中性解吸电喷雾萃取电离质谱分析研究炙甘草炮制过程中的品质变化机制

刘莹; 余琳琳; 方小伟; 陈焕文; 吴栋

doi:10.7538/zpxb.2024.0195

[1]

DING Y, BRAND E, WANG W, ZHAO Z. Licorice: resources, applications in ancient and modern times[J]. Journal of Ethnopharmacology, 2022, 298: 115 594.

[2]

WANG C, ZHANG J, PEI Y, LI C, LI Y, CHEN S, WANG Z. Visualized electrochemiluminescence detection of trace copper in practical food samples[J]. Food Chemistry, 2024, 451: 139 461.

[3]

LI Y, XIE Z, HUANG Y, ZENG J, YANG C, YUAN L, WANG Y, LI Y. Integrated metabolomic and transcriptomic analysis provides insights into the flavonoid formation in different Glycyrrhiza species[J]. Industrial Crops and Products, 2024, 208: 117 796.

[4]

KUŚ P M. Honey as source of nitrogen compounds: aromatic amino acids, free nucleosides and their derivatives[J]. Molecules, 2020, 25(4): 847 .

[5]

SUN P, CHEN H, FAN X, WANG J, LU L, YANG G, LIU J, YAO W, DING F, DING J, LIU J, LU T, CHEN L. Exploring the effective components of honey-processed licorice (Glycyrrhiza uralensis Fisch.) in attenuating Doxorubicin-induced myocardial cytotoxicity by combining network pharmacology and in vitro experiments[J]. Journal of Ethnopharmacology, 2024, 329: 118 178.

[6]

OTA M, XU F, LI Y, SHANG M, MAKINO T, CAI S. Comparison of chemical constituents among licorice, roasted licorice, and roasted licorice with honey[J]. Journal of Natural Medicines, 2018, 72(1): 80 - 95 .

[7]

ZHOU Q, ZHANG S, GENG X, JIANG H, DAI Y, WANG P, HUA M, GAO Q, LANG S, HOU L, SHI D, ZHOU M. Antioxidant effects of roasted licorice in a zebrafish model and its mechanisms[J]. Molecules, 2022, 27(22): 7 743.

[8]

CUI X, LOU L, ZHANG Y, YAN B. Study of the distribution of Glycyrrhiza uralensis production areas as well as the factors affecting yield and quality[J]. Scientific Reports, 2023, 13(1): 5 160.

[9]

YANG F, CHU T, ZHANG Y, LIU X, SUN G, CHEN Z. Quality assessment of licorice (Glycyrrhiza glabra L.) from different sources by multiple fingerprint profiles combined with quantitative analysis, antioxidant activity and chemometric methods[J]. Food Chemistry, 2020, 324: 126 854.

[10]

PENG C, ZHU Y, YAN F, SU Y, ZHU Y, ZHANG Z, ZUO C, WU H, ZHANG Y, KAN J, PENG D. The difference of origin and extraction method significantly affects the intrinsic quality of licorice: a new method for quality evaluation of homologous materials of medicine and food[J]. Food Chemistry, 2021, 340: 127 907.

[11]

TAN G, ZHU Z, ZHANG H, ZHAO L, LIU Y, DONG X, LOU Z, ZHANG G, CHAI Y. Analysis of phenolic and triterpenoid compounds in licorice and rat plasma by high-performance liquid chromatography diode-array detection, time-of-flight mass spectrometry and quadrupole ion trap mass spectrometry[J]. Rapid Communications in Mass Spectrometry, 2010, 24(2): 209 - 218 .

[12]

XU T, YANG M, LI Y, CHEN X, WANG Q, DENG W, PANG X, YU K, JIANG B, GUAN S, GUO D. An integrated exact mass spectrometric strategy for comprehensive and rapid characterization of phenolic compounds in licorice[J]. Rapid Communications in Mass Spectrometry, 2013, 27(21): 2 297-2 309.

[13]

FARAG M A, PORZEL A, WESSJOHANN L A. Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC-MS, LC-MS and 1D NMR techniques[J]. Phytochemistry, 2012, 76: 60 - 72 .

[14]

刘志荣, 张明童, 谢楠, 张平, 马潇, 郭朝晖. 改进QuEChERS-超高效液相色谱-串联质谱法同时测定甘草中86种农药残留[J]. 质谱学报, 2020, 41(6): 624 - 636 . doi: 10.7538/zpxb.2019.0116 LIU Zhirong, ZHANG Mingtong, XIE Nan, ZHANG Ping, MA Xiao, GUO Zhaohui. Simultaneous determination of 86 pesticide residues in Glycyrrhiza uralensis by improved QuEChERS-UPLC-MS/MS[J]. Journal of Chinese Mass Spectrometry Society, 2020, 41(6): 624 - 636 (in Chinese). doi: 10.7538/zpxb.2019.0116

[15]

席绍峰, 李慧勇, 谭建华, 徐汉虹, 王继才, 熊小婷, 赵田甜, 冼燕萍, 郭新东. SPE-UPLC-Q-TOF MS测定育发化妆品中人参和甘草类功效成分[J]. 质谱学报, 2015, 36(4): 341 - 349 . doi: 10.7538/zpxb.youxian.2015.0022 XI Shaofeng, LI Huiyong, TAN Jianhua, XU Hanhong, WANG Jicai, XIONG Xiaoting, ZHAO Tiantian, XIAN Yanping, GUO Xindong. Determination of active constituents of Ginseng and Glycyrrhizae in hair growth cosmetics by SPE-UPLC-Q-TOF MS[J]. Journal of Chinese Mass Spectrometry Society, 2015, 36(4): 341 - 349 (in Chinese). doi: 10.7538/zpxb.youxian.2015.0022

[16]

郭倩池, 王康宇, 张龄月, 郭云龙, 贡济宇, 高文义. 基于UHPLC-Q-Orbitrap/MS鉴定当归四逆颗粒化学成分[J]. 质谱学报, 2024, 45(3): 432 - 446 . GUO Qianchi, WANG Kangyu, ZHANG Lingyue, GUO Yunlong, GONG Jiyu, GAO Wenyi. Identification of chemical components of Danggui Sini Granules by UHPLC-Q-Orbitrap/MS[J]. Journal of Chinese Mass Spectrometry Society, 2024, 45(3): 432 - 446 (in Chinese).

[17]

杨飞祥, 钟凌云, 陈焕文, 方小伟. 内部萃取电喷雾电离质谱研究枳壳炮制前后的化学成分[J]. 质谱学报, 2024, 45(6): 763 - 772 . YANG Feixiang, ZHONG Lingyun, CHEN Huanwen, FANG Xiaowei. Research of chemical comparison of Aurantii Fructus before and after processing by internal extractive electrospray ionization mass spectrometry[J]. Journal of Chinese Mass Spectrometry Society, 2024, 45(6): 763 - 772 (in Chinese).

[18]

吴栋, 于腾辉, 李享, 崔萌, 郝影宾, 刘丽华, 罗丽萍. 中性解吸-电喷雾萃取电离质谱直接分析水涝胁迫下烟草的代谢产物[J]. 分析化学, 2020, 48(1): 121 - 128 . WU Dong, YU Tenghui, LI Xiang, CUI Meng, HAO Yingbin, LIU Lihua, LUO Liping. Direct analysis of Nicotiana tabacum metabolites under waterlogging stress by neutral desorption-extractive electrospray ionization mass spectrometry[J]. Chinese Journal of Analytical Chemistry, 2020, 48(1): 121 - 128 (in Chinese).

[19]

HUANG X, FANG X, ZHANG X, DAI X, GUO X, CHEN H, LUO L. Direct detection of chloramphenicol in honey by neutral desorption-extractive electrospray ionization mass spectrometry[J]. Analytical and Bioanalytical Chemistry, 2014, 406(29): 7 705-7 714.

[20]

WU Z, CHINGIN K, CHEN H, ZHU L, JIA B, ZENOBI R. Sampling analytes from cheese products for fast detection using neutral desorption extractive electrospray ionization mass spectrometry[J]. Analytical and Bioanalytical Chemistry, 2010, 397(4): 1 549-1 556.

[21]

WU D, MING H, WU W, YU W, ZHANG G, GU J, CUI M, HUANG X, NING F, LUO L. In situ neutral desorption-extractive electrospray ionization mass spectrometry reveals red-blue light promoted the accumulation of amino acids and polyphenols in Anoectochilus roxburghii[J]. Journal of Food Composition and Analysis, 2024, 125: 105 761.

[22]

ZHANG X, LIU Y, ZHANG J, HU Z, HU B, DING L, JIA L, CHEN H. Neutral desorption extractive electrospray ionization mass spectrometry for fast screening sunscreen agents in cream cosmetic products[J]. Talanta, 2011, 85(3): 1 665-1 671.

[23]

DING J, GU H, YANG S, LI M, LI J, CHEN H. Selective detection of diethylene glycol in toothpaste products using neutral desorption reactive extractive electrospray ionization tandem mass spectrometry[J]. Analytical Chemistry, 2009, 81(20): 8 632-8 638.

[24]

商杰. 建昌帮蜜炙甘草的化学成分、工艺及质量标准研究[D]. 南昌: 江西中医药大学, 2024.

[25]

RINGNÉR M. What is principal component analysis?[J]. Nature Biotechnology, 2008, 26(3): 303 - 304 .

[26]

LU W, JIANG Q, SHI H, NIU Y, GAO B, YU L. Partial least-squares-discriminant analysis differentiating Chinese wolfberries by UPLC-MS and flow injection mass spectrometric (FIMS) fingerprints[J]. Journal of Agricultural and Food Chemistry, 2014, 62(37): 9 073-9 080.

[27]

WANG Z, LIU J, YANG Y, ZHU H. A review: the anti-inflammatory, anticancer and antibacterial properties of four kinds of licorice flavonoids isolated from licorice[J]. Current Medicinal Chemistry, 2020, 27(12): 1 997-2 011.

[28]

FU Y, LIU W, SOLADOYE O P. Towards innovative food processing of flavonoid compounds: insights into stability and bioactivity[J]. LWT, 2021, 150: 111 968.

[29]

JIANG C, GATES P J. Systematic characterisation of the fragmentation of flavonoids using high-resolution accurate mass electrospray tandem mass spectrometry[J]. Molecules, 2024, 29(22): 5 246.

[30]

WANG D, LIANG J, ZHANG J, WANG Y, CHAI X. Natural chalcones in Chinese materia medica: licorice[J]. Evidence-Based Complementary and Alternative Medicine, 2020, 2020(1): 3 821 248.

[31]

YU J, ZHANG D, LIANG Y, ZHANG Z, GUO J, CHEN Y, YAN Y, LIU H, LEI L, WANG Z, TANG Z, TANG Y, DUAN J A. Licorice-Yuanhua herbal pair induces ileum injuries through weakening epithelial and mucous barrier functions: saponins, flavonoids, and di-terpenes all involved[J]. Frontiers in Pharmacology, 2020, 11: 869 .

[32]

YANG J, LIU Y, CUI Z, WANG T, LIU T, LIU G. Analysis of free amino acid composition and honey plant species in seven honey species in China[J]. Foods, 2024, 13(7): 1 065.

[33]

CHENG C, BRINZARI T V, HAO Z, WANG X, PAN L. Understanding methyl salicylate hydrolysis in the presence of amino acids[J]. Journal of Agricultural and Food Chemistry, 2021, 69(21): 6 013-6 021.

[34]

GENG Z, WANG J, ZHU L, YU X, ZHANG Q, LI M, HU B, YANG X. Metabolomics provide a novel interpretation of the changes in flavonoids during sea buckthorn (Hippophae rhamnoides L.) drying[J]. Food Chemistry, 2023, 413: 135 598.

[35]

XU P, YANG Z, LI X, ZHANG Z, YANG J, YUAN T, YUSUBJONOVNA M M, ElGAMAL R, WU Z. Effects of different drying methods on drying characteristics and quality of silage Broussonetia papyrifera L[J]. LWT-Food Science and Technology, 2024, 210: 116 872.

[36]

TAKLA S S, SHAWKY E, MAHGOUB Y A, DARWISH R S. Tracking the effect of roasting and fermentation on the metabolites of licorice root (Glycyrrhiza glabra L.) using UPLC-MS analysis combined with multivariate statistical analysis[J]. BMC Complementary Medicine and Therapies, 2023, 23(1): 419 .

[37]

SHABKHIZ M A, EIKANI M H, BASHIRI SADR Z, GOLMOHAMMAD F. Superheated water extraction of glycyrrhizic acid from licorice root[J]. Food Chemistry, 2016, 210: 396 - 401 .

[38]

CHEN K, YANG R, SHEN F Q, ZHU H L. Advances in pharmacological activities and mechanisms of glycyrrhizic acid[J]. Current Medicinal Chemistry, 2020, 27(36): 6 219-6 243.

[39]

ONG E S, CHEONG J S H, GOH D. Pressurized hot water extraction of bioactive or marker compounds in botanicals and medicinal plant materials[J]. Journal of Chromatography A, 2006, 1 112(1/2): 92-102.

[40]

WANG R, LIN C, LIU J, YU F, GAO J, PAN X. Pressured microwave-assisted hydrolysis of crude glycyrrhizic acid for preparation of glycyrrhetinic acid[J]. Chinese Journal of Chemical Engineering, 2012, 20(1): 152 - 157 .

[41]

ZHANG X, GUO X, ZHAO P, ZHANG X, GAO W, LI X. Chemometric analysis of active compounds and antioxidant and α-glucosidase inhibitory activities for the quality evaluation of licorice from different origins[J]. Biomedical Chromatography, 2021, 35(12): e5215.