A New Monoterpene-Phenylpropanoid from Illicium difengpi

doi:10.6023/cjoc202208033

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1591-1595.DOI: 10.6023/cjoc202208033 Previous Articles Next Articles

NOTES

地枫皮中一个新的单萜杂合苯丙素成分

宁德生^a, 符毓夏^a, 李连春^a, 邹芷琪^a^,^b, 潘争红^a^,^*()

a 广西壮族自治区中国科学院广西植物研究所广西植物功能物质与资源持续利用重点实验室广西桂林 541006
b 广西中医药大学药学院南宁 530200

收稿日期:2022-08-24 修回日期:2022-10-17 发布日期:2022-11-15
通讯作者: 潘争红
基金资助:
国家自然科学基金(31960091); 广西创新驱动发展专项(桂科AA18118015); 广西自然科学基金(2018 GXNSFBA281094); 桂林市创新平台和人才计划(20210102-3)

A New Monoterpene-Phenylpropanoid from Illicium difengpi

Desheng Ning^a, Yuxia Fu^a, Lianchun Li^a, Zhiqi Zou^a^,^b, Zhenghong Pan^a()

a Guangxi Key Laboratory of Plant Functional Phytochemicals and Sustainable Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy Sciences, Guilin, Guangxi 541006
b College of Pharmacy, Guangxi University of Chinese Medicine, Nanning 530200

Received:2022-08-24 Revised:2022-10-17 Published:2022-11-15
Contact: Zhenghong Pan
Supported by:
National Natural Science Foundation of China(31960091); Guangxi Innovation-driven Development Special Project(Guike AA18118015); Natural Science Foundation of Guangxi Province(2018 GXNSFBA281094); Guilin Innovation Platform and Talent Plant(20210102-3)

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Abstract

Four compounds were isolated from the dichloromethane extract of stem bark of Illicium difengpi by using various column chromatographic methods. Their structures were identified as difengpienol D (1), (E)-3,4-methylenedioxophenyl propenal (2), dihydrocubebin (3) and pestalotiopyrone G (4) respectively by mass spectrometry (MS), infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), etc. and quantum chemical calculation method. Compound 1 was an unusual new compound formed by acyclic monoterpenoid and phenylpropanoid through C—C chain, and was also the first monoterpene-phenylpropanoid isolated from the genus Illicium. It showed weak anti-inflammatory activity.

Key words: Illicium difengpi, monoterpene-phenylpropanoid, structural identification, absolute configuration

Cite this article

Desheng Ning, Yuxia Fu, Lianchun Li, Zhiqi Zou, Zhenghong Pan. A New Monoterpene-Phenylpropanoid from Illicium difengpi[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1591-1595.

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Fig. & Tab. 6

References 18

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No.	δ_H (J in Hz)	δ_C	No.	δ_H (J in Hz)	δ_C
1		155.2	1'	4.99, dd, 1.5, 17.0 4.96, dd, 1.5, 17.0	111.1
2		133.6	2'	6.29, dd, 10.5, 17.0	148.4
3	6.94, d, 2.0	129.6	3'		44.8
4		131.5	4'	2.05, ddd, 5.5, 10.5, 14.5 1.76, ddd, 6.0, 10.5, 14.5	35.7
5	6.82, dd, 2.0, 8.0	128.1	5'	1.28~1.36, m	31.3
6	6.63, d. 8.0	117.1	6'	3.89, t, 6.5	77.7
7	3.23, d, 6.5	40.7	7'		148.6
8	5.91, ddt, 6.5, 10.5, 17.0	139.8	8'	4.85, br s 4.77, br s	111.7
9	4.98, dd, 1.5, 10.5 4.97, dd, 1.5, 17.0	115.2	9'	1.62, s	17.3
			10'	1.41, s	24.6

No.	δ_H (J in Hz)	δ_C	No.	δ_H (J in Hz)	δ_C
1		155.2	1'	4.99, dd, 1.5, 17.0 4.96, dd, 1.5, 17.0	111.1
2		133.6	2'	6.29, dd, 10.5, 17.0	148.4
3	6.94, d, 2.0	129.6	3'		44.8
4		131.5	4'	2.05, ddd, 5.5, 10.5, 14.5 1.76, ddd, 6.0, 10.5, 14.5	35.7
5	6.82, dd, 2.0, 8.0	128.1	5'	1.28~1.36, m	31.3
6	6.63, d. 8.0	117.1	6'	3.89, t, 6.5	77.7
7	3.23, d, 6.5	40.7	7'		148.6
8	5.91, ddt, 6.5, 10.5, 17.0	139.8	8'	4.85, br s 4.77, br s	111.7
9	4.98, dd, 1.5, 10.5 4.97, dd, 1.5, 17.0	115.2	9'	1.62, s	17.3
			10'	1.41, s	24.6

地枫皮中一个新的单萜杂合苯丙素成分

A New Monoterpene-Phenylpropanoid from Illicium difengpi

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