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

Hitora Y 1 , Takada K 2 , Ise Y 3 , Woo SP 4 , Inoue S 5 , Mori N 5 Show all authors , Takikawa H 5 , Nakamukai S 1 , Okada S 1 , Matsunaga S 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: 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
Bioorg Med Chem, 2020 01 15;28(2):115233.
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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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