Rearranged Diels-Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra
Rearranged Diels-Alder Adducts and Prenylated Flavonoids as Potential PTP1B Inhibitors from Morus nigra
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重排的狄尔斯-桤木加合物和异戊二烯化黄酮类化合物作为黑桑的潜在 PTP1B 抑制剂
DOI：
10.1021/acs.jnatprod.1c00403
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发表时间：
2021-07-19
影响因子：
5.1
通讯作者：
Mao, Shui-Chun
中科院分区：
文献类型：
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作者：
Qu, Ke-Jun;Wang, Bin;Mao, Shui-Chun
从黑桑枝条中分离得到两个新的重排Diels-Alder加合物Morungrines A(1)和B(2)，以及四个新的苯基化黄酮类化合物Morunigrols A-D(3-6)，以及四个已知的苯基化酚类化合物，包括两个黄酮类化合物(7和8)和两个2-芳基苯并呋喃类化合物(9和10)。Morungrines A(1)和B(2)是一类新型的Diels-Alder加合物，具有前所未有的碳骨架，其核心是重排的查尔酮-二苯乙烯/2-芳基苯并呋喃，并带有独特的甲基联苯部分。通过对波谱数据的分析，确定了新化合物的结构。通过比旋光度的测定确定了化合物6的绝对构型。还提出了1和2的可能的生物发生途径。化合物1和2具有较强的蛋白酪氨酸磷酸酶1B抑制活性，其IC50值分别为1.8+/-0.2和1.3+/-0.3mU，高于阳性对照齐墩果酸(IC50，2.5+/-0.1mU)。
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 mu M, respectively, than that of the positive control oleanolic acid (IC50, 2.5 +/- 0.1 mu M).