Nortriterpenoids from the fruit stalk of <i>Schisandra chinensis</i> (Turcz.) Baill.

Yan Liu; Xiaohui Rong; Yuanhang Chang; Juan Pan; Wei Guan; Haixue Kuang; Bingyou Yang

doi:10.2478/fzm-2022-0014

Nortriterpenoids from the fruit stalk of Schisandra chinensis (Turcz.) Baill.

doi: 10.2478/fzm-2022-0014

1.
Key Laboratory of Basic and Application Research of Beiyao (Heilongjiang University of Chinese Medicine), Ministry of Education, Harbin 150040, China
2.
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China

More Information

Corresponding author: Haixue Kuang, E-mail: hxkuang@yahoo.com; Bingyou Yang, E-mail: ybywater@163.com

摘要

Abstract: Objective The fruit stalk of Schisandra chinensis (Turcz.) Baill. (S. chinensis) has been found to contain bioactive components similar to the fruit of S. chinensis. Here, we report a recent discovery about new nortriterpenoids with a novel skeleton and anti-gastric cancer activity, which were isolated from the fruit stalk of S. chinensis. Methods The chemical components of ethyl acetate extract from 70% ethanol extract from S. chinensis fruit stalk were separated, purified, and identified by liquid chromatography methods (silica gel, ODS, HPLC) and extensive spectroscopic analyses (NMR, IR, UV, MS, CD). Results Two new nortriterpenoids, schilancitrilactone M and 25-hydroxyl schindilactone D (1 and 2), along with ten known nortriterpenoids (3-12) were isolated from the fruit stalk of S. chinensis. The isolated compounds were tested for their cytotoxic activities against MGC-803 cells, and the results showed that compounds 6-8 possessed significant activities with IC₅₀ of 9.01, 11.77, and 2.74 μmol/L, respectively. Conclusion Twelve nortriterpenoids including two new compounds were isolated from the fruit stalk of S. chinensis for the first time. Among them, compounds 6-8 showed significant anti-gastric cancer activities. We postulated that the fruit stalk of S. chinensis could be used as an anti-gastric cancer drug.
- nortriterpenoids /
- Schisandra chinensis (Turcz.) Baill. /
- fruit stalk, cytotoxicity /
- MGC-803 cells

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Figure 1. Structures of compounds 1-12 from Schisandra chinensis

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Figure 2. Key HMBC, ¹H-¹H COSY and ROESY of compounds 1-2

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S1. ¹H-NMR spectrum of compound 1

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S2. ¹³C-NMR spectrum of compound 1

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S3. DEPT 135 spectrum of compound 1

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S4. HSQC spectrum of compound 1

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S5. ¹H-¹H COSY spectrum of compound 1

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S6. HMBC spectrum of compound 1

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S7. ROESY spectrum of compound 1

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S8. HR-ESI-MS spectrum of compound 1

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S9. IR spectrum of compound 1

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S10. UV spectrum of compound 1

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S11. CD spectrum of compound 1

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S12. ¹H-NMR spectrum of compound 2

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S13. ¹³C-NMR spectrum of compound 2

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S14. DEPT 135 spectrum of compound 2

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S15. HSQC spectrum of compound 2

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S16. ¹H-¹H COSY spectrum of compound 2

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S17. HMBC spectrum of compound 2

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S18. ROESY spectrum of compound 2

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S19. HR-ESI-MS spectrum of compound 2

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S20. IR spectrum of compound 2

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S21. UV spectrum of compound 2

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Table 1. ¹H-NMR (400 MHz) and ¹³C-NMR (100 MHz) spectroscopic data for 1 (δ in ppm, J in Hz) in C₅D₅N

No	δ_C	δ_H(J in Hz)
1	87.1	4.42 (1H, s)
2	73.0	4.72 (1H, s)
3	176.6
4	85.3
5	60.5	2.44 (1H, dd, J=4.6, 12.2)
6	22.1	1.36-1.42 (2H, m)
7	24.9	1.95 (2H, m)
8	54.5	2.65(1H, m)
9	82.8
10	99.3
11	43.8	2.13 (1H, o)
		1.75 (1H, dd, J=8.4, 12.6)
12	50.9	2.70 (1H, o)
13	50.7
14	85.5	4.75 (1H, dd, J=6.0, 8.0)
15	173.5
16	46.3	2.85 (2H, o)
17	121.9
19	42.5	2.82 (1H, ABd, J=15.6)
		2.37 (1H, ABd, J=15.6)
20	36.5	3.52 (1H, m)
21	16.3	1.31 (3H, d, J=6.8)
22	114.3	5.59 (1H, d, J=9.8)
23	148.2
24	138.5	6.98 (1H, s)
25	129.6
26	170.8	6.98
27	10.4	1.83 (3H, s)
28	19.0	1.14 (3H, s)
29	22.2	1.03 (3H, s)
30	28.8	1.24 (3H, s)

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Table 2. ¹H-NMR (400 MHz) and ¹³C-NMR (100 MHz) spectroscopic data for 2 (δ in ppm, J in Hz) in C₅D₅N

No	δ_C	δ_H(J in Hz)
1	108.7
2	43.5	3.04(1H, ABd, J=17.8)
		3.13 (1H, ABd, J=17.8)
3	173.4
4	84.2
5	58.9	2.64 (1H, m)
6	36.4	2.26 (2H, m)
7	68.4	4.60 (1H, m)
8	60.2	2.93 (1H, d, J=9.8)
9	81.7
10	97.0
11	42.4	1.73 (1H, m)
		2.08 (1H, m)
12	31.2	1.59 (1H, m)
		1.84 (1H, m)
13	50.2
14	209.8
15	99.1
16	45.0	2.88 (1H, o)
17	220.4
18	26.0	0.93 (3H, s)
19	40.7	2.61 (1H, ABd, 16.3)
		2.83 (1H, ABd, 16.3)
20	44.6	2.75 (1H, dq, J=7.0, 12, 0)
21	14.9	1.05 (3H, d, J=7.0)
22	40.3	2.88 (1H, m)
23	75.1	5.30 (1H, br. s)
24	73.3	5.22 (1H, d, J=1.8)
25	76.7
26	177.7
27	17.6	1.71 (3H, s)
29	25.1	1.39 (3H, s)
30	29.5	1.26 (3H, s)

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Table 3. Cytotoxic activities of compounds 1-12 against MGC-803 cell lines

Drugs	IC₅₀(µmol/L)
compound 1	46.38 ± 3.92
compound 2	﹥50
compound 3	﹥50
compound 4	﹥50
compound 5	﹥50
compound 6	9.01 ± 3.72
compound 7	11.77 ± 2.61
compound 8	2.74 ± 0.58
compound 9	﹥50
compound 10	20.17 ± 3.12
compound 11	40.85 ± 3.65
compound 12	﹥50
cisplatin	3.79 ± 0.51
IC₅₀ was defined as the concentration that resulted in a 50% decrease in cell number, and the values were within the 0–1 000 μg/mL range. Results are presented as mean ± SD (N = 3 independent replicates). Cisplatin was used as a positive control.

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S1. ¹³C-NMR (100 MHz) spectroscopic data for compounds 3-12.

No.	3	4	5	6	7	8	9	10	11	12
1	109.0	108.7	108.8	108.2	81.6	81.7	81.4	79.8	79.5	87.3
2	43.1	43.6	43.1	44.0	35.1	35.5	35.4	35.9	35.4	73.7
3	173.7	173.6	173.4	173.2	175.2	174.6	175.5	176.0	175.5	177.2
4	84.6	84.1	84.6	83.8	84.0	83.9	83.8	84.6	84.2	85.8
5	58.0	58.9	58.3	58.5	58.2	58.3	58.4	62.4	62.2	58.7
6	37.0	36.3	36.6	23.6	36.6	36.9	36.4	24.3	23.9	29.3
7	69.9	68.2	68.8	135.2	68.0	68.8	67.8	27.6	27.2	25.8
8	59.6	60.2	60.5	138.0	60.6	59.7	60.2	56.9	56.6	57.6
9	83.6	81.6	81.7	82.0	81.5	79.7	81.5	83.1	82.6	70.6
10	97.5	97.0	97.4	96.4	95.9	96.1	95.7	99.0	98.4	100.6
11	43.4	42.4	41.5	39.6	41.0	42.9	41.8	39.1	38.6	38.0
12	32.8	31.2	30.4	31.4	30.3	32.5	31.0	26.3	25.8	34.6
13	50.4	50.2	49.9	50.6	49.8	50.4	50.2	27.0	26.5	93.0
14	215.1	209.9	209.5	198.8	45.6	53.7	45.0	216.8	216.5	53.4
15	101.2	98.8	98.1	99.3	98.3	101.1	99.1	99.9	99.4	81.9
16	53.7	45.1	45.8	45.6	209.1	214.7	209.5	31.4	30.9	30.7
17	220.0	220.4	221.6	220.3	221.6	221.9	220.4	35.6	35.2	53.0
18	28.0	26.0	26.0	26.4	25.9	28.0	26.0	29.2	28.8	24.0
19	40.2	40.6	40.8	40.7	42.6	41.8	42.6	71.6	70.9	49.8
20	46.3	44.8	33.2	44.6	41.2	46.1	40.2	33.3	31.8	35.9
21	15.6	15.0	12.4	14.9	12.4	15.6	14.8	20.0	19.5	12.0
22	46.3	40.3	41.2	40.3	33.2	46.3	44.6	76.0	78.9	87.0
23	80.1	75.5	75.0	74.9	74.6	83.6	73.2	84.0	79.1	81.2
24	151.3	69.4	71.7	72.6	75.6	151.4	75.0	149.2	34.0	147.1
25	131.5	42.1	42.2	77.0	76.9	131.5	76.7	130.8	34.8	130.4
26	174.6	178.0	177.8	177.7	177.2	175.9	177.5	175.7	181.4	174.4
27	10.8	8.0	7.9	18.1	17.5	10.9	17.5	11.2	16.6	10.8
29	25.4	25.0	25.4	24.7	27.8	27.9	27.8	22.4	22.0	24.3
30	30.0	29.4	29.8	29.0	21.0	21.0	20.9	29.0	28.6	30.1
OAC	-	-	-	-	-	-	-	-	-	169.9
-	-	-	-	-	-	-	-	-	-	21.6

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