Separation and Preparation of Sanguinarine and Chelerythrine from <i>Macleaya cordata</i> Root by High Speed Counter-Current Chromatography

JIA Changqing; MA Rui; QIAN Xicheng; WANG Dandan; YU Jiansheng

doi:10.13386/j.issn1002-0306.2021030072

Volume 43 Issue 1

Dec. 2021

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2022 > 43(1): 39-46. > DOI: 10.13386/j.issn1002-0306.2021030072

JIA Changqing, MA Rui, QIAN Xicheng, et al. Separation and Preparation of Sanguinarine and Chelerythrine from Macleaya cordata Root by High Speed Counter-Current Chromatography[J]. Science and Technology of Food Industry, 2022, 43(1): 39−46. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021030072.

Citation:

PDF (2730 KB)

Separation and Preparation of Sanguinarine and Chelerythrine from Macleaya cordata Root by High Speed Counter-Current Chromatography

1.
College of Pharmacy, Tongren Polytechnic College, Tongren 554300, China
2.
National Engineering Center for Veterinary Medicine in Nationalities, Tongren Polytechnic College, Tongren 554300, China
3.
Guizhou Fanjingshan Agricultural High-tech Co., Ltd., Tongren 554300, China

More Information

Received Date: March 07, 2021
Available Online: October 31, 2021

Graphical Abstract

Abstract

Abstract

The aim of this study was to develop a method for the separation and preparation of high purity sanguinarine and chelerythrine by conventional high speed counter-current chromatography. After comparing six kinds of solvent protocols of analytical high speed counter-current chromatography (HSCCC), the two phase system of chloroform-methanol-0.2 mol/L hydrochloric acid aqueous solution (4:2:2,V/V/V) was finally chosen as the operating solvent of preparative high speed counter-current chromatography (HSCCC), in which the upper phase was used as the stationary phase and the lower phase was used as the mobile phase. Under the conditions of ratations speed of 455 r/min, lower phase flow rate of 8 mL/min, the injection volume of 1000 mg, the temperature of 25 ℃, sanguinarine and chelerythrine was separated and preparated on HSCCC. The results showed that 505 mg of sanguinarine chloride and 435 mg of chelerythrine chloride could be obtained from 1000 mg of crude Macleaya cordata alkaloid at one time by this method. According to the calculation of external standard method, the purity of them were 99.77% and 99.73% respectively determined by UPLC. The structure of the two target product was identified by comparison with standards, ¹H NMR and ¹³C NMR. The structure data of the separated products were in agreement with the literature. The method is suitable for the mass preparation of sanguinarine and chelerythrine, because it has many advantages such as simple post-treatment, low cost, high purity of separation products and strong practicability.
- high speed counter-current chromatography,
- Macleaya cordata,
- sanguinarine,
- chelerythrine,
- preparation

FullText(HTML)

References (30)

References

[1]	中国医学科学院药物研究所. 常用中草药栽培手册[M]. 北京: 人民卫生出版社, 1971: 75−77. Chinese Academy of Medical Sciences. Cultivation manual of commonly used Chinese herbal medicine[M]. BeiJing: People's Medical Publishing House, 1971: 75−77.
[2]	钟明. 博落回主要生物碱的分离、纯化及生物活性研究[D]. 长沙: 中南大学, 2011: 1−10. ZHONG M. Separation, purification and bioactivities of principal alkaloids from Macleaya cordata (Willd) R. Br. [D]. Changsha: Central South University, 2011: 1−10.
[3]	QING Z X, XU Y Q, YANG P, et al. Study on alkaloids of fruit from Macleaya cordata[J]. Journal of Chinese Medicinal Materials,2016,39(2):312−314.
[4]	FENG G, ZHANG J, LI X W, et al. Insecticidal activity of alkaloids from Macleaya microcarpa against several species of insect pests[J]. Journal of Tropical and Subtropical Botany,2008,5(3):39−42.
[5]	王朝元, 童胜兰, 胡鑫, 等. 博落回生物碱成分及其抗菌活性的研究[J]. 中南民族大学学报(自然科学版),2015,34(1):33−39. [WANG C Y, TONG S L, HU X, et al. Studies on alkaloid ingredients of Macleaya cordata and their antibacterial activity[J]. Journal of South-central University for Nationalities(Nat Sci Edition),2015,34(1):33−39.
[6]	朱艳华, 王超, 阎雪莹. 博落回总碱对SGC 7901细胞毒性的研究[J]. 中华中医药学刊,2013,31(3):475−476. [ZHU Y H, WANG C, YAN X Y. Study on cytotoxicity of total alkaloids of Macleaya cordata on SGC 7901[J]. Chinese Archives of Traditional Chinese Medicine,2013,31(3):475−476.
[7]	SAI C M, WANG J A, LI B J, et al. Isolation and identification of alkaloids from Macleaya microcarpa by UHPLC-Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo[J]. BMC Chemistry,2020,14(1):124−131.
[8]	曾建国, 刘华. 博落回主要功能成分及其在动物生产中的应用[J]. 饲料工业,2019,40(7):1−6. [ZENG J G, LIU H. Main functional components of Macleaya cordata and its application in animal production[J]. Feed Industry,2019,40(7):1−6.
[9]	张灵梅, 朱晋佳, 杨玲媛, 等. 博落回在畜禽生产中的应用研究[J]. 激光生物学报,2020,29(2):21−27. [ZHANG L M, ZHU J J, YANG L Y, et al. A study on the application of Macleaya cordata in livestock production[J]. Acta Laser Biology Sinica,2020,29(2):21−27.
[10]	肖俐, 易键, 赵静, 等. 博落回提取物对大鼠急性酒精性肝损伤的保护作用[J]. 中南药学,2011,9(7):485−489. [XIAO L, YI J, ZHAO J, et al. Protective effect of Macleaya cordata extract on alcohol-induced acute hepatic injury in rats[J]. Central South Pharmacy,2011,9(7):485−489. doi: 10.3969/j.issn.1672-2981.2011.07.002
[11]	陈伟, 张锐, 雷思敏, 等. 博落回化学成分及其药理活性研究进展[J]. 中国实验方剂学杂志,2020,26(3):243−250. [CHEN W, ZHANG R, LEI S M, et al. Advances in chemical constituents and bioactivities of Macleaya cordata[J]. Chinese Journal of Experimental Traditional Medical Formulae,2020,26(3):243−250.
[12]	叶冯芝, 冯锋, 柳文媛. 博落回的生物碱成分[J]. 中国中药杂志,2009,34(13):1683−1686. [YE F Z, FENG F, LIU W Y. Alkaloids from Macleaya cordata[J]. China Journal of Chinese Materia Medical,2009,34(13):1683−1686.
[13]	FAEHNRICH B, PASTOR A, HEIDE C, et al. Effects of isoquinoline alkaloids from Macleaya cordata on physiological, immunological and inflammatory parameters in healthy beagles: Alkaloids in dog nutrition[J]. Journal of Animal Physiology and Animal Nutrition,2019,103(2):661−667.
[14]	杨佳, 陈旻, 李明花, 等. 血根碱对人肺腺癌细胞迁移侵袭和Wnt/β-catenin信号通路的影响[J]. 肿瘤防治研究,2019,46(12):1057−1061. [YANG J, CHEN M, LI M H, et al. Effects of sanguinarine on invasion, migration and Wnt/β-catenin signaling pathway of lung adenocarcinoma cells[J]. Cancer Research Prevention Treatment,2019,46(12):1057−1061.
[15]	康伟松, 程辟, 曾建国. 血根碱、白屈菜红碱离子对化合物的体外抗菌活性研究[J]. 中南药学,2014,12(5):406−410. [KANG W S, CHENG P, ZENG J G, et al. In vitro antibacterial activity of sanguinarine and chelerythrine ion-pair compounds[J]. Central South Pharmacy,2014,12(5):406−410. doi: 10.7539/j.issn.1672-2981.2014.05.006
[16]	姚雯, 杨天衡, 刘学波. 血根碱清除自由基及抑制生物大分子氧化的作用[J]. 食品科学,2014,35(9):137−141. [YAO W, YANG T H, LIU X B. Sanguinarine scavenges free radicals and protects against oxidative damage of biological macromolecules[J]. Food Science,2014,35(9):137−141. doi: 10.7506/spkx1002-6630-201409028
[17]	王荣, 刘艳芳, 王超然, 等. 生物碱的高效液相色谱分离分析与纯化制备研究进展[J]. 分析测试学报,2019,38(5):586−594. [WANG R, LIU Y F, WANG C R, et al. Research progress on high performance liquid chromatography in analysis an preparation of alkaloids[J]. Jouranl of Instrumental Analysis,2019,38(5):586−594. doi: 10.3969/j.issn.1004-4957.2019.05.014
[18]	LI L Q, HUANG M Y, SHAO J L, et al. Rapid determination of alkaloids in Macleaya cordata using ionic liquid extraction followed by multiple reaction monitoring UPLC-MS/MS analysis[J]. J Pharm Biomed Anal,2017,135(Complete):61−66.
[19]	邓霖芳, 袁帅, 刘江云, 等. 博落回提取物中血根碱的离子交换树脂分离纯化工艺研究[J]. 中国药房,2019,16(30):2226−2231. [DENG L F, YUAN S, LIU J Y, et al. Study on separation and purification technology of sanguinarine from the extract of Macleaya cordata by ion exchange resin[J]. China Pharmacy,2019,16(30):2226−2231.
[20]	余坤, 向锋, 卿志星, 等. 博落回根中生物碱的分离[J]. 中国药师,2017,20(11):1903−1906. [YU K, XIANG F, QING Z X, et al. Separation of alkaloids from the root of Macleaya cordata[J]. Chian Pharmacist,2017,20(11):1903−1906. doi: 10.3969/j.issn.1008-049X.2017.11.001
[21]	杨鹏, 向锋, 曾建国, 等. 博落回鲜叶中生物碱类化学成分的分离与结构鉴定[J]. 中国现代中药,2017,19(10):1371−1375. [YANG P, XIANG F, ZENG J G, et al. Isolation and identification of alkaloids from the fresh leaves of Macleaya cordata[J]. Modern Chinese Medicine,2017,19(10):1371−1375.
[22]	SCHWARZ M, WEBER F, DURAN G E, et al. HPLC-DAD-MS and antioxidant profile of fractions from amontillado sherry wine obtained using high-speed counter-current chromatography[J]. Foods,2021,10(1):131−131. doi: 10.3390/foods10010131
[23]	MENG J, LI Q Y, CAO Z Y, et al. Rapid screening and separation of active compounds against α-amylase fromToona sinensis by ligand fishing and high-speed counter-current chromatography[J]. International Journal of Biological Macromolecules,2021,174:270−277. doi: 10.1016/j.ijbiomac.2021.01.195
[24]	吴梦琪, 黄海, 蔡狄宏, 等. 大孔吸附树脂-高速逆流色谱法分离纯化苦水玫瑰花渣中的鞣花酸[J]. 食品工业科技,2021,42(5):182−187. [WU M Q, HUANG H, CAI D H, et al. Separation and purification of ellagic acid from rosa setate x rosa rugosa waste by macroporous resin and high-speed counter current chromatography[J]. Science and Technology of Food Industry,2021,42(5):182−187.
[25]	宋道光, 樊鑫宇, 徐顺连, 等. 高速逆流色谱法从小叶金钱草中分离制备三种黄酮苷类化合物[J]. 食品工业科技,2019,40(13):29−33. [SONG D G, FAN X Y, XU S L, et al. Preparation of three flavonoid glycosides compounds from Hydrocotyle sibthorpioides Lam. by high speed counter current chromatography[J]. Science and Technology of Food Industry,2019,40(13):29−33.
[26]	潘汇, 蔡为荣, 谢亮亮, 等. 运用HSCCC法分离纯化荷叶中三种黄酮及抗氧化活性[J]. 食品工业科技,2018,39(16):161−165. [FAN H, CAI W R, XIE L L, et al. Isolation and purification of three flavonoid lotus leaf by HSCCC and antioxidant activity evaluation[J]. Science and Technology of Food Industry,2018,39(16):161−165.
[27]	LIU Y, WANG W, CHE F, et al. Isolation and purification of alkaloids from the fruits of Macleaya cordata by ionic-liquid-modified high-speed counter-current chromatography[J]. Journal of Separation Science,2020,43(12):1005−1017.
[28]	IFTIKHAR A, JING C L, LI C, et al. Efficient extraction and purification of benzo[c]phenanthridine alkaloids from Macleaya cordata (Willd) R. Br. by combination of ultrahigh pressure extraction and pH-zone-refining counter-current chromatography with anti-breast cancer activity in vitro[J]. Phytochemical Analysis,2020,13(7):1−10.
[29]	LIU Q, SUN C, MENG F, et al. Preparative separation of chelerythrine and canguinarine from Macleaya cordata by pH-Zone-Refining counter-current chromatography[J]. Journal of Liquid Chromatography & Related Technologies,2015,38(20):1789−1793.
[30]	MAREK R, TOUSEK J, DOSTAL J, et al. ¹H NMR and¹³C NMR study of quaternary benzo[c]phenanthridine alkaloids[J]. Magnetic Resonance in Chemistry,1999,37(11):781−787. doi: 10.1002/(SICI)1097-458X(199911)37:11<781::AID-MRC556>3.0.CO;2-H

[1]	ZHANG Ledao, LV Junli, LI Junfang, ZENG Youhua, REN Guangyue, MA Li. Effects of Water Temperature and Steaming Time on Water State and Textural Characteristics of Naked Oats Noodles[J]. Science and Technology of Food Industry, 2021, 42(12): 19-23. DOI: 10.13386/j.issn1002-0306.2020080201
[2]	Jianting YANG, Sunyan WANG, Jinpeng HU, Ligong ZHAI, Yan LIU. Storage Life Prediction of Pickled White Ginger with Sugar and Vinegar according to Texture Evaluation[J]. Science and Technology of Food Industry, 2021, 42(8): 282-287. DOI: 10.13386/j.issn1002-0306.2020080111
[3]	LUAN Lin-lin, LU Hong-mei, CHEN Li, YANG Feng-yi. Cooking Quality and Textural Characteristics of Coix Seed during Storage[J]. Science and Technology of Food Industry, 2019, 40(10): 68-72,77. DOI: 10.13386/j.issn1002-0306.2019.10.012
[4]	HE Li-chao, MA Su-min, LI Cheng-liang, YANG Hai-yan, SUN Xiu-xiu, WU Wen-min, JIN Guo-feng. Effect of different cooking time on the textural profile and lipid composition of hard-boiled egg[J]. Science and Technology of Food Industry, 2018, 39(6): 25-30,37. DOI: 10.13386/j.issn1002-0306.2018.06.005
[5]	HUANG Mei-hua, LIANG Xiao-jun, HE Quan-guang, ZHANG E-zhen, DAN Ming, QIN Ren-yuan, YANG Zai-wei, HUANG Zhen-yong. Study on the texture analysis conditions of banana jam[J]. Science and Technology of Food Industry, 2018, 39(4): 1-5,11.
[6]	HE Quan-guang, HUANG Mei-hua, ZHANG E-zhen, XIN Ming, HUANG Mao-kang, QIN Ren-yuan, HUANG Zhen-yong. Optimization for mango texture profile analysis and characterization of texture to different maturaity of mango[J]. Science and Technology of Food Industry, 2016, (18): 122-126. DOI: 10.13386/j.issn1002-0306.2016.18.015
[7]	TIAN Li-juan, XU Yan-shun, JIANG Qi-xing, XIA Wen-shui. Effect of moisture content on the texture and color of instant crispy crucian carp[J]. Science and Technology of Food Industry, 2015, (16): 104-107. DOI: 10.13386/j.issn1002-0306.2015.16.013
[8]	LIU Yan-fang, LI Bian-sheng, RUAN Zheng, HUANG Jia-rong, LUO Yong-bao. Effect of frozen storage time on color and texture properties of cantonese sweet-paste-filling buns[J]. Science and Technology of Food Industry, 2015, (07): 83-87. DOI: 10.13386/j.issn1002-0306.2015.07.008
[9]	LI Lin- ge, SHEN Yong-qi, TONG Chang-qing. Effects of boiling time on texture of Ruditapes philippinarum and characteristic of its boiled liquids[J]. Science and Technology of Food Industry, 2015, (01): 353-355. DOI: 10.13386/j.issn1002-0306.2015.01.066
[10]	Study on texture improving process of ready-to-eat smoked tilapia fillets[J]. Science and Technology of Food Industry, 2013, (12): 122-125. DOI: 10.13386/j.issn1002-0306.2013.12.079

Supplements (0)

Cited By

Cited by

Periodical cited type(4)

1.	季佳琪，李明初，李冬霞，谭雅宁，高爽，王颉，牟建楼. 高温蒸煮结合蜗牛酶法改性葡萄皮不溶性膳食纤维工艺优化及体外降血糖作用. 食品工业科技. 2024(16): 249-258 . 本站查看
2.	林良美，肖少香，张丽红. 响应面优化复合酶法提取红薯皮膳食纤维. 粮食科技与经济. 2024(04): 96-100+115 .
3.	竹娟，王译晗，陈立莉，曲文鑫，刘荣. 芍药花提取物中黄酮的测定及其体外抗氧化和降脂活性研究. 天然产物研究与开发. 2024(11): 1838-1844+1899 .
4.	赵习爱，傅婧，任娟蕊. 燕麦萌动对膳食纤维结构和功能的影响. 食品与发酵工业. 2024(24): 229-237 .