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Short Paper | Regular issue | Vol 106, No. 2, 2023, pp.319-335
Published online, 21st December, 2022
DOI: 10.3987/COM-22-14759
Sialidase Inhibitory Activity of Synthesized Biflavonoid Glycoconjugates

Hiroaki Sasaki,* Takayuki Nagai, Takayuki Nakamura, Yusuke Umezawa, Kazuhiko Miki, Haruki Yamada, Kiyotaka Koyama, Kunio Takahashi, and Kaoru Kinoshita

*Department of Pharmacognosy and Phytochemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


Ginkgetin (1) and sciadopitysin (2) have been shown to exhibit influenza virus sialidase inhibitory activity. We report the synthesis and sialidase inhibitory activity of glycoconjugates consisting of biflavonoids (1, 2) and sugars: 2-keto-3-deoxy-D-glycero-D-galactonononic acid (KDN, 3), N-acetyl-D-glucosamine (GlcNAc, 4), and N-acetyl-D-lactosamine (LacNAc, 5). The glycoconjugates (18R, 18S, 21R, 21S) of biflavonoids (1, 2) and GlcNAc (4) showed selective inhibitory activity against sialidase of influenza A virus H1N1 subtype. In particular, the inhibitory activity of 18S was similar to or higher than that of 5,7,4'-trihydroxy-8-methoxyflavone (F36) as a positive control. The glycoconjugate 18S showed the most potent inhibitory activity against sialidase of influenza A virus H1N1 subtype, with an IC50 of 48.5 μg/mL.