A new dimeric anthraquinone from endophytic Talaromyces sp ...
SUPPLEMENTARY MATERIAL
A new dimeric anthraquinone from endophytic Talaromyces sp. YE3016 Xiao-Song Xiea, Xiao-Wei Fanga, Rong Huangb, Shou-Peng Zhanga, HongXia Weia, and Shao-Hua Wua* a
Key Laboratory for Microbial Resources of the Ministry of Education, Yunnan Institute
of Microbiology, Yunnan University, Kunming 650091, PR China b
School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR
China
*Corresponding author. E-mail: [email protected]
A new unsymmetrical dimeric anthraquinone, 3-demethyl-3-(2-hydroxypropyl)skyrin (1) was isolated from the solid-state fermentation extract of an endophytic fungal strain Talaromyces sp. YE 3016, together with five known compounds, skyrin (2), oxyskyrin (3), emodin (4), 1,3,6-trihydroxy-8-methylanthraquinone (5), and ergosterol (6). The structure of the new compound was elucidated on the basis of spectroscopic analysis. Compounds 13 exhibited moderate cytotoxic activities against MCF-7 cell line. Keywords: Talaromyces sp.; endophytic fungi; dimeric anthraquinone; skyrin
List of contents Table S1. 1H and 13C NMR Data of compound 1 (500 and 125 MHz, respectively, CD3OD, δ in ppm, J in Hz). Figure S1. The 1H NMR spectrum of compound 1 Figure S2. The 13C NMR spectrum of compound 1 Figure S3. The HMQC spectrum of compound 1 Figure S4. The HMBC spectrum of compound 1 Figure S5. The 1H-1H COSY spectrum of compound 1
Table S1. 1H and 13C NMR Data of compound 1 (500 and 125 MHz, respectively, CD3OD, δ in ppm, J in Hz). position
13
C
1
1
163.0
-
1’
162.8
-
2
125.1
7.10 (1H, s)
2’
124.4
7.04 (1H, s)
3
150.5
-
3’
149.3
-
4
121.7
7.38 (1H, s)
4’
121.4
7.31 (1H, s)
4a, 4’a
133.2
-
5
128.0
-
5’
127.4
-
6, 6’
166.3
-
7
108.2
6.69 (1H, s)
7’
108.2
6.68 (1H, s)
8, 8’
165.4
-
8a, 8’a
110.9
-
9, 9’
191.9
-
9a, 9’a
115.1
-
10, 10’
184.0
-
10a, 10’a
135.0
-
H
11
46.4
2.72 (2H, d, 4.8)
11’
21.9
2.34 (3H, s)
12
68.8
3.96 (1H, m)
13
23.2
1.16 (3H, d, 6.1)
220 215 210 205 200 195 190 185 180 175 170 165 160 155 150 145 140 135 130 125 120 115 110 105 100
95
90
85
80
75
70
65
60
55
50
45
40
0.5
35
30
25
20
16.86
1.0
23.15 21.88
1.5
30.65
2.0 3.105
2.5 4.816
7.459
3.0
50.86 50.48 49.40 49.23 49.06 48.89 48.72 48.55 48.38 46.46
68.80
3.5 4.163
4.0
2.720
4.5
88.90
0.965
5.0
110.88 108.21
5.5
115.07
6.0
135.06 133.15 131.02 127.42 125.07 124.37 121.72 121.38
6.5
150.47 149.34
7.0
166.33 165.41 162.97 162.82
7.5
1.741
8.0 0.884 0.902
0.896 0.845
8.5
184.02
191.90
1.3068 1.1637 1.1516 0.9218 0.9077
2.4909 2.3448
2.7299 2.7202
3.3340 3.3318 3.3293
3.9719 3.9594
4.9205
6.6934 6.6874 6.6820
7.1025 7.0441
7.3854 7.3116
Figure S1. The 1H NMR spectrum of compound 1
0.0
15
ppm
Figure S2. The 13C NMR spectrum of compound 1
ppm
Figure S3. The HMQC spectrum of compound 1
ppm
30 40 50 60 70 80 90 100 110 120 130 140 7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
Figure S4. The HMBC spectrum of compound 1
ppm 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
ppm
Figure S5. The 1H-1H COSY spectrum of compound 1
ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
A new dimeric anthraquinone from endophytic Talaromyces sp. YE3016 Xiao-Song Xiea, Xiao-Wei Fanga, Rong Huangb, Shou-Peng Zhanga, HongXia Weia, and Shao-Hua Wua* a
Key Laboratory for Microbial Resources of the Ministry of Education, Yunnan Institute
of Microbiology, Yunnan University, Kunming 650091, PR China b
School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR
China
*Corresponding author. E-mail: [email protected]
A new unsymmetrical dimeric anthraquinone, 3-demethyl-3-(2-hydroxypropyl)skyrin (1) was isolated from the solid-state fermentation extract of an endophytic fungal strain Talaromyces sp. YE 3016, together with five known compounds, skyrin (2), oxyskyrin (3), emodin (4), 1,3,6-trihydroxy-8-methylanthraquinone (5), and ergosterol (6). The structure of the new compound was elucidated on the basis of spectroscopic analysis. Compounds 13 exhibited moderate cytotoxic activities against MCF-7 cell line. Keywords: Talaromyces sp.; endophytic fungi; dimeric anthraquinone; skyrin
List of contents Table S1. 1H and 13C NMR Data of compound 1 (500 and 125 MHz, respectively, CD3OD, δ in ppm, J in Hz). Figure S1. The 1H NMR spectrum of compound 1 Figure S2. The 13C NMR spectrum of compound 1 Figure S3. The HMQC spectrum of compound 1 Figure S4. The HMBC spectrum of compound 1 Figure S5. The 1H-1H COSY spectrum of compound 1
Table S1. 1H and 13C NMR Data of compound 1 (500 and 125 MHz, respectively, CD3OD, δ in ppm, J in Hz). position
13
C
1
1
163.0
-
1’
162.8
-
2
125.1
7.10 (1H, s)
2’
124.4
7.04 (1H, s)
3
150.5
-
3’
149.3
-
4
121.7
7.38 (1H, s)
4’
121.4
7.31 (1H, s)
4a, 4’a
133.2
-
5
128.0
-
5’
127.4
-
6, 6’
166.3
-
7
108.2
6.69 (1H, s)
7’
108.2
6.68 (1H, s)
8, 8’
165.4
-
8a, 8’a
110.9
-
9, 9’
191.9
-
9a, 9’a
115.1
-
10, 10’
184.0
-
10a, 10’a
135.0
-
H
11
46.4
2.72 (2H, d, 4.8)
11’
21.9
2.34 (3H, s)
12
68.8
3.96 (1H, m)
13
23.2
1.16 (3H, d, 6.1)
220 215 210 205 200 195 190 185 180 175 170 165 160 155 150 145 140 135 130 125 120 115 110 105 100
95
90
85
80
75
70
65
60
55
50
45
40
0.5
35
30
25
20
16.86
1.0
23.15 21.88
1.5
30.65
2.0 3.105
2.5 4.816
7.459
3.0
50.86 50.48 49.40 49.23 49.06 48.89 48.72 48.55 48.38 46.46
68.80
3.5 4.163
4.0
2.720
4.5
88.90
0.965
5.0
110.88 108.21
5.5
115.07
6.0
135.06 133.15 131.02 127.42 125.07 124.37 121.72 121.38
6.5
150.47 149.34
7.0
166.33 165.41 162.97 162.82
7.5
1.741
8.0 0.884 0.902
0.896 0.845
8.5
184.02
191.90
1.3068 1.1637 1.1516 0.9218 0.9077
2.4909 2.3448
2.7299 2.7202
3.3340 3.3318 3.3293
3.9719 3.9594
4.9205
6.6934 6.6874 6.6820
7.1025 7.0441
7.3854 7.3116
Figure S1. The 1H NMR spectrum of compound 1
0.0
15
ppm
Figure S2. The 13C NMR spectrum of compound 1
ppm
Figure S3. The HMQC spectrum of compound 1
ppm
30 40 50 60 70 80 90 100 110 120 130 140 7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
Figure S4. The HMBC spectrum of compound 1
ppm 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200 7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
ppm
Figure S5. The 1H-1H COSY spectrum of compound 1
ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
