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

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

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Article number	115233
Journal	Bioorganic and Medicinal Chemistry
Volume	28
Issue number	2
DOIs	https://doi.org/10.1016/j.bmc.2019.115233
Publication status	Published - 2020 Jan 15
Externally published	Yes

Keywords

Cell-cycle
Marine sponge
Structure elucidation
Terpenoid

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2019.115233

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

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",

author = "Yuki Hitora and Kentaro Takada and Yuji Ise and Woo, {Sau Pinn} and Seiya Inoue and Naoki Mori and Hirosato Takikawa and Shohei Nakamukai and Shigeru Okada and Shigeki Matsunaga",

note = "Funding Information: The sponge was collected during the NT-09-17 cruise of Natsushima, JAMSTEC Japan Agency for Marine-Earth Science and Technology. This work was supported by JSPS KAKENHI 17H06403. We thank Dr. Shibata, BD Biosciences, for measuring FACS of HeLa/Fucci2 cells. Appendix A Funding Information: The sponge was collected during the NT-09-17 cruise of Natsushima, JAMSTEC Japan Agency for Marine-Earth Science and Technology. This work was supported by JSPS KAKENHI 17H06403. We thank Dr. Shibata, BD Biosciences, for measuring FACS of HeLa/Fucci2 cells.",

year = "2020",

month = jan,

day = "15",

doi = "10.1016/j.bmc.2019.115233",

language = "English",

volume = "28",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "2",

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TY - JOUR

T1 - Metachromins X and Y from a marine sponge Spongia sp. and their effects on cell cycle progression

AU - Hitora, Yuki

AU - Takada, Kentaro

AU - Ise, Yuji

AU - Woo, Sau Pinn

AU - Inoue, Seiya

AU - Mori, Naoki

AU - Takikawa, Hirosato

AU - Nakamukai, Shohei

AU - Okada, Shigeru

AU - Matsunaga, Shigeki

N1 - Funding Information: The sponge was collected during the NT-09-17 cruise of Natsushima, JAMSTEC Japan Agency for Marine-Earth Science and Technology. This work was supported by JSPS KAKENHI 17H06403. We thank Dr. Shibata, BD Biosciences, for measuring FACS of HeLa/Fucci2 cells. Appendix A Funding Information: The sponge was collected during the NT-09-17 cruise of Natsushima, JAMSTEC Japan Agency for Marine-Earth Science and Technology. This work was supported by JSPS KAKENHI 17H06403. We thank Dr. Shibata, BD Biosciences, for measuring FACS of HeLa/Fucci2 cells.

PY - 2020/1/15

Y1 - 2020/1/15

N2 - 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.

AB - 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.

KW - Cell-cycle

KW - Marine sponge

KW - Structure elucidation

KW - Terpenoid

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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