Total Syntheses and Anti-inflammatory Evaluations of Pongamosides A-C, Natural Furanoflavonoid Glucosides from Fruit of Pongamia pinnata (L.) Pierre
Total Syntheses and Anti-inflammatory Evaluations of Pongamosides A-C, Natural Furanoflavonoid Glucosides from Fruit of Pongamia pinnata (L.) Pierre
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DOI：
10.1021/acs.jnatprod.2c00021
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发表时间：
2022-04-22
影响因子：
5.1
通讯作者：
Shi, Zheng
中科院分区：
文献类型：
--
作者：
Dong, Hongbo;Wu, Min;Shi, Zheng
以市售原料为原料，经9-15步反应，首次合成了3个天然呋喃黄酮苷，包括两个黄酮苷A(1)和B(2)和一个黄酮苷C(3)，总收率为2.9%~29%。该合成序列以NaH促进的BK-VK重排和酸催化的分子内环合反应为特征，合成了呋喃黄酮苷元。同时，通过相转移催化的糖基化反应和Schmidt的三氯乙酰亚氨酸酯反应建立了关键的O-糖苷键。测定化合物1-3及其苷元5a、5b和23对脂多糖刺激的RAW264.7细胞产生NO的抑制作用。结果表明，O-糖基化可降低呋喃黄酮类化合物的体外抗炎活性。
The syntheses of three natural furanoflavonoid glucosides, including two flavone glucosides, pongamosides A (1) and B (2), and a flavonol glucoside, pongamoside C (3), were achieved for the first time in 9-15 steps from commercially available materials in overall yields ranging from 2.9% to 29%. The synthetic sequence featured a NaH-promoted BK-VK rearrangement and acid-catalyzed intramolecular cyclization to furnish the furanoflavonoid aglycone. Meanwhile, phase-transfer-catalyzed glycosylation and Schmidt's trichloroacetimidate procedure were employed to establish the pivotal O-glycosidic linkage. The anti-inflammatory activities of compounds 1-3, as well as their aglycones 5a, 5b, and 23, were determined against NO production in the LPS-stimulated RAW264.7 cells. The results indicated that the O-glycosylation may reduce the anti-inflammatory activity of furanoflavonoid in vitro.