A New Prenylated Isoflavone from the Stems of Harrisonia perforata

doi:10.6023/cjoc202207005

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 771-776.DOI: 10.6023/cjoc202207005 Previous Articles Next Articles

牛筋果茎中一个新的异戊烯基异黄酮类化合物

沈章阳^a,†, 李玉洁^a,†, 赵艺萌^a, 邓雅源^a, 郭亚文^a, 王俞^a, 刘艳萍^a^,^b^,^c^,^*(), 付艳辉^a^,^b^,^c^,^*()

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 海南师范大学海口市热带果蔬研究与开发重点实验室海口 571127

收稿日期:2022-07-04 修回日期:2022-08-09 发布日期:2022-10-10
作者简介:
†共同第一作者
基金资助:
海南省重点研发计划(ZDYF2022SHFZ028); 国家自然科学基金(22067005); 国家自然科学基金(32070390); 国家自然科学基金(21967008); 海南省自然科学基金(222RC655); 海南省自然科学基金(2019RC198); 海南省自然科学基金(220RC596); 海口市重点研发计划(2017050); 海口市重点研发计划(2020054)

A New Prenylated Isoflavone from the Stems of Harrisonia perforata

Zhangyang Shen^a,†, Yujie Li^a,†, Yimeng Zhao^a, Yayuan Deng^a, Yawen Guo^a, Yu Wang^a, Yanping Liu^a^,^b^,^c(), Yanhui Fu^a^,^b^,^c()

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 Research and Development of Tropical Fruits and Vegetables of Haikou City, Hainan Normal University, Haikou 571127

Received:2022-07-04 Revised:2022-08-09 Published:2022-10-10
Contact: *E-mail: liuyanpinghs@163.com;fuyanhui80@163.com
About author:
†(The authors contributed equally to this work).
Supported by:
Key Research and Development Project of Hainan Province(ZDYF2022SHFZ028); National Natural Science Foundation of China(22067005); National Natural Science Foundation of China(32070390); National Natural Science Foundation of China(21967008); National Natural Science Foundation of Hainan Province(222RC655); National Natural Science Foundation of Hainan Province(2019RC198); National Natural Science Foundation of Hainan Province(220RC596); Key Research and Development Project of Haikou City(2017050); Key Research and Development Project of Haikou City(2020054)

1. .pdf(427KB)

Abstract

A new prenylated isoflavone, harriperforine (1), as well as seven known analogues, was isolated and characterized from the stems of Harrisonia perforata. Their chemical structures were unambiguously elucidated based on spectroscopic analyses. All known compounds 2~8 were isolated from the genus Harrisonia for the first time. The growth inhibitory activities against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7 and SW480) of compounds 1~8 were evaluated. As a result, compounds 1~8 displayed remarkable inhibitory activities with IC₅₀ values ranging from (0.38±0.03) μmol/L to (31.68±0.21) μmol/L, which were comparable to those of cisplatin.

Key words: Harrisonia, H. perforata, prenylated isoflavone, tumor cell growth inhibitory activities

Cite this article

Zhangyang Shen, Yujie Li, Yimeng Zhao, Yayuan Deng, Yawen Guo, Yu Wang, Yanping Liu, Yanhui Fu. A New Prenylated Isoflavone from the Stems of Harrisonia perforata[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 771-776.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 31

[1]	Liu, Y. P.; Guo, J. M.; Yan, G.; Zhang, M. M.; Zhang, W. H.; Qiang, L.; Fu, Y. H. J. Agric. Food Chem. 2019, 67, 4817. doi: 10.1021/acs.jafc.9b00865
[2]	Raksat, A.; Maneerat, W.; Andersen, R. J.; Pyne, S. G.; Laphook- hieo, S. J. Nat. Prod. 2018, 81, 1835. doi: 10.1021/acs.jnatprod.8b00321
[3]	Liu, Y. P.; Sun, L. L.; Zhang, X. L.; Niu, H. Y.; Pan, Z. H.; Fu, Y. H. Nat. Prod. Res. 2020, 34, 2295. doi: 10.1080/14786419.2018.1536132
[4]	Miranda, C. L.; Stevens, J. F.; Ivanov, V.; McCall, M.; Frei, B.; Deinzer, M. L.; Buhler, D. R. J. Agric. Food Chem. 2000, 48, 3876. doi: 10.1021/jf0002995
[5]	Zhang, G. P.; Xiao, Z. Y.; Rafique, J.; Arfan, M.; Smith, P. J.; Lategan, C. A.; Hu, L. H. J. Nat. Prod. 2009, 72, 1265. doi: 10.1021/np900144c
[6]	Nguyen, P. H.; Sharma, G.; Dao, T. T.; Uddin, M. N.; Kang, K. W.; Ndinteh, D. T.; Mbafor, J. T.; Oh, W. K. Bioorg. Med. Chem. 2012, 20, 6459.
[7]	Flora Reipublicae Popularis Sinicae Editorial Board Flora Reipublicae Popularis Sinicae, Vol. 43(3), Science Press, Beijing, 1997, p. 15. (in Chinese)
	( 中国植物志编辑委员会, 中国植物志, 第43(3)卷, 科学出版社, 北京, 1997, p. 15.)
[8]	Tang, X. H.; Luo, R. C.; Ye, M. S.; Tang, H. Y.; Ma, Y. L.; Chen, Y. N.; Wang, X. M.; Lu, Q. Y.; Liu, S.; Li, X. N.; Yan, Y.; Yang, J.; Ran, X. Q.; Fang, X.; Zhou, Y.; Yao, Y. G.; Di, Y. T.; Hao, X. J. Org. Lett. 2021, 23, 262. doi: 10.1021/acs.orglett.0c03460
[9]	Liu, S.; Zhang, C. S.; Ran, X. Q.; Tang, X. H.; Guo, Y. R.; Yan, Y.; Yao, Y. G.; Hao, X. J.; Luo, R. C.; Di, Y. T. Org. Biomol. Chem. 2021, 9, 9637.
[10]	Sombatsri, A.; Sribuhom, T.; Phusrisom, S.; Kukongviriyapan, V.; Yenjai, C. Phytochem. Lett. 2021, 44, 110. doi: 10.1016/j.phytol.2021.06.010
[11]	Gui, P. Y.; Yan, X. H.; Yuan, W. J.; Ma, Y. L.; Ding, X.; Liu, S.; Di, Y. T.; Zhu, W. M.; Hao, X. J. Nat. Prod. Res. 2019, 33, 2830. doi: 10.1080/14786419.2018.1508139
[12]	Yan, X. H.; Yi, P.; Cao, P.; Yang, S. Y.; Fang, X.; Zhang, Y.; Wu, B.; Leng, Y.; Di, Y. T.; Lv, Y.; Hao, X. J. Sci. Rep. 2016, 6, 36927. doi: 10.1038/srep36927
[13]	Lv, C.; Yan, X. H.; Tu, Q.; Di, Y. T.; Yuan, C. M.; Fang, X.; Ben-David, Y.; Xia, L.; Gong, J. X.; Shen, Y. M.; Yang, Z.; Hao, X. J. Angew. Chem., Int. Ed. 2016, 55, 7539. doi: 10.1002/anie.201602783
[14]	Fang, X.; Di, Y. T.; Zhang, Y.; Xu, Z. P.; Lu, Y.; Chen, Q. Q.; Zheng, Q. T.; Hao. X. J. Angew. Chem., Int. Ed. 2015, 54, 5592. doi: 10.1002/anie.201412126
[15]	Choodej, S.; Sommit, D.; Pudhom, K. Bioorg. Med. Chem. Lett. 2013, 23, 3896. doi: 10.1016/j.bmcl.2013.04.064
[16]	Mayaka, R. K.; Langat, M. K.; Omolo, J. O.; Cheplogoi, P. K. Planta Med. 2012, 78, 383. doi: 10.1055/s-0031-1298143
[17]	Yan, X. H.; Di, Y. T.; Fang, X.; Yang, S. Y.; He, H. P.; Li, S. L.; Lu, Y.; Hao, X. J. Phytochemistry 2011, 72, 508. doi: 10.1016/j.phytochem.2011.01.010
[18]	Yin, S.; Chen, X.; Su, Z. S.; Yang, S. P.; Fan, C. Q.; Ding, J.; Yue, J. M. Tetrahedron 2009, 65, 1147. doi: 10.1016/j.tet.2008.11.068
[19]	Tuntiwachwuttikul. P.; Phansa, P.; Pootaeng-On, Y.; Taylor, W. C. Chem. Pharm. Bull. 2006, 54, 44. doi: 10.1248/cpb.54.44
[20]	Balde, A. M.; Apers, S.; De Bruyne, T. E.; Van den Heuvel, H.; Claeys, M.; Vlietinck, A. J.; Pieters, L. A. Planta Med. 2000, 66, 67. doi: 10.1055/s-2000-11120
[21]	Abdel-Kader, M. S.; Amer, M. E.; Tang, S.; Kingston, D. G. Nat. Prod. Res. 2006, 20, 922. pmid: 16854720
[22]	Tahara, S.; Ingham, J. L.; Mizutani, J. Agric. Biol. Chem. 1987, 51, 211.
[23]	Tahara, S.; Nakahara, S.; Mizutani, J.; Ingham, J. L. Agric. Biol. Chem. 1984, 48, 1471.
[24]	Wang, F.; Li, X. L.; Wei, G. Z.; Ren, F. C.; Liu, J. K. Nat. Prod. Bioprospect. 2013, 3, 238. doi: 10.1007/s13659-013-0062-3
[25]	Venzke, D.; Carvalho, F. K.; Ruani, A. P.; Oliveira, A. S.; Brighente, I. M. C.; Micke, G. A.; Barison, A.; Pizzolatti, M. G. J. Brazil. Chem. Soc. 2013, 24, 1991.
[26]	Yenesew, A.; Midiwo, J. O.; Waterman, P. G. Phytochemistry 1998, 47, 295. doi: 10.1016/S0031-9422(97)00424-X
[27]	Wei, S. P.; Wu, W. J.; Ji, Z. Q. Int. J. Mol. Sci. 2012, 13, 7375. doi: 10.3390/ijms13067375
[28]	Souza, R. F. D.; Marinho, V. H.; Silva, G. A. D.; Silva, J. K. R. D.; Bastos, G. N.; Arruda, A. C.; Silva, M. N. D.; Arruda, M. S. P. J. Brazil. Chem. Soc. 2013, 24, 1857.
[29]	Fu, Y. H.; Di, Y. T.; He, H. P.; Li, S. L.; Zhang, Y.; Hao, X. J. J. Nat. Prod. 2014, 77, 57. doi: 10.1021/np4005823
[30]	Ma, Y. L.; Liu, Y. P.; Zhang, C.; Zhao, W. H.; Shi, S.; He, D. N.; Zhang, P.; Liu, X. H.; Han, T. T.; Fu, Y. H. Bioorg. Chem. 2018, 76, 359. doi: 10.1016/j.bioorg.2017.12.016
[31]	Jiang, Z. H.; Liu Y. P.; Huang, Z. H.; Wang, T. T.; Feng, X. Y.; Yue, H.; Guo, W.; Fu, Y. H. Bioorg. Chem. 2017, 75, 260. doi: 10.1016/j.bioorg.2017.10.003

Position	δ_H^a	δ_C^b
2	7.86 (s, 1H)	152.7 d
3		123.4 s
4		180.9 s
4a		106.6 s
5		157.2 s
6		109.2 s
7		166.0 s
8	6.38 (s, 1H)	88.9 d
8a		158.2 s
1'		123.9 s
2'	7.10 (d, J=1.8 Hz, 1H)	115.1 d
3'		145.7 s
4'		146.8 s
5'	6.93 (d, J=8.0 Hz, 1H)	110.7 d
6'	7.06 (dd, J=8.0, 1.8 Hz, 1H)	121.0 d
1''α	3.21 (dd, J=15.6, 9.3 Hz, 1H)	26.8 t
1''β	3.12 (dd, J=15.6, 8.0 Hz, 1H)
2''	4.80 (dd, J=9.3, 8.0 Hz, 1H)	91.8 d
3''		71.9 s
4''	1.37 (s, 3H)	25.8 q
5''	1.25 (s, 3H)	23.9 q
5-OH	13.12 (s, 1H)
4'-OCH₃	3.93 (s, 3H)	56.0 q

Position	δ_H^a	δ_C^b
2	7.86 (s, 1H)	152.7 d
3		123.4 s
4		180.9 s
4a		106.6 s
5		157.2 s
6		109.2 s
7		166.0 s
8	6.38 (s, 1H)	88.9 d
8a		158.2 s
1'		123.9 s
2'	7.10 (d, J=1.8 Hz, 1H)	115.1 d
3'		145.7 s
4'		146.8 s
5'	6.93 (d, J=8.0 Hz, 1H)	110.7 d
6'	7.06 (dd, J=8.0, 1.8 Hz, 1H)	121.0 d
1''α	3.21 (dd, J=15.6, 9.3 Hz, 1H)	26.8 t
1''β	3.12 (dd, J=15.6, 8.0 Hz, 1H)
2''	4.80 (dd, J=9.3, 8.0 Hz, 1H)	91.8 d
3''		71.9 s
4''	1.37 (s, 3H)	25.8 q
5''	1.25 (s, 3H)	23.9 q
5-OH	13.12 (s, 1H)
4'-OCH₃	3.93 (s, 3H)	56.0 q

化合物	IC₅₀^b/(μmol•L^-1)
化合物	HL-60	SMMC-7721	A-549	MCF-7	SW480
1	0.56±0.05	0.48±0.06	0.67±0.04	1.08±0.07	0.38±0.03
2	3.21±0.10	0.82±0.05	7.32±0.17	1.89±0.11	5.43±0.12
3	6.58±0.16	12.45±0.20	4.32±0.13	1.68±0.06	0.89±0.04
4	0.89±0.05	9.42±0.12	6.89±0.11	2.89±0.09	5.85±0.10
5	4.32±0.08	31.68±0.21	1.68±0.09	0.57±0.04	13.79±0.15
6	10.35±0.12	6.67±0.09	3.26±0.08	11.83±0.13	0.71±0.05
7	2.75±0.06	8.47±0.08	14.79±0.13	10.42±0.15	8.53±0.09
8	0.62±0.03	15.68±0.16	4.25±0.07	6.58±0.06	2.09±0.08
顺铂^c	1.56±0.08	11.87±0.12	17.28±0.12	22.87±0.16	30.03±0.21

化合物	IC₅₀^b/(μmol•L^-1)
化合物	HL-60	SMMC-7721	A-549	MCF-7	SW480
1	0.56±0.05	0.48±0.06	0.67±0.04	1.08±0.07	0.38±0.03
2	3.21±0.10	0.82±0.05	7.32±0.17	1.89±0.11	5.43±0.12
3	6.58±0.16	12.45±0.20	4.32±0.13	1.68±0.06	0.89±0.04
4	0.89±0.05	9.42±0.12	6.89±0.11	2.89±0.09	5.85±0.10
5	4.32±0.08	31.68±0.21	1.68±0.09	0.57±0.04	13.79±0.15
6	10.35±0.12	6.67±0.09	3.26±0.08	11.83±0.13	0.71±0.05
7	2.75±0.06	8.47±0.08	14.79±0.13	10.42±0.15	8.53±0.09
8	0.62±0.03	15.68±0.16	4.25±0.07	6.58±0.06	2.09±0.08
顺铂^c	1.56±0.08	11.87±0.12	17.28±0.12	22.87±0.16	30.03±0.21

牛筋果茎中一个新的异戊烯基异黄酮类化合物

A New Prenylated Isoflavone from the Stems of Harrisonia perforata

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 31

Related Articles 1

Recommended Articles

Metrics

Comments