Comprehensive Evaluation of the Metabolism of Genipin-1-β-d-gentiobioside in Vitro and in Vivo by Using HPLC-Q-TOF

Abstract

To examine the metabolism of genipin-1-β-d-gentiobioside (GG), its distribution and biotransformation in vivo and in vitro were investigated. Urine, plasma, feces, and various organs were collected after oral administration of GG to normal rats and pseudo-germ-free rats to evaluate GG metabolism in vivo. GG was incubated with intestinal flora and primary hepatocytes in vitro to investigate microbial and hepatic metabolism. Using HPLC-Q-TOF-LC/MS, 11 metabolites of GG were absolutely or tentatively identified in terms possible elemental compositions, retention times, and characteristics of fragmentation patterns corresponding to eight biotransformations: deglycosylation, hydroxylation, sulfate conjugation, glucuronidation, hydrogenation, demethylation, glycosylation, and dehydration. Fewer metabolites were detected in pseudo-germ-free rats than in conventional rats. Moreover, geniposide and genipin were generated by the deglycoslation of intestinal bacteria. Geniposidic acid was detected in rat primary-hepatocyte incubation. This study first explores the metabolism of GG in vivo and in vitro. The results can aid the elucidation of PK profiles and clinical usage of gardenia fruit.

Evaluation of the chemical consistency of Yin‐Chen‐Hao‐Tang prepared by combined and separated decoction methods using high‐performance liquid chromatography and quadrupole time‐of‐flight mass spectrometry coupled with multivariate statistical analysis

“…As shown in Figure , all the observations were located within the Hotelling T2 (0.95) ellipse. Parameters R2X and Q2(cum) are usually used to evaluate the model fitness, with values close to 1.0 indicating good fitness for the model construction . For the PCA model, PC1 and PC2 respectively explained 24.3 and 8.9, 23.5 and 12% of the total variances in positive and negative ion mode.…”

“…Gallic acid (2), catechin (14), chlorogenic acid (17), esculetin (20), scopoline (21), genipingentiobioside (22), genipin (27), scopoletin (34), Emodin 1-O-β-D-glucopyranoside (38), emodin (40), emodin 8-O-β-D-glucoside (51), gradenoside (63), and rhein (69) were purchased from Chengdu Must Biotechnology (Chengdu, China). The purity was higher than 95% by HPLC-UV analysis.…”

Therapeutic effects of Cyathula officinalis Kuan and its active fraction on acute blood stasis rat model and identification constituents by HPLC-QTOF/MS/MS

“…The total ion chromatogram in negative ion mode, which provided more compounds information, was shown in Figure 3 . According to the extracted ion chromatogram and the ion fragments information as well as the corresponding standards or LC/MS data in the literature,[ 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 ] forty compounds were primarily identified [ Table 1 ] and their structures [ Figure 4 ] were speculated as follows, where the compounds are numbered according to their retention times in the total ion chromatogram. HPLC-QTOF/MS/MS analysis revealed that the major constituents of ACO were phytoecdysteroids and saponins.…”

A comparison of the chemical compounds in single- and co-boiled Zhi-Zi-Da-Huang decoctions with UPLC-qTOF-MS/MS and UPLC-DAD

“…Genipin could also in uence the induction of the in ammatory mediators inducible nitric oxide synthase (iNOS) and tumor necrosis factor (TNF)-α through the inhibition of nuclear transcription factor-κB (NF-κB) activation in hepatocytes; therefore, it might have therapeutic potential for liver injury [36]. Moreover, as one of the major pharmacodynamic substances, G1 generated geniposide and genipin via deglycosylation involving intestinal bacteria, and then distributed in the target organ for hepatinica and cholagogue [37]. As one of the primary constituents of crocin, Crocin-I could reduce oxidative damage in liver tissue in diabetic rats [38].…”