Total synthesis and stereochemical determination of yoshinone A

Seiichi Shinomiya, Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga

Research output: Contribution to journalArticle

1 Citation (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 languageEnglish
Pages (from-to)109-114
Number of pages6
JournalPhytochemistry
Volume132
DOIs
Publication statusPublished - 2016 Dec 1

Fingerprint

Pyrones
3T3-L1 Cells
Polyketides
Cyanobacteria
Adipocytes
Leptolyngbya
Obesity
Lead compounds
pyrones
diastereomers
polyketides
synthesis
Cytotoxicity
adipocytes
Research
Pharmaceutical Preparations
cytotoxicity
obesity
drugs
cells

Keywords

  • Leptolyngbya sp.
  • Marine cyanobacteria
  • Polyketide
  • Total synthesis
  • Yoshinone A

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Total synthesis and stereochemical determination of yoshinone A. / Shinomiya, Seiichi; Iwasaki, Arihiro; Ohno, Osamu; Suenaga, Kiyotake.

In: Phytochemistry, Vol. 132, 01.12.2016, p. 109-114.

Research output: Contribution to journalArticle

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