Bioactive monoterpene phenol dimers from the fruits of Psoralea corylifolia L.
Bioorg Chem
; 112: 104924, 2021 07.
Article
em En
| MEDLINE
| ID: mdl-33933806
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 IC50 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.
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Texto completo:
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Base de dados:
MEDLINE
Assunto principal:
Fenóis
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Psoralea
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Monoterpenos
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Inibidores Enzimáticos
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Proteína Tirosina Fosfatase não Receptora Tipo 1
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Frutas
Limite:
Humans
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article