Trachelogenin

Fitoterapia. 2015 Jan;100:19-26.

Endogenous enzyme-hydrolyzed fruit of Cirsium brachycephalum: optimal source of the antiproliferative lignan trachelogenin regulating the Wnt/β-catenin signaling pathway in the SW480 colon adenocarcinoma cell line.[Pubmed: 25447161]

The molecular constituents of Cirsium brachycephalum fruits were identified, quantified and isolated for the first time.
METHODS AND RESULTS:
The lignan glycoside tracheloside was the main compound, which was transformed quantitatively into its aglycone Trachelogenin by endogenous enzymatic treatment of the fruit. Following this transformation by high performance liquid chromatography (HPLC) hyphenated with UV and mass spectrometry (MS) detections on a quantitative basis, the enzyme-hydrolyzed fruit was found to be the richest raw material containing Trachelogenin (17.2mg/g) reported to date. Thus, the enzyme-hydrolyzed fruit was used to isolate Trachelogenin using preparative HPLC in order to (1) unambiguously confirm its identity by gas chromatography-MS, nuclear magnetic resonance spectroscopy and optical rotation, and (2) investigate its in vitro antiproliferative activities against the SW480 colon adenocarcinoma cell line.
CONCLUSIONS:
Trachelogenin significantly affected the phosphorylation of key proteins such as β-Catenin, c-Myc and GSK3 in the β-Catenin signaling pathway in a concentration-dependent manner. These changes account for the antiproliferative effects of Trachelogenin.

J Chromatogr B Analyt Technol Biomed Life Sci. 2011 May 1;879(15-16):1033-7.

Simultaneous quantification of tracheloside and trachelogenin in rat plasma using liquid chromatography/tandem mass spectrometry.[Pubmed: 21482203]

We developed and validated a quantitative method for simultaneously determining the concentrations of tracheloside and Trachelogenin in rat plasma.
METHODS AND RESULTS:
Plasma samples were prepared by liquid-liquid extraction with ethyl acetate. Isocratic chromatographic separation was performed on a reversed-phase Diamonsil C(18) column (4.6×200 mm, 5 μm). The mobile phase consisted of methanol and 10mM aqueous ammonium formate (80:20, v/v). Analyte detection was achieved by positive electrospray ionization (ESI) tandem mass spectrometry. Calibration was performed by internal standardization with glipizide, and regression curves ranging from 0.625 to 625 ng/mL were constructed for both the analytes. The intra- and inter-day precision values were below 8%, and accuracy ranged from -5.33% to 2.53% in all quality control samples.
CONCLUSIONS:
In this study, the validated method was successfully applied to determine the pharmacokinetic profile of tracheloside and Trachelogenin in rat plasma after oral and intravenous administration of trachelospermi total lignans.