Quasi-MSn identification of flavanone 7-glycoside isomers in Da Chengqi Tang by high performance liquid chromatography-tandem mass spectrometry

Chinese Medicine - Tập 4 Số 1 - 2009
Fengguo Xu1, Ying Liu2, Zunjian Zhang1, Chui‐Ping Yang1, Yuan Tian1
1Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, Nanjing, Jiangsu, 210009, PR, China
2Department of Pharmacy, Nanjing Municipal Hospital of Traditional Chinese Medicine, Nanjing, Jiangsu, 210001, PR, China

Tóm tắt

Abstract Background Da Chengqi Tang (DCT) is a common purgative formula in Chinese medicine. Flavanones are its major active compounds derived from Fructus Aurantii Immaturus. The present study developed an LC-MS/MS method to characterize two pairs of flavanone 7-glycoside isomers, i.e., hesperidin versus neohesperidin and naringin versus isonaringin. Methods After solid phase purification, components in sample were separated on a Agilent zorbax SB-C18 (5 μm, 250 mm × 4.6 mm) analytical column. ESI-MS and quasi-MSn were performed in negative ion mode to obtain structural data of these two pairs of flavanone 7-glycoside isomers. Moreover, UV absorption was measured. Results There was no intra-pairs difference in the UV-Vis and MS/MS spectra of the two pairs of 7-glycoside isomers, whereas the mass spectrometry fragmentation pathways between pairs were different. Conclusion The present study developed a LC-MS/MS method to explore the inter- and intra-pair difference of two pairs of flavanone 7-glycoside isomers.

Từ khóa


Tài liệu tham khảo

Tian YQ, Ding P: Study progress of Dachengqi decoction on the aspect of pharmacology, clinical research and related fields. Zhongyiyao Xuekan. 2006, 24: 2134-2135.

Qi QH, Wang K, Hui JF: Effect of Dachengqi granule on human gastrointestinal motility. Zhongguo Zhongxiyi Jiehe Zazhi. 2004, 24: 21-24.

Liu FC, Xue F, Cui ZY: Experimental and clinical research of Dachengqi decoction in treating post-traumatic respiratory distress syndrome. Zhongguo Zhongxiyi Jiehe Zazhi. 1992, 12: 541-542.

Zhao Q, Cui N, Li J: Clinical and experimental study of effect on acute phase protein level of multiple organ dysfunction syndrome treated with Dachengqi decoction. Zhongguo Zhongxiyi Jiehe Zazhi. 1998, 18: 453-456.

Wang SS, Qi QH: Influence of pre-operational medicated Dachengqi granule on inflammatory mediator in tumor patients. Zhongguo Zhongxiyi Jiehe Zazhi. 1999, 19: 337-339.

Tseng SH, Lee HH, Chen LG, Wu CH, Wang CC: Effects of three purgative decoctions on inflammatory mediators. J Ethnopharmacol. 2006, 105: 118-124.

Havsteen BH: Biochemistry and medical significance of the flavonoids. Pharmacol Ther. 2002, 96: 67-202.

Fukr U, Klittich K, Staib AH: Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. J Clin Pharmacol. 1993, 35: 431-436.

Guengerich FP, Kim DH: In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis. 1990, 11: 275-279.

Bors W, Heller W, Michel C, Saran M: Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Meth Enzymo. 1990, 186: 343-355.

Lambev I, Krushkov I, Zheliazkov D, Nikolov N: Antiexudative effect of naringin in experimental pulmonary edema and peritonitis. Eksperimentalna Meditsinai Morfologiia. 1980, 19: 207-212.

Tang BY, Adams NR: Effect of equol on oestrogen receptors and on synthesis of DNA and protein in the immature rat uterus. J Endocrinol. 1980, 85: 291-297.

Nishino H, Nagao M, Fujili H: Role of flavonoids in suppressing the enhancement of phospholipid metabolism by tumor promoters. Cancer Lett. 1983, 21: 1-8.

Xu F, Liu Y, Zhang Z, Song R, Tian Y: Simultaneous SPE-LC Determination of Three Flavonoid Glycosides of Naringin, Neohesperidin and Hesperidin in Da-Cheng-Qi Decoction. Chromatographia. 2007, 9/10: 763-766.

Tong RS, Sun SM, Wu QX: Determination of hesperidin in fructus aurantii immaturus by RP-HPLC. Huaxi Yaoxue Zazhi. 2000, 15: 454-455.

Lei H, Feng WH: Determination of Hesperidin in Zhizhu Capsule by HPLC. Zhongguo Shiyan Fangjixue Zazhi. 2005, 11: 5-6.

Yang WL, Yu SP, Yang SL, Ren YD, Li YF: Determination of neoheperidin in Fructus Aurantii by RP-HPLC. Shizhen Guoyi Guoyao. 2005, 16: 280-281.

Liang YY, Feng B, Zhu CC, Ni C: Determination of naringin and hesperidin in Fructus Aurantii Immaturus by HPLC. Zhongguo Xinyao Yu Lingchuang Yaoli. 2006, 17: 359-361.

Yang WL, Yang SL, Zhang M, Huang JL: Determination of naringin and neohesperidin in fructus aurantii by RP-HPLC. Zhongguo Xinyao Yu Lingchuang Yaoli. 2005, 16: 261-263.

Cuyckens F, Claeys M: Mass spectrometry in the structural analysis of flavonoids. J Mass Spectrom. 2004, 39: 1-15.

Fabre N, Rustan I, de Hoffmann E, Quetin-Leclercq J: Determination of Flavone, Flavonol, and Flavanone Aglycones by Negative Ion Liquid Chromatography Electrospray Ion Trap Mass Spectrometry. J Am Soc Mass Spectrom. 2001, 12: 707-715.

Stobiecki M: Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochemistry. 2000, 54: 237-256.

Zhou D, Xu Q, Xue X, Zhang F, Liang X: Identification of O-diglycosyl flavanones in Fructus aurantii by liquid chromatography with electrospray ionization and collision-induced dissociation mass spectrometry. J Pharm Biomed Anal. 2006, 42: 441-448.

Kevin PB, Steven JL, Dietrich AV: Characterization of isomeric sulfonamides using capillary zone electrophoresis coupled with nano-electrospray quasi-MS/MS/MS. J Mass Spectrom. 1997, 32: 297-304.

Dietrich AV, Bashir M, Steven JL: Study of 4-quinolone antibiotics in biological samples by short-column liquid chromatography couple with electrospray ionization tandem mass spectrometry. Anal Chem. 1997, 69: 4143-4155.

Joly N, El Aneed A, Martin P, Cecchelli R, Banoub J: Structural determination of the novel fragmentation routes of morphine opiate receptor antagonists using electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass Spectrom. 2005, 19: 3119-3130.

Thông tin
Thông tin xuất bản

Chinese Medicine

Tập 4 Số 1

Thông tin tác giả