Three New Compounds from the Fruits of Forsythia suspensa

doi:10.6023/cjoc202012003

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2496-2501.DOI: 10.6023/cjoc202012003 Previous Articles Next Articles

NOTES

连翘果实中的三个新化合物

张旭, 邵思远, 冯子明, 姜建双, 杨桠楠^*(), 张培成^*()

中国医学科学院北京协和医学院药物研究所天然药物活性物质与功能国家重点实验室北京 100050

收稿日期:2020-12-01 修回日期:2021-01-13 发布日期:2021-03-04
通讯作者: 杨桠楠, 张培成
基金资助:
国家自然科学基金(81673313); 重大新药创制科技重大专项(2018ZX09711001-008)

Three New Compounds from the Fruits of Forsythia suspensa

Xu Zhang, Siyuan Shao, Ziming Feng, Jianshuang Jiang, Ya'nan Yang(), Peicheng Zhang()

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking UnionMedical College and Chinese Academy of Medical Sciences, Beijing 100050

Received:2020-12-01 Revised:2021-01-13 Published:2021-03-04
Contact: Ya'nan Yang, Peicheng Zhang
Supported by:
National Natural Science Foundation of China(81673313); Drug Innovation Major Project(2018ZX09711001-008)

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Abstract

Three new compounds including two phenylethanoid glycosides derivatives, forsyside A (1) and forsyside B (2), together with a sesquiterpene forsysacid A (3) were isolated from the EtOH extract of the fruits of Forsythia suspensa. Their structures were elucidated from analysis of UV, IR, HRESIMS, and 1D/2D NMR data. The absolute configurations of 1 and 3 were determined by quantum electronic circular dichroism (ECD) calculation, and compound 2 was determined by the ECD exciton chirality method. In addition, all compounds were evaluated for their hepatoprotective activity against N-acetyl-p- aminophenol-induced (APAP) HepG2 cell injury, and compound 2 showed significant activity at a concentration of 10 μmol• L ^–1.

Key words: Forsythia suspensa, phenylethanoid glycosides derivative, sesquiterpene, hepatoprotective activity

Cite this article

Xu Zhang, Siyuan Shao, Ziming Feng, Jianshuang Jiang, Ya'nan Yang, Peicheng Zhang. Three New Compounds from the Fruits of Forsythia suspensa[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2496-2501.

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Fig. & Tab. 8

References 19

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Position	δ_H (J in Hz)	δ_C	Position	δ_H (J in Hz)	δ_C
1		67.3	10'		126.7
2	6.89~6.97 (m)	153.2	11'	7.37 (brs)	110.9
3	5.98~6.01 (m)	126.3	12'		149.6
4		185.3	13'		150.8
5	5.98~6.01 (m)	126.3	14'	7.05 (d, 8.5)	114.3
6	6.89~6.97 (m)	153.2	15'	7.18 (brd, 8.5)	122.9
7	1.89 (t, 6.5)	39.8	16'	7.56 (d, 16.0)	144.9
8	3.45~3.50 (m), 3.73 (overlap)	64.0	17'	6.55 (d, 16.0)	115.2
1'		132.8	18'		166.6
2'	6.95 (brs)	110.9	1''	4.14 (d, 7.5)	102.8
3'		147.0	2''	2.92~2.97 (m)	73.3
4'		145.5	3''	3.14 (overlap)	76.4
5'	6.66 (d, 8.0)	114.7	4''	3.12 (overlap)	69.9
6'	6.73 (brd, 8.0)	119.0	5''	3.35~3.39 (m)	73.6
7'	4.68 (overlap)	70.9	6''	4.15~4.18 (m), 4.34~4.36 (m)	63.6
8'	4.36~4.40 (m)	83.7	3'-OCH₃	3.71 (s)	55.4
9'	3.54~3.58 (m), 3.22~3.27 (m)	60.1	12'-OCH₃	3.82 (s)	55.7

Position	δ_H (J in Hz)	δ_C	Position	δ_H (J in Hz)	δ_C
1		67.3	10'		126.7
2	6.89~6.97 (m)	153.2	11'	7.37 (brs)	110.9
3	5.98~6.01 (m)	126.3	12'		149.6
4		185.3	13'		150.8
5	5.98~6.01 (m)	126.3	14'	7.05 (d, 8.5)	114.3
6	6.89~6.97 (m)	153.2	15'	7.18 (brd, 8.5)	122.9
7	1.89 (t, 6.5)	39.8	16'	7.56 (d, 16.0)	144.9
8	3.45~3.50 (m), 3.73 (overlap)	64.0	17'	6.55 (d, 16.0)	115.2
1'		132.8	18'		166.6
2'	6.95 (brs)	110.9	1''	4.14 (d, 7.5)	102.8
3'		147.0	2''	2.92~2.97 (m)	73.3
4'		145.5	3''	3.14 (overlap)	76.4
5'	6.66 (d, 8.0)	114.7	4''	3.12 (overlap)	69.9
6'	6.73 (brd, 8.0)	119.0	5''	3.35~3.39 (m)	73.6
7'	4.68 (overlap)	70.9	6''	4.15~4.18 (m), 4.34~4.36 (m)	63.6
8'	4.36~4.40 (m)	83.7	3'-OCH₃	3.71 (s)	55.4
9'	3.54~3.58 (m), 3.22~3.27 (m)	60.1	12'-OCH₃	3.82 (s)	55.7

Position	δ_H (J in Hz)	δ_C	Position	δ_H (J in Hz)	δ_C
1		128.0	5'	7.11 (d, 8.5)	114.1
2	6.92 (d, 1.5)	112.4	6'	7.66 (dd, 8.5, 1.5)	122.8
3		147.6	7'		197.4
4		145.6	1''	5.01 (d, 7.5)	99.3
5	6.64 (d, 8.0)	115.5	2''	3.25 (overlap)	73.0
6	6.66 (dd, 8.0, 1.5)	120.4	3''	3.25 (overlap)	76.8
7	4.80 (dd, 9.5, 5.0)	54.0	4''	3.13~3.16 (m)	69.5
8	4.09 (t, 9.5), 3.51 (dd, 9.5, 5.0)	63.7	5''	3.33 (overlap)	77.1
1'		130.5	6''	3.64 (brd, 11.5), 3.43 (dd, 11.5, 5.5)	60.5
2'	7.50 (d, 1.5)	111.4	3-OCH₃	3.72 (s)	55.6
3'		148.6	3'-OCH₃	3.79 (s)	55.5
4'		150.4

Position	δ_H (J in Hz)	δ_C	Position	δ_H (J in Hz)	δ_C
1		128.0	5'	7.11 (d, 8.5)	114.1
2	6.92 (d, 1.5)	112.4	6'	7.66 (dd, 8.5, 1.5)	122.8
3		147.6	7'		197.4
4		145.6	1''	5.01 (d, 7.5)	99.3
5	6.64 (d, 8.0)	115.5	2''	3.25 (overlap)	73.0
6	6.66 (dd, 8.0, 1.5)	120.4	3''	3.25 (overlap)	76.8
7	4.80 (dd, 9.5, 5.0)	54.0	4''	3.13~3.16 (m)	69.5
8	4.09 (t, 9.5), 3.51 (dd, 9.5, 5.0)	63.7	5''	3.33 (overlap)	77.1
1'		130.5	6''	3.64 (brd, 11.5), 3.43 (dd, 11.5, 5.5)	60.5
2'	7.50 (d, 1.5)	111.4	3-OCH₃	3.72 (s)	55.6
3'		148.6	3'-OCH₃	3.79 (s)	55.5
4'		150.4

Position	δ_H (J in Hz)	δ_C	Position	δ_H (J in Hz)	δ_C
1		167.2	4'	1.85 (dd, 14.0, 8.0), 1.49 (dd, 14.0, 10.0)	42.0
2	5.67 (s)	119.3	5'		85.8
3		147.9	7'	5.00 (s)	97.4
4	6.07 (d, 15.5)	132.5	8'		81.9
5	7.84 (d, 15.5)	129.9	3-Me	1.95 (s)	20.7
1'		56.1	1'-Me	0.88 (s)	11.2
2'	3.26 (d, 8.5)	76.0	5'-Me	1.06 (s)	19.7
3'	3.36~3.40 (m)	70.6

连翘果实中的三个新化合物

Three New Compounds from the Fruits of Forsythia suspensa

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