Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant evaluation of the constituents from Angelica dahurica roots

Article abstract of DOI:10.1007/s11418-019-01375-8

Two undescribed phenolic compounds, angelicols A (1) and B (2) and one undescribed coumarin rhamnoside, angelicoside A (3), together with 17 known compounds (4–20) were isolated from the roots of Angelica dahurica. Their structures were characterized by physical data analyses such as NMR, HRESIMS, and X-ray diffraction. Compounds 2, 3, 5, 6 and L-ascorbic acid (positive control) exhibited obvious DPPH radical scavenging activities with IC₅₀ values of 0.36?mM, 0.43?mM, 0.39?mM, 0.44?mM, 0.25?mM, respectively. At a concentration of 25?μM, all compounds showed weaker tyrosinase inhibition activities (%inhibition < 5%) than kojic acid (26.00 ± 0.67%, IC₅₀ = 44.29 ± 0.06?μM).

Full text of DOI:10.1007/s11418-019-01375-8

Journal of Natural Medicines
https://doi.org/10.1007/s11418-019-01375-8
NOTE
Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant
evaluation of the constituents from Angelica dahurica roots
Penghua Shu1 · Junping Li1 · Yingying Fei1 · Huiqing Zhu1 · Mengzhu Yu1 · Anqi Liu1 · Haoying Niu1 · Simin Zou1 ·
Xialan Wei2 · Zhiyu Ju1 · Zhihong Xu1
Received: 3 October 2019 / Accepted: 16 November 2019
© The Japanese Society of Pharmacognosy 2019
Abstract
Two undescribed phenolic compounds, angelicols A (1) and B (2) and one undescribed coumarin rhamnoside, angelicoside
A (3), together with 17 known compounds (4–20) were isolated from the roots of Angelica dahurica. Their structures were
characterized by physical data analyses such as NMR, HRESIMS, and X-ray difraction. Compounds 2, 3, 5, 6 and L-ascor-
bic acid (positive control) exhibited obvious DPPH radical scavenging activities with IC50 values of 0.36 mM, 0.43 mM,
0.39 mM, 0.44 mM, 0.25 mM, respectively. At a concentration of 25 μM, all compounds showed weaker tyrosinase inhibition
activities (%inhibition<5%) than kojic acid (26.00 0.67%, IC50 =44.29 0.06 μM).
Keywords Angelica dahurica · Tyrosinase · X-ray difraction · Antioxidant
Introduction
chemical constituents with strong anti-tyrosinase and anti-
oxidant activities, the ethanol extracts of Angelica dahurica
roots were explored, which provided three new compounds
(1–3) and 17 known compounds (4–20) (Fig. 1). In the sub-
sequent antioxidant and anti-tyrosinase assays, compounds
2, 3, 5, and 6 exhibited obvious DPPH radical scavenging
activities with IC50 values close to that of L-ascorbic acid.
Angelica dahurica, a commonly used medicinal plant,
belongs to the family Apiaceae. Its roots are widely uti-
lized in Chinese medicine to treat various diseases such as
toothache, headache, stufy nose, supraorbital neuralgia,
and nasosinusitis [1]. Previous investigations revealed that
the major chemical constituents of the root part are cou-
marins [2–8]. Many of these coumarins showed signifcant
cytotoxic [2], anti-inflammatory [5, 7], antioxidant [6],
and tyrosinase inhibitory activities [9]. In addition, alka-
loids [10], polysaccharides [11], and neoligans [12] have
also been reported from Angelica dahurica. In a search for
Results and discussion
Compound 1 was obtained as cubic crystals. The molecu-
lar formula C10H14O3, with four degrees of unsaturation,
was established based on its quasi-molecular ion peak at
m/z 183.1017 [M+H]+ (calcd for C10H15O3, 183.1016) in
the HRESIMS spectrum. Its IR spectrum showed absorp-
tion bands for hydroxyl (3423, 3257 cm–1) and aromatic
Electronic supplementary material The online version of this
article (https://doi.org/10.1007/s11418-019-01375-8) contains
supplementary material, which is available to authorized users.
1
ring (1610, 1596, 1513, 1448 cm–1). The H-NMR spec-
* Penghua Shu
trum of 1 revealed the signals of an AAʹBBʹ spin system
at δ 7.14 (dd, J = 7.6 Hz, H-5, H-7), 6.79 (d, J = 7.6 Hz,
H-4 and H-8), which showed a 1,4-disubstituted phenyl
ring. The proton signals at δ 3.46 (1H, dq, J=14.8, 6.8 Hz,
H-1ʹa), 3.35 (1H, dq, J=14.8, 6.8 Hz, H-1ʹb), and 1.18 (3H,
t, J=6.8 Hz, H-2ʹ), and the 13C-NMR signals at δ 64.5 (C-1ʹ)
and 15.5 (C-2ʹ) demonstrated the presence of an ethoxyl
shupenghua@yeah.net
* Zhihong Xu
xuzhihong1980@xcu.edu.cn
1
School of Chemistry and Chemical Engineering, Xuchang
University, 88 Bayi Road, Xuchang 461000, Henan,
People’s Republic of China
2
1
School of Information Engineering, Xuchang
group. The remaining H-NMR signals at δ 4.34 (1H, dd,
University, 88 Bayi Road, Xuchang 461000, Henan,
People’s Republic of China
J=8.4, 3.6 Hz, H-1) and δ 3.64 (1H, dd, J=11.2, 8.4 Hz,
Vol.:(0123456789)
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Journal of Natural Medicines
Fig. 1 Structures of compounds 1–20
Fig. 2 Key 1H-1H COSY and HMBC correlations for compound 1
H-2a), δ 3.56 (1H, dd, J=11.2, 3.6 Hz, H-2b) were ascribed
to the moiety –O–CHCH2–O–. The speculations above were
1
confrmed by the key H−1H COSY, HSQC, and HMBC
correlations shown in Fig. 2. The HMBC correlations from
H-1ʹ to C-1 indicated that the ethoxyl group was connected
with C-1. The HMBC correlations from H-1 to C-3, C-4,
and C-8 suggested the –O–CHCH2– was linked to C-3. To
determine the absolute confguration of C-1, compound 1
was recrystallized carefully in acetone and the crystal was
subjected to single-crystal X-ray difraction analysis with
Cu Kα radiation. The absolute confguration of compound
1 was assigned as 1R by the calculated Flack parameter
of−0.01(6) (Fig. 3). Therefore, the structure of compound
1 was identifed as (1R)-ethoxyl-1-(4-hydroxyphenyl)ethane-
1,2-diol, named as angelicol A.
Fig. 3 ORTEP drawing of compound 1
quasi-molecular ion peak at m/z 355.1158 [M+Na]+ (calcd
for C18H20O6Na, 355.1158) in the HRESIMS spectrum,
implying the presence of nine degrees of unsaturation. The
IR absorption bands at 3409 and 1716 cm–1 were attributed
to hydroxyl and carbonyl groups, respectively. The 1H-NMR
spectrum of 2 revealed signals of an aromatic ABX spin
system at δ 6.65 (1H, d, J=8.0 Hz, H-6´), 6.72 (1H, br d,
J=8.0 Hz, H-5ʹ), 6.84 (1H, br s, H-2ʹ), and an AAʹBBʹ sys-
tem at δ 6.80 (2H, d, J = 8.0 Hz, H-5, H-7), 7.23 (2H, d,
J=8.0 Hz, H-4, H-8). The former indicated the presence of
Compound 2 was obtained as a colorless oil. Its molec-
ular formula was established as C18H20O6 based on the
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Journal of Natural Medicines
a 1,3,4-trisubstituted aromatic ring, and the latter suggested
a 1,4-disubstituted aromatic ring. In the 1H-NMR and 1H-1H
COSY spectra of 2, the signals at δ 4.09 (2H, d, J=5.6 Hz,
H-2) and 4.81 (1H, t, J=5.6 Hz, H-1) showed the existence
of a –CH(OH)–CH2O– subunit, while the signals at δ 2.58
(2H, t, J = 8.0 Hz, H-8ʹ) and 2.81 (2H, t, J = 8.0 Hz, H-7
ʹ) indicated the existence of a –CH2–CH2– subunit. Based
on the key HMBC signals such as correlations from H-1
to C-3, C-4, and C-8, from H-2 to C-9ʹ and correlations
from H-7ʹ to C-1ʹ, C-2ʹ, and C-6ʹ, the planar structure of
2 was established as shown in Fig. 4. Furthermore, com-
pound 2 showed positive optical activity with+[ꢀ]204.3° (c
0.09, CH3OH) and the confguration of C-1 was pDroposed
as S after comparison with the related analogs such as (S)-
1-(4-hydroxyphenyl)ethane-1,2-diol [13], phomoaspardiol
[14], phomopsuidiol [15], (S)-2-hydroxy-2-phenylethyl
acetate [16], and (R)-2-hydroxy-2-phenylethyl acetate [17]
(Fig. 5). Thus, the structure of compound 2 was elucidated
as (1S)-2-O-dihydroferuloyl-1-(4-hydroxyphenyl)ethane-
1,2-diol, named as angelicol B.
the quasi-molecular ion peak at m/z 393.1552 [M + H]+
(calcd for C20H25O8, 393.1549) in the HRESIMS spectrum,
implying the presence of nine degrees of unsaturation. The
1H-NMR spectrum of 3 revealed the presence of a marmesin
unit [δ 6.18 (1H, d, J=9.6 Hz, H-3), 7.84 (1H, d, J=9.6 Hz,
H-4), 7.39 (1H, s, H-5), 6.70 (1H, s, H-8), 4.82 (1H, dd,
J=8.8, 8.4 Hz, H-2ʹ), 3.26 (2H, m, H-3ʹ), 1.37 (3H, s, H-5ʹ),
1.31 (3H, s, H-6ʹ)], and one l-rhamnose unit [δ 5.07 (1H,
d, J = 1.2 Hz, H-1ʹʹ), 3.63 (1H, dd, J= 1.2, 2.8 Hz, H-2ʹʹ),
3.41 (1H, dd, J=2.8, 9.6 Hz, H-3ʹʹ), 3.30 (1H, dd, J=9.6,
7.2 Hz, H-4ʹʹ), 3.65 (1H, dq, J = 7.2, 6.4 Hz, H-5ʹʹ), 1.15
(3H, d, J=6.4 Hz, H-6ʹʹ) (Table 1). The α-l-Rha was char-
acterized by the small coupling constant J1ʹʹ,2ʹʹ (1.2 Hz) and
supported by the key NOESY correlations from H-1ʹ to H-4ʹʹ
and H-6ʹʹ (Fig. 6). The key HMBC correlation from H-1ʹʹ to
C-4ʹ defned C-4ʹ of marmesin as the site of O-glycosylation.
Moreover, the acid hydrolysis of 3 aforded marmesin (4)
[18], which was also isolated as a natural product in this
study. The [ꢀ]20 of 4 was measured to be + 11.7° (c 0.08,
CHCl3). Thus,Dthe aglycone was established as marmesin,
rather than its R-isomer nodakenetin ([ꢀ]20–25.4°) [19].
Based on the evidences described above, tDhe structure of
compound 3 was fnally determined as shown in Fig. 6,
named as angelicoside A.
Compound 3 was also obtained as a colorless oil. Its
molecular formula was established as C20H24O8 based on
By comparing their NMR data with those published
literature values, the known compounds 4−20 were iden-
tifed as follows: marmesin (4) [18], (1S)-2-O-Z-feruloyl-
1-(4-hydroxyphenyl)ethane-1,2-diol (5) [20], (1S)-2-O-
E-feruloyl-1-(4-hydroxyphenyl)ethane-1,2-diol (6) [20],
xanthoarnol (7) [21], pangelin (8) [2], xanthotoxol (9) [22],
xanthotoxin (10) [23], bergapten (11) [24], isopimpinellin
(12) [23], imperatorin (13) [25], isoimperatorin (14) [26],
phellopterin (15) [27], cnidilin (16) [28], heraclenin (17)
[28], byakangelicol (18) [29], (+)-oxypeucedanin (19) [30],
Fig. 4 Key 1H-1H COSY and HMBC correlations for compound 2
Fig. 5 Optical rotations of compound 2 and its analogs
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Journal of Natural Medicines
Fig. 6 Key 1H-1H COSY, HMBC, and NOESY correlations for compound 3
Table 1 1H-NMR and 13C-NMR (CD3OD) of compound 3
Table 2 DPPH radical scavenging activity of compounds 1–20 and
l-ascorbic acid
Position δC
δH (mult, J in
Position δC
δH (mult, J in Hz)
Hz)
Compounds DPPH radical
scavenging activ-
ity (%)
Compounds
DPPH radical
scavenging activity
(%)
2
3
4
4a
5
163.9
3ʹ
4ʹ
30.6 3.26 (m)
79.1
112.3 6.18 (d, 9.6)
146.4 7.84 (d, 9.6)
114.2
125.0 7.39 (s)
127.3
1
26.26 0.46
74.40 0.35
69.80 0.36
28.05 0.42
72.74 0.30
71.69 0.28
22.67 0.48
23.62 1.93
66.03 0.30
27.21 0.44
11.96 0.42
12
13
14
15
16
17
18
19
20
21.74 0.80
23.62 1.93
20.34 0.54
25.12 0.34
22.79 1.25
24.70 0.86
25.15 0.38
34.30 0.51
44.26 0.29
5ʹ
6ʹ
22.8 1.37 (s)
22.3 1.31 (s)
2
3
1ʹʹ
2ʹʹ
3ʹʹ
4ʹʹ
5ʹʹ
6ʹʹ
96.3 5.07 (d, 1.2)
73.6 3.63 (dd, 1.2, 2.8)
72.4 3.41 (dd, 2.8, 9.6)
74.1 3.30 (dd, 9.6, 7.2)
70.0 3.65 (dq, 7.2, 6.4)
18.0 1.15 (d, 6.4)
4
6
5
7
8
8a
2ʹ
165.4
98.2 6.70 (s)
157.1
6
7
8
92.1 4.82 (dd, 8.8,
9
8.4)
10
11
l-ascorbic acid 83.32 0.26
The radical scavenging efects of compounds 1–20 and l-ascorbic
acid were measured at a concentration of 1 mM. Three independ-
ent experiments were performed and the results were expressed as
mean SEMs
oxypeucedanin hydrate (20) [31], respectively. Compounds
1−3 and 5−6 were reported from Angelica dahurica for the
frst time.
The mushroom tyrosinase inhibitory activities of com-
pounds 1–20 and kojic acid (positive control) were evaluated
at a concentration of 25 μM. All isolated compounds showed
weaker tyrosinase inhibition activities (%inhibition< 5%)
than kojic acid (26.00 0.67%, IC50 =44.29 0.06 μM).
DPPH radical scavenging assays were conducted to assess
the radical scavenging efects of the 20 isolated compounds
(1–20) at a concentration of 1 mM, with l-ascorbic acid
as the positive control. The results were shown in Table 2.
Compounds 2 and its two derivatives 5–6 exhibited consid-
erable DPPH radical scavenging activities: 74.40 0.35%,
IC50 = 0.36 mM for 2; 72.74 0.30%, IC50 = 0.39 mM for
5; 71.69 0.28%, IC50 = 0.44 mM for 6; 83.32 0.26%,
IC50 = 0.25 mM for l-ascorbic acid. Just as Moon’s group
has reported, compounds with a 4-hydroxy-3-methoxyl sub-
stituent on the phenyl ring usually exhibited obvious DPPH
radical scavenging activity [32, 33]. Interestingly, the new
glycoside 3 showed a good radical scavenging activity with
69.80 0.36% inhibition, while its aglycone 4 showed a
weak activity. Perhaps the sugar moiety played a key role in
the process of DPPH radical scavenging.
Experimental section
General experimental procedures
Melting points (uncorrected) were measured on an X-5
microscopic melting point apparatus (Yuhua Instrument Inc.,
China). Optical rotations were determined on a Rudolph
Autopol IV polarimeter (589 nm, 20 °C). FT-IR and UV
spectra were determined using FTIR-650 and Puxi TU-1950
instruments, respectively. NMR spectra were recorded on a
Bruker AM-400 spectrometer. High-resolution electrospray
ionization mass spectra (HRESIMS) were carried out on a
Waters Xevo G2-XS QTof spectrometer, a Thermo Fisher
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Journal of Natural Medicines
Ultimate 3000 RSLC/Q spectrometer or a Bruker micrOTOF
II spectrometer. The X-ray difraction experiments were car-
ried out on a Rigaku XtaLAB synergy four-circle difractom-
eter with Cu Kα radiation (λ = 1.54184 Å). Column chro-
matography (CC) was performed using silica gel (Qingdao
Marine Chemical Inc., China), RP-C18 (50 μm, Fuji Silysia
Chemical Ltd., Japan), and Sephadex LH-20 (GE Healthcare
Bio-Sciences AB, Sweden). TLC was performed with silica
gel 60 F254 (Yantai Chemical Industry Research Institute).
Compound 1
Colorless cubic crystals. +[ꢀ]203.9° (c 0.25, CHCl3). mp
101 − 102 °C. IR (KBr) νmaxD3423, 3257, 1610, 1596,
1513, 1448 cm–1. UV λmax (MeOH) nm (log ε): 239 (2.8),
275 (2.8). HRESIMS m/z 183.1017 [M + H]+ (calcd for
1
C10H15O3, 183.1016). H-NMR (CDCl3) δ: 1.18 (3H, t,
J=6.8 Hz, H-2ʹ), 2.62 (1H, br s, OH), 3.35 (1H, dq, J=14.8,
6.8 Hz, H-1ʹb), 3.46 (1H, dq, J=14.8, 6.8 Hz, H-1ʹa), 3.56
(1H, dd, J = 11.2, 3.6 Hz, H-2b), 3.64 (1H, dd, J = 11.2,
8.4 Hz, H-2a), 4.34 (1H, dd, J = 8.4, 3.6 Hz, H-1), 6.09
(1H, br s, OH), 6.79 (d, J = 7.6 Hz, H-4, H-8), 7.14 (dd,
J = 7.6 Hz, H-5, H-7). 13C-NMR (CDCl3) δ: 15.5 (C-2ʹ),
64.5 (C-1ʹ), 67.6 (C-2), 82.3 (C-1), 115.6 (C-4, C-8), 128.4
(C-5, C-7), 131.0 (C-3), 155.9 (C-6).
Plant material
The fresh roots of Angelica dahurica were collected in
Yuzhou, People’s Republic of China, in August 2018. The
botanical identifcation was made by Prof. Lin Yang, School
of Life Science and Engineering, Lanzhou University of
Technology. A voucher specimen (SPH2018A) was depos-
ited in the herbarium of School of Chemistry and Chemical
Engineering, Xuchang University.
Compound 2
Colorless oil. +[ꢀ]204.3° (c 0.09, CH3OH). IR (KBr) νmax
D
3409, 1716, 1616, 1513, 1448 cm–1. UV λmax (MeOH)
Extraction and isolation
nm (log ε): 225 (2.9), 278 (3.5). HRESIMS m/z 355.1158
[M + Na]+ (calcd for C18H20O6Na, 355.1158). H-NMR
1
The roots of Angelica dahurica (10 kg) were extracted
with 95% EtOH at room temperature (3 × 50 L) to aford
a crude extract of 523 g after evaporation of the solvent
under vacuum. The extract was suspended in distilled H2O
and partitioned with EtOAc and n-BuOH. The EtOAc solu-
ble portion (137 g) was subjected to silica gel CC using
petroleum ether–EtOAc (100:0 to 1:2) as eluents to give
nine fractions F1–F9. The fraction F1 (eluted by petroleum
ether–EtOAc 100:1) was subsequently purifed using RP-C18
CC (MeOH–H2O, 85:15 to 100:0) to aford compounds
10 (3.3 mg), 11 (2.8 mg), 12 (4.1 mg), 13 (32.5 mg), 14
(24.7 mg), 15 (13.6 mg), 16 (7.8 mg), 18 (5.2 mg). The
fraction F2 (eluted by petroleum ether–EtOAc 70:1) was
further separated using Sephadex LH-20 column (CH2Cl2)
to give compounds 8 (4.3 mg), 9 (3.5 mg), and 17 (4.4 mg).
The fraction F5 (eluted by petroleum ether–EtOAc 50:1)
was passed through a RP-C18 CC eluted with MeOH-H2O
(90:10) to give seven subfractions (F5-1 to F5-7). The sub-
fraction F5-1 was chromatographed on the silica gel CC to
give compounds 19 (5.0 mg) and 20 (11.6 mg). The sub-
fraction F5-3 was purifed by RP-C18 CC (MeOH–H2O,
85:15) to give compounds 1 (10.7 mg) and 4 (7.9 mg). The
subfraction F5-5 was purified by Sephadex LH-20 col-
umn (CH2Cl2–MeOH 1:1) to aford compounds 5 (6.7 mg)
and 7 (14.8 mg). The fraction F8 (eluted by petroleum
ether–EtOAc 3:1) was further separated using Sephadex
LH-20 column (MeOH) to give four subfractions F8-1–F8-4.
After further purifcation with RP-C18 CC, the subfraction
F8-1 gave compound 2 (3.1 mg) and the subfraction F8-5
gave compounds 3 (8.4 mg) and 6 (5.2 mg).
((CD3)2CO) δ: 2.58 (2H, t, J= 8.0 Hz, H-8ʹ), 2.81 (2H, t,
J=8.0 Hz, H-7ʹ), 3.82 (3H, s, OMe), 4.09 (2H, d, J=5.6 Hz,
H-2), 4.46 (1H, br s, OH), 4.81 (1H, t, J=5.6 Hz, H-1), 6.65
(1H, br d, J=8.0 Hz, H-6ʹ), 6.72 (1H, br d, J=8.0 Hz, H-5ʹ),
6.80 (2H, d, J = 8.0 Hz, H-5, H-7), 6.84 (1H, br s, H-2ʹ),
7.23 (2H, d, J=8.0 Hz, H-4, H-8), 7.36 (1H, br s, OH), 8.33
(1H, br s, OH). 13C-NMR ((CD3)2CO) δ: 31.2 (C-7ʹ), 36.8
(C-8ʹ), 56.2 (–OMe), 70.0 (C-2), 71.9 (C-1), 112.8 (C-2ʹ),
115.7 (C-5ʹ), 115.8 (C-5, C-7), 121.5 (C-6ʹ), 128.4 (C-4,
C-8), 133.1 (C-1ʹ), 133.5 (C-3), 145.9 (C-4ʹ), 148.3 (C-3ʹ),
157.8 (C-6), 173.1 (C-9ʹ).
Compound 3
Colorless oil. [ꢀ]20–66.1° (c 0.26, CH3OH). IR (KBr) νmax
D
3428, 1733, 1625, 1567, 1394 cm–1. UV λmax (MeOH)
nm (log ε): 225 (4.2), 248 (3.6), 335 (3.9). HRESIMS m/z
1
393.1552 [M + H]+ (calcd for C20H25O8, 393.1549). H-
NMR and 13C-NMR data (CD3OD), see Table 1.
Acid hydrolysis of 3
The acid hydrolysis of 3 was conducted according to the lit-
erature with slight modifcations [18]. Compound 3 (4.0 mg)
was dissolved in 3.0% HCl (4 mL) and heated at 85 °C for
1 h. The reaction mixture was diluted with EtOAc, washed
with water, dried (Na2SO4), concentrated and purifed by
the silica gel CC to give marmesin (4) [18] and l-rham-
nose, +[ꢀ]205.2° (c 0.05, H2O) [reported: +[ꢀ]202.4° (c 1,
D
H2O)] [34]D.
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Journal of Natural Medicines
Experiments were performed in triplicate. The DPPH radi-
cal scavenging activity was calculated by radical scavenging
activity (%)=[1−(As/Ac)]×100, where Ac is the absorbance
of the non-treated control and As is the absorbance of tested
compound.
Single‑crystal X‑ray difraction analysis
of compound 1
The single-crystal difraction data of compound 1 were col-
lected on a Rigaku XtaLAB synergy four-circle difractom-
eter with Cu Kα radiation (λ=1.54178 Å), with the CrysA-
lisPro software (version 1.171.39.34b) for data reduction and
analysis. The single-crystal difraction data were collected
at 150 K and the structures were solved by direct methods
and refned by full-matrix least-squares method on F2 using
SHELX algorithms in Olex2. All non-hydrogen atoms
were refned with anisotropic displacement parameters. All
hydrogen atoms were generated geometrically. The X-ray
crystallographic data have been deposited at the Cambridge
Crystallographic Data Centre (CCDC, ref. No. 1955041).
Crystallographic Data of 1: C10H14O3, M = 182.21,
monoclinic, Cc, a = 12.3276(6) Å, b = 5.0380(1) Å,
c=17.4645(3) Å, α=γ=90°, β=96.324(1), V=1099.64(3)
Å3, T = 150 K, Z = 4, Dcalcd = 1.276 g cm−3, µ (Cu Kα)
0.77 mm−1, crystal size 0.2×0.2×0.2 mm3, F (000)=392.
The fnal R1 value is 0.030 (wR2 =0.076) for 1954 refections
[I>2σ(I)]. Flack structure parameter:−0.01 (6).
Acknowledgements We are grateful to Lanxiang Dai for the collection
of Angelica dahurica roots and Prof. Lin Yang at Lanzhou University
of Technology for the authentication of the plant material. This work
was fnancially supported by National Natural Science Foundation
of China (no. 21702178), Key Scientifc Research Program in Uni-
versities of Henan Province (no. 18A350010), Undergraduate Train-
ing Program for Innovation and Entrepreneurship of Henan Province
(nos. 201910480011, 201910480017), Science and Technology Project
of Henan Province (no. 182102311108), and Excellent Young Key
Teacher Funding Project of Xuchang University (no. 2017).
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