Production of novel bispyrone metabolites in the cellular slime mold Dictyostelium giganteum induced by zinc(II) ion

Van Hai Nguyen; Haruhisa Kikuchi; Hiraku Sasaki; Kyoichi Iizumi; Yuzuru Kubohara; Yoshiteru Oshima

doi:10.1016/j.tet.2016.12.040

Production of novel bispyrone metabolites in the cellular slime mold Dictyostelium giganteum induced by zinc(II) ion

Van Hai Nguyen, Haruhisa Kikuchi, Hiraku Sasaki, Kyoichi Iizumi, Yuzuru Kubohara, Yoshiteru Oshima

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

7 Citations (Scopus)

Abstract

In this study, Zn²⁺induced the production of two new bispyrone-type metabolites, dictyobispyrone B and E, in the cellular slime mold Dictyostelium giganteum. Their structures were proposed on the basis of spectroscopic analysis and confirmed by chemical synthesis. They possess a novel α,α-bispyrone skeleton modified with long carbon chains. Both could be formed from two different polyketide chains through a novel biosynthetic pathway. Our results indicate that cultivation of cellular slime molds in the presence of Zn²⁺is a useful technique for discovering other structurally unique compounds.

Original language	English
Pages (from-to)	583-588
Number of pages	6
Journal	Tetrahedron
Volume	73
Issue number	5
DOIs	https://doi.org/10.1016/j.tet.2016.12.040
Publication status	Published - 2017
Externally published	Yes

Keywords

Bispyrone
Cellular slime molds
Dictyostelium
Structural elucidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2016.12.040

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title = "Production of novel bispyrone metabolites in the cellular slime mold Dictyostelium giganteum induced by zinc(II) ion",

abstract = "In this study, Zn2+induced the production of two new bispyrone-type metabolites, dictyobispyrone B and E, in the cellular slime mold Dictyostelium giganteum. Their structures were proposed on the basis of spectroscopic analysis and confirmed by chemical synthesis. They possess a novel α,α-bispyrone skeleton modified with long carbon chains. Both could be formed from two different polyketide chains through a novel biosynthetic pathway. Our results indicate that cultivation of cellular slime molds in the presence of Zn2+is a useful technique for discovering other structurally unique compounds.",

keywords = "Bispyrone, Cellular slime molds, Dictyostelium, Structural elucidation",

author = "Nguyen, {Van Hai} and Haruhisa Kikuchi and Hiraku Sasaki and Kyoichi Iizumi and Yuzuru Kubohara and Yoshiteru Oshima",

note = "Funding Information: This work was supported in part by the Grants-in-Aid for Scientific Research (no. 16H03279) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan; the Platform Project for Supporting in Drug Discovery and Life Science Research from Japan Agency for Medical Research and Development (AMED); the Shorai Foundation for Science and Technology; Kobayashi International Scholarship Foundation; and the Takeda Science Foundation. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tet.2016.12.040",

language = "English",

volume = "73",

pages = "583--588",

journal = "Tetrahedron",

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T1 - Production of novel bispyrone metabolites in the cellular slime mold Dictyostelium giganteum induced by zinc(II) ion

AU - Nguyen, Van Hai

AU - Kikuchi, Haruhisa

AU - Sasaki, Hiraku

AU - Iizumi, Kyoichi

AU - Kubohara, Yuzuru

AU - Oshima, Yoshiteru

N1 - Funding Information: This work was supported in part by the Grants-in-Aid for Scientific Research (no. 16H03279) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan; the Platform Project for Supporting in Drug Discovery and Life Science Research from Japan Agency for Medical Research and Development (AMED); the Shorai Foundation for Science and Technology; Kobayashi International Scholarship Foundation; and the Takeda Science Foundation. Publisher Copyright: © 2016 Elsevier Ltd

PY - 2017

Y1 - 2017

N2 - In this study, Zn2+induced the production of two new bispyrone-type metabolites, dictyobispyrone B and E, in the cellular slime mold Dictyostelium giganteum. Their structures were proposed on the basis of spectroscopic analysis and confirmed by chemical synthesis. They possess a novel α,α-bispyrone skeleton modified with long carbon chains. Both could be formed from two different polyketide chains through a novel biosynthetic pathway. Our results indicate that cultivation of cellular slime molds in the presence of Zn2+is a useful technique for discovering other structurally unique compounds.

AB - In this study, Zn2+induced the production of two new bispyrone-type metabolites, dictyobispyrone B and E, in the cellular slime mold Dictyostelium giganteum. Their structures were proposed on the basis of spectroscopic analysis and confirmed by chemical synthesis. They possess a novel α,α-bispyrone skeleton modified with long carbon chains. Both could be formed from two different polyketide chains through a novel biosynthetic pathway. Our results indicate that cultivation of cellular slime molds in the presence of Zn2+is a useful technique for discovering other structurally unique compounds.

KW - Bispyrone

KW - Cellular slime molds

KW - Dictyostelium

KW - Structural elucidation

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JF - Tetrahedron

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Production of novel bispyrone metabolites in the cellular slime mold Dictyostelium giganteum induced by zinc(II) ion

Abstract

Keywords

ASJC Scopus subject areas

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