Liquid chromatography/mass spectrometry-based structural analysis of new platycoside metabolites transformed by human intestinal bacteria

Ha, Young Wan; Na, Yun-Cheol; Ha, In-Joong; Kim, Dong-Hyun; Kim, Yeong Shik

doi:10.1016/j.jpba.2009.08.002

Cited by 35 publications

(22 citation statements)

References 34 publications

(44 reference statements)

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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: 87%

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: 87%

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

Cao

Wang

et al. 2015

Molecules

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“…Thus, UPLC was applied to investigate the metabolic profiles of Flos A. manihot extract by normal and CKD model rat intestinal bacteria. Generally, flavonoid glycosides can be deglycosylated by enzymes of the gut microbiota, and then flavonoid aglycons are further metabolized through demethylation, dehydroxylation, hydrolytic, ring‐cleavage and some other reactions (Aura, ; Ha, Na, Ha, Kim, & Kim, ; Karabin, Hudcova, Jelinek, & Dostalek, ; Serra et al, ). In this study, with the optimized method, eight parent components – myricetin‐3‐ O ‐glucoside (M1), rutin (M2), hyperoside (M3), isoquercitrin (M4), hibifolin (M5), myricetin (M6), quercetin‐3′‐ O ‐glucoside (M7), quercetin (M8) – and their metabolites were detected after being compared with blank samples, which just contained Flos A. manihot extract (Table ).…”

Section: Resultsmentioning

confidence: 99%

Metabolic profiles of the Flos Abelmoschus manihot extract by intestinal bacteria from the normal and CKD model rats based on UPLC‐Q‐TOF/MS

Jiang

et al. 2016

Biomedical Chromatography

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Flos Abelmoschus manihot is a traditional herbal medicine widely used in clinical practice to tackle chronic kidney disease (CKD) for thousands of years. Nowadays, many studies indicate that gut bacteria are closely related to the progression of CKD and CKD-related complications. In this study, a UPLC-Q-TOF/MS method coupled with the MetaboLynx™ software was established and successfully applied to investigate the metabolites and metabolic profile of Flos A. manihot extract by intestinal bacteria from normal and CKD rats. Eight parent components and eight metabolites were characterized by their protonated ions. Among these compounds, 15 were detected in the two group samples while M16 was only determined in the CKD model samples. Compared with the quercetin-type glycosides, fewer myricetin-type and gossypetin-type metabolites were obtained in the two group samples. These metabolites suggested that deglycosylation and methylation are the major metabolic pathways of Flos A. manihot extract. Few differences of metabolite classes were observed in the two group samples. However, the concentrations of aglycones such as quercetin, myricetin and gossypetin in the normal samples were notably higher than those in the CKD model samples. The results are important in unravelling the pharmacological effects of A. manihot and clarifying its mechanism of action in vivo.

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“…In most cases, the bioavailability of saponins is low when taken orally because of their poor oral absorption and gastrointestinal metabolism (Han et al, 2006;Liang et al, 2007). Some of saponins are 15 transformed to their deglycosylated compounds by intestinal bacteria before being absorbed into blood in the normal gastrointestinal environment (Takeda et al, 1996;Ha et al, 2010;Komoto et al, 2010;Wang et al, 2012). During the process of evaluating histopathology in this study, a slight injury of gastrointestinal tract was observed in the high-dose male rats with hemolytic anemia.…”

Section: Discussionmentioning

confidence: 99%

Safety assessment of saponins extract in Dolichos falcatus Klein: Subchronic study in Sprague-Dawley rats

Lan

Huang

et al. 2015

Journal of Ethnopharmacology

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Liquid chromatography/mass spectrometry-based structural analysis of new platycoside metabolites transformed by human intestinal bacteria

Cited by 35 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

Metabolic profiles of the Flos Abelmoschus manihot extract by intestinal bacteria from the normal and CKD model rats based on UPLC‐Q‐TOF/MS

Safety assessment of saponins extract in Dolichos falcatus Klein: Subchronic study in Sprague-Dawley rats

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