Citation: Yan Shiqiang, Li Yingxia. Efficient Synthesis of 7, 4'-Dimethylapigenin-5-O-glycoside[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 561-565. doi: 10.6023/cjoc201807041 shu

Efficient Synthesis of 7, 4'-Dimethylapigenin-5-O-glycoside

Yan Shiqiang ,
Li Yingxia ^,

School of Pharmacy, Fudan University, Shanghai 201203

Corresponding author: Li Yingxia, liyx417@fudan.edu.cn
Received Date: 23 July 2018
Revised Date: 25 August 2018
Available Online: 10 February 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 81773576)the National Natural Science Foundation of China 81773576

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As the active component of precious Chinese medicine Aquilaria sinensis, 7, 4'-dimethylapigenin-5-O-glycoside showed inhibitory activity for nitric oxide (NO) production by activated RAW 264.7 cells. Because of the strong intramolecular H-bond, the 5-O-glucosidic linkage in flavonoids could not be efficiently constructed via conventional glycosylation method. In this paper, the efficient chemical synthesis of 7, 4'-dimethylapigenin-5-O-glycoside has been achieved for the first time starting from commercially available naringenin and D-glucose via a linear reaction sequence of 6 steps with the overall yield of 36.0%, wherein selective hydroxy protecting, reduction with sodium borohydride, glycosylation under phase transfer catalytic condition, oxidation with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) and other reactions were used. This work definitely laid the foundation for the further pharmacological study of this natural compound.
- Aquilaria sinensis,
- 7, 4'-dimethylapigenin-5-O-glycoside,
- flavonoids,
- chemical synthesis
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