ArticlePloS one2014
Stereoselective property of 20(S)-protopanaxadiol ocotillol type epimers affects its absorption and also the inhibition of P-glycoprotein.
Article in PloS one, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 36 citations in OpenAlex.
- Recent Advancements in Pentacyclic and Other Terpenoid Derivatives as Anti-inflammatory Agents.Mini reviews in medicinal chemistry · 2026Review
- Synthesis, Anti-Inflammatory Activities, and Molecular Docking Study of Novel Pyxinol Derivatives as Inhibitors of NF-κB Activation.Molecules (Basel, Switzerland) · 2024Article
- Methods on improvements of the poor oral bioavailability of ginsenosides: Pre-processing, structural modification, drug combination, and micro- or nano- delivery system.Journal of ginseng research · 2023Review
- Design, Synthesis, and Anti-Inflammatory Activities of 12-Dehydropyxinol Derivatives.Molecules (Basel, Switzerland) · 2023Article
- Synthesis and Anti-Hepatocarcinoma Effect of Amino Acid Derivatives of Pyxinol and Ocotillol.Molecules (Basel, Switzerland) · 2021Article
- Recent Advances in the Semisynthesis, Modifications and Biological Activities of Ocotillol-Type Triterpenoids.Molecules (Basel, Switzerland) · 2020Review
- Synthesis and Structure-Activity Relationship of Pyxinol Derivatives as Novel Anti-Inflammatory Agents.ACS medicinal chemistry letters · 2020Article
- Molecular Insight into Stereoselective ADME Characteristics of C20-24 Epimeric Epoxides of Protopanaxadiol by Docking Analysis.Biomolecules · 2020Article
- Discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins.Journal of ginseng research · 2017Review
- Characterization, Molecular Docking, and In Vitro Dissolution Studies of Solid Dispersions of 20(S)-Protopanaxadiol.Molecules (Basel, Switzerland) · 2017Article
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Authors and funding
5 authors at 1 institution in 1 country.
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Abstract
Stereoselectivity has been proved to be tightly related to drug action including pharmacodynamics and pharmacokinetics. (20S,24R)-epoxy-dammarane-3,12,25-triol (24R-epimer) and (20S,24S)-epoxy-dammarane-3,12,25-triol (24S-epimer), a pair of 20(S)-protopanaxadiol (PPD) ocotillol type epimers, were the main metabolites of PPD. Previous studies have shown that 24R-epimer and 24S-epimer had stereoselectivity in pharmacological action and pharmacokinetics. In the present study, the aim was to further study the pharmacokinetic characteristics of both epimers, investigate their absorption mechanism and analyze the selectivity effects of ocotillol type side chain and C24 stereo-configuration on P-glycoprotein (P-gp) in vivo and in vitro. Results showed that the absolute bioavailability of 24R-epimer was about 14-fold higher than that of 24S-epimer, and a linear kinetic characteristic was acquired in doses of 5-20 mg/kg for both epimers after oral administration. Furthermore, the apparent permeability coefficients of 24R-epimer were 5-7 folds higher than that of 24S-epimer having lower efflux ratios in Caco-2 cell models. Moreover, both 24R-epimer and 24S-epimer had similar inhibitory effects on P-gp by increasing cellular retention of rhodamine 123 in Caco-2 cells and decreasing efflux of digoxin across Caco-2 cell monolayers. In situ in vivo experiments showed that the inhibition of 24R-epimer on P-gp was stronger than that of 24S-epimer by single-pass intestinal perfusion of rhodamine 123 in rats. Western blot analyses demonstrated that both epimers had no action on P-gp expression in Caco-2 cells. In conclusion, with respect to the stereoselectivity, C24 S-configuration of the ocotillol type epimers processed a poor transmembrane permeability and could be distinguished by P-gp. Sharing a dammarane skeleton, both 24R-epimer and 24S-epimer were potent inhibitors of P-gp. This study provides a new case of stereoselective pharmacokinetics of chiral compounds which contributes to know the chiral characteristics of P-gp and structure-action relationship of PPD type and ocotillol type ginsenosides as a P-gp inhibitor.
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