New lignan glycosides from the stems of Securidaca inappendiculata Hassk

Article abstract of DOI:10.1016/j.phytol.2019.03.011

Three new lignan glycosides, (7R,8S)-4-hydroxy-3,5′-dimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-diol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (1), (7S,8R)-4-hydroxy-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-diol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (2) and (7S,7′S,8R,8′R)-4,4′-dihydroxy-3,5,3′,5′-tetramethoxy-7,9′:7′,9-diepoxylignane-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (3) were isolated from the stems of Securidaca inappendiculata Hassk. Their structures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR, HRESIMS, CD and chemical evidence. The MTT assay showed that compounds 1-3 exhibited moderate hepatoprotective activities against acetaminophen-induced HepG2 cell injury at respective 10 μM concentrations (Bicyclol as positive contrast).

Full text of DOI:10.1016/j.phytol.2019.03.011

Phytochemistry Letters 31 (2019) 58–62
Contents lists available at ScienceDirect
Phytochemistry Letters
journal homepage: www.elsevier.com/locate/phytol
New lignan glycosides from the stems of Securidaca inappendiculata Hassk
⁎
⁎
Junyang Ji, Qiwen Wang, Maolin Wang, Jianwei Chen , Xiang Li
College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210023, China
A R T I C L E I N F O
A B S T R A C T
Keywords:
Three new lignan glycosides, (7R,8S)-4-hydroxy-3,5′-dimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-diol-4-O-β-D-glu-
copyranosyl-(1→4)-β-D-glucopyranoside (1), (7S,8R)-4-hydroxy-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neoligna-
Securidaca inappendiculata Hassk
Polygalaceae
9
,9′-diol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (2) and (7S,7′S,8R,8′R)-4,4′-dihydroxy-3,5,3′,5′-
Lignan glycoside
Hepatoprotective
tetramethoxy-7,9′:7′,9-diepoxylignane-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (3) were isolated
from the stems of Securidaca inappendiculata Hassk. Their structures were elucidated on the basis of spectroscopic
analyses, including 1D and 2D NMR, HRESIMS, CD and chemical evidence. The MTT assay showed that com-
pounds 1-3 exhibited moderate hepatoprotective activities against acetaminophen-induced HepG2 cell injury at
respective 10 μM concentrations (Bicyclol as positive contrast).
1
. Introduction
Securidaca inappendiculata Hassk belongs to the genus Securidaca
All these signals with corresponding 1H-NMR signals were similar to
those of cedrusinin-4-O-α-L-rhamnopyranoside (He et al., 2012), which
indicated that the aglycone of 1 was 4-hydroxy-3,5′-dimethoxy-4′,7-
Linn. and grows mainly in tropical and subtropical areas. Previous
phytochemical investigations have led to the isolation of xanthones,
terpenes, steroids, lignans (Kang et al., 2009). This plant is a kind of
ethnic medicine in China which is used to promote blood circulation for
removing blood stasis. Modern pharmacological studies have proved
that Securidaca inappendiculata Hassk possesses anti-tumor, anti-in-
flammatory and hepatoprotective activities (Yang et al., 2001; Zhang
et al., 2005). At the current research, three new lignan glycosides (1-3)
were obtained from the stems of Securidaca inappendiculata Hassk. Their
structures were elucidated on the basis of spectroscopic data analyses
epoxy-8,3′-neoligna-9,9′-diol. Besides, signals at
δ
H
4.99 (1H, d,
J = 7.5 Hz) with δ
C
100.0 and δ
H
4.32 (1H, d, J = 7.5 Hz) with δ 103.6
C
suggested that 1 had two D-glucopyranosyl units which was proved by
acid hydrolysis of 1, and both of the D-glucopyranosyl units were of β
configuration deduced by the coupling constants of two anomeric
protons. The HMBC correlation from the anomeric proton signal of
Glucose A moiety at δ
H
4.99 (d, J = 7.5 Hz) to the carbon signal at δ
C
146.3 (C-4) indicated that Glucose A moiety was attached at C-4. The
carbon signals of Glucose A from C-1 to C-6 were δ 100.0, 73.4, 75.4,
1 1
C
80.2, 75.6, 60.4 respectively deduced by HSQC and H- H COSY ex-
periments. The terminal Glucose B moiety was speculated to attach at
C-4-Glc A with an oxygen bridge from analysis of the Glucose B moiety
(
1D and 2D NMR, HRESIMS, CD) and chemical evidence. All the
compounds were evaluated for their hepatoprotective activities against
acetaminophen-induced HepG2 cell injury (Bicyclol as positive con-
trast). Herein, the isolation, structural identification and hepatopro-
tective activities of these compounds were displayed.
at δ
H
4.32 (d, J = 7.5 Hz) to the carbon resonance at δ 80.2 (C-4-Glc
C
A). The relative configuration of 1 was supposed to be trans by the
coupling constant of H-7 (J = 5.5 Hz) (Wu et al., 2012). The CD spec-
trum of 1 showed a negative Cotton effect at 278 nm, which revealed its
absolute configuration to be 7R,8S (Hideaki et al., 1996). Therefore, 1
was determined as (7R,8S)-4-hydroxy-3,5′-dimethoxy-4′,7-epoxy-8,3′-
neoligna-9,9′-diol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside
(Figs. 1–4).
2
. Results and discussions
Compound 1 was obtained as a yellow amorphous transparent solid.
The HR-ESI-MS gave a pseudomolecular ion peak at m/z 707.2530
+
[
M + Na] , corresponding to the molecular formula C32
H
44
O
16 (cal-
Compound 2 was obtained as a yellow amorphous solid. The HR-
1
3
+
culated for C32
H
44
O
16Na, 707.2527). In the C-NMR spectrum of 1
ESI-MS gave a pseudomolecular ion peak at m/z 737.2641 [M + Na]
,
(
Table 1), 18 signals for 12 aromatic carbons at δ
C
149.4, 146.3, 145.9,
corresponding to the molecular formula C33
H
46
O
17 (calculated for
17Na, 737.2633). The C-NMR spectrum of 2 (Table 1) was
very similar to that of 1. By comparing the 1D and 2D NMR spectra of 1
1
3
1
43.8, 136.1, 135.7, 129.2, 118.3, 116.9, 115.7, 112.9, 110.7, and 6
C
33
H O
46
aliphatic carbons at δ
C
87.0, 63.5, 60.7, 54.0, 35.1, 32.0 were observed.
⁎
Corresponding authors at: College of Pharmacy, Nanjing University of Chinese Medicine, No.138, Xianlin Avenue, Qixia District, Nanjing, 210023, China.
E-mail addresses: chenjw695@126.com (J. Chen), lixiang_8182@163.com (X. Li).
https://doi.org/10.1016/j.phytol.2019.03.011
Received 22 November 2018; Received in revised form 15 February 2019; Accepted 14 March 2019
1874-3900/ © 2019 Published by Elsevier Ltd on behalf of Phytochemical Society of Europe.

J. Ji, et al.
Phytochemistry Letters 31 (2019) 58–62
Table. 1
NMR of compounds 1-3. (500 MHz for 1H-NMR, 125 MHz for 13C-NMR, DMSO-d
6
).
Position
1
2
3
δ
C
δ
H
δ
C
δ
H
δ
C
δ
H
1
2
3
4
5
6
7
8
9
136.1
110.7
149.4
146.3
115.7
118.3
87.0
137.8
104.5
153.1
134.3
153.1
104.5
87.2
137.8
104.6
153.1
134.0
153.1
104.6
85.5
6.99 (br s, 1 H)
6.70 (br s, 1 H)
6.66 (br s, 1 H)
7.08 (d, J = 8.0 Hz, 1 H)
6.86 (br d, J = 8.0 Hz, 1 H)
5.49 (d, J = 5.5 Hz, 1 H)
3.42 (m, 1 H)
6.70 (br s, 1 H)
6.66 (br s, 1 H)
5.47 (dd, J = 6.5, 2.5 Hz, 1 H)
3.47 (m, 1 H)
4.67 (d, J = 4.0 Hz, 1 H)
3.07 (m, 1 H)
54.0
53.7
54.1
63.5
3.61 (m, 1 H)
63.5
3.64 (m, 1 H)
71.7
3.80 (m, 1 H)
3
.72 (m, 1 H)
3.74 (m, 1 H)
4.18 (t, J = 6.8 Hz, 1 H)
1
2
3
4
5
6
7
8
9
'
'
'
'
'
'
'
'
'
135.7
116.9
129.2
145.9
143.8
112.9
32.0
135.8
116.9
129.3
145.9
143.9
113.0
32.0
131.8
104.1
148.4
135.3
148.4
104.1
85.8
6.70 (br s, 1 H)
6.70 (br s, 1 H)
6.60 (br s, 1 H)
6.70 (br s, 1 H)
2.54 (m, 2 H)
1.69 (m, 2 H)
3.42 (m, 2 H)
6.70 (br s, 1 H)
2.54 (m, 2 H)
1.70 (m, 2 H)
3.42 (m, 2 H)
6.60 (br s, 1 H)
4.62 (d, J = 4.4 Hz, 1 H)
3.07 (m, 1 H)
35.1
35.2
54.1
60.7
60.6
71.6
3.80 (m, 1 H)
4
.18 (t, J = 6.8 Hz, 1 H)
3
3
5
5
-OCH
3
3
3
3
56.1
3.76 (s, 3 H)
56.9
3.75 (s, 3 H)
56.9
56.5
56.9
56.5
3.76 (s, 3 H)
3.75 (s, 3 H)
3.76 (s, 3 H)
3.75 (s, 3 H)
'-OCH
-OCH
56.9
56.2
3.75 (s, 3 H)
3.78 (s, 3 H)
'-OCH
56.1
3.78 (s, 3 H)
Glucose A
1
2
3
4
5
6
100.0
73.4
75.4
80.2
75.6
60.4
4.99 (d, J = 7.5 Hz, 1 H)
3.34 (m, 1 H)
102.7
74.2
75.2
80.7
75.4
60.8
4.97 (d, J = 7.5 Hz, 1 H)
3.31 (m, 1 H)
102.8
74.3
75.3
80.9
75.5
60.9
4.94 (dd, J = 7.2, 1.6 Hz, 1 H)
3.29 (m, 1 H)
3.46 (m, 1 H)
3.40 (m, 1 H)
3.38 (m, 1 H)
3.44 (m, 1 H)
3.46 (m, 1 H)
3.44 (m, 1 H)
3.46 (m, 1 H)
3.24 (m, 1 H)
3.24 (m, 1 H)
3.64 (m, 2 H)
3.59 (m, 1 H)
3.58 (m,1 H)
3
.64 (m, 1 H)
3.64 (m, 1 H)
Glucose B
1
2
3
4
5
6
103.6
73.7
76.9
70.5
77.2
61.5
4.32 (d, J = 7.5 Hz, 1 H)
3.04 (m, 1 H)
103.5
73.7
77.0
70.6
77.3
61.5
4.30 (d, J = 8.0 Hz, 1 H)
3.02 (m, 1 H)
103.6
73.8
76.9
70.5
77.3
61.5
4.29 (d, J = 7.6 Hz, 1 H)
2.99 (m, 1 H)
3.19 (m, 1 H)
3.19 (m, 1 H)
3.17 (m, 1 H)
3.09 (m, 1 H)
3.08 (m, 1 H)
3.05 (m, 1 H)
3.21 (m, 1 H)
3.21 (m, 1 H)
3.20 (m, 1 H)
3.44 (m, 1 H)
3.43 (m, 1 H)
3.42 (m, 1 H)
3
.72 (m, 1 H)
3.71 (m, 1 H)
3.71 (m, 1 H)
Fig. 1. The structure of compound 1.
with those of 2, it could be deduced that 2 possessed one more meth-
oxyl at C-5 than 1. Acid hydrolysis of 2 suggested two D-glucopyranosyl
units and same as 1, both of the D-glucopyranosyl units were of β
configuration, the Glucose A moiety was attached at C-4, the Glucose B
moiety was attached at C-4-Glc A. The relative configuration of 2 was
supposed to be trans by the coupling constant of H-7 (J = 6.5 Hz). The
CD spectrum of 2 showed a positive Cotton effect at 278 nm, which
revealed its absolute configuration to be 7S,8R. Therefore, 2 was de-
termined as (7S,8R)-4-hydroxy-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neo-
ligna-9,9′-diol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside
C
34
at δ
H
46
H
O
18Na, 765.2576). In the NMR spectra of 3 (Table 1), the signals
6.66 (s, 2 H), δ 137.8, 104.6, 104.6, 153.1, 153.1, 134.0 and δ
6.60 (s, 2 H), δ 131.8, 104.1, 104.1, 148.4, 148.4, 135.3 indicated the
C
H
C
presence of two 1, 3, 4, 5-tetrasubstituted aromatic rings. The signals at
δ
C
85.5, 54.1, 71.7, 85.8, 54.1, 71.6 suggested the presence of a 2, 6-
1
diaryltetrahydrofuran ring system. In the H-NMR spectrum, four aro-
matic methoxyl signals at δ 3.75 (s, 6 H) and 3.76 (s, 6 H) were ob-
H
served. All these spectroscopic data of 3 was similar to that of syr-
ingaresinol. In addition, two anomeric protons and corresponding
carbons signals at δ
H
4.94 (dd, J = 7.2, 1.6 Hz, 1 H), δ
C
102.8 and δ
H
(
Figs. 2 and 5 ).
4.29 (d, J = 7.6 Hz, 1 H), δ 103.6 showed the presence of two D-glu-
C
Compound 3 was obtained as a white amorphous powder. The HR-
copyranosyl units which was identified by acid hydrolysis of 3, and
both of the D-glucopyranosyl units were of β configuration deduced by
the coupling constants of two anomeric protons. The HMBC correlation
+
ESI-MS gave a pseudomolecular ion peak at m/z 765.2538 [M + Na]
,
corresponding to the molecular formula C34
H O18 (calculated for
46
59

J. Ji, et al.
Phytochemistry Letters 31 (2019) 58–62
Fig. 2. The structure of compound 2.
Fig. 3. The structure of compound 3.
Fig. 4. Key 1H- H COSY and HMBC correlations of compound 1 (e H- H COSY →HMBC).
1
1
1
Fig. 5. Key 1H- H COSY and HMBC correlations of compound 2 (e H- H COSY →HMBC).
1
1
1
from the anomeric proton signal of Glucose A moiety at δ
H
4.94 (dd,
B moiety was speculated to attach at C-4-Glc A with an oxygen bridge
from analysis of the Glucose B moiety at δ 4.29 (d, J = 7.6 Hz) to the
J = 7.2, 1.6 Hz, 1 H) to the carbon signal at δ 134.0 (C-4) indicated
C
H
that Glucose A was attached at C-4. The carbon signals of Glucose A
carbon resonance at δ 80.9 (C-4-Glc A). The relative configuration of 3
C
from C-1 to C-6 were δ
C
102.8, 74.3, 75.3, 80.9, 75.5, 60.9 respectively
was deduced by ROESY spectrum. First, natural bistetrahydrofurans
1
1
deduced by HSQC and H- H COSY experiments. The terminal Glucose
exist in the form of cis. Second, no NOE effect could be seen between H-
60

J. Ji, et al.
Phytochemistry Letters 31 (2019) 58–62
Fig. 6. Key 1H- H COSY and HMBC correlations of compound 3 (e H- H COSY →HMBC).
1
1
1
3
. Experimental
3.1. General experimental procedures
1
13
H-NMR (500 MHz), C-NMR (125 MHz) and 2D NMR spectra were
obtained on Bruker AV-500 with TMS as internal reference. HR-ESI-MS
were acquired in the positive ion mode on a Q-TOF MS (Triple TOF
5
6
600+, AB Sciex, USA) and Q-TOF LC/MS (Agilent Technologies,
530, Accurate-Mass). UV spectra were recorded on a UV-VIS recording
spectrophotometer (UV-2401PC, Shimadzu). IR spectra were measured
on a Nicolet iS5 spectrometer. CD spectra were obtained on a J-810
Circular Dichroism spectrapolarimeter (JASCO, Japan). Optical rota-
tions were acquired on Autopol Ⅲ automatic polarimeter (Rudolph
Research Analytical). Suger analyses were performed on HPLC (Waters
Fig. 7. Key ROESY correlations of compound 3 (↔ROESY).
Alliance e2695) using NH column (5 μm, 4.6 mm × 250 mm, Hypersil)
2
7
and H-8, H-7′ and H-8′. The CD spectrum of 3 showed a positive
equipped with ELSD (Alltech 2000ES). Semi-preparative HPLC experi-
Cotton effect at 274 nm, which was same as (-)-syringaresinol (Liu
et al., 2013). Therefore, 3 was determined as (7S,7′S,8R,8′R)-4,4′-di-
hydroxy-3,5,3′,5′-tetramethoxy-7,9′:7′,9-diepoxylignane-4-O-β-D-glu-
copyranosyl-(1→4)-β-D-glucopyranoside (Figs. 3, 6 and 7 ).
In vitro hepatoprotective activities of the three compounds were
evaluated by MTT assay. The results (Table 2) suggested that all of the
three compounds showed moderate hepatoprotective activities com-
pared with bicyclol.
ments were performed on a Shimadzu LC-6AD equipped with a SPD-
2
0A detector (Shimadzu, Japan) using a SunFire C18 OBD Prep Column
(
5 μm, 10 mm × 250 mm, Waters, USA). Bicyclol (LOT:101044-
01001) and acetaminophen (LOT: 100018-201610) were obtained
from National Institutes for Food and Drug Control. Column chroma-
2
tography silica gel (SiO ; 200–300 mesh; Qingdao Haiyang Chemical
2
Co., Ltd., Qingdao, China); Macroporous resin (Yuanye Bio.); Sephadex
LH-20 (Pharmacia, GE). All other chemicals were of analytical reagent
grade.
Table. 2
Hepatoprotective activities of compounds 1-3.
3.2. Plant material
Groupa
Relative protection (%)b
The stems of Securidaca inappendiculata Hassk were collected in
December 2014 at Wenshan, Yunnan Province, China and identified by
Professor Jianwei Chen (College of Pharmacy, Nanjing University of
Chinese medicine, China). A voucher specimen of the plant (NO.
CYT20141224) was deposited in the Herbarium Center, Nanjing
University of Chinese Medicine, China.
Control
100.00 ± 4.28
*
**
#
Model
0.00 ± 1.63
##
#
Bicyclol
14.00 ± 1.83
11.37 ± 4.12
#
#
1
2
3
#
9.31 ± 4.31
#
8.64 ± 6.73
a
Acetaminophen (8 mM)-induced cells as the model
group; Bicyclol as the positive contrast; The compounds
were tested at 10 μM.
3
.3. Extraction and isolation
b
The dried stems of Securidaca inappendiculata Hassk (20 kg) were
Results are expressed as the means ± SD (n = 4).
extracted with 95% EtOH (90 L × 3, 2 h each) under condition of re-
flux. The EtOH extract (2688 g) was evaporated to dryness under re-
duced pressure. This extract was mixed with silica gel (100–200 mesh,
2.5 kg) and heated to dryness. Then it was partitioned with petroleum
*
** p ＜ 0.001 (vs control group).
#
#
#
##
#
p ＜ 0.001.
p ＜ 0.01.
p ＜ 0.05 (vs model group).
61

J. Ji, et al.
Phytochemistry Letters 31 (2019) 58–62
ether, CH
2
Cl
2
, EtOAc and MeOH respectively. The CH
2
Cl
2
fraction
(20 μM) were added and the cells were cultured for 2 h. Then, fresh
media (100 μL) containing APAP (16 mM) were added to the cultured
cells. The culture supernatant was discarded, and 100 μL of the 0.5 mg/
mL MTT was added to the cells and maintained for 4 h after culturing
for 48 h. The formazan was dissolved in DMSO (150 μL) after removal
of the MTT solution. The optical density (OD) of the formazan solution
was determined using a microplate reader at a wavelength of 570 nm.
Bicyclol was used as the positive contrast.
(
140 g), EtOAc fraction (277 g) and MeOH fraction (1261 g) are ob-
tained after the solution was evaporated. Part of the MeOH fraction
1125 g) was subjected to column chromatography using macroporous
resin with gradient mixtures of EtOH/H O (10%, 30%, 50%, 70%, 95%,
fraction A–E). Fracton B (105 g) was later separated on a silica gel
(
2
column with a gradient elution of CH
2
Cl /MeOH (100:1˜0:1) to afford
2
Fr.B1-Fr.B45. Fr.B14 was divided into twenty six parts (Fr.B14a-
Fr.B14z) by MPLC using C18, eluted by a increasing gradient of MeOH/
H
2
O (20%˜60%). The twenty-first part (Fr.B14 u) and the twenty-
3.5. Acid hydrolysis of 1-3
second part (Fr.B14v) were purified using semi-preparative HPLC to
afford 1 (90 mg, 35% MeOH/H O, t =13 min, flow rate=6.5 mL/min)
and 2 (80 mg, 37% MeOH/H O, t =15 min, flow rate=5 mL/min)
respectively. Fr.B9 was isolated into twenty-five parts (Fr.B9a-Fr.B9y)
using MPLC, eluted by a increasing gradient of MeOH/H O (10%˜50%).
The twenty-first part (Fr.B9u) was subjected to column chromatography
over Sephadex LH-20 (50% MeOH/H O) to yield 3 (32 mg).
2
R
Compounds 1-3 (2 mg each) were heated with 2 mol/L TFA (2 mL)
2
R
for 3 h at 90 °C. The mixture was cooled and partitioned between
CH
2
Cl
2
(2 mL) and H O for 3 times. The aqueous layer was evaporated
2
2
under reduced pressure to 500 μL. Then the samples were analysed on
HPLC (85% CH CN/H O, flow rate=1 mL/min) equipped with ELSD
using NH
3
2
2
2
Column. At last, compare the retention time with those of
rhamnose, xylose, arabinose, mannose, glucose, galactose.
3
.3.1. (7R,8S)-4-hydroxy-3,5′-dimethoxy-4′,7-epoxy-8,3′-neoligna-9,9′-
diol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (1)
Conflict of interest
2
5
Yellow solid (MeOH); [ ] 65° (c 0.1, MeOH); [θ]278 -1.31; UV
D
(
MeOH) λmax (logε) 279 (3.54) nm; IR (KBr) νmax 3382, 2929, 1605,
The authors declare no conflict of interest.
Acknowledgements
−
1
1
13
1
514, 1452, 1421, 1325, 1266, 1213 cm
;
H and C NMR data
+
(
Table 1); (+)-HRESIMS m/z 707.2530 [M + Na] (calculated for
C
32
H O16Na at m/z 707.2527).
44
This work was financially supported by the National Natural Science
Foundation of China (81573577 and 81274057). Herein, I wish to ex-
press my sincere thanks.
3
.3.2. (7S,8R)-4-hydroxy-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neoligna-
9
,9′-diol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (2)
2
5
Yellow solid (MeOH); [ ] -65.3° (c 0.1, MeOH); [θ]278 +1.29; UV
D
(
MeOH) λmax (logε) 280 (3.37) nm; IR (KBr) νmax 3423, 2908, 1597,
Appendix A. Supplementary data
−
1
1
13
1
499, 1464, 1425, 1333, 1215, 1077 cm
;
H and C NMR data
+
(
Table 1); (+)-HRESIMS m/z 737.2641 [M + Na] (calculated for
Supplementary material related to this article can be found, in the
online version, at doi:https://doi.org/10.1016/j.phytol.2019.03.011.
C
33
H
46
O
17Na at m/z 737.2633).
3
.3.3. (7S,7′S,8R,8′R)-4,4′-dihydroxy-3,5,3′,5′-tetramethoxy-7,9′:7′,9-
References
diepoxylignane-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (3)
2
5
White powder (MeOH); [ ] -16.7° (c 0.1, MeOH); [θ]274 +4.94;
D
He, W., Fu, Z., Zeng, G., Zhang, Y., Han, H., Yan, H., Ji, C., Chu, H., Tan, N., 2012.
Terpene and lignan glycosides from the twigs and leaves of an endangered conifer,
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UV (MeOH) λmax (logε) 307 (2.76) nm; IR (KBr) νmax 3421, 2915, 1595,
−
1
1
13
1
509, 1463, 1425, 1330, 1234 cm
;
H and C NMR data (Table 1);
Hideaki, O., Naozumi, K., Kyomi, N., 1996. A neolignan glycoside and acylated iridoid
glucosides from stem bark of Alangium platanifolium. Phytochemistry 42,
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+
(
+)-HRESIMS m/z 765.2538 [M + Na] (calculated for C34
H
46
O
18Na
at m/z 765.2576).
.4. Hepatoprotective effect
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appendiculata. Chem. Pap. 63, 102–104.
3
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In vitro hepatoprotective activities of three compounds were eval-
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tivities from exocarp of Castanea henryi. Carbohyd. Res. 355, 45–49.
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uated by the MTT assay. HepG2 cells were cultured in DMEM media
with 10% fetal calf serum, penicillin (100 U/mL) and streptomycin
(
100 μg/mL) at 37 °C in a humidified atmosphere of 5% CO
2
. The cells
4
Zhang, L., Yang, X., Xu, L., Zou, Z., Yang, S., 2005. A new sterol glycoside from Securidaca
inappendiculata. J. Asian Nat. Prod. Res. 7, 649–653.
were seeded in 96-well culture plates at a density of 1 × 10 per well
with 200 μL culture media. After incubation for 24 h, the culture su-
pernatant was discarded, fresh media (100 μL) containing test samples
62