, 75 %, and 100 % tR 42.7 min).
Figure 1: Chemical structures of compounds 1-5
O-β-D-glucopyranoside
(2):
Pale
yellow
(7′S,8′R,8S)-4,4′-Dihydroxy-3,3′,5,5′-
tetramethoxy-7′,9-epoxylignan-9′-ol-7-one
(1):
[ ]
amorphous powder; -20.8 (c 0.1, MeOH); ESI-
1
[ ]
Yellow gum;
-11.4° (c 0.1, MeOH); ESI-MS: MS m/z 545 [M+Na]+; H-NMR (CD3OD, 500
1
13
m/z 435 [M+H]+; H-NMR (CD3OD, 500 MHz) δH MHz) and C-NMR (CD3OD, 125 MHz) data, see
7.41 (2H, s, H-2 and H-6), 4.30 (1H, m, H-8), 4.20 table 1.
(1H, dd, J = 8.0, 8.5 Hz, Ha-9), 4.27 (1H, dd, J = 4.5,
(7α,8α)-Dihydrodehydrodiconiferyl
alcohol
8.5 Hz, Hb-9), 6.75 (2H, s, H-2′ and H-6′), 4.67 (1H, 9′-O-β-D-glucopyranoside
(3):
Pale-yellow
d, J = 8.0 Hz, H-7′), 2.67 (1H, m, H-8′), 3.71 (1H,
dd, J = 4.5 and 11.5 Hz, Ha-9′), 3.67 (1H, dd, J =
4.5, 11.5 Hz, Hb-9′), 3.94 (6H, s, 3,5-OCH3), 3.88
[ ]
amorphous powder; -16.5 (c 0.1, MeOH); ESI-
MS m/z 545 [M+Na]+; 1H-NMR (CD3OD, 500 MHz)
and 13C-NMR (CD3OD, 125 MHz) data, see table 1.
13
(6H, s, 3′,5′-OCH3); C-NMR (CD3OD, 125 MHz)
Icariside E3 (4): Pale-yellow amorphous
δC 128.5 (C-1), 107.8 (C-2), 149.2 (C-3), 143.4 (C-
4), 149.2 (C-5), 107.8 (C-6), 200.3 (C-7), 50.2 (C-8),
71.6 (C-9), 132.9 (C-1′), 105.3 (C-2′), 149.3 (C-3′),
136.4 (C-4′), 149.3 (C-5′), 105.3 (C-6′), 85.5 (C-7′),
55.1 (C-8′), 61.4 (C-9′), 56.9 (3,5-OCH3), and 56.8
(3′,5′-OCH3).
[ ]
powder;
-33.7 (c 0.1, MeOH); ESI-MS m/z
547 [M+Na]+; H-NMR (CD3OD, 500 MHz) and
1
13C-NMR (CD3OD, 125 MHz) data, see table 2.
Icariside E5 (5): Pale-yellow amorphous powder;
[ ]
-26.1 (c 0.1, MeOH); ESI-MS m/z 545
[M+Na]+;1H-NMR (CD3OD, 500 MHz) and 13C-
(7α,8α)-Dihydrodehydrodiconiferyl alcohol 9-
NMR (CD3OD, 125 MHz) data, see table 2.
Vietnam Journal of Chemistry
Isolation of lignans and neolignans from…
Table 1: 1H- and 13C-NMR spectral data for compounds 2 and 3
2
3
No.
a,bδC
a,cδH (mult., J in Hz)
-
a,bδC
134.9
110.6
149.1
147.3
116.2
119.7
89.0
a,cδH (mult., J in Hz)
-
1
2
3
4
5
6
7
8
134.8
110.8
149.0
147.7
116.1
119.7
89.0
7.01 (d, 1.5)
6.97 (d, 2.0)
-
-
-
-
6.77 (d, 8.0)
6.89 (dd, 8.0, 1.5)
5.62 (d, 6.5)
3.67 (m)
6.78 (d, 8.0)
6.84 (dd, 8.0, 2.0)
5.51 (d, 6.5)
3.48 (m)
53.3
55.4
72.3
3.78 (dd, 10.0, 7.0)
4.23 (dd, 10.0, 5.0)
-
6.74 (br s)
-
65.0
3.78 (dd, 11.0, 7.0)
3.85 (dd, 11.0, 5.5)
-
6.77 (br s)
-
-
-
6.77 (br s)
2.70 (t, 7.5)
1.93 (m)
9
1′
2′
3′
4′
5′
6′
7′
8′
136.9
114.3
145.2
147.4
129.7
118.2
35.8
136.8
114.3
145.2
147.5
129.9
118.1
32.9
-
-
6.80 (br s)
2.64 (t, 7.5)
1.84 (m)
32.9
32.9
9′
62.2
3.59 (t, 6.5)
69.9
3.55 (m)/ 3.94 (m)
Glc
1′′
2′′
3′′
4′′
5′′
104.6
75.2
78.3
71.7
78.1
62.8
4.37 (d, 8.0)
3.24 (dd, 8.0, 9.0)
3.38 (t, 9.0)
3.35 (t, 9.0)
3.30 (m)
3.68 (dd, 12.0, 5.0)
3.86 (dd, 12.0, 2.5)
3.84 (s)
104.5
75.2
78.2
71.7
77.9
62.8
4.27 (d, 7.5)
3.22 (dd, 7.5, 9.0)
3.38 (t, 9.0)
3.31 (t, 9.0)
3.28 (m)
3.69 (dd, 11.5, 5.5)
3.88 (dd, 11.5, 2.5)
3.84 (s)
6′′
3-OCH3
3′-OCH3
56.5
56.8
56.4
56.8
3.87 (s)
3.87 (s)
Measured in a) CD3OD, b)125 MHz, c)500 MHz.
Figure 2: The key HMBC correlations of compounds 1-4
Vietnam Journal of Chemistry
Table 2: 1H- and 13C-NMR spectral data for compounds 4 and 5
Phan Van Kiem et al.
4
5
No.
1
2
3
4
a,bδC
133.3
a,cδH (mult., J in Hz)
-
a,bδC
a,cδH (mult., J in Hz)
-
133.2
113.8
148.4
145.4
115.7
122.6
39.2
113.7
148.4
145.3
115.6
122.6
39.2
6.57 (d, 1.5)
6.58 (d, 2.0)
-
-
-
-
5
6
6.59 (d, 8.0)
6.49 (dd, 8.0, 1.5)
2.99 (dd, 14.0, 5.0)
2.72 (dd, 14.0, 9.0)
3.99 (m)
3.68 (dd, 11.0, 5.0)
3.76 (dd, 11.0, 6.0)
-
6.59 (d, 8.0)
6.50 (d, 8.0, 2.0)
2.99 (dd, 14.0, 5.5)
2.74 (dd, 14.0, 8.5)
3.99 (m)
3.68 (dd, 11.5, 5.5)
3.78 (dd, 11.5, 2.5)
-
7
8
9
42.8
67.1
42.8
66.8
1′
2′
3′
4′
5′
6′
7′
8′
9′
140.3
111.8
153.1
143.6
138.5
120.4
33.1
135.4
109.2
153.5
145.0
139.0
119.2
131.5
129.7
63.7
6.73 (br s)
-
6.93 (d, 2.0)
-
-
-
-
-
6.73 (br s)
2.65 (t, 7.5)
1.83 (m)
6.95 (d, 2.0)
6.58 (d, 15.5)
6.32 (td, 6.0, 15.5)
4.24 (d, 6.0)
35.5
62.2
3.57 (t, 6.5)
Glc
1′′
2′′
3′′
4′′
5′′
105.6
75.9
77.9
71.3
78.1
62.5
4.63 (d, 7.5)
3.47 (dd, 7.5, 9.0)
3.42 (t, 9.0)
3.39 (t, 9.0)
3.14 (m)
3.69 (dd, 11.5, 5.0)
3.80 (dd, 11.5, 2.5)
3.84 (s)
105.4
76.0
77.9
71.3
78.1
62.5
4.70 (d, 7.5)
3.48 (dd, 7.5, 9.0)
3.43 (t, 9.0)
3.39 (t, 9.0)
3.15 (m)
3.69 (dd, 11.5, 5.5)
3.79 (dd, 11.5, 2.5)
3.85 (s)
6′′
3-OCH3
3′-OCH3
56.4
56.3
56.4
56.3
3.71 (s)
3.71 (s)
Measured in a) CD3OD, b)125 MHz, c)500 MHz.
3. RESULTS AND DISCUSSION
(each 2C)], and two aliphatic methine groups (δC
55.1 and 50.2). Appearance of two pair of aromatic
1
Compound 1 was isolated as a yellow gum. The H- protons (δH 7.41 and 6.75) and four pair of aromatic
NMR and HSQC spectra of 1 showed proton signals carbons (δC 149.3, 149.2, 107.8, 105.3) magnetically
corresponding to four aromatic protons [δH 7.41 and equivalent indicated the presence of two symmetric
6.75 (each, 2H, s)], four methyl groups [δH 3.94 and 1,3,4,5-tetrasubtitited benzene rings. The HMBC
3.88 (each, 3H, s)], one oxygenated methine group correlations between H2-9 (δH 4.27 and 4.20) and C-
[δH 4.67 (1H, d, J = 8.0 Hz)], two oxygenated 8′ (δC 55.1)/C-8 (δC 50.2)/C-7′ (δC 85.5), H-7′ (δH
methylene groups [δH 4.27 (1H, dd, J = 4.5, 8.5 Hz) 4.67) and C-8′/C-8 /C-9 (δC 71.6) demonstrated the
and 4.20 (1H, dd, J = 8.0, 8.5 Hz), 3.71 and 3.67 presence of tetrahydrofuran ring (C-ring, figures 1
(each 1H, dd, J = 4.5, 11.5 Hz)], and two aliphatic and 2). Next, HMBC correlations between H-2′/H-6′
methine groups [δH 4.30 and 2.67 (each, 1H, m)]. (δH 6.75) and C-4′ (δC 136.4), methoxy protons (δH
The 13C-NMR and HSQC spectra of 1 showed 3.88) and C-3′/C-5′ (δC 149.3) supported assignment
signals of 22 carbons including one carbonyl group of the first 4′-hydroxy-3′,5′-dimethoxyphenyl group
(δC 200.3), twelve aromatic carbons (δC (A-benzene ring). Furthermore, HMBC correlations
105.3~149.3), one oxygenated methine group (δC between H-2′/H-6′ (δH 6.75) and C-7′ (δC 85.5)
85.5), two oxygenated methylene groups (δC 71.6 indicated this 4′-hydroxy-3′,5′-dimethoxyphenyl
and 61.4), four methoxy groups [δC 56.9 and 56.8 connect to tetrahydrofuran ring at C-7′. Carbon
Vietnam Journal of Chemistry
Isolation of lignans and neolignans from…
chemical shift value of C-9′ (δC 61.4), HMBC group linked to C-1′. HMBC correlations between
correlations between H2-9′ (δH 3.71 and 3.67) and C- H-6′ (δH 6.80) and C-8 (δC 53.3)/C-4′ (δC 147.4), H-7
7′ (δC 85.5)/C-8′ (δC 55.1)/C-8 (δC 50.2) suggested (δH 5.62)/H-8 (δH 3.67) and C-5′ (δC 129.7)/C-4′ (δC
hydroxymethylene group was at C-8′. Second 147.4) established benzofuran moiety (A and C
benzene ring moiety (B-benzene ring) was deduced rings, Fig. 1). Other benzene ring (B-ring) was
to be 4-hydroxy-3,5-dimethoxybenzoyl group which established to be 3-methoxy-4-hydroxyphenyl group
was confirmed by HMBC correlations between which was supported by HMBC correlations
H-2/H-6 (δH 7.41) and C-4 (δC 143.4)/C-7 (δC between H-2 (δH 7.01)/H-6 (δH 6.89) and C-4 (δC
200.3), between methoxy protons (δH 3.94) and C- 147.7), H-5 (δH 6.77)/3-OCH3 (δH 3.84) and C-3 (δC
3/C-5 (δC 149.2). Additionally, HMBC correlations 149.0). Furthermore, HMBC correlations between
between H-8′ (δH 2.67)/H-8 (δH 4.30)/H2-9 (δH 4.27 H-2/H-6 and C-7 (δC 89.0) indicated 3-methoxy-4-
and 4.20) and C-7 (δC 200.3) indicated 4-hydroxy- hydroxyphenyl group connect to C-7 of benzofuran
3,5-dimethoxybenzoyl
group
connected
to moiety. Other methoxy group at C-3′ was also
tetrahydrofuran ring at C-8 to form a lignan confirmed by HMBC correlations between 3′-OCH3
backbone. Due to containing three chiral centers (C- (δH 3.87)/ H-2′ (δH 6.74) and C-3′ (δC 145.2). HMBC
7′, C-8′, and C-8) relative configurations at those correlations between H2-9 (δH 4.23 and 3.78) and C-
centers were examined by analysis of NOESY 7 (δC 89.0)/ C-8 (δC 53.3)/C-5′ (δC 129.7)/Glc C-1″
spectrum. NOESY correlations between H2-9′ (δH (δC 104.6) proved O-glucosidic linkage at C-9. The
3.71 and 3.67) and H-7′ (δH 4.67)/H-8 (δH 4.30) sugar linkage must be in the β-form identified by glc
indicated the close proximity of hydroxymethylene JH-1/H-2 = 7.5 Hz. Relative configurations at C-7 and
group (C-9′), H-7′, and H-8 as described in figure 1. C-8 were deduced to be 7α and 8α, respectively, by
Finally, absolute configurations at C-7′, C-8′, and C- comparison their carbon chemical shifts (δC-7 89.0
8 was determined to be 7′S, 8′R, and 8S by negative and δC-8 53.3) with that reported in the literature
optical rotation [-11.4° (c 0.1, MeOH)] compared to (relative 7α,8α isomer[9]: δC-7 89.0 and δC-8 53.3),
previous
literature
Furthermore, the ESI mass spectrum of 1 exhibited an ion peak at m/z 545 [M+Na]+, corresponding to
an ion peak at m/z 435 [M+H]+, corresponding to the the molecular formula of C26H34O11. Consequently,
molecular formula of C22H26O9. Thus, compound 1 compound
was determined to be (7′S,8′R,8S)-4,4′-dihydroxy- dihydrodehydrodiconiferyl
2
was determined as (7α,8α)-
alcohol 9-O-β-D-
3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one.
glucopyranoside.
Compound 2 was isolated as pale-yellow amorphous
The 1H- and 13C-NMR data of compound 3 were
1
powder. The H-NMR spectrum of 2 contained found very similar with compound 2, except signals
signals corresponding to an ABX coupled spin of two oxygenated methylene groups [δC 65.0 (C-9)
system [δH 7.01 (1H, d, J = 1.5 Hz), 6.89 (1H, dd, J and 69.9 (C-9′), table 1]. HMBC correlations
= 1.5, 8.0 Hz), 6.77 (1H, d, J = 8.0 Hz)], an AX between H-7 (δH 5.51) and C-9 (δC 65.0), H2-7′ (δH
coupled spin system [δH 6.80 and 6.74 (each 1H, br 2.70) and C-9′ (δC 69.9) confirmed assignments of
s)], an anomeric proton [δH 4.37 (1H, d, J = 8.0 Hz)], C-9 and C-9′ at chemical shift values of δC 65.0 and
an oxygenated methine group (δH 5.62 (1H, d, J = δC 69.9, respectively. Therefore, in compound 3,
6.5 Hz)], and two methoxy groups (δH 3.87 and 3.84 upfield movement at carbon chemical shift of C-9
13
(each 3H, s)]. The C-NMR spectrum of 2 showed (δC 65.0) demonstrated a hydroxy group at C-9
signals corresponding to 26 carbon atoms. Among meanwhile downfield movement at carbon chemical
them, six oxygenated carbons (δC 104.6, 78.3, 78.1, shift of C-9′ (δC 69.9) suggested O-glucopyranosyl
75.2, 71.7, 62.8) and J value of anomeric proton (δH group at C-9′. The presence of O-glucopyranosyl
4.37, d, J = 8.0 Hz) were assigned for a β-D- group at C-9′ was also confirmed by HMBC
glucopyranosyl group. The presence of two methoxy correlations between Glc H-1″ (δH 4.27) and C-9′ (δC
groups was agreed by two carbon signals at δC 56.8 69.9), H2-9′ (δH 3.55 and 3.94) and Glc C-1″ (δC
and 56.4. Additionally, three sp3-hybridized carbon 104.5). Carbon chemical shift values at C-7 (δC 89.0)
atoms [δC 62.2 (C-9′), 32.9 (C-8′), 35.8 (C-7′)] and and C-8 (δC 55.4) indicated 7α,8α relative
their bearing protons [δH 3.59 (t, J = 6.5 Hz, H2-9′), configurations as shown in compound 2. The
1.84 (m, H2-8′), 2.64 (t, J = 7.5 Hz, H2-7′), coupling constant (J = 7.5 Hz) observed for the
1
respectively] suggested the presence of 3- anomeric proton in the H-NMR spectrum indicated
hydroxypropyl group. The HMBC correlations the β-glucoside linkage of the O-glucose moiety.
between H2-7′ (δH 2.64) and C-1′ (δC 136.9)/ C-2′ (δC Furthermore, the ESI mass spectrum of 3 exhibited
114.3)/ C-6′ (δC 118.2) indicated this hydroxypropyl an ion peak at m/z 545 [M+Na]+, corresponding to
Vietnam Journal of Chemistry
Phan Van Kiem et al.
the molecular formula of C26H34O11. Therefore, lines, respectively (table 3). Because of cell viability
compound was determined as (7α,8α)- percentages all over 50 % in the presence of
3
dihydrodehydrodiconiferyl
alcohol
9′-O-β-D- compounds 1-5 (30 µM), further cytotoxic study was
glucopyranoside.
not investigated as well as dose-dependent study.
Compound 4 was isolated as pale-yellow
amorphous powder. The 1H-NMR and HSQC
spectra of 4 showed an ABX coupled spin system
[δH 6.59 (1H, d, J = 8.0 Hz), 6.57 (1H, d, J = 1.5
Hz), 6.49 (1H, dd, J = 1.5, 8.0 Hz)], an AX coupled
spin system [δH 6.73 (2H, overlapped, br s)], an
anomeric proton [δH 4.63 (1H, d, J = 7.5 Hz)], and
two methoxy groups [δH 3.84 and 3.71 (each 3H, s)].
Different with 1H-NMR spectra of compounds 2 and
3, a doublet oxygenated methine signal was not
Table 3: Cytotoxic activity of 1-5 (30 µM)
Cell viability (%)
Compound
CAL27
MDA-MB-231
100.3±0.78
91.4±1.14
84.2±0.98
78.2±0.88
71.8±0.88
59.9±0.98
65.8±1.03
1
2
3
4
5
77.7±0.81
97.0±0.93
91.1±0.81
1
observed in the H-NMR of 4, suggesting the
Acknowledgment. This research is funded by
Graduate University of Science and Technology,
Vietnam Academy of Science and Technology under
grant number: GUST.STS.ĐT2019/HH03.
absence of furan ring. Additionally, carbon signal of
C-7 (δC 39.2), its bearing protons (δH 2.99 and 2.72),
HMBC correlations between H-2 (δH 6.57)/H-6 (δH
6.49) and C-7 indicating oxygenated methine group
(C-7) in compounds 2-3 was replaced by methylene
group in compound 4. Carbon chemical shift values
of C-9 (δC 67.1) and C-9′ (δC 62.2) indicated the
presence of hydroxy group at C-9 and C-9′,
respectively. HMBC correlations between H-2′ / H-
6′ (δH 6.73)/Glc H-1″ (δH 4.63) and C-4′ (δC 143.6)
indicated that O-glucopyranosyl group connect to C-
4′. The sugar linkage must be in the β-form indicated
by glc JH-1/H-2 = 7.5 Hz. Furthermore, the ESI mass
spectrum of 4 exhibited an ion peak at m/z 547
[M+Na]+, corresponding to the molecular formula of
C26H36O11. Thus, compound 4 was determined to be
icariside E3 as previously reported by Sadhu and co-
authors (table 2).[11]
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1
were similar with compound
4
except the
appearance of vinyl group (-CH=CH-) instead of
ethylene group (-CH2-CH2-). The presence of vinyl
group at C-7′/C-8′ was also agreed with doublet
signals of methylene proton H2-9′. Furthermore,
value of J coupling constant between H-7′ and H-8′
(J = 15.5 Hz) indicated geometric configuration of
double bond at C-7′/C-8′ to be E-configuration.
Furthermore, the ESI mass spectrum of 5 exhibited
an ion peak at m/z 545 [M+Na]+, corresponding to
the molecular formula of C26H34O11. Consequently,
compound 5 was determined to be icariside E5 as
previously reported by Lee and co-authors (table
2).[12]
Compounds 1-5 were evaluated their cytotoxic
effects on CAL27 and MDA-MB-231 cells using
compounds 1-5 exhibited weak cytotoxic activity
with cell viability percentages ranging from
59.9±0.98 % to 84.2±0.98 % and from 77.7±0.81 %
to 100.3±0.78 % on CAL27 and MDA-MB-321 cell
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Corresponding author: Phan Van Kiem
Institute of Marine Biochemistry
Vietnam Academy of Science and Technology
18 Hoang Quoc Viet, Cau Giay, Hanoi 10000, Viet Nam
E-mail: phankiem@yahoo.com.
7 trang
18/04/2022
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