Unusual ent-Kaurane Diterpenes from the Coffea Cultivar S288 Coffee Beans and Molecular Docking to α-Glucosidase.
J Agric Food Chem
; 70(2): 615-625, 2022 Jan 19.
Article
em En
| MEDLINE
| ID: mdl-35005957
ABSTRACT
A total of 11 new (1-11) and 2 known (12 and 13) ent-kaurane diterpene derivatives were identified from the roasted beans of Coffea cultivar S288. Their structures were established by extensive spectroscopic analysis, including one- and two-dimensional nuclear magnetic resonance (heteronuclear single-quantum correlation, heteronuclear multiple-bond correlation, correlation spectroscopy, and rotating-frame Overhauser enhancement spectroscopy), high-resolution electrospray ionization mass spectrometry, and X-ray analyses. Cafespirone acid A (1) represents the first example of diterpene featuring a spirocyclic skeleton constructed from a 6/6/5 tricyclic system. Cafeane acid A (2) possesses a 6/6/6/5 tetracyclic system as a result of the C/D ring rearrangement. Furthermore, compounds 1-12 were evaluated for their α-glucosidase inhibitory activity. The results showed that compounds 2, 4, 5, 6, 7, 10, and 11 had a moderate inhibitory effect on α-glucosidase, and half-maximal inhibitory concentration values of compounds 4, 6, 7, and 10 were 18.76 ± 1.46, 4.88 ± 0.03, 12.35 ± 0.91, and 12.64 ± 0.59 µM, respectively, compared to the positive control acarbose (60.71 ± 16.45 µM). Additionally, the molecular docking experiments showed that the carbonyl group at C-19 of compounds 4, 6, and 7 formed strong hydrogen bonds with ARG315, which may make them have moderate inhibitory activity.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Coffea
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Diterpenos do Tipo Caurano
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Diterpenos
Idioma:
En
Revista:
J Agric Food Chem
Ano de publicação:
2022
Tipo de documento:
Article