Metachromins X and Y from a marine sponge Spongia sp. and their effects on cell cycle progression

  • Bioorg Med Chem. 2020 Jan 15;28(2):115233. doi: 10.1016/j.bmc.2019.115233.
Yuki Hitora  1 ,  Kentaro Takada  2 ,  Yuji Ise  3 ,  Sau Pinn Woo  4 ,  Seiya Inoue  5 ,  Naoki Mori  5 ,  Hirosato Takikawa  5 ,  Shohei Nakamukai  1 ,  Shigeru Okada  1 ,  Shigeki Matsunaga  6
Affiliations
  • 1. Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
  • 2. Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan. Electronic address: [email protected].
  • 3. Sugashima Marine Biological Laboratory, Graduate School of Science, Nagoya University, Sugashima-cho, Toba-shi, Mie 517-0004, Japan.
  • 4. Center for Marine and Coastal Studies, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
  • 5. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bukyo-ku, Tokyo 113-8657, Japan.
  • 6. Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan. Electronic address: [email protected].
PMID: 31848114 DOI: 10.1016/j.bmc.2019.115233
Abstract

New sesquiterpene Quinones, metachromins X (1) and Y (2), together with the known metachromins C (3), J (4), and T (5), were isolated as inhibitors of cell cycle progression in the HeLa/Fucci2 cells. The structure of 1 was assigned by spectroscopic data and confirmed by a total synthesis. The planar structure of 2 was determined by interpretation of spectroscopic data, whereas its absolute configuration was analyzed by a combination of chiral HPLC and CD spectroscopy. Metachromins X (1) and C (3) arrested the cell cycle progression of HeLa/Fucci2 cells at S/G2/M phase.

Keywords
Cell-cycle; Marine sponge; Structure elucidation; Terpenoid.
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