Steroidal saponins from the stem of Yucca elephantipes

Article abstract of DOI:10.1016/j.phytochem.2007.06.015

Ten steroidal saponins with cis-fused A/B ring, including a smilagenin glycoside, elephanoside A (4), and the five furostanol bisdesmosides, elephanosides B-F (6-10), were isolated from the stems of Yucca elephantipes Regel. (Agavaceae). Their structures were determined by detailed chemical and spectroscopic analysis. All the isolated compounds were tested for their in vitro antifungal and antibacterial activities. Only the two known spirostanol glycosides Ys-II (1) and Ys-IV (2) showed moderate inhibitory activity against the growth of Candida albicans and Cryptococcus neoformans.

Full text of DOI:10.1016/j.phytochem.2007.06.015

Available online at www.sciencedirect.com
PHYTOCHEMISTRY
Phytochemistry 69 (2008) 264–270
www.elsevier.com/locate/phytochem
Steroidal saponins from the stem of Yucca elephantipes
a
a,
b
*
Ying Zhang , Ying-Jun Zhang , Melissa R. Jacob ,
b
a,
*
Xing-Cong Li , Chong-Ren Yang
a
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany,
Chinese Academy of Sciences, Kunming 650204, PR China
National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA
b
Received 28 November 2006; received in revised form 31 May 2007
Available online 1 August 2007
Abstract
Ten steroidal saponins with cis-fused A/B ring, including a smilagenin glycoside, elephanoside A (4), and the five furostanol bisdesmo-
sides, elephanosides B–F (6–10), were isolated from the stems of Yucca elephantipes Regel. (Agavaceae). Their structures were determined
by detailed chemical and spectroscopic analysis. All the isolated compounds were tested for their in vitro antifungal and antibacterial
activities. Only the two known spirostanol glycosides Ys-II (1) and Ys-IV (2) showed moderate inhibitory activity against the growth
of Candida albicans and Cryptococcus neoformans.
ꢀ
2007 Published by Elsevier Ltd.
Keywords: Yucca elephantipes; Agavaceae; Steroidal saponins; Elephanosides A–F; Antifungal activity
1
. Introduction
2000; Oleszek et al., 2001a,b; Piacente et al., 2005), Y. fila-
mentosa (Dragalin and Kintia, 1975; Plock et al., 2001),
and Y. aloifolia (Bahuguna et al., 1991; Benidze et al.,
1984; Kishor and Sati, 1990; Kishor et al., 1992).
The genus Yucca (Agavaceae) contains about 35–40 spe-
cies, which are mainly distributed in Central and Northern
America. Many of them as ornamental plants are com-
monly cultivated in the tropical gardens of the World.
Yucca extracts are used not only to feed livestock and
poultry to improve their growth and productivity
Yucca elephantipes Regel. is the tallest of the Yuccas,
reaching 30 feet in height with glossy bluish green leaves
that can grow up to 4 feet long with a narrow width of
about 3 inches. Its trunk is somewhat thickened at the
base and very rough. It is native to Mexico and intro-
duced to China as an evergreen ornamental plant. The
leaf extract of Y. elephantipes was reported to have anti-
viral activity on TMV (Tobacco mosaic virus) (Wang,
2006); however, no chemical study has been reported
on this plant. As a continuing work to search for new
antifungal natural products from monocotyledons, partic-
ularly from the Liliales (Yang et al., 2006; Zhang et al.,
2006), a phytochemical investigation on the air-dried
stem of Y. elephantipes was carried out to afford 10 ste-
roidal glycosides with cis-fused A/B ring system. This
paper presents the isolation and structure elucidation of
these compounds as well as their in vitro antifungal and
antibacterial activities.
(
Anthony et al., 1994; Balog et al., 1994), but also to reduce
ammonia and odors in poultry excreta on farms (Cheeke,
999). The steroidal saponins are considered to be closely
1
involved with these actions (Varanda, 1984). Until now,
studies on steroidal glycosides from Yucca genus have been
mainly focused on Y. gloriosa (Benidze et al., 1991; Gio-
rgadze and Gurielidze, 1991; Gonzalez et al., 1972; Kemer-
telidze and Pkheidze, 1972; Kemertelidze and Benidze,
2
1
001; Nakano et al., 1988, 1989, 1991a,b; Pkheidze et al.,
981, 1985, 1991a,b), Y. schidigera (Miyakoshi et al.,
*
Corresponding authors. Tel.: +86 871 5223235; fax: +86 871 5150124.
E-mail addresses: zhangyj@mail.kib.ac.cn (Y.-J. Zhang), cryang
mail.kib.ac.cn (C.-R. Yang).
@
0
031-9422/$ - see front matter ꢀ 2007 Published by Elsevier Ltd.
doi:10.1016/j.phytochem.2007.06.015

Y. Zhang et al. / Phytochemistry 69 (2008) 264–270
265
2
. Results and discussion
hydrolysis with 2 M HCl, 4 afforded smilagenin [(25R)-
b-spirostan-3b-ol] (Agrawal et al., 1985) as aglycone,
5
Repeated column chromatography (including by Diaion
and D-xylose and D-galactose as sugar residues. The large
coupling constants (ꢁ7 Hz) of the anomeric protons indi-
cated the b-configuration at the anomeric centers for both
D-xylopyranosyl and D-galactopyranosyl units. Connectivi-
ties of the sugar moieties were established by the HMBC
correlations of the anomeric proton of the xylosyl (d
5.14) with C-2 of galactosyl (d 82.4) moieties, and the ano-
meric proton of the galactosyl (d 4.91) with that of the C-3
of the aglycone (d 74.2). Thus, the structure of 4 was eluci-
dated to be (25R)-5b-spirostan-3b-ol-3-O-b-D- xylopyrano-
syl-(1 ! 2)-b-D-galactopyranoside.
HP-20SS, Sephadex LH-20, MCI-gel CHP20P, silica gel
and reversed phase silica gel Rp-8) of the n-butanol extract
of Y. elephantipes stem afforded six new steroidal glyco-
sides (4, 6–10). In addition, four known compounds were
obtained and identified as Ys-II (1) (Nakano et al., 1989),
Ys-IV (2) (Nakano et al., 1989), YS-VIII (3) (Nakano
et al., 1991b) and (25R)-26-O-b-D-glucopyranosyl-5b-furo-
stan-3b, 22n, 26-triol-3-O-b -D-glucopyranosyl-(1 ! 2)-b-D-
galactopyranoside (5) (Skhirtladze et al., 2006), respec-
tively, on the basis of their physical and spectroscopic data
and by comparison with reference values (see Chart 1).
Compound 4, named elephanoside A, showed a positive
reaction (green color) to the anisaldehyde reagent, but a
negative reaction to Ehrlich reagent, indicating the pres-
Compounds 6–10, named elephanoside (B–F), were all
furostanol glycosides as indicated by the positive reaction
(red color) to the Ehrlich reagent (Kiyosawa and Hutoh,
1968) and a characteristic quaternary carbon signal
around d 110 observed in the DEPT spectrum. All of
their 25R configurations were determined based on their
small differences (Dab = d ꢀ d ) of the chemical shifts
ence of a spirostanol skeleton (Kiyosawa and Hutoh,
1
1
968). These observations were coincident with the
H
1
3
and C NMR spectroscopic data, in which four typical
a
b
methyl proton signals at d 0.82 (s, Me-18), 0.99 (s, Me-
(d , d ) of the germinal protons at H -26 (D = 0.30–
a b 2 ab
1
9), 0.67 (d, J = 4.3 Hz, Me-27) and 1.14 (d, J = 6.7 Hz,
0.34 ppm). It has been described that Dab is usually
>0.57 ppm in 25S compounds and <0.48 ppm in 25R
compounds (Agrawal, 2004). The molecular formulas of
6–10 were determined to be C H O , C H O ,
Me-21), and a characteristic C-22 resonance for a spirosta-
nol skeleton at d 109.3 were observed (Li et al., 1990, 1992).
The negative ion HRESIMS gave a quasi-molecular ion
5
1
86 24
51 84 25
ꢀ
peak at m/z 709.4163 [MꢀH] , corresponding to a molec-
C H O , and C H O , respectively, on the basis of
45 74 20 51 86 25
1
3
ular formula C H O . The negative ion FABMS also
analyses of the negative ion HRESIMS and C NMR
spectra.
3
8
62 12
showed a characteristic fragment ion peak at m/z 577
ꢀ
1
13
[
Mꢀ132 (pentosyl)ꢀH] , indicating the existence of a ter-
The H and C NMR spectra of 6 showed the presence
of 4 characteristic methyls [d 0.86 (s, Me-18), 0.95 (s, Me-
19), 0.97 (d, J = 6.6 Hz, Me-27), and 1.33 (d, J = 6.7 Hz,
Me-21)], 11 methylenes [including one oxygen-bearing
carbon at d 75.4 (C-26)], 9 methines [including two oxygen-
bearing carbons at d 75.2 (C-3) and 81.3 (C-16)], and 3 qua-
ternary carbons [including one oxygen-bearing carbon at d
minal pentosyl unit in the molecule. The presence of the
two anomeric proton signals at d 4.91 (d, J = 7.6 Hz),
and 5.14 (d, J = 7.0 Hz) observed in the H NMR spectrum
suggested that 4 was a spirostanol diglycoside. Upon acid
1
110.7 (C-22)]. In addition, signals ascribable to four sugar
moieties [anomeric protons at d 4.81 (d, J = 7.6 Hz), 4.84
Glc II OH
H
O
O
(d, J = 7.6 Hz), 5.40 (d, J = 7.6 Hz) and 5.57 (d,
J = 7.7 Hz)] were also observed. These NMR spectroscopic
data were closely related to those of (25R)-26-O-b-D-gluco-
pyranosyl-5b-furostan-3b,22a,26-triol-3-O-b-D-glucopyr-
anosyl-(1 ! 2)-b-D-galactopyranoside (5) (Skhirtladze
et al., 2006), except for the appearance of one more b-
glucopyranosyl unit signals. The full assignments of sugar
signals were carried out by HSQC and TOCSY experi-
ments. In the HMBC spectrum of 6, the additional ano-
meric proton at d 5.40 (GlcIII H-1) was correlated with d
83.9 (Gal C-3), indicating its location was on the C-3 posi-
tion of the inner galactopyranosyl unit. Other HMBC cor-
relations of dH 4.81 (GlcII H-1) with dC 75.4 (C-26), dH
5.57 (GlcI H-1) with d 78.0 (Gal C-2), and d 4.84 (Gal
HO
HO
2
5
2
1
O 26
27
OH
2
1
0
7
R
2
24
1
8
22
16O
HO
R
2
1
9
1
1
13
1
O
2
14
15
9
1
0
7
1
R O
4
H 6
R1
R2
R O
1
R1
R2
H
5
: S
2
3
3
2
2
3
H,H
1
2
3
4
: S
2
H,H
6: S
7: S
8: S
9: S
0: S
H,H
: S
: S
: S
3
3
1
H,H
O
=O
=O
H,H
H, β-OH
H, β-OH
1
OH OH
O
OH
OH
OH
O
OH
O
Glc III OH
C
H
O
HO
HO
OH
O
HO
HO
H-1) with dC 75.2 (C-3 of aglycone) confirmed the sugar
sequence and linkage site to the aglycone. Moreover, enzy-
matic hydrolysis of 6 with b-glucosidase yielded glucose as
the sugar residue and Ys-IV (2) (Nakano et al., 1989) as the
corresponding spirostanol glycoside, which confirmed that
6 was a furostanol type of compound 2. Therefore, the
O
O
O
OH
O
OH
O
O
HO
HO
HO
Glc I
HO
Glc I
OH
S1
HO
OH
S2
HO
OH
S3
Chart 1. Steroidal saponins 1–10 isolated form Yucca elephantipes.

266
Y. Zhang et al. / Phytochemistry 69 (2008) 264–270
structure of 6 was assigned as (25R)-26-O-b-D-glucopyr-
anosyl-5b-furostan-3b,22n,26-triol-3-O-b-D-glucopyranosyl-
Table 2
1
3
C NMR spectroscopic data for the sugar moieties of compounds 4 and
6–10 (in pyridine-d
5
, d in ppm)
(
1 ! 2)-O-[b-D-glucopyranosyl-(1 ! 3)]-b-D-galactopyrano-
side.
The molecular formula of compound 7 has one more
oxygen atom, but two less hydrogen atoms than that of
Position
4
6
7
8
9
10
Gal-1
101.4
82.4
75.4
69.9
76.7
62.2
102.1
78.0
83.9
69.9
76.5
63.5
101.9
77.8
84.1
69.9
76.5
62.9
102.5
81.8
75.3
69.9
77.0
62.2
102.6
81.7
75.3
69.9
77.0
62.2
102.4
77.8
84.2
69.9
76.9
63.6
2
3
4
5
6
1
3
6
. The C NMR spectra of 7 (Tables 1 and 2) were in good
agreement with those of 6, except for obvious differences at
C-11 (d 37.8), C-12 (d 213.3), C-13 (d 56.0), and C-17 (d
5
5.1), suggesting that one of the methylene at C-12 in 6
Xyl-1
107.2
76.6
78.1
71.2
67.6
was oxygenated to be a carbonyl group in 7. This was con-
firmed by the long-range correlations of d 1.12 (Me-18),
2
3
4
5
1
.42 (H-14), 2.17 (H-11a), 2.35 (H-11b), 2.94 (H-17) with
d 213.3 (C-12) in the HMBC experiment. Enzymatic hydro-
lysis of 7 with b-glucosidase gave glucose and YS-VIII (3)
as the corresponding spirostanol glycoside, indicating that
GlcI-1
104.5
76.5
78.7
72.6
78.5
62.8
104.5
76.4
78.4
72.8
77.9
63.5
106.2
76.7
78.5
71.7
78.1
62.8
106.1
76.7
78.6
71.7
78.1
62.8
104.5
76.4
78.6
72.8
78.1
62.9
2
3
4
5
6
7
was a furostanol type of 3. Therefore, compound 7 was
characterized as (25R)-26-O-b-D-glucopyranosyl-5b-furo-
stan-3b,22n,26-triol-12-one-3-O-b-D-glucopyranosyl-(1 ! 2)-
O-[b-D-glucopyranosyl-(1 ! 3)]-b-D-galactopyranoside.
Acid hydrolysis of 8 produced D-galactose and D-glucose
as sugar residues, and gloriogenin as the sapogenin (Nak-
ano et al., 1991b). Comparison of the NMR spectroscopic
data (Tables 1 and 2) with those of 7 and 5 indicated that 8
had a same aglycone as 7 and an identical sugar moiety to
GlcII-1
105.0
75.2
78.5
71.7
78.0
62.5
105.0
74.8
78.5
71.8
78.5
62.6
105.0
75.3
78.7
71.7
78.6
62.8
105.0
75.6
78.7
71.7
78.6
62.9
104.9
75.2
78.4
71.8
77.9
62.6
2
3
4
5
6
GlcIII-1
105.4
75.2
78.6
71.5
78.5
62.4
105.3
75.4
78.6
71.6
78.5
62.4
105.3
75.2
78.5
71.6
78.4
62.4
5
4
. In the HMBC spectrum, three anomeric protons at d
.89 (d, J = 7.7 Hz, Gal H-1), 5.30 (d, J = 7.6 Hz, GlcI
2
3
4
5
6
H-1), and 4.83 (d, J = 7.7 Hz, GlcII H-1) showed obvious
correlations with d 75.3 (C-3), 81.8 (Gal C-2) and 75.3
Table 1
1
3
C NMR spectroscopic data for the aglycone moieties of compounds 4
and 6–10 (in pyridine-d
5
, d in ppm)
(C-26), respectively, confirming the sugar sequence and
Position
4
6
7
8
9
10
30.8
linkages in 8. Accordingly, the structure of 8 was deduced
to be (25R)-26-O-b-D-glucopyranosyl-5b-furostan-3b,22n,
1
2
3
4
5
6
7
8
9
30.2
27.1
74.2
30.7
36.3
27.1
26.8
35.6
40.2
35.3
21.2
40.3
40.9
56.5
31.9
81.3
63.1
16.6
23.9
42.0
15.1
30.0
26.9
75.2
30.8
36.6
26.9
27.0
35.3
40.3
35.3
21.2
40.4
40.7
56.4
32.5
81.3
64.1
16.8
24.0
41.3
16.6
110.7
37.3
28.4
34.3
75.4
17.5
30.4
26.6
75.2
30.6
36.1
26.8
26.5
34.7
42.1
35.8
37.8
213.3
56.0
56.0
31.8
79.8
55.1
16.2
23.1
41.3
15.3
110.8
37.1
28.4
34.3
75.2
17.5
30.7
26.5
75.3
30.8
36.5
26.8
26.4
34.7
42.0
35.7
37.8
213.4
56.0
56.0
31.7
79.8
55.1
16.3
23.2
41.3
15.3
110.8
37.1
28.4
34.3
75.3
17.5
31.1
26.8
75.4
31.0
36.8
26.8
27.2
34.7
39.5
35.4
31.5
79.7
47.1
55.3
32.2
81.4
63.8
11.5
24.0
41.7
15.9
26.7
75.4
30.5
36.4
26.8
27.1
34.7
39.5
35.3
31.5
79.7
47.1
55.3
32.2
81.4
63.9
11.4
23.9
41.7
15.7
111.0
37.3
28.5
34.4
75.2
17.6
2
6-triol-12-one-3-O-b-D-glucopyranosyl-(1 ! 2)-b-D-galac-
topyranoside.
1
13
The H and C NMR spectroscopic data of 9 were very
similar to those of 5, except for some differences in the agly-
cone part at C-11 (d 31.5, CH ), C-12 (d 79.7, CH), C-13 (d
2
4
7.1, C) and C-18 (d 11.5, CH ). The NMR spectroscopic
3
data in the aglycone part of 9 were coincident with those
of 12b-hydroxysmilagenin (Nakano et al., 1991a). These
observations suggested that 9 had one more hydroxyl
attached at the C-12 position, relative to 5. In the ROESY
spectrum of 9, correlations of d 3.55 (t, J = 5.6 Hz, H-12a)
with H-14 (d 1.07, m), H-17 (d 2.35, dd, J = 6.4, 8.2 Hz)
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
and CH -21 (d 1.62, d, J = 6.6 Hz) further confirmed
3
the 12b-hydroxyl group in 9. Enzymatic hydrolysis of 9
with b-glucosidase afforded glucose and its corresponding
spirostanol saponin, (25R)-5b-spirostan-3b,12b-diol-3-
O-b-D-glucopyranosyl-(1 ! 2)-b-D-galactopyranoside (YS-
XI), which was originally isolated from the caudex of Yucca
gloriosa (Nakano et al., 1991a). Therefore, compound 9 was
assigned as (25R)-26-O-b-D-glucopyranosyl-5b-furostan-
109.3
32.2
29.3
30.6
66.9
17.4
111.1
37.4
28.5
34.4
75.3
17.6
3
b,12b,22n,26-tetraol-3-O-b-D-glucopyranosyl-(1 ! 2)-b-
D-galactopyranoside.

Y. Zhang et al. / Phytochemistry 69 (2008) 264–270
267
Table 3
4. Experimental
a
Antifungal activity of steroidal saponins 1 and 2 (IC50/MIC/MFC,
lg/ml)
4.1. General methods
C. albicans ATCC 90028 C. neoformans ATCC 90113
IC50
MIC
10.0
na
0.31
MFC
20.0
na
1.25
IC50
MIC
MFC
The instruments for the measurement of NMR spectra
1
13
1
5.0
15.0
0.15
6.0
15.0
0.55
10.0
20.0
1.25
20.0
20.0
1.25
were Bruker AM-400 (for H NMR and C NMR) and
DRX-500 (for 2D NMR), with TMS as internal standard
and pyridine-d5 as solvent. Optical rotations were
recorded on a SEPA-3000 automatic digital polarimeter.
FABMS (negative ion mode) and HRESIMS (negative
ion mode) spectra were measured on VG AutoSpe 3000
and API Qstar Pulsar LC/TOF spectrometers, respec-
tively. GC analysis were identical to those described in
our previous paper (Zhang et al., 2006). Agilent Technol-
ogies HP5890 gas chromatograph was the equipment car-
rying H2 flame ionization detector and 30QC2/AC-5
quartz capillary column (30 m · 0.32 mm). The conditions
as followings: column temperature: 180 ꢁC/280 ꢁC; pro-
b
b
2
Amphotericin B
a
IC50: 50% inhibitory concentration; MIC: minimum inhibitory con-
centration; MFC: minimum fungicidal concentration.
b
Not active at the highest test concentration of 20 lg/mL.
1
13
The H and C NMR spectra of 10 showed the presence
of the same aglycone as in 9 and the same sugar moiety as
in 6 and 7. Acid hydrolysis of 10 produced 12b-hydroxy-
smilagenin (Nakano et al., 1991a). The NMR signal assign-
ments of 10 were facilitated by the HSQC, HMBC, and
TOCSY experiments. The 12b-OH configuration in 10
was confirmed by the same ROESY correlations as in 9.
Therefore, the structure of 10 should be (25R)-26-O-b-D-
glucopyranosyl-5b-furostan-3b,12b,22n,26-tetraol-3-O-b-
D-glucopyranosyl-(1 ! 2)-O-[b-D-glucopyranosyl-(1 ! 3)]-
b-D-galactopyranoside.
grammed increase, 3 ꢁC/min; carrier gas: N (1 ml/min);
2
injection and detector temperature: 250 ꢁC; injection vol-
ume: 4 ll, split ratio: 1/50. CC was performed over Dia-
ion
HP-20SS
(Mitsubishi,
Japan),
macroporus
absorption resin D-101 (Qingdao Makall, China), silica
gel (200–300 mesh, Qingdao Makall, China), Sephadex
LH-20 (Pharmacia, Sweden), MCI-gel CHP20P (Mitsubi-
shi, Japan) and reversed phase silica gel RP-8 (40–63 lm,
Merck, Germany). TLC was carried out on silica gel H
(size: 50 · 100 mm, thickness: 0.20–0.25 mm, Qingdao
Makall, China), and spots were visualized by spraying
with anisaldehyde–H SO (for both spirostanol and
Saponins 1–10 were tested for their antifungal activity
against Candida albicans and Cryptococcus neoformans
using amphotericin B as a positive control. Only two spi-
rostanol smilagenin glycosides 1 and 2 exhibited moderate
antifungal activity (Table 3). The lack of antifungal activity
of all furostanol glycosides (5–10) and two other spirosta-
nol glycosides (3 and 4) indicated that both aglycone and
sugar moieties are influential factors for the antifungal
activity of steroidal saponins. All compounds were also
tested for activity against the filamentous fungus Aspergil-
lus fumigatus, and the bacteria Escherichia coli, Pseudomo-
nas aeruginosa, and Mycobacterium intracellulare and
inactive at the highest test concentration of 20 lg/ml.
2
4
furostanol saponins) and Ehrlich reagent (for furostanol
saponins) followed by heating.
4.2. Plant material
The stems of Y. elephantipes were collected from the
East Garden of Kunming Institute of Botany, Chinese
Academy of Sciences, Yunnan, China. A voucher specimen
(KUN No. 0831640) is deposited at the Herbarium of the
3
. Concluding remarks
Institute mentioned above.
In conclusion, 10 steroidal saponins with cis-fused
4.3. Extraction and isolation
A/B ring were isolated from the stems of Y. elephantipes.
Of these, six new glycosides (4, 6–10) were identified.
The in vitro antifungal and antibacterial bioassay showed
that only two known spirostanol glycosides Ys-II (1) and
Ys-IV (2) had moderate inhibitory activity against the
growth of Candida albicans and Cryptococcus neofor-
mans. Steroidal saponins with cis-fused A/B rings are
uncommon in nature compared to those with trans-fused
A/B ring, and have mainly been reported in the genus
Yucca, especially Y. gloriosa and Y. schidigera. As a kind
of characteristic secondary metabolite, further and sys-
tematic chemical work on the glycosides with a cis-fused
A/B ring from the genus Yucca should be carried out in
the future to provide more chemotaxonomic information
on this genus.
The air-dried stems (4.8 kg) of Y. elephantipes were
extracted with MeOH (6 L · 3) under reflux for three
times. The organic extracts were combined and removed
in vacuo, and the residue suspended into H O was then
2
partitioned with CHCl and n-BuOH, successively. The
3
n-BuOH extract (240 g) was subjected to a silica gel
CC eluted with CHCl –MeOH–H O (7.5:2.5:0.4) to
3
2
afford seven fractions (Frs. 1–7). Fr. 2 (3.5 g) was applied
to Sephadex LH-20 and MCI-gel CHP20P columns elut-
ing with MeOH–H O (0:1–1:0) to give 4 (14 mg). When
2
Fr. 3 was concentrated in vacuo, a precipitate appeared,
which was washed with MeOH for three times to afford
1 (6 g). Fr. 4 (11 g) was subjected to MCI-gel CHP20P
followed by reversed phase RP-8 CC, eluting with

268
Y. Zhang et al. / Phytochemistry 69 (2008) 264–270
MeOH–H O (40–100%) to give 2 (20 mg) and 3 (40 mg).
Fr. 5 (96 g) was applied to a Diaion HP-20SS and
H-1), 4.84 (1H, d, J = 7.6 Hz, Gal H-1), 4.99 (1H, m, H-
16), 5.40 (1H, d, J = 7.6 Hz, GlcIII H-1), 5.57 (1H, d,
2
1
3
reversed phase Rp-8 CC eluting with MeOH–H O (4:6–
J = 7.7 Hz, GlcI H-1). C NMR (pyridine-d , 400 MHz):
2
5
1
:0) to afford 5 (228 mg). Repeated CC of Fr. 6 (30 g)
see Tables 1 and 2.
over MCI-gel CHP20P (60–100% MeOH in H O), silica
2
gel (CHCl –MeOH–H O, 7:3:0.5), Sephadex LH-20 (0–
4.3.3. Elephanoside C (7)
3
2
2
D
3
2
0% MeOH in H O) and RP-8 (30–90% aq. MeOH) to
White amorphous powder, ½aꢂ ¼ þ5:2 (c 0.35, MeOH).
2
ꢀ
furnish 8 (29 mg) and 9 (40 mg). Fr. 7 (64 g) was sub-
jected to a macroporus absorption resin D-101 and
FAB-MS (negative ion mode) m/z: 1096 [M] , 933 [MꢀGlc
ꢀ
ꢀ
(162)ꢀH] , 771 [MꢀGlc (162) · 2ꢀH] , 591 [MꢀGlc
ꢀ
MCI-gel CHP20P, eluting with MeOH–H O (0:1–1:0),
(162) · 3–H OꢀH] . HRESI-MS (negative ion mode) m/
2
2
ꢀ
followed by CC on Sephadex LH-20 (10% aq. MeOH)
z: 1095.5198 [M(C H O )ꢀH] (calcd. for 1095.5229).
5
1
84 25
1
and silica gel (CHCl –MeOH–H O, 7:3:0.5) to afford 6
H NMR (pyridine-d , 500 MHz): d 0.89 (1H, m, H-7a),
5
3
2
(
20 mg), 7 (56 mg), and 10 (15 mg).
0.95 (3H, s, Me-19), 0.97 (3H, d, J = 6.6 Hz, Me-27), 1.12
3H, s, Me-18), 1.29 (1H, m, H-7b), 1.42 (1H, m, H-14),
(
4
.3.1. Elephanoside A (4)
White amorphous powder, ½aꢂ ¼ ꢀ55:8 (c 0.72, pyri-
1.55 (3H, d, J = 6.7 Hz, Me-21), 1.66 (1H, m, H-24a),
1.71 (1H, m, H-9), 1.76 (1H, m, H-8), 1.91 (1H, m, H-
25), 2.01 (1H, m, H-24b), 2.04 (2H, m, H-23a,b), 2.17
(1H, dd, J = 4.1, 13.1 Hz, H-11a), 2.21 (1H, m, H-20),
2.24 (1H, m, H-5), 2.35 (1H, m, H-11b), 2.94 (1H, t,
J = 7.3 Hz, H-17), 3.61 (1H, dd, J = 6.2, 9.7 Hz, H-26a),
3.94 (1H, m, H-26b), 4.02 (1H, m, GlcI H-2), 4.17 (1H, t,
J = 9.1 Hz, GlcI H-4), 4.19 (1H, m, GlcII H-4), 4.23 (1H,
m, H-3), 4.37 (1H, m, Gal H-3), 4.77 (1H, d, J = 2.4 Hz,
Gal H-4), 4.80 (1H, d, J = 7.4 Hz, Gal H-1), 4.83 (1H, d,
J = 7.1 Hz, GlcII H-1), 4.91 (1H, dd, J = 7.3, 14.2 Hz, H-
16), 5.40 (1H, d, J = 7.7 Hz, GlcIII H-1), 5.58 (1H, d,
2
D
3
ꢀ
dine). FABMS (negative ion mode): m/z 709 [MꢀH] ,
ꢀ
5
77 [Mꢀ132 (Xyl)ꢀH] . HRESIMS (negative ion mode):
ꢀ
m/z 709.4155 [M(C H O )ꢀH] (calcd. for 709.4169).
3
8
62 12
1
H NMR (pyridine-d , 400 MHz): d 0.67 (3H, d,
5
J = 4.3 Hz, Me-27), 0.82 (3H, s, Me-18), 0.99 (3H, s, Me-
9), 1.08 (1H, m, H-14), 1.09 (1H, m, H-12a), 1.14 (3H,
1
d, J = 6.7 Hz, Me-21), 1.23 (1H, m, H-11a), 1.32 (1H, m,
H-9), 1.35 (1H, m, H-11b), 1.41 (1H, dd, J = 5.6, 11.2 Hz,
H-15a), 1.47 (1H, m, H-4a), 1.50 (1H, m, H-8), 1.55 (2H,
m, H-24a,b), 1.68 (2H, m, H-23a,b), 1.70 (1H, m, H-12b),
1
1
2
1
3
.87 (1H, m, H-4b), 1.96 (1H, m, H-20), 2.04 (1H, m, H-
5b), 2.28 (1H, m, H-5), 3.51 (1H, br t, J = 9.6 Hz, H-
6a), 3.58 (1H, br d, J = 9.6 Hz, H-26b), 3.62 (1H, br t,
J = 7.8 Hz, GlcI H-1). C NMR (pyridine-d , 400 MHz):
5
see Tables 1 and 2.
J = 10.8 Hz, Xyl H-5a), 4.01 (1 H, m, Gal H-5), 4.07
1H, t, J = 8.4 Hz, Xyl H-2), 4.11 (1H, t, J = 8.4 Hz, Xyl
H-3), 4.24 (1H, m, Xyl H-4), 4.38 (1H, m, H-3), 4.42
1H, m, Xyl H-5b), 4.56 (1H, br s, Gal H-4), 4.57 (1H, m,
Gal H-2), 4.61 (1H, m, H-16), 4.91 (1H, d, J = 7.6 Hz,
4.3.4. Elephanoside D (8)
2
D
3
(
White amorphous powder, ½aꢂ ¼ þ11:5 (c 0.13,
ꢀ
ꢀ
MeOH). FAB-MS (negative ion mode) m/z: 933 [MꢀH] ,
ꢀ
(
771 [MꢀGlc (162)ꢀH] , 609 [MꢀGlc (162) · 2ꢀH] .
HRESI-MS (negative ion mode) m/z: 933.4691 [M
1
3
ꢀ
1
Gal H-1), 5.14 (1H, d, J = 7.0 Hz, Xyl H-1). C NMR
pyridine-d , 400 MHz): see Tables 1 and 2.
(C H O )ꢀH] (calcd. for 933.4701). H NMR (pyri-
4
5
74 20
(
dine-d , 400 MHz): d 0.89 (1H, m, H-7a), 0.96 (3H, s, Me-
5
5
19), 0.97 (3H, d, J = 4.1 Hz, Me-27), 1.12 (3H, s, Me-18),
4
.3.2. Elephanoside B (6)
White amorphous powder, ½aꢂ ¼ ꢀ14:5 (c 0.61,
1.28 (1H, m, H-7b), 1.36 (1H, m, H-2a), 1.42 (1H, m, H-
14), 1.56 (3H, d, J = 6.7 Hz, Me-21), 1.66 (1H, m, H-24a),
1.69 (1H, m, H-9), 1.85 (1H, m, H-8), 1.88 (1H, m, H-2b),
2.03 (1H, m, H-23a), 2.06 (1H, m, H-25), 2.19 (1H, m, H-
24b), 2.20 (2H, m, H-5, 23b), 2.21 (2H, m, H-11a,20), 2.36
(1H, m, H-11b), 2.95 (1H, t, J = 7.6 Hz, H-17), 3.61 (1H,
m, H-26a), 3.85 (1H, m, GlcII H-5), 3.95 (1H, m, H-26b),
4.21 (1H, t, J = 9.2 Hz, GlcI H-4), 4.22 (1H, t, J = 9.2 Hz,
GlcII H-3), 4.28 (1H, m, H-3), 4.33 (1H, t, J = 9.2 Hz, GlcII
H-4), 4.39 (1H, m, Gal H-3), 4.57 (1H, br s, Gal H-4), 4.68
(1H, t, J = 8.8 Hz, Gal H-2), 4.83 (1H, d, J = 7.7 Hz, GlcII
H-1), 4.89 (1H, d, J = 7.7 Hz, Gal H-1), 4.93 (1H, m, H-16),
2
D
3
ꢀ
MeOH). FABMS (negative ion mode): m/z 1081 [MꢀH] ,
ꢀ
ꢀ
9
20 [MꢀGlc (162)] , 757 [MꢀGlc (162) · 2ꢀH] , 595
ꢀ
[
MꢀGlc (162) · 3ꢀH] . HRESIMS (negative ion mode):
ꢀ
m/z
1081.5445
[M(C H O )ꢀH]
(calcd.
for
5
1
86 24
1
1
081.5436). H NMR (pyridine-d , 500 MHz): d 0.86 (3H,
5
s, Me-18), 0.90 (1H, m, H-7a), 0.95 (3H, s, Me-19), 0.97
3H, d, J = 6.6 Hz, Me-27), 1.09 (1H, m, H-14), 1.14 (1H,
m, H-7b), 1.18 (1H, m, H-11a), 1.22 (1H, m, H-9), 1.26
1H, m, H-12a), 1.27 (1H, m, H-11b), 1.33 (3H, d,
(
(
J = 6.7 Hz, Me-21), 1.43 (2H, m, H-8,2a), 1.62 (1H, m,
H-24a), 1.69 (1H, m, H-12b), 1.87 (2H, m, H-2b, 25),
1
3
5.30 (1H, d, J = 7.6 Hz, GlcI H-1). C NMR (pyridine-d5,
2
.03 (3H, m, H-23a,b,24b), 2.04 (1H, m, H-17), 2.20 (1H,
400 MHz): see Tables 1 and 2.
m, H-5), 2.21 (1H, m, H-20), 3.60 (1H, dd, J = 4.5,
9
2
.5 Hz, H-26a), 3.81 (1H, m, GlcII H-5), 3.92 (1H, m, H-
6b), 4.15 (1H, t, J = 10.0 Hz, GlcI H-4), 4.20 (1H, t,
4.3.5. Elephanoside E (9)
2
D
3
White amorphous powder, ½aꢂ ¼ ꢀ14:1 (c 0.32,
ꢀ
ꢀ
J = 10.0 Hz, GlcIII H-4), 4.24 (1H, m, GlcI H-5), 4.29
1H, m, H-3), 4.37 (1H, m, Gal H-3), 4.78 (1H, br s, Gal
H-4), 4.79 (1H, m, Gal H-2), 4.81 (1H, d, J = 7.6 Hz, GlcII
MeOH). FABMS (negative ion mode): m/z 935 [MꢀH] ,
ꢀ
(
773 [MꢀGlc (162)ꢀH] , 609 [MꢀGlc (162) · 2–3H] .
HRESIMS (negative ion mode): m/z 935.4848

Y. Zhang et al. / Phytochemistry 69 (2008) 264–270
269
ꢀ
1
[
M(C H O )ꢀH] (calcd. for 935.4857). H NMR (pyr-
dryness to give monosaccharide mixtures for sugar detec-
4
5
76 20
idine-d , 400 MHz): d 0.89 (1H, m, H-7a), 0.96 (3H, d,
tion by HPTLC [n-BuOH–i-PrOH–H O (10:5:4, homoge-
5
2
J = 5.8 Hz, Me-27), 0.97 (3H, s, Me-19), 1.07 (1H, m, H-
nous), R values of glucose, xylose and galactose were
f
1
4), 1.13 (3H, s, Me-18), 1.19 (1H, m, H-7b), 1.42 (1H,
m, H-2a), 1.43 (1H, m, H-9), 1.48 (1H, m, H-8), 1.49
1H, m, H-11a), 1.56 (1H, m, H-15a), 1.62 (3H, d,
J = 6.6 Hz, Me-21), 1.69 (1H, m, H-24a), 1.78 (1H, m, H-
1b), 1.87 (1H, m, H-25), 1.88 (1H, m, H-2b), 2.03 (1H,
m, H-24b), 2.06 (1H, m, H-15b), 2.07 (2H, m, H-23a,b),
0.25, 0.40, 0.27, respectively]. The determination of the
absolute configuration of the sugars followed the proce-
dure described in our previous paper (Zhang et al., 2006).
The retention times of the corresponding trimethylsilylated
L-cysteine adducts of D-glucose, D-xylose, D-galactose,
L-glucose, L-xylose, and L-galactose were 17.96, 13.06,
18.75, 18.53, 13.72 and 19.31 min, respectively.
(
1
2
2
.15 (1H, m, H-5), 2.35 (1H, dd, J = 6.4, 8.2 Hz, H-17),
.48 (1H, m, H-20), 3.55 (1H, t, J = 5.6 Hz, H-12), 3.60
(
3
1H, dd, J = 6.0, 9.6 Hz, H-26a), 3.83 (1H, m, GlcII H-5),
.90 (1H, br t, J = 9.6 Hz, H-26b), 4.19 (1H, t,
J = 8.8 Hz, GlcII H-3), 4.20 (1H, t, J = 8.8 Hz, GlcII H-
), 4.29 (1H, m, H-3), 4.30 (1H, t, J = 8.4 Hz, GlcI H-4),
.33 (1H, m, Gal H-3), 4.56 (1H, br s, Gal H-4), 4.66
4.3.8. Enzymatic hydrolysis of compounds 6, 7, and 9
A solution of 6 (10 mg), 7 (10 mg) or 9 (20 mg) in H O
(2 ml, 2 ml, 4 ml, respectively) was hydrolyzed with b-glu-
cosidase from almonds (EC No. 2325897) (20 mg, 20 mg,
40 mg, respectively) at 37 ꢁC for 48 h, respectively. The
reaction mixtures were partitioned between n-BuOH and
2
4
4
(
1H, t, J = 8.4 Hz, Gal H-2), 4.80 (1H, d, J = 7.6 Hz, GlcII
H-1), 4.90 (1H, d, J = 7.6 Hz, Gal H-1), 5.06 (1H, m, H-
H O. The n-BuOH extracts of 6 and 7 were identical with
2
1
3
1
6), 5.28 (1H, d, J = 7.8 Hz, GlcI H-1). C NMR (pyri-
their corresponding spirostanol type compounds 2 and 3,
respectively, which were determined by direct co-TLC
detection [CHCl –MeOH–H O (7:3:0.5), R 0.35 and
dine-d , 400 MHz): see Tables 1 and 2.
5
3
2
f
4
.3.6. Elephanoside E (10)
White amorphous powder, ½aꢂ ¼ ꢀ24:8 (c 0.22,
0.32, respectively]. The n-BuOH extract of 9 (10 mg) was
subjected on a silica gel CC to afford a spirostanol saponin
(6 mg), which was identified to be (25R)-5b-spirostan-
3b,12b-diol-3-O-b-D-glucopyranosyl(1 ! 2)-b-D-galacto-
pyranoside (YS-XI) by comparison of its NMR spectra
with reported data (Nakano et al., 1991a). Co-TLC analy-
2
D
3
ꢀ
ꢀ
MeOH). FABMS (negative ion mode): m/z 1097 [MꢀH] ,
ꢀ
935 [MꢀGlc (162)ꢀH] , 773 [MꢀGlc (162) · 2ꢀH] .
HRESIMS (negative ion mode): m/z 1097.5355
ꢀ
1
[
(
M(C H O )ꢀH] (calcd. for 1097.5385). H NMR
5
1
86 25
pyridine-d , 500 MHz): d 0.89 (1H, m, H-7a), 0.96 (3H,
sis of the H O layer indicated the presence of glucose for all
5
2
s, Me-19), 0.97 (3H, d, J = 6.3 Hz, Me-27), 1.13 (3H, s,
Me-18), 1.17 (2H, m, H-7b, 14), 1.58 (1H, m, H-15a),
of the compounds 6, 7, and 9 (iso-propanol–MeOH–H O,
2
25:1:2, R 0.6).
f
1
1
2
.61 (3H, d, J = 6.8 Hz, Me-21), 1.70 (1H, m, H-24a),
.19 (1H, m, H-9), 1.51 (1H, m, H-8), 1.90 (1H, m, H-
5), 2.02 (1H, m, H-24b), 2.07 (2H, m, H-23a,b), 2.12
4.3.9. Antifungal and antibacterial bioassays
The testing organisms including Candida albicans ATCC
90028, Cryptococcus neoformans ATCC 90113, A. fumiga-
tus ATCC 90906, E. coli ATCC 35218, P. aeruginosa
ATCC 27853, and M. intracellulare ATCC 23068 were
obtained from the American Type Culture Collection
(Manassas, VA). The former five microbes were performed
using a modified version of the NCCLS methods (NCCLS,
2000,2002), while the last one was tested using a modified
method of Franzblau et al. (1998). The minimum inhibi-
tory concentration (MIC) is defined as the lowest test con-
centration that allows no detectable growth, while the
minimum fungicidal concentration (MFC) is defined as
the lowest test concentration that kills the organism.
(
1H, m, H-15b), 2.48 (1H, m, H-20), 2.21 (1H, m, H-5),
2
1
3
4
.34 (1H, t, J = 7.5 Hz, H-17), 3.54 (1H, dd, J = 4.5,
0.5 Hz, H-12), 3.61 (1H, dd, J = 6.0, 9.5 Hz, H-26a),
.91 (1H, m, H-26b), 4.15 (1H, t, J = 9.0 Hz, GlcI H-4),
.28 (1H, m, H-3), 4.79 (1H, br s, Gal H-4), 4.84 (1H, d,
J = 7.5 Hz, Gal H-1), 4.80 (1H, d, J = 8.0 Hz, GlcII
H-1), 5.06 (1H, m, H-16), 5.37 (1H, d, J = 7.8 Hz, GlcIII
H-1), 5.55 (1H, d, J = 7.7 Hz, GlcI H-1). C NMR (pyri-
1
3
dine-d , 500 MHz): see Tables 1 and 2.
5
4
.3.7. Acid hydrolysis of compounds 4, 8, and 10
Compounds 4, 8 or 10 (10 mg each) in 2 M HCl–dioxane
(
1:1, 2 ml) were individually heated at 95 ꢁC for 6 h. The
reaction mixture was diluted with H O and extracted with
2
CHCl . The CHCl phases of 4, 8 and 10 afforded (25R)-
Acknowledgments
3
3
5
(
b-spirostan-3b-ol (smilagenin) (Agrawal et al., 1985),
25R)-5b-spirostan-3b-ol-12-one (gloriogenin) (Nakano
et al., 1991b), and 12b-hydroxysmilagenin (Nakano et al.,
991a), respectively, which were identified by direct co-
The authors are grateful to the members of the Analyt-
ical Group in State Key Laboratory of Phytochemistry and
Plant Resources in West China, Kunming Institute of Bot-
any, for measurements of all spectra. This work was sup-
ported in part by the National Natural Science Fund of
China (grant no. U0632010), the grant NIH/NIAID AI
27094 and the USDA Agricultural Research Service spe-
cific cooperative agreement number 58-6408-2-009.
1
TLC comparison with authentic samples [petroleum ether:-
ethyl acetate (7:3), R 0.7, 0.4, and 0.2, respectively] and by
f
comparing their NMR data with published values. The
aqueous layer was passed through an Amberlite IRA-401
ꢀ
(
OH form) column, and the eluate was concentrated to

2
70
Y. Zhang et al. / Phytochemistry 69 (2008) 264–270
Nakano, K., Matsuda, E., Tsurumi, K., Yamasaki, T., Murakami, K.,
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