全 文 ： 177 Journal of Chinese Pharmaceutical Sciences http://www.jcps.ac.cn
A new furostanol glycoside from Reineckia carnea
Yanwei Hu1,2, Xuan Wang1,2, Kehui Xie2, Guangzhong Tu3, Dan Yuan1*, Hongzheng Fu2*
1. College of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang 110016, China
2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100191, China
3. Beijing Institute of Microchemistry, Beijing 100091, China 
Abstract: Phytochemical investigations of the aerial parts of Reineckia carnea, collected in Yunnan Province of China, were
conducted to explore new chemical constituents. A series of chromatographic and spectroscopic procedures were utilized on the
aqueous solution after partitioned with ethyl acetate, which resulted in the separation of a new furostanol-type glycoside and four
known compounds. The structures of the isolated compounds were elucidated on the basis of spectroscopic techniques (1D and 2D
NMR, IR, HRESIMS) as 26-O-β-D-glucopyranosyl-(25S)-5β-furost-20(22)-en-1α,3β,26-triol-1-O-α-L-arabinopyranosyl-(1→2)-[α-L-
rhamnopyranos-yl]-3-O-α-L-rhamnopyranoside (1), (1β,3β,16β,22S)-cholest-5-en-1,3,16,22-tetrol-1,16-di-(β-D-glucopyranoside) (2),
diosgenin (3), β-sitosterol (4), ecdysterone (5).
Keywords: Reineckia carnea; Steroidal glycosides; Steroids; Structural identification
CLC number: R284 Document code: A Article ID: 1003–1057(2014)3–177–05
Received: 2013-05-02; Revised: 2013-05-15; Accepted: 2013-06-25.
Foundation item: National Natural Science Foundation of China
(Grant No. 81172943).
*Corresponding author. Tel.: 86-24-23986502; 86-10-82805212;
Fax: 86-10-82805212;
E-mail: yuandan_kampo@163.com; drhzfu@yahoo.com.cn
http://dx.doi.org/10.5246/jcps.2014.03.023
1. Introduction
Investigations of steroidal glycosides are mostly focused
on Agavaceae, Liliaceae, Dioscoreaceae, Apocynaceae,
Trilliaceae. To date, based on the aglycone moiety of
the known steroid glycosides, they can be classified into
spirostanol, cholestane, furostanol, stigmastane, pregnane,
and ergostane types. Reineckia carnea (Andr.) Kunth.,
mainly distributed in southwest of China and Japan[1,2],
is one speice of the genus Reineckia (Liliaceae) which
only consists of two speices[3]. From the reported literatures,
what we found mostly from Reineckia carnea were
spirostanol-type saponins, but a few furostanol, cholestane,
stigmastane, pregnane, and ergostane glycosides were also
displayed[4]. In addition, earlier researches performed on
Reineckia carnea resulted in the isolation of lignanamides[5−7],
terpenoids[8,9], flavonoids[5,6,8,10−14], and other constituents.
Reineckia carnea is a folk herbal medicine traditionally
used as an anitarthritic, an antitussive, a hemostatic, and
an antidote[15].
In the former study, we had discovered two new
pregnane glycosides from Reineckia carnea[5,11]. As part
of our ongoing analyses and search for active components
from natural sources, we initiated a phytochemical study
on a commercially available ethanolic extract of Reineckia
carnea. Here we report the isolation and characterization






























of one new furostanol-type glycoside and four known
compounds (Fig. 1).
2. Experimental
2.1. General experimental procedures
Optical rotations were taken on a Perkin-Elmer 241
automatic digital polarimeter (Perkin-Elmer, Waltham,
Figure 1. Chemical structures of compounds 1–5.
HO
OH
O
O
OHO
HO OH
HO
OHO
HO OH
HO
2
O O
HO
HO OH
HO
OHHO
HO
H3C
O O
O
O
O
OHHO
HO
H3C
O
OH
HO O
H
H
O
O
HO
H
H H
H
H
HO
H
H H
OH
O
HO
HO
HO
H
OH
H
H
H
H
1
3
4 5
178 Hu, Y.W. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 177–181
MA, USA). IR spectra were recorded on a Nicolet Nexus
470 FT-IR spectrometer and KBr pellets. The 1D and 2D NMR
spectra were measured on Bruker-500 (Avance DRX-500,
Switzerland) NMR spectrometer and Bruker AV-400
instrument (Bruker Bio-Spin, Fällanden, Switzerland) at
room temperature. HRESI-MS was obtained on a Bruker
APEX Ⅳ mass spectrometer (Billerica, MA, USA).
Column chromatograpies were carried out on D101
macroporous resin (Nankai University Chemical Co., Ltd),
silica gel (200–300 mesh, Qingdao Haiyang Chemical
Co., Ltd.), MCI gel (Mitsubishi Co.), Sephadex LH-20
(18–111 μm, Pharmacia) and ODS silica gel (50 μm, DAISO
Co., Ltd, Japan). HPLC was performed on preparative
columns (YMC-pack ODS-A 120A, 250 mm×10 mm, 5 μm,
YMC Co., Ltd. and Kromasil 100-5C18, 250 mm×10 mm,
5 μm, Kromasil) with a Waters 505 pump and a Waters
2487 dual λ absorbance detector. Solvents of analytical
grade were purchased from Beijing Chemical Factory.
2.2. Plant material
The aerial parts of Reineckia carnea (Andr.) Kunth
were collected in Qujing, Yunnan Province, China, and
were identified by Xujia Hu from Yunnan Institute for the
Control Food & Drug. A voucher specimen was deposited
in the herbarium of State Key Laboratory of Natural and
Biomimetic Drugs, Peking University, Beijing, China.
2.3. Extraction and isolation
The dried aerial parts of Reineckia carnea (100 kg) were
cut and extracted with 75% EtOH for 3 times (3×1.5 h) at
room temperature. The crude extract was concentrated
under vacuum, then suspended in water and partitioned
with ethyl acetate. Aqueous solution was subjected to D101
macroporous resin column chromatography and eluted
with H2O, 30%, 50%, 70% and 100% MeOH, and obtained
mixed components 329.4 g (30% MeOH), 232.3 g (50%
MeOH), 309.4 g (70% MeOH), and 95.2 g (100% MeOH),
respectively. The 70% MeOH fraction was subjected to
silica gel column with CHCl3−MeOH−H2O (30:10:1,
10:5:1, 6:4:1, v/v/v) to get five fractions 1−5 (Fr. 1−Fr. 5).
Fr. 1 was eluted by CHCl3−MeOH−H2O (25:5:1, v/v/v)
on silica gel and further isolated by Sephadex LH-20
(MeOH−H2O, 1:1, v/v) to afford compounds 3 (25 mg),
4 (139 mg) and 5 (15 mg).
Fr. 2−3 were subjected to MCI gel column and ODS
column chromatography eluted with MeOH−H2O (1:1,
v/v) and MeOH−H2O (7:3, v/v) to give crude glycoside
fractions, respectively. Further purification was performed
by preparative HPLC and semi-preparative HPLC. Fr. 2
was purified on a preparative HPLC column using
MeCN−H2O (28:72, v/v) as the mobile phase (flow rate
1.00 mL/min) to yield compound 2 (67 mg). Fr. 3 was
purified on a preparative HPLC column using MeCN−H2O
(26:74, v/v) as the mobile phase (flow rate 1.00 mL/min)
to obtain compound 1 (3 mg).
3. Identification
3.1. 26-O-β-D-Glucopyranosyl-(25S)-5β-furost-20(22)-en
-1α,3β,26-triol-1-O-α-L-arabinopyranosyl-(1→2)-[α-L
-rhamnopyranosyl]-3-O-α-L-rhamnopyranoside
Compound 1, a white amorphous powder with the
optional value of −28.5º (c 0.44, MeOH), showed the
presence of hydroxyl group (3444.1 cm–1) and double
bond (1645 cm–1) in FT-IR spectrum. The molecular
formula of compound 1 was assigned as C50H82O21 on the
basis of its HRESIMS data, which gave the quasimolecular
ion peak at m/z 1041.52023 for [M+Na]+ (calcd. for
1041.52408). In the 1H NMR spectrum, signals for
two tertiary methyl groups at δH 0.71 (3H, s) and δH
1.33 (3H, s), two secondary methyl groups at δH 1.00
(3H, d, J 6.6 Hz) and δH 1.59 (3H, s) were observed
(Table 1). The 13C NMR and DEPT spectra indicated
that compound 1 possesed 50 carbon signals in total,
including 6 methyls, 12 methylenens, 28 methines and 4
quaternary carbons and characteristic carbon resonances at
δC 152.3 and δC 103.7. The 1H and 13C NMR spectroscopic
data (Table 1) of the aglycone moiety of compound 1 closely
resembled those signals of 26-O-β-D-glucopyranosyl-
(25S)-5β-furost-20(22)-en-3β,26-diol-3-O-α-L-rhamnopy-
ranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopy-
ranoside[16], and the difference of C-1 between the two
compounds could be easily observed, which suggested the
aglycone of 1 to be (25S)-5β-furost-20(22)-en-1,3β,26-triol.
Moreover, the furostanol skeleton of 1 could be con-
firmed by detailed 2D NMR spectroscopic data (Fig. 2).
The relative configuration of 1 was interpreted by NOESY
experiment. The NOESY spectrum demonstrated that H-19
had relationships with H-5 and H-1, which revealed
that the A/B ring junction was trans and 1-OH was in
α orientation. In addition, there was no NOESY correlation
between H-19 and H-3, which manifested that 3-OH was
in β orientation (Fig. 3). According to the literature[17], when
δH-26a−δH-26b is in the range of 0.29−0.45, the stereoisomer
of C-25 is in R configuration; when δH-26a−δH-26b is in
the range of 0.57−0.80, the stereoisomer of C-25 is in S
configuration. On the basis of the data of H-26 (Table 1),
C-25 was confirmed as S configuration. Based on all these
observations, the structure of aglycone of 1 was elucidated
as (25S)-5β-furost-20(22)-en-1α,3β,26-triol.
The sequence and linkage positions of the sugar suits
were assigned by detailed 2D NMR spectroscopic data. In
the HMBC spectrum, cross peaks were observed between:
H-1 (δH 5.08) of the inner arabinose and C-1 (δC 78.8) of
the aglycone; H-1 (δH 6.48) of the terminal rhamnose and
C-2 (δC 77.1) of the inner arabinose; H-1 (δH 5.44) of the
179 Hu, Y.W. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 177–181
outer rhamnose and C-3 (δC 70.8) of the aglycone; H-1
(δH 4.82) of the terminal glucose and C-26 (δC 75.3) of the
aglycone. The absolute configurations of the β-D-glucose,
α-L-rhamnose, and α-L-arabinose parts were determined by
acid hydrolysis followed by gas chromatographic analysis
as well as by examination of 2D NMR. All the available
evidence resulted in the conclusion that the structure
of compound 1 was 26-O-β-D-glucopyranosyl-(25S)-5β-
furost-20(22)-en-1α,3β,26-triol-1-O-α-L-arabinopyranosyl-
(1→2)-[α-L-rhamnopyranosyl]-3-O-α-L-rhamnopyranoside.
Figure 2. Selected 1H-1H COSY (━) and HMBC correlations (H→C)
of compound 1. Figure 3. Key NOESY correlations (H C) of compound 1.
Table 1. 1H NMR (500 MHz), 13C NMR (125 MHz) data of compound 1 and 26-O-β-D-glucopyranosyl-(25S)-5β-furost-20(22)-en-3β,26-diol-3-
O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside (δ in Pyridine-d5, J in Hz)
No.
Compound 1
26-O-β-D-Glucopyranosyl-(25S)-5β-
furost-20(22)-en-3β,26-diol-3-O-α-L-
rhamnopyranosyl-(1→2)-[α-L-rhamno-
pyranosyl-(1→4)]-β-D-glucopyranoside
δC δH δC δH
1 78.8 (d) 4.06a 31.1 (d)
2 31.1 (t) 2.30 (m), 2.31 (m) 27.0 (t)
3 70.8 (d) 4.19a 76.3 (d) 4.24
4 31.4 (t) 1.58a, 1.83a 31.1 (t)
5 35.4 (d) 2.00 (m) 35.4 (d)
6 26.4 (t) 1.28a, 1.57a 27.0 (t)
7 27.6 (t) 0.94a, 2.28a 31.1 (t)
8 34.1 (d) 1.44a 37.4 (d)
9 46.5 (d) 1.28a 40.5 (d)
10 39.6 (s) -- 35.4 (t)
11 23.0 (t) 1.23a, 1.47a 21.5 (t)
12 40.3 (t) 1.23a, 1.71a 40.3 (t)
13 43.5 (s) -- 44.1 (s)
14 55.3 (d) 0.83a 55.0 (d)
15 34.6 (t) 1.45 (m), 2.07 (m) 34.6 (t)
16 84.5 (d) 4.78a 84.8 (d) 4.86
17 64.7 (d) 2.42 (1H, d, 10.1) 64.9 (d)
18 14.5 (q) 0.71 (3H, s) 14.6 (q) 0.70 (3H, s)
19 17.0 (q) 1.33 (3H, s) 24.0 (q) 1.08 (3H, s)
20 103.7 (s) -- 103.0 (s)
21 11.8 (q) 1.59 (3H, s) 12.0 (q) 1.64 (3H, s)
22 152.3 (s) -- 152.5 (s)
23 23.7 (t) 1.85a, 2.20a 23.8 (t)
24 31.4 (t) 1.42a, 1.83a 31.6 (t)
25 33.8 (d) 1.93 (m) 33.8 (d)
26 75.3 (t) 3.45 (m), 4.03a 75.4 (t) 3.49, 4.06
27 17.2 (q) 1.00 (3H, d, 6.6) 17.3 (q) 1.05 (d, 6.5)

No.
Compound 1
26-O-β-D-Glucopyranosyl-(25S)-5β-
furost-20(22)-en-3β,26-diol-3-O-α-L-
rhamnopyranosyl-(1→2)-[α-L-rhamno-
pyranosyl-(1→4)]-β-D-glucopyranoside
δC δH δC δH
Glu Glu
1 105.3 (d) 4.82 (1H, d, 7.7) 105.3 (d) 4.83 (1H, d, 7.6)
2 75.3 (d) 4.02 (m) 75.3 (d)
3 78.7 (d) 4.23 (m) 78.7 (d)
4 71.7 (d) 4.23 (m) 71.8 (d)
5 78.6 (d) 3.94 (m) 78.6 (d)
6 62.9 (t) 4.39a, 4.55a 63.0 (t)
Rha-1 Rha-1
1 101.7 (d) 6.48 (1H, br s) 101.6 (d) 6.55 (1H, br s)
2 72.5 (d) 4.81 (m) 72.6 (d)
3 72.8 (d) 4.62 (m) 72.9 (d)
4 74.3 (d) 4.24 (m) 74.0 (d)
5 70.1 (d) 4.37 (m) 69.6 (d)
6 18.7 (q) 1.68 (3H, d, 6.12) 18.5 (q) 1.61 (3H, d, 6.1)
Rha-2 Rha-2
1 99.8 (d) 5.44 (1H, br s) 102.4 (d) 5.88 (1H, br s)
2 72.6 (d) 4.65 (m) 72.8 (d)
3 72.5 (d) 4.65 (m) 72.9 (d)
4 74.1 (d) 4.31 (m) 74.1 (d)
5 69.6 (d) 4.80 (m) 70.5 (d)
6 19.1 (q) 1.75 (3H, d, 6.18) 18.8 (q) 1.75 (3H, d, 6.1)
Ara
1 100.0 (d) 5.08 (1H, d, 6.2) 102.0 (d) 4.83 (1H, d, 7.6)
2 77.1 (d) 4.25 (m) 78.7 (d)
3 79.3 (d) 4.24 (m) 78.6 (d)
4 71.4 (d) 4.14 (m) 77.1 (d)
5 67.0 (t) 3.63 (t), 4.32a 77.1 (d)
61.9 (t)
Glu
a Overlapped with other signals.
O
HO
HO OH
O
O
O
O
O
OHHO
HO
H3C
O
OHHO
HO
H3C
OOH
HO O
HO
H-3 H-5
H-19
H-1
180 Hu, Y.W. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 177–181
3.2. (1β,3β,16β,22S)-Cholest-5-ene-1,3,16,22-tetrol-1,16-
di(β-D-glucopyranoside)
Compound 2 was obtained as a white amorphous powder.
The proposed molecular formula was determined to be
C39H66O14 by molecular ion peak [M+Na]+ at m/z 782.00
in ESIMS. The 1H NMR (400 MHz, Pyridine-d5) spectrum
of 2 showed signals of five methyl groups at δH 0.98 (3H, s),
δH 1.21 (3H, s), δH 0.89 (6H, d, J 5.72 Hz), δH 1.12 (3H, d,
J 6.88 Hz), one olefinic proton at δH 5.45 (1H, d, J 5.04 Hz),
and two anomeric proton signals at δH 4.71 (1H, d, J 7.72 Hz)
and δH 4.94 (1H, d, J 7.64 Hz). On comparison of the NMR
data (Table 2) with the known compound[18], the structure
of 2 was determined to be (1β,3β,16β,22S)-cholest-5-en-
1,3,16,22-tetrol-1,16-di(β-D-glucopyranoside).
3.3. Diosgenin
White needle (CHCl3−MeOH). 1H NMR (400 MHz,
Pyridine-d5) δ: 0.67 (3H, d, J 5.64 Hz), 0.84 (3H, s), 1.02
(3H, s), 1.13 (3H, d, J 6.96 Hz); 13C NMR (100 MHz,
Pyridine-d5) δ: 37.8 (C-1), 32.3 (C-2), 71.3 (C-3), 43.5 (C-4),
142.0 (C-5), 121.0 (C-6), 32.6 (C-7), 31.8 (C-8), 50.4 (C-9),
37.0 (C-10), 21.2 (C-11), 40.0 (C-12), 40.5 (C-13), 56.8 (C-14),
32.2 (C-15), 81.1 (C-16), 62.9 (C-17), 16.4 (C-18), 19.6 (C-19),
42.0 (C-20), 15.1 (C-21), 109.3 (C-22), 31.7 (C-23), 29.3
(C-24), 30.6 (C-25), 66.9 (C-26), 17.3 (C-27). The 1H NMR
and 13C NMR data were in agreement with those in the
literature[19], and the structure of 3 was identified as diosgenin.
3.4. β-Sitosterol
Colorless needle (CHCl3); 13C NMR (100 MHz, CDCl3)
δ: 37.2 (C-1), 31.6 (C-2), 71.8 (C-3), 42.3 (C-4), 140.7
(C-5), 121.7 (C-6), 31.9 (C-7), 31.9 (C-8), 50.1 (C-9),
36.1 (C-10), 21.1 (C-11), 28.2 (C-12), 42.3 (C-13), 56.7
(C-14), 24.3 (C-15), 39.8 (C-16), 56.0 (C-17), 12.0 (C-18),
19.4 (C-19), 36.5 (C-20), 18.8 (C-21), 33.9 (C-22), 26.0
(C-23), 45.8 (C-24), 29.1 (C-25), 19.0 (C-26), 19.8 (C-27),
23.0 (C-28), 11.8 (C-29). The 13C NMR data were in
agreement with those in literature[20], and the structure of
4 was identified as β-sitosterol.
3.5. Ecdysterone
White amorphous powder; 1H NMR (400 MHz, Pyridine-d5)
δ: 1.05 (3H, s), 1.21 (3H, s), 1.36 (6H, s), 1.58 (3H, s),
6.25 (1H, d, J 2 Hz); 13C NMR (100 MHz, Pyridine-d5)
δ: 38.0 (C-1), 68.2 (C-2), 68.1 (C-3), 32.5 (C-4), 51.5
(C-5), 203.6 (C-6), 121.7 (C-7), 166.2 (C-8), 34.5 (C-9),
38.7 (C-10), 21.2 (C-11), 31.8 (C-12), 48.2 (C-13),
84.2 (C-14), 32.1 (C-15), 21.5 (C-16), 50.1 (C-17),
17.9 (C-18), 24.5 (C-19), 77.6 (C-20), 21.7 (C-21), 76.9
(C-22), 27.5 (C-23), 42.7 (C-24), 69.6 (C-25), 30.2 (C-26),
30.0 (C-27). δC 203.6, 166.2, 121.7 were the characteristic
carbon signals of ecdysterone. Compound 5 was identified
as ecdysterone by comparison of spectral data with those
reported in literature[21].
No. δC δH No. δC δH
1 82.8 (d) 3.92 (m) 22 73.1 (d) 4.28 (m)
2 37.1 (t) 1.76 (m), 2.28 (m) 23 33.7 (t) 1.77a, 1.85a
3 67.9 (d) 3.80 (m) 24 36.6 (t) 1.63a, 1.89a
4 43.6 (t) 2.53a, 2.62 (t) 25 28.8 (d) 1.61 (m)
5 139.4 (s) -- 26 22.9 (q) 0.89 (d, 5.72)
6 124.7 (d) 5.45 (d, 5.04) 27 23.0 (q) 0.89 (d, 5.72)
7 31.7 (t) 1.31a, 1.75a Glu
8 33.0 (d) 1.32a 1′ 101.3 (d) 4.94 (d, 7.64)
9 50.1 (d) 1.40 (m) 2′ 75.4 (d) 3.94 (m)
10 42.8 (s) -- 3′ 78.6 (d) 4.12 (m)
11 23.7 (t) 1.54 (m), 2.79 (m) 4′ 72.4 (d) 4.08 (m)
12 40.4 (t) 1.38 (m), 1.98 (m) 5′ 78.1 (d) 3.79 (m)
13 42.1 (s) -- 6′ 63.5 (t) 4.47a, 4.48a
14 55.0 (d) 0.85a
15 37.4 (t) 2.07a, 2.75a 1″ 106.9 (d) 4.71 (d, 7.72)
16 82.7 (d) 4.48 (t) 2″ 75.6 (d) 3.97 (m)
17 58.0 (d) 1.94 (m) 3″ 78.7 (d) 4.18 (m)
18 13.8 (q) 0.98 (s) 4″ 71.7 (d) 4.21 (m)
19 14.7 (q) 1.21 (s) 5″ 78.2 (d) 3.98 (m)
20 35.9 (d) 2.49 (m) 6″ 62.8 (t) 4.35a, 4.36a
21 12.4 (q) 1.12 (d, 6.68)
Glu
Table 2. 1H (400 MHz) and 13C NMR (100 MHz) data of compound 2 (δ in Pyridine-d5, J in Hz)
a Overlapped with other signals.
181 Hu, Y.W. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 177–181
Acknowledgements
This work was financially supported by the National
Natural Science Foundation of China (Grant No. 81172943).
The authors would like to express their gratitude to
Prof. Xujia Hu for his technical support, and Xulin Sun and
Weiqing Zhang for running the NMR and MS samples.
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吉祥草中一个新的呋甾皂苷
胡艳维1,2, 王璇1,2, 谢可辉2, 涂光忠3, 袁丹1*, 付宏征2*
1. 沈阳药科大学 中药学院, 辽宁 沈阳 110016
2. 北京大学医学部 天然药物及仿生药物国家重点实验室, 北京 100191
3. 北京微量化学研究所, 北京 100091  

摘要: 对云南产吉祥草的地上部分进行了植物化学研究。针对乙酸乙酯萃取后的水溶液, 利用一系列色谱方法分离
得到了一个新呋甾皂苷和四个已知化合物。通过1D NMR、2D NMR, IR和HRESI-MS的方法对分离得到化合物进行
了结构鉴定, 分别为 26-O-β-D-glucopyranosyl-(25S)-5β-furost-20(22)-en-1α,3β,26-triol-1-O-α-L-arabinopyranosyl-(1→2)-[α-L-
rhamnopyranosyl]-3-O-α-L-rhamnopyranoside (1), (1β,3β,16β,22S)-cholest-5-en-1,3,16,22-tetrol-1,16-di-(β-D-glucopyranoside) (2),
diosgenin (3), β-sitosterol (4), ecdysterone (5)。
关键词: 吉祥草; 甾体皂苷; 甾体; 结构鉴定