Diterpenoids with Cytotoxicity for Pancreatic Cancer SW1990 Cells from the Rhizomes of Euphorbia jolkinii Boiss

doi:10.6023/cjoc202312007

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1929-1937.DOI: 10.6023/cjoc202312007 Previous Articles Next Articles

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大狼毒根茎中对胰腺癌SW1990细胞具有毒性的二萜

朱红波^a, 王吉^a, 胡炜彦^b, 周堂^a, 林芷淇^a, 张荣平^a, 耿长安^c, 陈兴龙^a^,^*()

a 云南中医药大学中药学院暨云南省南药可持续利用研究重点实验室昆明 650500
b 昆明医科大学药学院暨云南省天然药物药理重点实验室昆明 650500
c 中国科学院昆明植物研究所植物化学与西部植物资源可持续利用国家重点实验室昆明 650201

收稿日期:2023-12-08 修回日期:2024-01-29 发布日期:2024-03-05
基金资助:
云南省基础研究计划(202201AU070166); “云岭学者”支持计划(YNWR-YLXZ-2019-019); 云南省教育厅科学研究基金(2023Y0455); 云南省科技厅社会发展专项(202303AC100025); 云南省南药可持续利用研究重点实验室开放课题(202105AG070012XS23015)

Diterpenoids with Cytotoxicity for Pancreatic Cancer SW1990 Cells from the Rhizomes of Euphorbia jolkinii Boiss

Hongbo Zhu^a, Ji Wang^a, Weiyan Hu^b, Tang Zhou^a, Zhiqi Lin^a, Rongping Zhang^a, Chang'an Geng^c, Xinglong Chen^a,*()

a School of Chinese Materia Medica & Yunnan Key Laboratory of Southern Medicine Utilization, Yunnan University of Chinese Medicine, Kunming 650500
b School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming 650500
c State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201

Received:2023-12-08 Revised:2024-01-29 Published:2024-03-05
Contact: * E-mail: chxlkib@163.com
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)

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Abstract

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 IC₅₀was (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.

Key words: Euphorbia jolkinii, ent-abietane diterpenoids, lathyrane diterpenoids, SW1990 cells, cytotoxicity, Bcl-2

Cite this article

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.

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Fig. & Tab. 7

References 23

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Position	Compound 1		Compound 2
Position	δ_H (J in Hz)^a	δ_C^b	δ_H (J in Hz)^a	δ_C^b
1	1.73~1.67 (m, 1H) 0.95~0.91 (m, 1H)	38.9 (t)	4.04 (dd, 1H, 11.0/4.4)	72.0 (d)
2	1.73~1.67 (m, 1H) 1.45 (overlap, 1H)	18.3 (t)	1.94~1.88 (m, 2H)	36.4 (t)
3	1.45 (overlap, 1H) 1.23~1.18 (m, 1H)	42.0 (t)	3.51 (s, 1H)	76.3 (d)
4	—	32.8 (s)	—	37.5 (s)
5	1.39 (overlap, 1H)	47.5 (d)	1.65 (d, 1H, 13.8)	47.8 (d)
6	2.01~1.98 (m, 1H) 1.73~1.67 (m, 1H)	25.9 (t)	1.72 (d, 1H, 12.6) 1.57~1.48 (m, 1H)	23.4 (t)
7	3.92 (br.s, 1H)	73.6 (d)	2.47~2.43 (m, 1H) 2.19 (td, 1H, 12.8/4.8)	37.0 (t)
8	—	71.8 (s)	—	152.8 (s)
9	1.39 (overlap, 1H)	48.4 (d)	2.47~2.43 (m, 1H)	52.2 (d)
10	—	37.2 (s)	—	47.0 (s)
11	1.83~1.80 (m, 1H) 1.39 (overlap, 1H)	16.5 (t)	3.68 (dd, 1H, 12.8 /5.6) 1.46~1.40 (m, 1H)	30.4 (t)
12	2.54 (d, 1H, 16.0) 2.09~2.05 (m, 1H)	24.9 (t)	4.99 (dd, 1H, 13.6/5.2)	76.5 (d)
13	—	141.1 (s)	—	157.3 (s)
14	6.61 (s, 1H)	142. 7 (d)	6.25 (s, 1H)	114.1 (d)
15	—	199.9 (s)	—	115.8 (s)
16	2.33 (s, 3H)	25.7 (q)	1.79 (s, 3H)	8.1 (q)
17	—	—	—	175.9 (s)
18	0.88 (s, 3H)	33.3 (q)	0.92 (s, 3H)	30.4 (q)
19	0.86 (s, 3H)	21.5 (q)	0.82 (s, 3H)	21.9 (q)
20	0.99 (s, 3H)	15.6 (q)	0.95 (s, 3H)	10.8 (q)

Position	Compound 1		Compound 2
Position	δ_H (J in Hz)^a	δ_C^b	δ_H (J in Hz)^a	δ_C^b
1	1.73~1.67 (m, 1H) 0.95~0.91 (m, 1H)	38.9 (t)	4.04 (dd, 1H, 11.0/4.4)	72.0 (d)
2	1.73~1.67 (m, 1H) 1.45 (overlap, 1H)	18.3 (t)	1.94~1.88 (m, 2H)	36.4 (t)
3	1.45 (overlap, 1H) 1.23~1.18 (m, 1H)	42.0 (t)	3.51 (s, 1H)	76.3 (d)
4	—	32.8 (s)	—	37.5 (s)
5	1.39 (overlap, 1H)	47.5 (d)	1.65 (d, 1H, 13.8)	47.8 (d)
6	2.01~1.98 (m, 1H) 1.73~1.67 (m, 1H)	25.9 (t)	1.72 (d, 1H, 12.6) 1.57~1.48 (m, 1H)	23.4 (t)
7	3.92 (br.s, 1H)	73.6 (d)	2.47~2.43 (m, 1H) 2.19 (td, 1H, 12.8/4.8)	37.0 (t)
8	—	71.8 (s)	—	152.8 (s)
9	1.39 (overlap, 1H)	48.4 (d)	2.47~2.43 (m, 1H)	52.2 (d)
10	—	37.2 (s)	—	47.0 (s)
11	1.83~1.80 (m, 1H) 1.39 (overlap, 1H)	16.5 (t)	3.68 (dd, 1H, 12.8 /5.6) 1.46~1.40 (m, 1H)	30.4 (t)
12	2.54 (d, 1H, 16.0) 2.09~2.05 (m, 1H)	24.9 (t)	4.99 (dd, 1H, 13.6/5.2)	76.5 (d)
13	—	141.1 (s)	—	157.3 (s)
14	6.61 (s, 1H)	142. 7 (d)	6.25 (s, 1H)	114.1 (d)
15	—	199.9 (s)	—	115.8 (s)
16	2.33 (s, 3H)	25.7 (q)	1.79 (s, 3H)	8.1 (q)
17	—	—	—	175.9 (s)
18	0.88 (s, 3H)	33.3 (q)	0.92 (s, 3H)	30.4 (q)
19	0.86 (s, 3H)	21.5 (q)	0.82 (s, 3H)	21.9 (q)
20	0.99 (s, 3H)	15.6 (q)	0.95 (s, 3H)	10.8 (q)

Compd.	IC₅₀^a/(μmol•L^–1)	Compd.	IC₅₀^a/(μmol•L^–1)
1	>50	5	>50
2	>50	6	>50
3	>50	7	44.97±9.16
4	>50	8	>50
紫杉醇^b	45.01±7.65

Compd.	IC₅₀^a/(μmol•L^–1)	Compd.	IC₅₀^a/(μmol•L^–1)
1	>50	5	>50
2	>50	6	>50
3	>50	7	44.97±9.16
4	>50	8	>50
紫杉醇^b	45.01±7.65

大狼毒根茎中对胰腺癌SW1990细胞具有毒性的二萜

Diterpenoids with Cytotoxicity for Pancreatic Cancer SW1990 Cells from the Rhizomes of Euphorbia jolkinii Boiss

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