Biotransformation and metabolic profile of American ginseng saponins with human intestinal microflora by liquid chromatography quadrupole time-of-flight mass spectrometry

Wan, Jianwei; Liu, Peng; Wang, Huaiyou; Qi, Lian‐Wen; Wang, Chong‐Zhi; Li, Ping; Yuan, Chun‐Su

doi:10.1016/j.chroma.2013.02.053

Cited by 122 publications

(128 citation statements)

References 34 publications

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“…According to the retention time, we inferred that the polarity of these metabolites are less than that of ADS-I. This result coincides with the previous studies, showing that triterpenoid saponins were converted to secondary glucosides or aglycones through deglycosylation and they have less polar properties in human intestinal bacteria biotransformation [13][14][15][16]. The metabolites of ADS-I were used for subsequent structural determination by UHPLC-MS, HPLC-NMR analysis.…”

Section: Hplc-elsd Analysissupporting

confidence: 73%

Ardipusilloside-I Metabolites from Human Intestinal Bacteria and Their Antitumor Activity

Cao

Wang

et al. 2015

Molecules

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Ardipusilloside-I (ADS-I) is a triterpenoid saponin extracted from Ardisia pusilla DC, and has been demonstrated to have potent antitumor activity. However, ADS-I metabolism in humans has not been investigated. In this study, we studied the biotransformation of ADS-I in human intestinal bacteria, and examined the in vitro antitumor activity of the major metabolites. Ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was used to detect ADS-I biotransformation products, and their chemical structures were identified by high performance liquid chromatography-nuclear magnetic resonance (HPLC-NMR). The antitumor activity of the major metabolites was determined by the MTT assay. Here, we show that main reaction seen in the metabolism of ADS-I in human intestinal bacteria was deglycosylation, which produced a total of four metabolites. The structures of the two major metabolites M1 and M2 were confirmed by using NMR. MTT assay showed that ADS-I metabolites M1 and M2 have the same levels of inhibitory activities as ADS-I in cultured SMMC-7721 cells and MCF-7 cells. In conclusion, this study demonstrates deglycosylation as a primary pathway of ADS-I metabolism in human intestinal bacteria, and suggests that the pharmacological activity of ADS-I may be mediated, at least in part, by its metabolites.

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Section: Hplc-elsd Analysissupporting

confidence: 73%

Ardipusilloside-I Metabolites from Human Intestinal Bacteria and Their Antitumor Activity

Cao

Wang

et al. 2015

Molecules

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“…For example, compound K, a major metabolite in the protopanaxadiols group, has a better bioactivity than its parent compound, ginsenoside Rb 1 [15]. In an in vitro study we observed that human enteric microbiota metabolized ginseng parent compounds into 25 metabolites [16]. However, to date, the determination of ginseng metabolites in human biological samples has largely not been carried out.…”

Section: Introductionmentioning

confidence: 99%

“…Based on our previous studies, liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (LC-Q-TOF-MS) can be effectively used to characterize ginseng saponins and their metabolites [16]. This technique provides advanced structural information with high sensitivity, specificity, and versatility in characterizing complex metabolite profiles in matrix-based samples.…”

Section: Introductionmentioning

confidence: 99%

Determination of American ginseng saponins and their metabolites in human plasma, urine and feces samples by liquid chromatography coupled with quadrupole time-of-flight mass spectrometry

Wan

Wang

Liu

et al. 2016

Journal of Chromatography B

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American ginseng is a commonly consumed herbal medicine in the United States and other countries. Ginseng saponins are considered to be its active constituents. We have previously demonstrated in an in vitro experiment that human enteric microbiota metabolize ginseng parent compounds into their metabolites. In this study, we analyzed American ginseng saponins and their metabolites in human plasma, urine and feces samples by liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (LC-Q-TOF-MS). Six healthy male volunteers ingested 1 g of American ginseng twice a day for 7 days. On day 7, biological samples were obtained and pretreated with solid phase extraction. The ginseng constituents and their metabolites were characterized, including 5 ginseng metabolites in plasma, 10 in urine, and 16 in feces. For the plasma, urine and feces samples, the levels of ginsenoside Rb1 (a major parent compound) were 8.6, 56.8 and 57.7 ng/mL, respectively, and the levels of compound K (a major metabolite) were 58.4 ng/mL, 109.8 ng/mL and 10.06 μg/mL, respectively. It suggested that compound K had a remarkably high level in all three samples. Moreover, in human feces, ginsenoside Rk1 and Rg5, Rk3 and Rh4, Rg6 and F4 were detected as the products of dehydration. Further studies are needed to evaluate the pharmacological activities of the identified ginseng metabolites.

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“…Among these factors, the presence of intestinal bacteria is believed to play an important role in the gastrointestinal metabolism (Selma et al, 2009). Additionally, it has been illustrated that glycosides such as saponins are often metabolized by gut bacteria to secondary saponins or other metabolites which are more easily absorbed and more effective (Yan et al, 2012;Wan et al, 2013;.…”

Section: Introductionmentioning

confidence: 98%

Screening of Intestinal Bacterial Metabolites of Platycodin D Using Ultra-Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry

Zhang

Qian

et al. 2016

Am. J. Chin. Med.

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Platycodin D (PD), a bioactive triterpenoid saponin isolated from Platycodi Radix (PR), possesses a vast range of biological activities. Although the pharmacological activities and pharmacokinetics of PD have been well demonstrated, information regarding the intestinal metabolisms of PD is very limited. In this study, human and rat fecal microflora were prepared and anaerobically incubated with PD at 37[Formula: see text]C for 48[Formula: see text]h, respectively. A highly sensitive and specific ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF/MS) was developed for the analysis of PD and related metabolites in the reaction samples. A Liquid-liquid extraction method was used for sample pretreatment and the chromatographic separation was performed on a 1.7 [Formula: see text]m particle size Syncronis C[Formula: see text] column using gradient elution system. Finally, a total of seven metabolites were detected and tentatively identified, such as the demethylation metabolite (M1), deoxidation metabolites (M3, M7) and hydrolysis at the C-28 oligosaccharide metabolites (M5, M6), which were first discovered in this experiment. The results indicate that hydrolysis, demethylation, dehydroxylation, and acetylation were the major metabolic pathways of PDin vitro. Additionally, four bacterial strains from human feces including Enterococcus sp.41, Bacillus sp.46, Escherichia sp.49 A and Escherichia sp.64 were detected and further identified with 16S rRNA gene sequencing due to their relatively strong metabolic capacity toward PD. The present study provides important information about the metabolism of PD, which will help elucidate the impact of intestinal bacteria on this active component.

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Biotransformation and metabolic profile of American ginseng saponins with human intestinal microflora by liquid chromatography quadrupole time-of-flight mass spectrometry

Cited by 122 publications

References 34 publications

Ardipusilloside-I Metabolites from Human Intestinal Bacteria and Their Antitumor Activity

Ardipusilloside-I Metabolites from Human Intestinal Bacteria and Their Antitumor Activity

Determination of American ginseng saponins and their metabolites in human plasma, urine and feces samples by liquid chromatography coupled with quadrupole time-of-flight mass spectrometry

Screening of Intestinal Bacterial Metabolites of Platycodin D Using Ultra-Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry

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