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1Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic
Affairs Commission & Ministry of Education, School of Ethnic Medicine,
Yunnan Minzu University, Kunming, China
Corresponding Authors:
Guangzhi Zeng and Junlin Yin, Key Laboratory of Chemistry in Ethnic
Medicinal Resources, State Ethnic Affairs Commission & Ministry of
Education, School of Ethnic Medicine, Yunnan Minzu University, Kunming,
China.
Emails: g. zh_ zeng@ 163. com; yinjunlin@ mail. kib. ac. cn
Original Article
Natural Product Communications
Volume 16(2): 1–6
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Two New Sesquiterpenoids Isolated
From Cyperus rotundusL
QiangWang1, ChundieYi1, WenlanDuan1, YunfengDuan1,
JiahaoLou1, GuangzhiZeng1, and JunlinYin1
Abstract
Two new sesquiterpenoids, isocyperotundone (1) and 1,4- epoxy-4- hydroxy-4,5- seco- guain-11- en-5- one (2), together with 6 known
sesquiterpenoids, cyperotundone (3), cyperenoic acid (4), sugetriol triacetate (5), cyperusol A3 (6), cyperusol A2 (7), and cyperusol
A1 (8), were isolated from the methanol extract of the rhizomes of Cyperus rotundus L. High- resolution electrospray ionization mass
spectrometry and 1- dimensional (1D) and 2D nuclear magnetic resonance spectroscopy were used to establish the structures of all
the compounds. All the compounds were tested for activity on nuclear factor kappa- light- chain- enhancer of activated B cells (NF-
κB) signaling. Compounds 1-7 exhibited inhibitory activity on tumor necrosis factor-α- induced activation of the NF-κB pathway,
with half- maximal inhibitory concentration values ranging from 34.5 to 73.7 μmol/L.
Keywords
Cyperus rotundus L., terpenoids, sesquiterpenoids, bioactivity, NF-κB pathway
Received: August 12th, 2020; Accepted: December 18th, 2020.
Cyperus rotundus L. (Nutgrass, family Cyperaceae) is broadly dis-
seminated in many tropical, subtropical, and temperate regions
of the world.1 The dried rhizomes of C. rotundus have been
used in traditional medicine to treat various diseases such as
spasms, stomach disorders, inflammatory diseases, and wom-
en’s diseases in some Asian countries.2-6 Phytochemical studies
of the species have resulted in the isolation of monoterpenoids,
sesquiterpenoids, flavonoids, triterpenoids, and sterols.7-11 The
plant also possesses a vast array of biological activities, includ-
ing antipyretic, analgesic, anti- inflammatory, antibacterial, anti-
oxidant, neuroprotective, anticancer, antidiarrheal, and
antidysmenorrhea.12-17 Sesquiterpenoids are the main constitu-
ents of this herb with diverse skeletons such as eudesmane,
guaiane, patchoulane, cadinane, copane, and rotundane
types.18-20 As part of our continuing search for new bioactive
compounds from medicinal plants, we isolated 2 new sesquit-
erpenoids, isocyperotundone (1) and 1,4- epoxy-4- hydroxy-4,5-
seco- guain-11- en-5- one (2), together with 6 known sesquiter-
penoids, cyperotundone (3),21 cyperenoic acid (4),22 sugetriol
triacetate (5),23 cyperusol A3 (6),24 cyperusol A2 (7),25 and cype-
rusol A1 (8)25 from the rhizomes of C. rotundus. The structures
and molecular formulas of these compounds are shown in
Figure1. The 1H nuclear magnetic resonance (NMR) and 13C
NMR spectroscopic data (deuterated chloroform [CDCl3]) for
compounds 3-8 are shown in Supplemental Tables S1- S2.
Herein, we report the isolation, purification, and structure elu-
cidation, as well as the inhibitory activity of these compounds
against nuclear factor kappa- light- chain- enhancer of activated
B cells (NF-κB) signaling.
Compound 1 was isolated as a colorless oil. Its molecular
formula of C15H22O was determined by high- resolution elec-
trospray ionization mass spectrometry (HR- ESI- MS) from the
pseudomolecular ion peak at m/z 219.1743 [M + H]+ (calcd for
C15H22OH, 219.1748), with 6 degrees of unsaturation
(Supplemental Figure S1). The 1H- NMR spectrum
(Supplemental Figure S2; Table1) of 1 showed 4 typical methyl
groups at δH 1.85 (3H, s, H3-14), δH 1.27 (3H, s, H3-12), δH 0.96
(3H, s, H3-13), and δH 0.73 (3H, d, J = 6.6 Hz, H3-15); 6 meth-
ylene protons at δH 2.82 (1H, m, Ha-6), δH 2.67 (1H, dd, 5.7,
11.5 Hz, Hb-6), δH 2.16 (2H, m, H2-2), δH 1.81 (1H, m, Ha-3),
and δH 1.49 (1H, m, Hb-3); and 1 olefin proton at δH 6.18 (1H,
s, H-9). The 13C- NMR spectrum (Supplemental Figure S3;
Table 1), which combines distortionless enhancement by
Natural Product Communications
2
polarization transfer (DEPT) (Supplemental Figure S4) and
heteronuclear single quantum correlation (HSQC) data
(Supplemental Figure S5) for 1, presented 15 carbons including
4 methyl groups (δC 27.9, 25.8, 19.1, 14.7), 3 methylene groups
(δC 45.0, 30.9, 27.6), 4 methine groups (δC 128.1, 54.0, 46.8,
31.6), and 4 quaternary carbons (δC 209.4, 141.8, 68.6, 38.8).
The above data suggested that 1 was a patchoulane- type
sesquiterpenoid similar to cyperotundone21,24 (3). The main
difference between 1 and 3 was that the position of the α,β-
unsaturated carbonyl group in 1 changed from C-3/C-4/C-5 to
C-8/C-9/C-10. The heteronuclear multiple bond correlation
(HMBC) spectrum (Supplemental Figure S6; Table1) correla-
tions between H3-14 (δH 1.85) and C-10 (δC 141.8), C-9 (δC
128.1) and C-1 (δC 68.6) indicated that the methyl group (Me-
14) was attached to C-10, and the correlations from H-9 (δH
6.18) to C-8 (δC 209.4) and C-14 (δC 19.1) with the correlations
from H-7 (δH 2.18) to C-8 (δC 209.4) and C-6 (δC 45.0) sug-
gested that the location of the α,β- unsaturated ketone structure
was at C-8/C-9/C-10. Other HMBC between H-5 (δH 3.44) to
C-1 (δC 68.6) and C-10 (δC 141.8), between H3-13 (δH 0.96) and
C-11 (δC 38.8), C-7 (δC 46.8) and C-1 (δC 68.6), between H3-12
(δH 1.27) and C-11 (δC 38.8), C-7 (δC 46.8) and C-1 (δC 68.6),
with the correlations from H-7 (δH 2.18) to C-1 (δC 68.6), C-12
(δC 27.9) and C-13 (δC 25.8) indicated the connection of C-1/
C-5/C-7/C-11 and proved the existence of a 5- membered
ring. Other fragments of 1 were determined from the 1H-1H
Correlation Spectroscopy (COSY) spectra (Supplemental
Figure S7) correlations of H-2 (δH 2.16)/Ha-3 (δH 1.81), H3-15
(δH 0.73)/H-4 (δH 2.50)/Hb-3 (δH 1.49), and Hb-6 (δH 2.67)/
H-7 (δH 2.18). The relative configuration of 1 was elucidated by
rotating frame Overhauser effect spectroscopy (ROESY)
(Supplemental Figure S8). The key correlation from H-5 (δH
3.44) to H3-15 (δH 0.73) suggested that H-5 and Me-15 were
coplanar and assigned a β- orientation. Correlations from H-4
(δH 2.50) to H3-12 (δH 1.27) indicated that H-4 and C-11 were
on the same side and defined as α- orientation. Thus, the struc-
ture of 1 was determined to be isocyperotundone (Figure2).
Figure 1. Structures of the compounds isolated from Cyperus rotundus.
Table 1. Nuclear Magnetic Resonance Spectroscopic Data
(Deuterated Chloroform, 600 and 150 MHz), and Key HMBCs of
Compound 1.
No. δH(J in Hz) δCHMBC
1 - 68.6
2 2.16 (2H, m) 27.6 C-1, C-3, C-4
3 1.81 (1H, m)
1.49 (1H, m)
30.9 C-1, C-2,
C-4, C-15
4 2.50 (1H, m) 31.6 C-1, C-3, C-5, C-15
5 3.44 (1H, m) 54.0 C-1, C-10
6 2.82 (1H, m)
2.67 (1H, dd, 5.7, 11.5)
45.0 C-7, C-8, C-11
7 2.18 (1H, m) 46.8 C-6, C-13, C-8, C-1
8 - 209.4
9 6.18 (1H, s) 128.1 C-1, C-8, C-14
10 - 141.8
11 - 38.8
12 1.27 (3H, s) 27.9 C-7, C-11, C-12, C-1
13 0.96 (3H, s) 25.8 C-7, C-11, C-1
14 1.85 (3H, s) 19.1 C-9, C-10
15 0.73 (3H, d, 6.6) 14.7 C-3, C-4
Abbreviation: HMBC, heteronuclear multiple bond correlation.
Wang etal. 3
Compound 2 was obtained as a colorless oil. Its molecular
formula was assigned as C15H24O3 by HR- ESI- MS from the
pseudo- molecular ion peak at m/z 275.1618 [M + Na]+ (calcd
for C15H24O3Na, 275.1620), with 4 degrees of unsaturation
(Supplemental Figure S10). The infrared (IR) spectrum
(Supplemental Figure S21) revealed the presence of a hydroxy
group (3429 cm−1), and due to its strong, wide, and scattered
characteristics, there may be intramolecular hydrogen bonds.
The 1H- NMR spectrum (Supplemental Figure S11; Table2) of
2 showed 3 methyl groups at δH 1.76 (3H, s, H3-13), δH 1.31
(3H, s, H3-15), and δH 0.90 (3H, d, J = 7.1 HZ, H3-14); 6 groups
of methylene protons at δH 3.50 (1H, m, H- 6a), δH 2.21 (1H, m,
H- 6b), δH 1.98 (1H, m, H- 9a), δH 1.17 (1H, m, H- 9b), δH 2.26
(2H, m, H2-2), δH 1.74 (2H, m, H2-3), and δH 1.71 (2H, m,
H2-8) and 1 olefinic CH2 group at δH 4.74 (2H, m, H2-12). The
13C- NMR spectrum (Supplemental Figure S14; Table 2) in
combination with the DEPT experiment (Supplemental Figure
S15) allowed the identification of 15 carbons including 3
methyl groups (δC 25.7, 20.3, 15.3), 6 methylene groups (δC
109.7, 41.8, 31.0, 30.3, 28.6, 23.0), 2 methine groups (δC 44.5,
37.2), and 4 quaternary carbons (δC 211.9, 149.0, 99.2, 91.1).
The NMR spectroscopic data for 2 were quite similar to those
of 4,5- seco- guaiane,26 which was isolated from Pellia epiphylla,
except that the isopropenyl group attached to C-7 replaces the
isopropyl group. The HMBCs (Supplemental Figure S17;
Table2) from 2 olefin protons H2-12 (δH 4.74) and a unimodal
methyl group H3-13 (δH 1.76) to a tertiary carbon C-11 (δC
149.0) indicated the presence of an isopropenyl group. This
group, which is positioned at C-7, was determined by HMBCs
of H2-12 (δH 4.74) and H3-13 (δH 1.76) with C-7 (δC 44.5).
Other fragments of 2 were determined from the 1H-1H
COSY spectrum (Supplemental Figure S18) correlations of
H-2 (δH 2.26)/H-3 (δH 1.74) and H-6 (δH 3.50)/H-7 (δH 2.32)/
H-8 (δH 1.71)/H-9 (δH 1.98). The stereochemical structure of
2 was derived from the ROESY spectrum (Supplemental
Figure S19). C-4 of compound 2 was a hemiacetal, indicating
the existence of an equilibrium mixture. When the hydroxy
group at C-4 has a β- orientation, it could form a stable intra-
molecular hydrogen bond linked to the ketone at C-526, there-
fore it was determined as the dominant configuration. In the
ROESY spectrum, major cross- peaks from H3-14 (δH 0.90) to
H3-15 (δH 1.31) were observed, and the H atoms distance of
H3-14 and H3-15 was 2.7 × 10-10 m (Figure3), indicating that
Me-14 and Me-15 were on the same side and thus had an α-
orientation. The stereochemical structure of C-1 was derived
from the ROESY spectrum. Correlations existed between
H-10 (δH 1.79) and the 2 methylene protons (δH 2.26) of C-2
indicated that H-10 and C-2 were on the same side and thus
had a β- orientation. Correlations from H-7 (δH 2.32) to H-10
(δH 1.79) suggested that H-7 and H-10 were on the same side
and assigned as β- orientation. In summary, the structure of 2
was determined as 1,4- epoxy-4- hydroxy-4,5- seco- guain-11- en-
5- one (Figure3).
Figure 2. Key heteronuclear multiple bond correlation (H→C), 1H-1H correlation spectroscopy (H H), and rotating frame Overhauser
effect spectroscopy (H H) correlations of compound 1.
Table 2. Nuclear Magnetic Resonance Spectroscopic Data
(Deuterated Chloroform, 600 and 150 MHz), and Key HMBCs of
Compound 2.
No. δH(J in Hz) δCHMBC
1 - 91.1
2 2.26 (2H, m) 23.0 C-1, C-4, C-5
3 1.74 (2H, m) 30.3
4 - 99.2
5 - 211.9
6 3.50 (1H, m)
2.21 (1H, m)
41.8 C-5, C-7, C-8,
C-11
7 2.32 (1H, m) 44.5 C-6, C-11, C-13
8 1.71 (2H, m) 28.6 C-6, C-7, C-9
9 1.98 (1H, m)
1.17 (1H, m)
31.0 C-7, C-10
10 1.79 (1H, m) 37.2 C-5
11 - 149.0
12 4.74 (2H, m) 109.7 C-7, C-11, C-13
13 1.76 (3H, s) 20.3 C-7, C-11, C-12
14 0.90 (3H, d, 7.1) 15.3 C-1, C-9, C-10
15
-OH
1.31 (3H, s)
3.18 (1H, s)
25.7
-
C-3, C-4
C-4, C-15
Abbreviation: HMBC, heteronuclear multiple bond correlation.
Natural Product Communications
4
The NF-κB transcription factor plays a significant role in
regulating various aspects of immune functions, and its abnor-
mal activation is involved in the pathogenesis of diverse auto-
immune and inflammatory diseases.27 The effects of
compounds 1-8 on the NF-κB signaling pathway were investi-
gated by the dual- luciferase reporter assay. The results showed
that compounds 1-7 can inhibit tumor necrosis factor- alpha
(TNF-α)- induced NF-κB activation; half- maximal inhibitory
concentration (IC50) values are shown in Table3.
Conclusion
In summary, 8 sesquiterpenoids were isolated and character-
ized from C. rotundus L, including 2 new ones (1 and 2) and 6
known ones (3-8). Compounds 1-7 showed inhibitory effects
on the NF-κB signaling pathway, with IC50 values ranging from
34.5 to 73.7 μmol·L-1. Sesquiterpenoids are the main constitu-
ents of C. rotundus, and they also showed potential biological
activities for this herb.13,17 As one part of our research on anti-
inflammatory components from C. rotundus, the study of the
new anti- inflammatory sesquiterpenoids provided an effica-
cious material basis for our follow- up research on biological
sesquiterpenoids.
Experimental
Plant Material
The rhizomes of C. rotundus L. were purchased from Shengru
Biological Technology Co. Ltd. (batch number: 121059‐200706),
Yunnan province, China, in January 2018, and authenticated by
Associate Professor Xiaoli Liu of Yunnan University of
Chinese Medicine.
General Procedures
One and 2- dimensional NMR experiments were recorded on a
Bruker DRX-600 spectrometer operating at 600 MHz (1H) and
150 MHz (13C) at 300 K (chemical shifts δ in ppm, coupling
constants J in Hz) (Bruker, Germany). HR- ESI- MS data were
obtained on a Waters AutoSpec Premier P776 mass spectrom-
eter (Waters Co., Milford, MA, USA). High- performance liquid
chromatography (HPLC) separation was performed on an
Agilent 1260 series with Agilent ZORBAX SB (9.4 × 250 mm)
(Agilent Technologies, CA, USA) and YMC- Pack Pro (10 ×
250 mm) analytical columns packed with C18 (5 µm) (YMC Co.
Ltd., Kyoto, Japan). IR spectra were obtained on a JASCO FT/
IR-4600 plus Fourier transform infrared spectrometer using
potassium bromide pellets. Column chromatography (CC) was
performed on Sephadex LH-20 (GE Healthcare, USA) and sil-
ica gel (100, 200, 200‐300, or 300‐400 mesh) (Qingdao Marine
Chemical Inc., Qingdao, China). All solvents used for chro-
matographic separations were distilled before use. Double
luciferase reporter gene detection kits (Promega, United
States), Lipofectamine 2000 (Thermo Fisher, USA), Dulbecco’s
modified Eagle’s medium, fetal bovine serum, glutamine
(Biological Industries, Israel), and dexamethasone (Aladdin,
China) were used for the bioassay of compounds.
Extraction and Isolation
Powdered and air- dried rhizomes of C. rotundus (20 kg) were
extracted 5 times with 95% methanol (MeOH) by maceration
for 24 hours at room temperature. The MeOH extracts (2 kg)
were combined and concentrating under reduced pressure. A
portion of this extract was suspended in water (H2O) and
Figure 3. key HMBC (H→C) and 1H-1H COSY (H H) and ROESY (H H) correlations of compound 2.
Table 3. NF-κB Inhibitory Effects of Compounds 1-7 of Cyperus
rotundus.
Compound IC50 (μM)
1 34.5 ± 2.9
2 69.9 ± 5.3
3 69.5 ± 2.9
4 69.5 ± 0.8
5 72.6 ± 3.0
6 67.9 ± 2.9
7
Dexa73.7 ± 6.8
12.2 ± 2.1
Abbreviations: IC50, half- maximal inhibitory concentration ; NF-κB, nuclear
factor kappa- light- chain- enhancer of activated B cells.
aDexamethasone (Dex) was used as a positive control.
Wang etal. 5
successively extracted with light petroleum (PE), ethyl acetate
(EtOAc), and n- butanol (n- BuOH) to give PE (412 g), EtOAc
(200 g), and n- BuOH (98.3 g) fractions, respectively. The PE
extract (412 g) was fractionated by CC (2500 g) on silica gel
(100, 200 mesh, 15 × 100 cm) eluting with PE/EtOAc (100:0
to 0:100, v/v) to afford 8 fractions (A- H).
Fr. C (27.2 g) was separated using a Sephadex LH-20 col-
umn (MeOH) to yield 5 fractions (C-1- C-5). Fr. C-2 (4.9 g) was
further separated using silica gel CC (200-300 mesh) and then
depurated by iterative semi- preparative HPLC to obtain com-
pound 4 (31.7 mg, CH3CN- H2O 80:20, ν = 1.0 mL/min, tR =
25.3 minutes). Fr. C-4 (6.7 g) was subjected to silica gel CC
(200, 300 mesh) eluting with PE/EtOAc (50:1 to 5:1, v/v) to
yield compound 5 (502.4 mg) after recrystallization, and then
purification using a Sephadex LH-20 column (MeOH) afforded
compound 3 (11.2 mg) and 6 (6.7 mg).
Fr. D (67.3 g) was separated and subjected to reiterative sil-
ica gel CC (200-300, 300‐400 mesh) to give compounds 2 (4.5
mg), 7 (3.9 mg), and 8 (3.2 mg). Fr. E (70.3 g) was separated by
silica gel CC with PE/EtOAc (50:1 to 1:1, v/v) to give 5 frac-
tions (E-1- E-5). Fr. E-3 (22.2 g) was further separated by
repeated semi- preparative HPLC eluted with CH3CN- H2O
(v/v, 75:25, ν = 1.5 mL/min) to give compound 1 (2.8 mg, tR =
30.4 minutes).
Isocyperotundone (1): colorless oil; HR- ESI- MS m/z
219.1743 [M + H]+ (calcd for C15H22OH, 219.1748);
[
α
]20
D
:
+20.8 (chloroform [CHCl3], c 0.02); 1H- NMR and 13C- NMR
data (CDCl3, 600 and 150 MHz): (Table1).
1,4- Epoxy-4- hydroxy-4,5- seco- guain-11- en-5- one (2): col-
orless oil; HR- ESI- MS m/z 275.1618 [M + Na]+ (calcd for
C15H24O3Na, 275.1620);
[
α
]20
D
: −80.5 (CHCl3, c 0.06); 1H-
NMR and 13C- NMR data (CDCl3, 600 and 150 MHz): (Table2).
NF-κB Luciferase Assay
The inhibitory activity of the compounds on TNF-α- induced
NF-κB activation was tested with the dual- luciferase assay, as
described in our previous publication.28
Declaration of Conflicting Interests
The author(s) declared no potential conflicts of interest with respect
to the research, authorship, and/or publication of this article.
Funding
The author(s) disclosed receipt of the following financial support for
the research, authorship, and/or publication of this article: This work
was supported by National Natural Science Foundation of China (
31760095, 81960639, 21768005), Yunnan province key laboratory
construction plan funding of universities, and Yunnan province
engineering research center construction plan funding of universities.
ORCID ID
Junlin Yin https:// orcid. org/ 0000- 0001- 8508- 5629
Supplemental Material
Supplemental material for this article is available online.
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