A New Prenylated Isoflavone from the Stems and Leaves of Trigonostemon howii

doi:10.6023/cjoc202008002

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1246-1250.DOI: 10.6023/cjoc202008002 Previous Articles Next Articles

NOTES

长序三宝木枝叶中一个新的异戊烯基异黄酮类化合物

付艳辉^a^,^b^,^c^,^d, 谢玉桐^a^,^b^,^c, 马箐伟^a^,^b^,^c, 蒋波^a^,^b^,^c, 谢澜^a^,^b^,^c, 乔泽华^a^,^b^,^c, 刘艳萍^a^,^b^,^c^,^d^,^*()

a 海南师范大学热带药用资源化学教育部重点实验室海口 571127
b 海南师范大学南药资源产业化关键技术研究海南省工程研究中心海口 571127
c 海南师范大学南药资源产业化关键技术研究海口市重点实验室海口 571127
d 中国药科大学天然药物活性组分与药效国家重点实验室南京 210009

收稿日期:2020-08-04 修回日期:2020-09-13 发布日期:2020-11-04
通讯作者: 刘艳萍
基金资助:
海南省重点研发计划(ZDYF2019049); 海南省自然科学基金(2019RC198); 国家自然科学基金(21662011); 国家自然科学基金(31660097); 国家自然科学基金(21967008); 国家自然科学基金(32070390); 国家自然科学基金(22067005); 海口市重点研发计划(2017050); 海口市重点研发计划(20020056)

A New Prenylated Isoflavone from the Stems and Leaves of Trigonostemon howii

Yanhui Fu^a^,^b^,^c^,^d, Yutong Xie^a^,^b^,^c, Qingwei Ma^a^,^b^,^c, Bo Jiang^a^,^b^,^c, Lan Xie^a^,^b^,^c, Zehua Qiao^a^,^b^,^c, Yanping Liu^a^,^b^,^c^,^d^,^*()

a Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571127
b Engineering Research Center for Industrialization of Southern Medicinal Plants Resources of Hainan province,Hainan Normal University, Haikou 571127
c Key Laboratory of Southern Medicinal Plants Resources of Haikou City, Hainan Normal University, Haikou 571127
d State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009

Received:2020-08-04 Revised:2020-09-13 Published:2020-11-04
Contact: Yanping Liu
About author:
* Corresponding author. E-mail: liuyanpinghs@163.com
Supported by:
Key Research and Development Project of Hainan Province(ZDYF2019049); Natural Science Foundation of Hainan Province(2019RC198); National Natural Science Foundation of China(21662011); National Natural Science Foundation of China(31660097); National Natural Science Foundation of China(21967008); National Natural Science Foundation of China(32070390); National Natural Science Foundation of China(22067005); Key Research and Development Project of Haikou City(2017050); Key Research and Development Project of Haikou City(20020056)

1. cjoc202008002辅助材料.pdf(1233KB)

Abstract

A new prenylated isoflavone, trigohowine (1), together with seven known isoflavones, was isolated from the stems and leaves of Trigonostemon howii. Their structures were established on the basis of extensive spectral analyses. All known compounds were isolated from the genus Trigonostemon for the first time. The antitumor activities of compounds 1~8were evaluated against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7 and SW480). The research results showed that compounds 1~8 exhibited obvious inhibitory effects with IC₅₀ values comparable to those of doxorubicin.

Key words: Trigonostemon, Trigonostemon howii, prenylated isoflavone, antitumor activities

Cite this article

Yanhui Fu, Yutong Xie, Qingwei Ma, Bo Jiang, Lan Xie, Zehua Qiao, Yanping Liu. A New Prenylated Isoflavone from the Stems and Leaves of Trigonostemon howii[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1246-1250.

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Fig. & Tab. 4

References 20

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Position	δ_H^a	δ_C^b
2	7.82 (s, 1H)	150.6 d
3		125.7 s
4		174.7 s
4a		112.9 s
5		158.7 s
6		119.4 s
7		162.2 s
8	6.69 (s, 1H)	95.5 d
8a		158.1 s
1'		126.0 s
2'	7.08 (d, J=1.8 Hz, 1H)	110.0 d
3'		147.6 s
4'		147.5 s
5'	6.86 (d, J=8.0 Hz, 1H)	108.3 d
6'	6.93 (dd, J=8.0, 1.8 Hz, 1H)	122.5 d
1''α	3.05 (dd, J=13.6, 3.8 Hz, 1H)	29.8 t
1''β	2.92 (dd, J=13.6, 8.9 Hz, 1H)
2''	4.27 (dd, J=8.9, 3.8 Hz, 1H)	75.6 d
3''		147.6 s
4''α	4.97 (s, 1H)	110.2 t
4''β	4.83 (s, 1H)
5''	1.85 (s, 3H)	18.0 q
5-OCH₃	3.91 (s, 3H)	62.2 q
7-OCH₃	3.93 (s, 3H)	56.1 q
3',4'-OCH₂O	5.98 (s, 2H)	101.1 t

Position	δ_H^a	δ_C^b
2	7.82 (s, 1H)	150.6 d
3		125.7 s
4		174.7 s
4a		112.9 s
5		158.7 s
6		119.4 s
7		162.2 s
8	6.69 (s, 1H)	95.5 d
8a		158.1 s
1'		126.0 s
2'	7.08 (d, J=1.8 Hz, 1H)	110.0 d
3'		147.6 s
4'		147.5 s
5'	6.86 (d, J=8.0 Hz, 1H)	108.3 d
6'	6.93 (dd, J=8.0, 1.8 Hz, 1H)	122.5 d
1''α	3.05 (dd, J=13.6, 3.8 Hz, 1H)	29.8 t
1''β	2.92 (dd, J=13.6, 8.9 Hz, 1H)
2''	4.27 (dd, J=8.9, 3.8 Hz, 1H)	75.6 d
3''		147.6 s
4''α	4.97 (s, 1H)	110.2 t
4''β	4.83 (s, 1H)
5''	1.85 (s, 3H)	18.0 q
5-OCH₃	3.91 (s, 3H)	62.2 q
7-OCH₃	3.93 (s, 3H)	56.1 q
3',4'-OCH₂O	5.98 (s, 2H)	101.1 t

Compd.	IC₅₀^b/(μmol?L^–1)
Compd.	HL-60	SMMC-7721	A-549	MCF-7	SW480
1	0.88±0.03	1.23±0.08	2.68±0.15	0.76±0.05	1.37±0.06
2	1.82±0.07	2.06±0.10	5.24±0.16	8.31±0.18	2.53±0.09
3	3.03±0.15	1.09±0.10	2.31±0.12	2.08±0.07	5.75±0.12
4	5.21±0.17	1.08±0.06	3.29±0.13	12.02±0.08	6.03±0.13
5	3.28±0.09	15.02±0.12	2.62±0.13	0.87± 0.05	8.39±0.16
6	0.92±0.05	3.48±0.14	6.49±0.12	4.86±0.13	3.18±0.09
7	3.58±0.07	4.35±0.11	18.37±0.16	9.28±0.19	6.26±0.10
8	1.86±0.05	11.24±0.22	6.45±0.11	2.56±0.08	7.42±0.13
Doxorubicin^c	0.36±0.06	0.85±0.09	2.12±0.11	1.32±0.10	5.58±0.16

Compd.	IC₅₀^b/(μmol?L^–1)
Compd.	HL-60	SMMC-7721	A-549	MCF-7	SW480
1	0.88±0.03	1.23±0.08	2.68±0.15	0.76±0.05	1.37±0.06
2	1.82±0.07	2.06±0.10	5.24±0.16	8.31±0.18	2.53±0.09
3	3.03±0.15	1.09±0.10	2.31±0.12	2.08±0.07	5.75±0.12
4	5.21±0.17	1.08±0.06	3.29±0.13	12.02±0.08	6.03±0.13
5	3.28±0.09	15.02±0.12	2.62±0.13	0.87± 0.05	8.39±0.16
6	0.92±0.05	3.48±0.14	6.49±0.12	4.86±0.13	3.18±0.09
7	3.58±0.07	4.35±0.11	18.37±0.16	9.28±0.19	6.26±0.10
8	1.86±0.05	11.24±0.22	6.45±0.11	2.56±0.08	7.42±0.13
Doxorubicin^c	0.36±0.06	0.85±0.09	2.12±0.11	1.32±0.10	5.58±0.16

长序三宝木枝叶中一个新的异戊烯基异黄酮类化合物

A New Prenylated Isoflavone from the Stems and Leaves of Trigonostemon howii

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