常春藤皂苷元衍生物的合成和抗肿瘤活性

doi:10.6023/cjoc202204021

有机化学 ›› 2022, Vol. 42 ›› Issue (9): 2877-2887.DOI: 10.6023/cjoc202204021 上一篇下一篇

研究论文

常春藤皂苷元衍生物的合成和抗肿瘤活性

黄兴, 张昌浩, 邓浩, 沈庆坤, 郭红艳, 全哲山, 李志勇^*(), 金莉莉^*()

延边大学药学院长白山天然药物教育部重点实验室吉林延吉 133000

收稿日期:2022-04-07 修回日期:2022-05-25 发布日期:2022-06-08
通讯作者: 李志勇, 金莉莉
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(81960626); 国家自然科学基金(82160666); 国家自然科学基金(82160628); 中国吉林省教育厅(JJKH 20191156KJ)

Synthesis and Antitumor Activity of Hederagenin Derivatives

Xing Huang, Changhao Zhang, Hao Deng, Qingkun Shen, Hongyan Guo, Zheshan Quan, Zhiyong Li(), Lili Jin()

Key Laboratory of Natural Medicines of the Changbai Mountain (Ministry of Education), College of Pharmacy, Yanbian University, Yanji, Jilin 133000

Received:2022-04-07 Revised:2022-05-25 Published:2022-06-08
Contact: Zhiyong Li, Lili Jin
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(81960626); National Natural Science Foundation of China(82160666); National Natural Science Foundation of China(82160628); Jilin Provincial Education Department of China(JJKH 20191156KJ)

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摘要/Abstract

以常春藤皂苷元为先导化合物, 设计并合成了三个系列的含有各种杂环的新型常春藤皂苷元衍生物, 并利用¹H NMR, ¹³C NMR和HRMS对其结构进行了表征. 通过噻唑蓝(MTT)方法评估了这些化合物对人非小细胞肺癌细胞(A549)、人乳腺癌细胞(MCF-7)、人结肠癌细胞(HCT116)、人结肠癌细胞(SW620)、人肝癌细胞(HepG-2)和人肝癌细胞(BEL7402)的体外抗肿瘤活性. 实验结果表明, (3β,4α)-3,23-二羟基齐墩果-12-烯-28-酸-[1-(4-硝基苯基)-1H-1,2,3-三唑-4-基]甲酯(A5)对HCT116细胞的抗增殖活性最强(IC₅₀=2.05 μmol/L). 蛋白印迹实验表明, 化合物A5可能通过NF-κB信号通路发挥其抗肿瘤活性.

关键词: 常春藤皂苷元, 抗肿瘤, 噻唑蓝(MTT)法, 蛋白印迹

Using hederagenin as lead compound, three series of novel hederagenin derivatives containing various heterocycles were designed and synthesized. Their structures were characterized by ¹H NMR, ¹³C NMR and HRMS. The in vitro antitumor activities of these compounds on human non-small cell lung cancer cells (A549), human breast cancer cells (MCF-7), human colon cancer cells (HCT116), human colon cancer cells (SW620), human hepatoma cells (HepG-2) and human hepatoma cells (BEL7402) were evaluated by thiazolyl blue (MTT) method. The experimental results showed that (3β,4α)-3,23-dihydroxy- olean-12-ene-28-acid-(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl) methyl ester (A5) had the strongest anti-proliferative activity (IC₅₀=2.05 μmol/L) on HCT116 cells. Western blotting experiments showed that compound A5 may exert its antitumor activity through NF-κB signaling pathway.

Key words: hederagenin, anticancer, thiazolyl blue (MTT) assay, Western blotting

引用此文

黄兴, 张昌浩, 邓浩, 沈庆坤, 郭红艳, 全哲山, 李志勇, 金莉莉. 常春藤皂苷元衍生物的合成和抗肿瘤活性[J]. 有机化学, 2022, 42(9): 2877-2887.

Xing Huang, Changhao Zhang, Hao Deng, Qingkun Shen, Hongyan Guo, Zheshan Quan, Zhiyong Li, Lili Jin. Synthesis and Antitumor Activity of Hederagenin Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2877-2887.

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图/表 12

图1. 常春藤皂苷元的化学结构及其碳原子序号

Figure 1. Chemical structure of hederagenin and the serial number of its carbon atom

图2. 含有苯基-1,2,3-三唑和3H-1,2,4-三唑-3-酮的天然产物衍生物的结构

Figure 2. Structures of natural-product derivatives containing phenyl-1,2,3-triazole and 3H-1,2,4-triazol-3-one

图式1. 含有含苯基-1,2,3-三唑和3H-1,2,4-三唑-3-酮或香豆素的常春藤皂苷元衍生物的设计

Scheme 1. Design of hederagenin derivatives containing phenyl-1,2,3-triazole and 3H-1,2,4-triazol-3-one or coumarin

图式2. 中间体的合成

Scheme 2. Synthesis of intermediates Reagents and conditions: (a) (i) HCl (ω=10%), NaNO2, H2O, 0~5 ℃, 30 min; (ii) NaN3, H2O, 0~5 ℃, 2~4 h. (b) propynol, Na ascorbate, CuSO4•5H2O, H2O, t-BuOH/H2O, 25 ℃, overnight. (c) thionyl chloride, CH2Cl2, r.t., overnight. (d) (i) methyl hydrazinocarboxylate, triethyl orthoformate, EtOH, reflux, 48 h; (ii) CH3ONa, EtOH, reflux, 48 h. (e) 1,2-dibromoethane, DMF, K2CO3, 60 ℃, 4~6 h.

图式3. 常春藤皂苷元衍生物的合成

Scheme 3. Synthesis of hederagenin derivatives

Compd.	R	Growth inhibition/%
Compd.	R	HCT116	SW620	BEL7402	HepG2	MCF-7	A549
He	—	26.21	24.22	31.19	19.69	32.43	NA
A1	4-H	46.13	24.42	34.24	39.81	NA	NA
A2	4-Cl	NA	28.11	30.67	NA	17.38	NA
A3	3,4-Cl₂	31.23	20.86	NA	56.07	NA	32.54
A4	4-OCH₃	NA	NA	NA	NA	36.86	NA
A5	4-NO₂	90.48	27.22	39.52	53.79	11.00	44.60
B1	4-H	29.55	NA	17.24	32.26	37.48	25.71
B2	4-F	28.77	NA	53.10	34.31	34.81	NA
B3	4-Cl	NA	12.81	27.10	31.26	44.29	23.73
B4	3,4-Cl₂	NA	17.94	NA	NA	45.76	55.56
B5	4-OCH₃	NA	44.08	NA	46.43	48.24	41.75
B6	3,4-(OCH₃)₂	24.19	13.03	10.29	NA	NA	5.08
B7	3,4,5-(OCH₃)₂	24.77	34.97	23.38	36.36	21.00	54.60
B8	4-CH₃	11.39	NA	26.14	43.21	32.95	NA
C1	—	88.91	30.16	14.11	74.53	49.59	NA
C2	—	79.49	26.57	NA	10.38	78.31	NA

表1. 化合物A1~A5, B1~B8, C1和C2的抗增殖活性(30 μmol/L)a

Table 1. Antiproliferative activity of compounds A1~A5, B1~B8, C1 and C2 (30 μmol/L)

Compd.	R	IC₅₀ value^b/(μmol•L^–1)
Compd.	R	HCT116	HepG2	MCF-7
A5	4-NO₂	2.05	27.89	>30
C1	—	16.02	16.31	>30
C2	—	18.12	>30	19.12
5-FU	—	24.80	10.93	28.11

表2. 化合物A5, C1和C2对三种人类癌细胞系的IC50a

Table 2. IC50 of compounds A5, C1 and C2 against three human cancer cell lines

Compd.	R	IC₅₀^a/(μmol•L^–1)	SI^b
Compd.	R	IC₅₀^a/(μmol•L^–1)	HCT116	HepG2	MCF-7
A5	4-NO₂	>30	14.63	1.07	NT
C1	—	>30	1.87	1.84	NT
C2	—	>30	1.65	NT	1.57
5-FU		19.12	0.77	1.75	0.68

表3. 化合物A5, C1和C2对正常细胞系(L02)的体外细胞毒性(IC50)a

Table 3. In vitro cytotoxicity of compounds A5, C1 and C2 against normal cell line (L02)

图3. 化合物A5抑制HCT116 细胞集落形成

Figure 3. Colony formation of HCT116 cells inhibited by compound A5 (A) HCT116 cells were incubated with varying concentrations of A5 (0, 7.5, 15, 30 μmol/L) and stained with crystal violet. (B) micrographic differences between the colonies. Images were taken of stained single colonies observed under a microscope.

图4. H&E染色的HCT116细胞形态

Figure 4. HCT116 cell morphology stained by H&E

图5. 化合物A5对HCT116细胞Bax、Bcl-2和NF-κB信号通路水平的影响

Figure 5. Effect of compound A5 on the levels of Bax, Bcl-2 and NF-κB signaling pathway in HCT116 cells Cells were pretreated with the various concentrations of compound A5 (7.5, 15 and 30 μmol/L) for 24 h. The expression of Bax, Bcl-2, p-NF-κB p65, NF-κB p65, p-IκB-α, IκB-α were analyzed by Western blot. ***p<0.001, **p<0.01, *p<0.05 vs control group.

图6. 化合物A5对HCT116细胞MAPK信号通路的影响

Figure 6. Effect of compound A5 on MAPK signaling pathway in HCT116 cells Cells were pretreated with the various concentrations of compound A5 (7.5, 15 and 30 μmol/L) for 24 h. The expression of p-ERK, ERK, p-JNK, JNK, p-p38, p38 were analyzed by Western blot. ***p<0.001, **p<0.01, *p<0.05 vs control group.

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常春藤皂苷元衍生物的合成和抗肿瘤活性

Synthesis and Antitumor Activity of Hederagenin Derivatives

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