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

Phytochemistry. 2016 Dec:132:109-114. doi: 10.1016/j.phytochem.2016.10.005. Epub 2016 Oct 17.

Authors

Seiichi Shinomiya¹, Arihiro Iwasaki¹, Osamu Ohno², Kiyotake Suenaga³

Affiliations

¹ Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
² Department of Chemistry and Life Science, Kogakuin University, 2665-1, Nakano-Machi, Hachioji, Tokyo 192-0015, Japan.
³ Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan. Electronic address: suenaga@chem.keio.ac.jp.

PMID: 27765324
DOI: 10.1016/j.phytochem.2016.10.005

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.

MeSH terms

3T3 Cells
Adipocytes / drug effects
Animals
Cell Differentiation
Cyanobacteria / chemistry*
Marine Biology
Mice
Polyketides / chemistry
Polyketides / isolation & purification*
Polyketides / pharmacology
Pyrones / chemical synthesis
Pyrones / chemistry
Pyrones / isolation & purification*
Pyrones / pharmacology
Stereoisomerism

Substances

Polyketides
Pyrones
yoshinone A