¹³ C NMR dereplication-assisted isolation of bioactive polyphenolic metabolites from Clusia flava Jacq.

Abstract

Presently it is estimated that many of the approximately 4000 new natural products isolated every year following complicated, long, and expensive isolation processes are already known; because of this, developing new strategies for locating secondary metabolites of interest in complex extracts or fractions is important. Currently, chromatographic and spectroscopic techniques are being used to optimize the isolation and identification of natural products. In this investigation we have used 13 C NMR dereplication analyses for the quick identification of a number of triterpenes (friedelin, lupeol, betulinic acid), sterols (euphol, sitosterol) and fatty acids (palmitic acid) present in semipurified fractions obtained from the stem bark extract of Clusia flava and to assist in the isolation of the bioactive metabolites trapezifolixanthone and paralycolin A. The complete and correct assignment of the 1 H and 13 C NMR spectroscopic data for paralycolin A is reported for the first time and the antioxidant and antiAGEs activity of both metabolites is described.

Vasorelaxant Activity of Salvia hispanica L.: Involvement of the Nitric Oxide Pathway in Its Pharmacological Mechanism

“…Meanwhile, phytochemical analyses were performed through the 13 C-NMR dereplication method as a spectroscopic strategy that has proven to help identify NPs in complex mixtures, even without purification [35]. This technique offers advantages over the dereplication analyses using mass spectrometry (MS), liquid chromatography (LC), gas chromatography (GC), or combined instrumentation such as LC-UV, LC-MS, or GC-MS [36]. Here, we have used 13 C-NMR chemical shift values obtained from crude extracts for the dereplication process to obtain a phytochemical approximation of S. hipanica seeds obtained in Jalisco, México.…”

The application and perspective of NMR and MS based strategies for functional compounds mining in medicinal and dietary plants

“…Other relevant literature has also reported the use of MixONat for elucidating the composition of propolis samples [51][52] , xanthones from Calophyllum brasiliense [53] , and polyphenolic FCs from Clusia flava Jacq. [54] . In conclusion, NMR-based dereplication approach was demonstrated to exhibit a powerful capability for exploring FCs from edible plant resources.…”