Chinese Journal of Organic Chemistry >
Diterpenoids with Cytotoxicity for Pancreatic Cancer SW1990 Cells from the Rhizomes of Euphorbia jolkinii Boiss
Received date: 2023-12-08
Revised date: 2024-01-29
Online published: 2024-03-05
Supported by
Applied Basic Research Programs of Yunnan Province(202201AU070166); Program of Yunling Scholarship(YNWR-YLXZ-2019-019); Scientific Research Fund of Yunnan Education Department(2023Y0455); Social Development Special Projects of Science and Technology Department of Yunnan Province(202303AC100025); Open Foundation of Yunnan Key Laboratory of Southern Medicine Utilization(202105AG070012XS23015)
The chemcal constituents of the rhizomes of Euphorbia jolkinii were studied by silica gel column, MCI column, Sephadex LH-20 column, and semi-preparative high performance liquid chromatography. Eight diterpenoids were identified by high resolution electrospray ionization mass spectroscopy (HR-ESI-MS), nuclear magnetic resonance (NMR), and caculated electrostatic circular dichroism (ECD) methods including two udescribed ent-abietane diterpenoids (1~2), four known ent-abietane diterpenoids (3~6), and two reported lathyrane diterpenoids (7~8). (7R,8S)-7,8-Dihydroxy-17-nor-ent-abieta- 13(14)-en-15-one (1) was a C(17)-nor-ent-abietane diterpenoid and 2 was a new ent-abietane diterpenoid lactone. Cytotoxic activity assays showed that compound 7 displayed obvious toxicity to pancreatic cancer SW1990 cells whose IC50 was (44.97±9.16) μmol/L. Moreover, it cound promote the preapoptosis of SW1990 cells in a dose-dependent manner, and played a role in inhibiting tumor cells by decreasing the expressions of the intracellular anti-apoptotic protein Bcl-2.
Hongbo Zhu , Ji Wang , Weiyan Hu , Tang Zhou , Zhiqi Lin , Rongping Zhang , Chang'an Geng , Xinglong Chen . Diterpenoids with Cytotoxicity for Pancreatic Cancer SW1990 Cells from the Rhizomes of Euphorbia jolkinii Boiss[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1929 -1937 . DOI: 10.6023/cjoc202312007
| [1] | Flora Reipublicae Popularis Sinicae Editorial Board, Flora Reipublicae Popularis Sinicae, Vol. 44(3), Science Press, 1997, p. 108. (in Chinese) |
| [1] | (中国植物志编辑委员会, 中国植物志, Vol. 44(3), 科学出版社, 1997, p. 108.) |
| [2] | Wu, Z.-K.; Zhou, T. Y.; Xiao, P. G. Outline of Xinhua Materia Medica, Vol. 2, Shanghai Scientific and Technical Publishers, 1991, p. 219. (in Chinese) |
| [2] | (吴征馈, 周太炎, 肖培根, 新华本草纲要, Vol. 2, 上海科学技术出版社, 1991, p. 219.) |
| [3] | Editorial Board of the National Pharmacopoeia, Chinese Pharmacopoeia, The Medicine Science and Technology Press of China, 2010 (in Chinese) |
| [3] | (国家药典编委会, 中华人民共和国药典, 中国医药科技出版社, 2010.) |
| [4] | Uemura, D.; Hirate, Y. Tetrahedron Lett. 1972, 13, 1387. |
| [5] | Huang, C.-S.; Luo, S. H.; Li, Y. L. Nat. Prod. Bioprospect. 2014, 4, 91. |
| [6] | Jia, H.-Y.; Liao, Z. X.; Liu, F. Y.; Wu, L.; Zuo, B. Nat. Prod. Res. 2015, 29, 650. |
| [7] | Song, N.-L.; Zheng, X.; Wang, J. P.; Zhu, L.; Ding, Z. T. Front. Chem. 2022, 912738. |
| [8] | Garg, S.-K.; Chari, S. T. Curr. Opin. Gastroenterol. 2020, 36, 456. |
| [9] | Chen, X.-L.; Geng, Y. J.; Li, F.; Hu, W. Y.; Zhang, R. P. J. Ethnopharmacol. 2022, 289, 115010. |
| [10] | Shi, Q.-W.; Su, X. H.; Kiyota, H. Chem. Rev. 2008, 108, 4295. |
| [11] | Liu, J.-H.; Latif, A.; Ali, M.; Zhang, G. P.; Hu, L. H. Phytochemistry 2012, 75, 153. |
| [12] | Yan, R.-Y.; Tan, Y. X.; Cui, X. Q.; Chen, R. Y.; Yu, D. Q. J. Nat. Prod. 2008, 71, 195. |
| [13] | Yu, C.-C.; Hsieh, C. R.; Hsiao, G.; Chen, P. Y.; Lee, T. H. Molecules 2012, 17, 2082. |
| [14] | Zhang, B.-Y.; Wang, H.; Luo, X. D.; Du, Z. Z.; Zhang, X. F. Helv. Chim. Acta 2012, 95, 1672. |
| [15] | Allick, R.-L.; Richard, C. C.; Peter, S.; Paul, D. Phytochemistry 1990, 29, 2239. |
| [16] | Zhang, X.-F.; Zhou, Y.; Peng, S.; Zhou, D. W.; Wang, H. Fitoterapia 2008, 79, 262. |
| [17] | Gao, J.; Chen, B. Q.; Liu, Y. Q.; Xin, X. L.; Haji, A. A. Phytochemistry 2016, 122, 246. |
| [18] | Bamesh, S.; Trivedi, V. Orig. Pap. 2021, 63, 992. |
| [19] | Hu, W.-Y.; He, Z. Y.; Yang, L. J.; Zhang, M.; Xiao, Z. C. Brit. J. Pharmacol. 2015, 172, 2273. |
| [20] | Zhang, Y. -W.; Li, Z. M.; Min, Q. X.; Palida, A.; Li, H. Bioorg. Chem. 2018, 77, 478. |
| [21] | Braicu, C.; Zanoaga, O.; Zimta, A. A.; Tigu, A. B.; Ioana, B. N. Semin. Cancer Biol. 2022, 80, 218. |
| [22] | Xu, C.-F.; Wu, A. R.; Zhu, H.; Fang, H. Y.; Shen, J. Q. Biomedicine Pharmacotherapy 2013, 67, 133. |
| [23] | Fayed, E. A.; Gohar, N. A.; Farrag, A. M.; Ammar, Y. A. Arch. Pharm. 2022, 355, e2100454. |
/
| 〈 |
|
〉 |
