Synthesis of 1-O-acyl- and 1-oxo-kamebanin analogues and their cytotoxic activity

  • Bioorg Med Chem Lett. 2023 Feb 15:82:129149. doi: 10.1016/j.bmcl.2023.129149.
Yutaka Aoyagi  1 ,  Kaori Tomita  2 ,  Asumi Kobayashi  2 ,  Akari Nakamura  2 ,  Yuki Fujii  2 ,  Momoka Yagi  2 ,  Yoshimi Ichimaru  2 ,  Kei Ozawa  3 ,  Hyun-Sun Park  3 ,  Haruhiko Fukaya  3 ,  Reiko Yano  2 ,  Tomoyo Hasuda  3 ,  Koichi Takeya  3 ,  Yukio Hitotsuyanagi  4 ,  Ming-Yu Gui  5 ,  Yong-Ri Jin  5 ,  Xu-Wen Li  5
Affiliations
  • 1. College of Pharmacy, Kinjo Gakuin University, 2-1723 Omori, Moriyama-ku, Nagoya, Aich 463-8521, Japan. Electronic address: [email protected].
  • 2. College of Pharmacy, Kinjo Gakuin University, 2-1723 Omori, Moriyama-ku, Nagoya, Aich 463-8521, Japan.
  • 3. 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
  • 4. 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan. Electronic address: [email protected].
  • 5. Department of Chemistry, JiLin University, No. 2 Xinmin street, Changchun, JiLin 130021, China.
PMID: 36690039 DOI: 10.1016/j.bmcl.2023.129149
Abstract

A series of 1-O-acyl- and 1-oxo-kamebanin analogues were prepared from kamebanin, isolated from Rabdosia excisa and their cytotoxicity was assayed on HL60 promyelocytic leukemia cells and HCT116 human colon Cancer cells. The structure-activity relationship study showed that the presence of 1-O-acyl groups of a C3-C5 carbon chain increased the cytotoxic activity.

Keywords
Cytotoxicity; Ent-kaurene; Kamebanin; Semi-synthesis; Structure–activity relationship.