Fitoterapia 93 (2014) 126131

Contents lists available at ScienceDirect

Fitoterapia
journal homepage: www.elsevier.com/locate/fitote

Chaetoglobosin Y, a new cytochalasan from

Chaetomium globosum
Qi-Chang Zheng a,1, Ming-Zhu Kong b,1, Qin Zhao a, Guo-Dong Chen c,, Hai-Yan Tian a,
Xiao-Xia Li a, Liang-Dong Guo d, Jia Li e, Yi-Zhi Zheng b, Hao Gao a,
a
b
c
d
e

Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, PR China
Shenzhen Key Laboratory of Microbial Genetic Engineering, College of Life Sciences, Shenzhen University, Shenzhen 518060, PR China
Department of Pharmaceutical Engineering, South China Agricultural University, Guangzhou 510642, PR China
State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China
National Center for Drug Screening, and State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai 201203, PR China

a r t i c l e

i n f o

Article history:
Received 23 September 2013
Accepted in revised form 21 December 2013
Available online 11 January 2014
Keywords:
Chaetomium globosum
Chaetomiaceae
Cytochalasans
Chaetoglobosins
Cytotoxicity

a b s t r a c t
Chaetoglobosin Y (1), was isolated from the endolichenic fungal strain Chaetomium globosum
(No. 64-5-8-2), along with related six known cytochalasans, chaetoglobosin Fex (2), chaetoglobosin
E (3), isochaetoglobosin D (4), chaetoglobosin G (5), cytoglobosin B (6), and cytoglobosin C (7). Their
structures were determined by detailed spectroscopic analyses and comparison with those of the
closely related compounds previously reported. The cytotoxicity to HCT-116 cell line of 27 was
evaluated in vitro with doxorubicin as positive control.
2014 Elsevier B.V. All rights reserved.

1. Introduction
Cytochalasans are a large group of fungal alkaloids with
tricyclic core, which consists of a macrocyclic ring (either a
carbocycle, a lactone or a cyclic carbonate) and an isoindolone
moiety. These fungal alkaloids are contributed by a polyketide backbone and an amino acid (either leucine, phenylalanine or tryptophan) with diverse bioactivities, such as
antimicrobial, antiparasitic, cytotoxic, and phytotoxic activities
[1]. Cytochalasan-producing fungi are derived from very diverse
ecological settings, including from plant [15] and marine [1,6,7].
But there is no report that cytochalasan was found from the
lichen-derived endophytic fungus. As part of our search for
bioactive secondary metabolites from endolichenic fungi [813],
the chemical investigation of the fungal strain Chaetomium
In commemoration of Professor Xin-Sheng Yao's 80th birthday.
Corresponding authors. Tel./fax: +86 20 85221559.
E-mail addresses: chgdtong@163.com (G.-D. Chen), tghao@jnu.edu.cn
(H. Gao).
1
These authors contributed equally to this work.
0367-326X/$ see front matter 2014 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.tote.2013.12.022

globosum (No.64-5-8-2) was carried out, which led to the

isolation of a new cytochalasan, chaetoglobosin Y (1), along
with related six known cytochalasans, chaetoglobosin Fex (2)
[6,14], chaetoglobosin E (3) [15], isochaetoglobosin D (4) [6],
chaetoglobosin G (5) [15], cytoglobosin B (6) [6], and
cytoglobosin C (7) [6] (Fig. 1). Details of the isolation, structure
characterization and cytotoxicity are reported herein.

2. Experimental
2.1. General experimental procedures
Optical rotations were measured on a JASCO P1020 digital
polarimeter, and UV data were recorded on a JASCO V-550
UV/vis spectrometer. IR data were recorded using a JASCO
FT/IR-480 plus spectrometer. ESI-IT-MS spectra were performed on a Finnigan LCQ Advantage MAX mass spectrometer
and HR-ESI-MS spectra were obtained on a Synapt G2 Mass
Spectrometer (Waters MS Technologies). 1H and 13C NMR data
were acquired with a Bruker AV 400 using solvent signals

Q.-C. Zheng et al. / Fitoterapia 93 (2014) 126131

127

Fig. 1. The structures of 17.

(CDCl3: H 7.26/C 77.0) as internal standards. The analytical

HPLC was performed on a Dionex HPLC system equipped with an
Ultimate 3000 pump, an Ultimate 3000 diode array detector
(DAD), an Ultimate 3000 Column Compartment, an Ultimate
3000 autosampler (Dionex, USA) and an Alltech (Grace) 2000ES
evaporative light scattering detector (ELSD) (Alltech, USA) using
a Phenomex Gemini 5 C18 column (4.6 250 mm, 5 m). The
preparative HPLC was carried out on VARIAN Prostar 210 system
equipped with UV detectors (Varian, USA) and a Phenomex
Gemini 5 C18 column (21.2 250 mm, 5 m). Column
chromatography (CC) was carried out on silica gel (200300
mesh) (Qingdao Haiyang Chemical Group Corporation, Qingdao,
China), and ODS (6080 m, YMC), respectively. TLC was
performed on precoated silica gel plate (SGF254, 0.2 mm, Yantai
Chemical Industry Research Institute, China).
2.2. Fungus material
The strain of Chaetomium globosum was isolated from lichen
Everniastrum nepalense (Taylor) Hale ex Sipman collected in
Zixishan Mountain, Yunnan province, People's Republic of
China, in November, 2005. The isolate was identified by one of
the authors (L.-D. Guo) and assigned the accession number
64-5-8-2 in the culture collection at the Institute of Traditional
Chinese Medicine and Natural Products, College of Pharmacy,
Jinan University, Guangzhou.
The fungus was cultured on slants of potato dextrose agar
(PDA) at 25 C for 5 days. Agar plugs were used to inoculate
four Erlenmeyer flasks (250 mL), each containing 100 mL of
potato dextrose broth (PDB). Four flasks of the inoculated media
were incubated at 25 C on a rotary shaker at 200 rpm for five
days to prepare the seed culture. Fermentation was carried out
in thirty Erlenmeyer flasks (500 mL), each containing 70 g of
rice. Distilled H2O (105 mL) was added to each flask, and the
contents were soaked overnight before autoclaving at 120 C for

30 min. After cooling to room temperature, each flask was

inoculated with 5.0 mL of the spore inoculum and incubated at
room temperature for 40 days.
2.3. Extraction and isolation
The fermented material was extracted three times with
EtOAc, and the organic solvent was evaporated under vacuum
to afford the dry crude extract (21.2 g), which was fractionated
by silica gel CC (3 14 cm) using CHCl3MeOH (100:0 and
0:100, v/v) to afford chloroform fraction (C, 0.8 L, 13.8 g) and
methanol fraction (W, 1 L, 7.3 g). Methanol fraction (W, 7.3 g)
was separated by ODS CC (3 42 cm) eluting with a MeOH
H2O gradient (30:70, 50:50, 70:30 and 100:0, v/v, each 2 L) to
afford 4 fractions (W1 to W4). Fraction W2 (0.9 g) was further
separated by ODS CC (3 42 cm) using a MeOHH2O gradient
(30:70100:0, v/v) to afford 8 subfractions (W2-1 to W2-8)
and 7 (31.9 mg). Subfraction W2-2 (67.0 mg) was purified on
preparative HPLC using MeOHH2O (53:47, v/v) as mobile phase
at a flow rate of 8 mL/min to yield 6 (10.3 mg). Chloroform
fraction (C, 13.8 g) was separated by silica gel CC eluting with a
cyclohexaneEtOAc gradient (100:0, 70:30, 80:20, 100:0, v/v,
each 2 L) to afford 4 fractions (C1 to C4). Fraction C2 (2.7 g) was
further separated by ODS CC (3 42 cm) using a MeOHH2O
gradient (50:50100:0, v/v) to afford 7 subfractions (C2-1 to
W2-7). Subfraction C2-4 (199.8 mg) was subjected to preparative HPLC purification using MeOHH2O (60:40, v/v) at a flow
rate of 8 mL/min to yield 3 (11.2 mg) and 2 (25.4 mg).
Subfraction C2-5 (1.5 g) was subjected to ODS CC (3 42 cm)
using a MeOHH2O gradient (30:70100:0, v/v) to afford 8
sub-subfractions (C2-5-1 to C2-5-8) and to yield 5 (39.2 mg) and
4 (10.5 mg). Sub-subfraction C2-5-7 (91.1 mg) was subjected to
preparative HPLC purification using MeOHH2O (65:35, v/v)
with 0.05% formic acid at a flow rate of 8 mL/min to yield 1
(1.9 mg).

128

Q.-C. Zheng et al. / Fitoterapia 93 (2014) 126131

Table 1
1D NMR and 2D NMR data of compound 1 (in CDCl3).
1
No.

C, mult

1
2-NH
3
4
5
6
7
8
9
10

173.4, qC

H (J in Hz)
6.34,
3.76,
2.60,
2.22,
2.08,

52.3, CH
47.2, CH
35.1, CH
46.3, CH
212.7, qC
52.7, CH
64.4, qC
34.0, CH2

3.65, d (9.4)

11
12
13
14
15

15.7, CH3
16.0, CH3a
124.7, CH
134.5, CH
40.8, CH2

16
17
18
19
20
21

33.2, CH
149.1, CH
134.0, qC
203.4, qC
71.6, CH
31.5, CH2

22

36.5, CH2

23
16-CH3
18-CH3
1-NH
2
3
3a
4
5
6
7
7a

206.5, qC
19.8, CH3
12.2, CH3

123.5,
110.0,
127.1,
118.1,
120.0,
122.5,
111.6,
136.4,

br s
m
m
m
m

CH
qC
qC
CH
CH
CH
CH
qC

H1H COSY

HMBC

4, 10a, 10b
3, 5
4, 11
12
13

ROESY

6
10a, 11, 22b
8
3
1, 7, 9, 13, 14, 23

3.07,
2.73,
1.16,
1.15,
6.04,
5.12,
2.43,
2.08,
2.73,
6.13,

dd (14.3, 2.9), Ha
m, Hb
d (6.6)
d (6.8)
dd (15.4, 9.4)
ddd (15.4, 11.0, 2.6)
br d (14.2), Ha
m, Hb
m
d (8.9)

4.74,
1.89,
1.68,
2.62,
2.16,

t (4.7)
m, Ha
m, Hb
m, Ha
m, Hb

1.02,
1.84,
8.51,
7.06,

d (6.4)
s
br s
br s

2
1-NH

3, 3a, 7a

7.46,
7.13,
7.21,
7.38,

d (7.7)
t (7.5)
t (7.3)
d (7.9)

5
4, 6
5, 7
6

6, 7a
3a, 7
4, 7a
5, 3a

5, 14
4

3
5
6
8, 14
13, 15
14, 16
15b, 17, 16-CH3
16

4, 6
5, 7

19, 18-CH3

21a, 21b
20, 22a,
20
21a

4
15b
8, 16
16-CH3
13, 17
14, 18-CH3
15b, 20

17, 22a

20
4
15, 16, 17
17, 18, 19

15a
16

The assignments maybe interchange.

2.3.1. Chaetoglobosin Y (1)

Colorless amorphous powder; []25
22.9 (c 0.07,
D
MeOH); UV (MeOH) max (log ) 204 (4.57), 238 (4.70),
284 (4.23), 316 (4.21) nm; IR (KBr) max 3418, 2926, 1705,
1454, 1385, 746 cm1; ESI-MS (positive): 553 [M + Na]+,
1083 [2 M + Na]+; ESI-MS (negative) m/z: 529 [M H],
1059 [2 M H]; HRESI-TOF-MS (positive): m/z 553.2678
[M + Na]+ (calcd. for C32H38N2O5Na, 553.2673); 1H and 13C
NMR see Table 1.
2.3.2. X-ray crystallographic analysis of 2
Upon crystallization from MeOH using the vapor diffusion
method, colorless crystals of 2 were obtained. Data were
collected using a Sapphire CCD with a graphite monochromator and Cu K radiation, = 1.5418 at 293(2) K. Crystal
data: C32H38N2O5 CH3OH, M = 562.69, space group orthorhombic, P212121; unit cell dimensions were determined to
be a = 12.1155(3) , b = 12.4576(3) , c = 20.5469(6) ,
= 90.00, = 90.00, = 90.00, V = 3101.15(14) 3,
Z = 4, Dx = 1.205 mg/m3, F (000) = 1208, (Cu K) =
0.666 mm1. 6929 unique reflections were collected to
max = 63.28. 4456 independent reflections were yielded,

with 4161 reflections above the designated intensity threshold

for observation [F2 N 4 (F2)]. The structure was solved by
direct methods using the SHELXS-97 program, and refined by
the program SHELXL-97 and full-matrix least-squares calculations. In the structure refinements, nonhydrogen atoms were
placed on the geometrically ideal positions by the ride on
method. Hydrogen atoms bonded to oxygen were located by
the structure factors with isotropic temperature factors. The
final refinement gave R = 0.0401, RW = 0.1076, and S =
1.059. The crystallographic data for 2 reported in this paper
have been deposited with the Cambridge Crystallographic Data
Centre (CCDC 962643).
2.3.3. X-ray crystallographic analysis of 3
Upon crystallization from CH3CN using the vapor diffusion method, colorless crystals of 3 were obtained. Data were
collected using a Sapphire CCD with a graphite monochromator and Cu K radiation, = 1.5418 at 293(2) K. Crystal
data: C32H38N2O5, M = 530.64, space group monoclinic, P21;
unit cell dimensions were determined to be a = 7.74550(10)
, b = 14.8183(2) , c = 12.3700(2) , = 90.00, =
98.4255(14) , = 90.00, V = 1404.45(4) 3, Z = 2, Dx =

Q.-C. Zheng et al. / Fitoterapia 93 (2014) 126131

1.255 mg/m3, F (000) = 568, (Cu K) = 0.679 mm1.

4503 unique reflections were collected to max = 62.80.
3073 independent reflections were yielded, with 2868
reflections above the designated intensity threshold for
observation [F2 N 4 (F2)]. The structure was solved by direct
methods using the SHELXS-97 program, and refined by the
program SHELXL-97 and full-matrix least-squares calculations. In the structure refinements, nonhydrogen atoms were
placed on the geometrically ideal positions by the ride on
method. Hydrogen atoms bonded to oxygen were located by
the structure factors with isotropic temperature factors. The
final refinement gave R = 0.0335, RW = 0.0865, and S =
1.059. The crystallographic data for 3 reported in this paper
have been deposited with the Cambridge Crystallographic
Data Centre (CCDC 962644).
2.4. Cytotoxicity against HCT-116 cell line in vitro
Cells were kept at logarithmic growth phase in 5% CO2 at
37 C with the corresponding medium supplemented with 10%
fetal bovine serum and 100 units/mL each of penicillin G and
streptomycin. Cells were seeded onto a 96-well plate at a
concentration of 20003000 cells/well and incubated at 37 C in
5% CO2 for 24 h. A range of concentrations of the test compounds
were added and the plate was incubated at 37 C for 72 h before
20 L MTT (5 mg/mL)/well was added. After 3 h of incubation,
the medium was removed and 100 mL DMSO was added to each
well. The absorbance was measured using a SpectraMax 340
microplate reader (Molecular Devices, Sunnyvale, CA, USA) at
550 nm with a reference at 690 nm. The optical density of the
result of the MTT assay was directly proportional to the number
of viable cells. Doxorubicin was used as a positive control.
3. Results and discussion
Chaetoglobosin Y (1) was obtained as an amorphous powder.
Its molecular formula was determined to be C32H38N2O5
(fourteen degrees of unsaturation) on the basis of a quasimolecular ion peak at m/z 553.2678 [M + Na]+ (calcd. for
C32H38N2O6Na, 553.2673) in HRESIMS data. The IR spectrum
showed absorption bands at 3418 and 1705 cm1 were the
characteristics of NH/OH, and carbonyl groups. Analysis of the
1
H, 13C NMR and HSQC spectroscopic data of 1 (Table 1) revealed

129

2 exchangeable protons (H 8.51, and 4.23) and 32 carbon

signals. These carbons can be categorized into eight sp2
quaternary carbons [including four carbonyls (C 212.7, 206.5,
203.4, and 173.4) and four olefinic or aromatic carbons
(C 136.4, 134.0, 127.1, and 110.0)], eight protonated olefinic
or aromatic carbons (C 149.1, 134.5, 124.7, 123.5, 122.5, 120.0,
118.1, and 111.6, respectively), one sp3 quaternary carbons
(C 64.4), seven sp3 methine carbons [including one oxygenated (C 71.6)], four sp3 methylene carbons (C 40.8, 36.5, 34.0,
and 31.5, respectively), and four methyl carbons (C 19.8, 16.0,
15.7, and 12.2, respectively). The protons and protonated carbon
resonances in the NMR spectra of 1 were unambiguously
assigned by DEPT, 1H1H COSY, and HSQC experiments. The
general features of its NMR data (Table 1) closely resembled
those of chaetoglobosin Fex (2) [14]. However, compared with
chaetoglobosin Fex, the signals for the exocyclic olefin 6(12)
and one oxygenated methine carbon were missing in the
spectra of 1. Additional methyl carbon signal at C 16.0 (C-12),
sp3 methine carbon signal at C 46.3 (C-6), and the carbonyl at C
212.7 (C-7) were observed in the 13C NMR spectrum of 1. The
above-mentioned evidences indicated that 1 is the derivative of
chaetoglobosin Fex, whose exocyclic olefin 6(12) was reduced
and 7-OH was oxidized. Combined with the 1H1H COSY
correlations between H3-12 and H-6, the observed HMBC
correlations from H3-11 to C4/C-6, and from H3-12 to C-5/C-7,
from H-8 to C-1/C-7/C-9/C-13/C-14/C-23 confirmed the above
deduction (Fig. 2).
The E-geometry of the 13(14)-double bond was deduced
from the large coupling constant observed for H-13 and H-14
(J1314 = 15.4 Hz). In the 13C NMR spectrum of 1, the similar
chemical shifts of C-16, C-17, C-18, C-19, C-20, C-21, C-22,
and C-23 to those of chaetoglobosin Fex (2) [14] indicated
that the 17(18)-double bond, C-16, C-20 and C-9 in 1 shared
the same configurations with chaetoglobosin Fex (2). In
ROESY spectrum, the observed correlations between H-14
and H-8, between H-14 and H-16, between H-16 and 18-CH3,
between H-15b and H-13, between H-15b and H-17, between
H-20 and H-17, between H-20 and H-22a, supported the
above deduction. The observation of a ROESY correlation
between H-5 and H-8 and the lack of an observable ROESY
correlation between H-4 and H-8 established that the
six-membered ring was in a boat conformation. Moreover,
the ROESY correlations between H-5 and H-8, between H-4

Fig. 2. The key 1H1H COSY, HMBC and ROESY correlations of 1.

130

Q.-C. Zheng et al. / Fitoterapia 93 (2014) 126131

and H-22b, indicated that the cyclohexanone is cis-fused with

-lactam and trans-fused with macrocycle moieties, respectively. In addition, the ROESY correlation between H-4 and
H-10a indicated that H-3 and H-4 are not in the same
orientation in -lactam ring. Combined with the deduction,
the ROESY correlation between H-3 and H-6 indicated that
the configuration of H3-12 is . Therefore, structure of 1 was
elucidated as shown in Fig. 1.
The structures of compounds 2 and 3 were identified as
chaetoglobosin Fex (2) and chaetoglobosin E (3) by the analysis
of 1D, 2D NMR and X-ray crystallography (Fig. 3), whose NMR
data were consistent with previous reported spectra [6,15]. More
than 40 chaetoglobosins have been isolated from the fungal
genus Chaetomium, but only the X-ray data of chaetoglobosin A
has been reported in the past and demonstrated that the sixmembered ring moiety adopts a slightly twisted boat conformation, and the macrocyclic ring moiety containing an E-alkene is
arranged in a chair-like conformation [16]. In this research,
the structures of the isolated compounds are different from
chaetoglobosin A, including the six-membered ring moiety and
the macrocyclic ring moiety. Fortunately, the crystals of 2
and 3 were obtained, and the X-ray data analyses could be
helpful to understand the conformation differences for
various chaetoglobosins. For the macrocyclic ring moiety, the
X-ray data of 2 and 3 clearly showed that the moieties in
chaetoglobosin Fex (2) and chaetoglobosin E (3) share
the same conformation, which is quite different from that of
chaetoglobosin A. On the basis of X-ray data, it was demonstrated that the six-membered ring moiety in 2 adopts a boat
conformation. Since the exo-double bond does not affect the
conformation of six-membered ring, the six-membered ring
moieties in 1 and 2 should share the same conformation, which
was consistent with the deduction from the ROESY analysis of
1. Based on the X-ray data comparison of 2 and 3, however, the
existence of an endo-double bond in six-membered ring
moiety in 3 could contribute to the conformational change,
and lead the six-membered ring moiety in 3 to be in a halfchair conformation.
The structures of compounds 4, 5, 6, and 7 were identified
as isochaetoglobosin D (4) [6], chaetoglobosin G (5) [15],
cytoglobosin B (6) [6], and cytoglobosin C (7) [6], respectively, by comparing their HRESIMS and NMR data with those
reported in the literature.

Compounds 27 were examined for growth-inhibition

activity in vitro against human colon carcinoma HCT-116 cell.
Chaetoglobosin E (3), isochaetoglobosin D (4), chaetoglobosin
G (5), cytoglobosin C (7) showed cytotoxicity against the
HCT-116 cell line with IC50 values of 13.52 1.90, 14.36
1.81, 21.89 2.41, and 11.32 1.00 M, respectively. The
IC50 value of the positive control (doxorubicin) was 0.045
0.006 M. In previous reports, chaetoglobosins exhibited
cytotoxicity against many human cancer lines, such as K562
[17], P388 [18], BC1[19], Cholangiocarcinoma [19], KB, K562,
MCF-7, and HepG2 [2]. In this research, the bioassay showed
that chaetoglobosins also have the cytotoxicity against human
colon carcinoma HCT-116 cell.
Conict of interest
There are no possible conflicts of interest.
Acknowledgments
This project was supported financially by grants
from the Ministry of Science and Technology of China
(2012ZX09301002-003), the National Natural Science
Foundation of China (81373306, 81202441), the Guangdong
Natural Science Funds for Distinguished Young Scholar
(S2013050014287), the program for New Century Excellent
Talents in University (NCET-10-0120) from the Ministry of
Education of China.
References
[1] Scherlach K, Boettger D, Remme N, Hertweck C. The chemistry and
biology of cytochalasans. Nat Prod Rep 2010;27:86986.
[2] Zhang J, Ge HM, Jiao RH, Li J, Peng H, Wang YR, et al. Cytotoxic
chaetoglobosins from the endophyte Chaetomium globosum. Planta
Med 2010;76:19104.
[3] Ding G, Wang HL, Li L, Chen AJ, Chen L, Chen H, et al. Trichoderones A
and B: two pentacyclic cytochalasans from the plant endophytic fungus
Trichoderma gamsii. Eur J Org Chem 2012;2012:25169.
[4] Zhang DW, Ge HL, Xie D, Chen RD, Zou JH, Tao XY, et al. Periconiasins
AC, new cytotoxic cytochalasans with an unprecedented 9/6/5
tricyclic ring system from endophytic fungus Periconia sp. Org Lett
2013;15:16747.
[5] Xue M, Zhang Q, GaoJM Li H, Tian JM, Pescitelli G. Chaetoglobosin Vb
from endophytic Chaetomium globosum: absolute configuration of
chaetoglobosins. Chirality 2012;24:66874.

Fig. 3. The ORTEP drawing of the asymmetric units of Chaetoglobosins Fex (2) and E (3).

Q.-C. Zheng et al. / Fitoterapia 93 (2014) 126131

[6] Cui CM, Li XM, Li CS, Proksch P, Wang BG. Cytoglobosins AG,
cytochalasans from a marine-derived endophytic fungus, Chaetomium
globosum QEN-14. J Nat Prod 2010;73:72933.
[7] Dou H, Song YX, Liu XQ, Gong W, Li EG, Tan RX, et al. Chaetoglobosin fex
from the marine-derived endophytic fungus inhibits induction of
inflammatory mediators via toll-like receptor 4 signaling in macrophages. Biol Pharm Bull 2011;34:186473.
[8] He JW, Chen GD, Gao H, Yang F, Li XX, Peng T, et al. Heptaketides
with antiviral activity from three endolichenic fungal strains
Nigrospora sp., Alternaria sp. and Phialophora sp. Fitoterapia
2012;83:108791.
[9] Chen GD, Li YJ, Gao H, Chen Y, Li XX, Li J, et al. New azaphilones and
chlorinated phenolic glycosides from Chaetomium elatum with caspase-3
inhibitory activity. Planta Med 2012;78:16839.
[10] Yang F, Chen GD, Gao H, Li XX, Wu Y, Guo LD, et al. Two new naphthalene
derivatives from an endolichenic fungal strain Scopulariopsis sp. J Asian
Nat Prod Res 2012;14:105963.
[11] Chen GD, Chen Y, Gao H, Shen LQ, Wu Y, Li XX, et al. Xanthoquinodins
from an endolichenic fungal strain Chaetomium elatum. J Nat Prod
2013;76:7029.
[12] Zheng QC, Chen GD, Kong MZ, Cui JY, Li XX, Wu ZY, et al.
Nodulisporisteriods A and B, the first 3,4-seco-4-methyl-progesteroids
from Nodulisporium sp. Steroids 2013;78:896901.

131

[13] Ye F, Chen GD, He JW, Li XX, Sun X, Guo LD, et al. Xinshengin, the first
altenusin with tetracyclic skeleton core from Phialophora spp. Tetrahedron
Lett 2013;54:45514.
[14] Oikawa H, Murakami Y, Ichihara A. 20-Ketoreductase activity of
chaetoglobosin A and prochaetoglobosins in a cell-free system of
Chaetomium subaffine and the isolation of new chaetoglobosins. Biosci
Biotechnol Biochem 1993;57:62831.
[15] Sekita S, Yoshihira K, Natori S. Chaetoglobosins, cytotoxic 10-(indol-3-yl)[13] cytochalasans from Chaetomium spp. IV. 13C-nuclear magnetic
resonance spectra and their application to a biosynthetic study. Chem
Pharm Bull 1983;31:4908.
[16] Silverton JV, Akiyama T, Kabuto C. X-ray analysis of chaetoglobosin A an
indol-3-yl-[13]cytochalasan from Chaetomium globosum. Tetrahedron
Lett 1976;17:134950.
[17] Ko H, Kim BY, Ahn S, Oh WK, Kim J, Lee HS, et al. Chaetoglobosin A, an
inhibitor of Bleb formation on K562 cells induced by phorbol 12,13dibutyrate. J Microbiol Biotechnol 1998;8:7059.
[18] Iwamoto C, Yamada T, Ito Y, Minoura K, Numata A. Cytotoxic cytochalasans
from a Penicillium species separated from a marine alga. Tetrahedron
2001;57:29973004.
[19] Thohinung S, Kanokmedhakul S, Kanokmedhakul K, Kukongviriyapan V,
Tusskorn O, Soytong K. Cytotoxic 10-(indol-3-yl)-[13]cytochalasans from
the fungus Chaetomium elatum ChE01. Arch Pharm Res 2010;33:113541.