α-桐酸酰胺类化合物的合成及抑菌、抗癌活性研究

doi:10.3969/j.issn.0253-2417.2021.05.006

林产化学与工业 ›› 2021, Vol. 41 ›› Issue (5): 38-44.doi: 10.3969/j.issn.0253-2417.2021.05.006

α-桐酸酰胺类化合物的合成及抑菌、抗癌活性研究

成江¹^,², 谢普军¹^,², 黄立新¹^,²^,*(), 张彩虹¹^,²

1. 中国林业科学研究院林产化学工业研究所; 生物质化学利用国家工程实验室; 国家林业和草原局林产化学工程重点实验室; 江苏省生物质能源与材料重点实验室, 江苏南京 210042
2. 南京林业大学江苏省林业资源高效加工利用协同创新中心, 江苏南京 210037

收稿日期:2020-12-03 出版日期:2021-10-28 发布日期:2021-11-04
通讯作者: 黄立新 E-mail:l_x_huang@163.com
作者简介:黄立新, 研究员, 博士生导师, 研究领域为天然资源化学利用; E-mail: l_x_huang@163.com
成江(1992-), 男, 湖南永州人, 博士生, 研究方向为天然资源化学利用
基金资助:
国家重点研发计划资助项目(2017YFD0601001);江苏省自然科学基金项目(BK20181124)

Synthesis, Antibacterial and Anticancer Activity of α-Eleostearic Amides Derivatives

Jiang CHENG¹^,², Pujun XIE¹^,², Lixin HUANG¹^,²^,*(), Caihong ZHANG¹^,²

1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China

Received:2020-12-03 Online:2021-10-28 Published:2021-11-04
Contact: Lixin HUANG E-mail:l_x_huang@163.com

摘要/Abstract

摘要：

为了寻求具有潜在生物活性的α-桐酸酰胺衍生物，以α-桐酸为原料，制备得到了一系列α-桐酸酰胺衍生物：α-桐酸-3-甲基苯酰胺(3a)、α-桐酸-4-甲氧基苯酰胺(3b)、α-桐酸-4-三氟甲氧基苯酰胺(3c)、α-桐酸-4-氟苯酰胺(3d)、α-桐酸-3-氯苯酰胺(3e)、α-桐酸-2，3-二氯苯酰胺(3f)、α-桐酸-2-甲基环己酰胺(3g)，并用FT-IR、¹H NMR、¹³C NMR和HPLC-MS对产物进行了确证。生物活性实验结果表明：化合物3c对肝癌细胞HepG2、直肠癌细胞DLD-1和乳腺癌细胞MCF-7均有较好的抑制效果，其对肝癌细胞HepG2的半数抑制浓度(IC₅₀，55.58 μmol/L)和5-氟尿嘧啶相近。所有目标化合物对大肠杆菌和金黄色葡萄球菌均具有一定的抑制活性，其中，化合物3f对金黄色葡萄球菌有良好的抑菌活性，IC₅₀为0.022 μmol/L，与氨苄青霉素钠的抗菌效果相近，具有成为动物饲料中抗生素替代品的潜力。

关键词: α-桐酸, 酰胺, 生物活性

Abstract:

In order to find α-eleostearic acid derivatives with potential biological activity, a series of α-eleostearic amides derived from α-eleostearic acid was synthesized: α-eleostearic-3-methylbenz-amide(3a), α-eleostearic-4-methoxybenz-amide(3b), α-eleostearic-4-trifluoromethbenz-amide(3c), α-eleostearic-4-fluorobenz-amide(3d), α-eleostearic-3-chlorobenz-amide(3e), α-eleostearic-2, 3-dichlorobenz-amide(3f), α-eleostearic-3-methylcyclohexan-amide(3g). The products were confirmed by FT-IR, ¹H NMR, ¹³C NMR and HPLC-MS. The results of biological activity experiments showed that compound 3c had good inhibitory effect on hepatocarcinoma cells HepG2, rectal carcinoma cells DLD-1 and breast cancer cells MCF-7. The 50% inhibition concentration of compound 3f on HepG2 was 55.58 μmol/L, which was similar to the 50% inhibition concentration of 5-fluorouracil. All compounds had inhibitory activity against Staphyloccocus aureus and Escherichia coli. Moreover, compound 3f had preferable antibacterial activity against Staphyloccocus aureus, the 50% inhibition concentration was 0.022 μmol/L, which was similar to ampicillin sodium and had the potential to replace antibiotics in animal feed.

Key words: α-eleostearic acid, amides, biological activity

中图分类号:

TQ35

成江, 谢普军, 黄立新, 张彩虹. α-桐酸酰胺类化合物的合成及抑菌、抗癌活性研究[J]. 林产化学与工业, 2021, 41(5): 38-44.

Jiang CHENG, Pujun XIE, Lixin HUANG, Caihong ZHANG. Synthesis, Antibacterial and Anticancer Activity of α-Eleostearic Amides Derivatives[J]. Chemistry and Industry of Forest Products, 2021, 41(5): 38-44.

图/表 3

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参考文献 18

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化合物 compound	抑制率inhibition rates(20 μmol/L)/%			抑制率inhibition rates(200 μmol/L)/%
化合物 compound	肝癌细胞 HepG2	直肠癌细胞 DLD-1	乳腺癌细胞 MCF-7	肝癌细胞 HepG2	直肠癌细胞 DLD-1	乳腺癌细胞 MCF-7
3a	0.35	3.13	0.35	6.65	4.40	15.21
3b	19.56	26.92	9.57	38.95	46.24	25.89
3c	27.07	34.21	32.62	66.11	70.46	62.59
3d	4.04	5.52	1.18	29.23	20.23	27.70
3e	5.87	0.59	4.72	15.28	10.40	22.38
3f	4.17	1.38	0.53	17.81	13.09	6.94
3g	4.05	1.54	3.98	8.57	8.57	17.74
5-氟尿嘧啶 5-fluorouracil	10.67	25.75	13.16	94.43	96.38	92.76

化合物 compound	IC₅₀/(mmol·L^-1)
化合物 compound	大肠杆菌E.coli	金黄色葡萄球菌S.aureus
3a	0.687	1.374
3b	1.316	0.329
3c	1.152	0.576
3d	0.326	1.302
3e	0.651	0.651
3f	1.316	0.022
3g	0.327	1.302
α-桐酸α-eleostearic acid
氨苄青霉素钠 ampicillin sodium	0.155	0.010

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α-桐酸酰胺类化合物的合成及抑菌、抗癌活性研究

Synthesis, Antibacterial and Anticancer Activity of α-Eleostearic Amides Derivatives

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