毛华菊中倍半萜内酯类化学成分研究

doi:10.6023/cjoc202102029

有机化学 ›› 2021, Vol. 41 ›› Issue (7): 2898-2904.DOI: 10.6023/cjoc202102029 上一篇下一篇

研究简报

毛华菊中倍半萜内酯类化学成分研究

刘文琪^a, 佘嘉祎^a, 杨英^a, 朱世明^a^,^b, 熊校勤^a^,^b, 谭芬^a^,^b, 张洪权^a^,^b^,^*(), 杨新洲^c^,^*(), 曾国平^a^,^b^,^*()

a 湖北第二师范学院化学与生命科学学院武汉 430205
b 植物抗癌活性物质提纯与应用湖北省重点实验室武汉 430205
c 中南民族大学药学院武汉 430074

收稿日期:2021-02-17 修回日期:2021-03-26 发布日期:2021-04-25
通讯作者: 张洪权, 杨新洲, 曾国平
作者简介:
† 共同第一作者(These authors contributed equally to this work).
基金资助:
国家自然科学基金(21602052); 国家自然科学基金(81903115); 湖北省教育厅科学技术研究(B2019178); 湖北省大学生创新创业训练计划(S202014099006)

Sesquiterpene Lactones fromDendranthema vestitum(Hemsl.) Ling

Wenqi Liu^a, Jiayi She^a, Ying Yang^a, Shiming Zhu^a^,^b, Xiaoqin Xiong^a^,^b, Fen Tan^a^,^b, Hongquan Zhang^a^,^b(), Xinzhou Yang^c(), Guoping Zeng^a^,^b()

a Department of Chemistry and Life Science, Hubei University of Education, Wuhan 430205
b Hubei Key Laboratory of Purification and Application of Plant Anti-cancer Active Ingredients, Wuhan 430205
c College of Pharmacy, South-Central University for Nationalities, Wuhan 430074

Received:2021-02-17 Revised:2021-03-26 Published:2021-04-25
Contact: Hongquan Zhang, Xinzhou Yang, Guoping Zeng
Supported by:
National Natural Science Foundation of China(21602052); National Natural Science Foundation of China(81903115); Science Research Project of Hubei Provincial Department of Education(B2019178); Undergraduate Innovation and Entreoreneurship Training Progam of Hubei Province(S202014099006)

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摘要/Abstract

采用溶剂提取法, Diaion HP-20、Sephadex LH-20葡聚糖凝胶、硅胶及制备高效液相等色谱方法, 对毛华菊的化学成分进行分离纯化, 并利用现代波谱技术对已分离得到的化合物进行结构鉴定. 从毛华菊的氯仿部位分离得到4个新化合物, 其结构类型属于愈创木内酯衍生物, 分别命名为(1S,5R,6S,7S,10S)-愈创木-3,11(13)-二烯-2-酮-12,6-内酯(1)、(1S,5R,6R,7R,8S,10S)-8-异丁酰氧基-愈创木-3,11(13)-二烯-2-酮-12,6-内酯(2)、(1S,5R,6R,7R,8S,10S)-8-(2'-甲基)丁酰氧基-愈创木-3,11(13)-二烯-2-酮-12,6-内酯(3)和(1R,5R,6R,7R,8S,10S,11S)-8-乙酰氧基-愈创木-3-烯-2-酮-12,6-内酯(4), 以及2个已知化合物matricarin (5)和11,13-dehydromatricarin (6).

关键词: 毛华菊, 倍半萜内酯, 愈创木内酯

The chemical constituents fromDendranthema vestitum(Hemsl.) Ling were isolated and purified by solvent extraction, Diaion HP-20, Sephadex LH-20, silica gel and preparative high performance liquid chromatography. Their structures were elucidated based on their spectroscopic data. Four new compounds which belong to guaianolide, named as (1S,5R,6S, 7S,10S)-2-oxo-guaia-3,11(13)-dien-12,6-olide (1), (1S,5R,6R,7R,8S,10S)-2-oxo-8-isobutyryloxy-guaia-3,11(13)-dien-12,6-oli- de (2), (1S,5R,6R,7R,8S,10S)-2-oxo-8-(2'-methyl)butyryloxy-guaia-3,11(13)-dien-12,6-olide (3) and (1R,5R,6R,7R,8S,10S, 11S)-2-oxo-8-acetoxy-guaia-3-en-12,6-olide (4) together with two known compounds matricarin (5) and 11,13-dehydromatricarin (6) were isolated from chloroform extract ofDendranthema vestitum(Hemsl.) Ling.

Key words: Dendranthema vestitum(Hemsl.) Ling, sesquiterpene lactones, guaianolide

引用此文

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.

Wenqi Liu, Jiayi She, Ying Yang, Shiming Zhu, Xiaoqin Xiong, Fen Tan, Hongquan Zhang, Xinzhou Yang, Guoping Zeng. Sesquiterpene Lactones fromDendranthema vestitum(Hemsl.) Ling[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2898-2904.

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参考文献 15

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No.	1		2
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	2.73 dd (7.2, 4.0)	53.5 (CH)	2.78 dd (7.0, 3.8)	53.5 (CH)
2		209.0 (C)		207.9 (C)
3	6.07 br s	132.3 (CH)	6.07 br s	132.4 (CH)
4		178.8 (C)		178.2 (C)
5	3.18~3.22 m	53.2 (CH)	3.14~3.20 m overlap	52.6 (CH)
6	4.36 dd (10.8, 9.6)	82.4 (CH)	4.34 dd (11.2, 9.6)	78.6 (CH)
7	2.63~2.71 m overlap	47.4 (CH)	3.12~3.16 m overlap	49.0 (CH)
8α	2.07~2.13 m	24.6 (CH₂)
8β	1.52~1.62 m		5.15 ddd (10.2, 9.6, 4.4)	71.5 (CH)
9α	1.69~1.77 m	34.2 (CH₂)	1.66~1.69 m	40.0 (CH₂)
9β	1.98~2.04 m		2.21 ddd (14.0, 6.4, 4.4)
10	2.63~2.71 m overlap	34.3 (CH)	2.55~2.65 m overlap	30.5 (CH)
11		138.6 (C)		135.7 (C)
12		169.8 (C)		168.9 (C)
13	6.28 d (3.4), 5.58 d (3.4)	120.7 (CH₂)	6.33 d (3.2), 5.83 d (3.2)	124.7 (CH₂)
14	0.75 d (7.2)	15.1 (CH₃)	0.97 d (7.6)	17.0 (CH₃)
15	2.31 br s	19.4 (CH₃)	2.32 br s	19.8 (CH₃)
16				175.8 (C)
17			2.55~2.65 m overlap	34.2 (CH)
18			1.21 d (6.6)	18.6 (CH₃)
19			1.23 d (6.6)	19.2 (CH₃)
No.	3		4
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	2.78 dd (6.8, 4.0)	53.5 (CH)	1.94 dd (10.8, 5.6)	55.9 (CH)
2		207.8 (C)		205.6 (C)
3	6.07 br s	132.4 (CH)	5.94 br s	131.5 (CH)
4		178.2 (C)		173.0 (C)
5	3.12~3.20 m overlap	52.6 (CH)	2.85 dd (10.4, 5.6)	51.3 (CH)
6	4.34 dd (10.4, 9.6)	78.5 (CH)	3.95 t (10.4)	83.1 (CH)
7	3.12~3.20 m overlap	48.9 (CH)	2.50~2.58 m	40.7 (CH)
8	5.16 ddd (10.0, 9.6, 4.4)	71.6 (CH)	5.06 td (10.4, 2.4)	69.1 (CH)
9α	1.66~1.77 m overlap	40.0 (CH₂)	2.03~2.09 m	44.0 (CH₂)
9β	2.23 ddd (14.0, 6.4, 4.4)		1.78 dt (14.4, 2.4)
10	2.55~2.63 m	30.4 (CH)	2.11~2.20 m overlap	28.3 (CH)
11		135.7 (C)	2.11~2.20 m overlap	59.5 (CH)
12		168.9 (C)		177.5 (C)
13	6.33 d (3.4), 5.83 d (3.4)	124.7 (CH₂)	1.35 d (6.8)	15.1 (CH₃)
14	0.98 d (7.6)	17.1 (CH₃)	1.38 d (6.4)	21.7 (CH₃)
15	2.32 br s	19.8 (CH₃)	2.27 br s	19.8 (CH₃)
16		175.6 (C)		169.7 (C)
17	2.39~2.48 m	41.0 (CH)	2.10 s	21.2 (CH₃)
18	1.18 d (7.2)	16.2 (CH₃)
19	1.66~1.77 m overlap, 1.49~1.60 m	27.0 (CH₂)
20	0.95 t (7.6)	11.5 (CH₃)

No.	1		2
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	2.73 dd (7.2, 4.0)	53.5 (CH)	2.78 dd (7.0, 3.8)	53.5 (CH)
2		209.0 (C)		207.9 (C)
3	6.07 br s	132.3 (CH)	6.07 br s	132.4 (CH)
4		178.8 (C)		178.2 (C)
5	3.18~3.22 m	53.2 (CH)	3.14~3.20 m overlap	52.6 (CH)
6	4.36 dd (10.8, 9.6)	82.4 (CH)	4.34 dd (11.2, 9.6)	78.6 (CH)
7	2.63~2.71 m overlap	47.4 (CH)	3.12~3.16 m overlap	49.0 (CH)
8α	2.07~2.13 m	24.6 (CH₂)
8β	1.52~1.62 m		5.15 ddd (10.2, 9.6, 4.4)	71.5 (CH)
9α	1.69~1.77 m	34.2 (CH₂)	1.66~1.69 m	40.0 (CH₂)
9β	1.98~2.04 m		2.21 ddd (14.0, 6.4, 4.4)
10	2.63~2.71 m overlap	34.3 (CH)	2.55~2.65 m overlap	30.5 (CH)
11		138.6 (C)		135.7 (C)
12		169.8 (C)		168.9 (C)
13	6.28 d (3.4), 5.58 d (3.4)	120.7 (CH₂)	6.33 d (3.2), 5.83 d (3.2)	124.7 (CH₂)
14	0.75 d (7.2)	15.1 (CH₃)	0.97 d (7.6)	17.0 (CH₃)
15	2.31 br s	19.4 (CH₃)	2.32 br s	19.8 (CH₃)
16				175.8 (C)
17			2.55~2.65 m overlap	34.2 (CH)
18			1.21 d (6.6)	18.6 (CH₃)
19			1.23 d (6.6)	19.2 (CH₃)
No.	3		4
No.	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C
1	2.78 dd (6.8, 4.0)	53.5 (CH)	1.94 dd (10.8, 5.6)	55.9 (CH)
2		207.8 (C)		205.6 (C)
3	6.07 br s	132.4 (CH)	5.94 br s	131.5 (CH)
4		178.2 (C)		173.0 (C)
5	3.12~3.20 m overlap	52.6 (CH)	2.85 dd (10.4, 5.6)	51.3 (CH)
6	4.34 dd (10.4, 9.6)	78.5 (CH)	3.95 t (10.4)	83.1 (CH)
7	3.12~3.20 m overlap	48.9 (CH)	2.50~2.58 m	40.7 (CH)
8	5.16 ddd (10.0, 9.6, 4.4)	71.6 (CH)	5.06 td (10.4, 2.4)	69.1 (CH)
9α	1.66~1.77 m overlap	40.0 (CH₂)	2.03~2.09 m	44.0 (CH₂)
9β	2.23 ddd (14.0, 6.4, 4.4)		1.78 dt (14.4, 2.4)
10	2.55~2.63 m	30.4 (CH)	2.11~2.20 m overlap	28.3 (CH)
11		135.7 (C)	2.11~2.20 m overlap	59.5 (CH)
12		168.9 (C)		177.5 (C)
13	6.33 d (3.4), 5.83 d (3.4)	124.7 (CH₂)	1.35 d (6.8)	15.1 (CH₃)
14	0.98 d (7.6)	17.1 (CH₃)	1.38 d (6.4)	21.7 (CH₃)
15	2.32 br s	19.8 (CH₃)	2.27 br s	19.8 (CH₃)
16		175.6 (C)		169.7 (C)
17	2.39~2.48 m	41.0 (CH)	2.10 s	21.2 (CH₃)
18	1.18 d (7.2)	16.2 (CH₃)
19	1.66~1.77 m overlap, 1.49~1.60 m	27.0 (CH₂)
20	0.95 t (7.6)	11.5 (CH₃)

毛华菊中倍半萜内酯类化学成分研究

Sesquiterpene Lactones fromDendranthema vestitum(Hemsl.) Ling

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参考文献 15

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