全 文 ： 2012 年 9 月 第 10 卷 第 5 期 Chin J Nat Med Sep. 2012 Vol. 10 No. 5 383

Chinese Journal of Natural Medicines 2012, 10(5): 0383−0387
doi: 10.3724/SP.J.1009.2012.00383
Chinese
Journal of
Natural
Medicines







Sesquiterpenes and lignans from the fruits of Illicium si-
monsii and their cytotoxicities
YIN Peng-Jun, WANG Jun-Song, WANG Peng-Ran, KONG Ling-Yi*
Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
Available online Sep. 2012
[ABSTRACT] AIM: To study the constituents and bioactivity of Illicium simonsii. METHODS: Compounds were isolated by a com-
bination of chromatographic materials, silica gel, ODS, and Sephadex LH-20, and finally purified by preparative HPLC. Their struc-
tures were elucidated on the basis of spectroscopic methods, and they were evaluated for their cytotoxic activities by the MTT method.
RESULTS: Seven compounds were obtained and were identified as veranisatin F (1), anisatin (2), (1S)-minwanenone (3), honokiol (4),
macranthol (5), (+)-pinoresinol (6), and matairesinol (7). CONCLUSIONS: Compound 1 is a new seco-prezizaane-type sesquiterpene,
while compounds 6 and 7 were isolated from Illicium simonsii for the first time. Compounds 2 and 3 showed strong inhibitory activities
against the growth of NCI-H460 and SMMC-7721 cells comparable to 5-fluorouracil, and compound 7 to a lesser extent; the other
isolates showed no cytotoxicity.
[KEY WORDS] Illiciaceae; Illicium simonsii; Seco-prezizaane-type sesquiterpene; Lignans; Cytotoxicity
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2012)05-0383-05

1 Introduction
The genus Illicium, belonging to the family Illiciaceae,
is a rich source of seco-prezizaane-type sesquiterpenes [1-3]
that are classified into six subtypes, anisatin, pseudoanisatin,
majucin, pseudomajucin, minwanensin, and cycloparviflora-
lone [4], showing diverse biological activities including an-
timicrobial, neurotoxic and neurotrophic effects [3-5]. I. si-
monsii Maxim. is distributed mainly in India, Myanmar, and
the southwestern part of China [6]. The fruits and stem barks
contain highly oxygenated seco-prezizaane-type sesquiter-
penes [7], neolignans [8], rearranged prenylated C6-C3 com-
pounds [9]. Some neolignans and highly oxygenated seco-
prezizaane-type sesquiterpenes were found to possess cyto-
toxicities in previous research [10-11]. According to our recent
study, the chemical constituents of I. simonsii showed inhibi-
tory activities against the growth of cancer cell lines [12]. As a

[Received on] 23-Apr.-2012
[Research funding] The project was supported by the Key Project of
National Natural Science Foundation of China (No. 30830116) and
Project Funded by the Priority Academic Program Development of
Jiangsu Higher Education Institutions (PAPD).
.[*Corresponding author] KONG Ling-Yi: Prof., Tel/Fax: 86-25-
83271405, E-mail: cpu_lykong@126.com
These authors have no any conflict of interest to declare.
continuation of our work on structurally interesting and bio-
logically significant secondary metabolites of plant origin, we
reinvestigated the fraction of less polar components (PE frac-
tion) and conducted a more intensive study into its chemical
constituents. This paper describes the extraction, isolation,
and structural characterization of a new seco-prezizaane-type
sesquiterpene (1, named as veranisatin F) and a series of
known compounds (2−7) (Fig. 1), and also evaluated their
cytotoxic activities using NCI-H460 and SMMC-7721 human
cell lines.
2 Results and Discussion
Veranisatin F (1), isolated as a colorless oil, has a mole-
cular formula of C23H26O10 as determined by HR-ESI-MS at
m/z 485.141 6 [M + Na]+ (Calcd. for C23H26O10Na 485.141 8),
suggesting eleven degrees of unsaturation. The IR absorp-
tions implied the presence of hydroxyl (3 480, 3 470 cm−1),
aromatic ring (1 632, 1 400, and 923 cm−1), and lactone (1
826 cm−1) functionalities. The 1H NMR spectrum (Table 1) of
1 showed the presence of a benzene ring [δH 8.01 (2H, d, J =
8.5 Hz, H-2′ and H-6′), 7.49 (2H, dd, J = 8.5, 7.5 Hz, H-3′
and H-5′), 7.63 (1H, t, J = 7.5 Hz, H-4′)] and three hydroxyls
[δH 6.40 (1H, s), 6.68 (1H, s), 6.71 (1H, s)]. The NMR data
of 1 were similar to those of veranisatin D [4], except for one
hydroxyl less and one ester carbonyl carbon signal more than
YIN Peng-Jun, et al. /Chinese Journal of Natural Medicines 2012, 10(5): 383−387
384 Chin J Nat Med Sep. 2012 Vol. 10 No. 5 2012 年 9 月 第 10 卷 第 5 期


Fig. 1 Chemical structures of 1-7
Table 1 1H (500 MHz) and 13C NMR (125 MHz) data of 1 in
DMSO-d6
1
No. δC (multi) δH (multi, J in Hz) HMBC
1 36.1 (d) 2.44 (m) C-10, C-2, C-9
2 37.3 (t) 1.83 (m) 2.01 (m) C-1, C-4, C-3, C-15
3 73.8 (d) 5.94 (dd, 10.0, 6.0) C-2, C- C-7′
4 83.6 (s) - -
5 61.2 (s) - -
6 76.6 (s) - -
7 76.8 (d) 4.28 (dd, 3.5, 2.0) C-5, C-9, C-11
8 25.6 (t) 2.34 (dd, 10.5, 1.5) 2.13 (dd, 14.0, 4.0) C-6,C-7,C-10,
9 50.5 (s) - -
10 68.4 (d) 4.23 (s) C-1, C-9, C-11
11 173.0 (s) - -
12 74.3 (t) 3.54 (d, 11.0) 3.90 (d, 11.0) C-6, OCH3
13 167.7 (s) - -
14 62.9 (t) 4.01 (d, 6.5) 4.22 (d, 6.5) C-4, C-5, C-6, C-13
15 13.2 (q) 0.98 (d, 7.0) C-1, C-2, C-9
OCH3 59.3 (q) 3.32, 3H, (s) -
1′ 129.5 (s) - -
2′, 6′ 129.6 (d) 8.01(d, 8.5) C-1′, C-7′
3′, 5′ 128.3 (d) 7.49(dd, 8.5, 7.5) C-1′, C-7′
4′ 133.1 (d) 7.63(t, 7.5) C-2′, C-3′,
7′ 165.5 (s) - -
OH-4 6.71 (s) -
OH-6 6.68 (s) -
OH-10 6.40 (s) C-10

veranisatin D, suggesting that 1 reflected a further esterifica-
tion of veranisatin D. The HMBC correlations (Fig. 2) from
H-3, H-3′, H-6′ to C-7′ at δC 165.5, revealed that a benzoate
group was located at C-3. These combined spectroscopic data
suggested the planar structure in Fig. 2 for veranisatin F. The
relative configuration of 1 was established by the ROESY
spectrum (Fig. 2). A cross-peak of H3-15β/ OH-10 suggested
that OH-10 was β-oriented. Correlation of OH-10β/H-8b
revealed that H-8b was β-oriented; thus, the H-8a was in an
α-orientation. Correlations of H-8a/H-7 and H-7/OH-6 re-
vealed that H-7 and OH-6 were both α-oriented. Correlations
of H3-15β/H-2b and H-2b/H-3 indicated that H3-15, H-2b and
H-3 were on the same face. The β-orientation of H-3 was
assigned by the key ROESY correlation of H-3/H-2b. Thus, 1
was established as 3α-benzoylateveranisatin D, and named as
veranisatin F.

Fig. 2 Key HMBC correlations and selective ROESY cor-
relations of 1
The known compounds 2-7 were identified as anisa-
tin [13], (1S)-minwanenone [2], honokiol [14], macranthol [15],
(+)-pinoresinol [16], matairesinol [17] by comparison of the
NMR and MS data with those reported.
Veranisatin F (1) Colorless oil (Methanol); [α]24.4 D
−131.1 (c 0.07, methanol); UV (methanol) λmax: (log ε) 201
(1.3), 229 (1.6), 273 (0.9), 280 (0.7) nm; IR (KBr) νmax cm−1:
3 480, 3 470, 1 826, 1 725, 1 632, 1 400, 1 110, 923, 717;
ESI-MS m/z 461.1 [M − H]−; HR-ESI-MS m/z 485.1416 [M
YIN Peng-Jun, et al. /Chinese Journal of Natural Medicines 2012, 10(5): 383−387
2012 年 9 月 第 10 卷 第 5 期 Chin J Nat Med Sep. 2012 Vol. 10 No. 5 385

+ Na]+ (Calcd. for C23H26O10Na 485.141 8), 1H and 13C NMR
data see Table 1.
Anisatin (2) White needle crystals (MeOH); mp
119−120 °C; [α]24.4 D −23.3 (c 0.15, methanol); 1H NMR (500
MHz, CD3OD) 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, CD3OD)
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]−.
(1S)-Minwanenone (3) Colorless oil (MeOH); [α]24.4 D
−18.2 (c 1.20, methanol); 1H NMR (500 MHz, CD3OD) δ:
6.01 (1H, s, H-3), 4.65 (1H, ddd, J = 4.4, 2.4, 2.2 Hz, H-7),
3.46 (1H, d, J = 11.5 Hz, H-14α), 3.54 (1H, d, J = 11.5 Hz,
H-14β), 2.88 (1H, d, J = 18.9 Hz, H-10α), 2.45 (1H, dd, J =
13.7, 7.4 Hz, H-8β), 2.44 (1H, dd, J = 18.9, 2.6 Hz, H-10β),
2.41 (1H, q, J = 7.4 Hz, H-1), 1.94 (1H, qd, J = 7.4, 2.4 Hz,
H-6), 1.87 (1H, ddd, J = 13.7, 2.4, 2.2 Hz, H-8α), 1.34 (1H, s,
H-3), 1.20 (3H, d, J = 7.4 Hz, H-12), 1.09 (3H, d, J = 7.4 Hz,
H-15); 13C NMR (125 MHz, CD3OD) δ: 210.6 (C-2), 187.5
(C-4), 173.5 (C-11), 131.3 (C-3), 81.1 (C-7), 65.6 (C-14),
53.8 (C-1), 46.1 (C-6), 45.8 (C-9), 44.6 (C-5), 39.0 (C-10),
37.5 (C-8), 24.9 (C-13), 12.4 (C-12), 10.1 (C-15); ESI-MS
m/z 265.1 [M + H]+.
Honokiol (4) Colorless needles (CHCl3); mp 86−87
°C; [α]24.4 D ±0 (c 0.13, CHCl3); 1H NMR (500 MHz, CDCl3) δ:
7.20 (1H, d, J = 2 Hz, H-2), 7.19 (1H, dd, J = 8.79, 2.0 Hz,
H-6), 7.06 (1H, dd, J = 8.79, 1.95 Hz, H-4′), 7.01 (br s), 6.88
(1H, d, J = 8.79 Hz, H-5 and H-3′), 5.77-6.23 (2H, m, H-8
and H-8′), 4.98-5.26 (4H, m, H-9 and H-9′), 3.44 (2H, d, J =
6.4 Hz, H-7), 3.34 (2H, d, J = 6.6 Hz, H-7′); 13C NMR (125
MHz, CDCl3) δ: 153.6 (C-4), 150.5 (C-2′), 137.7 (C-8′),
136.0 (C-8), 132.3 (C-5′), 131.0 (C-2), 130.3 (C-1), 129.6
(C-6′), 128.8 (C-4′), 128.4 (C-6), 127.8 (C-1′), 126.5 (C-3),
116.7 (C-9), 116.4 (C-3′), 115.7 (C-5), 115.5 (C-9′); 39.3
(C-7′), 34.9 (C-7); ESI-MS m/z 267.1 [M + H]+.
Macranthol (5) Colorless needles (methanol); mp
139−140 °C; [α]24.4 D +9.3 (c 0.33, methanol); 1H NMR (500
MHz, CD3OD) δ: 7.30 (1H, d, J = 2.2 Hz, H-2), δ: 7.26 (1H,
d, J = 2.2 Hz, H-6), 7.15 (1H, dd, J = 8.1, 2.2 Hz, H-4′′), 7.10
(1H, d, J = 2.2 Hz, H-6′′), 7.06 (1H, d, J = 2.2 Hz, H-6′), 7.05
(1H, dd, J = 9.2, 2.2 Hz, H-4′), 6.96 (1H, d, J = 8.1 Hz, H-3′′),
6.89 (1H, d, J = 9.2 Hz, H-3′), 6.07 (1H, ddd, J = 17.2, 10.3,
6.6 Hz, H-8), 5.97 (1H, ddd, J = 16.9, 10.3, 6.6 Hz, H-8′′),
5.95 (1H, ddd, J = 16.9, 10.3, 6.6 Hz, H-8′), 5.20 (1H, dd, J =
17.2, 1.5 Hz, H-9α), 5.15 (1H, dd, J = 10.3, 1.5 Hz, H-9β),
5.08 (1H, dd, J = 16.9, 1.8 Hz, H-9′α), 5.08 (1H, dd, J = 16.9,
1.8 Hz, H-9′′α), 5.06 (1H, dd, J = 10.3, 1.8 Hz, H-9′′β), 5.05
(1H, dd, J = 10.3, 1.8 Hz, H-9′β), 3.53 (2H, br d, J = 6.6 Hz,
H-7), 3.36 (2H, br d, J = 6.6 Hz, H-7′), 3.35 (2H, br d, J = 6.6
Hz, H-7′′); 13C NMR (125 MHz, CD3OD) δ: 151.2 (C-2′′),
150.9 (C-4), 150.8 (C-2′), 137.7 (C-8′′), 137.4 (C-8′), 136.2
(C-8), 133.4 (C-5′′), 132.4 (C-5′), 131.3 (C-6′′), 130.9 (C-2),
130.3 (C-4′′), 130.3 (C-6′), 130.2 (C-1), 130.0 (C-6), 129.0
(C-4′), 128.3 (C-3), 127.5 (C-1′), 124.7 (C-5), 123.3 (C-1′′),
116.8 (C-3′′), 116.7 (C-9), 116.0 (C-9′), 115.8 (C-3′), 115.6
(C-3′′), 39.4 (C-7′′), 39.3 (C-7′), 35.0 (C-7); ESI-MS m/z
397.1 [M − H]−.
(+)-Pinoresinol (6) White needle crystal (CHCl3); mp
115−116 °C; [α]24.4 D +56.7 (c 0.13, CHCl3); 1H NMR (500
MHz, CDCl3) δ: 6.90 (2H, d, J = 1.9 Hz, H-2 and H-2′), 6.89
(2H, d, J = 8.1 Hz, H-5 and H-5′), 6.82 (2H, d, J = 8.1 Hz,
H-6 and H-6′), 4.74 (2H, d, J = 4.3 Hz, H-7 and H-7′), 4.25
(1H, m, H-9), 3.89 (1H, s, H-9′), 3.88 (1H, m, H-9′), 3.10 (2H,
m, H-8 and H-8′); 13C NMR (125 MHz, CDCl3) δ: 146.7 (C-3
and C-3′), 145.2 (C-4 and C-4′), 132.9 (C-1 and C-1′), 118.9
(C-6 and C-6′), 114.2 (C-5 and C-5′), 108.6 (C-2 and C-2′),
85.8 (C-7 and C-7′), 71.6 (C-9 and C-9′), 55.9 (-OCH3), 54.1
(C-8 and C-8′); ESI-MS m/z 357.1 [M − H]−.
Matairesinol (7) a white amorphous powder (CHCl3);
[α]24.4 D − 42.1 (c 0.25, CHCl3); 1H NMR (CDCl3, 500 MHz) δ:
6.82 (1H, d, J = 8.0, H-5), 6.77 (1H, d, J = 8.0, H-5′), 6.60
(1H, s, H-2), 6.58(1H, d, J = 2.0, H-6), 6.53(1H, s, H-2′),
6.50 (1H, s, H-6′), 4.10(1H, m, H-9′α), 3.82 (1H, m, H-9′β),
2.94 (1H, m, H-7α), 2.83 (1H, m, H-7β), 2.48 (2H, m, H-8
and H-8′); 13C NMR (CDCl3, 125 MHz) δ: 178.6 (C-1), 146.6
(C-3′), 145.6 (C-3′′), 145.5 (C-4′′), 144.4 (C-4′), 130.9 (C-1′),
129.9 (C-1′′), 121.3 (C-6′), 120.7 (C-6′′), 115.4 (C-2′′), 114.4
(C-5′), 111.0 (C-2′), 110.8 (C-5′′), 71.2 (C-4), 55.9 (-OCH3),
55.8 (-OCH3), 46.3 (C-2), 41.5 (C-3), 38.3 (C-5), 34.5 (C-6);
ESI-MS m/z 357.1 [M − H]−.
Compounds 1−7 were evaluated for their cytotoxic ac-
tivities by the MTT method in 96-well microplates [18], using
two human cancer cell lines NCI-H460 (human large cell
lung cancer cell line) and SMMC-7721 (human hepato-
cellular carcinoma cell line), with 5-fluorouracil (5-FU) as
positive control (Table 2). Compounds 2 and 3 showed strong
activities comparable to 5-fluorouracil, and 7 to a lesser ex-
tent; the other compounds showed no cytotoxicity.
Table 2 Cytotoxicity data of compounds 1-7, given as IC50
values ( x ± s, n = 3)
Cell lines
Sample
NCI-H460 SMMC-7721
1 - -
2 16.77 ± 0.34 21.84 ± 0.29
3 12.06 ± 0.12 24.66 ± 1.03
4 - -
5 - -
6 - -
7 62.09 ± 0.95 81.32 ± 0.51
5-FU 11.04 ± 0.31 14.51 ± 0.17
YIN Peng-Jun, et al. /Chinese Journal of Natural Medicines 2012, 10(5): 383−387
386 Chin J Nat Med Sep. 2012 Vol. 10 No. 5 2012 年 9 月 第 10 卷 第 5 期

3 Experimental
3.1 General experimental procedures
Optical rotations were determined with a JASCO P-1020
polarimeter (Na filter, λ = 589 nm). CD spectra were obtained
on a JASCO 810 spectropolarimeter. IR spectra were re-
corded on a Bruker Tensor 27 spectrometer with KBr-disks.
Mass spectra were obtained on a MS Agilent 1100 Series
LC/MSD Trap mass spectrometer (ESI-MS) and HR-ESI-MS
was done on an Agilent 6520B Q-TOF spectrometer, respec-
tively. NMR spectra were recorded on Bruker Avance III 500
NMR instrument (1H: 500 MHz, 13C: 125 MHz) with TMS as
internal standard. Silica gel (200−300 mesh, Qingdao Hai-
yang Chemical Co., Ltd., China), Sephadex LH-20 (Phar-
macia, USA), and Rp-C18 (40−63 μm, Fuji Silysia, Chemical
Ltd., Japan) were used for column chromatography. Fractions
were monitored by TLC. Spots were visualized by heating
silica gel plates immersed in vanillin-H2SO4 in ethanol.
Preparative HPLC was performed on a Shimpack Rp-C18
column (20 mm × 200 mm, i.d.) with a flow rate of 10
mL/min using an Agilent 1100 Series LC instruction with
UV detection (Agilent 1100 multiple wavelength detector).
All solvents used were of analytical grade (Jiangsu Hanbang
Sci. & Tech. Co., Ltd., China).
3.2 Plant material
The dried fruits of I. simonsii were collected in July
2009 from Kunming, Yunnan Province, and identified by
Professor TAO De-ding of Kunming Institute of Botany,
Chinese Academy of Sciences. A voucher specimen (No.
IS200907) has been deposited in the Herbarium of the De-
partment of Natural Medicinal Chemistry, China Pharmaceu-
tical University, Nanjing, China.
3.3 Extraction and isolation procedure
Powdered fruits of I. simonsii (10 kg) were extracted
with 95% ethanol and concentrated under reduced pressure to
produce a browny extract of 1.2 kg, which was then parti-
tioned sequentially with petroleum ether (PE), CH2Cl2,
EtOAc and n-BuOH. The PE extract (125 g) was fractionated
by silica-gel CC eluting with petroleum ether−EtOAc (50 : 1
to 0 : 1) to give six fractions (fractions I-VI).
Fraction V (8.0 g) was subjected to a Si gel column
eluted with CH2Cl2−MeOH (80 : 1 to 0 : 1), purified by ODS
with MeOH−H2O (7 : 3 to 1 : 0) and Sephadex LH-20
(CH2Cl2 −MeOH 1 : 1) chromatography and then subjected to
preparative HPLC eluted with MeOH−H2O (90 : 10) to af-
ford 2 (10.0 mg, tR 25.8 min) and 3 (14.8 mg, tR 31.2 min).
Fraction VI (10.5 g) was futher fractionated to afford five
subfractions using silica gel CC eluted with CH2Cl2−MeOH
(80 : 1 to 0 : 1). Fraction VID (2.4 g) was subjected ODS
with MeOH− H2O (5 : 5 to 1 : 0) as mobile phase to afford
six subfractions. Of these, fraction VIDC (500 mg) was first
fractionated to five subfractions by ODS with MeOH−H2O
(7 : 3 to 0 : 1) and then was subjected to Rp-C18 preparative
HPLC eluted with MeOH−H2O (80 : 20) to obtain 1 (3.2 mg,
tR 12.5 min), 6 (2.7 mg, tR 20.8 min) and 7 (2.5 mg, tR 28.2
min). Similarly, compounds 4 (26.0 mg, tR 10.8 min) and 5
(18.6 mg, tR 18.3 min) were obtained by ODS column chro-
matography with MeOH−H2O (4 : 6 to 1 : 0) and Rp-C18
preparative HPLC of the fraction VIDB (1.5 g) eluted with
MeOH−H2O (75 : 25).
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野八角果实中的倍半萜和木脂素及其细胞毒活性
尹鹏军, 汪俊松, 王朋然, 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、凝胶色谱及制备 HPLC 对野八角果实
的乙醇提取物进行分离纯化, 并且通过光谱方法鉴定化合物结构。进一步用 MTT 法对所分离化合物进行细胞毒活性测试。结果：
7 个化合物被分离并鉴定为：veranisatin F (1), anisatin (2), (1S)-minwanenone (3), honokiol (4), macranthol (5), (+)-pinoresinol (6),
matairesinol (7)。结论：化合物 1 是一个新的高氧化裂-prezizaane 型倍半萜, 化合物 6 和 7 首次从野八角中分离得到。5-氟脲嘧
啶作为阳性对照, 化合物 2 和 3 对人大细胞肺癌细胞株和人肝癌细胞株的增长有较强的的抑制活性, 7 则比较微弱, 其他化合物
显示无细胞毒活性。
【关键词】 八角属; 野八角; 高氧化裂-prezizaane 型倍半萜; 木脂素；细胞毒

【基金项目】 国家自然科学基金重点项目(No. 30830116)和江苏省优势学科资助项目资助