全 文 ： 20 Chin J Nat Med Jan. 2012 Vol. 10 No. 1 2012 年 1 月 第 10 卷 第 1 期

Chinese Journal of Natural Medicines 2012, 10(1): 0020−0023
doi: 10.3724/SP.J.1009.2012.00020
Chinese
Journal of
Natural
Medicines







A new phenylpropanoid glycoside from the
fruits of Illicium simonsii
WEI Dan-Dan, WANG Jun-Song*, ZHANG Yao, KONG Ling-Yi
Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
Available online 20 Jan. 2012
[ABSTRACT] AIM: To study the constituents and bioactivity of Illicium simonsii. METHODS: The extracts of the fruits of Illicium
simonsii were submitted to a combination of chromatographic materials, silica gel, ODS column chromatography and finally prepara-
tive HPLC to obtain eight compounds which were further evaluated for their cytotoxicity by MTT method. RESULTS: A new phenyl-
propanoid glycolside, 2, 4-dihydroxy-allylbenzene-2-O-β-D-glucopyranoside (1), together with seven characteristic sesquiterpene lactones,
oligandrumin B (2), oligandrumin D (3), anisatin (4), veranisatin D (5), pseudomajucin (6), 1α-hydroxy-3-deoxy-pseudoanisatin (7), 8α-hy-
droxy-10-deoxycyclomerrillianolide (8) were isolated. CONCLUSION: Compound 1 is new. Compounds 1, 2, 3, 5−8 were isolated from
this plant for the first time. None of the isolates showed inhibitory effects on the growth of non-small cell lung tumor cell line A549.
[KEY WORDS] Illicium simonsii; Phenyl propanoid glycoside; Sesquiterpene lactones; Cytotoxicity
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2012)01-0020-04

[Received on] 19-Mar.-2011
[Research funding] This project was supported by the National
Natural Science Foundation of China (No. 30801514).
[*Corresponding author] WANG Jun-Song: Associate Prof., Tel.:
86-25-83271402, Fax: 86-25-85301528, E-mail: wang.junsong@gmail.com
These authors have no any conflict of interest to declare.
(Fig. 1), together with their cytotoxic evaluation on these
isolates.
2 Experimental
2.1 General experimental procedures
Sephadex LH-20 (Pharmacia, USA), Rp-C18

(40−63 μm,
FuJi, Japan) and silica gel (45−75 μm, Qingdao Marine
Chemical Co. Ltd., China) were used. Optical rotations were
determined with a JASCO P-1020 polarimeter (Na filter, λ =
589 nm). IR spectra were recorded on a Bruker Tensor 27
spectrometer with KBr-disks. Preparative HPLC was carried
out using Agilent 1100 Series with a Shimpack Rp-C18

col-
umn (20 mm × 200 mm, i.d.). Mass spectra were obtained on
a MS Agilent 1100 Series LC/MSD Trap mass spectrometer
(ESI-MS) and HRESI-MS was done on a Mariner time-of-
flight mass spectrometer with an electrospray interface, re-
spectively. NMR spectra were recorded on Bruker AVANCE
III-500 NMR (1H: 500 MHz, 13C: 125 MHz) and Bruker
ACF-300 NMR instrument (1H: 300 MHz, 13C: 75 MHz)
instrument.
2.2 Plant material
The fruits of I. simonsii were collected from Kunming,
Yunnan Province in July 2009, and authenticated by Prof.
TAO De-Ding of Kunming Institute of Botany, Chinese
Academy of Science. A voucher specimen (No. IS200907) is
deposited in the Herbarium of Department of Natural Me-
dicinal Chemistry, China Pharmaceutical University.

1 Introduction
The genus Illicium (Illiciaceae), distributed mainly in the
southwestern and eastern parts of China[1] and the southeast
of Asia and America. It features sesquiterpenes, neolignans
and prenylated C6-C3 compounds with diverse skeletons[2-5].
The leaves and fruits of Illicium simonsii Maxim. are com-
monly used to cure gastro-frigid vomiting, cystic hernia, gas
pains in chest and scabies as folk medicine. The fruits and
stem barks contain highly oxygenated seco-prezizaane-type
sesquiterpenes[6], neolignans[7], rearranged prenylated C6-C3
compounds[8], flavones and anthraquinones[9]. Some ses-
quiterpene lactones from its fruits were found to exhibit high
neurotoxicity in mice[6] and 90% ethanol extract exhibited
activity against HIV in vitro[9]. In this paper, we reported the
isolation and structural elucidation of a new phenylpropanoid
glycoside, 2, 4-dihydroxy-allylbenzene-2-O-β-D-glucopy-
ranoside (1) and a series of known sesquiterpene lactones,
oligandrumin B (2), oligandrumin D (3), anisatin (4), verani-
satin D (5), pseudomajucin (6), 1α-hydroxy-3-deoxy- pseu-
doanisatin (7), 8α-hydroxy-10-deoxycyclomerrillianolide (8)

WEI Dan-Dan, et al. /Chinese Journal of Natural Medicines 2012, 10(1): 20−23
2012 年 1 月 第 10 卷 第 1 期 Chin J Nat Med Jan. 2012 Vol. 10 No. 1 21


Fig. 1 Structures of compounds 1-8
2.3 Extraction and isolation procedure
Air-dried fruits of the plant (10 kg) were powdered and
extracted with 95% ethanol. Concentrated under reduced
pressure, a total of 1.2 kg extract was obtained, which was
suspended in water and partitioned sequentially with petro-
leum ether (735 g), CH2Cl2 (125 g) and EtOAc (210 g).
The crude CH2Cl2 extract (125 g) was first chroma-
tographed on a column packed with silica gel (75−150 μm)
eluted with MeOH-CH2Cl2 to give five fractions F1-F5.
Fraction F2 (28 g) was chromatographed on silica gel
eluted with petroleum ether-EtOAc (5 : 1-1 : 3), then over
MCI with MeOH-H2O and finally purified by successive
preparative HPLC to give 2 (35 mg), 3 (30 mg), 4 (22 mg)
and 5 (28 mg). Fraction F3 (5.0 g) was subjected to a Si gel
column eluted with petroleum ether-EtOAc (5 : 1-1 : 2), puri-
fied by ODS and Sephadex LH-20 chromatography and pre-
parative HPLC to obtain 6 (18 mg), 7 (30 mg) and 8 (25 mg).
Fraction F4 (8.0 g) was subjected to a Si gel column eluted
with CH2Cl2-MeOH (1 : 0-5 : 1), purified by ODS and
Sephadex LH-20 (MeOH) chromatography and then sub-
jected to preparative HPLC to afford 1 (10.0 mg).
2.4 Hydrolysis of 2, 4-dihydroxy-allylbenzene-2-O-β-D-glu-
copyranoside (1)
The crude phenyl propanoid glycoside (40 mg) was re-
fluxed with 10 mL of 1 mol·L-1 H2SO4 in MeOH-H2O (1 : 1)
at 100 °C for 4 h. The acid aqueous layer was neutralised
with NH4OH followed by extraction with CHCl3. The sugar
was identified by comparison of the Rf value by TLC and
optical rotation with authentic samples[10-11].
3 Results and discussion
Compound 1 was isolated as a brown gum. Its molecular
formula was determined as C15H20O7 by HR-ESI-MS, indi-
cated by a pseudo-molecular ion at 335.109 8 [M + Na]+
(Calcd. for C15H20O7Na, 335.110 1), suggesting the presence
of 6 degrees of unsaturation. The IR spectrum showed two
strong absorption bands due to hydroxyl (3 397 cm-1) and
benzene ring (1 614 and 1 510 cm-1) groups. The 13C NMR
spectrum resolved 15 carbon resonances which were classi-
fied by the chemical shifts and the HSQC spectrum as four
double bonds at δ 158.0 (C-4), 157.5 (C-2), 139.4 (C-8),
131.4 (C-6), 122.0 (C-1), 115.1 (C-9), 110.3 (C-5) and 104.3
(C-3) and one hemiacetal carbon signal at δ 102.9 (C-1). The
1H NMR spectrum of 1 showed an ABX coupling system
composed of aromatic protons at δ 6.90 (1H, d, J = 8.0 Hz,
H-6), 6.64 (1H, d, J = 2.5 Hz, H-3), 6.39 (1H, dd, J = 8.0, 2.5
Hz, H-5), a characteristic allylic group [δ 5.97 (1H, ddt, J =
17.0, 10.5, 7.0 Hz, H-8), 5.00 (1H, dq, J = 17.5, 2.0 Hz,
H-9α), 4.94 (1H, ddt, J = 10.5, 2.0, 1.0 Hz, H-9β); 3.34 (2H,
d, J = 7.0 Hz, H-7, -CH2-)], indicated the presence of a 1, 3,
4-trisubstituted benzene ring moiety. The hemiacetal proton
at δ 4.83 (1H, d, J = 7.5 Hz, H-1) as well as its correlation
with the carbon signal at δ 102.9 (C-1) in the HSQC spec-
trum and five oxygenic carbon resonance at δ 78.5 (C-5),
78.3 (C-3), 75.2 (C-2), 71.5 (C-4), 62.8 (C-6) also revealed
the presence of a glucopyranose moiety. The β-anomeric
configuration for the glucopyranose was determined by a
large coupling constant (7.5 Hz) of the anomeric proton[12].
On acid hydrolysis, 1 afforded D-glucose, identified by
co-TLC analysis and by measurement of optical rotation
([α]21 D +25.5°)[10]. The analysis above indicated that compound
1 was a dihydroxyl substitued phenylpropanoid glycoside.
The location of allyl group was assigned to C-2 in ac-
cordance with the HMBC correlations between H-7 and C-1,
C-2 and C-6. Moreover, the HMBC correlation between H-1
and C-2 indicated that the glucopyranose moiety was at C-2.
The structure of 1 was thus elucidated as 2, 4-dihydroxy-
allylbenzene-2-O-β-D-glucopyranoside (Fig. 2). The 1H, 13C
NMR and HMBC data of 1 was listed in Table 1.
In addition, compounds 2−8 were identified to be oli-
gandrumin B[3], oligandrumin D[3], anisatin[13], veranisatin
D[3], pseudomajucin[14], 1α-hydroxy-3-deoxy-pseudo- ani-
satin[15] and 8α-hydroxy-10-deoxycyclomerrillianolide[16] by
comparison of the NMR and MS data with those reported.
2, 4-Dihydroxy-allylbenzene-2-O-β-D-glucopyranosi-
de (1) Brown gum (MeOH); C15H20O7; [α]15 D −56.9° (c 0.16,
MeOH); IR νmax (KBr) cm-1: 3 397, 2 922, 2 360, 2 134,
WEI Dan-Dan, et al. /Chinese Journal of Natural Medicines 2012, 10(1): 20−23
22 Chin J Nat Med Jan. 2012 Vol. 10 No. 1 2012 年 1 月 第 10 卷 第 1 期


Fig. 2 Key HMBC (H→C) correlations of compound 1
Table 1 1H, 13C NMR and HMBC data of compound 1 in
500 MHz (methanol-d4, TMS)
Position δH mult. (J in Hz) δC HMBC
1 - 122.0 -
2 - 157.5 -
3 6.64, d (2.5) 104.3 C-1, 2, 4, 5
4 - 158.0 -
5 6.39, dd (8.0, 2.5) 110.3 C -1, 3, 4
6 6.90 ,d (8.0) 131.4 C - 2, 4, 7
7 3.34, d (7.0) 34.7 C -1, 2, 5, 8, 9
8 5.97, ddt (17.0, 10.5, 7.0) 139.4 C -7
9α 5.00, dq (17.5, 2.0) 115.1 C -7
9β 4.94, ddt (10.5, 2.0, 1.0) C -7
1 4.83, d (7.5) 102.9 C -2
2 3.45, m 75.2 C-4
3 3.45, m 78.3 C -1, 5, 2
4 3.40, m 71.5 C -2, 5
5 3.40, m 78.5 C -3, 4
6α 3.91, dd (12.5, 1.5) 62.8 C -4
6β 3.72, dd (12.0, 4.5) -

1 510, 1 457, 1 385, 1 285, 1 171, 1 152, 1 075, 1 044, 822,
642; UV (MeOH) λmax (log ε) 206 (5.28), 279 (4.54) nm.
Oligandrumin B (2) Colorless prism (MeOH);
C17H24O7; 1H NMR (300 MHz, pyrdine-d5) δ: 5.64 (2H, q, J
= 6.3 Hz, H-5), 4.44 (1H, d, J = 13.2 Hz, H-14α), 4.12 (1H, d,
J = 13.5 Hz, H-14β), 3.21 (1H, d, J = 17.8 Hz, H-10α), 3.05
(1H, d, J = 17.8, 2.0 Hz, H-10β), 3.04 (1H, d, J = 12.9 Hz,
H-8α), 2.78 (1H, d, J = 13.2 Hz, H-8β), 2.58 (1H, m, H-2α),
2.38 (1H, m, H-3α), 2.08 (1H, dd, J = 13.8, 9.0 Hz, H-2β),
2.04 (3H, s, H-17), 1.89 (1H, dd, J = 14.1, 9.6 Hz, H-3β),
1.64 (1H, d, J = 6.3 Hz, H-12), 1.36 (3H, s, H-15), 1.14 (3H,
s, H-13); 13C NMR (75 MHz, pyrdine-d5) δ: 175.0 (C-11),
172.6 (C-7), 169.3 (C-16), 96.4 (C-1), 87.1 (C-4), 70.9 (C-6),
69.6 (C-14), 55.1 (C-9), 48.1 (C-5), 37.2 (C-10), 37.0 (C-8),
35.0 (C-2), 33.3 (C-3), 24.6 (C-17), 21.2 (C-15), 18.2 (C-12),
15.7 (C-13); ESI-MS m/z 358.2 [M + NH4]+, 385.2 [M +
COO]－.
Oligandrumin D (3) Colorless prism (MeOH);
C15H20O6; 1H NMR (500 MHz, pyrdine-d5) δ: 4.49 (2H, s,
H-14), 3.68 (1H, d, J = 17.8 Hz, H-10α), 3.00 (1H, d, J =
13.2 Hz, H-8α), 2.98 (1H, d, J = 13.2 Hz, H-8β), 2.93 (1H, d,
J = 17.5 Hz, H-10β), 2.51 (1H, m, H-2α), 2,25 (3H, s, H-12),
2.22 (1H, m, H-3α), 2.05 (1H, dd, J = 13.7, 9.0 Hz, H-3β),
1.84 (2H, dd, J = 14.2, 9.0 Hz, H-2β), 1.39 (6H, s, H-13, 15);
13C NMR (125 MHz, pyrdine-d5) δ: 212.3 (C-6), 175.4
(C-11), 172.3 (C-7), 96.8 (C-1), 87.5 (C-4), 69.3 (C-14), 57.1
(C-5), 56.0 (C-9), 36.9 (C-10), 36.7 (C-8), 34.7 (C-2), 34.0
(C-3), 29.0 (C-12), 24.5 (C-15), 19.4 (C-13); ESI-MS m/z
615.2 [2M + Na]+, 319.1 [M + Na]+, 331.1 [M + Cl]－.
Anisatin (4) White needle crystal (MeOH); C15H20O8;
1H NMR (300 MHz, methanol-d4) δ: 5.51 (1H, s, H-3β), 4.48
(1H, d, J = 6.6 Hz, H-14β), 4.23 (1H, m, H-10), 4.20 (1H, s,
H-7), 4.05 (1H, d, J = 6.6 Hz, H-14α), 2.51 (1H, m, H-1),
2.47 (1H, m, H-8α), 2.06 (1H, dd, J = 14.7, 3.6 Hz, H-2α),
1.94 (1H, ddd, J = 18.0, 12.9, 8.7 Hz, H-2β), 1.78 (1H, m,
H-8β), 1.52 (3H, s, H-12), 1.01 (3H, d, J = 6.9 Hz, H-15); 13C
NMR (125 MHz, methanol-d4) δ: 176.1 (C-11), 169.6 (C-13),
85.7 (C-4), 82.5 (C-7), 75.4 (C-6), 72.0 (C-3), 70.6 (C-10),
65.6 (C-5), 65.5 (C-14), 51.2 (C-9), 41.9 (C-2), 38.1 (C-1),
27.9 (C-8), 21.8 (C-12), 13.6 (C-15); ESI-MS m/z 351.1 [M +
Na]+, 362.9 [M + Cl]－.
Veranisatin D (5) Colorless prism (MeOH); C16H22O9;
1H NMR (500 MHz, methanol-d4) δ: 4.86 (1H, m, H-3α),
4.47 (1H, d, J = 6.5 Hz, H-14α), 4.33 (1H, q, J = 2.0 Hz, H-7),
4.23 (1H, s, H-10α), 4.09 (1H, d, J = 6.5 Hz, H-14β), 4.03
(1H, d, J = 10.5 Hz, H-12), 3.63 (1H, d, J =10.5 Hz, H-12),
3.45 (3H, s, H-16), 2.54 (1H, m, H-1), 2.47 (1H, dd, J = 15.0,
2.0 Hz, H-8α), 2.08 (1H, dd, J = 15.0, 3.5 Hz, H-8β), 2.00
(1H, m, H-2α), 1.77 (1H, m, H-2β), 1.02 (1H, d, J = 7.0 Hz,
H-15); 13C NMR (125 MHz, chloroform-d1) δ: 178.4 (C-11),
172.7 (C-13), 88.2 (C-4), 81.8 (C-7), 81.0 (C-6), 78.4 (C-12),
74.3 (C-3), 73.0 (C-10), 67.5 (C-14), 65.2 (C-5), 62.6 (C-16),
54.4 (C-9), 44.6 (C-2), 40.7 (C-1), 30.0 (C-8), 16.1 (C-15);
ESI-MS m/z 381.1 [M + Na]+, 393.1 [M + Cl]－.
Pseudomajucin (6) Colorless platelet (MeOH);
C15H22O5; 1H NMR (500 MHz, methanol-d4) δ: 4.15 (1H, br s,
H-2), 3.83 (1H, d, J = 9.0 Hz, H-14β), 3.69 (1H, d, J = 9.0 Hz,
H-14α), 2.93 (1H, d, J = 17.5 Hz, H-10β), 2.66 (1H, d, J =
17.5 Hz, H-10α), 2.13-2.23 (3H, m, H-8α, 3β, 3α), 2.00 (1H,
dq, J = 7.0, 4.0 Hz, H-1), 1.86 (1H, q, J = 7.5 Hz, H-6), 1.84
(1H, d, J = 14.0 Hz, H-8β), 1.06 (3H, s, H-13), 1.06 (3H, d, J
= 7.0 Hz, H-12), 1.05 (3H, d, J = 7.0 Hz, H-15); 13C NMR
(125 MHz, methanol-d4) δ: 178.1 (C-11), 106.2 (C-7), 101.0
(C-4), 73.4 (C-2), 70.3 (C-14), 54.2 (C-1), 52.7 (C-8), 50.5
(C-5), 48.3 (C-9), 42.9 (C-3), 42.4 (C-6), 40.4 (C-10), 13.1
(C-13), 8.8 (C-15), 7.1 (C-12); ESI-MS m/z 300.1 [M +
NH4]+, 327.1 [M + COO]
－.
1α-Hydroxy-3-deoxy-pseudoanisatin (7) Colorless
platelet (MeOH); C15H22O6; 1H NMR (500 MHz, metha-
nol-d4) δ: 4.50 (1H, d, J = 14.0 Hz, H-14β), 3.95 (1H, d, J =
14.0 Hz, H-14α), 3.43 (1H, dd, J = 16.5, 2.0 Hz, H-8β), 2.78
(1H, dd, J = 15.0, 2.0 Hz, H-10α), 2.62 (1H, d, J = 15.0 Hz,
H-10β), 2.39 (1H, ddd, J = 13.5, 12.0, 6.0 Hz, H-3β), 2.29
(1H, d, J = 16.5 Hz, H-8α), 2.17 (1H, ddd, J = 15.0, 10.5, 6.0
Hz, H-2β), 2.10 (1H, ddd, J = 15.0, 11.5, 3.5 Hz, H-2α), 2.02
(1H, ddd, J = 13.5, 10.0, 3.5 Hz, H-3α), 1.35 (3H, s, H-15),
1.28 (3H, s, H-13), 1.17 (3H, s, H-12); 13C NMR (125 MHz,
WEI Dan-Dan, et al. /Chinese Journal of Natural Medicines 2012, 10(1): 20−23
2012 年 1 月 第 10 卷 第 1 期 Chin J Nat Med Jan. 2012 Vol. 10 No. 1 23

methanol-d4) δ: 207.1 (C-7), 173.4 (C-11), 88.8 (C-4), 82.5
(C-1), 77.8 (C-6), 69.5 (C-14), 51.5 (C-9), 46.4 (C-5), 38.9
(C-10), 37.4 (C-8), 36.5 (C-2), 30.0 (C-3), 22.4 (C-15), 16.4
(C-12), 12.2 (C-13); ESI-MS m/z 321.1 [M + Na]+, 333.1 [M
+ Cl]－.
8α-Hydroxy-10-deoxycyclomerrillianolide (8) Col-
orless platelet (MeOH); C15H22O7; 1H NMR (500 MHz, di-
methyl sulfoxide-d6) δ: 6.33 (1H, s, OH-1), 5.50 (1H, d, J =
10.5 Hz, OH-8), 5.46 (1H, s, OH-6/7), 4.30 (1H, s, OH-6/7),
4.06 (1H, d, J = 14.0 Hz, H-14β), 4.04 (1H, d, J = 14.0 Hz,
H-14α), 3.99(1H, d, J = 10.2 Hz, H-8β), 3.90 (1H, br s,
H-10α), 2.82 (1H, br s, H-10β), 2.00 (1H, m, H-3α), 1.92 (1H,
m, H-2α), 1.90 (1H, m, H-2β), 1.88 (1H, m, H-3β), 1.31 (3H,
s, H-15), 1.15 (3H, s, H-13), 0.83 (3H, s, H-12); 13C NMR
(125 MHz, dimethyl sulfoxide-d6) δ: 173.1 (C-11), 108.9
(C-7), 93.1 (C-4), 86.9 (C-1), 77.5 (C-6), 77.0 (C-8), 68.5
(C-14), 57.9 (C-9), 50.6 (C-5), 39.0 (C-2), 35.8 (C-10), 25.2
(C-3), 23.5 (C-15), 19.1 (C-12), 17.7 (C-13); ESI-MS m/z
315.0 [M + H]+, 349.0 [M + Cl]－.
All of the eight compounds have been evaluated for their
effects on the growth of non-small cell lung cancer cell line
A549, exhibiting no cytotoxicity.
References
[1] Flora of China [M]. Science press: Beijing, 1996, 30(1): 199.
[2] Moriyama M, Huang JM, Yang CS, et al. Structure and neuro-
trophic activity of novel sesqui-neolignans from the pericarps
of Illicium fargesii [J]. Tetrahedron, 2007, 63(20): 4243-4249.
[3] Zhu Q, Tang CP, Ke CQ, et al. Sesquiterpenoids and phenyl-
propanoids from pericarps of Illicium oligandrum [J]. J Nat
Prod, 2009, 72(2): 238-242.
[4] Tang WZ, Ma SG, Yu SS, et al. Rearranged prenylated C6-C3
compounds and a highly oxygenated seco-prezizaane-type
sesquiterpene from the stem bark of Illicium oligandrum [J]. J
Nat Prod, 2009, 72(6): 1017-1021.
[5] Kubo M, Okada C, Huang JM, et al. Novel pentacyclic
seco-prezizaane-type sesquiterpenoids with neurotrophic prop-
erties from Illicium jiadifengpi [J]. Org Lett, 2009, 11(22):
5190-5193.
[6] Yang CS, Wang JL, Zhang ZL, et al. Studies on the toxic con-
stituents of Illicium simonsii Maxim. [J].Acta Pharm Sin, 1991,
26(2): 128-131.
[7] Kouno I, Iwamoto C, Kameda Y, et al. A new triphenyl-type
neolignan and a biphenylneolignan from the bark of Illicium
simonsii [J]. Chem Pharm Bull, 1994, 42(1): 112-114.
[8] Wu XF, Li Y, Lu HN, et al. Prenylated C6-C3 compounds from
the fruits of Illicium simonsii [J]. J Asian Nat Prod Res, 2009,
11(12): 1056-1061.
[9] Shang XY, Guo MR, Zhao CW, et al. Studies on chemical
constituents of Illicium simonsii [J]. China J Chin Mater Med,
2008, 33(21): 2490-2492.
[10] Eskander J, Lavaud C, Pouny I, et al. Saponins from the seeds
of Mimusops laurifolia [J]. Phytochemistry, 2006, 67(16):
1793-1799.
[11] Park HJ, Jung WT, Basnet P, et al. Syringin 4-O-β-glucoside, a
new phenylpropanoid glycoside, and costunolide, a nitric oxide
synthase inhibitor, from the stem bark of Magnolia sieboldii [J].
J Nat Prod, 1996, 59(12): 1128-1130.
[12] Duus J, Gotfredsen C, Bock K. Carbohydrate structural deter-
mination by NMR spectroscopy: modern methods and limita-
tions [J]. Chem Rev, 2000, 100(12): 4589-4614.
[13] Kouno I, Hashimoto M, Enjoji S, et al. Isolation of neoanisatin
derivatives from the pericarps of Illicium majus with other con-
stituents [J]. Chem Pharm Bull, 1991, 39(7): 1773-1778.
[14] Kouno I, Baba N, Hashimoto M, et al. A new sesquiterpene
lactone and its glucoside from the pericarps of Illicium majus
[J]. Chem Pharm Bull, 1989, 37(9): 2427-2430.
[15] Huang JM, Yang CS, Wang H, et al. Structures of novel ses-
quiterpenes from the pericarps of Illicium merrillianum [J].
Chem Pharm Bull, 1999, 47(12): 1749-1752.
[16] Huang JM, Yang CS, Zhao R, et al. Seven novel seco-pre-
zizaane-type sesquiterpenes from the pericarps of Illicium mer-
rillianum [J]. Chem Pharm Bull, 2004, 52(1): 104-107.

野八角果实中的一个新苯丙素糖苷
魏丹丹, 汪俊松*, 张 耀, 孔令义
中国药科大学天然药物化学教研室, 南京 210009
【摘 要】 目的：研究野八角果实的化学成分及生物活性。方法：应用硅胶、反相及半制备 HPLC 色谱法对野八角果实的
乙醇提取物进行分离纯化, 并用 MTT 法对所分离化合物进行细胞毒活性测试。结果：分离鉴定了 8 个化合物，包括 1 个新的苯
丙素糖苷 2, 4-dihydroxy-allylbenzene-2-O-β-D-glucopyranoside (1)和 7 个已知的倍半萜内酯 oligandrumin B (2), oligandrumin D
(3), anisatin (4), veranisatin D (5), pseudomajucin (6), 1α-hydroxy-3-deoxy-pseudoanisatin (7), 8α-hydroxy-10-deoxycyclomerri-
llianolide (8)。结论：化合物 1, 2, 3, 5−8 为首次从野八角果实中分离得到，所有化合物对非小细胞肺癌 A549 细胞株均无细胞毒
活性。
【关键词】 野八角; 苯丙素糖苷; 倍半萜内酯; 细胞毒

【基金项目】 国家自然科学基金 (No. 30801514)资助项目