Rearranged Diels–Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra
| Autor: | Bin Wang, Jia Li, Ke-Jun Qu, Song-Wei Li, Mao Shuichun, Chang-Sheng Jiang, Bao-Gang Xie, Yue-Wei Guo, Ai-Hong Liu |
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| Rok vydání: | 2021 |
| Předmět: |
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 |
| Zdroj: | Journal of Natural Products. 84:2303-2311 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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