Steroidal saponins from the rhizomes of Polygonatum odoratum

Article abstract of DOI:10.1080/14786410902750977

Three steroidal saponins were isolated and characterised from the rhizomes of Polygonatum odoratum. The structure of the compounds were determined as 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-galactopyranosyl-25

Full text of DOI:10.1080/14786410902750977

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Steroidal saponins from the rhizomes
of Polygonatum odoratum
Dongmei Wang a , Dengwu Li, Wei Zhu a , Jingfang Zhang a & Pai
Peng a
a College of Forestry, Northwest Sci-Tech University of Agriculture
and Forestry, Yangling, 712100, P.R. China
Version of record first published: 29 Oct 2009.
To cite this article: Dongmei Wang, Dengwu Li, Wei Zhu, Jingfang Zhang & Pai Peng (2009):
Steroidal saponins from the rhizomes of Polygonatum odoratum , Natural Product Research:
Formerly Natural Product Letters, 23:10, 940-947
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Natural Product Research
Vol. 23, No. 10, 10 July 2009, 940–947
Steroidal saponins from the rhizomes of Polygonatum odoratum
*
Dongmei Wang, Dengwu Li , Wei Zhu, Jingfang Zhang and Pai Peng
College of Forestry, Northwest Sci-Tech University of Agriculture and Forestry, Yangling 712100,
P.R. China
(Received 19 November 2008; final version received 15 January 2009)
Three steroidal saponins were isolated and characterised from the rhizomes
of Polygonatum odoratum. The structure of the compounds were determined
as 3-O-ꢀ-D-glucopyranosyl-(1 ! 2)-[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-D-glucopyran-
osyl-(1 ! 4)-galactopyranosyl-25(S)-spirost-5(6)-en-3ꢀ-ol (1), 3-O-ꢀ-D-glucopyr-
anosyl-(1 ! 2)-[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-D-glucopyranosyl-(1 ! 4)-galact-
opyranosyl-25(S)-spirost-5(6),14(15)-dien-3ꢀ-ol (2) and 3-O-ꢀ-D-glucopyranosyl-
(1 ! 2)-[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-D-glucopyranosyl-(1 ! 4)-galactopyra-
nosyl-25(S)–spirost-5 (6)-en-3ꢀ, 14ꢁ-diol (3). Compound 2 was identified as a
new compound. Compounds 1–3 were found to be strong against the growth
of bacteria and plant pathogenic fungi.
Keywords: Polygonatum odoratum; steroidal saponins; antisepsis activities
1. Introduction
Polygonatum odoratum (Liliaceae) is widely distributed in the central and southwest
areas of China. Its rhizome, also called ‘Yuzhu’, is a famous traditional Chinese
medicine and health food (Heller & Tammn, 1981; Sup, Hee, Jiyong, Na, & Jeong,
2004). The chemical constituents of rhizomes of several Polygonatum species have been
studied, and the isolation and identification of steroidal saponins have also been
reported by several groups (Choi & Park, 2002; Hang, Gan, Wu, & Lin, 1997; Jin,
Zhang, Li, & Yang, 2004; Li, Yang, Matsuura, Kasai, & Yamasaki, 1993; Qin, Li, &
Wang, 2003; Qin, Li, Wang, & Si, 2004; Sugiyama, Nakano, Tomimatsu, & Nohara,
1984; Yestlada & Peter, 1991; Zhang et al., 2006). Further phytochemical analysis of
the water-soluble steroidal glycoside constituents led to the isolation of three steroidal
saponins and one new saponin, which was determined as 3-O-ꢀ-D-glucopyranosyl-(1 ! 2)-
[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-D-glucopyranosyl-(1 ! 4)-galactopyranosyl-25(S)-spirost-5
(6),14(15)-dien-3ꢀ-ol (2), and two known saponins, named 3-O-ꢀ-D-glucopyranosyl-(1 ! 2)-
[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-D-glucopyranosyl-(1 ! 4)-galactopyranosyl-25(S)-spir-
ost-5(6)-en-3ꢀ-ol (1) and 3-O-ꢀ-D-glucopyranosyl-(1 ! 2)-[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-
D-glucopyranosyl-(1 ! 4)-galactopyranosyl-25(S)-spirost-5(6)-en-3ꢀ,14ꢁ-diol (3). This
article describes the isolation and structure determination of the three steroidal
saponins by detailed analysis of their 1D and 2D NMR spectra. The antisepsis
activities of compounds 1–3 are also discussed.
*Corresponding author. Email: dengwuli@163.com
ISSN 1478–6419 print/ISSN 1029–2349 online
ß 2009 Taylor & Francis
DOI: 10.1080/14786410902750977
http://www.informaworld.com

Natural Product Research
941
2. Results and discussion
2.1. Structure elucidation of compounds 1–3
Compounds 1 and 3 were identified as 3-O-ꢀ-D-glucopyranosyl-(1 ! 2)-[ꢀ-D-xylopyrano-
syl-(1 ! 3)]-ꢀ-D-glucopyranosyl-(1 ! 4)-galactopyranosyl-25(S)-spirost-5(6)-en-3ꢀ-ol
(Son & Do, 1990), and 3-O-ꢀ-D-glucopyranosyl-(1 ! 2)-[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-D-
glucopyranosyl-(1 ! 4)-galactopyranosyl-25(S)-spirost-5(6)-en-3ꢀ,14ꢁ-diol (Son & Do,
1990), respectively, based on their NMR spectral data and by comparison of their
physical properties with those reported in literature. Compound 3 was isolated from
P. odoratum as a mixture of 25 (R) and 25(S)-epimeric paris (Lin, Han, & Liao, 1994).
However, we excluded the possibility that 3 is the mixture of 25(R) and 25(S)-epimers by
NMR spectrum.
Compound 2 was obtained as a white amorphous powder, reacted positively to
Liebermann–Burchard and negatively to Ehrlich reagents, suggesting that 2 was a
22
steroidal saponin. ½ꢁꢀD : ꢁ53ꢂ (c ¼ 0.037, EtOH). Its molecular formula was assigned as
C50H78O22 on the basis of the NMR data, HR-MALDI-MS (m/z 1053.48770
[M þ Na]þ) and MALDI-MS (m/z 1053.3 [M þ Na]þ). IR showed strong absorption
band for hydroxy group at 3350 cmꢁ1 and characteristic bands for spiroketal moiety
at 990, 925, 890, 860 cmꢁ1 [intensity 925 4 890, 25(S)-spiroketal] (Lin et al., 1994).
Compound 2 gave D-glucose, D-xylose and D-galactose on acid hydrolysis, identified by
comparison with an authentic sample. The sugar portion was examined by TLC and
1
GLC analysis. The signals attributable to the aglycone part in the H NMR and 13C
NMR spectrum (Tables 1 and 2) of compound 2 seemed to be essentially analogous to
that of yamogenin (Son & Do, 1990), but there were two double bonds at ꢂ 158.41 (C)
and 119.04 (CH) for Á14(15), 140.55 (C) and 121.45 (CH) for Á5(6). The 1H NMR
spectrum of compound 2 showed two olefinic protons at ꢂ 5.53 (1H, br s) for Á14(15)
and 5.41 (1H, br s) for Á5(6) were in accordance with the above data obtained from
13C NMR and DEPT spectrum (Table 2). The 1H NMR and HMBC spectrum
(Table 1) also showed two singlet methyl signals at ꢂ 0.98 and 1.14, and two doublet
methyl signals at ꢂ 1.16 (J ¼ 7.1 Hz) and 1.25 (J ¼ 6.7 Hz), which were recognised as
typical steroidal methyls. The proton signals of C-26 were observed at ꢂ 4.15 (1 H, m,
26-Ha) and 3.48 (1 H, d ¼ 9.18, H-26b), the difference (Áab) of the proton signals of
C-26 was 0.67, which suggested that the configuration of the C-25 of 2 is S (Zhang
et al., 2006). Moreover, there was a quaternary carbon signal at ꢂ 107.40 (C) and four
methyl group signals at ꢂ 19.32 (CH3), 18.83 (CH3), 16.43 (CH3) and 14.59 (CH3),
respectively. In the HMBC spectrum, the position of the two double bond groups were
determined by correlations from the H-15 protons at ꢂ 5.53 to C-13 (ꢂ 46.81,C), C-16
(85.01,CH) and C-17 (59.72, CH), H-18 protons at ꢂ 1.14 to C-12 (ꢂ 43.56, CH2), C-13
(46.81, C), C-14 (158.41, C) and C-17(59.72, CH), H-6 protons at ꢂ 5.41 to C-4
(39.29, CH2), C-8 (31.51, CH), C-10 (37.89, C), H-19 protons at ꢂ 0.98 to C-1
(ꢂ 37.36, CH2), C-5 (140.55, C) and C-9 (52.56, CH), and showed the two double
bond groups at Á14(15) and Á5(6), respectively. These results were further supported that
the aglycone of compound 2 confirmed the Á14(15)–yamogenin structure.
A detailed comparison of 1H NMR and 13C NMR signals (Tables 1 and 3) for
compounds 1, 2 and 3, showed that the saccharide chain is identical in all compounds.
Signals for four anomeric protons of compound 2 at ꢂ 5.66 (1 H, d, J ¼ 7.18 Hz), 5.45
(1 H, d, J ¼ 7.80 Hz), 5.32 (1 H, d, J ¼ 7.76 Hz), 5.26 (1 H, d, J ¼ 7.83 Hz), were diagnostic
of ꢀ-configuration of all the four sugars. 13C NMR and DEPT spectrum (Table 3) of

942
D. Wang et al.

Natural Product Research
943
Table 2. 13C NMR data (chemical shifts [ppm]) for the aglycone of compounds 1–3 (Pyridine-d5,
100 MHz).
1
2
3
Position
ꢂ
DEPT
ꢂ
DEPT
ꢂ
C
DEPT
C
C
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
37.60
32.29
79.98
39.99
141.16
121.73
30.10
31.77
50.41
37.16
21.23
32.40
40.56
56.76
39.37
81.30
62.85
19.51
16.47
42.59
14.99
109.86
26.52
26.33
27.67
65.22
16.43
CH2
CH2
CH
CH2
C
CH
CH2
CH
CH
C
37.36
29.56
79.98
39.29
140.55
121.45
30.19
31.51
52.56
37.89
21.53
43.56
46.81
158.41
119.04
85.01
59.72
19.32
18.83
45.58
14.59
107.40
29.55
26.31
27.76
65.51
16.43
CH2
CH2
CH
CH2
C
CH
CH2
CH
CH
C
37.84
30.30
80.01
39.40
140.66
122.33
26.79
35.72
43.71
37.50
20.52
32.08
45.20
86.55
40.03
82.11
59.86
20.16
19.44
42.68
15.32
110.18
26.70
26.40
27.70
65.20
16.45
CH2
CH2
CH
CH2
C
CH
CH2
CH
CH
C
CH2
CH
C
CH2
CH2
C
CH2
CH2
C
CH2
CH2
CH
CH
CH3
CH3
CH
CH3
C
CH2
CH2
CH
CH2
CH3
C
C
CH
CH
CH
CH3
CH3
CH
CH3
C
CH2
CH2
CH
CH2
CH3
CH2
CH
CH
CH3
CH3
CH
CH3
C
CH2
CH2
CH
CH2
CH3
compound 2 showed four anomeric carbons at ꢂ 105.29 (CH), 105.09 (CH), 104.98 (CH)
1
and 102.94 (CH) were in accordance with the above data obtained from the H NMR
spectrum, and suggested the existence of four sugar units attached to the aglycone. In the
13C NMR, a common downfield shift (þ7.98 ppm) for C-3 of the aglycone moiety
compared with that of yamogenin, together with an upfield shift of C-2 and C-4 revealed
that the sugar chain must be attached at the C-3 position of the aglycone. The chemical
shifts of the anomeric carbon signals confirmed that all the sugar units were substituted on
C-1. The HMBC spectrum also showed correlations of D-galactose anomeric proton at ꢂ
5.26 to C-3 (79.98), D-xylose anomeric proton at ꢂ 5.32 to C00-3 (86.91), D-glucose anomeric
proton at ꢂ 5.45 to C0-4 (77.88), the other D-glucose anomeric proton at ꢂ 5.66 to C00-2
(81.46), showed the D-galactose was directly attached to the C-3 of aglycone. These results
strongly suggest the sugar moiety to be ꢀ-D-lycotetraose, a well-known tetrasaccharide
from various plant sources, as a sugar moiety of the saponins. On the basis of the above
findings, the structure of compound 2 was determined to be 3-O-ꢀ-D-glucopyranosyl-
(1 ! 2)-[ꢀ-D-xylopyranosyl-(1 ! 3)]-ꢀ-D-glucopyranosyl-(1 ! 4)-galactopyranosyl-25(S)-
spirost-5(6),14(15)-dien-3ꢀ-ol (Figure 1). This saponin has not been reported previously;
such an aglycone or its derivatives have not been reported before.

944
D. Wang et al.
Table 3. 13C NMR data (chemical shifts [ppm]) for the sugar moieties of compounds 1–3 (Pyridine-
d5, 100 MHz).
1
2
3
Position
ꢂ
DEPT
ꢂ
DEPT
ꢂ
C
DEPT
C
C
Gla-10
20
102.88
73.30
75.21
77.74
75.69
60.69
104.96
81.45
86.93
70.60
77.88
62.62
105.08
75.45
78.78
70.87
76.34
63.11
105.26
75.21
78.86
71.18
67.47
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH
102.94
73.32
75.21
77.88
76.36
60.66
104.98
81.46
86.91
70.87
78.35
62.63
105.09
75.68
78.80
71.18
77.75
63.10
105.29
75.44
78.80
70.61
67.48
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH2
102.82
73.32
75.21
77.74
76.35
60.69
104.96
81.46
86.93
70.87
78.79
62.61
105.08
75.45
78.33
71.17
77.88
63.10
105.28
75.69
78.86
70.60
67.47
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH
CH2
CH
CH
CH
CH
CH2
30
40
50
60
Glc-100
200
300
400
500
600
Glc-1000
2000
3000
4000
5000
6000
Xyl-10000
20000
30000
40000
50000
It is interesting to note that all of these steroidal saponins possess the sugar sequence
of ꢀ-lycotetraose, a well-known tetrasaccharide at the hydroxyl group of C-3. The only
difference is observed at the aglycone moieties.
2.2. Antisepsis activity of compounds 1–3
The compounds 1–3 were tested for their antisepsis activity at a concentration 10 mg mLꢁ1
.
The results showed that the compounds 1–3 had strong inhibition against Exserohilum
turcicum growth: the inhibition rate was 84.36, 80.28 and 78.24%, respectively.
Compounds 1 and 2 had strong inhibition against Bacillus cereus and Corynebacterium
sepedonium growth, respectively; diameter of inhibition circle was between 10–13 mm.
Compound 3 only had certain inhibition against Escherichia coli growth in tested
bacteriums; the diameter of inhibition circle was 10 mm.
3. Experimental
3.1. General
Optical rotations were measured with a Perkin–Elmer 341 sensitive polarimeter at 22ꢂC.
IR (KBr) spectra was measured on Happ–Genzel. NMR spectra were recorded on a

Natural Product Research
945
CH
3
O
CH
3
CH
3
O
CH
14
3
15
R
CH OH
2
O
O
O
CH OH
5
O
2
O
6
HO
O
O
H
HO
HO
HO
OH
H
H
OH
CH OH
2
O
HO
HO
OH
H
1
R=H
R=Δ14(15)
2
3
R=OH
Figure 1. Chemical structures of compounds 1–3.
Bruker DRX-400, using TMS as an internal standard. MALDI-MS data were obtained on
a WBG-P-346 CHCA AS MATRIX. ESI-MS data were obtained on an Agilent XCT trap.
FAB-MS data were obtained on a VG AutoSpec-3000 mass spectrometer. HR-MALDI-
MS data were obtained on a WBG-9-34 Sephadex LH-20 (Amersham Biosciences). ODS-
A silica-gel (YMC). GLC was performed on a HP 5890 Series II. Detection was done by
spraying the plates with 5% anisaldehyde-sulphuric acid, followed by heating.
3.2. Plant
The P. odoratum rhizomes were collected in the Qinling mountains in September 2005.
The voucher specimen (No. 65) has been deposited at the Herbarium of the Northwest
Sci-Tech University of Agriculture and Forestry.
3.3. Extraction and isolation
The air-dried rhizomes of P. odoratum (17 kg) were extracted with 95% EtOH at room
temperature. The extract was concentrated under vacuum to give a brown waxy residue.
The residue was partitioned between water and EtOAc. The water fraction was further
extracted with n-butanol. The evaporated n-butanol extract was performed on macro-
porous resin D101 and eluted with a gradient mixture of EtOH : H2O(3 : 7, 6 : 4, 1 : 0), to
give three fractions. Fraction 3 (125.4 g) was chromatographed on a silica gel column
eluted with a gradient CHCl3 : MeOH (20 : 1, 15 : 1, 10 : 1, 5 : 1 and 1 : 1) to afford sub-
fractions 1–5. Sub-fraction 4 was rich in steroidal saponins. Further chromatography of
sub-fraction 4 on a silica gel column eluted with a gradient CHCl3 : MeOH (5 : 1, 3 : 1, 1 : 1)
and repeatedly RP-18 eluted with a gradient MeOH/H2O to yield compound 1 (84 mg),
compound 2 (40 mg) and compound 3 (64 mg).

946
D. Wang et al.
3.4. TLC and GLC analysis for sugar residues
Each compound (5.0 mg) was treated in 1 M HCl (dixane : H2O, 1 : 1, 2 mL) at 100ꢂC
H2O bath for 6 h. The reaction mixture was neutralised with 1 M NaOH and filtered
(Zhang et al., 2006; Lin et al., 1994). The filtrate was partitioned four times between
CHCl3 and H2O. The H2O layer was identified by direct comparison with an authentic
sugar sample on TLC. D-Glucose, D-xylose and D-galactose were detected in each
compound as the common sugars. The sugar portion was examined by TLC
[CHCl3 : MeOH : Me2CO : H2O(3 : 3 : 3 : 1)]
to
detect
methyl
galactopyranoside
(Rf ¼ 0.31), methyl glucopyranoside (Rf ¼ 0.35) and methyl-D-xylopyranoside
(Rf ¼ 0.55). Then, the H2O layer fraction was evaporated to dryness with a N2
stream. The residue was trimethylsilylated with a mixture of pyridine (5 mL) and
trimethylchlorosilane (0.5 mL) at room temperature for 30 min, and then subjected to
GLC analysis (Lin et al., 1994). Identification of peaks was made by comparing with
those of the reaction product of an authentic sugar. tR (min): D-Gal (6.84), D-Glu(7.24)
and D-Xyl(2.42), the ratio of its high peak was 1 : 2 : 1. GLC conditions: SE-30 column
(I.D 0.22 mm ꢃ 12 m); carrier gas, N2; flow rate, 30 mL minꢁ1; detection, FID,
temperature, 270ꢂC; column temperature, 180ꢂC.
3.5. Acid hydrolysis of compound 2
Compound 2 (7 mg) was refluxed with 1 M HCl (dixane : H2O, 1 : 1, 2 mL) at 100ꢂC H2O
bath for 6 h. The reaction mixture was evaporated to dryness. The dry reaction mixture
was partitioned four times between CHCl3 and H2O. The CHCl3 layer was concentrated
and subjected to silica gel CC to provide 2a (1.8 mg): White amorphous powder; 1H NMR
(CDCl3, 75MHz) : ꢂ 0.93 (3H, s, Me-19), 1.10 (3H, s, Me-18), 1.10 (3H, d, J ¼ 7.1 Hz,
Me-27), 1.21 (3H, d, J ¼ 6.9 Hz, Me-21), 5.39 (1H, brs, H-6), 5.49 (1H, brs, H-15). FAB-
MS (negative mode) m/z: 411 [M ꢁ H]ꢁ,393 [M ꢁ H–H2O]ꢁ.
22
Compound 1: White amorphous powder, ½ꢁꢀD : ꢁ24.5ꢂ (c ¼ 0.215, EtOH). HR-MALDI-
MS (positive): m/z 1055.50576 [M þ Na]þ. Calcd 1055.50390. MALDI-MS (positive): m/z
1055.6 [M þ Na]þ, 923.5 [M þ Na-xyl-OH]þ.
22
Compound 2: White amorphous powder, ½ꢁꢀD ¼ ꢁ53ꢂ (c ¼ 0.037, EtOH). HR-MALDI-
MS (positive): m/z 1053.48770 [M þ Na]þ. Calcd 1053.48826. MALDI-MS (m/z): 1053.3
[M þ Na]þ.
22
Compound 3: White amorphous powder, ½ꢁꢀD ¼ ꢁ88.5ꢂ (c ¼ 0.012, EtOH). ESI-MS
(positive): m/z 1071.6 [M þ Na]þ, 593.3 [M þ H-xyl-2glu]þ, 395.2 [M þ H-xyl-2glu-gal-
2H2O]þ. ESI-MS (negaitive): m/z 1047.9 [M ꢁ H]ꢁ.
3.6. Antisepsis activity
Three bacterials (E. coli, B. cereus, C. sepedonium) and two plant pathogenics
(E. turcicum, Alternaria brassicae) were collected in the microbe laboratory of
Northwest A&F University, and were identified by Li Xiao-Ming, a senior laboratorian.
The growth of the hyphae method was adopted to study the compound against plant
fungicidal and a filter paper-diffuse method was adopted to study the bacterial activities

Natural Product Research
947
(Wang, Zhu, Zhang, & Ni, 2006). Every treatment was repeated three times, and cultivated
for 96 h at 28.8ꢂC in a constant temperature culture box.
Acknowledgements
We wish to acknowledge the financial support from the National Natural Science Foundation
of China (No. 30671672), the Program for Youth Bakebone Talents of Northwest A&F University,
the Program for Youth Foundation of Northwest A&F University (07ZR013) and supported by
Scientific Research Foundation for Doctors, Northwest A&F University (01140505).
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