Paeonidanins F-H: Three new dimeric monoterpene glycosides from Paeonia lactiflora and their anti-inflammatory activity

Article abstract of DOI:10.1016/j.phytol.2015.08.003

Abstract Three new dimeric monoterpene glycosides, paeonidanins F-H (1-3) were isolated from the roots of Paeonia lactiflora. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1-3 showed inhibitory effects against nitric oxide (NO) and pro-inflammatory cytokine TNF-α release in LPS-induced RAW 246.7 macrophages.

Full text of DOI:10.1016/j.phytol.2015.08.003

Phytochemistry Letters 13 (2015) 386–389
Contents lists available at ScienceDirect
Phytochemistry Letters
journal homepage: www.elsevier.com/locate/phytol
Short communication
Paeonidanins F–H: Three new dimeric monoterpene glycosides from
Paeonia lactiflora and their anti-inflammatory activity
Qiang Fu , Tian Yu , Hai-Mei Yuan , Yu Songb,c, Liang Zoub,*
a
b
a
a
Faculty of Biotechnology Industry, Chengdu University, Chengdu 610106, China
School of Basic Medical Sciences & Nursing, Chengdu University, Chengdu 610106, China
College of Pharmacy, Dali University, Dali 671000, Yunnan, China
b
c
A R T I C L E I N F O
A B S T R A C T
Article history:
Three new dimeric monoterpene glycosides, paeonidanins F–H (1–3) were isolated from the roots of
Paeonia lactiflora. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis
products. Compounds 1–3 showed inhibitory effects against nitric oxide (NO) and pro-inflammatory
Received 21 April 2015
Received in revised form 11 July 2015
Accepted 1 August 2015
Available online xxx
cytokine TNF-
a release in LPS-induced RAW 246.7 macrophages.
ã 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
Keywords:
Dimeric monoterpene glycosides
Paeonidanins F–H
Anti-inflammatory activity
1. Introduction
2. Results and discussion
Substantial efforts have been put on the investigation of “cage-
like” monoterpene glycosides in past decades due to their
production of diversified structures and biological activities. Many
The EtOH extract of dried roots of P. lactiflora was subjected to
silica gel column chromatography and prep-HPLC to obtain three
new compounds (1–3). Their structures were elucidated on the
basis of spectroscopic evidence and hydrolysis products. The
inhibitory effects against nitric oxide (NO) and pro-inflammatory
“
cage-like” monoterpene derivatives were isolated and reported
from plants, such as from genus Paeonia. These compounds
exhibited anticoagulant, anti-inflammatory, antihyperglycemic,
analgesic, and antithrombotic activities (He et al., 2004; Tsuboi
et al., 2004; Duan et al., 2009; Fu et al., 2013).
cytokine TNF-a release in LPS-induced RAW 246.7 macrophages of
all compounds were also evaluated.
The molecular formula of compound 1 was found to be
ꢀ
Paeonia lactiflora Pall. is a well-known ornamental plant with
ornate flowers blooming in spring in mainland China. Its dried
roots have been used in traditional Chinese medicine for a long
time, with claims being made of its antispasmodic, anti-
inflammatory, tonic, astringent, and analgesic properties (Baum-
gartner et al., 2010). Previous chemical investigations on this plant
afforded a series of monoterpene derivatives (Wang et al., 2009; Fu
et al., 2013; Zou et al., 2015). In our continuing effort to seek the
interesting monoterpenes from genus Paeonia, a re-investigation
on the roots of P. lactiflora led to the discovery of three new dimeric
analogues, paeonidanins F–H.
C
46
H
54
O
21 [(M–H) , m/z 941.3072, calcd for C46
H
53
O
21, 941.3079]
1
13
by HR-ESIMS. The H, C NMR (Table 1) and heteronuclear
multiple quantum coherence (HMQC) spectra of 1 revealed that 1
0
00
contained two methyl groups (C-10 and C-10 ), four methylenes
0
00
000
0
000
(C-3, C-7, C-3 , and C-7 ), four oxymethylene (C-8, C-6 , C-8 , and
0
000
000
0
C-6 ), two methines (C-5 and C-5 ), ten oxymethines (C-9, C-2 –
C-5 , C-2 –C-5 , and C-4 ), two anomeric carbons (C-1 and
C-1 ), ten aromatic carbons (C-2 –C-6 , and C-2 –C-6 ), two
quaternary aromatic carbons (C-1 , and C-1 ), four quaternary
0
0000
0000
000
0
0
000
00
00
00000
00000
0
0
00000
oxygenated carbons (C-1, C-2, C-1”', and C-2”') and two quaternary
0
00
carbons (C-6, and C-6 ), one carbonyl carbon (C-4), and three ester
0
0
00000
000
Herein, we report the isolation and structure elucidation, and
anti-inflammatory activity of these compounds.
carbons (C-7 , C-7 , and C-9 ).
1
1
A detailed analysis of the H– H correlated spectroscopy (COSY)
spectrum of 1 allowed to elucidate the following six partial
0
0
00
00
000
000
0000
structures: C-5–C-7, C-1 –C-3 , C-2 –C-6 , C-5 –C-7 , C-1 –C-
0
000
00000
00000
3
, and C-2 –C-6 . The heteronuclear multiple bond correla-
tions (HMBC) 3H-10/C-1, C-2 and C-3; H-5/C-6, C-7 and C-8; H -7/
C-1, C-5 and C-6; 2H-8/C-5, C-6 and C-9; and H-9/C-6 (Fig. 2)
indicated that the partial structure of C-1–C-10 was the same as the
b
*
Corresponding author at: School of Basic Medical Sciences & Nursing, Chengdu
University, Shiling Town, Chengdu 610106, China.
E-mail address: zouliang@cdu.edu.cn (L. Zou).
http://dx.doi.org/10.1016/j.phytol.2015.08.003
1874-3900/ã 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

Q. Fu et al. / Phytochemistry Letters 13 (2015) 386–389
387
Table 1
1
H spectral data of compounds 1 and 2 (500 MHz, in CD
3
OD).
2
Position
1
1
2
d
H
d
H
d
H
d
H
0
0
0
0
0
0
0
0
00
00
00
00
00
00
00
00
0
3
3
5
7
7
8
8
9
a
b
2.51 d (18.0)
2.94 d (18.0)
2.84 d (5.0)
1.88 d (12.0)
2.92 dd (12.0, 5.0)
4.71 d (12.5)
4.81 d (12.5)
5.32 s
1.41 s 3H
4.57 d (7.5)
3.15 dd (9.0, 7.5)
3.32 dd (9.0, 7.5)
3.14 m
2.50 d (18.0)
2.93 d (18.0)
2.85 d (4.5)
1.86 d (12.0)
2.91 dd (12.0, 4.5)
4.71 d (12.0)
4.81 d (12.0)
5.32 s
1.40 s 3H
4.55 d (7.0)
3.16 dd (9.0, 7.0)
3.33 dd (9.0, 7.0)
3.12 m
3
3
4
5
7
7
8
8
a
b
2.01 d (12.0)
2.80 d (12.0)
4.24 d (5.0)
2.01 d (12.0)
2.79 d (12.0)
4.23 d (5.0)
2.91 m
2.03 d (14.0)
2.38 dd (14.0 5.0)
3.95 s 2H
a
b
a
b
2.92 m
a
b
a
2.05 d (15.0)
2.39 dd (15.0 5.0)
4.66 d (12.0)
4.80 d (12.0)
1.52 s 3H
b
00
1
0
10
1.51 s 3H
4.20 d (7.0)
3.13 dd (9.0, 7.0)
3.22 dd (9.0, 7.5)
3.19 m
3.21 m
3.68 dd (12.0, 6.0)
3.78 dd (12.0, 2.0)
0
0
0
0
0
0
0
0
0
0
0000
0000
1
2
3
4
5
6
6
2
3
4
1
2
3
4
5
6
6
2
3
4
4.22 d (7.5)
3.12 dd (9.0, 7.5)
3.24 dd (9.0, 7.5)
3.20 m
0000
0000
0000
0000
0000
00000 00000
00000 00000
00000
3.22 m
3.20 m
3.22 m
a
3.61 dd (12.0, 6.0)
3.89 dd (12.0, 2.0)
8.01 d (7.5) 2H
7.49 t (7.5) 2H
7.58 t (7.5)
3.61 dd (12.0, 6.0)
3.89 dd (12.0, 2.0)
8.02 d (7.5) 2H
7.49 t (7.5) 2H
7.57 t (7.5)
a
b
,6
,5
3.68 dd (12.0, 6.0)
3.78 dd (12.0, 2.0)
8.06 d (7.5) 2H
7.47 t (7.5) 2H
7.60 t (7.5)
b
0
00
00
,6
,5
0
0
corresponding section of paeonidanin (Okasaka et al., 2008). The
0
00
000
000
000
000
000
000
HMBC signals between 3H-10 /C-1 , C-2 and C-3 ; H-5 /C-4 ,
0
00
000
000
000
000
000
000
C-6 and C-9 ; 2H-8 /C-5 and C-9 ; and H-4 /C-3 , C-5 and
0
00
C-7 (Fig. 2) indicated the presence of partial structure of albiflorin
13
(
Yen et al., 2007). The 1H and C NMR data as well as acid
hydrolysis and GC comparison with an authentic sample indicated
the presence of a D-glucose moiety. The -configuration of the
b
glycosidic linkage was determined from the coupling constant of
the anomeric proton. Sugar-aglycone linkages were determined by
HMBC data analysis.
0
0
00
00
00
The signals at
C
d 131.2 (C-1 ), 130.6 (C-2 , C-6 ), 129.6 (C-3 ,
0
0
00
00
00000
C-5 ), 134.2 (C-4 ) and 167.7 (C-7 ), and 131.2 (C-1 ), 130.6
C-2 , C-6 ), 129.6 (C-3 , C-5 ), 134.2 (C-4 ) and 167.8
C-7 ) disclosed the presence of two sets of benzoyl units. The
0
0000
00000
00000
00000
00000
(
(
0
0000
connections between the benzoyl moiety and aglycone were
0
0
000
00000
confirmed by HMBC correlations H
2
-8/C-7 and H
2
-8 /C-7
.
Above information suggested that compound 1 was a dimer
comprising a paeonidanin unit and an albiflorin unit. The HMBC
0
000
0000
correlations from H-9 to C-6 indicated that C-6 of paeonidanin
was connected to C-9 of albiflorin through an oxygen atom.
The configurations of the stereogenic centers in the monoter-
pene units were assigned by comparison to the spectra of related
compounds (Okasaka et al., 2008; Yen et al., 2007) and were
confirmed by the ROESY spectrum. The ROESY spectrum also
showed cross-correlations between the pairs of protons H-9/H-8,
0
0
000
000
000
000 000 000 000
000
000
H-1 /H-7
a, H-7 a/H-8 a, H-7 a/H-5 , H-8 a/H-5 , and
H-6 /H-3. Thus, the structure of 1 was determined as shown in
Fig. 1, and named paeonidanin F.
The molecular formula of compound 2 was found to be
ꢀ
C
39
H
50
O
20 [(M–H) , m/z 837.2813, calcd for C39
49
H O
20, 837.2817]
by HR-ESIMS. Comparison of the NMR data for 2 and 1 revealed
that the compounds are similar, except for the absence of signals
0
00
for benzoyl moiety connected with C-8 in 1. This was confirmed
Fig. 1. The structures of compounds 1–3.
0
00
by the C-8 appeared comparatively upfield at
d 59.9. Therefore,
the structure of 2 was determined as shown in Fig. 1, and named
paeonidanin G.
moieties. Comparison of the NMR data for 3 and paeonidanin E
revealed that the compounds are similar, except for the appearance
The molecular formula of compound 3 was found to be
0
of signals for benzoyl moiety connected with C-6 in 3. This was
ꢀ
C
1
53
H
58
O
22 [(M–H) , m/z 1045.3349, calcd for
C
53
57
H O
22
,
0
000
0
confirmed by the HMBC correlation H-6 /C-7 , and the C-6
appeared comparatively downfield at 65.1. Therefore, the
13
045.3342] by HR-ESIMS. The C NMR data suggested that
d
compound 3 was a dimer comprising paeonidanin and paeoni-
structure of 3 was determined as shown in Fig. 1, and named
paeonidanin H.
1
13
florin structural moieties. The H and C NMR spectra showed a
striking resemblance to those of paeonidanin E (Duan et al., 2009),
with common signals of two monoterpene systems and benzoyl
All isolates were evaluated for inhibitory activity against
LPS-induced nitric oxide (NO) and TNF-
a production in RAW

3
88
Q. Fu et al. / Phytochemistry Letters 13 (2015) 386–389
3
.3. Extraction and isolation
The dried roots of P. lactiflora (2.6 kg) were refluxed two times
with EtOH, each for 2 h. After concentrated in vacuo, the residue
321 g) was suspended in water, and partitioned with ethyl acetate
(
and n-butanol successively. The n-butanol-soluble fraction (105 g)
was further chromatographed over a silica gel column chroma-
tography using CHCl
fractions 1–5. Fraction 1 (5.3 g) was subjected to ODS open column
chromatography (MeOH–H
O, 10:90 ! 95:5) to afford sub-frac-
tions 1–6 (0.3, 0.8, 0.1, 0.4, 1.7 and 0.6 g, respectively). Sub-fraction
(0.8 g) was separated by prep-HPLC (MeOH–H O, 50:50, UV
detection at 230 nm, 2.0 ml/min) to yield compound 2 (29 mg, t
24.7 min). Sub-fraction 5 (1.7 g) was subjected to prep-HPLC
(MeOH–H O, 48:52, UV detection at 230 nm, 2.0 ml/min) to afford
compounds 1 (37 mg, t 18.0 min). Fraction 5 (6.7 g) was subjected
to C18 silica gel chromatography (MeOH–H
O, 10:90 ! 95:5) to
afford sub-fractions 1–4 (2.2, 0.7, 0.8 and 0.9 g, respectively). Sub-
fraction 2 (0.7 g) was separated by prep-HPLC (MeOH–H O, 47:53,
UV detection at 230 nm, 2.0 ml/min), affording compound 3
(33 mg, t 25.1 min).
3
–MeOH (100:1 !10:90) as an eluent to give
2
Fig. 2. Selected HMBC correlations of compound 1.
2
2
2
46.7 macrophages. Compounds 1–3 significantly suppressed NO
production. Curcumin was used as positive control. The IC50 values
of compounds 1–3 and curcumin were 22.7,19.4, 29.1 and 12.5 M,
respectively. However, those compounds showed weak inhibitory
effects against TNF- production with the inhibition ratios of 27%,
2%, and 19.5% at 50 M, respectively. No cytotoxicity was
observed in compounds 1–3 treated cells (cell viability >90%).
R
m
2
R
a
2
2
m
2
3
. Experimental
R
3.1. General experimental procedures
3.3.1. Paeonidanin F (1)
2
5
White, amorphous powder; [
a
]
D
ꢀ61.7 (c 0.2, MeOH); UV
ꢀ1
Optical rotations were measured on a JASCO P-1020 digital
(MeOH)
lmax (log e), 230 (4.20) nm; IR (KBr) vmax (cm ): 3439,
1
13
polarimeter (Jasco, Tokyo, Japan). Spots were visualized by
spraying 10% H SO –EtOH followed by heating. IR spectra were
2632, 1712, 1382, 1270 and 1071; H and C NMR spectral data, see
Tables 1 and 2.
2
4
obtained on a Bruker IFS-55 plus spectrometer (Bruker, Ettlingen,
German). UV spectra were recorded on a SHIMADZU UV-2201 UV–
vis recording spectrophotometer (Shimadzu, Kyoto, Japan). NMR
spectra were recorded on an Inova 500 spectrometer with TMS as
3.3.2. Paeonidanin G (2)
2
5
White, amorphous powder, [
a
]
D
ꢀ65.2 (c 0.2, MeOH); UV
ꢀ1
13
(MeOH) max (log ) 229 (4.20) nm IR (KBr) vmax (cm ): 3442,
l
e
1
1
an internal standard, operating at 500 MHz for Hand 125 MHz for
2630, 1709, 1380, 1270 and 1072; H and C NMR spectral data, see
Tables 1 and 2.
13
C (Bruker, Waltham, MA, USA). HR-ESIMS data were obtained on
a Bruker-Daltonics APES-III 7.0 TESLA FTMS spectrometer (Bruker,
Billerica, MA, USA). GC was obtained on a SHIMADZU GC-14D.
Precoated silica gel GF254 plates (Qingdao Haiyang Chemical Co.,
Qingdao, China) were employed for thin layer chromatography.
Column chromatography was performed with silica gel (Merck,
Darmstadt, Germany) and C18 silica gel (150–200 mesh, Merck).
High performance liquid chromatography (HPLC) separation was
carried out on an octadecylsilanized column (YMC-pack ODS-A,
3.3.3. Paeonidanin H (3)
2
5
White, amorphous powder, [
a
]
D
ꢀ64.6 (c 0.15, MeOH); UV
ꢀ1
13
(MeOH) max (log ) 228 (3.90) nm IR (KBr) vmax (cm ): 3440,
l
e
1
2632, 1706,1382,1272 and 1072; H and C NMR spectral data, see
Table 3.
3.4. Acid hydrolysis
2
50 ꢁ10 mm, i.d. 5
mm, YMC, Kyoto, Japan) with a photo-diode
ꢂ
array detector (Waters, Millford, MA, USA).
Each compound (5 mg) was heated in 0.5 ml of 2 M HCl at 95 C
for 10 h in a sealed tube. After filtration of the reaction mixture, the
3.2. Plant material
2
filtrate was evaporated under vacuum. After addition of H O, the
acidic solution was evaporated again to remove HCl. This
procedure was repeated until a neutral solution was obtained,
which was finally evaporated and dried in vacuo to furnish a
monosaccharide residue. The sugar components obtained after
acid hydrolysis of 1–3 were analyzed by GC analysis of the methyl
The roots of P. lactiflora were collected in Chengdu, Sichuan
Province, China, in May 2014, and identified by author (Qiang Fu). A
voucher specimen (PL 201403) is maintained in the herbarium of
Faculty of Biotechnology Industry, Chengdu University.
Table 2
1
3C spectral data of compounds 1 and 2 (125 MHz, in CD
3
OD)
Position
1
2
Position
1
2
Position
1
2
Position
1
2
d
C
d
C
d
C
d
C
d
C
d
C
d
C
d
C
0
000
000
000
000
000
000
000
000
0000
0000
0000
0000
0000
0000
00000
00000 00000
1
2
3
4
5
6
7
8
9
88.6
87.4
49.8
208.4
47.9
65.1
27.5
63.6
107.5
20.7
88.6
87.5
49.8
208.4
48.0
65.2
27.6
63.7
107.4
20.8
1
99.9
75.2
78.1
71.8
77.8
62.8
131.2
130.6
129.6
134.2
167.7
100.0
75.2
78.1
71.8
77.8
1
2
3
4
5
6
7
8
93.2
86.7
41.6
68.4
41.5
56.7
28.4
62.0
178.0
20.4
93.2
86.8
41.5
68.3
41.6
1
2
3
4
5
6
1
2
3
4
7
100.1
74.8
78.1
71.6
76.7
100.2
74.8
78.2
71.6
76.7
69.4
0
2
0
3
0
4
0
5
0
0
0
6
62.8
57.0
69.5
0
0
0
0
0
1
131.2
130.7
129.6
134.2
167.6
28.5
59.9
178.1
20.4
131.2
130.6
129.6
134.2
167.8
00
00
2 ,6
,6
,5
0
000
00000 00000
00000
00000
3 ,5
9
0
0
000
10
4
7
10

Q. Fu et al. / Phytochemistry Letters 13 (2015) 386–389
389
Table 3
3
.5. Assay for inhibitory activity against LPS-induced NO production
1
H and 13C spectral data of compound 3 (500 MHz, in CD
3
OD)
Position
3
Position
3
Tested compounds were separately dissolved in DMSO, and
diluted with phosphate buffered saline (PBS) to a final concentra-
tion of 10 mM. Such solution was then diluted to various test
concentrations. RAW 264.7 macrophages were seeded in 24-well
d
H
d
C
d
H
d
C
0
0
0
0
0
0
0
0
0
0
0
0
0
00
1
2
88.6
87.4
49.8
1
2
3
4
7
1
2
3
3
4
5
6
7
7
8
8
9
131.3
130.6
129.7
134.6
168.0
89.2
00 000
00 000
00
00
000
000
000
000
000
000
000
000
,6
,5
7.92 d (7.5) 2H
7.41 t (7.5) 2H
7.52 t (7.5)
5
3
3
4
5
6
7
7
8
8
9
a
2.50 d (18.0)
2.94 d (18.0)
plates (1 ꢁ10 cells/well), with cells co-incubated with the test
b
compounds and lipopolysaccharide (LPS, 1 mg/ml) for 24 h. The
208.5
48.0
65.1
27.5
amount of NO was assessed by determining the nitrite concentra-
tion in the cultured RAW 264.7 macrophage supernatants with
2.85 d (5.0)
87.4
44.5
Griess reagent. Aliquots of supernatants (100
in sequence, with 50 l 1% sulphanilamide and 50
naphthylethylenediamine in 2.5% H PO solution. Absorbances
m
l) were incubated,
a
b
a
b
1.87 d (12.0)
2.92 dd (12.0, 5.0)
4.70 d (12.5)
4.82 d (12.5)
5.30 s
1.40 s 3H
4.56 d (7.5)
3.22 dd (9.0, 7.5)
3.37 dd (9.0, 7.5)
3.35 m
a
b
1.75 d (12.0)
2.52 d (12.0)
m
m
l 0.1%
63.6
106.5
43.7
72.2
22.8
3
4
2.40 d (7.5)
at 570 nm were read using a microtiter plate reader.
107.5
20.7
100.1
74.9
77.8
1
0
a
b
a
b
1.92 d (12.0)
2.43 dd (12.0, 7.5)
4.56 d (12.0)
4.66 d (12.0)
5.37 s
1.28 s 3H
4.22 d (7.5)
3.13 dd (9.0, 7.5)
3.26 dd (9.0, 7.5)
3.20 m
0
0
0
0
0
0
0
0
0
0
0
0
0000
0000
0000
0000
3.6. Assay for inhibitory activity against LPS-induced TNF-
production
a
1
2
3
4
5
6
6
1
2
3
4
7
61.7
72.1
75.2 10
65.1
102.3
19.5
100.0
74.8
78.1
71.6
RAW 264.7 macrophages were seeded in 96 well plates
0000
3.58 m
4.50 dd (12.0, 6.0)
4.64 dd (12.0, 2.0)
5
00000
(1 ꢁ10 cells/well). Cells were co-incubated with drugs and
a
1
2
3
4
5
6
6
1
2
3
4
7
00000
00000
00000
00000
00000
00000
0
0
0
0
0
b
lipopolysaccharide (LPS, 1 mg/ml) for 24 h. TNF-a production
0
131.2
130.8
129.6
134.2
167.7
levels were determined using a commercially available TNF-a
ELISA kit (BioLegend, Inc., CA) according to the protocol provided
by the manufacturers.
0
00
00
,6
,5
8.01 d (7.5) 2H
7.49 t (7.5) 2H
7.58 t (7.5)
0
0
0
3.24 m
3.69 dd (12.0, 6.0)
3.80 dd (12.0, 2.0)
76.8
69.4
a
b
00000
00000 000000
00000 000000
00000
00000
131.2
130.8
129.9
134.6
168.0
References
,6
,5
8.05 d (7.5) 2H
7.49 t (7.5) 2H
7.62 t (7.5)
Baumgartner, R.R., Steinmann, D., Heiss, E.H., Atanasov, A.G., Gznzera, M.H.,
Stuppner, H., Dirsch, V.M., 2010. Bioactivity-guided isolation of 1,2,3,4,6-penta-
O-galloyl-d-glucopyranose from Paeonia lactiflora roots as a PTP1B inhibitor. J.
Nat. Prod. 73, 1578–1581.
Duan, W.J., Yang, J.Y., Chen, L.X., Zhang, L.J., Jiang, Z.H., Cai, X.D., Zhang, X., Qiu, F.,
2
009. Monoterpenes from Paeonia albiflora and their inhibitory activity on nitric
oxide production by lipopolysaccharide-activated microglia. J. Nat. Prod. 72,
579–1584.
sugar peracetates. The monosaccharide residue was dissolved in
anhydrous pyridine (100 ml), 0.1 M -cysteinemethyl ester hydro-
1
L
Fu, Q., Wang, S.B., Zhao, S.H., Chen, X.J., Tu, P.F., 2013. Three new monoterpene
glycosides from the roots of Paeonia lactiflora. J. Asian Nat. Prod. Res. 15,
chloride (200 ml) was added, and the resultant was warmed at
6
97–702.
ꢂ
6
0 C for 2 h. The trimethylsilylation reagent HMDS–TMCS
He, X.H., Xing, M., Ding, Y., Li, Y.P., Xu, L.Z., Du, L.J., 2004. Effects of cerebral ischemia-
reperfusion on pharmacokinetic fate of paeoniflorin after intravenous
administration of Paeoniae radix extract in rats. J. Ethnopharmacol. 94, 339–344.
Okasaka, M., Kashiwada, Y., Kodzhimatov, O.K., Ashurmetov, O., Takaishi, Y., 2008.
Monoterpene glycosides from Paeonia hybrida. Phytochemistry 69, 1767–1772.
Tsuboi, H., Hossain, K., Akhand, A.A., Takeda, K., Du, J., #i, Rifa#1, Dai, M., Hayakawa,
Y., Suzuki, A., Nakashima, I., 2004. Paeoniflorin induces apoptosis of
lymphocytes through a redox-linked mechanism. J. Cell Biochem. 93, 162–172.
Wang, H.B., Gu, W.F., Chu, W.J., Zhang, S., Tang, X.C., Qin, G.W., 2009. Monoterpene
glucosides from Paeonia lactiflora. J. Nat. Prod. 72, 1321–1324.
(
hexamethyldisilazane–trimethylchlorosilane–pyridine, 2:1:10;
ꢂ
Acros Organics, Geel, Belgium) was added and warmed at 60 C
for 30 min. To the mixture, the thiazolidine derivatives were
analyzed by GC for sugar identification. Separations were carried
out on a DB-5 column (30 m ꢁ 0.25 mm ꢁ 0.25 mm). Highly pure N
2
was employed as carrier gas (1.0 ml/min flow rate), and the flame
ꢂ
ionization detector detector operated at 280 C (column initial
ꢂ
Yen, P.H., Kiem, P.V., Nhiem, N.X., Tung, N.H., Quang, T.H., Minh, C.V., Kim, J.W., Choi,
E.M., Kim, Y.H., 2007. A new monoterpene glycoside from the roots of Paeonia
lactiflora increases the differentiation of osteoblastic MC3T3-E1 cells. Arch.
Pharm. Res 30, 1179–1185.
temperature was maintained at 100 C for 2 min and then raised to
ꢂ
ꢂ
2
80 C at the rate of 10 C/min). The retention time of the
D-glucose
derivative was 12.30 min.
Zou, L., Hu, L.F., Guo, Y.D., Song, Y., Fu, Q., 2015. Lipoxygenase-inhibiting phenolic
glycosides and monoterpene glycosides from Paeonia lactiflora. J. Asian Nat.
Prod. Res. doi:http://dx.doi.org/10.1080/10286020.2015.1007960 in press.