2. Academic Validation
  3. Synthesis and cytotoxic activities of 8- and 6-demethyleucalyptins

Synthesis and cytotoxic activities of 8- and 6-demethyleucalyptins

  • Biosci Biotechnol Biochem. 2022 Aug 24;86(9):1200-1206. doi: 10.1093/bbb/zbac105.
Ryuki Asakawa 1,  Kanta Fuchiyama 1,  Yunosuke Ishii 1,  Keisuke Hosaka 1,  Atsushi Kobayashi 2,  Kei Shimazaki 1,  Junki Nagasawa 3,  Sayaka Tsuchida 4,  Kazunari Ushida 4,  Makoto Matsubayashi 3 5,  Yuuki Furuyama 1,  Kenji Ohgane 1 6,  Kouji Kuramochi 1
Affiliations

Affiliations

  • 1 Department of Applied Biological Science, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, Japan.
  • 2 Shin-etsu Nature Conservation Office, Environmental Ministry Japan, 1108 Asahi-cho, Nagano, Japan.
  • 3 Department of Veterinary Immunology, Graduate School of Veterinary Sciences, Osaka Metropolitan University, 1-58 Rinku-oraikita, Izumisano, Osaka, Japan.
  • 4 College of Bioscience and Biotechnology, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi, Japan.
  • 5 Department of Veterinary Parasitology, Faculty of Veterinary Medicine, Airlangga University, Mulyorejo, Surabaya, 60115, Indonesia.
  • 6 Department of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo, Japan.
PMID: 35776954 DOI: 10.1093/bbb/zbac105
Abstract

Secondary metabolites in Plants influence the health of herbivores such as Japanese ROCK ptarmigans that feed on the leaves and fruits of alpine Plants. Thus, it is important to understand the secondary metabolites of alpine Plants and their biological activities for conserving Japanese ROCK ptarmigans. We isolated C-methylflavone from the leaves of Kalmia procumbens, on which Japanese ROCK ptarmigans feed. Although its structure was deduced to be 8-demethyleucalyptin by comparing its nuclear magnetic resonance (NMR) data with the reported ones, the possibility that the isolated compound is 6-demethyleucalyptin cannot be ruled out. Thus, both isomers were synthesized. The isolated compound was unambiguously determined to be 8-demethyleucalyptin by comparing its NMR data with those of the synthetic ones. Cytotoxic evaluation of 8- and 6-demethyleucalyptins revealed that only the former showed cytotoxicity against HCT116 and MRC-5 cells. The present study provides not only easy access to 8- and 6-demethyleucalyptins, but also their biological information.

Keywords

C-methylflavone; 6-demethyleucalyptin; 8-demethyleucalyptin.

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