Chiral high-performance liquid chromatographic separation of evodiamine enantiomers and rutaecarpine, isolated from Evodiae fructus

The impact of chirality on the analysis of alkaloids in plant

“…Furthermore, cavitation bubbles within the fluid formed more easily due to the decreased solvent viscosity, and thus the tensile strength of the liquid was reduced (Klein-Júnior et al 2016). Nevertheless, the disadvantage of too high temperature is the degradation and racemization of chiral alkaloids as reported for the extraction of evodiamine enantiomers from Evodiae fructus, in which S-(+)-evodiamine start to convert to its R-(−)-form at 40 °C partly (Nguyen et al 2013). For this reason, temperature should be optimized as it can be a factor playing a dual role in the extraction process.…”

“…Matrix interferences were removed by 30% isopropanol in water. Then, the alkaloids were eluted by acetonitrile (Nguyen et al 2013). In addition, the C 18 (Nguyen et al 2013) sorbents are usually applied to eliminate polar impurities from aqueous matrices which would exert a negative impact on chiral alkaloids analysis by normal-phase HPLC and CE.…”

Antiproliferative Effects of Alkaloid Evodiamine and Its Derivatives

“…In the same year, Nguyen’s group successfully isolated evodiamine enantiomers from 13 Evodia rutaecarpa samples by chiral high-performance liquid chromatographic method [ 171 ]. The results showed that S -(+)-evodiamine was present in higher concentration than R -(−)-evodiamine.…”

Therapeutic and cosmetic applications of Evodiamine and its derivatives—A patent review

“…Further experimental studies related to the isolation of these enantiomers reveal that the S (+) enantiomer is the major component while the R (−) is in the minor component in the E. fructus extract [10]. The molecular basis responsible for the therapeutic activity in terms of its enantiomers is not yet fully explored.…”