全 文 ： 2009 年 7 月 第 7 卷 第 4 期 Chin J Nat Med July 2009 Vol. 7 No. 4 283








Anti-tumor Constituents from Scorzonera mongolica

WANG Bin1*, QIU Pei-Ju2, LI Guo-Qiang2, QU You-Le1
1School of Food and Pharmacy, Zhejiang Ocean University, Zhoushan 316000;
2School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
[ABSTRACT] AIM: To study the anti-tumor active constituents of Scorzonera mongolica Maxim.. METHOD: The
chemical components were isolated by silica gel, Sephadex LH-20 column chromatography and semi-preparative HPLC.
Structures were elucidated on the basis of physicochemical and spectral data. The anti-tumor experiment in vitro, the
MTT, was used to screen the constituents of S. mongolica Maxim.. RESULTS: 12 chemical components were isolated
and identified as dehydrocostus lactone (1), β-sitosterol (2), cholesterol (3), 5α, 8α-epidioxy-(22E, 24R)-ergosta- 6, 22-
dien-3β-ol (4), glycerol -1-octadecanoate (5), 1-linoloyglycerol (6), stearic acid (7), palmitic acid (8), sucrose (9), luteo-
lin-5, 3′-dimethyl ether (10), diisobutyl-O-phthalate (11) and dibutyl-O-phthalate (12) respectively. CONCLUSION:
Chemical components 1-12 were obtained from the plant for the first time. Compounds 1, 4 and 10 showed cytotoxicity
against human lung cancer A-549 cells at the concentration of 50µg·mL-1.
[KEY WORDS] Scorzonera mongolica Maxim.; Chemical constituents; Anti-tumor activity
[CLC Number] R284 [Document code] A [Article ID] 1672-3651(2009)04-0283-04
doi: 10.3724/SP. J. 1009.2009.00283
1 Introduction
Scorzonera mongolica Maxim. belongs to the large
family of Compositae and is mainly distributed in the north
and northwestern regions of China [1]. The roots have been
used as traditional medicines for the treatment of fever,
carbuncle mastitis and cancers. However, no chemical re-
search previous on the species has been recorded, and only
a few articles on other members of the genus have revealed
the presence of sesquiterpenoids, triterpenoids, steroids,
flavonoids, tyrolobibenzyls and dihydroisocoumarins [2-8].
In the continuing research on the bioactive components, the
chemical constituents of S. mongolica were studied system-
atically and two new moradiol triterpene fatty esters have
already been reported [9]. Our detailed investigation has led
to the discovery of 12 known compounds from the metha-
nol extract of the plant. These compounds were identified
as dehydrocostus lactone (1), β-sitosterol (2), cholesterol
(3), 5α, 8α-epidioxy-(22E, 24R)-ergosta-6, 22-dien-3β-ol
(4), glycerol-1-octadeca- noate (5), monoolein (6), stearic
acid (7), palmitic acid (8), sucrose (9), luteolin-5,

[Received on] 18-May-2008
[Foundation Item] This project was supported by National High
Technology 863 Project (No.2007AA091701), Zhejiang Provincial
Natural Science Foundation (No.Y2080579) and Important Project
of Zhejiang Ocean University (No.21135030107).
[*Corresponding author] WANG Bin: instructor, Tel:
86-580-2555005, Fax: 86-580-2554781, E-mail: bin-
wang4159@hotmail.com
3′-dimethyl ether (10), diisobutyl-O-phthalate (11) and
dibutyl-O-phthalate (12). Some of these compounds showed
potent cytotoxicity against human cancer cell lines. In this
paper, the isolation, structural elucidation and cytotoxicity
of the isolated compounds are described.
2 Experimental
2.1 General
Optical rotations were obtained on a Jasco P-1020
digital polarimeter. IR spectra were taken on a Nicolet
NEXUS 470 spectrophotometer in KBr disks. 1H, 13C NMR,
DEPT and 2D NMR spectra were recorded on a JEOL
JNM-ECP-600 spectrometer using TMS as internal standard,
and chemical shifts were recorded as δ values. NOESY
experiments were carried out using a mixing time of 0.5 s.
1D NOE spectra were obtained on a Varian INOVA-400
spectrometer. HR-SIMS was measured on a Bruker Apex II
FT ion cyclotron resonance mass spectrometer and ESIMS
were recorded in Q-STAR ESI-TOFMS/MS mass spec-
trometer. Column chromatography was carried with silica
gel (200-300 mesh), and GF254 silica gel for TLC was pro-
vided by Qingdao Marine Chemical Co. Higher pressure
liquid chromatography (HPLC) was performed on an All-
tech 426 apparatus using Kromasil prepack column (ODS,
10 mm×250 mm, for reverse phase) and monitored by UV
detector.
2.2 Plant Material
The original plant S. mongolica was collected in
Dongying, north of Shandong Province, China, in October,
WANG Bin, et al. /Chinese Journal of Natural Medicines 2009, 7(4): 283−286
284 Chin J Nat Med July 2009 Vol. 7 No.4 2009 年 7 月 第 7 卷 第 4 期

2005, and authenticated by Prof. Zhou Feng-qin, College of
Traditional Chinese Medicine, Shandong University of
Traditional Chinese Medicine. Voucher specimen was de-
posited in the Key Laboratory of Marine Drugs, Chinese
Ministry of Education, School of Medicine and Pharmacy,
Ocean University of China under reference DY0510015.
2.3 Extraction and Isolation
Air-dried plant (1.2 kg) was pulverized and extracted
with methanol three times (7 days each time) at room tem-
perature. The solvent, filtrated and evaporated under re-
duced pressure to dryness, gave 100 g of a brown gummy
residue, of which 90 g were chromatographed on silica gel
column chromatographer, eluted with increasing polarity
from petroleum ether to acetone to afford 4 fractions (A-D).
Fraction A (1.4 g) was further subjected to silica gel CC
with petroleum ether-acetone (25:1) and Sephadex LH-20
with petroleum ether-chloroform-methanol (5:5:1) to yield
compounds 2 (350.7mg) and 3(15.7mg); Fraction B (3.9 g)
was further subjected to silica gel CC with petroleum
ether-acetone (25:1), Sephadex LH-20 with petroleum eth-
er-chloroform -methanol (5:5:1) and semi-preparative
HPLC employing isocratic elution with methanol to give
compounds 1 (6.6mg) and 4 (19.3mg); Fraction C (3.5 g)
was subjected to silica gel CC with a gradient of petroleum
ether–acetone (15:1→10:1) and semi-preparative HPLC
employing isocratic elution with methanol to give com-
pounds 5 (7.6mg), 6 (8.5mg), 7 (9.7mg) and 8 (7.4mg);
Fraction D (25.3 g) was purified by petroleum eth-
er–acetone (10:1→1:1), Sephadex LH-20 with petroleum
ether-trichloromethane-methanol (3:3:1) and semi-prepara-
tive HPLC employing isocratic elution with methanol-H2O
(98:2, 1.5 mL·min−1) to give compounds 9 (11.3 mg), 10
(9.6 mg), 11 (12.1 mg) and 12 (10.2 mg).
2.4 Biological assays
Cytotoxic activity was evaluated using P-388 cell line
by the MTT method and the A-549 cell line by the SRB
method.
In the MTT assay, the cell line was grown in
RPMI-1640 supplemented with 10% FBS under a humidi-
fied atmosphere of 5% CO2 and 95% air at 37°C. Cell sus-
pensions (200 µL) at a density of 5 × 104 cells/mL were
plated in 96-well microtiter plates and incubated for 24 h.
The tested compound solutions (2 µL in MeOH) at different
concentrations were added to each well and further incu-
bated for 72 h under the same conditions. MTT solution (20
µL of a 5 mg·mL-1 solution in IPMI-1640 medium) was
added to each well and incubated for 4 h. Old medium (150
µL) containing MTT was gently replaced by DMSO and
pipetted to dissolve any formazan crystals formed. Absorb-
ance was then determined on a Spectra Max Plus plate
reader at 540 nm.
In the SRB assay, cell suspensions (200 µL) were
plated in 96-well plates at a density of 2 × 10 5 cells/mL.
Then the tested compound solutions (2 µL in MeOH) at the
concentration of 50 µg·mL−1 were added to each well and
further incubated for 24 h. Following drug exposure, the
cells were fixed with 12% trichloroacetic acid and the cell
layer was stained with 0.4% SRB. The absorbance of SRB
solution was measured at 515 nm.
Inhibition rate (%) = ((Acontrol - Asample)/ Acontrol) ×
100%
Where the Acontrol is the absorbance of the control, the
Asample is the absorbance of the test sample.
3 Results and Discussion
3.1 Structural identification
Dehydrocostus lactone [9] (1) White powder
(CHCl3), mp 60-61.5 °C, gave light pink coloration upon
treatment with vanillin-sulphuric acid on a TLC plate fol-
lowed by heating. 1H NMR (600 MHz, CDCl3) δH: 1.94 (1H,
m, H-1), 1.88 (1H, m, H-2a), 2.53 (2H, m, H-2b), 2.87 (1H,
m, H-4), 3.97 (1H, t, J = 9.1Hz, H-5), 2.87 (1H, m, H-6),
2.48 (1H, m, H-8a), 2.16 (1H, m, H-8b), 2.92 (1H, m, H-10),
6.22 (1H, d, J = 3.7 Hz, H-13a), 5.50 (1H, d, J = 3.7 Hz,
H-13b), 4.90 (1H, brd, H-14a), 4.86 (1H, brd, H-14b), 5.27
(1H, dd, J = 4.6 Hz, 1.7Hz, H-15a), 5.07 (1H, dd, J = 4.6,
1.7 Hz, H-15b). 13C NMR (150 MHz, CDCl3) δC: 30.3 (C-1),
32.6 (C-2), 151.2 (C-3), 52.0 (C-4), 85.3 (C-5), 45.1 (C-6),
30.9 (C-7), 36.3 (C-8), 149.2 (C-9), 47.6 (C-10), 139.7
(C-11), 170.3 (C-12), 120.2 (C-13), 112.6 (C-14), 109.6
(C-15).
β-sitosterol [10] (2) Colorless needles crystal
(CHCl3), gave purple coloration upon treatment with vanil-
lin-sulphuric acid on a TLC plate followed by heating. 1H
NMR(600 MHz, CDCl3) δH: 5.35 (1 H, d, J = 2.8 Hz, H-6),
3.53 (1 H, m, H-3), 0.68 (3 H, s, CH3-18), 0.84 (3H, d, J =
6.9 Hz, CH3-29), 0.86 (3H, s, CH3-26), 0.87 (3H, s,
CH3-27), 0.92 (3H, d, J = 6.4 Hz, CH3-21), 1.01(3H, s,
CH3-19). 13C NMR (150 MHz, CDCI3) δC: 36.6(C-1), 29.7
(C-2), 71.8 (C-3), 47.90 (C-4), 140.8 (C-5), 121.7 (C-6),
31.7 (C-7), 32.0 (C-8), 50.3 (C-9), 36.2 (C-10), 28.3 (C-11),
39.9 (C-12), 42.4 (C-13), 56.9 (C-14), 26.3 (C-15), 29.3
(C-16), 56.2 (C-17), 11.9 (C-18), 19.8 (C-19), 32.0 (C-20),
19.4 (C-21), 34.1 (C-22), 24.3 (C-23), 37.3 (C-24), 19.1
(C-25), 12.0 (C-26), 23.2 (C-27), 21.1 (C-28), 18.8 (C-29).
Cholesterol [11] (3) White powder (MeOH), gave
purple coloration upon treatment with vanillin-sulphuric
acid on a TLC plate followed by heating. 1H NMR (600
MHz, CDCl3) δH: 0.69 (3H, s, CH3-18), 1.01 (3H, s,
CH3-19), 0.92 (3H, d, J = 6.2 Hz, CH3-21), 0.87 (3H, d, J =
6.6 Hz, CH3-26 or 27) and 0.86 (3H, d, J = 6.2 Hz, CH3-26
or 27), 3.52 (1H, m, H-3), 5.35(1H, d, J = 2.8Hz, H-6).
5α, 8α-epidioxy-(22E, 24R)-ergosta-6, 22-dien-3β-
ol [12] (4) White powder (MeOH), gave purple blue col-
oration upon treatment with vanillin-sulphuric acid on a
TLC plate followed by heating. 1H NMR(600 MHz, CDCl3)
δH: 0.81 (3H, d, J = 6.4, CH3-27), 0.83 (3H, s, CH3-18),
WANG Bin, et al. /Chinese Journal of Natural Medicines 2009, 7(4): 283−286
2009 年 7 月 第 7 卷 第 4 期 Chin J Nat Med July 2009 Vol. 7 No. 4 285

0.84 (3H, d, J = 6.4, CH3-26), 0.88 (3H, s, CH3-19), 0.91
(3H, d, J = 6.6, CH3-28), 1.00 (3H, d, J = 6.6, CH3-21),
3.96 (1H, m, H-3), 5.15 (1H, dd, J = 15.3, 7.2 Hz, H-22),
5.23 (1H, dd, J = 15.3, 7.2 Hz, H-23), 6.23 (1H, d, J = 8.3
Hz, H-22a), 6.49 (1H, d, J = 8.3 Hz, H-22b). 13C NMR
(150Hz, CDCl3) δC: 34.6 (C-1), 29.9 (C-2), 66.2 (C-3), 36.9
(C-4), 82.2 (C-5), 135.4 (C-6), 130.6 (C-7), 79.4 (C-8), 51.0
(C-9), 36.8 (C-l0), 23.3 (C-11), 39.7 (C-l2), 44.5 (C-13),
51.6 (C-l4), 20.8 (C-l5), 28.6 (C-l6), 56.1 (C-17), 12.8
(C-18), 18.1 (C-l9), 39.7 (C-20), 20.5 (C-21), 135.1 (C-22),
132.2 (C-23), 42.7 (C-24), 33.0 (C-25), 20.8 (C-26), 19.7
(C-27), 17.6 (C-28).
Glycerol-1-octadecanoate [13] (5) White powder
(CHCl3), mp 76-78 °C, gave blue coloration upon treatment
with vanillin-sulphuric acid on a TLC plate followed by
heating. ESI-MS m/z: 381[M+Na ]+, 1H NMR(600 MHz,
CDCl3) δH: 4.18 (2H, dd, J = 11.6, 4.8 Hz, H-1), 3.96 (1H,
m, H-2), 3.76 (1H, d, J = 9.6 Hz, OH-2), 3.70 (1H, dd, J =
11.4, 4.5 Hz, H-3), 3.62 (1H, dd, J = 11.4, 5.7 Hz, H-3),
2.35 (2H, t, J = 7.5 Hz, H-2′), 1.62 (2H, t, J = 7.2 Hz, H-3′),
1.24 (28H, m, H-4′ ~ 17′), 0.89 (3H, t, J = 6.5 Hz, H-18′).
Monoolein [14, 15] (6) White oil, mp 67 ~ 69 °C, gave
blue coloration upon treatment with vanillin-sulphuric acid
on a TLC plate followed by heating. ESI-MS (m/z):
377[M+Na]+. 1H NMR (600 MHz, CDCl3) δH: 4.20 (1H,
dd, J = 4.6, 10.2 Hz, H-1α), 4.17 (1H, dd, J = 10.8, 6.4 Hz,
H-1β), 3.90 (1H, m, H-2), 3.63 (1H, dd, J = 4.7, 11.2Hz,
H-3a), 3.56 (1H, dd, J = 5.2, 11.4Hz, H-3b), 2.75 (2H, t, J =
6.5Hz, H-11′), 2.34 (2H, t, J = 7.2Hz, H-1′), 1.61 (2H, m,
H-2′), 5.33 (4H, m, H-9′, 10′, 12′, 13′), 0.84 (3H, t, J = 6.8
Hz, H-18′).
Stearic acid [16] (7) white waxy substance, EI-MS
m/z: 284[M]+, 256, 213, 185, 129, 73. 1H NMR (600 MHz,
CDCl3) δH: 0.88 (3H, t, J = 6.8 Hz, H-18), 1.25 (m, H-4 ~
17), 1.63 (2H, m, H-2), 2.34 (2H, m, H-3).
Palmitic acid [16] (8) White particle crystal, mp 60 ~
62 °C. EI-MS m/z: 256 [M]+, 241, 227, 213, 199, 115, 73.
1H NMR (600 MHz, CDCl3) δH: 0.88 (3H, t, J = 6.8 Hz,
H-16), 1.25(m, H-4 ~ 15), 1.63 (2H, m, H-2), 2.34 (2H, m,
H-3).
Sucrose [17, 18] (9) White square crystal, 1H NMR
(600 MHz, DMSO-d6) δH: 5.20 (1H, d, J = 3.4 Hz, OH),
5.18 (1H, d, J = 5.2 Hz, fru-H-2), 5.02 (1H, d, J = 5.8 Hz,
OH), 4.79 (1H, d, J = 5.8 Hz, OH), 4.75 (1H, d, J = 4.9 Hz,
OH), 4.76 (1H, dd, J =1.0, 5.4 Hz, OH), 4.49 (1H, d, J = 7.8
Hz, glc-H-1), 4.40 (1H, td, J = 1.5, 4.7 Hz, fru-Hb-1), 4.35
(1H, dt, J = 1.5, 4.7 Hz, fru-Ha-1), 3.84 (1H, t, J = 7.9 Hz,
fru-Ha-6), 3.76 (1H, dd, J = 7.0, 11.8 Hz, glc-Ha-6), 3.63
(1H, dd, J = 1.5, 11.9 Hz, lc-Hb-6), 3.60 (1H, dd, J = 2.6,
7.9 Hz, fru-Hb-6), 3.52 (2H, m, fru-H-3, fru-H-4 ), 3.49
(1H, m, glc-H-3), 3.45 (1H, m, glc-H-4), 3.38 (1H, d, J =
6.4 Hz, fru-H-5), 3.17 (1H, m, glc-H-5), 3.13 (1H, m,
glc-H-2).

Luteolin-5, 3′-dimethyl ether [19] (10) Yellow pow-
der (MeOH); EI-MS: m/z 314 [M]+, 285, 268, 148, 137. 1H
NMR (600 MHz, DMSO-d6) δH: 11.0 (1H, brs, -OH), 9.85
( 1H, brs, -OH), 7.52 (1H, s, H-2′), 7.47 (1H, d, J = 7.5 Hz,
H-6′), 6.91 (1H, d, J = 7.5 Hz, H-5), 6.60 (1H, s, H-3),
6.55(1H, d, J = 1.8 Hz, H-8), 6.36 (1H, d, J = 1.8 Hz, H-6),
3.88 (3H, s, -OMe ), 3.80 (3H, s, -OMe ).
Diisobutyl-O-phthalate [20] (11) White oil, 1H NMR
(600 MHz, CDCl3) δH: 7.57 (1H, d, J = 7.1 Hz, H-2), 7.56
(1H, d, J = 9.0 Hz, H-5), 7.75 (2H, dd, J = 7.6, 7.6 Hz, H-3,
H-4), 4.11 (4H, d, J = 5.7 Hz, H-1, H-9), 2.06 (2H, m,
H-2, 2), 1.01 (12H, d, J = 6.7 Hz, 4 × CH3).
Dibutyl-O-phthalate [21] (12) White oil, mp 213 ~
215°C. 1H NMR (600 MHz, CDCl3) δH: 7.75 (2H, br, J =
6.7 Hz, H-3, 6), 7.55 (2H, m, H- 4, 5), 4.33 (2H, t, J = 7.0
Hz, H-1), 1.74 (4H, tt , J = 7.0 Hz, H-2), 1.47(4H, m, H-3),
0.98 (6H, t, J = 7.0 Hz, CH3-4).
3.2 Cytotoxicity test
Using the MTT and SRB dye reduction assays, the
cytotoxicity against P-388 and A549 of purified compounds
were tested at the concentration of 50µg·mL-1. The inhibi-
tion rate (%) of the compounds on each cell lines is pre-
sented in Table 1. The results indicated that compounds 1, 4
and 10 showed moderate cytotoxicity on A-549 cell line.

Table 1 Effects of compounds on two tumor cell lines at
the concentration of 50 µg·mL−1
Inhibitory rate (%)
No. c µg•mL−1 P-388 A-549
1 50 13.6 69.8
4 50 21.1 66.8
5 50 25.8 8.3
6 50 27.9 11.4
10 50 33.7 72.4

4 Conclusion
By bioassay-guided isolation, the constituents of S.
mongolica were systematically investigated and 12 com-
pounds were obtained. Some compounds showed potential
anti-tumor activities, but all the results in this study came
from short-term experiments, so further investigations will
involve the mechanism of constituents responsible for their
cytotoxicity. Our data may contribute to a rational basis on
the use of S. mongolica for cancer treatment, and the find-
ings of the current report seem to be useful for further re-
search aiming to utilize the plant as a source of antitumor
food or pharmaceutical products.
Acknowledgements
The authors are grateful for Prof. ZHOU Feng-qin for
the species identification of S. mongolica and Professor
GENG Mei-yu for the cytotoxicity assays.
WANG Bin, et al. /Chinese Journal of Natural Medicines 2009, 7(4): 283−286
286 Chin J Nat Med July 2009 Vol. 7 No.4 2009 年 7 月 第 7 卷 第 4 期

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蒙古鸦葱抗肿瘤活性成分
王 斌 1*, 邱培菊 2, 李国强 2, 曲有乐 1
1 浙江海洋学院食品与药学学院, 舟山 316004;
2 中国海洋大学医药学院, 青岛 266003
【摘 要】 目的：系统研究蒙古鸦葱的抗肿瘤活性成分。方法：使用硅胶、Sephadex LH-20、ODS 和 HPLC 分离、
纯化, 根据理化性质和光谱分析鉴定化合物的结构。采用MTT法和 SRB法进行活性跟踪和单体化合物的抗肿瘤活性筛选。
结果：分离鉴定了 12 个化合物, 分别为脱氢木香内酯(1)、β-谷甾醇(2)、胆甾醇(3)、5α, 8α-环二氧-24-甲基胆甾-6, 22-二
烯-3β-醇(4)、硬脂酸-1-甘油单脂(5)、1-亚油酸甘油酯(6)、硬脂酸(7)、软脂酸(8)、蔗糖(9)、毛地黄黄酮-5, 3′-二甲酯(10)、
邻苯二甲酸二异丁酯(11)和邻苯二甲酸二正丁酯(12)。结论：1~12 均为首次从蒙古鸦葱中分离得到。药理实验表明, 化合
物 1, 4 和 10 在 50 µg·mL−1浓度下对小鼠肺腺癌细胞 A-549 显示出一定的抑制作用。
【关键词】 蒙古鸦葱; 化学成分; 抗肿瘤活性

【基金项目】 863 重点项目(2007AA091701)、浙江省自然科学基金(Y2080579)和浙江海洋学院重大项目(21135030107)。