Hepatoprotective phenylethanoid glycosides from Cirsium setosum

Article abstract of DOI:10.1080/14786419.2015.1084304

Two new phenylethanoid glycosides, namely β-D-glucopyranoside, 1″-O-(7S)-7-(3-methoxyl-4-hydroxyphenyl)-7-methoxyethyl-3″-α-L-rhamnopyranosyl-4″-[(8E)-7-(3-methoxyl-4-hydroxyphenyl)-8-propenoate] (1) and β-D-glucopyranoside, 1″-O-(7S)-7-(3-methoxyl-4-hydr

Full text of DOI:10.1080/14786419.2015.1084304

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Hepatoprotective phenylethanoid glycosides from
Cirsium setosum
Qinge Ma, Yongming Guo, Baomin Luo, Wenmin Liu, Rongrui Wei, Chunxia
Yang, Chenghua Ding, Xuefeng Xu & Minghui He
To cite this article: Qinge Ma, Yongming Guo, Baomin Luo, Wenmin Liu, Rongrui Wei,
Chunxia Yang, Chenghua Ding, Xuefeng Xu & Minghui He (2015): Hepatoprotective
phenylethanoid glycosides from Cirsium setosum, Natural Product Research, DOI:
10.1080/14786419.2015.1084304
To link to this article: http://dx.doi.org/10.1080/14786419.2015.1084304
View supplementary material
Published online: 11 Sep 2015.
Submit your article to this journal
Article views: 5
View related articles
View Crossmark data
Full Terms & Conditions of access and use can be found at
http://www.tandfonline.com/action/journalInformation?journalCode=gnpl20
Download by: [University of Cambridge]
Date: 15 September 2015, At: 19:22

Natural Product research, 2015
ꢁꢁp://ꢂx.ꢂꢃi.ꢃꢄg/10.1080/14786419.2015.1084304
ꢀ
Hepatoprotective phenylethanoid glycosides from Cirsium
setosum
a
a
a
a
b
a
Qinge Ma , Yongming Guo , Baomin Luo , Wenmin Liu , Rongrui Wei , Chunxia Yang ,
a
a
a
Chenghua Ding , Xuefeng Xu and Minghui He
ꢅ
dꢆpꢅꢄꢁmꢆnꢁ ꢃf Gꢄꢅꢂꢇꢅꢁꢆ sꢁꢇꢂꢆnꢁꢈ, cꢃꢉꢉꢆgꢆ ꢃf cꢀꢆmiꢈꢁꢄy ꢅnꢂ Pꢀꢅꢄmꢅꢊꢆꢇꢁiꢊꢅꢉ enginꢆꢆꢄing, Nꢅnyꢅng Nꢃꢄmꢅꢉ
b
univꢆꢄꢈiꢁy, Nꢅnyꢅng, cꢀinꢅ; dꢆpꢅꢄꢁmꢆnꢁ ꢃf Pꢀꢅꢄmꢅꢊꢃꢉꢃgy, cꢃꢉꢉꢆgꢆ ꢃf Pꢀꢅꢄmꢅꢊy, cꢀinꢅ Pꢀꢅꢄmꢅꢊꢆꢇꢁiꢊꢅꢉ
univꢆꢄꢈiꢁy, Nꢅnjing, cꢀinꢅ
ABSTRACT
ARTICLE HISTORY
rꢆꢊꢆivꢆꢂ 20 Mꢅy 2015
aꢊꢊꢆpꢁꢆꢂ 28 Jꢇꢉy 2015
Two new phenylethanoid glycosides, namely β-D-glucopyranoside,
1
″-O-(7S)-7-(3-methoxyl-4-hydroxyphenyl)-7-methoxyethyl-3″
-
α-L-rhamnopyranosyl-4″-[(8E)-7-(3-methoxyl-4-hydroxyphenyl)
8-propenoate](1)andβ-D-glucopyranoside,1″-O-(7S)-7-(3-methoxyl-
KEYWORDS
Cirsium setosum;
pꢀꢆnyꢉꢆꢁꢀꢅnꢃiꢂ gꢉyꢊꢃꢈiꢂꢆ;
ꢀꢆpꢅꢁꢃpꢄꢃꢁꢆꢊꢁivꢆ ꢅꢊꢁiviꢁy
-
4
-hydroxyphenyl)-7-methoxyethyl-3″-α-L-rhamnopyranosyl-4″-
[(8E)-7-(4-hydroxyphenyl)-8-propenoate] (2), together with six
phenylethanoid glycosides were isolated from Cirsium setosum.
Their structures were elucidated by their spectroscopic data and
references. Compounds 2, 4, 5, 7 and 8 (10 μM) exhibited moderate
hepatoprotective activities. Compounds (3–8) were obtained from
this plant for the first time.
1
. Introduction
Cirsium setosum, belonging to the Asteraceae family, is well known as the name of ‘Ci-Er-Cai’.
It is widely distributed in China and has been used for thousands of years to treat haematuria,
spitting of blood and uterine bleeding (Jiang et al. 2013). Previous phytochemical studies have
revealed the presence of triterpenes (Li et al. 2012), lignans (Meng et al. 2009), flavonoids (Zhu &
Zhang 2007), volatile oils (Małgorzata, Marek et al. 2015) and steroids (Sun et al. 2012). Moreover,
CONTACT Qingꢆ Mꢅ
mꢅqingꢆ2006@163.ꢊꢃm
tꢀꢆ ꢈꢇppꢉꢆmꢆnꢁꢅꢉ ꢂꢅꢁꢅ fꢃꢄ ꢁꢀiꢈ ꢅꢄꢁiꢊꢉꢆ iꢈ ꢅvꢅiꢉꢅbꢉꢆ ꢃnꢉinꢆ ꢅꢁ ꢀꢁꢁp://ꢂx.ꢂꢃi.ꢃꢄg/10.1080/14786419.2015.1084304.
©
2015 tꢅyꢉꢃꢄ & Fꢄꢅnꢊiꢈ

2
Q. MA ET AL.
C. setosum exhibit various pharmacological activities such as anti-inflammatory (Yang et al.
2006), antibacterial (Małgorzata, Anna et al. 2015) and sedative (Jiang et al. 2013) activities.
To the best of our knowledge, there have been no reports on hepatoprotective activities of
C. setosum, which prompted us to investigate its further pharmacological potentials. During our
systematic investigation on its chemical constituents, eight compounds (Figure S1) were isolated
and identified from this plant. Among them, compounds 1 and 2 are two new phenylethanoid
glycosides, and compounds (3–8) are known phenylethanoid glycosides isolated from C. setosum
for the first time.Their structures were elucidated on the basis of the spectroscopic analysis and
the reported references. Moreover, we evaluated the hepatoprotective activities of compounds
(
3
1–8), which were tested against D-galactosamine induced toxicity in HL-7702 cells using a
-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric method (Ma
et al. 2013). Compounds 2, 4, 5, 7 and 8 (10 μM) exhibited moderate hepatoprotective activities.
2
. Results and discussion
2
.1. Structure elucidation
2
2
D
Compound 1 was obtained as a yellow solid, with mp 154.5–155.8 °C, [α] −4.5° (c 0.80,
MeOH), its UV (MeOH) spectrum showed absorbance at λ : 208, 288 and 330 nm. The molec-
max
+
ular formula of compound 1 was determined as C H O by HR-ESI-MS showed [M+Na] at
32
42 16
m/z 705.3581 (Calcd for C H O Na 705.3587), indicating 12° of unsaturation. The IR spec-
3
2
42 16
−1
−1
trum showed the presence of hydroxyl (3405.5 cm ), ester carbonyl (1742.0, 1710.4 cm )
and methyl (1385.7 cm ) functionalities.
−
1
1
The H NMR spectrum showed the presence of two ABX systems at δ 6.79 (1H, d, J = 1.5 Hz,
H
H-2), 6.68 (1H, d, J = 8.0, Hz, H-5), 6.63 (1H, dd, J = 8.0, 1.5 Hz, H-6) and 7.16 (1H, d, J = 1.5 Hz,
H-2′), 6.80 (1H, d, J = 8.0, Hz, H-5′), 7.02 (1H, dd, J = 8.0, 1.5 Hz, H-6′) (Table S1) in the aromatic
field, which revealed two 1,3,4-trisubstituted benzene rings in compound 1. Moreover, an
1
AB system at δ 7.64 (1H, d, J = 15.8 Hz, H-7′), 6.39 (1H, d, J = 15.8 Hz, H-8′) showed in the H
H
NMR spectrum, indicated a trans-double bond in compound 1. Therefore, we concluded that
the caffeoyl fragment (Nan et al. 2013) was contained in compound 1. In the middle field of
H NMR spectrum, there were two typical signals at δ 4.46 (1H, d, J = 7.5 Hz, H-7), 3.95 (2H,
m, H-8), corresponding to δ 83.4 (C-7), 72.9 (C-8) of the C NMR and HSQC spectra, which
indicated the segment of –CH –CHR– was in compound 1. The data of C NMR spectrum
1
H
13
C
13
2
at δ 130.9 (C-1), 113.6 (C-2), 148.7 (C-3), 147.1 (C-4), 116.7 (C-5), 122.2 (C-6), 83.4 (C-7), 72.9
C
(C-8) (Table S1) revealed the fragment of 3-methoxyl-4-hydroxyphenyl phenylethyl alcohol
in compound 1. Additionally, three typical methoxyl signals were observed at δ 3.86(s, 6H),
H
1
13
3
.23(s, 3H) and δ 56.8, 56.5 in the H NMR and C NMR spectra (Table S1).
C
1
3
The C NMR spectrum showed at δ 103.8 (C-1″), 101.8 (C-1″), 62.6 (C-6″), 18.1 (C-6″)
C
1
corresponding to the H NMR spectrum displayed at δ 4.56 (1H, d, J = 7.8 Hz, H-1″), 5.01
H
(
1H, d, J = 1.5 Hz, H-1″) and 1.24 (3H, d, J = 6.2 Hz, H-6″) which indicated the presence of
the glucose and the rhamnose in compound 1 (Table S1). The other correlating data of
1
1
compound 1 were confirmed by the experiment of HSQC, H- H COSY and DEPT spectra.
The planar structure of compound 1 was established on the basis of the correlations of H-6/
C-4; H-7/C-2, C-6; H-6′/C-4′; H-7′/C-6′,C-9′; H-1″/C-8; H-4″/C-9′; H-6″/C-5″; H-1″‘/C-3″ in the
HMBC spectrum (Figure S2), and relative configuration was determined by the correlations
of H-2/3-OCH , H-2′/3′-OCH , H-1″/7-OCH , H-5″/H-6″ in the NOESY spectrum (Figure S2).
3
3
3
2
2
D
We measured the optical rotation of compound 1 with value α = −3.6°, and its [α] = −4.5°,

NATURAL PRODUCT RESEARCH
3
22
[
M]22 −30.3°, Δ[M] = +89.5° (Yin & Liu 1997). The Δ[M]22 value of compound 1 was nearly
D
=
D
D
22
equal to Δ[M] = +89.7° of S-suspensaside methyl ether (Guo et al. 2007). Therefore, the C-7
D
configuration of compound 1 was identified as 7S. Based on the above spectral evidences,
the chemical structure of compound 1 was determined to be β-D-glucopyranoside, 1″-O-(7S)-
7
-(3-methoxyl-4-hydroxyphenyl)-7-methoxyethyl-3″-α-L-rhamnopyranosyl-4″-[(8E)-7-
(
3-methoxyl-4-hydroxyphenyl)-8-propenoate].
Compound 2 was isolated as a yellow solid, with mp 152.7–153.1 °C, [α] −4.7° (c 0.80,
2
2
D
MeOH), its molecular formula was established as C H O based on HR-ESI-MS at m/z
3
1
40 15
+
6
75.5341 [M + Na] (Calcd for C H O Na, 675.5348), indicating 12° of unsaturation. Its UV
31 40 15
(
MeOH) spectrum showed absorbance at λ : 207, 288, 331 nm and IR spectrum indicated
max
−
1
−1
the presence of hydroxyl (3398.7 cm ), ester carbonyl (1743.4, 1711.8 cm ) and methyl
(
−1
1388.0 cm ) functionalities. According to the data of HR-ESI-MS, UV and IR spectra, com-
pound 2 was concluded to be an analogue (Nan et al. 2013) of compound 1.
1
In the H NMR spectrum, an AA′BB′ system at δ 7.40 (2H, d, J = 8.0 Hz, H-2′,6′), 6.78 (2H, d,
H
J = 8.0 Hz, H-3′,5′) and an ABX system at δ 6.81 (1H, d, J = 1.5 Hz, H-2), 6.67 (1H, d, J = 8.0 Hz,
H-5), 6.64 (1H, d, J = 8.0, 1.5 Hz, H-6) (Table S1) were observed in the aromatic proton field. All
the fragments of compound 2 were connected by the experiments of DEPT, HSQC, HMBC and
H
1
1
H- H COSY spectra shown in Figure S2. In a similar way, the optical rotation of compound
2
2
D
22
22
2
(
was measured with value α = −3.8°, and its [α] = −4.7°, [M]
−30.6°, Δ[M] = + 89.6°
D =
D
Yin & Liu 1997). The Δ[M]22 value of compound 2 was nearly equal to Δ[M] = +89.7° of
22
D
D
S-suspensaside methyl ether (Guo et al. 2007). Therefore, the C-7 configuration of compound
2
was identified as 7S. Consequently, compound 2 was determined as β-D-glucopyranoside,
1
″-O-(7S)-7-(3-methoxyl-4-hydroxyphenyl)-7-methoxyethyl-3″-α-L-rhamnopyranosyl-4″-
[
(8E)-7-(4-hydroxyphenyl)-8-propenoate].
Additionally, other six known phenylethanoid glycosides were isolated and identified as
cistanoside D (3) (Gross & Sticher 1987), acteoside (4) (Gross & Sticher 1987), β-D-glucopyra-
noside, 1″-O-7-(4-hydroxyphenyl)-7-ethyl-6″-[(8E)-7-(3,4-dihydroxyphenyl)-8-propenoate]
(
5) (Hiroko et al. 1987), calceolarioside B, (6) (Ersöz et al. 2002), dunalianoside C (7) (Zhao
et al. 2008) and dunalianoside D (8) (Zhao et al. 2008) by comparison of their physical and
spectroscopic data with those reported in the references.
2
.2. Hepatoprotective activity
Compounds (1–8) were evaluated for their hepatoprotective activities against
d-galactosamine-induced HL-7702 cell damage. As a result, compounds 2, 4, 5, 7 and 8
(
10 μM) showed moderate hepatoprotective activities (Table S2).
3
. Experimental
3
.1. General procedures
The melting points were recorded on a XT5B microscopic melting point apparatus (BeijingTech
electro-optical instrument factory, China) which were uncorrected. The optical rotations were
measured on a Perkin-Elmer 241 polarimeter at 20 °C. The UV spectra were measured with an
Australia GBC UV-916 spectrophotometer, and a Nicolet 5700 FT-IR spectrometer was used
for scanning IR spectroscopy using KBr pellets. HR-ESI-MS data were measured using a Q-Trap
LC/MS/MS (Turbo Ionspray Source) spectrometer. 1D and 2D NMR spectra were recorded on

4
Q. MA ET AL.
Bruker-400 withTMS as internal standard. Reversed-phase HPLC was performed using Agilent
200 series with a DIKMA (4.6 × 250 mm) analytical column packed with C18 (5 μm). Column
1
chromatography was performed on Sephadex LH-20 (Amersham Pharmacia, Sweden), silica
gel H, 100–200 mesh and 200–300 mesh (Qingdao Marine Chemical Inc., Qingdao, China). TLC
was performed on precoated silica gel GF254 plates, and the spots were visualised under UV
light (254 or 356 nm) or by spraying with 10% H SO in 95% EtOH followed by heating.
2
4
3
.2. Plant material
The whole plant of C. setosum was collected from Xixia Country, Henan Province, China in
October 2013. A voucher specimen (NO. NNU-201310) has been deposited in Nanyang Normal
University. The plant material was dried, finely powdered and used for the successive extraction.
3
.3. Extraction and isolation
The whole air-dried and powdered plant of C. setosum (10.0 kg) was extracted three times
with 95% EtOH (15 L × 3) heating under reflux to give 1.2 kg of crude extract (Almeida
et al. 2011). The combined extracts were successively partitioned with petroleum ether, ethyl
acetate and n-butanol to yield three fractions: petroleum ether soluble fraction (104.5 g),
ethyl acetate soluble fraction (188.4 g) and n-butanol soluble fraction (268.2 g). According
to the results of bioassay-guided investigation of C. setosum, we found that the n-butanol
soluble fraction showed potential hepatoprotective activity.
The n-butanol soluble fraction was performed on the macroporous adsorbent resin
(
Diaion-101) column, which was eluted with 20, 40, 60 and 95% ethanol to obtain four frac-
tions: A (34.7 g), B (78.6 g), C (27.4 g) and D (13.5 g). The A part was purified on a Sephadex
LH-20 column with a gradient system of MeOH/H O to give three sub-fractions: A–a, A–b,
2
A–c. The separation of A–b (9.6 g) by silica gel (100–200 mesh or 200–300 mesh), repeatedly,
yielded 4 (12.30 mg), 5 (11.25 mg) and 7 (13.20 mg). The A–c part was repeatedly chroma-
tographed over Sephadex LH-20 and silica gel, successively, yielded 1 (8.52 mg), 2 (9.06 mg)
and 3 (11.65 mg). Similarly, The B part was chromatographed over Sephadex LH-20 and
silica gel (100–200 mesh or 200–300 mesh) eluting with different mobile phases, yielded 6
(11.20 mg) and 8 (10.66 mg). The structures of these compounds (1–8) are shown in Figure S1.
3
.4. Acid hydrolysis of compounds 1–8
Compounds 1–8 (5 mg each) were treated in 5% HCl (0.5 mL) and heated at 90 °C for 2 h,
respectively (Chang & Case 2005). After cooling, each reaction mixture was extracted with
EtOAc, and the aqueous layer was neutralised with 0.1 M NaOH. As a result, glucose and rham-
nose were obtained from compound (1–4), which were detected by thin layer chromatography
(
TLC) with authentic sugars. Similarly, we obtained glucose from compounds (5–8). The type of
glucose and rhamnose were identified by TLC method with authentic sugars (Ma et al. 2014).
3
.5. Hepatoprotective assay
The compounds (1–8) were evaluated for their hepatoprotective activities against
D-galactosamine-induced toxicity in HL-7702 cells using a MTT colorimetric method.The HL-7702
cell lines were cultured in Dulbecco’s modified Eagle’s medium (DMEM) supplemented with 3%

NATURAL PRODUCT RESEARCH
5
foetal calf serum, 100 units/mL penicillin and 100 units/mL streptomycin in 5% CO and incubated
2
at 37 °C, which were placed in a 96-well microplate and precultured for 24 h (Hsiao et al. 2013).
The cultured cells were measured for cytotoxic effects which exposed to 40 mM D-galactosamine
after 24 h. At last, the medium was replaced for the serum-free medium (0.5 mg/mL MTT) for
3.5-h incubation.The medium was removed and added DMSO (150 μL/well) into the microplate,
and the formazan crystals were redissolved. The optical density (OD) was measured by a
microplate reader at a wavelength of 492 nm, and the inhibition was calculated as inhibition
(%) = [(OD(sample) − OD(control))/(OD(normal) − OD(control))] × 100 (Liu et al. 2012).
3
.6. Statistical analysis
We had evaluated the pharmacological activities of compounds (1–8) with the bicyclol
hepatoprotective activity drug) as the positive control for their hepatoprotective activities
(
against D-galactosamine-induced toxicity in HL-7702 cells. The results of hepatoprotective
activities were given in Table S2. The percentage of inhibition of compounds 2, 4, 5, 7 and 8
(
10 μM) were calculated using the following formula: inhibition (%) = [(OD(sample) − OD(control)
)
/
(OD(normal) − OD(control))] × 100, respectively. Moreover, all the values were expressed as
means ± SD of three experiments. The significance of unpaired observations between nor-
mal or control and tested samples was determined by Student’s t-test (Ma et al. 2014). The
differences were considered significant at p < 0.05. Consequently, compounds 2, 4, 5, 7 and 8
(
10 μM) showed moderate hepatoprotective activities.
4
. Conclusion
In this work, eight phenylethanoid glycosides (1–8) were isolated and identified from
C. setosum. Compounds 1 and 2 were new phenylethanoid glycosides, compounds (3–8)
were obtained from this plant for the first time. Among them, compounds 2, 4, 5, 7 and 8
(
10 μM) exhibited moderate hepatoprotective activities.
Acknowledgements
We express our appreciation to the Department of Instrumental Analysis of Nanyang Normal University
for the UV, IR, NMR and MS. This work was supported by the Key Scientific Research Project of Colleges
and Universities in Henan Province (NO.15A350009), the Special Project of Nanyang Normal University
(
NO.ZX2014044), the Graduate Students′ Case Teaching Course Construction Project of Nanyang
Normal University (NO.ALJX201502), and the Ideological and Political Education Project of Nanyang
Normal University (NO.SZ2014015).
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was supported by the Key Scientific Research Project of Colleges and Universities in Henan
Province [grant number 15A350009]; Special Project of Nanyang Normal University [grant number
ZX2014044]; Graduate Students’ Case Teaching Course Construction Project of Nanyang Normal
University [grant number ALJX201502]; Ideological and Political Education Project of Nanyang Normal
University [grant number SZ2014015].

6
Q. MA ET AL.
Supplementary material
Experimental details relating to this article are available online, alongside Figures S1–S2 and Tables
S1–S2.
References
Almeida JRGS, de Lima JT, de Oliveira HR, de Oliveira MR, Meira PRM, Lúcio ASSC, Barbosa Filho
JMB, Quintans Júnior LJQ. 2011. Antinociceptive activity of discretamine isolated from Duguetia
moricandiana. Nat Prod Res. 25:1908–1915.
Chang J, Case R. 2005. Phenolic glycosides and ionone glycoside from the stem of Sargentodoxa
cuneata. Phytochemistry. 66:2752–2758.
Ersöz T, Tašdemï D, Çališ Ï. 2002. Phenylpropanoid glucosides from Scutellaria galericulata. Turkish J
Chem. 26:465–471.
Gross GA, Sticher O. 1987. Phenylpropanoid glycosides isolated from Scrophularia scopolii.
Phytochemistry. 26:2057–2061.
Guo H, Liu AH, Li L, Guo DA. 2007. Simultaneous determination of 12 major constituents in Forsythia suspensa
by high performance liquid chromatography-DAD method. J Pharm Biomed Anal. 43:1000–1006.
Hiroko S, Yutaka S, Tokuo A. 1987. Cyanogenic and phenylpropanoid glucosides from Prunus grayana.
Phytochemistry. 26:2363–2366.
Hsiao PC, Liaw CC, Hwang SY, Cheng HL, Zhang LJ, Shen CC, Hsu FL, Kuo YH. 2013. Antiproliferative
and hypoglycemic cucurbitane-type glycosides from the fruits of Momordica charantia. J Agric Food
Chem. 61:2979–2986.
Jiang H, Meng YH, Yang L, Wang QH, Yang BY, Liu C, Kuang HX. 2013. A new megastigmane glycoside
from the aerial parts of Cirsium setosum. Chin J Nat Med. 11:534–537.
Li LL, Sun Z, Shang XY, Li JJ, Wang R, Zhu J. 2012. Triterpene compounds from Cirsium setosum. Chin J
Chin Mater Med. 37:951–955.
Liu YF, Liang D, Luo H, Hao ZY, Wang Y, Zhang CL, Zhang QJ, Chen RY, Yu DQ. 2012. Hepatoprotective
iridoid glycosides from the roots of Rehmannia glutinosa. J Nat Prod. 75:1625–1631.
Małgorzata K, Anna B, Anna M, Marcin C. 2015. Chemical compositions and antibacterial activity of
extracts obtained from the inflorescences of Cirsium canum (L.) all. Nat Prod Res. 29:2059–2063.
doi:10.1080/14786419.2015.1030341
Małgorzata K, Marek M, Joanna K. 2015. Chemical composition and variability of the volatile components
from inflorescences of Cirsium species. Nat Prod Res. 29:1942–1944. doi:10.1080/14786419.2015.1010165
Ma QG, Tian J, Yang JB, Wang AG, Ji TF, WangYG, SuYL. 2013. Bioactive carbazole alkaloids from Murraya
koenigii (L.) Spreng. Fitoterapia. 87:1–6.
Ma QG, Wang YG, Liu WM, Wei RR, Yang JB, Wang AG, Ji TF, Tian J, Su YL. 2014. Hepatoprotective
sesquiterpenes and rutinosides from Murraya koenigii (L.) Spreng. J Agric Food Chem. 62:4145–4151.
Meng YH, Wang QH, Jiang H, Yang BY, Kuang HX. 2009. Study on chemical constituents of Herba cirsii.
Zhong Yao Cai. 32:58–61.
Nan ZD, Zeng KW, Shi SP, Zhao MB, JiangY,Tu PF. 2013. Phenylethanoid glycosides with anti-inflammatory
activities from the stems of Cistanche deserticola cultured in Tarim desert. Fitoterapia. 89:167–174.
Sun Z, Li LL, Yuan ZZ, Wang AL, Li JJ, Shang XY. 2012. Isolation, purification and structural elucidation
of steroids from Cirsium setosum (wild.) MB. Food Sci. 33:124–127.
Yang XH, Cui JH, Ding AW. 2006. Impact of Herba cirsii extracts on hemorrhage, blood coagulation and
experimental inflammation in rats. J Tradit Chin Med. 24:17–19.
Yin YY, Liu CY. 1997. The structure and calculation of rotation of monosaccharide. Chem Res App.
9:629–636.
Zhao P, Tanaka T, Hirabayashi K, Zhang YJ, Yang CR, Kouno I. 2008. Caffeoyl arbutin and related
compounds from the buds of Vaccinium dunalianum. Phytochemistry. 69:3087–3094.
Zhu D, Zhang JW. 2007. Study on extraction technology of flavonoids in Herba cirsii. J Anhui Agric Sci.
35:1262–1263.