Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.