1. Bioactive monoterpene phenol dimers from the fruits of Psoralea corylifolia L.
- Author
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Gao HT, Lang GZ, Zang YD, Ma J, Yang JZ, Ye F, Tian JY, Gao PP, Li CJ, and Zhang DM
- Subjects
- Dose-Response Relationship, Drug, Enzyme Inhibitors chemistry, Enzyme Inhibitors isolation & purification, Humans, Molecular Docking Simulation, Molecular Structure, Monoterpenes chemistry, Monoterpenes isolation & purification, Phenols chemistry, Phenols isolation & purification, Protein Tyrosine Phosphatase, Non-Receptor Type 1 metabolism, Structure-Activity Relationship, Enzyme Inhibitors pharmacology, Fruit chemistry, Monoterpenes pharmacology, Phenols pharmacology, Protein Tyrosine Phosphatase, Non-Receptor Type 1 antagonists & inhibitors, Psoralea chemistry
- Abstract
Nine undescribed monoterpene phenol dimers, bisbakuchiols D-L (1-9), were isolated from the fruits of Psoralea corylifolia L. Their structures were elucidated based on extensive spectral analysis. The absolute configurations of 1-9 were specified by experimental and quantum chemical calculations of ECD spectra, and that of 1 was further established by X-ray diffraction analysis using Cu Kα radiation. Bisbakuchiols (1-4) were composed of two bakuchiols, one of which was cyclized via a C-7'/ C-12' single bond to form a six-member ring, and connect to each other by C-4-O-C-13' bonds. Bisbakuchiols (7-9) had a pyran ring by linkage of C-8-O-C-12. In the enzyme assay, compounds 5 and 9 exhibited significant PTP1B inhibitory activities with IC
50 values of 0.69 and 0.73 μM, and compounds 1 and 3 showed moderate PTP1B inhibitory activities. Furthermore, a molecular docking simulation of PTP1B and active compounds 5 and 9 showed that these active compounds possess low binding affinities ranging from -6.9 to -7.1 kcal/mol., (Copyright © 2021 Elsevier Inc. All rights reserved.)- Published
- 2021
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