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Rearranged Diels–Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra
- Source :
- Journal of Natural Products. 84:2303-2311
- Publication Year :
- 2021
- Publisher :
- American Chemical Society (ACS), 2021.
-
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).
- Subjects :
- Pharmacology
biology
Chemistry
Stereochemistry
Organic Chemistry
Absolute configuration
Pharmaceutical Science
biology.organism_classification
Analytical Chemistry
Adduct
chemistry.chemical_compound
Complementary and alternative medicine
Prenylation
Drug Discovery
Molecular Medicine
Moiety
Specific rotation
IC50
Morus nigra
Oleanolic acid
Subjects
Details
- ISSN :
- 15206025 and 01633864
- Volume :
- 84
- Database :
- OpenAIRE
- Journal :
- Journal of Natural Products
- Accession number :
- edsair.doi...........85f199e723b08515f659c0fb2ddb124e