Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement

Scholarly Works

• Reyes-Hernández, O. D.; Figueroa-González, G.; Quintas-Granados, L. I.; Hernández-Parra, H.; Peña-Corona, S. I.; Cortés, H.; Kipchakbayeva, A.; Mukazhanova, Z.; Habtemariam, S.; Leyva-Gómez, G.; Büsselberg, D.; Sharifi-Rad, J. New insights into the anticancer therapeutic potential of icaritin and its synthetic derivatives. Drug development research 2024, 85, e22175. doi:10.1002/ddr.22175
• An, T.; Lin, G.; Liu, Y.; Qin, L.; Xu, Y.; Feng, X.; Li, C. De novo biosynthesis of anticarcinogenic icariin in engineered yeast. Metabolic engineering 2023, 80, 207–215. doi:10.1016/j.ymben.2023.10.003
• Gani, I.; Jameel, S.; Bhat, S. A.; Amin, H.; Bhat, K. A. Prenylated Flavonoids of Genus Epimedium: Phytochemistry, Estimation and Synthesis. ChemistrySelect 2023, 8. doi:10.1002/slct.202204263
• Gupta, M.; Mishra, A. Bioactive Flavonoids: A Comparative Overview of the Biogenetic and Chemical Synthesis Approach. Mini reviews in medicinal chemistry 2023, 23, 1818–1837. doi:10.2174/1389557523666230214101821
• Phang, Y. L.; Liu, S.; Zheng, C.; Xu, H. Recent advances in the synthesis of natural products containing the phloroglucinol motif. Natural product reports 2022, 39, 1766–1802. doi:10.1039/d1np00077b
• Zhang, J.; Xiong, W.; Wen, Y.; Fu, X.; Lu, X.; Zhang, G.; Wang, C. Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin. Organic & biomolecular chemistry 2022, 20, 1117–1124. doi:10.1039/d1ob02228h
• Kim, E.; Kim, Y.-M.; Ahn, J.; Chae, H.-S.; Chin, Y.-W.; Kim, J. Prenylated Flavonoid Glycosides with PCSK9 mRNA Expression Inhibitory Activity from the Aerial Parts of Epimedium koreanum. Molecules (Basel, Switzerland) 2021, 26, 3590. doi:10.3390/molecules26123590
• Khodzhaieva, R. S.; Gladkov, E. S.; Kyrychenko, A.; Roshal, A. D. Progress and Achievements in Glycosylation of Flavonoids. Frontiers in chemistry 2021, 9, 637994. doi:10.3389/fchem.2021.637994
• Wisanwattana, W.; Wongkrajang, K.; Cao, D.-Y.; Shi, X.; Zhang, Z.; Zhou, Z.; Li, F.; Mei, Q.; Wang, C.; Suksamrarn, A.; Zhang, G.; Wang, F. Inhibition of Phosphodiesterase 5 Promotes the Aromatase-Mediated Estrogen Biosynthesis in Osteoblastic Cells by Activation of cGMP/PKG/SHP2 Pathway. Frontiers in endocrinology 2021, 12, 636784. doi:10.3389/fendo.2021.636784
• Li, J. J. Claisen Rearrangement. Name Reactions; Springer International Publishing, 2021; pp 91–108. doi:10.1007/978-3-030-50865-4_30
• Yang, X.; Chen, J.; Huang, W.; Zhang, Y.; Yan, X.; Zhou, Z.; Wang, Y. Synthesis of icariin in tobacco leaf by overexpression of a glucosyltransferase gene from Epimedium sagittatum. Industrial Crops and Products 2020, 156, 112841. doi:10.1016/j.indcrop.2020.112841
• Feng, K.; Chen, R.; Xie, K.; Chen, D.; Liu, J.; Du, W.-Y.; Yang, L.; Dai, J. Ep7GT, a glycosyltransferase with sugar donor flexibility from Epimedium pseudowushanense, catalyzes the 7-O-glycosylation of baohuoside. Organic & biomolecular chemistry 2019, 17, 8106–8114. doi:10.1039/c9ob01352k
• Tong, J.; Liu, C.; Wang, B. Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin. Chemical Research in Chinese Universities 2019, 35, 616–620. doi:10.1007/s40242-019-9012-x
• Kim, B.; Lee, K. Y.; Park, B. Icariin abrogates osteoclast formation through the regulation of the RANKL-mediated TRAF6/NF-κB/ERK signaling pathway in Raw264.7 cells. Phytomedicine : international journal of phytotherapy and phytopharmacology 2018, 51, 181–190. doi:10.1016/j.phymed.2018.06.020
• Neves, A. R.; Correia-da-Silva, M.; Silva, P. M. A.; Ribeiro, D.; Sousa, E.; Bousbaa, H.; Pinto, M. Synthesis of New Glycosylated Flavonoids with Inhibitory Activity on Cell Growth. Molecules (Basel, Switzerland) 2018, 23, 1093. doi:10.3390/molecules23051093
• Pang, X.; Yin, S.; Yu, H.; Zhang, Y.; Wang, T.; Hu, L.-M.; Han, L. Prenylated flavonoids and dihydrophenanthrenes from the leaves of Epimedium brevicornu and their cytotoxicity against HepG2 cells. Natural product research 2017, 32, 2253–2259. doi:10.1080/14786419.2017.1405410
• Tao, Z.; Liu, J.; Jiang, Y.; Gong, L.; Yang, B. Synthesis of prenylated flavonols and their potents as estrogen receptor modulator. Scientific reports 2017, 7, 12445. doi:10.1038/s41598-017-12640-9
• Shen, X.; Zhou, Q.; Xiong, W.; Pu, W.; Zhang, W.; Zhang, G.; Wang, C. Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication. Tetrahedron 2017, 73, 4822–4829. doi:10.1016/j.tet.2017.06.064
• Almabruk, K. H.; Chang, J. H.; Mahmud, T. Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin. Journal of natural products 2016, 79, 2391–2396. doi:10.1021/acs.jnatprod.6b00621
• Shen, K.; Johnson, D. W.; Gobe, G. C. The role of cGMP and its signaling pathways in kidney disease. American journal of physiology. Renal physiology 2016, 311, F671–F681. doi:10.1152/ajprenal.00042.2016

Explore citations to this article at