Identification of major xanthones and steroidal saponins in rat urine by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry technology following oral administration of Rhizoma Anemarrhenae decoction

Abstract

Rhizoma Anemarrhenae (Zhimu in Chinese), the dried rhizome of Anemarrhena asphodeloides Bge. (Fam. Liliaceae), is a well-known traditional Chinese medicinal herb and has been used clinically in China for centuries to cure various diseases. However, like other traditional Chinese medicines, the effective constituents of this medicine, especially the assimilation and metabolites in vivo, which are very important to show their effects, have not been systematically studied. In this paper, solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization mass spectrometry technologies were used to study the constituents absorbed into rat urine and their metabolites after oral administration of Rhizoma Anemarrhenae decoction. A total of 11 compounds, including two xanthones, three of their metabolites and six steroidal saponins, were identified in rat urine sample. They were neomangiferin (1), glucuronide and monomethyl conjugate of mangiferin (2), mangiferin (3), monomethyl conjugate of mangiferin (4), dimethyl conjugate of mangiferin (5), timosaponin N or timosaponin E1 (6), timosaponin BII (7), timosaponin BIII (8), anemarrhenasaponin I or anemarrhenasaponin II (9), timosaponin AII (10) and timosaponin AIII (11). The results would efficaciously narrow the potentially active compounds range in Rhizoma Anemarrhenae decoction, and pave a helpful way for follow-up mechanism of action research.

Quantification and Purification of Mangiferin from Chinese Mango (Mangifera indica L.) Cultivars and Its Protective Effect on Human Umbilical Vein Endothelial Cells under H2O2-induced Stress

“…Further identification of the purified mangiferin was confirmed by HPLC-ESI-MS (Figure 4D), where the [M-H] − ion at m / z 421.0 indicating the molecular weight of mangiferin to be 422. Additionally, three C-glycoside xanthone typical product ions at m / z 403.0 [M-H 2 O] − , 331.0 [M-C 3 H 6 O 3 ] − , 301.0 [M-C 4 H 8 O 4 ] − were detected in LC-MS 2 chromatogram, the fragmentation pattern of which is consistent with the proposed mechanistic pathway by Ma et al [19]. Based on these data, the structure of the purified compound could be identified as mangiferin (C 19 H 18 O 11 ).…”

Simultaneous determination of active xanthone glycosides, timosaponins and alkaloids in rat plasma after oral administration of Zi-Shen Pill extract for the pharmacokinetic study by liquid chromatography–tandem mass spectrometry

“…Although identification of these constituents in rat serum and urine by liquid chromatography-mass spectrometry can be retrieved in the literature [13,14], to our knowledge, several analytical methods have been previously described to determine only one or two of these relevant compounds in plasma separately [15][16][17][18] and none of these methods is able to simultaneously determine all compounds of interest in biological samples. The present study was designed to develop a rapid and sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) with polarity switching and utilize it for full pharmacokinetic investigation of the main active constituents in ZSP following oral administration of its extract.…”

The Pharmacokinetics and Metabolism of Neomangiferin, a Major Bioactive Component in Anemarrhena asphodeloides

“…Neomangiferin and mangiferin co-exist, and they are considered the major active constituents in Zhimu [6]. Mangiferin has been investigated extensively because of its remarkable pharmacological effects, including antioxidant [7,8], anti-inflammatory [9], antidiabetic [10], anticancer [11], antibacterial [12], anti-HIV [13], and radioprotective activities [14].…”

“…metabolism of neomangiferin as another major bioactive substance and structurally similar to mangiferin. Ma et al [6] bioanalyzed neomangiferin after Rhizoma Anemarrhenae decoction is orally administered. Qiu et al [20] developed an ultra-performance liquid chromatography (UPLC)-tandem mass spectrometry (MS/MS) method to simultaneously determine mangiferin and neomangiferin in rat plasma after co-administration of mangiferin and neomangiferin.…”