BK21 Project Team, College of Pharmacy, Chosun University, Dong-gu, Gwangju 501-759, Republic of Korea.
Bioorg Med Chem. 2011 Jun 1;19(11):3378-83. doi: 10.1016/j.bmc.2011.04.037. Epub 2011 Apr 22.
In the course of our program to search for protein tyrosine phosphatase 1B (PTPB) inhibitors, five new 5-deoxyflavonoids along with eight known derivatives were isolated from EtOAc layer of the root bark of Erythrina abyssinica. Their structures were elucidated on the basis of spectroscopic (IR, UV, MS, CD, 1D- and 2D-NMR) and physicochemical analyses. All isolates exhibited moderate inhibitory effects on the enzyme assay with IC₅₀ values ranging from 14.9 ± 1.6 to 98.1 ± 11.3 μM. Compounds with prenyl and methoxy groups in the B ring (1, 2, 4, 8, and 13) possessed strong activity (IC(50) 14.9 ± 1.6 to 19.2 ± 1.1 μM), while compounds (3, 5, and 9) with 2,2-dimethylpyrano ring showed less inhibitory effect (IC₅₀ 22.6 ± 2.3 to 72.9 ± 9.7 μM). These results suggest that prenyl and methoxy groups may be responsible for the increase on the activity of 5-deoxyflavonoids against PTP1B, but the presence of 2,2-dimethylpyrano ring on the B ring may be induced the decrease of PTP1B inhibitory activity.
在寻找蛋白酪氨酸磷酸酶 1B（PTPB）抑制剂的过程中，我们从非洲相思树的根皮的乙酸乙酯层中分离出了五种新的 5-脱氧黄酮类化合物和八种已知衍生物。根据光谱（IR、UV、MS、CD、1D 和 2D-NMR）和物理化学分析确定了它们的结构。所有分离物均表现出对酶测定的中等抑制作用，IC₅₀值范围为 14.9 ± 1.6 至 98.1 ± 11.3 μM。在 B 环中具有prenyl 和甲氧基的化合物（1、2、4、8 和 13）具有很强的活性（IC(50) 14.9 ± 1.6 至 19.2 ± 1.1 μM），而具有 2,2-二甲基吡喃环的化合物（3、5 和 9）则显示出较弱的抑制作用（IC₅₀ 22.6 ± 2.3 至 72.9 ± 9.7 μM）。这些结果表明，prenyl 和甲氧基可能是 5-脱氧黄酮类化合物对 PTP1B 活性增加的原因，但 B 环上存在 2,2-二甲基吡喃环可能会降低 PTP1B 的抑制活性。
