连翘果实中的三个新化合物

doi:10.6023/cjoc202012003

有机化学 ›› 2021, Vol. 41 ›› Issue (6): 2496-2501.DOI: 10.6023/cjoc202012003 上一篇下一篇

研究简报

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)

文章分享

1. 212496S.pdf(8118KB)

摘要/Abstract

利用大孔吸附树脂柱色谱、Sephdex LH-20凝胶柱色谱以及半制备高效液相色谱等技术, 从连翘果实的乙醇提取物中分离得到三个新的化合物, 包括两个苯乙醇苷类衍生物forsyside A (1), forsyside B (2)以及一个倍半萜forsysacid A (3). 通过UV, IR, HRESIMS, 一维NMR和二维NMR等波谱数据鉴定了它们的立体结构. 化合物1和3的绝对构型通过比较实验和计算圆二色谱的方法进行了确定, 化合物2的绝对构型通过激子手性法进行了确定. 此外, 对所有化合物的肝保护活性进行了研究, 其中化合物2在10 μmol•L ^–1浓度下对N-乙酰基-对氨基苯酚(APAP)引起的肝细胞损伤表现出较强的抑制作用.

关键词: 连翘, 苯乙醇苷衍生物, 倍半萜, 肝保护活性

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

引用此文

张旭, 邵思远, 冯子明, 姜建双, 杨桠楠, 张培成. 连翘果实中的三个新化合物[J]. 有机化学, 2021, 41(6): 2496-2501.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 8

参考文献 19

[1]	Editing Group for The Compilation of Chinese Herbal Medicines The Compilation of Chinese Herbal Medicines, Peopleʼs Medical Publishing House, Beijing, 1996, pp.429~430(in Chinese).
	(全国中草药汇编编写组, 全国中草药汇编, 人民卫生出版社, 北京, 1996, pp.429~430.)
[2]	Wang, F. N.; Ma, Z. Q.; Liu, Y.; Guo, Y. Z.; Gu, Z. W. Molecules 2009, 14,1324.
[3]	Shao, S. Y.; Zhang, F.; Feng, Z. M.; Yang, Y. N.; Jiang, J. S.; Zhang, P. C. Tetrahedron 2017, 73,6262.
[4]	Kuo, P. C.; Chen, G. F.; Yang, M. L.; Lin, Y. H.; Peng, C. C. BioMed. Res. Int. 2014,304830.
[5]	Piao, X. L.; Jang, M. H.; Cui, J.; Piao, X. S. Bioorg. Med. Chem. Lett. 2008, 18,1980.
[6]	Wei, Q.; Zhang, R.; Wang, Q.; Yan, X. J.; Yu, Q. W.; Yan, F. X.; Li, C.; Pei, Y. H. Nat. Prod. Res. 2020, 34,1320.
[7]	Xue, J.; Xie, L.; Liu, B. R.; Yu, L. X. Chin. J. Nat. Med. 2010, 8,414.
[8]	Yan, X. J.; Wen, J.; Xiang, Z.; Cai, D.; Lv, C. N.; Zhao, Y.; Qu, Z. Y.; Liu, Y. J.; Qu, J. L. J. Asian Nat. Prod. Res. 2017, 19,254.
[9]	Jiang, W. L.; Fu, F. H.; Xu, B. M.; Tian, J. W.; Zhu, H. B.; Hou, J. Phytomedicine 2010, 17,635.
[10]	Yang, L. L.; Zhou, X. J.; Huang, W. J.; Fang, Q.; Hu, J. L.; Yu, L. Z.; Ma, N.; Zhang, W. Q. Cell Physiol. Biochem. 2017, 43,2074.
[11]	Zhang, S.; Shao, S. Y.; Song, X. Y.; Xia, C. Y.; Yang, Y. N.; Zhang, P. C.; Chen, N. H. NeuroToxicology 2016, 52,72.
[12]	Han, X.; Piao, X. S.; Zhang, H. Y.; Li, P. F.; Yi, J. Q.; Zhang, Q.; Li, P. Asian-Australas. J. Anim. Sci. 2012, 25,569.
[13]	Yan, X. J.; Chen, T. G.; Zhang, L. W.; Du, H. Z. Eur. J. Pharmacol. 2017, 810,141.
[14]	Fan, X. B.; Li, W. X.; Chen, B. H.; Xiong, Z. Y.; Duan, J. M. J. Clin. Hepatol. 2013, 29,503(in Chinese).
	(范晓彬, 李文星, 陈炳合, 熊泽翼, 段吉明, 临床肝胆病杂志, 2013, 29,503.)
[15]	Pan, C. W.; Zhou, G. Y.; Chen, W. L.; Zhuge, L.; Jin, L. X.; Zheng, Y.; Lin, W.; Pan, Z. Z. Int. Immunopharmacol. 2015, 26,80.
[16]	Li, C; Dai, Y.; Zhang, S. X.; Duan, Y. H.; Liu, M. L.; Chen, L. Y.; Yao, X. S. Phytochemistry 2014, 104,105.
[17]	Yang, Y. N.; Han, B.; Yang, P. F.; Feng, Z. M.; Jiang, J. S., Zhang, P. C. Org. Chem. Front. 2019, 6,886.
[18]	Wu, T. S.; Yeh, J. H.; Wu, P. L. Phytochemistry 1995, 40,121.
[19]	Matsuda, N.; Sato, H.; Yaoita, Y.; Kikuchi, M. Chem. Pharm. Bull. 1996, 44,1122.

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

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 8

参考文献 19

相关文章 15

编辑推荐

相关统计

本文评价

[1]	吴秀蓉, 肖朝江, 沈怡, 汤红霞, 朱俊逸, 姜北. 植物来源抗疟倍半萜类天然产物研究(1972~2022)[J]. 有机化学, 2023, 43(8): 2764-2789.
[2]	余章昕, 蒙玉琴, 薛萌琳, 李小宝, 陈光英, 韩长日. 裸花紫珠叶中两个新的半日花烷型二萜[J]. 有机化学, 2023, 43(7): 2567-2571.
[3]	荀稳, 蒋丽清, 陈晓蕾, 吴静纯, 梁飞燕, 邓懿楠, 许波. 具有avarane骨架结构的Dysidea属海绵来源的倍半萜醌/氢醌类天然产物的合成研究进展[J]. 有机化学, 2023, 43(12): 4188-4212.
[4]	刘绪, 苏盼杰, 崔文博, 张宗萍, 陈晓涵, 王儒月, 费冬青, 张占欣. 栗色鼠尾草中一个新的吉马烷型倍半萜内酯类化合物[J]. 有机化学, 2022, 42(7): 2243-2247.
[5]	肖检, 彭羽, 李卫东. 倍半萜生物碱Dendrobine的全合成研究进展[J]. 有机化学, 2021, 41(7): 2636-2649.
[6]	刘文琪, 佘嘉祎, 杨英, 朱世明, 熊校勤, 谭芬, 张洪权, 杨新洲, 曾国平. 毛华菊中倍半萜内酯类化学成分研究[J]. 有机化学, 2021, 41(7): 2898-2904.
[7]	李洪涛, 谢飞, 孙岳, 王萌, 陈静圆, 周皓, 丁中涛. 蜜环菌YUD17010中一个新的原伊鲁烷型倍半萜芳基酯[J]. 有机化学, 2021, 41(11): 4493-4497.
[8]	李健, 何龙, 周志强, 甄艳霞, 谢卫青. Anislactone类倍半萜的合成研究进展[J]. 有机化学, 2020, 40(10): 3166-3176.
[9]	李竣, 徐晓诗, 滕海达, 陈玉, 梅之南, 杨光忠. 小连翘化学成分的研究[J]. 有机化学, 2019, 39(12): 3583-3587.
[10]	成蕾, 刘贵园, 潘胤池, 张茂生, 肖世基. 南鹤虱中两个新的倍半萜类化合物[J]. 有机化学, 2018, 38(7): 1829-1832.
[11]	黄超, 唐宇, 黄婷, 王立军, 江维, 麻光磊, 熊娟, 胡金锋. 姜黄中两个新没药烷型倍半萜成分的研究[J]. 有机化学, 2018, 38(6): 1562-1565.
[12]	熊维艳, 赵迎春, 徐亮, 季红. 海洋天然产物呋喃二倍半萜(18S)-variabilin的全合成[J]. 有机化学, 2017, 37(8): 2101-2108.
[13]	杨宁宁, 孔凡栋, 马青云, 黄圣卓, 罗都强, 周丽曼, 戴好富, 郁志芳, 赵友兴. 多形炭角菌Xylaria polymorpha菌丝发酵的次级代谢产物研究[J]. 有机化学, 2017, 37(4): 1033-1039.
[14]	李林斌, 沈洋, 张延东. Jiadifenolide的合成研究进展[J]. 有机化学, 2016, 36(3): 439-446.
[15]	卢勇平, 祁伟鹏, 翁国栋, 张兴贤. 愈创木烷型倍半萜类天然产物及其类似物的全合成研究进展[J]. 有机化学, 2015, 35(7): 1407-1413.