Chemical Transformation of Raw and Fermented Ziziphi Spinosae Semen Analyzed by UPLC-Q-Orbitrap MS/MS

doi:10.7503/cjcu20190055

Chem. J. Chinese Universities ›› 2019, Vol. 40 ›› Issue (8): 1614.doi: 10.7503/cjcu20190055

• Analytical Chemistry • Previous Articles Next Articles

Chemical Transformation of Raw and Fermented Ziziphi Spinosae Semen Analyzed by UPLC-Q-Orbitrap MS/MS

DU Chenhui¹, LI Ze¹, CUI Xiaofang¹, ZHANG Min², PEI Xiangping¹, ZHAN Haixian¹, YAN Yan²

1. School of Traditional Chinese Materia Medica, Shanxi University of Chinese Medicine, Taiyuan 030619, China;
2. Modern Research Center for Traditional Chinese Medicine, Shanxi University, Taiyuan 030006, China

Received:2019-01-18 Revised:2019-07-23 Online:2019-08-10 Published:2019-07-12
Supported by:
Supported by the National Natural Science Foundation of China(Nos.81603251, 81603289), the Zhendong Group Research Foundation of Shanxi Province, China(Nos.2014ZD0306, 2016ZD0105, 2016ZD0104), the Natural Science Foundation of Shanxi Province, China(No.2015011105), the Shanxi Collaborative Innovation Center for Comprehensive Development and Utilization of Jinyao Foundation, China(No.2017-JYXT-25) and the Science and Technology Innovation Group of Shanxi University of Chinese Medicine, China(No.2018-TD-009).

Abstract

Abstract: To elucidate the fermentation-induced chemical transformation mechanisms of secondary metabolites, the chemical difference between raw and fermented Ziziphi Spinosae Semen(SZR) using Poria cocos (Schw.) Wolf was revealed by integrating UPLC-Q-Orbitrap MS/MS techniques-based untargeted metabolomics. 24 chemical components were characterized in fermented Ziziphi Spinosae Semen(FSZR). The 7 differential marker compounds between SZR and FSZR were rapidly discovered by untargeted chemomics-based mining approach using OPLS-DA. Meanwhile, the relative contents of 24 chemical components were analyzed by t-Test, which was used to make metabolic pathway analysis, showing that deacetylate and deglycosylation were the major metabolic reaction under fermentation by Poria cocos. The result shows that the proposed strategy meets the technical demands for the overall chemical characterization of fermented herbal medicines, and therefore may be considered a promising approach for delving into the scientific basis in traditional fermentation of herbal medicines.

Key words: Ziziphi Spinosae Semen, Poria cocos(Schw.) Wolf., Fermentation, UPLC-Q-Orbitrap MS/MS, Biotransformation

CLC Number:

O657

TrendMD:

DU Chenhui, LI Ze, CUI Xiaofang, ZHANG Min, PEI Xiangping, ZHAN Haixian, YAN Yan. Chemical Transformation of Raw and Fermented Ziziphi Spinosae Semen Analyzed by UPLC-Q-Orbitrap MS/MS[J]. Chem. J. Chinese Universities, 2019, 40(8): 1614.

References 23

[1]	Huang Q., Zhang H., Xue D., Food Chem., 2017, 226, 89-94
[2]	Fu Y., Yin Z., Wu L., Yin C., World J. Microb. Biot., 2014, 30(3), 1019-1025
[3]	Limón R. I., Peñas E., Torino M. I., Martínez-Villaluenga C., Dueñas M., Frias J., Food Chem., 2015, 172, 343-352
[4]	Yang P. F., Liu C., Wang H. Q., Li J. C., Wang Z. Z., Xiao W., Chen R. Y., Chin. J. Chin. Mater. Med., 2014, 39(6), 1030-1033(杨鹏飞, 刘超, 王洪庆, 李家春, 王振中, 萧伟, 陈若芸. 中国中药杂志, 2014, 39(6), 1030-1033)
[5]	Li Y., Yang S., Li C., Yang W. Q., Wan D. G., Chin. Tradit. Herbal Drugs, 2012, 43(8), 1519-1522(李羿, 杨胜, 李晨, 杨万清, 万德光. 中草药, 2012, 43(8), 1519-1522)
[6]	Zhang Y., Hu G. S., Han Z. F., Xiao W., Wang Z. D., Bi Y. A., Jia J. M., Chin. J. Chin. Mater. Med., 2013, 38(9), 1355-1359(张杨, 胡高升, 韩志福, 萧伟, 王振东, 毕宇安, 贾景明. 中国中药杂志, 2013, 38(9), 1355-1359)
[7]	You Z. L., Xia Q., Liang F. R., Tang Y. J., Xu C. L., Huang J., Zhao L., Zhang W. Z., He J. J., J. Ethnopharmacol., 2010, 128(2), 419-423
[8]	Liu J., Zhai W. M., Yang Y. X., Shi J. L., Liu Q. T., Liu G. L., Fang N., Li J., Guo J. Y. Pharmacol. Biochem. Be., 2015, 128, 41-49
[9]	Alreza S. M., Bajpai V. K., Kang S. C., Food Chem. Toxicol., 2009, 47(9), 2374-2380
[10]	Li Q., Du C. H., Zhang M., Yan Y., Gao Y., Qin X. M., Chin. Tradit. Herbal Drugs, 2017, 48(10), 1936-1943(李强, 杜晨晖, 张敏, 闫艳, 高耀, 秦雪梅. 中草药, 2017, 48(10), 1936-1943)
[11]	Wang X., Xie M., J. Chin. Med. Assoc., 2004, 10(1), 35-37(王欣, 谢鸣. 中国实验方剂学杂志, 2004, 10(1), 35-37)
[12]	Cao W. C., Hai Y., Ren L., Liaoning J. Tradit. Chin. Med., 2018, 45(9), 1851-1853(曹文聪, 海英, 任路. 辽宁中医杂志, 2018, 45(9), 1851-1853)
[13]	Yu S. T., Liu H. X., Li K., Qin Z. G., Qin X. M., Zhu P., Li Z. Y., Acta Pharm. Sin., 2018, 53(4), 609-620(于舒婷, 刘海霞, 李昆, 秦正国, 秦雪梅, 朱平, 李震宇. 药学学报, 2018, 53(4), 609-620)
[14]	Xue Y., Li X. W., Li Z. Y., Zeng Z. P., Zhang F. S., Li A. P., Qin X. M., Peng B., Acta Pharm. Sin., 2015, (3), 340-347(薛英, 李晓伟, 李震宇, 曾祖平, 张福生, 李爱平, 秦雪梅, 彭冰. 药学学报, 2015, (3), 340-347)
[15]	Yan Y., Du C. H., Feng H. X., Qi J., Qin X. M., Chin. Tradit. Herbal Drugs, 2016, 47(17), 3109-3114(闫艳, 杜晨晖, 冯红霞, 戚进, 秦雪梅. 中草药, 2016, 47(17), 3109-3114)
[16]	Gong J. S., Wang Y., Zhang D. D., Li H., Zhang X. M., Zhang R. X., Lu Z. M., Xu Z. H., Shi J. S., Chem. Res. Chinese Universities, 2015, 31(1), 91-97
[17]	Milagres A. M. F., Sales R. M., Enzyme Microb. Tech., 2001, 28(6), 522-526
[18]	Gaskell J., Blanchette R. A., Stewart P. E., Bondurant S. S., Cullen D., Appl. Environ. Microb., 2016, 82(13), 3979-3987
[19]	Wu J., Wang C., Huang G., Zhao J., Wang X., Ji L., J. Food Sci. Tech., 2016, 53(8), 3225-3232
[20]	Machuca A., André F., Enzyme Microb. Tech., 2001, 29(6), 386-391
[21]	Rathbone D. A., Bruce N. C., Curr. Opin. Microbiol., 2002, 5(3), 274-281
[22]	Grishko V. V., Tolmacheva I. A., Pereslavtseva A. V., Chem. Nat. Compd., 2015, 51(1), 1-21
[23]	Arantes V., Milagres A. M. F., Filley T. R., Goodell B., J. Ind. Microbiol. Biot., 2011, 38(4), 541-555

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Chemical Transformation of Raw and Fermented Ziziphi Spinosae Semen Analyzed by UPLC-Q-Orbitrap MS/MS

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