银杏硫酸盐木质素组分分离及其抗肿瘤构效研究

doi:10.3969/j.issn.0253-2417.2024.01.003

摘要/Abstract

摘要：

为了从硫酸盐木质素中提取具有抗肿瘤活性的成分，以不同极性的溶剂对银杏硫酸盐木质素(KL)进行分级，利用MTT法研究各分级组分的抗肿瘤活性；根据抗肿瘤活性结果，利用中压制备液相色谱对抑制效果最明显组分进行纯化，采用质谱、¹³C NMR等方法确定其结构，并分析构效关系。FT-IR分析结果表明：KL具有与银杏磨木木质素(MWL)相似的结构；分级组分的总酚含量(TPC)随着其相对分子质量增加而降低。抗肿瘤实验结果表明：乙醚可溶组分(LC2)对人源肺癌A549细胞的抑制作用最强，IC₅₀值为(366.09±6.39) mg/L。LC2纯化结果发现，分离出的化合物L7的抗肿瘤活性最好，对肺癌A549细胞的IC₅₀值为(89.44±2.13) mg/L。质谱、¹³C NMR测试结果表明：化合物L7是酚羟基上连接着2-丙醛取代基的β-5结构的松柏醛二聚体。木质素小分子物质的苯丙烷单元侧链上醛基的增加会提高抗癌活性，但是醚键的增加会降低抗癌活性。

关键词: 硫酸盐木质素, 分级组分, 生理活性化合物, 抗肿瘤活性, 化学结构

Abstract:

To isolate anticancer substance from Kraft lignin, ginkgo Kraft lignin(KL) was fractionated with different polar solvents, and the anticancer activity of each fraction was studied by MTT method. The components with the most obvious inhibitory effect were purified by medium-pressure preparation liquid chromatography according to the results of anticancer activity determination. The structure of the compounds was determined by mass spectrometry and ¹³C NMR, and the structure-effect relationship was analyzed. The results of FT-IR spectra showed that ginkgo Kraft lignin had a similar structure to that of ginkgo milled wood lignin(MWL). The total phenol content(TPC) of the fractions decreased with the increase of their relative molecular mass. The results of anticancer activity showed that the ether soluble fraction(LC2) had a strongest inhibitory effect on human-derived lung cancer A549 cells with an IC₅₀ of (366.09±6.39) mg/L. Further purification of LC2 revealed that the isolated compound L7 had the best anticancer activity, with an IC₅₀ value of (89.44±2.13) mg/L against the lung cancer A549 cells. The results of mass spectrometric analysis and ¹³C NMR measurement indicated that compound L7 was a β-5 structure coniferyl aldehyde dimer with a 2-propionaldehyde substituent on the phenolic hydroxyl group. The increase of the aldehyde group on the side chain of the phenylpropane unit of the lignin fraction with small molecule could enhance the anticancer activity, while the increase of the ether bond would weaken the anticancer activity.

Key words: Kraft lignin, classified fraction, physiologically active compound, antitumor activity, chemical structure

中图分类号:

TQ35

谢益民, 岳园园, 赵云博, 魏鑫. 银杏硫酸盐木质素组分分离及其抗肿瘤构效研究[J]. 林产化学与工业, 2024, 44(1): 17-23.

Yimin XIE, Yuanyuan YUE, Yunbo ZHAO, Xin WEI. The Separation of Ginkgo Kraft Lignin Components and Its Anti-tumor Structure-activity[J]. Chemistry and Industry of Forest Products, 2024, 44(1): 17-23.

图/表 5

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分级组分 classified fraction	M_n	M_w	PDI(M_w/M_n)	TPC/%
LC1	475	743	1.56	172.14
LC2	775	1 356	1.75	100.53
LC3	1 697	2 514	1.48	82.17
LC4	2 198	4 783	2.17	59.01

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