New lignan from the rattan stems of Schisandra chinensis

Article abstract of DOI:10.1080/14786419.2018.1452000

A new lignan named schilignan F (1), together with twelve known ones (2–13), were isolated from the rattan stems of Schisandra chinensis. Their chemical structures were elucidated by spectroscopic methods including one and two-dimensional NMR spectra referring to the literatures as well as high-resolution mass spectrometric analysis. All compounds were evaluated for their cytotoxicities against human Hela cancer cell lines in vitro. The results showed that compounds 2, 6 and 8 exhibited weak cytotoxic activity with IC₅₀ values of 30.6, 86.3 and 41.0?μM, and cisplatin showed cytotoxic activity with IC₅₀ value of 27.3?μM.

Full text of DOI:10.1080/14786419.2018.1452000

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
New lignan from the rattan stems of Schisandra
chinensis
Bing-You Yang, Zhang-Lin Chen, Yan Liu, Jiang-Tao Guo & Hai-Xue Kuang
To cite this article: Bing-You Yang, Zhang-Lin Chen, Yan Liu, Jiang-Tao Guo & Hai-Xue Kuang
(2018): New lignan from the rattan stems of Schisandra chinensis, Natural Product Research, DOI:
10.1080/14786419.2018.1452000
To link to this article: https://doi.org/10.1080/14786419.2018.1452000
View supplementary material
Published online: 16 Mar 2018.
Submit your article to this journal
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

Natural Product research, 2018
ꢁꢁpꢂ://ꢃꢄi.ꢄꢅg/10.1080/14786419.2018.1452000
ꢀ
New lignan from the rattan stems of Schisandra chinensis
a
a
a
b
a
Bing-You Yang , Zhang-Lin Chen , Yan Liu , Jiang-Tao Guo and Hai-Xue Kuang
ꢆ
Kꢇy lꢆbꢄꢅꢆꢁꢄꢅy ꢄf cꢀinꢇꢂꢇ Mꢆꢁꢇꢅiꢆ Mꢇꢃiꢈꢆ, hꢇiꢉꢄngjiꢆng univꢇꢅꢂiꢁy ꢄf cꢀinꢇꢂꢇ Mꢇꢃiꢈinꢇ, Miniꢂꢁꢅy ꢄf
b
eꢃꢊꢈꢆꢁiꢄn, hꢆꢅbin, Pꢇꢄpꢉꢇ’ꢂ rꢇpꢊbꢉiꢈ ꢄf cꢀinꢆ; Gꢊi Yꢆng cꢄꢉꢉꢇgꢇ ꢄf tꢅꢆꢃiꢁiꢄnꢆꢉ cꢀinꢇꢂꢇ Mꢇꢃiꢈinꢇ, Gꢊiyꢆng,
Pꢇꢄpꢉꢇ’ꢂ rꢇpꢊbꢉiꢈ ꢄf cꢀinꢆ
ABSTRACT
ARTICLE HISTORY
A new lignan named schilignan F (1), together with twelve known
ones (2–13), were isolated from the rattan stems of Schisandra
chinensis. Their chemical structures were elucidated by spectroscopic
methods including one and two-dimensional NMR spectra referring to
the literatures as well as high-resolution mass spectrometric analysis.
All compounds were evaluated for their cytotoxicities against human
Hela cancer cell lines in vitro. The results showed that compounds 2, 6
and 8 exhibited weak cytotoxic activity with IC values of 30.6, 86.3
rꢇꢈꢇivꢇꢃ 8 dꢇꢈꢇmbꢇꢅ 2017
aꢈꢈꢇpꢁꢇꢃ 5 Mꢆꢅꢈꢀ 2018
KEYWORDS
Magnoliaceae; ꢉignꢆn;
Schisandra chinensis; nꢆꢁꢊꢅꢆꢉ
pꢅꢄꢃꢊꢈꢁꢂ; ꢈyꢁꢄꢁꢄxiꢈiꢁy
5
0
and 41.0 μM, and cisplatin showed cytotoxic activity with IC50 value
of 27.3 μM.
1
. Introduction
Schisandra chinensis (Turcz.) Baill., a climbing plant mainly distributed in the region of Korea,
Japan, the far east of Russian, and northeastern China (Panossian and Wikman 2008). The
rattan stems of S. chinensis was the dried stems of S. chinensis (Turcz.) Baill., which was listed
officially as a food and herbal medicine, and have been used as a folk medicine for the
treatment of influenza, gastrointestinal dysfunction, frostbite, and asthma in northeastern
China (Shao 1995). Previous investigations indicate that lignans are the common constituents
of the rattan stems of S. chinensis, and some of them possess anti-HIV, anti-HBV, antitumor,
anticholesteremics, antihepatotoxic, antioxidant, anti-inflammation and cytotoxic activity
CONTACT hꢆi-Xꢊꢇ Kꢊꢆng
ꢀxkꢊꢆng@yꢆꢀꢄꢄ.ꢈꢄm, ꢀxkꢊꢆng@ꢀꢄꢁmꢆiꢉ.ꢈꢄm
tꢀꢇ ꢂꢊppꢉꢇmꢇnꢁꢆꢉ ꢃꢆꢁꢆ fꢄꢅ ꢁꢀiꢂ ꢆꢅꢁiꢈꢉꢇ ꢈꢆn bꢇ ꢆꢈꢈꢇꢂꢂꢇꢃ ꢆꢁ ꢀꢁꢁpꢂ://ꢃꢄi.ꢄꢅg/10.1080/14786419.2018.1452000.
©
2018 Infꢄꢅmꢆ uK limiꢁꢇꢃ, ꢁꢅꢆꢃing ꢆꢂ tꢆyꢉꢄꢅ & Fꢅꢆnꢈiꢂ Gꢅꢄꢊp

2
B.ꢀY. YANG ET AL.
(
2
Li et al. 2005; Šmejkal et al. 2010; Li et al. 2015; Xue et al. 2015; Zhu et al. 2015; Xiao et al.
005). As part of our continuous discovering more new natural products, our group have
been isolated some new compounds from the rattan stems of S. chinensis (Yang et al. 2016,
in press). Further investigations led to the isolation of a new lignan named schilignan F (1),
and twelve known ones (2–13). All compounds were evaluated for the cytotoxicities against
Hela cancer cell lines.
2
. Results and discussion
Compound 1 was isolated as an amorphous powder. Its molecular formula was assigned to
+
be C H O by its positive HRESIMS with m/z 537.1973 [M + H] (Calcd for 537.1972). The
2
6
32 12
1
H NMR spectrum showed two 1,2,4-trisubstituted benzene rings at δ 7.10 (1H, d, J = 1.6 Hz),
H
6.72 (1H, d, J = 8.0 Hz), 6.85 (1H, dd, J = 1.6, 8.0 Hz) and 6.95 (1H, d, J = 1.6 Hz), 6.80 (1H, d,
J = 8.0 Hz), 6.79 (1H, dd, J = 1.6, 8.0 Hz). There were also showed the presence of two oxy-
genated methine signals at δ 4.37 (1H, s) and 5.23 (1H, d, J = 6.4 Hz), two sets of oxygenated
H
methylene signals at δ 4.10 (1H, d, J = 10.0 Hz), 4.03 (1H, d, J = 10.0 Hz) and δ 3.91 (1H, m),
H
H
3
.21 (1H, m), two methoxy signals at δ 3.85 (3H, s), 3.86 (3H, s), one methine signal at δH
H
3.56 (1H, m), assigned to a epi-series 7,9′:7′,9-diepoxyligan (Pelter et al. 1976). In addition,
an anomeric proton signal at δ 4.65 (1H, d, J = 7.7 Hz) suggested 1 the existence of a β-glu-
H
1
3
copyranosyl unit. The C NMR and DEPT spectra of 1 showed 26 carbon signals, including,
four oxygenated aromatic carbons (δ 148.4, 147.6, 148.9, 146.7), four oxygenated aliphatic
C
carbons (δ 91.4, 73.1, 83.1, 69.5), two methoxy carbons (δ 56.4, 56.5), and a glucosyl moiety.
C
C
Combination analysis of 1D- and 2D NMR data revealed that 1 had a close resemblance with
-hydroxypinoresinol 8-O-β-d-glucopyranoside 4′-methyl ether (Lee et al. 2011). The obvious
8
differences were resulted from the appearance of a hydroxyl group, and the lack of a methoxy
carbon in 1. This indicated that a methoxy group in 8-hydroxypinoresinol 8-O-β-d-
glucopyranoside 4′-methyl ether was replaced by a hydroxyl group at C-4′ in 1. This was also
supported by the HMBC (Figure S8) correlations of H-2′ (δ 6.95, 1H, d, J = 1.6 Hz) with C-6′
H
(
δ 119.3), C-4′ (δ 146.7). The chemical shift of H-7′ was about δ 5.6, value of the coupling
C
C
H
constant J was about 7 Hz, and carbon signals δ 128.2 (C-1′), 131.0 (C-1), stated that com-
C
pound 1 was the epi-series of furofuranoid lignans (Pelter et al. 1976; CHIBA et al. 1977;
El-Domiaty et al. 2002; Kim et al. 2007), in which H-8′ were in cis relationship to one benzylic
proton (H-7′), while the other benzylic proton (H-7) was trans. The bridge carbons C-8 and
C-8′ have the absolute configuration R (Greger and Hofer 1980), so the absolute configura-
tions of the C-7 and C-7′ for compound 1 were assigned R and R. Furthermore, the sugar was
identified as D-absolute configuration by GC-MS analysis after acid hydrolysis. Thus, 1 was
elucidated as (7R,7′R,8R,8′R)-8-hydroxypinoresinol 8-O-β- -glucopyranoside , and named as
d
schilignan F (Figure 1).
Nine known lignans and three known phenylpropanoids (Figure 1) were identified
as isomassonianoside B (2) (He et al. 2011), (7S,8R)-urolignoside (3) (Kuang et al. 2009), icaris-
ide E4 (4) (Nakanishi et al. 2004), 3-O-β-d-Glucopyranosyloxymethyl-2-(4-hydroxy-3-
methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-dihydrobenzofuran (5) (Kim et al. 2008),
(7S,8R)-dihydrodehydrodiconiferyl alcohol-9-O-β-d-glu copyranside (6) (Kuang et al. 2009),
(+)-1-hydroxypinoresinol-1-O-β-d-glucoside (7) (Zu et al. 2014), (+)-8-hydroxy pinoresinol
(8) (Liu et al. 2012), 7R,8R-threo-4,7,9-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-9′-O-β-
d-glucopyranoside(9) (Matsuda and Kikuchi 1996), (8R,8′S)-marphenol K (10) (Lin et al. 2015;

NATURAL PRODUCT RESEARCH
3
Tran et al. 2016), Eugenol 1-O-β-d-apiofuranosyl(l″-6′)-O-β-d-glucopyranoside (11) (Takeda
et al. 1998), Eugenol 1-O-β-d-glucopyranoside (12) (Zheng et al. 2011), ω-hydroxypropio
guaiacone (13) (Yang et al. 2009), were identified by comparison with literature data (Table
S1) and high-resolution mass spectra of compounds.
The cytotoxic activities of the isolated compounds (1–13) were evaluated against Hela
human cell lines in vitro using a MTT assay. As shown in Table S2, the results suggested that
compounds 2, 6 and 8 exhibited weak cytotoxic activities with IC values of 30.6, 86.3 and
5
0
4
1.0 μM, and cisplatin showed cytotoxic activity with IC value of 27.3 μM.
50
3
. Experimental
3
.1. General experimental procedures
NMR spectra were obtained on a Bruker DPX-400 spectrometer using TMS as an internal
standard, and chemical shifts δ were expressed in ppm. Optical rotations were recorded in
MeOH on a JʌSCO P-2000 polarimeter, whereas UV spectra data were recorded on a Shimadzu
™
UV-1601 spectrophotometer. HRESIMS was performed on a Xevo-TOF-MS spectrometer
(
Waters). Preparative HPLC (LC-6AD, Shimadzu) was carried out on a C column (10 × 250 mm,
18
5
μm, Waters) with a RID-10A detector, the flow rates were 3 mL/min. Column chromatog-
raphy was performed with Silica gel (80–100 mesh; 200–300 mesh, China), ODS (50 μm, YMC,
Japan). TLC was carried out on silica gel F254 plates (Merck, Germany). All solvents were
analytical reagent.
3
.2. Plant material
The rattan stems of S. chinensis were collected from Raohe, Heilongjiang province, P. R. China,
in August 2010. The voucher specimen (Herbarium NO. 20100899) is deposited at the School
of Pharmacy, Heilongjiang University of Chinese Medicine, P. R. China, and identified by Prof.
Ruifeng Fan of Heilongjiang University of Chinese Medicine.
Figure 1. tꢀꢇ ꢂꢁꢅꢊꢈꢁꢊꢅꢇ ꢄf ꢈꢄmpꢄꢊnꢃꢂ 1–13.

4
B.ꢀY. YANG ET AL.
3
.3. Extraction and isolation
The air-dried rattan stems of S. chinensis (13.5 kg) were extracted with 70% ethanol three
times, under reflux for 2 h each time. After solvent removal, the crude extract (1.82 kg) was
suspended in H O (26 L) and further extracted with petroleum ether (PE), EtOAc and BuOH,
2
successively, to obtain corresponding extracts after removal of the solvent. The n-butyl layer
(
110.6 g) was chromatographed on a silica gel column (200–300 mesh, 1 kg) using solvent
system CH Cl /MeOH (10:1 to 0:1) to give seven fractions (I-VII) based on TLC analysis. Fr. III
2
2
was subjected to silica gel chromatography, using solvent system CHCl /MeOH (200:1 to
2
0:1), to provide Fr. III-1 to III-11. Fr. III-3 was purified by preparative HPLC, to yield 2 (15 mg)
and 1 (5 mg). Fr. III-5 was purified by ODS chromatography to yield 3 (17 mg) and 7 (18 mg).
Fr. III-7 was purified by ODS chromatography to yield 12 (16 mg) and 11 (20 mg). Fr. IV was
subjected to ODS chromatography, to provide Fr. IV-1 to IV-10. Fr. IV-5 was purified by pre-
parative HPLC to yield 4 (23 mg). Fr. IV-6 was purified by preparative HPLC to yield 8 (9 mg)
and 5 (11 mg). Fr. VI was subjected to silica gel chromatography, using solvent system CHCl2/
MeOH (200:1 to 0:1), to provide Fr. VI-1 to VI-12. Fr. VI-7 was purified by preparative HPLC, to
yield 9 (22 mg), Fr. VI-8 was purified by preparative HPLC, to yield 6 (16 mg). Fr. VII was further
subjected to CC (Silica gel CHCl /MeOH 200:1 to 0:1) to resolve into compounds 13 (15 mg)
2
and 10 (19 mg).
2
2
Schilignan F (1): white amorphous powder.[ꢀ] + 11 (c 0.1, MeOH). UV (MeOH) λ 233,
D
max
+
+
1
2
84 nm. HRESIMS m/z 537.1973 [M + H] (Calcd for C H O , 537.1972). H NMR (400 MHz,
26
33 12
MeOH): δ 7.10 (1H, d, J = 1.6 Hz, H-2), 6.72 (1H, d, J = 8.0 Hz, H-5), 6.85 (1H, dd, J = 1.6, 8.0 Hz,
H
H-6), 4.37 (1H, s, H-7), 4.10 (1H, d, J = 10.0 Hz, H-9a), 4.03 (1H, d, J = 10.0 Hz, H-9b), 6.95 (1H,
d, J = 1.6 Hz, H-2′), 6.80 (1H, d, J = 8.0 Hz, H-5′), 6.79 (1H, dd, J = 1.6, 8.0 Hz, H-6′), 5.23 (1H, d,
J = 6.4 Hz, H-7′), 3.56 (1H, m, H-8′), 3.91 (1H, m, H-9′a), 3.21 (1H, m, H-9b), 4.65 (1H, d, J = 7.7 Hz,
H-1″), 3.09 (1H, m, H-2″), 3.38 (1H, m, H-3″), 3.26 (1H, m, H-4″), 3.29 (1H, m, H-5″), 3.80 (1H,
dd, J = 2.0, 12.0 Hz, H-6″a), 3.57 (1H, dd, J = 5.8, 12.0 Hz, H-6″b), 3.85 (3H, s, -OCH ), 3.86 (3H,
3
13
s, -OCH ). C NMR (100 MHz, MeOH): δ 128.4 (C-1), 113.9 (C-2), 148.4 (C-3), 147.6 (C-4), 115.2
3
C
(
(
(
C-5), 122.4 (C-6), 91.4 (C-7), 97.3 (C-8), 73.1 (C-9), 131.0 (C-1′), 110.4 (C-2′), 148.9 (C-3′), 146.7
C-4′), 116.1 (C-5′), 119.3 (C-6′), 83.1 (C-7′), 54.4 (C-8′), 69.5 (C-9′), 100.1 (C-1″), 75.2 (C-2″), 78.2
C-3″), 71.4 (C-4″), 77.9 (C-5″), 62.6 (C-6″), 56.4 (3-OCH ), 56.5 (3′-OCH ).
3
3
3
.4. Acid hydrolysis of new compound (1) and GC analysis
A solution of schilignan F (1, 2.0 mg) were treated with 2 mL H O and 1 mL 2 N aqueous HCl
2
at 80 °C for 4 h. After cooling, H O (5 mL) was added and neutralized with 2 N KOH. Then,
2
the reaction mixtures were extracted with EtOAc (3 mL × 3). The aqueous layer removed
under reduced pressure, and dissolved in anhydrous pyridine (5 mL) and treated with
L-cysteine methyl ester hydrochloride (1.5 mg). The mixture was stirred at 60 °C for 1 h, then
150 μL of HMDS-TMCS (hexamethyldisi lazane-trimethylchlorosilane, 3:1) was added, then
stirred for another 30 min at 60 °C. After centrifuged off, the supernatant was concentrated
under N stream. The residue was partitioned between CHCl and H O, and the CHCl layer
2
3
2
3
(
1 μL) was analyzed by GC-MS (Wu et al. 2012; Tabopda et al. 2016; Yang et al. 2017), respec-
tively. The absolute configurations of D-glucose for compound 1 was determined by the
same retentions times (R ) of standard D-glucose (R at 16.3 min).
t
t

NATURAL PRODUCT RESEARCH
5
3
.5. Cytotoxic activity
Cytotoxicities of compounds 1–13 were evaluated for against Hela cancer cell lines obtained
from China Center for Type Culture Collection by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphe-
nyl-2-tetrazoliumbromide (MTT) assay reported previously (Mosmann 1983), cisplatin
(Sigma) was used as positive control. Cells were cultured in medium (10% fetal bovine serum/
DMEM/penicillin -streptomycin = 5:45:0.5) at 37 °C in humidified 5% CO . 100 μL of adherent
2
4
cells were plated in 96-well tissue plates at optimal cell density (10 cells per well). Adherent
cell lines were previously incubated for 24 h to ensure attachment and growth. Compounds
1
–13 were applied at various concentrations (1, 5, 10, 25, 50, 100 μM) with a volume of 100
μL in triplicate. After 24 h of cultivation, 10 μL of MTT (0.5 mg/mL) were added to each well
and further incubated for 4 h at 37 °C, and were lysate with DMSO (100 μL/well). Its absorb-
ance of the lysate was measured at 490 nm (BioTek). The half-maximal inhibitory concentra-
tion values (IC ) was calculated using the Probit program in SPSS 17 for windows 7 (SPSS
5
0
Inc.Chicago).
4
. Conclusion
A new lignan, schilignan F (1), along with nine known lignans (2–10) and three known
phenylpropanoids (11–13), were isolated from the rattan stems of S. chinensis. Compounds
1
–9, 11–13 were obtained from Magnoliaceae for the first time, compound 10 was firstly
isolated from the plant. This study indicated that lignans and phenylpropanoids are also the
main components of the rattan stems of S. chinensis, expect for dibenzocyclooctadiene
lignans. Moreover, we investigated the cytotoxicities against human Hela cancer cell lines
in vitro. As a result, the compounds 2, 6 and 8 exhibited weak cytotoxic activities, which
indicated that the presence of a hydroxyl group might contribute to the cytotoxic activity
against Hela cancer cell lines.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This research was supported by National Natural Science Foundation Project [grant number 81473325]
References
CHIBA M, HISADA S, Thieme H. 1977. The position of glucose linkage in phillyrin. Chem Pharm Bull
(
Tokyo). 25:3435–3436.
El-Domiaty MM, El-Shafae AM, Abdel-Aal MM, Abou-Hashem MM. 2002. The first report on the
occurrence of furofuranoid lignan glucosides in Acanthaceae. Pharm Biol. 40:96–102.
Greger H, Hofer O. 1980. New unsymmetrically substituted tetrahydrofurofuran lignans from Artemisia
absinthium: assignment of the relative stereochemistry by lanthanide induced chemical shifts.
Tetrahedron. 36:3551–3558.
HeWJ, Fu ZH, Han HJ,Yan H, Zeng GZ, Ji CJ, Chu HB, ZhangYM,Tan NH. 2011. Benzoic acid allopyranosides
and lignan glycosides from the twigs of Keteleeria evelyniana. Zeitschrift für Naturforschung B.
66:0733–733739.

6
B.ꢀY. YANG ET AL.
Kim KH, Lee KH, Choi SU, Kim YH, Lee KR. 2008. Terpene and phenolic constituents of Lactuca indica L.
Arch Pharm Res. 31:983–988.
Kim MR, Moon HT, Lee DG, Woo ER. 2007. A new lignan glycoside from the stem bark of styrax japonica
s. et Z. Arch Pharm Res. 30:425–430.
Kuang HX, Xia YG, Yang BY, Wang QH, Lü SW. 2009. Lignan constituents from Chloranthus japonicus
Sieb. Arch Pharm Res. 32:329–334.
Lee DG, Lee SM, Bang MH, Park HJ, Lee TH, Kim YH, Kim JY, Baek NI. 2011. Lignans from the flowers
of Osmanthus fragrans var. aurantiacus and their inhibition effect on NO production. Archives of
Pharmacal Research. 34:2029–2035.
Li RT, Han QB, ZhengYT, Wang RR, Yang LM, LuY, Sang SQ, Zheng QT, Zhao QS, Sun HD. 2005. Structure
and anti-HIV activity of micrandilactones B and C, new nortriterpenoids possessing a unique skeleton
from Schisandra micrantha. Chem Commun. 23:2936–2938.
Lin SY, Ko HH, Lee SJ, Chang HS, Lin CH, Chen IS. 2015. Biological evaluation of secondary metabolites
from the root of Machilus obovatifolia. Chem Biodivers. 12:1057–1067.
Liu CS, Cao FH, Peng XJ, Luo JJ, Zeng C. 2012. Chemical constituents from Gentiana striata. J Chinese
Med Mater. 35:908–910.
Li W, Liu Y, Wang Z, Yu T, Lu Q, Chen H. 2015. Suppression of MAPK and NF-κB pathways by schisandrin
B contributes to attenuation of DSS-induced mice model of inflammatory bowel disease. Pharmazie.
70:598–603.
Matsuda N, Kikuchi M. 1996. Studies on the Constituents of Lonicera Species. X. Neolignan Glycosides
from the Leaves of Lonicera gracilipes var. glandulosa MAXIM. Chem Pharm Bull. 44:1676–1679.
Mosmann T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation
and cytotoxicity assays. J Immunol Methods. 65:55–63.
NakanishiT, Iida N, InatomiY, Murata H, Inada A, Murata J, Lang FA, Linuma M, TanakaT. 2004. Neolignan
and flavonoid glycosides in Juniperus communis var. depressa. Phytochemistry. 65:207–213.
Panossian A, Wikman G. 2008. Pharmacology of Schisandra chinensis Bail.: An overview of Russian
research and uses in medicine. J Ethnopharmacol. 118:183–212.
Pelter A, Ward RS, Rao EV, Sastry kV. 1976. General methods for the assignment of stereochemistry to
2,6-diaryl-3,7-dioxabicyclo [3.3.0] octane lignans. Tetrahedron. 32:2783–2788.
Shao ZX. 1995. Edible and medicinal value and utilization of schisandrae Chin. Wild Plant Resour. 4:33.
Šmejkal K, Šlapetová T, Krmenčík P, Babula P, Dall'Acqua S, Innocenti G, Vančo J, Casarin E, Carrara M,
Kalvarová K, et al. 2010. Evaluation of cytotoxic activity of Schisandra chinensis lignans. Planta Med.
7
6:1672–1677.
Tabopda TK, Mitaine-Offer AC, Paululat T, Delemasure S, Dutartre P, Ngadjui BT, Lacaille-Dubois MA.
016. Steroidal saponins from Chlorophytum deistelianum. Phytochemistry. 126:34–40.
2
TakedaY, OoisoY, MasudaT, Honda G, Otsuka H, Sezik E, Yesilada E. 1998. Iridoid and eugenol glycosides
from Nepeta cadmea. Phytochemistry. 49:787–791.
Tran TD, Pham NB, Booth R, Forster PI, Quinn RJ. 2016. Lignans from the Australian endemic plant
Austrobaileya scandens. J Nat Prod. 79:1514–1523.
Wu SB, Meyer RS, Whitaker BD, Litt A, Kennelly EJ. 2012. Antioxidant glucosylated caffeoylquinic acid
derivatives in the invasive tropica soda apple. Solanum viarum J Nat Prod. 75:2246–2250.
Xiao WL, Li RT, Li SH, Li XL, Sun HD, ZhengYT, Wang RR, LuY, Wang C, Zheng QT. 2005. Lancifodilactone
F: a novel nortriterpenoid possessing a unique skeleton from Schisandra lancifolia and its anti-HIV
activity. Org Lett. 7:1263–1266.
Xue Y, Li X, Du X, Li X, Wang W, Yang J, Chen J, Pu J, Sun H. 2015. Isolation and anti-hepatitis B virus
activity of dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis. Phytochemistry.
116:253–261.
Yang BY, Guo JT, Li ZY, Wang CF, Wang ZB, Wang QH, Kuang HX. 2016. New thymoquinol glycosides
and neuroprotective dibenzocyclooctane lignans from the rattan stems of Schisandra chinensis.
Chem Biodivers. 13:1118–1125.
Yang BY, Liu Y, Jiang HB, Xu ZP, Guo R, Wang R, Li XM, Kuang HX. 2017. Phenylpropanoids from the
fruits of Nicandra physaloides and their anti-inflammatory activities. Nat Prod Res. 31:2634–2640.
Yang JQ, He WJ, Tan NH, Chu HB, Zhang YM, Mei WL, Dai HF. 2009. Chemical constituents of Pedicularis
cephalantha Franch and P. siphonantha Don. Nat Prod Res Dev. 21:600–603.

NATURAL PRODUCT RESEARCH
7
Yang BY, Guo JT, Wang ZB, Li ZY, Zheng GX, Wang QH, Kuang HX. in press. Monoterpenoid glycosides
from the rattan stems of Schisandra chinensis.
Zheng MS, Li G, Li Y, Seo CS, Lee YK, Jung JS, Song DK, Bae HB, Kwak AH, Chang HW, Kim JR. 2011.
Protective constituents against sepsis in mice from the root barks of Ulmus davidiana var. japonica.
Arch Pharm Res. 34:1443–1450.
Zhu L, Li B, Liu X, Huang G, Meng X. 2015. Purification of six lignans from the stems of Schisandra
chinensis by using high-speed counter-current chromatography combined with preparative high-
performance liquid chromatography. Food Chem. 186:146–152.
Zu XP, Zhang WD, Han ZZ, Li HL. 2014. Water soluble chemical constituents of Valeriana officinalis Linn.
var. latiofolia Miq. Acad J Second Mil Med Univ. 35:161–170.