Chem. J. Chinese Universities ›› 2023, Vol. 44 ›› Issue (4): 20220678.doi: 10.7503/cjcu20220678
• Analytical Chemistry • Previous Articles Next Articles
SUN Zhiheng1, LIU Guiying2, WANG Bingzi1, CHEN Yifu1, FENG Yuezhu1, JIN Yongri1, LI Xuwen1()
Received:
2022-10-18
Online:
2023-04-10
Published:
2022-12-10
Contact:
LI Xuwen
E-mail:xwli@jlu.edu.cn
Supported by:
CLC Number:
TrendMD:
SUN Zhiheng, LIU Guiying, WANG Bingzi, CHEN Yifu, FENG Yuezhu, JIN Yongri, LI Xuwen. Two New Holostane-type Glycosides from Apostichopus Japonicus Selenka[J]. Chem. J. Chinese Universities, 2023, 44(4): 20220678.
Position | δC | δH mult.(J in Hz) | Position | δC | δH mult.(J in Hz) | ||
---|---|---|---|---|---|---|---|
Aglycone | 1 | 36.16 | 1.32m, 1.37m | Xyl | 1 | 105.46 | 4.64d(7.2) |
2 | 27.36 | 1.84m, 2.04m | 2 | 83.76 | 3.94m | ||
3 | 89.18 | 3.17dd(4.2, 12.0) | 3 | 76.06 | 4.14m | ||
4 | 39.79 | ― | 4 | 77.44 | 4.22m | ||
5 | 48.54 | 0.91m | 5 | 64.39 | 3.56m, 4.33m | ||
6 | 23.48 | 1.93m | Qui | 1 | 105.80 | 5.04d(7.2) | |
7 | 122.04 | 5.57m | 2 | 76.70 | 3.92m | ||
8 | 144.20 | ― | 3 | 75.68 | 3.98m | ||
9 | 47.29 | 3.58m | 4 | 86.07 | 3.54m | ||
10 | 35.96 | ― | 5 | 71.97 | 3.65m | ||
11 | 22.65 | 1.41m, 1.72m | 6 | 18.20 | 1.62d(6.0) | ||
12 | 29.80 | 1.98m, 2.12m | Xyl | 1 | 105.37 | 4.74d(7.8) | |
13 | 56.81 | ― | 2 | 73.67 | 3.88m | ||
14 | 45.91 | ― | 3 | 87.58 | 4.06m | ||
15 | 52.16 | 2.36d(15.6), 2.56d(16.2) | 4 | 69.24 | 3.93m | ||
16 | 213.10 | ― | 5 | 66.72 | 3.52m, 4.09m | ||
17 | 63.74 | 2.73s | MeGlc | 1 | 105.65 | 5.21d(7.8) | |
18 | 178.79 | ― | 2 | 75.27 | 3.88m | ||
19 | 24.29 | 1.13s | 3 | 88.21 | 3.61m | ||
20 | 83.49 | ― | 4 | 70.74 | 3.99m | ||
21 | 26.38 | 1.32s | 5 | 78.48 | 3.87m | ||
22 | 38.62 | 1.56m, 1.69m | 6 | 62.61 | 4.21m, 4.44m | ||
23 | 22.65 | 1.41m, 1.72m | OMe | 60.96 | 3.75s | ||
24 | 38.17 | 1.88m | Glc | 1 | 103.59 | 4.92d(7.8) | |
25 | 145.74 | ― | 2 | 74.49 | 3.92m | ||
26 | 110.68 | 4.67s | 3 | 78.33 | 4.12m | ||
27 | 22.44 | 1.58s | 4 | 71.72 | 4.08m | ||
28 | 17.52 | 1.04s | 5 | 78.96 | 3.89m | ||
29 | 28.88 | 1.19s | 6 | 62.31 | 4.13m, 4.37m | ||
30 | 32.14 | 1.07s |
Table 1 13C NMR and 1H NMR data of compound 1(in C5D5N, 150/600 MHz)
Position | δC | δH mult.(J in Hz) | Position | δC | δH mult.(J in Hz) | ||
---|---|---|---|---|---|---|---|
Aglycone | 1 | 36.16 | 1.32m, 1.37m | Xyl | 1 | 105.46 | 4.64d(7.2) |
2 | 27.36 | 1.84m, 2.04m | 2 | 83.76 | 3.94m | ||
3 | 89.18 | 3.17dd(4.2, 12.0) | 3 | 76.06 | 4.14m | ||
4 | 39.79 | ― | 4 | 77.44 | 4.22m | ||
5 | 48.54 | 0.91m | 5 | 64.39 | 3.56m, 4.33m | ||
6 | 23.48 | 1.93m | Qui | 1 | 105.80 | 5.04d(7.2) | |
7 | 122.04 | 5.57m | 2 | 76.70 | 3.92m | ||
8 | 144.20 | ― | 3 | 75.68 | 3.98m | ||
9 | 47.29 | 3.58m | 4 | 86.07 | 3.54m | ||
10 | 35.96 | ― | 5 | 71.97 | 3.65m | ||
11 | 22.65 | 1.41m, 1.72m | 6 | 18.20 | 1.62d(6.0) | ||
12 | 29.80 | 1.98m, 2.12m | Xyl | 1 | 105.37 | 4.74d(7.8) | |
13 | 56.81 | ― | 2 | 73.67 | 3.88m | ||
14 | 45.91 | ― | 3 | 87.58 | 4.06m | ||
15 | 52.16 | 2.36d(15.6), 2.56d(16.2) | 4 | 69.24 | 3.93m | ||
16 | 213.10 | ― | 5 | 66.72 | 3.52m, 4.09m | ||
17 | 63.74 | 2.73s | MeGlc | 1 | 105.65 | 5.21d(7.8) | |
18 | 178.79 | ― | 2 | 75.27 | 3.88m | ||
19 | 24.29 | 1.13s | 3 | 88.21 | 3.61m | ||
20 | 83.49 | ― | 4 | 70.74 | 3.99m | ||
21 | 26.38 | 1.32s | 5 | 78.48 | 3.87m | ||
22 | 38.62 | 1.56m, 1.69m | 6 | 62.61 | 4.21m, 4.44m | ||
23 | 22.65 | 1.41m, 1.72m | OMe | 60.96 | 3.75s | ||
24 | 38.17 | 1.88m | Glc | 1 | 103.59 | 4.92d(7.8) | |
25 | 145.74 | ― | 2 | 74.49 | 3.92m | ||
26 | 110.68 | 4.67s | 3 | 78.33 | 4.12m | ||
27 | 22.44 | 1.58s | 4 | 71.72 | 4.08m | ||
28 | 17.52 | 1.04s | 5 | 78.96 | 3.89m | ||
29 | 28.88 | 1.19s | 6 | 62.31 | 4.13m, 4.37m | ||
30 | 32.14 | 1.07s |
Position | δC | δH mult.(J in Hz) | Position | δC | δH mult.(J in Hz) | ||
---|---|---|---|---|---|---|---|
Aglycone | 1 | 36.14 | 1.31m, 1.36m | Xyl | 4 | 77.73 | 4.16m |
2 | 27.32 | 1.82m, 2.02m | 5 | 64.18 | 3.55m, 4.31m | ||
3 | 88.92 | 3.16dd(4.2, 12.0) | Glc | 1 | 105.65 | 5.14d(7.8) | |
4 | 39.67 | ― | 2 | 76.87 | 3.72m | ||
5 | 48.51 | 0.86m | 3 | 75.78 | 4.14m | ||
6 | 23.44 | 1.84m | 4 | 80.44 | 4.24m | ||
7 | 122.00 | 5.57m | 5 | 78.48 | 3.83m | ||
8 | 144.17 | ― | 6 | 61.27 | 3.75m | ||
9 | 47.27 | 3.56m | Xyl | 1 | 105.10 | 4.99d(7.8) | |
10 | 35.93 | ― | 2 | 73.84 | 3.90m | ||
11 | 22.65 | 1.41m, 1.72m | 3 | 87.69 | 3.98m | ||
12 | 29.79 | 1.96m, 2.12m | 4 | 69.25 | 3.92m | ||
13 | 56.80 | ― | 5 | 66.71 | 3.46m, 4.06m | ||
14 | 45.89 | ― | MeGlc | 1 | 106.04 | 5.20d(7.8) | |
15 | 52.14 | 2.34d(16.2), 2.54d(16.2) | 2 | 75.71 | 3.96m | ||
16 | 213.09 | ― | 3 | 88.42 | 4.12m | ||
17 | 63.73 | 2.72s | 4 | 70.74 | 4.00m | ||
18 | 178.79 | ― | 5 | 78.35 | 4.11m | ||
19 | 24.24 | 1.09s | 6 | 62.32 | 4.13m, 4.36m | ||
20 | 83.31 | ― | OMe | 60.97 | 3.75s | ||
21 | 26.38 | 1.31s | Glc | 1 | 103.03 | 4.88d(7.8) | |
22 | 38.61 | 1.55m, 1.68m | 2 | 73.38 | 3.92m | ||
23 | 22.65 | 1.41m, 1.72m | 3 | 88.23 | 3.61m | ||
24 | 38.17 | 1.87m | 4 | 69.85 | 3.98m | ||
25 | 145.75 | ― | 5 | 78.48 | 3.83m | ||
26 | 110.68 | 4.66s | 6 | 62.22 | 4.11m, 4.36m | ||
27 | 22.45 | 1.57s | Glc | 1 | 105.94 | 5.20d(7.8) | |
28 | 17.56 | 1.00s | 2 | 75.27 | 3.88m | ||
29 | 28.96 | 1.12s | 3 | 75.78 | 4.09m | ||
30 | 32.12 | 1.04s | 4 | 71.72 | 4.06m | ||
Xyl | 1 | 105.48 | 4.64d(7.2) | 5 | 78.81 | 3.91m | |
2 | 83.50 | 4.02m | 6 | 62.60 | 4.18m, 4.44m | ||
3 | 76.80 | 3.94m |
Table 2 13C NMR and 1H NMR data of compound 2(in C5D5N, 150/600 MHz)
Position | δC | δH mult.(J in Hz) | Position | δC | δH mult.(J in Hz) | ||
---|---|---|---|---|---|---|---|
Aglycone | 1 | 36.14 | 1.31m, 1.36m | Xyl | 4 | 77.73 | 4.16m |
2 | 27.32 | 1.82m, 2.02m | 5 | 64.18 | 3.55m, 4.31m | ||
3 | 88.92 | 3.16dd(4.2, 12.0) | Glc | 1 | 105.65 | 5.14d(7.8) | |
4 | 39.67 | ― | 2 | 76.87 | 3.72m | ||
5 | 48.51 | 0.86m | 3 | 75.78 | 4.14m | ||
6 | 23.44 | 1.84m | 4 | 80.44 | 4.24m | ||
7 | 122.00 | 5.57m | 5 | 78.48 | 3.83m | ||
8 | 144.17 | ― | 6 | 61.27 | 3.75m | ||
9 | 47.27 | 3.56m | Xyl | 1 | 105.10 | 4.99d(7.8) | |
10 | 35.93 | ― | 2 | 73.84 | 3.90m | ||
11 | 22.65 | 1.41m, 1.72m | 3 | 87.69 | 3.98m | ||
12 | 29.79 | 1.96m, 2.12m | 4 | 69.25 | 3.92m | ||
13 | 56.80 | ― | 5 | 66.71 | 3.46m, 4.06m | ||
14 | 45.89 | ― | MeGlc | 1 | 106.04 | 5.20d(7.8) | |
15 | 52.14 | 2.34d(16.2), 2.54d(16.2) | 2 | 75.71 | 3.96m | ||
16 | 213.09 | ― | 3 | 88.42 | 4.12m | ||
17 | 63.73 | 2.72s | 4 | 70.74 | 4.00m | ||
18 | 178.79 | ― | 5 | 78.35 | 4.11m | ||
19 | 24.24 | 1.09s | 6 | 62.32 | 4.13m, 4.36m | ||
20 | 83.31 | ― | OMe | 60.97 | 3.75s | ||
21 | 26.38 | 1.31s | Glc | 1 | 103.03 | 4.88d(7.8) | |
22 | 38.61 | 1.55m, 1.68m | 2 | 73.38 | 3.92m | ||
23 | 22.65 | 1.41m, 1.72m | 3 | 88.23 | 3.61m | ||
24 | 38.17 | 1.87m | 4 | 69.85 | 3.98m | ||
25 | 145.75 | ― | 5 | 78.48 | 3.83m | ||
26 | 110.68 | 4.66s | 6 | 62.22 | 4.11m, 4.36m | ||
27 | 22.45 | 1.57s | Glc | 1 | 105.94 | 5.20d(7.8) | |
28 | 17.56 | 1.00s | 2 | 75.27 | 3.88m | ||
29 | 28.96 | 1.12s | 3 | 75.78 | 4.09m | ||
30 | 32.12 | 1.04s | 4 | 71.72 | 4.06m | ||
Xyl | 1 | 105.48 | 4.64d(7.2) | 5 | 78.81 | 3.91m | |
2 | 83.50 | 4.02m | 6 | 62.60 | 4.18m, 4.44m | ||
3 | 76.80 | 3.94m |
Compound | IC50/(μmol·L-1) | |
---|---|---|
MDA⁃MB⁃231 | HepG2 | |
Holotoxin A1 | 3.840 | 8.593 |
Holotoxin B1 | 6.453 | 18.860 |
Holotoxin E | 2.386 | 5.909 |
Cladoloside B | 4.115 | 10.290 |
Holotoxin E1 | 4.686 | 14.260 |
Table 3 IC50 values of compounds inhibiting cancer cells
Compound | IC50/(μmol·L-1) | |
---|---|---|
MDA⁃MB⁃231 | HepG2 | |
Holotoxin A1 | 3.840 | 8.593 |
Holotoxin B1 | 6.453 | 18.860 |
Holotoxin E | 2.386 | 5.909 |
Cladoloside B | 4.115 | 10.290 |
Holotoxin E1 | 4.686 | 14.260 |
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