Two new furostanol saponins from the fibrous root of Ophiopogon japonicus

Article abstract of DOI:10.1080/10286020.2013.861822

Two new furostanol saponins ophiopogonins J (1) and K (2) were isolated from the fibrous roots of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-14-hydroxy-furost-5,20(22)-d

Full text of DOI:10.1080/10286020.2013.861822

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Two new furostanol saponins from the
fibrous root of Ophiopogon japonicus
a
b
c
c
Zhi-Yun Kang , Meng-Jia Zhang , Jian-Xin Wang , Jian-Xun Liu ,
c
a
Chang-Ling Duan & De-Quan Yu
a
Institute of Materia Medica, Chinese Academy of Medical
Sciences and Peking Union Medical College, Beijing, 100050, China
b
The Pharmacy of Qingdao Sanatorium of Shandong Province,
Qingdao, 266071, China
c
Xiyuan Hospital, China Academy of Chinese Medical Sciences,
Beijing, 100091, China
Published online: 12 Dec 2013.
To cite this article: Zhi-Yun Kang, Meng-Jia Zhang, Jian-Xin Wang, Jian-Xun Liu, Chang-Ling Duan
&
De-Quan Yu (2013) Two new furostanol saponins from the fibrous root of Ophiopogon japonicus,
Journal of Asian Natural Products Research, 15:12, 1230-1236, DOI: 10.1080/10286020.2013.861822
To link to this article: http://dx.doi.org/10.1080/10286020.2013.861822
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Journal of Asian Natural Products Research, 2013
Vol. 15, No. 12, 1230–1236, http://dx.doi.org/10.1080/10286020.2013.861822
Two new furostanol saponins from the fibrous root of
Ophiopogon japonicus
a1
b1
c
c
Zhi-Yun Kang , Meng-Jia Zhang , Jian-Xin Wang , Jian-Xun Liu , Chang-Ling Duan *
c
a
and De-Quan Yu *
a
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical
College, Beijing 100050, China; The Pharmacy of Qingdao Sanatorium of Shandong Province,
b
c
Qingdao 266071, China; Xiyuan Hospital, China Academy of Chinese Medical Sciences, Beijing
1
00091, China
(Received 28 October 2013; final version received 29 October 2013)
Two new furostanol saponins ophiopogonins J (1) and K (2) were isolated from the
fibrous roots of Ophiopogon japonicus. The structures of 1 and 2 were established as
(
5
(
25R)-26-O-[(b-D-glucopyranosyl-(1 ! 2)-b-D-glucopyranosyl)]-14-hydroxy-furost-
,20(22)-diene 3-O-[a-L-rhamnopyranosyl-(1 ! 2)]-b-D-glucopyranoside (1), and
25R)-26-O-[(b-D-glucopyranosyl-(1 ! 2)-b-D-glucopyranosyl)]-furost-5,20(22)-
diene 3-O-a-L-rhamnopyranosyl-(1 ! 2)[(b-D-xylopyranosyl-(1 ! 4)-b-D-glucopyr-
anoside)] (2) on the basis of spectroscopic means including HRESIMS, 1D, and 2D
NMR experiments.
Keywords: Ophiopogon japonicus; furostanol saponin; Liliaceae
1
.
Introduction
2. Results and discussion
Ophiopogon japonicus (Thunb.) Ker-
Gawl (Liliaceae), which is known as
Compound 1 was obtained as white
amorphous powder. Its specific rotation
2
0
‘
Maidong’ in China, is widely used in
½aꢀ (c 0.12, DMSO) was 283.0. The
D
traditional Chinese medicine for curing
cardiovascular and cerebrovascular dis-
eases as expectorant, antitussive, and
tonic agent, as well as treating acute and
chronic inflammatory diseases including
pharyngitis, bronchitis, pneumonia,
angina, cough, etc [1–3]. Chemical
studies have shown that this plant
includes saponins, homoisoflavonoids,
flavonoids, amides, and terpenoids [4–
HRESIMS of 1 showed pseudo-molecular
ion peaks at m/z 1085.5156 [M þ Na] ,
þ
2
1061.5232 [M–H] , which suggested the
molecular formula of C H O .
1 82 23
5
1
The H NMR spectrum of 1 showed
three proton singlets at d 0.96 (s, Me-18),
H
1.13 (s, Me-19), and 1.69 (s, Me-21),
indicating the presence of two angular
methyl groups and one tertiary methyl
group; a three-proton doublet at d 1.07 (d,
H
1
2] from O. japonicus. Our further
J ¼ 6.5 Hz, Me-27), assignable to one
secondary methyl group. Furthermore,
signals for an olefinic proton at dH 5.37
phytochemical investigation on fibrous
roots of O. japonicus led to the isolation
of two new furostanol saponins ophiopo-
gonins J (1) and K (2) (Figure 1). Herein,
we report the isolation and structural
determination of the new constituents.
(br. s), four anomeric protons at d 5.01 (d,
H
J ¼ 7.0 Hz), 6.37 (br. d, J ¼ 1.0 Hz), 4.86
(d, J ¼ 8.0 Hz), 5.29 (d, J ¼ 8.0 Hz), and
the methyl group of a 6-deoxyhexopyr-
*Corresponding authors. Email: 18001286206@163.com, DQyu@imm.ac.cn
q 2013 Taylor & Francis

Journal of Asian Natural Products Research
1231
HO
HO
O
O
HO
HO
HO
O
O
H
HO
OH
H
O
OH
HO
HO
O
O
H
HO
O
H
Me
HO
O
H
HO
OH
HO
HO
1
O
O
HO
HO
HO
O
O
H
HO
OH
H
O
HO
O
O
O
OH
O
HO
HO
HO
H
O
H
H
H
O
HO
HO
OH
2
Figure 1. Structures and key HMBC correlations of compounds 1 and 2.
anosyl moiety at dH 1.76 (d, J ¼ 6.0 Hz)
152.3 (C-22), 103.9 (C-20), 61.6 (C-17),
19.4 (C-19) and 17.2 (C-27) were assigned
1
3
were observed. The C NMR spectrum
showed 51 carbon signals in which the
signals at dC 140.8 (C-5), 122.3 (C-6),
1
3
readily. The C NMR spectral data of
aglycone were closely related to those of

1
232
Z.-Y. Kang et al.
L-rhamnopyranosyl-(1 ! 2)]-b-D-gluco-
pyranoside.
Compound 2 was obtained as white
pseudoprotodioscin [13,14], except for the
differences at C-12 (27.8 ppm), C-13
(
þ4.5 ppm), C-14 (þ29.9 ppm), and C-
2
0
amorphous powder, with ½aꢀ 272.1. Its
1
5 (þ6.6 ppm) in aglycone of 1, which are
D
ESIMS showed the pseudo-molecular ion
peaks at m/z 1201 [M þ Na] , 1177 [M–
suggestive of one hydroxy linking to C-14.
The existence of 14-hydroxy group was
further determined by long-range corre-
þ
2
H] , and the corresponding fragments at
þ
m/z 1069 [M þ Na-132] , 1045 [M–H-
lations between H-15 (d 2.45) and C-14
H
2
2
32] , 1015 [M–H-162] , 883 [M–H-
1
1
1
(
d 84.8), and H-18 (d 0.96) and C-14 (d
C H C
2
32-162] , and 733 [M–H-132-162-
2
46] . The molecular formula was
8
4.8) in the HMBC experiment. The
aglycone’s 25R configuration was deduced
from the difference in chemical shifts of
the geminal protons 2H-26 (da –
assigned as C H O on the basis of
5
6 90 26
þ
HRESIMS at m/z 1179.5756 [M þ H] ,
1
13
together with its H and C NMR spectral
data.
d ¼ 0.44 , 0.48) [15]. Thus, the agly-
b
cone of 1 was identified as (25R)-
3
1
For the aglycon moiety, the H NMR
b,14,26-triol-furost-5,20(22)-diene.
Acid hydrolysis of 1 gave glucose and
spectrum of 2 revealed the presence of
four typical steroid methyl groups at dH
rhamnose (3:1) as carbohydrate moieties.
The downfield shifts for C-3 and C-26 of
the aglycone (d 77.9 and 74.7) allowed
0
.74 (s, 3H), 1.04 (s, 3H), 1.66 (s, 3H),
and 1.06 (3H, d, J ¼ 6.5 Hz), and an
C
olefinic proton at d 5.27 (1H, br. s). The
H
the deduction that C-3 and C-26 were the
glycosyl sites. The sugar sequence of
rhamnosyl-(1 ! 2)-glucosyl and its link-
age at C-3 were determined by gHMBC
1
13
H and C NMR spectral data of aglycon
were basically consistent with those of
pseudoprotodiosgenin [13] and its struc-
ture was further determined on the basis
of extensive gHMQC, gHMBC, and
0
0
correlations between H-1 (d 6.37) and
H
0
0
C-2 (d 77.7) and between H-1 (d 5.01)
H
13
C
gCOSY spectral data. The C NMR
spectral data of sugar moieties were
and C-3 (d 77.9). The sugar sequence of
C
glucosyl-(1 ! 2)-glucosyl and its linkage
closely identical to those of compound 1
except the additional signals at d 105.8,
at C-26 were ascertained by long-range
correlations between H-1 (d 5.29) and
C
0
000
H
7
5.0, 78.4, 70.8, 67.4. Acid hydrolysis of
produced glucose, rhamnose, and
xylose in the ratio of 3:1:1. The sugar
0
00
000
C-2 (dC 84.1) and between H–1 (dH
.86) and C-26 (d 74.7). The proton and
2
4
C
carbon signals of the sugar moieties were
assigned by gHMQC, gHMBC, gCOSY
sequence of rhamnosyl-(1 ! 2)-[xylosyl-
(
were identified by gHMBC correlations
1 ! 4)]-glucosyl and its linkage at C-3
1
3
analyses and by comparison of the
C
NMR data with those in the literature [9].
The b-configuration of glucose was
determined by large J values of the
anomeric-H-atom signals at dH 5.01 (d,
00
0
between H-1 (dH 6.25) and C-2 (d
C
000
7
4
7.5), and between H-1 (d 5.02) and C-
H
0
0
(d 81.5), and between H-1 (d 4.96)
C
H
and C-3 (d 78.0). The b-configuration of
C
0
J ¼ 7.0 Hz, H–1 ), 4.86 (d, J ¼ 8.0 Hz,
glucose and the a-configuration of rham-
nose were determined according to the
method of compound 1. Therefore, the
structure of 2 was established as (25R)-
26-O-[(b-D-glucopyranosyl-(1 ! 2)-b-
D-glucopyranosyl)]-furost-5,20(22)-diene
3-O-a-L-rhamnopyranosyl-(1 ! 2) [(b-
D-xylopyranosyl-(1 ! 4))]-b-D-gluco-
pyranoside.
0
00
0000
H–1 ), 5.29 (d, J ¼ 8.0 Hz, H–1 ),
while the rhamnose had an a-configuration
evidenced by carbon signals of dC 72.8
(
C-3 of Rha) and dC 69.5 (C-5 of Rha)
16]. This way, the structure of 1 was
[
determined as (25R)-26-O-[(b-D-gluco-
pyranosyl-(1 ! 2)-b-D-glucopyranosyl)]-
1
4-hydroxy-furost-5,20(22)-diene 3-O-[a-

Journal of Asian Natural Products Research
1233
3
.
Experimental
herbarium of Peking University Modern
Research Center for Traditional Chinese
Medicine.
3
.1 General experimental procedures
JASCO P-2000 Digital Polarimeters
Jasco Co., Limited, Tokyo, Japan) were
(
used in Optical rotation values detection.
IR spectra were obtained from a Nicolet
3
.3 Extraction and isolation
The fibrous roots of O. japonicus (45 kg)
were extracted with EtOH (70%) under
reflux and then filtered by gauze. The
extract was concentrated under reduced
pressure and the residue was suspended in
5
700 spectrometer (Thermo Electron
Scientific Instruments Co., Miami, FL,
USA). NMR spectra were recorded on a
UNITYINOVA 500 spectrometer (Varian
Medical System Inc., Palo Alto, CA,
USA). and a JNM-ECA 400 spectrometer
H O and subsequently extracted succes-
2
sively with petroleum ether (60 , 908C),
EtOAc, and n-BuOH. The n-BuOH soluble
fraction was subjected to Diaion HP-20
resin CC eluted with 20% EtOH, 55%
(Jeol, Tokyo, Japan) with tetra-methyl
silane as internal standard. The HRESIMS
were carried out on Nano LC-Q-TOF (Q-
Star, AB Scix, Vaughan, Canada) and
APEX IV (7.0T) mass spectrometer
EtOH, and 80% EtOH in H O to afford
2
three fractions (Fr. 1 , 3). Fr. 2 (100.0 g)
was separated by silica gel CC (100–200
(Bruker Co., Boston, MA, USA). HPLC
was carried out on Agilent LC 1100 with
an UV detector (Agilent Technologies,
Santa Clara, CA, USA). GC analysis was
performed on an HP6890 plus instrument
mesh) eluted with CHCl :MeOH (1:0,
3
1
00:1, 50:1, 30:1, 15:1, 10:1, 5:1, 2:1, 0:1)
to give seven fractions (Fr. 2-1 , 7). Fr.
–6 (25 g) was subjected to silica gel
eluted with EtOAc:EtOH (20:1, 15:1, 10:1,
:1, 8:1, 6:1, 4:1) to afford Fr. 2-6-1 , 7.
2
(Agilent Technologies) equipped with an
H2 flame ionzation detector. The GC
analysis conditions were HP-5 quartz
capillary column (30 m £ 0.32 mm
9
Fr. 2-6-5 (5 g) was further separated on
octa-decylsilyl silicon silica gel column by
gradient MeOH–H O, and tubes (119–
£
0.25 mm); column temperature, 140–
2
2
408C; programmed oven temperature
increase, 108C/min; carrier gas, N2
1.5 ml/min); injector temperature,
408C; detector temperature, 2608C; injec-
1
27) were purified on Sephadex LH-20 CC
with MeOH as eluent to afford 1 (14 mg).
Fr. 2-6-6 (3 g) was purified on Sephadex
LH-20 CC with MeOH, and then by
repeated semi-preparative HPLC (Zorbax
XDB-C18 column, 9.4 mm £ 250 mm,
(
2
tion volume, 1 ml; split ratio, 1:50. Column
chromatography (CC) was performed over
silica gel (100–200 and 300–400 mesh,
Qingdao Marine Chemical Co. Ltd.,
Qingdao, China), Daion HP-20 polyporous
resin (Mitsubishi Chemical Co., Tokyo,
Japan), and Sephadex LH-20 gel (Amer-
sham Biosciences AB, Upsala, Sweden).
5
2
mm, MeOH:H O (62:38), flow rate
2
.0 ml/min, UV 203 nm) to yield 2
(29 mg).
3
.3.1 Ophiopogonin J (1)
2
0
White amorphous powder; ½aꢀ 283.0 (c
D
0
.123, DMSO); IR (KBr) n : 3395, 2934,
max
3
.2 Plant material
1695, 1642, 1453, 1378, 1063,1043, 913,
893.5 cm
2
1
1
13
H NMR and C NMR
The fibrous roots of Ophiopogon japonicus
were purchased from Anguo traditional
Chinese medicine market, Hebei Province,
China, in September 2005 and identified
by Prof. Peng-Fei Tu. A voucher specimen
;
spectral data (in C D N) (see Table 1).
5
5
þ
HRESIMS: m/z 1085.5156 [M þ Na]
(calcd for C H O Na, 1085.5145);
5
1
82 23
2
1061.5232 [M–H] (calcd for C H O ,
5
1 81 23
(MD20050906) has been deposited in the
1061.5169).

1
234
Z.-Y. Kang et al.
1 13
Table 1. H NMR (500 MHz) and C NMR (125 MHz) spectral data of 1 in pyridine-d5.
Position
d
C
H
d , J (Hz)
Position
d
C
H
d , J (Hz)
1
2
3
4
5
6
7
8
9
37.8
30.2
77.9
39.0
140.8
122.3
26.8
35.0
43.6
37.4
20.5
31.8
47.8
84.8
42.4
85.2
61.6
17.7
19.4
103.9
12.0
152.3
23.9
31.4
33.6
74.7
1.02 m, 1.79 m
1.90 m, 2.09 m
3.89 m
27
3-O-Glc 1
17.2
100.2
77.7
79.6
71.8
77.9
62.5
102.0
72.6
72.8
74.2
69.5
18.7
103.2
84.1
77.7
71.3
78.3
62.6
106.3
77.1
77.7
71.3
78.6
62.5
1.07 d, (6.5)
5.01 d, (7.0)
4.26 m
0
0
2
3
4
5
0
2.75 m, 2.80 m
4.25 m
4.18 m
3.88 m
0
0
0
5.37 br. S
1.85 m, 2.45 m
2.01 m
6
4.33 m, 4.49 m
6.37 br. d, (1.0)
4.78 m
4.62 dd, (9.5, 3.5)
4.31 m
4.97 m
0
0
Rha 1
0
0
0
0
0
0
0
0
0
0
1.79 m
2
3
4
5
6
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
1.41 m, 1.57 m
1.48 m, 2.32 m
1.76 d, (6.0)
4.86 d, (8.0)
4.15 m
000
Glc 1
0
0
0
0
0
00
00
00
00
00
2.01 m, 2.45 m
5. 30 m
3.38 d, (9.5)
0.96 s
1.13 s
2
3
4
5
6
4.29 m
4.17 m
3.86 m
4.33 m, 4.49 m
5.29 d, (8.0)
4.06 t, (9.5)
4.26 m
4.26 m
3.89 m
4.31 m, 4.49 m
0000
Glc 1
0
0
0
0
0
000
000
000
000
000
1.69 s
2
3
4
5
6
2.25 m
1.90 m, 2.10 m
1.98 m
3.56 dd, (9.0, 6.0), 3.90 m
3
.3.2 Ophiopogonin I (2)
extracted with CHCl3 (3 £ 10 ml). The
aqueous layer was concentrated to dry-
ness. Then, 1 ml of pyridine and 2 mg of
hydroxylamine hydrochloride were added
to the dry residue, and the mixture was
heated at 1008C for 1 h. After cooling,
2
D
0
White amorphous powder; ½aꢀ 272.1 (c
0
1
1
.16, DMSO); IR (KBr) n : 3400, 2932,
max
698, 1643, 1441, 1370, 1134, 1076,
1
2
1
13
038 cm
;
H NMR and
C NMR
spectral data (in C D N) (see Table 2).
5
5
þ
ESIMS: m/z 1201 [M þ Na] , 1177 [M–
Ac O (1.5 ml) was added followed by
2
2
þ
2
H] , 1069 [M þ Na-132] , 1045 [M–H-
heating at 1008C for 1 h and the mixture
was evaporated to dryness under reduced
pressure. The resulted residue was solved
with CHCl3 and analyzed on GC by
comparing with aldononitrile peracetates
of authentic samples. The D-glucose and
2
1
1
32] , 1015 [M–H-162] , 883 [M–H-
2
32-162] , 733 [M–H-132-162-146] .
2
þ
HRESIMS: m/z 1179.5756 [M þ H]
(calcd for C H O , 1179.5799).
56 91 26
3
1
.4 Acid hydrolysis of compounds
and 2
L-rhamnose derivatives of
detected with t values of 11.19 min and
.59 min in the ratio of 3:1, and the
derivatives of D-glucose, L-rhamnose,
and D-xylose of 2 were detected with t
1 were
R
8
A solution of compounds 1 and 2 (5 mg)
was treated with 1 M HCl (dioxane:H O,
2
1
:1, 4 ml) at 1008C for 1.5 h, respectively.
R
After cooling, the reaction mixture was
neutralized with Na CO , and then
values of 11.19, 8.59, and 8.59 min in the
ratio of 3:1:1.
2
3

Journal of Asian Natural Products Research
1235
1 13
Table 2. H NMR (400 MHZ) and C NMR (100 MHZ) spectral data of 2 in pyridine-d5.
Position
d
C
H
d , J (Hz)
Position
d
C
H
d , J (Hz)
0
1
2
3
4
5
6
7
8
9
37.6
30.2
78.0
39.0
140.8
121.8
32.5
31.5
50.4
37.1
21.3
39.7
43.5
55.0
34.6
84.5
64.5
14.2
19.5
103.6
11.9
152.6
23.9
31.5
33.7
74.9
17.3
0.97 m, 1.73 m
1.85 m, 2.09 m
3.88 m
3-O-Glc 1
0
100.1
77.5
77.3
81.5
76.3
61.7
102.0
72.5
72.8
74.1
69.6
18.7
105.8
75.0
78.4
70.8
67.4
103.3
84.1
78.0
71.4
78.3
62.6
106.6
77.1
78.2
71.5
78.6
62.6
4.96 d, (7.0)
4.22 m
4.23 m
4.22 m
3.84 m
4.34 m, 4.45 m
6.25 br. s
4.77 m
2
0
3
4
5
6
0
2.61 m, 2.67 m
0
0
5.27 br. s
1.47 m,1.85 m
1.47 m
0
0
Rha 1
0
0
0
0
0
0
0
0
0
0
2
3
4
5
6
0.88 m
4.59 dd, (9.5, 3.5)
4.32 m
4.91 m
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
1.38 m, 1.41 m
1.12 m, 1.72 m
1.76 d, (6.0)
5.02 d, (7.0)
3.96 m
000
Xyl 1
0
0
0
0
00
00
00
00
0.85 m
1.45 m,2.07 m
4.85 m
2.41 d, (6.0)
0.74 s
1.04 s
2
3
4
5
4.09 m
4.15 m
3.67 t, (8.0), 4.25 m
4.86 d, (8.0)
4.14 m
0
0
000
000
Glc 1
0
0
0
0
0
000
000
000
000
000
2
3
4
5
6
4.32 m
4.15 m
3.86 m
1.66 s
2.19 m
1.48 m, 1.84 m
1.92 m
4.34 m, 4.45 m
5.29 d, (8.0)
4.06 t, (8.0)
4.25 m
4.27 m
3.89 m
4.30 m, 4.49 m
Glc 1
2
0
0000
0000
3.56 dd, (9.0, 6.0), 3.92 m
1.06 d, (6.5)
3
0
0
0
0000
0000
0000
4
5
6
Acknowledgement
[4] A. Tada, M. Kobayashi, and J. Shoji,
Chem. Pharm. Bull. 21, 308 (1973).
Thanks are also extended to Prof. Shanyi Qiao
for NMR measurements.
[
[
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Chem. Lett. 22, 97 (2000).
Note
1.
These authors contributed equally to this
work.
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