Rearranged Diels-Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra.
J Nat Prod
; 84(8): 2303-2311, 2021 08 27.
Article
in En
| MEDLINE
| ID: mdl-34279099
ABSTRACT
Two novel rearranged Diels-Alder adducts, morunigrines A (1) and B (2), and four new prenylated flavonoids, morunigrols A-D (3-6), were isolated from the twigs of Morus nigra, together with four known prenylated phenolic compounds, including two flavonoids (7 and 8) and two 2-arylbenzofurans (9 and 10). Morunigrines A (1) and B (2) are a novel class of Diels-Alder adducts with unprecedented carbon skeletons featuring a rearranged chalcone-stilbene/2-arylbenzofuran core decorated with a unique methylbiphenyl moiety. The structures of the new compounds were assigned by analysis of spectroscopic data. The absolute configuration of compound 6 was determined by the measurement of specific rotation. A plausible biogenetic pathway for 1 and 2 is also proposed. Compounds 1 and 2 exhibited more potent protein tyrosine phosphatase 1B inhibitory activity with IC50 values of 1.8 ± 0.2 and 1.3 ± 0.3 µM, respectively, than that of the positive control oleanolic acid (IC50, 2.5 ± 0.1 µM).
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Flavonoids
/
Morus
/
Enzyme Inhibitors
/
Protein Tyrosine Phosphatase, Non-Receptor Type 1
Country/Region as subject:
Asia
Language:
En
Journal:
J Nat Prod
Year:
2021
Document type:
Article