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SUPPLEMENTARY MATERIAL
A new benzyl ester and ergosterol derivatives from the fungus
Gymnoascus reessii
Sasiwimon Kitchawalita, Kwanjai Kanokmedhakula, Somdej
Kanokmedhakula,* and Kasem Soytongb
a
Natural Products Research Unit, Department of Chemistry, and Center of Excellence
for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen
40002, Thailand
b
Department of Plant Production Technology, Faculty of Agricultural Technology, King
Mongkut’s Institute of Technology Ladkrabang, Bangkok 10520, Thailand
*Corresponding author
E-mail address: somdej@kku.ac.th
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A new benzyl ester and ergosterol derivatives from the fungus
Gymnoascus reessii
A new benzyl ester, reessiate (1), anthraquinone, islandicin (2), ergosterol
and seven ergosterol derivatives (3-9) were isolated from the fungus
Gymnoascus reessii. All structures were identified by spectroscopic
methods.
This is the first report of their isolation from this fungus.
Compounds 4, 5, 6, 7 and 9 exhibited antimalarial activity against
Plasmodium falciparum with IC50 values in the range of 3.3-4.5 g/ml. In
addition, 4 showed cytotoxicity against KB, MCF7 and NCI-H187 cancer
cell lines. It was found that 4 has cytotoxic effect to MCF7 (IC50 = 7.9
g/ml) lower than Doxorubicin (IC50 = 8.5 g/ml).
Keywords: Gymnoascus reessii, benzyl ester, ergosterol derivative,
antimalaria, cytotoxicity
Table
Table S1: 1H (400 MHz) and 13C (100 MHz) NMR spectroscopic data (δ, ppm) for
compound 1 in CDCl3.
Spectra
Figure S1: Mass spectrum of 1.
Figure S2: IR spectrum of 1.
Figure S3: 1H-NMR spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S3a: expansion of 1H-NMR spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S4: 13C-NMR spectrum of 1 recorded in CDCl3 at 100 MHz.
Figure S5: DEPT spectrum of 1 recorded in CDCl3 at 100 MHz.
Figure S6: HMQC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S7: HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S7a: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S7b: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S7c: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S7d: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S8: NOESY spectrum of 1 recorded in CDCl3 at 400 MHz.
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Figure S8a: expansion of NOESY spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S8b: expansion of NOESY spectrum of 1 recorded in CDCl3 at 400 MHz.
Table S1: 1H (400 MHz) and 13C (100 MHz) NMR spectroscopic data (δ, ppm) for
compound 1 in CDCl3.
Position
1
2
3
4
5
6
7
8
9
1´
2´
3´
4´
5´
6´
7´
8´
9´
10´
2-OH
3´-OH
δH
6.12 s
2.00 s
2.28 s
6.57 s
10.15 s
2.03 s
3.87 s
5.52 s
11.80 s
12.29 s
Figure S1: Mass spectrum of 1.
δC
103.7
163.3
109.3
160.1
111.0
139.6
7.7
24.4
171.5
137.8
112.6
162.8
114.5
163.9
105.9
193.0
7.3
56.0
63.4
HMBC
NOESY
1, 3, 4,8
8
2,3,4
1,5,6
5
1´, 2´ 4´, 5´,10´
2´,3´,4´
3´,4´,5´
5´
1´,2´,6´, 9
3
2´, 3´,4´
9´,10´
10´
6´
7´,6´
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Figure S2: IR spectrum of 1.
9
10

7
3-OH
2-OH

’

’
6


’
’
5
’


’
Figure S3: 1H-NMR spectrum of 1 recorded in CDCl3 at 400 MHz.

8
’

7
8 ’



’

’
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9

8
’
7
8

10


6

’

’
’
’
5
’


’
Figure S3a: expansion of 1H-NMR spectrum of 1 recorded in CDCl3 at 400 MHz.
6
5
7

’

2
3
9 5 4
’



’
’ ’ ’
13
6


’
l


’

2 3
4 ’
 

 

’ ’
’
10

’

9
8


’

’
1


’
Figure S4: C-NMR spectrum of 1 recorded in CDCl3 at 100 MHz.
’
7 8
 
’ ’
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Figure S5: DEPT spectrum of 1 recorded in CDCl3 at 100 MHz.
Figure S6: HMQC spectrum of 1 recorded in CDCl3 at 400 MHz.
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Figure S7: HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S7a: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
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Figure S7b: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S7c: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
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Figure S7d: expansion of HMBC spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S8: NOESY spectrum of 1 recorded in CDCl3 at 400 MHz.
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Figure S8a: expansion of NOESY spectrum of 1 recorded in CDCl3 at 400 MHz.
Figure S8b: expansion of NOESY spectrum of 1 recorded in CDCl3 at 400 MHz.
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