Total synthesis and stereochemical determination of yoshinone A

Seiichi Shinomiya; Arihiro Iwasaki; Osamu Ohno; Kiyotake Suenaga

doi:10.1016/j.phytochem.2016.10.005

Total synthesis and stereochemical determination of yoshinone A

Seiichi Shinomiya, Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga

Department of Chemistry

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

6 Citations (Scopus)

Abstract

In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC₅₀ value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.

Original language	English
Pages (from-to)	109-114
Number of pages	6
Journal	Phytochemistry
Volume	132
DOIs	https://doi.org/10.1016/j.phytochem.2016.10.005
Publication status	Published - 2016 Dec 1

Keywords

Leptolyngbya sp.
Marine cyanobacteria
Polyketide
Total synthesis
Yoshinone A

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

UN SDGs

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

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10.1016/j.phytochem.2016.10.005

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title = "Total synthesis and stereochemical determination of yoshinone A",

abstract = "In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC50 value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.",

keywords = "Leptolyngbya sp., Marine cyanobacteria, Polyketide, Total synthesis, Yoshinone A",

author = "Seiichi Shinomiya and Arihiro Iwasaki and Osamu Ohno and Kiyotake Suenaga",

note = "Funding Information: This work was supported in part by Keio Gijuku Academic Development Funds . Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

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doi = "10.1016/j.phytochem.2016.10.005",

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journal = "Phytochemistry",

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T1 - Total synthesis and stereochemical determination of yoshinone A

AU - Shinomiya, Seiichi

AU - Iwasaki, Arihiro

AU - Ohno, Osamu

AU - Suenaga, Kiyotake

PY - 2016/12/1

Y1 - 2016/12/1

N2 - In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC50 value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.

AB - In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC50 value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.

KW - Leptolyngbya sp.

KW - Marine cyanobacteria

KW - Polyketide

KW - Total synthesis

KW - Yoshinone A

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DO - 10.1016/j.phytochem.2016.10.005

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AN - SCOPUS:84994654187

SN - 0031-9422

VL - 132

SP - 109

EP - 114

JO - Phytochemistry

JF - Phytochemistry

ER -

Total synthesis and stereochemical determination of yoshinone A

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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