Molecules, Год журнала: 2023, Номер 28(21), С. 7313 - 7313

Опубликована: Окт. 29, 2023

Ginsenoside Rg5, a relatively uncommon secondary ginsenoside, exhibits notable pharmacological activity and is commonly hypothesized to originate from the dehydration of Rg3. In this work, we compared different conversion pathways using Rb1, R-Rg3 S-Rg3 as raw material under simple acid catalysis. Interestingly, results indicate that follows reaction order Rb1 > R-Rg3, which contrary common understanding Rg5 obtained Rg3 by dehydration. Our experimental have been fully confirmed theoretical calculations NOESY analysis. The DFT analysis reveals free energies in generating carbocation are 7.56 mol/L 7.57 mol/L, respectively, significantly higher than energy 1.81 when generates same carbocation. This finding aligns with evidence suggesting more prone findings nuclear magnetic resonance (NMR) suggest fatty chains (C22-C27) adopt Gauche conformation an anti C16-C17 C13-C17, due weak repulsive van der Waals force. Therefore, configuration conducive formation intramolecular hydrogen bonds between 20C-OH 12C-OH, whereas lacks capability. Consequently, also explains fact generate R-Rg3. Additionally, our research synthetic route derived protopanaxadiol (PPD)-type ginsenosides (including Rb2, Rb3, Rc Rd) advantages terms efficacy, purity yield pathway originating Moreover, study presents highly effective practical approach for extensive synthesis thereby facilitating exploration its properties potential application drug discovery.

Язык: Английский