A New Prenylated Isoflavone from the Stems of Harrisonia perforata

  • Zhangyang Shen ,
  • Yujie Li ,
  • Yimeng Zhao ,
  • Yayuan Deng ,
  • Yawen Guo ,
  • Yu Wang ,
  • Yanping Liu ,
  • Yanhui Fu
Expand
  • 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
†(The authors contributed equally to this work).
* Corresponding authors. E-mail: ;

Received date: 2022-07-04

  Revised date: 2022-08-09

  Online published: 2022-10-10

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)

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.

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 . DOI: 10.6023/cjoc202207005

References

[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.
[2]
Raksat, A.; Maneerat, W.; Andersen, R. J.; Pyne, S. G.; Laphook- hieo, S. J. Nat. Prod. 2018, 81, 1835.
[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.
[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.
[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.
[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)
[7]
( 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.
[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.
[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.
[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.
[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.
[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.
[15]
Choodej, S.; Sommit, D.; Pudhom, K. Bioorg. Med. Chem. Lett. 2013, 23, 3896.
[16]
Mayaka, R. K.; Langat, M. K.; Omolo, J. O.; Cheplogoi, P. K. Planta Med. 2012, 78, 383.
[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.
[18]
Yin, S.; Chen, X.; Su, Z. S.; Yang, S. P.; Fan, C. Q.; Ding, J.; Yue, J. M. Tetrahedron 2009, 65, 1147.
[19]
Tuntiwachwuttikul. P.; Phansa, P.; Pootaeng-On, Y.; Taylor, W. C. Chem. Pharm. Bull. 2006, 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.
[21]
Abdel-Kader, M. S.; Amer, M. E.; Tang, S.; Kingston, D. G. Nat. Prod. Res. 2006, 20, 922.
[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.
[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.
[27]
Wei, S. P.; Wu, W. J.; Ji, Z. Q. Int. J. Mol. Sci. 2012, 13, 7375.
[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.
[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.
[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.
Outlines

/