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

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

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: ktakada@kitasato-u.ac.jp.
  • 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: assmats@mail.ecc.-tokyo.ac.jp.
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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