氢化松香酯键合硅胶制备柱的研制及性能研究

doi:10.3969/j.issn.0253-2417.2024.02.001

Abstract

Abstract:

Hydrogenated rosin glycol acrylate(EGHRA) was bonded to the surface of thioglycolated silica gel(SH@SiO₂) by click chemical reaction to prepare a novel hydrogenated rosin acrylate ethylene glycol ester bonded silica gel(EGHRA@SiO₂) stationary phase. The synthesized stationary phase was characterized by elemental analysis, infrared spectroscopy, thermogravimetric analysis, N₂ adsorption-desorption experiments, and particle size distribution tests. The results showed that the EGHRA@SiO₂ stationary phase had an increased C content of 10.72 percentage points compared to SiO₂, a specific surface area of 270.06 m²/g, an average pore diameter of 6.16 nm, and an average particle size of 10 μm. A 250 mm×30 mm preparation column was filled by homogenization method, and a series of chromatographic evaluations were performed, demonstrating good flowability typical reversed-phase chromatographic characteristic as well as excellent stability and reproducibility of the EGHRA@SiO₂ preparation column. Tanaka tests showed that the spatial selectivity of EGHRA@SiO₂ column was superior to that of C18 column owing to the phenanthrene-like skeleton of the bonding monomer. Under reversed-phase chromatographic mode, EGHRA@SiO₂ preparation column exhibited ideal separation performance for the crude extracts of Taxus bark. Using the screened acetonitrile-water(volume ratio of 47∶53) mobile phase at a flow rate of 15 mL/min, the purity of paclitaxel(PTX), 10-deacetylbaccatin III(10-DAT), 7-xylosyl-10-deacetylbaccatin III(7-xyl-10-DAT) and cephalomannine(CEP) in the crude extract were increased by 91.52, 83.24, 62.99 and 55.85 percentage points after a single purification step of 1.0 mL injection sample, respectively.

Key words: rosin, preparative liquid chromatography, paclitaxel, preparation column

CLC Number:

TQ35

Lijuan JIANG, Huiying WU, Lei ZENG, Yuping SU, Fuhou LEI, Hao LI. Preparation and Properties of Hydrogenated Rosin Ester Bonded Silica Gel Column[J]. Chemistry and Industry of Forest Products, 2024, 44(2): 1-8.

Figures/Tables 9

Fig.1

Fig.2

Table 1

Fig.3

Fig.4

Fig.5

Fig.6

Fig.7

Fig.8

References 26

1	SECA A M L, PINTO D C G A. Plant secondary metabolites as anticancer agents: Successes in clinical trials and therapeutic application[J/OL]. International Journal of Molecular Sciences, 2018, 19(1): 263[2023-03-20]. https://doi.org/10.3390/ijms19010263.
2	黄晓妍, 师以康. 抗肿瘤药物紫杉醇结构修饰的研究进展[J]. 山东医药, 2019, 59 (15): 95- 100.
	HUANG X Y , SHI Y K . Progress of structural modification of the antitumor drug paclitaxel[J]. Shandong Medicine Journal, 2019, 59 (15): 95- 100.
3	SOFIAS A M , DUNNE M , STORM G , et al. The battle of "nano" paclitaxel[J]. Advanced Drug Delivery Reviews, 2017, 122, 20- 30. doi: 10.1016/j.addr.2017.02.003
4	KANG H J , KIM J H . Removal of residual chloroform from amorphous paclitaxel pretreated by alcohol[J]. Korean Journal of Chemical Engineering, 2019, 36 (12): 1965- 1970. doi: 10.1007/s11814-019-0413-9
5	NIŽNANSKÝ L', OSINOVÁ D, KURUC R, et al. Natural taxanes: From plant composition to human pharmacology and toxicity[J/OL]. International Journal of Molecular Sciences, 2022, 23(24): 15619[2023-03-20]. https://doi.org/10.3390/ijms232415619.
6	KANG D Y , KIM J H . Two-component adsorption characteristics of paclitaxel and 10-deacetylpaclitaxel from Taxus chinensis onto sylopute[J]. Biotechnology and Bioprocess Engineering, 2022, 27 (1): 145- 155. doi: 10.1007/s12257-021-0123-0
7	ZHANG L S, SUN X M, WILSON I W, et al. Identification of the genes involved in anthocyanin biosynthesis and accumulation in Taxus chinensis[J/OL]. Genes, 2019, 10(12): 982[2023-03-20]. https://doi.org/10.3390/genes10120982.
8	LI P F , WANG T , LEI F H , et al. Preparation and evaluation of paclitaxel-imprinted polymers with a rosin-based crosslinker as the stationary phase in high-performance liquid chromatography[J]. Journal of Chromatography A, 2017, 1502, 30- 37. doi: 10.1016/j.chroma.2017.04.048
9	李浩, 谢文博, 曾磊, 等. 核壳型松香基高分子键合硅胶液相色谱固定相高效分离紫杉醇[J]. 林产化学与工业, 2023, 43 (1): 34- 42.
	LI H , XIE W B , ZENG L , et al. High efficient separation of paclitaxel by core-shell rosin-based polymer bonded silica gel liquid chromatography[J]. Chemistry and Industry of Forest Products, 2023, 43 (1): 34- 42.
10	MIN H S , KIM J H . Process synthesis and optimization for the isolation and purification of paclitaxel from Taxus chinensis[J]. Korean Journal of Chemical Engineering, 2022, 39 (12): 3389- 3398. doi: 10.1007/s11814-022-1261-6
11	JIN G W , GUO Z M , XIAO Y S , et al. Practical method for the definition of chromatographic peak parameters in preparative liquid chromatography[J]. Journal of Separation Science, 2016, 39 (20): 3917- 3926. doi: 10.1002/jssc.201600579
12	WANG X H , LIANG Y , PENG C L , et al. Preparative isolation and purification of chemical constituents of Belamcanda by MPLC, HSCCC, and prep-HPLC[J]. Journal of Liquid Chromatography & Related Technologies, 2011, 34 (4): 241- 257.
13	吴希, 邓勤, 徐志勇, 等. 制备型高效液相色谱在天然产物分离中的应用[J]. 化学分析计量, 2017, 26 (1): 113-117, 122.
	WU X , DENG Q , XU Z Y , et al. Application of preparative high performance liquid chromatography in separation of natural products[J]. Chemical Analysis and Meterage, 2017, 26 (1): 113-117, 122.
14	NURULLAH M, USMANI Z, AHMAD S, et al. Purification and characterization of taxol and 10-deacetyl baccatin III from the bark, needles, and endophytes of Taxus baccata by preparative high-performance liquid chromatography, ultra-high-performance liquid chromatography-mass spectrometry, and nuclear magnetic resonance[J/OL]. Journal of Separation Science, 2023: 46(6): e2200841[2023-03-20]. https://doi.org/10.1002/jssc.202200841.
15	李国祥, 邓杰, 曾磊, 等. SiO₂/松香-腰果酚核壳型液相色谱固定相高效分离天麻素[J]. 分析化学, 2019, 47 (12): 1946- 1950.
	LI G X , DENG J , ZENG L , et al. Highly selective separation of gastrodin by SiO₂/rosin-cardano core-shell liquid chromatography stationary phase[J]. Chinese Journal of Analytical Chemistry, 2019, 47 (12): 1946- 1950.
16	SUN Y , LI P F , WANG T , et al. Alkaloid purification using rosin-based polymer-bonded silica stationary phase in HPLC[J]. Journal of Separation Science, 2019, 42 (24): 3646- 3652. doi: 10.1002/jssc.201900835
17	易冯梅, 谢文博, 李浩, 等. 核壳型SiO₂@松香基高分子高效液相制备柱的制备及其对喜树碱的分离纯化[J]. 林产化学与工业, 2021, 41 (6): 67- 75.
	YI F M , XIE W B , LI H , et al. Preparation of core-shell SiO₂@rosin-based polymer high performance liquid column and its purification for Camptothecin[J]. Chemistry and Industry of Forest Products, 2021, 41 (6): 67- 75.
18	XIE W B, LI H, SUN Y, et al. Separating and purifying of Panax notoginseng saponins using a rosin-based polymer-bonded with silica as a high-performance liquid chromatography stationary phase[J/OL]. Microchemical Journal, 2022, 176: 107234[2023-03-20]. https://doi.org/10.1016/j.microc.2022.107234.
19	张成, 姚兴东, 雷福厚. SiO₂@松香基高分子(Ru131)色谱柱分离测定岩黄连中脱氢卡维丁、盐酸巴马汀和盐酸小檗碱[J]. 分析科学学报, 2022, 38 (1): 66- 70.
	ZHANG C , YAO X D , LEI F H . Separation and determination of dehydrocarvidine, palmatine hydrochloride and berberine hydrochloride in coptis chinensis by SiO₂@ rosin-based polymer(Ru131) column[J]. Journal of Analytical Sciences, 2022, 38 (1): 66- 70.
20	FAN J P, YUAN T T, XU X K, et al. Preparation and characterization of mock strawberry-like aminopropyl-modified mesoporous silica for column chromatographic purification of paclitaxel in Taxus×Media[J/OL]. Chemical Engineering Journal, 2019: 359[2023-03-20]. https://doi.org/10.1016/j.cej.2018.11.024.
21	LI H, XIE W B, ZENG L, et al. Development and evaluation of a hydrogenated rosin(β-acryloxyl ethyl) ester-bonded silica stationary phase for high-performance liquid chromatography separation of paclitaxel from yew bark[J/OL]. Journal of Chromatography A, 2022, 1665: 462815[2023-03-20]. https://doi.org/10.1016/j.chroma.2022.462815.
22	ZENG L, XIE W B, JIANG L J, et al. Fabrication and evaluation of dodecyl imide maleopimaric acid glycidyl methacrylate ester modified silica with multiple retention mechanisms for reversed phase liquid chromatography[J/OL]. Journal of Chromatography A, 2023, 1689: 463747[2023-03-20]. https://doi.org/10.1016/j.chroma.2022.463747.
23	JIANG D N, CHEN J, GUAN M, et al. Octadecylimidazolium ionic liquids-functionalized carbon dots and their precursor co-immobilized silica as hydrophobic chromatographic stationary phase with enhanced shape selectivity[J/OL]. Talanta, 2021, 233: 122513[2023-03-20]. https://doi.org/10.1016/j.ta-lanta.2021.122513.
24	国家药典委员会. 中华人民共和国药典: 一部[M]. 北京: 中国医药科技出版社, 2020: 1625.
	Chinese Pharmacopoeia Commission . Pharmacopoeia of the People's Republic of China: A[M]. Beijing: China Medical Science Press, 2020: 1625.
25	WU Q, HOU X D, ZHANG X F, et al. Amphipathic carbon quantum dots-functionalized silica stationary phase for reversed phase/hydrophilic interaction chromatography[J/OL]. Talanta, 2021, 226: 122148[2023-03-20]. https://doi.org/10.1016/j.talanta.2021.122148.
26	卢佩章, 戴朝政, 张祥民. 色谱理论基础[M]. 北京: 科学出版社, 1997.
	LU P Z , DAI C Z , ZHANG X M . Theoretical basis of chromatography[M]. Beijing: Science Press, 1997.

样品 sample	BET比表面积/(m²·g^-1) BET surface area	平均孔径/nm average pore size	孔体积/(cm³·g^-1) pore volume	元素分析elemental analysis/%
样品 sample	BET比表面积/(m²·g^-1) BET surface area	平均孔径/nm average pore size	孔体积/(cm³·g^-1) pore volume	C	H
SiO₂	540.36	7.26	1.12	0.19±0.06	1.62±0.30
SH-SiO₂	417.75	6.69	0.82	2.10±0.09	1.17±0.01
EGHRA@SiO₂	270.06	6.16	0.57	10.91±0.06	2.26±0.13

[1]	Wen QI, Yajing HU, Xingwei LI, Man QIN, Chun LU. Preparation and Properties of Fluorocarbon Coatings Modified by Hydroxyl Hydrogenated Rosin Derivative [J]. Chemistry and Industry of Forest Products, 2023, 43(6): 74-80.
[2]	Simai QI, Tong LUO, Meihong LIU, Chunpeng WANG, Fuxiang CHU, Jifu WANG. Preparation and Properties of Pressure Sensitive Adhesives with Rosin-oil and Furfural-oil Based Semi-interpenetrating Networks [J]. Chemistry and Industry of Forest Products, 2023, 43(5): 32-40.
[3]	Tong LIU, Qian LIU, Wanting GU, Jie SONG, Jianxin JIANG, Chunrui HAN. One Step Synthesis of Novel Natural Rosin Derivative and Green Synthesis of Its Hybrid Materials at Mild Temperature [J]. Chemistry and Industry of Forest Products, 2023, 43(3): 16-24.
[4]	Simai QI, Tong LUO, Meihong LIU, Chunpeng WANG, Fuxiang CHU, Jifu WANG. Preparation and Properties of Pressure Sensitive Adhesives Derived from Rosin Bio-based Acrylate [J]. Chemistry and Industry of Forest Products, 2023, 43(2): 49-55.
[5]	Yilu SHI, Fengli YU, Bing YUAN, Congxia XIE, Shitao YU. Preparation and Characterization of Ni-B/C_xN_y@mSiO₂ Catalysts and Their Catalytic Properties for Rosin Hydrogenation [J]. Chemistry and Industry of Forest Products, 2023, 43(1): 25-33.
[6]	Hao LI, Wenbo XIE, Lei ZENG, Liuyu YI, Wen LI, Fuhou LEI. Highly Effective Separation of Paclitaxel by Using Core-shell Rosin-based Polymer Bonded Silica as Liquid Chromatography Stationary Phase [J]. Chemistry and Industry of Forest Products, 2023, 43(1): 34-42.
[7]	Yaocang LI, Jiawei SHAO, Hongxia MA. Properties of Rosin-modified Cardanol Coatings [J]. Chemistry and Industry of Forest Products, 2022, 42(5): 56-60.
[8]	Meng LIANG, Yafeng WANG, Taojie XIE, Hongjie ZHU, Yonglin HUANG. Chemical Constituents and Tyrosinase Inhibitory Activities from the Pink Flowers of Bauhinia variegata L. [J]. Chemistry and Industry of Forest Products, 2022, 42(4): 68-74.
[9]	Shengfeng YE, Zhaolan ZHAI, Shibin SHANG, Zhanqian SONG. Synthesis and Properties of a Rosin-based Anionic Surfactant with Azobenzene Group [J]. Chemistry and Industry of Forest Products, 2022, 42(3): 57-64.
[10]	Xiaoliang GUO, Simai QI, Chunpeng WANG, Fuxiang CHU, Jifu WANG. Synthesis of Ethyl Cellulose, Gum Rosin and Fatty Acid Based Polymer and Its Application Performance as Pressure Sensitive Adhesive [J]. Chemistry and Industry of Forest Products, 2022, 42(3): 90-96.
[11]	Lu LU, Chengjie SHU, Ling GE, Jiechen PAN, Kai ZHU, Baojun SHI. The Antibacterial Activity, Antioxidant and Antityrosinase Activities of Cinnamon Essential Oil and Cinnamaldehyde [J]. Chemistry and Industry of Forest Products, 2022, 42(3): 105-110.
[12]	Zhen HUANG, Shibo WANG, Chunyu REN, He LIU, Xu XU, Zhanqian SONG. Preparation and Application of Rosin Modified Siloxane-based Flame Retardant [J]. Chemistry and Industry of Forest Products, 2022, 42(2): 71-79.
[13]	Tong LIU, Yuxuan DONG, Wanting GU, Bing HAN, Chunrui HAN. Research Progress on Application of Rosin and Its Derivatives in Inorganic Functional Materials [J]. Chemistry and Industry of Forest Products, 2022, 42(1): 123-130.
[14]	Fengmei YI, Wenbo XIE, Hao LI, Lei ZENG, Wen LI, Fuhou LEI. Preparation of Core-shell SiO₂@Rosin-based Polymer High Performance Liquid Preparation Column and Purification of Camptothecin [J]. Chemistry and Industry of Forest Products, 2021, 41(6): 67-75.
[15]	Xiaoliang GUO, Simai QI, Chunpeng WANG, Jifu WANG, Fuxiang CHU. Preparation and Characterization of Rosin Grafted Cellulose Nanocrystals Reinforced Natural Rubber Composites [J]. Chemistry and Industry of Forest Products, 2021, 41(5): 72-78.

Preparation and Properties of Hydrogenated Rosin Ester Bonded Silica Gel Column

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 9

References 26

Related Articles 15

Recommended Articles

Metrics

Comments