Profiling and Characterization of Herbal Medicine and its Metabolites Using LC–MS
Zeper Abliz
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorRuiping Zhang
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorPing Geng
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorDongmei Dai
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorJiuming He
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorJian Liu
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorZeper Abliz
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorRuiping Zhang
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorPing Geng
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorDongmei Dai
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorJiuming He
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorJian Liu
Key Laboratory of Bioactive Substances and Resource Utilization of Chinese, Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050 China
Search for more papers by this authorMingshe Zhu
Department of Biotransformation, Bristol-Myers Squibb Research and Development, Princeton, New Jersey, USA
Search for more papers by this authorSummary
This chapter contains sections titled:
-
Introduction
-
Characterization of Chemical Constituents in Chinese Herbal Medicine
-
Profiling the Integral Metabolism of Herbal Medicine
-
Conclusions
-
Acknowledgment
-
References
REFERENCES
- Ablajan K, Abliz Z, Shang XY, He JM, Zhang RP, Shi JG. Structural characterization of flavonol 3,7-di-O-glycosides and determination of the glycosylation position by using negative ion electrospray ionization tandem mass spectrometry. J Mass Spectrom 2006; 41: 352–360.
- Cai Z, Lee F, Wang X, Yu W. A capsule review of recent studies on the application of mass spectrometry in the analysis of Chinese medicinal herbs. J Mass Spectrom 2002; 37: 1013–1024.
- Chang Y, Abliz Z, Wang MZ. New techniques of tandem mass spectrometry and its application in the study of drug metabolism. Acta Pharm Sin 2000; 35: 73–78.
- Chen P, Li C, Liang SP, Song GQ, Sun Y, Shi YH, Xu SL, Zhang JW, Sheng SQ, Yang YM, Li M. Characterization and quantification of eight water-soluble constituents in tubers of Pinellia ternata and in tea granules from the Chinese multiherb remedy Xiaochaihu-tang. J Chromatogr B 2006; 843: 183–193.
- Chung VQ, Tattersall M, Cheung HT. Interactions of a herbal combination that inhibits growth of prostate cancer cells. Cancer Chemother Pharmacol 2004; 53: 384–390.
- Crespy V, Morand C, Besson C, Cotelle N, Vezin H, Demigne C, Remesy C. The splanchnic metabolism of flavonoids highly differed according to the nature of the compound. Am J Physiol Gastrointest Liver Physiol 2003; 284: G980–G988.
- Crespy V, Morand C, Manach C, Besson C, Demigne C, Remesy C. Part of quercetin absorbed in the small intestine is conjugated and further secreted in the intestinal lumen. Am J Physiol Gastrointest Liver Physiol 1999; 277: G120–G126.
- Cui LJ, Abliz Z, Xia M, Zhao LY, Gao S, He WY, Xiang Y, Liang F, Yu SS. On-line identification of phenanthroindolizidine alkaloids in a crude extract from Tylophora atrofolliculata by liquid chromatography combined with tandem mass spectrometry. Rapid Commun Mass Spectrom 2004; 18: 184–190.
- Cuyckens F, Claeys M. Determination of the glycosylation site in flavonoid mono-O-glycosides by collision-induced dissociation of electrospray-generated deprotonated and sodiated molecules. J Mass Spectrom 2005; 40: 364–372.
- Cuyckens F, Rozenberg R, de Hoffmann E, Claeys M. Structure characterization of flavonoid O-diglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry. J Mass Spectrom 2001; 36: 1203–1210.
- Dai DM, He JM, Sun RX, Zhang RP, Haji AA, Abliz Z. Nuclear magnetic resonance and liquid chromatography–mass spectrometry combined with an incompleted separation strategy for identifying the natural products in crude extract. Anal Chim Acta 2009; 632: 221–228.
- Day AJ, Bao Y, Morgan MR, Williamson G. Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic Biol Med 2000; 29: 1234–1243.
- Day AJ, Gee JM, DuPont MS, Johnson IT, Williamson G. Absorption of quercetin-3-glucoside and quercetin-4′-glucoside in the rat small intestine: The role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter. Biochem Pharmacol 2003; 65: 1199–1206.
- Domon B, Costello CE. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconj J 1988; 5: 397–409.
- Ferreres F, Llorach R, Gil-Izquierdo A. Characterization of the interglycosidic linkage in di-, tri-, tetra- and pentaglycosylated flavonoids and differentiation of positional isomers by liquid chromatography/electrospray ionization tandem mass spectrometry. J Mass Spectrom 2004; 39: 312–321.
- Geng P, Zhang RP, Haji AA, He JM, Qu K, Zhu HB. Fast profiling of the integral metabolism of flavonols in the active fraction of Gossypium herbaceam L. using liquid chromatography/multi-stage tandem mass spectrometry. Rapid Commun Mass Spectrom 2007; 21: 1877–1888.
- Graf BA, Mullen W, Caldwell ST, Hartley RC, Duthie GG, Lean ME, Crozier A, Edwards CA. Disposition and metabolism of [2-14C] quercetin-4′-glucoside in rats. Drug Metab Dispos 2005; 33: 1036–1043.
-
Hollman, PC H, Arts ICW. Flavonols, flavones and flavanols—nature, occurrence and dietary burden. J Sci Food Agric 2000; 80: 1081–1093.
10.1002/(SICI)1097-0010(20000515)80:7<1081::AID-JSFA566>3.0.CO;2-G CAS Web of Science® Google Scholar
- Lee KH. Research and future trends in the pharmaceutical development of medicinal herbs from Chinese medicine. Public Health Nutr 2000; 3: 515–522.
- Li B, Abliz Z, Fu GM, Tang MJ, Yu SS. Characteristic fragmentation behavior of some glucuronide-type triterpenoid saponins using electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 2005; 19: 381–390.
- Li B, Abliz Z, Tang MJ, Fu GM, Yu SS. Rapid structural characterization of triterpenoid saponins in crude extract from Symplocos chinensis using liquid chromatography combined with electrospray ionization tandem mass spectrometry. J Chromatogr A 2006; 1101: 53–62.
- Liang F, Li LJ, Abliz Z, Yang YC, Shi JG. Structural characterization of steroidal sapoins by electrospray ionization and fast-atom bombardment tandem mass spectrometry. Rapid Commun Mass Spectrom 2002; 16: 1168–1173.
- Liu Y, He J, Zhang R, Shi J, Abliz Z. Study of the characteristic fragmentation behavior of hydroquinone glycosides by electrospray ionization tandem mass spectrometry with optimization of collision energy. J Mass Spectrom 2009; 44: 1182–1187.
- Liu YZ, Liang F, Cui LJ, Xia M, Zhao LY, Yang YC, Shi JG, Abliz Z. Multi-stage mass spectrometry of furostanol saponins combined with electroapray ionization in positive and negative ion modes. Rapid Commun Mass Spectrom 2004; 18: 235–238.
- Ma YL, Cuyckens F, Van den Heuvel H, Claeys M. Mass spectrometric methods for the characterisation and differentiation of isomeric O-diglycosyl flavonoids. Phytochem Anal 2001; 12: 159–165.
- Moon JH, Tsushida T, Nakahara K, Terao J. Identification of quercetin 3-O-β-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Radic Biol Med 2001; 30: 1274–1285.
- Mullen W, Boitier A, Stewart AJ, Crozier A. Flavonoid metabolites in human plasma and urine after the consumption of red onions: Analysis by liquid chromatography with photodiode array and full scan tandem mass spectrometric detection. J Chromatogr A 2004; 1058: 163–168.
- Nemeth K, Plumb GW, Berrin JG, Juge N, Jacob R, Naim HY, Williamson G, Swallow DM, Kroon PA. Deglycosylation by small intestinal epithelial cell β-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans. Eur J Nutr 2003; 42: 29–42.
- O'Leary KA, Day AJ, Needs PW, Mellon FA, O'Brien NM, Williamson G. Metabolism of quercetin-7- and quercetin-3-glucuronides by an in vitro hepatic model: The role of human β-glucuronidase, sulfotransferase. Biochem Pharmacol 2003; 65: 479–491.
- Tang HM. A study on material base of acorus Tatarinowii Schott for cerebral disease. Li shi zhen Med and Mater Med Res 2002; 13: 1–2.
- van der Woude H, Boersma MG, Alink GM, Vervoort J, Rietjens IM. Consequences of quercetin methylation for its covalent glutathione and DNA adduct formation. Chem Biol Interact 2006; 160: 193–203.
- van der Woude H, Boersma MG, Vervoort J, Rietjens IM. Identification of 14 quercetin phase II mono- and mixed conjugates and their formation by rat and human phase II in vitro model systems. Chem Res Toxicol 2004; 17: 1520–1530.
-
Wang XJ, Sun WJ, Sun H, Zhou DX, Lu HT, Wang P, Liu L. Effects of formula compatibility of Yin Chen Hao Tang on the constituents absorbed into blood of rat. Chin J Nat Med 2008; 6: 43–47.
10.3724/SP.J.1009.2008.00043 Google Scholar
- Wang YL, Liang YZ, Chen BM, He YK, Li BY, Hu QN. LC-DAD-APCI-MS-based screening and analysis of the absorption and metabolite components in plasma from a rabbit administered an oral solution of Dang gui. Anal Bioanal Chem 2005; 383: 247–254.
- Wei YJ, Li P, Shu B, Song Y. Identification of chemical and metabolic components of Fu Fang Dan Shen prescription by high performance liquid chromatography–electrospray ion trap mass spectrometry. Chin J Anal Chem 2007; 35: 13–18.
- Williamson G, Day AJ, Plumb GW, Couteau D. Human metabolic pathways of dietary flavonoids and cinnamates. Biochem Soc Trans 2000; 28: 16–22.
- Wu CS, Sheng YX, Zhang YH, Zhang JL, Guo BL. Identification and characterization of active compounds and their metabolites by high-performance liquid chromatography/Fourier transform ion cyclotron resonance mass spectrometry after oral administration of a herbal extract of Epimedium koreanum Nakai to rats. Rapid Commun Mass Spectrom 2008; 22: 2813–2824.
- Xiang Y, Abliz Z, Li LJ, Huang X, Yu SS. Study on structural characteristic features of phenanthriondolizidine alkaloids by fast atom bombardment with tandem mass spectrometry. Rapid Commun Mass Spectrom 2002: 16(17): 1668–1674.
- Yang M, Sun J, Lu Z, Chen GT, Guan SH, Liu X, Jiang BH, Ye M, Guo DA. Phytochemical analysis of traditional Chinese medicines (TCM) using liquid chromatography coupled with mass spectrometry. J Chromatogr A 2009; 1216: 2045–2062.
- Zhang JL, Cui M, He Y, Yu HL, Guo DA. Chemical fingerprint and metabolic fingerprint analysis of Danshen injection by HPLC-UV and HPLC-MS methods. J Pharm Biomed Anal 2005; 36: 1029–1035.
- Zhao X, Qiang GH, Guo Y, Zhao XF, Liu Q, Zheng XH. The new metabolites of notoginseng in compound Dan Shen Dripping pills in human plasma. J of Chin Mass Spectrom Soc 2007; 28: 24–26.
- Zhu BT, Ezell EL, Liehr JG. Catechol-O-methyltransferase-catalyzed rapid O-methylation of mutagenic flavonoids. Metabolic inactivation as a possible reason for their lack of carcinogenicity in vivo. J Biol Chem 1994; 269: 292–299.