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

Yuki Hitora; Kentaro Takada; Yuji Ise; Sau Pinn Woo; Seiya Inoue; Naoki Mori; Hirosato Takikawa; Shohei Nakamukai; Shigeru Okada; Shigeki Matsunaga

doi:10.1016/j.bmc.2019.115233

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. Epub 2019 Nov 30.

Authors

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Cell Cycle / drug effects
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
HeLa Cells
Humans
Molecular Structure
Porifera / chemistry*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

Antineoplastic Agents
Sesquiterpenes
metachromin T
metachromin C