Aromatic glycosides from the whole plants of Iris japonica

Article abstract of DOI:10.1080/10286020.2016.1188807

Phytochemical investigation on the whole plants of Iris japonica led to the isolation of four new aromatic glycosides. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as (?)-4-hydroxy-3-methoxy

Full text of DOI:10.1080/10286020.2016.1188807

Journal of Asian Natural Products Research
ISSN: 1028-6020 (Print) 1477-2213 (Online) Journal homepage: http://www.tandfonline.com/loi/ganp20
Aromatic glycosides from the whole plants of Iris
japonica
Guo-Ru Shi, Xin Wang, Yan-Fei Liu, Chun-Lei Zhang, Yan Wang, Li Li, Gang Ni,
Ruo-Yun Chen & De-Quan Yu
To cite this article: Guo-Ru Shi, Xin Wang, Yan-Fei Liu, Chun-Lei Zhang, Yan Wang, Li Li, Gang Ni,
Ruo-Yun Chen & De-Quan Yu (2016): Aromatic glycosides from the whole plants of Iris japonica,
Journal of Asian Natural Products Research, DOI: 10.1080/10286020.2016.1188807
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Date: 20 June 2016, At: 04:49

Journal of asian natural Products research, 2016
http://dx.doi.org/10.1080/10286020.2016.1188807
Aromatic glycosides from the whole plants of Iris japonica
Guo-Ru Shi, Xin Wang, Yan-Fei Liu, Chun-Lei Zhang, Yan Wang, Li Li, Gang Ni, Ruo-Yun
Chen and De-Quan Yu
state Key laboratory of Bioactive substance and function of natural Medicines, institute of Materia Medica,
chinese academy of Medical sciences and Peking union Medical college, Beijing 100050, china
ABSTRACT
ARTICLE HISTORY
received 7 March 2016
accepted 9 May 2016
Phytochemical investigation on the whole plants of Iris japonica
led to the isolation of four new aromatic glycosides. Their
structures including the absolute configurations were determined
by spectroscopic and chemical methods as (−)-4-hydroxy-3-
methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8S)-(4-hydroxy-3-
methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside
(1), (−)-4-hydroxy-3-methoxyacetophenone4-O-β-d-{6-O-[4-O-(7S,8R)-
(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-
glucopyranoside (2), (−)-4-hydroxy-3-methoxy acetophenone
4-O-β-d-{6-O-[4-O-(7R,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-
3-methoxybenzoyl]}-glucopyranoside (3), (−)-4-hydroxy-3-methoxy
KEYWORDS
Iris japonica; aromatic
glycosides; chiral resolution;
erythro-threo isomer; cd
difference spectrum
acetophenone
4-O-β-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-3-methoxy-
phenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside
(4), respectively.
1. Introduction
e genus Iris belongs to the Iridaceae family, which consists of approximately 800 species
worldwide. In China, there are 71 species and 7 varieties, mostly distributed in the northwest,
the southwest, and the northeast of China [1]. Iris tectorum is a representative plant of the
Iridaceae family, the rhizomes of which are called “chuan she gan” in China. It has been com-
monly used for treatment of sore throats [2]. Iris japonica mainly distributes in the southwest of
China, and has been used as a folk medicine for the treatment of traumatic injury and relieving
constipation by purgation [3]. Previous studies of I. japonica led to the identification of nine
isoflavones and four iridals from this plant [4,5]. In our present investigation on the compo-
nents of this plant material, four new aromatic glycosides have been characterized (Figure 1).
e isolation and structure determination of the new isolates are reported in this article.
2. Results and discussion
Compound 1 was obtained as a white amorphous powder, and its molecular formula
C33H38O15 was deduced by HRESIMS (m/z 697.2108 [M + Na]+). e IR spectrum showed
CONTACT de-Quan Yu
dqyu@imm.ac.cn
© 2016 informa uK limited, trading as taylor & francis Group

2
G.-R. Shi eT aL.
Figure 1. structures of compounds 1–4.
absorption bands for hydroxyl (3239 cm−1), carbonyl (1673 cm−1), and aromatic (1402, 1452,
1
and 1595 cm−1) groups. e H NMR spectrum of 1 (Table 1) showed signals attributed
to three 1, 3, 4-trisubstitued aromatic rings at δH 7.44 (H-2), 7.15 (H-5), and 7.32 (H-6);
δH 7.35 (H-2″), 7.14 (H-5″), and 7.50 (H-6″); δH 7.00 (H − 2���), 6.66 (H − 5���), and 6.79
(H − 6���), a methyl singlet, three methoxys, two oxygenated methines, and an oxygenated
methylene. Acid hydrolysis of 1 gave a d-glucose, which was clarified by GC analysis. e
anomeric proton at δ 5.13 (H-1′) with a large coupling constant (3JH1′, H2′ =7.5 Hz) suggested
the presence of a β-glucopyranosyl moiety. e 13C NMR spectrum of 1 showed 33 carbon
resonances comprising 18 aromatic, a ketone carbonyl, an ester carbonyl, a methyl, three
methoxy, two oxygenated methine, an oxygenated methylene, and six glucopyranosyl car-
bon signals. e spectral data of 1 were in good agreement with those of scroneoside B [6]
except for the presence of an additional phenylglycerol unit [7,8].
In the HMBC spectrum of 1, correlations of H-2/C-4, C-6, and C-7; H-6/C-1, C-4, C-5,
and C-7; OCH3-3/C-3; CH3/C-1 and C-7, suggested the existence of 4-oxy-3-methoxy
acetophenone moisty, which was supported by a correlation between H-2 and OCH3-3 in
the ROESY spectrum. e HMBC spectrum also showed correlations of H-2″/C-1″, C-3″,
C-4″, C-6″, and C-7″; H-5″/C-1″, C-3″, C-4″, and C-6″; H-6″/C-1″, C-2″, C-4″, C-5″,
and C-7″; and OCH3-3″/C-3″, in combination with chemical shifs of these proton and
coupling patterns, indicated that there was a 4″-hydroxy-3″-methoxybenzoyloxy moiety.
In addition, correlations of H − 7���/H − 1���, C − 2���, C − 6���, C − 8���, and C − 9���; H − 2���
/
;
C − 1���
C − 6���
,
/
C − 3���
C − 1���
,
,
C − 4���
C − 2���
,
,
C − 6���, andC − 7��� C − 3���
;
H − 5���
/
C − 1���
,
,
C − 4���, andC − 6���
C − 3��� and C − 7���; and OCH3 − 1��� C − 3���, together with their
/
ꢀꢀꢀ
ꢀꢀꢀ
shifs, demonstrated the presence of a 4 -hydroxyl-3 - methoxyphenylglycerol moiety. is
was supported by 1H–1H COSY correlations of H − 7���/H − 8���/H2 − 9���; H − 5���/H − 6���.
Furthermore, HMBC correlations of H-1′/C-4 and H2-6′/C-7″ indicated that the 4-oxy-3-
methoxy acetophenone and 4″-hydroxyl-3″-methoxybenzoyloxy units were connected at
C-1′ and C-6′ of the β-glucopyranosyl moiety, respectively. Meanwhile, HMBC correlation
of H − 8���/C-4″ suggested a linkage between C − 8��� and C-4″.
e stereochemistry of 1 was elucidated by a comprehensive analysis of the
NMR and CD difference data of 1 (Figure 2). e Δ ꢀC8ꢀꢀꢀ
value (11.8 ppm) sug-
–C7ꢀꢀꢀ
ꢀꢀꢀ
ꢀꢀꢀ
gested an 7 , 8 -erythro configuration of 1 [9–12]. In the CD difference spec-
ꢀꢀꢀ
trum of 1, a positive Cotton effect at 238 nm indicated the 8 S configuration [12].
erefore, compound 1 was determined as (−)-4-hydroxy-3-methoxyacetophenone

JouRNaL oF aSiaN NaTuRaL PRoDuCTS ReSeaRCh
3
Table 1. 1h nMr and 13c nMr spectroscopic data of compounds 1–4a.
No
1
2
3
4
1
2
3
4
5
6
7
130.8
110.9 7.43d (1.9)
148.6
150.3
114.0 7.14 d (8.5)
130.9
111.0 7.44 d (2.0)
148.7
150.4
114.2 7.16 d (8.5)
130.8
110.0 7.44 d (2.0)
148.6
131.0
110.0
148.8
150.4
114.2
122.5
196.7
55.7
7.44 d (1.9)
150.3
7.15 d (8.5)
114.1 7.16 d (8.5)
122.3 7.32 dd (8.5, 2.0)
196.5
7.32 dd (8.5, 1.9) 122.3 7.32 dd (8.5, 1.9) 122.4 7.32 dd (8.5, 2.0)
196.4
55.4 3.80 s
196.7
55.5 3.80 s
oMe-3
3.80 s
55.6 3.80 s
Me
1′
2′
3′
4′
5′
6′a
6′b
1′′
2′′
3′′
4′′
5′′
6′′
7′′
2.46 s
26.3 2.46 s
26.4 2.47 s
26.3 2.47 s
26.4
99.2
73.1
76.7
70.2
74.1
64.0
5.13 d (7.5 )
3.25–3.82 m
3.25–3.82 m
3.25–3.82 m
3.25–3.82 m
4.55 d (12.0)
4.20 dd (12.0, 7.5)
99.0 5.13 d (7.3 )
73.0 3.25–3.82 m
76.6 3.25–3.82 m
70.1 3.25–3.82 m
73.9 3.25–3.82 m
63.9 4.55 d (12.0)
99.2 5.13 d (7.5 )
73.1 3.23–3.80 m
76.7 3.23–3.80 m
70.2 3.23–3.80 m
74.0 3.23–3.80 m
64.0 4.57 d (11.8)
99.1 5.13 d (7.5 )
73.0 3.25–3.82 m
76.7 3.25–3.82 m
70.1 3.25–3.82 m
74.0 3.25–3.82 m
64.0 4.57 d (11.8)
4.20 dd (11.8, 7.5)
121.5
112.7 7.40 d (2.0)
148.9
153.1
113.6 7.17 d (8.5)
123.1 7.52 dd (8.5, 2.0)
165.2
4.20 dd (12.0,7.5)
4.20 dd (11.8, 7.5)
121.4
121.5
121.6
112.8
149.1
153.2
113.7
123.3
165.4
55.9
7.35 d (1.9)
112.7 7.35 d (1.9)
148.9
152.7
112.8 7.40 d (2.0)
149.1
152.8
7.14 d (8.5)
113.6 7.13 d (8.5)
113.8 7.17 d (8.5)
7.50 dd (8.5, 1.9) 123.1 7.48 dd (8.5, 1.9) 123.2 7.52 dd (8.5, 2.0)
165.2
55.6 3.71 s
132.9
165.4
55.7 3.77 s
132.9
oMe-3′′ 3.71 s
ꢀꢀꢀ
55.8 3.78 s
132.9
132.9
1
ꢀꢀꢀ
7.00 d (1.7)
111.5 6.99 d (1.6)
147.0
111.6 6.98 d (1.7)
147.1
111.0 6.97 d (1.6)
147.1
111.1
147.2
145.7
114.9
119.2
71.3
2
ꢀꢀꢀ
3
ꢀꢀꢀ
145.5
145.6
145.6
4
ꢀꢀꢀ
6.66 d (8.0)
114.6 6.65 d (8.0)
114.7 6.68 d (8.0)
114.7 6.68 d (8.0)
119.1 6.77 dd (8.0, 1.6)
71.2 4.72 d (4.7)
83.6 4.49–4.50 m
60.2 3.58–3.60 m
5
ꢀꢀꢀ
6.79 dd (8.0, 1.7) 119.6 6.78 dd (8.0, 1.6) 119.7 6.77 dd (8.0, 1.6)
6
ꢀꢀꢀ
4.71 d (5.0)
4.52–4.53 m
3.62–3.64 m
71.5 4.71 d (4.5)
83.3 4.52–4.53 m
60.1 3.61–3.63 m
71.5 4.72 d (4.7)
83.3 4.49 –4.50 m
60.3 3.59–3.60 m
7
ꢀꢀꢀ
83.7
8
ꢀꢀꢀ
60.3
9
3.25–3.27 m
3.70 s
3.25–3.27 m
55.7 3.70 s
3.25–3.26 m
55.9 3.72 s
3.25–3.26 m
55.4 3.72 s
ꢀꢀꢀ
55.6
oMe-3
a1h nMr data (δ) were measured in dMso-d6 at 600 Mhz and 13c nMr data (δ) were measured in dMso-d6 at 150 Mhz
for 1–4. coupling constants (J) in hz are given in parentheses. the assignments were based on 1h–1h cosY, hsQc, and
hMBc experiments.
4-O-β-d-{6-O-[4-O-(7R,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-
methoxybenzoyl]}-glucopyranoside.figure 2. cd difference spectra of compounds 1 (—)and 2 (---).
IR, HRESIMS, and NMR spectroscopic data of compound 2 are almost identical to those
of 1. However, 1 and 2 were separable by chiral HPLC with retention times of 15.8 and
26.3 min (Experimental Section), respectively. e Δ ꢀ ꢀꢀꢀ–C7ꢀꢀꢀ
value (11.8 ppm) suggested
that 2 was another erythro-isomer of 1 [9–12]. e CD Cd8ifference spectrum (Figure 2) of 2
ꢀꢀꢀ
showed negative Cotton effect at 238 nm indicated the 8 R configuration [12]. us, 2 was
determined to be (−)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8R)-(4-
hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside.
e spectroscopic data of 3 were similar to those of 1. Comparison of the NMR data of 1
value was 12.4 ppm in 3, while it was 11.8 ppm in 1 [9–12].
and 3, indicated that Δ ꢀ ꢀꢀꢀ–C7ꢀꢀꢀ
is suggested that 3 wasCa8 threo-isomer of 1, which was further confirmed by 2D NMR data.
In the CD difference spectrum (Figure 3) of 3, a negative Cotton effect at 234 nm indicated

4
G.-R. Shi eT aL.
Figure 2. cd difference spectra of compounds 1 (—)and 2 (---).
Figure 3. cd difference spectra of compounds 3 (—) and 4 (---).
ꢀꢀꢀ
the 8 R configuration [12]. Hence, compound 3 was characterized as (−)-4-hydroxy-3-
methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8R)-(4-hydroxy-3-methoxyphenylglycerol-
8-yl)-3-methoxybenzoyl]}-glucopyranoside.
Spectroscopic data of compound 4 are almost identical to those of 3. However, 3 and 4
were separable by chiral HPLC with retention times of 15.4 and 25.6 min (Experimental
Section), respectively. In addition, the Δ ꢀC8ꢀꢀꢀ ꢀꢀꢀ (12.4 ppm) suggested that 4 was another
threo-isomer of 3 [9–12]. e CD difference sp–eCc7trum of 4 (Figure 3) showed positive Cotton
ꢀꢀꢀ
effect at 234 nm indicating the 8 S configuration [12]. Consequently, 4 was determined

JouRNaL oF aSiaN NaTuRaL PRoDuCTS ReSeaRCh
5
to be (−)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-3-
methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside.
3. Experimental
3.1. General experimental procedures
Optical rotations were measured with a JASCO P-2000 polarimeter (Tokyo, Japan), and
UV spectra with a JASCO V-650 spectrophotometer (JASCO). IR spectra were recorded
on a Nicolet 5700 FT-IR microscope instrument (FT-IR microscope transmission; ermo
Electron Corporation, Madison, WI, USA). CD spectra were recorded on a JASCO J-815
CD spectrometer (JASCO, Tokyo, Japan). NMR measurements were performed on Bruker
AV600 IIIHD spectrometers (Bruker Corp., Karlsruhe, Germany) in DMSO-d6. HRESIMS
were obtained using an Agilent 1100 series LC/MSD ion trap mass spectrometer (Agilent
Technologies Ltd., Santa Clara, CA, USA). Preparative HPLC was conducted using a
Shimadzu LC-6AD instrument with an SPD-20A detector and YMC-Pack ODS-A column
(250 × 10 mm, 5 μm). Chirality resolutions were performed on a DAICEL AD-H column
(250 × 4.6 mm, 5 μm; Daicel, Tokyo, Japan). Silica gel (200–300 mesh, Qingdao Marine
Chemical Factory, Qingdao, China), Sephadex LH-20 (Pharmacia Biotech AB, Uppsala,
Sweden), Diaion HP 20 (Mitsubishi, Japan) and ODS (50 μm, YMC, Kyoto, Japan) were used
for column chromatography. Analytical thin-layer chromatography (TLC) was carried out
with GF254 plates (Qingdao Marine Chemical Factory). Spots were visualized by spraying
with 10% H2SO4 in 95% EtOH followed by heating.
3.2. Plant material
Whole plants of Iris japonica were collected in Yunnan Province, China, in May 2014, and
identified by associate Professor Lin Ma (Institute of Materia Medica, Chinese Academy
of Medical Sciences & Peking Union Medical College). A voucher specimen (ID-S-2618)
has been deposited at the Herbarium of Institute of Materia Medica, Chinese Academy of
Medical Sciences & Peking Union Medical College, Beijing.
3.3. Extraction and isolation
e air-dried whole plants (50 kg) of I. japonica were extracted with 95% EtOH (3 × 100 L)
under reflux. e extracts were combined and concentrated under a vacuum to give a res-
idue (2.1 kg), which was suspended in water and partitioned successively with EtOAc and
n-BuOH. e n-BuOH soluble fraction (520 g) was subjected to a Diaion HP20 column
eluted with a stepwise gradient of EtOH/H2O (10:90, 30:70, 50:50, 70:30, and 95:5, v/v) to
afford five fractions. Afer removing the solvent, the EtOH/H2O (50:50) eluate (178 g) was
subsequently separated by silica gel chromatography eluting with CHCl3/MeOH (50:1–0:1,
v/v) to afford six fractions (A–F) based on TLC analysis. e FD (35 g) that eluted with 10:1
CHCl3/MeOH was further chromatographed on a reversed-phase C18 silica gel column
(40 × 6 cm), eluted with 10, 30, 50, 70, and 100% MeOH in H2O, to afford FD1 to FD8. FD2
(5 g) was purified using Sephadex LH-20 (MeOH) to give FD2-1 to FD2-5. FD2-2 (67 mg) was
isolated by a silica gel (CHCl3/MeOH 20:1) to yield FD2-2-1 and FD2-2-2. FD2-2-2 (10.5 mg) was

6
G.-R. Shi eT aL.
isolated by preparative HPLC separation (20% MeCN in H2O, 3 ml/min) to afford fractions
FD2-2-2–1 (3.6 mg, tR 46 min) and FD2-2-2-2 (3.8 mg, tR 42 min). Finally, chiral resolution on
FD2-2-2-1 and FD2-2-2-2 were performed by a DAICEL AD-H column (50% isopropanol in hex-
ane, 0.6 ml/min) to yield 1 (1.2 mg) and 2 (1.5 mg), 3 (1.2 mg) and 4 (1.6 mg), respectively.
3.3.1. (−)-4-Hydroxy-3-methoxyacetophenone 4-O-β- -{6-O-[4-O-(7R,8S)-(4-hydroxy-
d
3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (1)
20
White amorphous powder, [α] −36.3 (c 0.08, MeOH); UV (MeOH) λmax (log ε) 203 (5.11),
D
222 (4.86), 265 (4.62) nm; CD (MeOH) Δε225 nm −2.92, Δε257 nm −1.50, Δε290 nm −0.65; IR
1
νmax 3239, 1718, 1673, 1595, 1516 cm−1; H NMR (DMSO-d6, 600 MHz) and 13C NMR
(DMSO-d6, 150 MHz) spectral data see Table 1; HRESIMS: m/z 697.2108 [M + Na]+ (calcd
for C33H38NaO15, 697.2103).
3.3.2. (−)-4-Hydroxy-3-methoxyacetophenone 4-O-β-d-{6-O-[4-O-(7S,8R)-
(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (2)
20
White amorphous powder, [α] −27.9 (c 0.08, MeOH); UV (MeOH) λmax (log ε) 203 (5.10),
222 (4.81), 265 (4.54) nm; CDD(MeOH) Δε234 nm −5.33, Δε299 nm +1.10; IR νmax 3258, 1716,
1674, 1595, 1515 cm−1; 1H NMR (DMSO-d6, 600 MHz) and 13C NMR (DMSO-d6, 150 MHz)
spectral data see Table 1; HRESIMS: m/z 697.2106 [M + Na]+ (calcd for C33H38NaO15,
697.2103).
3.3.3. (−)-4-Hydroxy-3-methoxyacetophenone 4-O-β-d-{6-O-[4-O-(7R,8R)-(4-
hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (3)
20
White amorphous powder, [α] −9.4 (c 0.08, MeOH); UV (MeOH) λmax (log ε) 203 (5.11),
222 (4.81), 265 (4.54) nm; CDD(MeOH) Δε222 nm −1.52, Δε256 nm −0.97; IR νmax 3363, 1716,
1689, 1612, 1592 cm−1; 1H NMR (DMSO-d6, 600 MHz) and 13C NMR (DMSO-d6, 150 MHz)
spectral data see Table 1; HRESIMS: m/z 697.2103 [M + Na]+ (calcd for C33H38NaO15,
697.2103).
3.3.4. (−)-4-Hydroxy-3-methoxyacetophenone 4-O-β-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-
3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (4)
20
White amorphous powder, [α] −6.5 (c 0.08, MeOH); UV (MeOH) λmax (log ε) 203 (5.07),
222 (4.77), 265 (4.46) nm; CDD(MeOH) Δε223 nm −1.39, Δε273 nm +0.21; IR νmax 3379, 1717,
1688, 1611, 1594 cm−1; 1H NMR (DMSO-d6, 600 MHz) and 13C NMR (DMSO-d6, 150 MHz)
spectral data see Table 1; HRESIMS: m/z 697.2104 [M + Na]+ (calcd for C33H38NaO15,
697.2103).
3.4. Acid hydrolysis of 1–4
Each compound (1 mg) was individually refluxed in 2 M HCl (2.0 ml) at 80 °C for 15 h.
e reaction mixture was extracted with EtOAc, and the H2O phase was evaporated under
vacuum, diluted repeatedly with H2O, and evaporated in vacuo to furnish a neutral residue.
e residue was dissolved in anhydrous pyridine (1.0 ml), to which 1 mg of L-cysteine
methyl ester hydrochloride was added. e mixture was stirred at 60 °C for 2 h, and afer
evaporation in vacuo to dryness, 0.1 ml of N-trimethylsilylimidazole was added; the mixture
was kept at 60 °C for another 2 h. e reaction mixture was partitioned between n-hexane

JouRNaL oF aSiaN NaTuRaL PRoDuCTS ReSeaRCh
7
and H2O (1.0 ml each), and then the n-hexane extract was analyzed by GC under the fol-
lowing conditions: capillary column, HP-5 (30 m × 0.25 mm, with a 0.25 μm film; Dikma);
detection, FID; detector temperature, 280 °C; injection temperature, 250 °C; initial temper-
ature, 160 °C, then raised to 280 °C at 5 °C/min, final temperature maintained for 10 min;
carrier gas, N2. From the acid hydrolysate of each compound, d-glucose was confirmed by
comparison of the retention time of its derivative with that of authentic sugar derivatized
in a similar way, which showed a retention time of 18.91 min, respectively.
Acknowledgments
e authors gratefully acknowledge grants from the National Natural Science Foundation (No.
21472245) and the State Key Laboratory of Bioactive Substance and Function of Natural Medicines
(No. GTZC201101), Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking
Union Medical College.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
is work was supported by the National Natural Science Foundation [grant number 21472245];
the State Key Laboratory of Bioactive Substance and Function of Natural Medicines [grant number
GTZC201101], and Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking
Union Medical College.
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