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

Abstract

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

CLC Number:

TQ35

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.

Figures/Tables 5

References 24

1	THAI A A , SOLOMON B J , SEQUIST L V , et al. Lung cancer[J]. The Lancet, 2021, 398 (10299): 535- 554. doi: 10.1016/S0140-6736(21)00312-3
2	SUNG H , FERLAY J , SIEGEL R L , et al. Global cancer statistics 2020:GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries[J]. CA: A Cancer Journal for Clinicians, 2021, 71 (3): 209- 249. doi: 10.3322/caac.21660
3	GARG J, CHIU M N, KRISHNAN S, et al. Applications of lignin nanoparticles for cancer drug delivery: An update[J/OL]. Materials Letters, 2022, 311: 131573[2022-10-05]. https://doi.org/10.1016/j.matlet.2021.131573.
4	LU F J , CHU L H , GAU R J . Free radical-scavenging properties of lignin[J]. Nutrition and Cancer, 1998, 30 (1): 31- 38. doi: 10.1080/01635589809514637
5	LÁBAJ B K J . Antigenotoxic effect of lignin preparations from wastes of pulp and paper industry-in vitro and ex vivo activivity[J]. Acta Facultatis Xylologiae Zvolen, 2010, 53 (1): 69- 76.
6	GEIES A , ABDELAZIM M , SAYED A M , et al. Thermal, morphological and cytotoxicity characterization of hardwood lignins isolated by in-situ sodium hydroxide-sodium bisulfate method[J]. Natural Resources, 2020, 11 (10): 427- 438. doi: 10.4236/nr.2020.1110025
7	叶哲孜, 谢益民, 吴晨曦, 等. 多糖存在下异丁香酚的脱氢聚合及LCC的形成[J]. 林产化学与工业, 2016, 36 (2): 45- 50. doi: 10.3969/j.issn.0253-2417.2016.02.007
	YE Z Z , XIE Y M , WU C X , et al. Dehydrogenation polymerization of isoeugenol and formation of lignin-carbohydrate complexes with presence of polysaccharide[J]. Chemistry and Industry of Forest Products, 2016, 36 (2): 45- 50. doi: 10.3969/j.issn.0253-2417.2016.02.007
8	陈学宽, 赵厚宽, 吴宏飞, 等. 异丁香酚脱氢聚合产物的合成及其抗氧化性能研究[J]. 林产化学与工业, 2018, 38 (1): 87- 92.
	CHEN X K , ZHAO H K , WU H F , et al. Preparation and antioxidant properties of dehydrogenation polymer of isoeugenol[J]. Chemistry and Industry of Forest Products, 2018, 38 (1): 87- 92.
9	XIE Y M , JIANG C , CHEN X K , et al. Preparation of oligomeric phenolic compounds (DHPs) from coniferin and syringin and characterization of their anticancer properties[J]. BioResources, 2020, 15 (1): 1791- 1809. doi: 10.15376/biores.15.1.1791-1809
10	SAKAGAMI H , ASANO K , YOSIDA T , et al. Organ distribution and toxicity of lignin[J]. In Vivo, 1999, 13 (1): 41- 44.
11	UGARTONDO V , MITJANS M , VINARDELL M P . Applicability of lignins from different sources as antioxidants based on the protective effects on lipid peroxidation induced by oxygen radicals[J]. Industrial Crops and Products, 2009, 30 (2): 184- 187. doi: 10.1016/j.indcrop.2009.03.001
12	BARAPATRE A , MEENA A S , MEKALA S , et al. In vitro evaluation of antioxidant and cytotoxic activities of lignin fractions extracted from Acacia nilotica[J]. International Journal of Biological Macromolecules, 2016, 86, 443- 453. doi: 10.1016/j.ijbiomac.2016.01.109
13	TURLIUC M D , CUCU A I , CARAULEANU A , et al. Efficiency and safety of microporous polysaccharide hemispheres from potato starch in brain surgery[J]. Cellulose Chemistry Technology, 2018, 52, 505- 513.
14	BJÖRKMAN A . Lignin and lignin-carbohydrate complexes[J]. Industrial & Engineering Chemistry, 1957, 49 (9): 1395- 1398.
15	BONOLI M , VERARDO V , MARCONI E , et al. Antioxidant phenols in barley (Hordeum vulgare L.) flour: Comparative spectrophotometric study among extraction methods of free and bound phenolic compounds[J]. Journal of Agricultural and Food Chemistry, 2004, 52 (16): 5195- 5200. doi: 10.1021/jf040075c
16	LE N T , DONADU M G , HO D V , et al. Biological activities of essential oil extracted from leaves of Atalantia sessiflora Guillauminin Vietnam[J]. Journal of Infection in Developing Countries, 2020, 14 (9): 1054- 1064. doi: 10.3855/jidc.12469
17	NGA N T H, NGOC T T B, TRINH N T M, et al. Optimization and application of MTT assay in determining density of suspension cells[J/OL]. Analytical Biochemistry, 2020, 610: 113937[2022-10-05]. https://doi.org/10.1016/j.ab.2020.113937.
18	刘婧伊, 马林, 王春鹏, 等. 玉米芯木质素低聚物超声波辅助制备及其表征[J]. 生物质化学工程, 2023, 57 (6): 8- 14.
	LIU J Y , MA L , WANG C P , et al. Ultrasound assisted preparation and characterization of corn cob lignin oligomers[J]. Biomass Chemical Engineering, 2023, 57 (6): 8- 14.
19	GREVER M R , SCHEPARTZ S A , CHABNER B A . The National Cancer Institute: Cancer drug discovery and development program[J]. Seminars in Oncology, 1993, 19 (6): 622- 638.
20	GOLDIN A , VENDITTI J M , MACDONALD J S , et al. Current results of the screening program at the division of cancer treatment, national cancer institute[J]. European Journal of Cancer, 1981, 17 (2): 129- 142. doi: 10.1016/0014-2964(81)90027-X
21	GERAN R I . Protocols for screening chemical agents and natural products against animal tumors and other biological systems[J]. Cancer Chemotherapy and Pharmacology, 1972, 3, 17- 27.
22	RALPH J , LAPIERRE C , MARITA J M , et al. Elucidation of new structures in lignins of CAD-and COMT-deficient plants by NMR[J]. Phytochemistry, 2001, 57 (6): 993- 1003. doi: 10.1016/S0031-9422(01)00109-1
23	叶哲孜. 低聚木质素的体外合成及其生物活性的研究[D]. 武汉: 湖北工业大学, 2017.
	YE Z Z. Reserch on the synthesis of lignin oligomers in vitro and their biological activies[D]. Wuhan: Hubei University of Technology, 2017.
24	ZEMEK J , KOŠÍKOVÁ B , AUGUSTIN J , et al. Antibiotic properties of lignin components[J]. Folia Microbiologica, 1979, 24 (6): 483- 486. doi: 10.1007/BF02927180

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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The Separation of Ginkgo Kraft Lignin Components and Its Anti-tumor Structure-activity

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