全 文 ： 药学学报 Acta Pharmaceutica Sinica 2015, 50 (3): 337−339 · 337 ·




A new aurone glycoside from Veratrum dahuricum (Turcz.) Loes. f.
GUO Jing-gong1, CHEN Yin-sheng2, LI Jing2, WANG Tian-xiao2, LI Sha-sha2, CONG Yue2*
(Henan University 1. School of Life Science, 2. Institute of Pharmacy, Pharmaceutical College, Kaifeng 475004, China)
Abstract: To study the chemical constituents of Veratrum dahuricum (Turcz.) Loes. f., a new aurone
glycoside named as (Z)-7, 4-dimethoxy-6-hydroxyl-aurone-4-O-β-glucopyranoside was isolated from the 95%
ethanol extracts of the rhizomes and roots of Veratrum dahuricum (Turcz.) Loes. f. by repeated column
chromatography on silica gel and recrystallization. Its structure was established by extensive spectroscopic
analyses, and its cytotoxicities against HepG-2, MCF7 and A549 cell lines were measured in vitro.
Key words: Veratrum dahuricum; aurone glycoside; (Z)-7, 4-dimethoxy-6-hydroxyl-aurone-4-O-β-
glucopyranoside; cytotoxicity
CLC number: R284 Document code: A Article ID: 0513-4870 (2015) 03-0337-03
兴安藜芦中一个新橙酮苷
郭敬功 1, 陈寅生 2, 李 静 2, 王天晓 2, 李沙沙 2, 丛 悦 2*
(河南大学 1. 生命科学学院, 2. 药学院药物研究所, 河南 开封 475004)

摘要: 本文对兴安藜芦 [Veratrum dahuricum (Turcz.) Loes. f.] 根和根茎的化学成分进行了研究。利用反复硅
胶柱色谱和重结晶方法从其 95% 乙醇提取物中分离得到一个新橙酮苷类化合物, 通过各种波谱 (MS、NMR和 UV)
分析方法确定其结构为 (Z)-7, 4-二甲氧基-6-羟基-橙酮-4-O-β-吡喃葡萄糖苷 ( (Z)-7, 4-dimethoxy-6-hydroxyl- au-
rone-4-O-β-glucopyranoside)。测试了该化合物在体外对人肝癌细胞株 HepG-2、人乳腺癌细胞株MCF7和人肺腺癌
细胞株 A549的细胞毒作用。
关键词: 兴安藜芦; 橙酮苷; (Z)-7, 4-二甲氧基-6-羟基-橙酮-4-O-β-吡喃葡萄糖苷; 细胞毒作用

Veratrum dahuricum (Turcz.) Loes. f., the important
species of the genus Veratrum, and its folk name is
Xingan Lilu in Chinese. Veratrum dahuricum (Turcz.)
Loes. f. distributes mainly in Liaoning, Jilin, Heilongjiang,
Neimonggu, and Xinjiang provinces in China. It was
originally used as emetic prescription for treatment of
hypertension, inflammation of throat disease, excessive
phlegm, epilepsy, etc. Modern pharmacological studies
have demonstrated that Veratrum dahuricum (Turcz.)
Loes. f. possesses antifungus, antihypertension, antiplatelet

Received 2014-09-29; Accepted 2014-10-28.
Project supported by the National Natural Science Foundation of China
(21102035); Natural Science Item of Education
Department of Henan Province (14A180030).
*Corresponding author Tel / Fax: 86-371-3880680,
E-mail: congyue1027@163.com
aggregation, antitumor, and inhibition of multidrug
resistance[1−4]. Extensive chemical studies of this plant
led to the isolation of steroidal alkaloids, flavonoids,
dipeptides, and so on[5]. In this paper, we report
the structure elucidation of a new aurone glycoside,
named as (Z)-7, 4-dimethoxy-6-hydroxyl-aurone-4-O-
β-glucopyranoside, which was isolated from the 95%
ethanol extract of Veratrum dahuricum (Turcz.) Loes. f.
(Figure 1), as well as the cytotoxicities of the compound
against human tumor cell lines of HepG-2, MCF7 and
A549 cells.

Results and discussion
Compound 1 was obtained as a orange-red amorphous
powder. The molecular formula C23H24O11 was
· 338 · 药学学报 Acta Pharmaceutica Sinica 2015, 50 (3): 337−339


Figure 1 The structure of compound 1

deduced from HR-ESI-MS (positive) m/z : 477.139 4
[M+H]+ (calcd. for C23H25O11, 477.139 7), 499.121 3
[M+Na]+ (calcd. for C23H24O11Na, 499.121 6), which
was supported by the 13C NMR spectrum data. The
1H NMR spectrum (Table 1) of compound 1 exhibited
two OMe signals at δ 3.80 (3H, s, H-1) and 3.58 (3H, s,
H-2), six signals of olefinic H-atoms at δ 5.81 (1H, s,
H-5), 7.77 (2H, d, J = 8.8 Hz, H-2, 6), 7.02 (2H, d, J =
8.8 Hz, H-3, 5), and 6.30 (1H, s, H-10), and signals of
one glucose group at δ 4.89 (1H, d, J = 7.6 Hz, H-Glc-1),
3.25 (1H, m, H-Glc-2), 3.31 (1H, m, H-Glc-3), 3.16
(1H, t, J = 8.8 Hz, H-Glc-4), 3.28 (1H, m, H-Glc-5),
3.70 (1H, d, J = 11.2 Hz, H-Glc-6), and 3.49 (1H, dd,
J = 11.2, 5.2 Hz, H-Glc-6). By analyses of the 1H,
13C NMR and 2D NMR (HMBC, HSQC, NOESY)
spectra of 1, it was revealed that 1 should be an aurone
glucoside[6, 7]. The 13C NMR spectrum displayed 23
carbon signals, including fourteen olefinic C-atoms,
one carbonyl C-atom, two methoxy C-atoms and six
O-substituted C-atoms. The HMBC correlations were
observed between δ 3.58 (H-2) and δ 136.3 (C-7), δ
3.80 (H-1) and δ 159.3 (C-4), δ 5.81 (H-5) and δ 161.7
(C-6), 107.3 (C-9), 157.1 (C-4), 136.3 (C-7), δ 6.30
(H-10) and δ 148.8 (C-2), 131.6 (C-2, 6), 180.7 (C-3),
δ 7.02 (H-3, 5) and δ 125.9 (C-1), 131.6 (C-2, 6),
159.3 (C-4), δ 7.77 (H-2, 6) and δ 159.3 (C-4), 125.9
(C-1), 114.4 (C-3, 5), 104.8 (C-10), suggesting that
the structure of its aglycone was elucidated as 7, 4-
dimethoxy-4, 6-dihydroxyl-aurone by analysis of HMBC
and HSQC spectra. The β configuration of glucose
was substantiated by the coupling constant of the
anomeric proton δ 4.89 (1H, d, J = 7.6 Hz, H-Glc-1).
The position of the sugar was confirmed by the HMBC
spectrum (Figure 2), which showed a correlation
between δ 4.89 (1H, d, J = 7.6 Hz, H-Glc-1) and δ
157.1 (C-4), indicating the glucose group was attached
to C-4. These assignments were further confirmed
by the NOESY spectrum which showed correlations
between δ 6.30 (H-10) and δ 7.77 (2H, d, J = 8.8 Hz,
H-2, 6), δ 5.81 (1H, s, H-5) and δ 4.89 (1H, d, J = 7.6
Hz, H-Glc-1). The Z-stereochemistry of the double
bond at C-10 in 1 was determined by the chemical shift
of C-10 (δ 104.8)[8]. Based on these data, the structure
of compound 1 was identified, and named as (Z)-7, 4-
dimethoxy-6-hydroxyl-aurone-4-O-β-glucopyranoside.

Table 1 1H NMR (400 MHz) and 13C NMR (100 MHz) data
for compound 1 (in DMSO-d6)
No. δH δc
2 148.8
3 180.7
4 157.1
5 5.81 (s) 80.9
6 161.7
7 136.3
8 167.6
9 107.3
10 6.30 (s) 104.8
1 125.9
2 7.77 (d, J = 8.8 Hz) 131.6
3 7.02 (d, J = 8.8 Hz) 114.4
4 159.3
5 7.02 (d, J = 8.8 Hz) 114.4
6 7.77 (d, J = 8.8 Hz) 131.6
1 3.80 (s) 55.2
2 3.58 (s) 59.2
Glc-1 4.89 (d, J = 7.6 Hz) 100.2
Glc-2 3.25 (m) 73.5
Glc-3 3.31 (m) 77.1
Glc-4 3.16 (t, J = 8.8 Hz) 69.7
Glc-5 3.28 (m) 76.8
Glc-6 3.70 (d, J = 11.2 Hz) 60.8
3.49 (dd, J = 11.2, 5.2 Hz)


Figure 2 Key HMBC correlations of compound 1

Experimental
General experimental procedures UV data was
determined by UV-VIS spectrophotometer (Shimadzu,
Japan). NMR Spectra was recorded by Bruker ARX-
400 spectrometer in DMSO-d6 with TMS as an internal
standard. The chemical shifts were quoted relative
to TMS and the coupling constants were in Hz. HR-
ESI-MS data were obtained on a MDS Sciex ESI-Q-
TOF mass spectrometer. Column chromatography
was performed on silica gel G (SiO2; 200−300 mesh,
GUO Jing-gong, et al: A new aurone glycoside from Veratrum dahuricum (Turcz.) Loes. f. · 339 ·

Qingdao Marine Chemical Factory, P. R. China). TLC
was carried out on precoated silica gel GF-254 plates
(Merck, Germany), and spots were detected with 10%
H2SO4 in alcohol followed by heating. The reagents
were analytical grade.
Plant material The rhizomes and roots of
Veratrum dahuricum (Turcz.) Loes. f. were collected in
July 2008 at Liaoning province, China and authenticated
by Assoc. Prof. Wangjun Yuan from Henan University.
The voucher specimen was deposited at the Institute of
Pharmacy, Pharmaceutical College, Henan University.
Extraction and isolation The air-dried rhizomes
and roots of Veratrum dahuricum (Turcz.) Loes. f. (10
kg) was extracted with 5-fold 95% EtOH under reflux
for 3 times. The extract was concentrated under
reduced pressure to yield a residue (387 g), which was
subjected to CC (SiO2; CH2Cl2/MeOH 100∶1 to 0∶
100) to yield 15 combined fractions. Fr. 6 (0.8 g) was
further subjected to CC (SiO2; petroleum ether/Me2CO
1∶1) to yield combined Frs. A−D. Frs. D (0.1 g) was
further subjected to CC (SiO2; CH2Cl2/MeOH 10∶1 to
0∶10) and followed by recrystallization in MeOH to
afford 1 (11 mg).
(Z)-7, 4-dimethoxy-6-hydroxyl-aurone-4-O-β-
glucopyranoside (1) Orange-red amorphous powder;
UV (MeOH) λmax (log ε) 257 (3.8), 328 (4.6) (nm);
1H and 13C NMR spectral data see Table 1. ESI-MS
(positive) m/z 499.1 [M+Na]+, 477.1 [M+H]+; HR-ESI-
MS (positive) m/z: 477.139 4 [M+H]+ (calcd. for
C23H25O11, 477.139 7), 499.121 3 [M+Na]+ (calcd. for
C23H24O11Na, 499.121 6).
Cytotoxic assay The in vitro cytotoxicity assay
of compound 1 was evaluated by the MTT method
using the HepG-2, MCF7, and A549 cell lines as
previously described[9]. Compound 1 exhibited no
cytotoxicities against HepG-2, MCF7 and A549 cell
lines with the IC50 value of 121.9, 110.5 and 146.3
μmol·L−1, respectively.
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