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Rearranged Diels-Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra
Ist Teil von
Journal of natural products (Washington, D.C.), 2021-08, Vol.84 (8), p.2303-2311
Ort / Verlag
United States
Erscheinungsjahr
2021
Quelle
MEDLINE
Beschreibungen/Notizen
Two novel rearranged Diels-Alder adducts, morunigrines A (
) and B (
), and four new prenylated flavonoids, morunigrols A-D (
-
), were isolated from the twigs of
, together with four known prenylated phenolic compounds, including two flavonoids (
and
) and two 2-arylbenzofurans (
and
). Morunigrines A (
) and B (
) 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
was determined by the measurement of specific rotation. A plausible biogenetic pathway for
and
is also proposed. Compounds
and
exhibited more potent protein tyrosine phosphatase 1B inhibitory activity with IC
values of 1.8 ± 0.2 and 1.3 ± 0.3 μM, respectively, than that of the positive control oleanolic acid (IC
, 2.5 ± 0.1 μM).