Dong Hongbo, Wu Min, Li Ying, Lu Lan, Qin Jialan, He Yujiao, Shi Zheng
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, School of Pharmacy & Clinical Medical College & Affiliated Hospital, Chengdu University, Chengdu 610106, China.
Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, China.
J Nat Prod. 2022 Apr 22;85(4):1118-1127. doi: 10.1021/acs.jnatprod.2c00021. Epub 2022 Mar 30.
The syntheses of three natural furanoflavonoid glucosides, including two flavone glucosides, pongamosides A () and B (), and a flavonol glucoside, pongamoside C (), 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 -glycosidic linkage. The anti-inflammatory activities of compounds -, as well as their aglycones , , and , were determined against NO production in the LPS-stimulated RAW264.7 cells. The results indicated that the -glycosylation may reduce the anti-inflammatory activity of furanoflavonoid .
首次以市售原料经9至15步反应实现了三种天然呋喃黄酮糖苷的合成，其中包括两种黄酮糖苷，即庞卡苷A（）和B（），以及一种黄酮醇糖苷，庞卡苷C（），总收率为2.9%至29%。合成路线的特点是通过NaH促进的BK-VK重排和酸催化的分子内环化反应来制备呋喃黄酮苷元。同时，采用相转移催化糖基化反应和施密特三氯乙酰亚胺酯法来构建关键的 -糖苷键。测定了化合物 -及其苷元 、 和 对脂多糖刺激的RAW264.7细胞中一氧化氮生成的抗炎活性。结果表明， -糖基化可能会降低呋喃黄酮的抗炎活性。
