Sesquiterpene Lactones fromDendranthema vestitum(Hemsl.) Ling

doi:10.6023/cjoc202102029

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2898-2904.DOI: 10.6023/cjoc202102029 Previous Articles Next Articles

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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Abstract

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

Cite this article

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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Fig. & Tab. 5

References 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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