Sameuramide A, a new cyclic depsipeptide isolated from an ascidian of the family Didemnidae

Koshi MacHida, Daisuke Arai, Ryosuke Katsumata, Satoshi Otsuka, Jun K. Yamashita, Tao Ye, Shoubin Tang, Nobuhiro Fusetani, Youichi Nakao

Research output: Contribution to journalArticle

Abstract

Sameuramide A (1), a new cyclic depsipeptide encompassing one each of alanine, N-methyl alanine, N-methyl dehydroalanine, N,O-dimethyl threonine, phenyllactic acid, three β-hydroxy leucines, and two propionates, was isolated from a didemnid ascidian collected at the northern part of Japan. The planar structure was established based on the interpretation of MS and NMR data. The absolute configuration of the subunits was determined by the advanced Marfey's method and the chiral LC-MS analysis. Compound 1 exhibited the activity of maintaining colony formation of murine embryonic stem (mES) cells without leukemia inhibitory factor (LIF). Down regulation of the gene expression of Krüppel-like transcription factor 4 (Klf4) indicated that 1 itself was not able to maintain the undifferentiated state of the mES cells. However, the expression levels of the marker genes (Nestin, T, Sox17) for three germ layers were upregulated in embryoid bodies (EBs) after treatment of 1 together with LIF, suggesting that 1 plays a supportive role for LIF in maintaining the multipotency of mES cells.

Original languageEnglish
Pages (from-to)3852-3857
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume26
Issue number13
DOIs
Publication statusPublished - 2018 Jul 30

Fingerprint

Depsipeptides
Leukemia Inhibitory Factor
Urochordata
Embryonic Stem Cells
Stem cells
Alanine
Embryoid Bodies
Germ Layers
Nestin
Hydroxy Acids
Propionates
Gene Expression Regulation
Threonine
Gene expression
Leucine
Japan
Transcription Factors
Down-Regulation
Genes
Nuclear magnetic resonance

Keywords

  • Colony formation
  • Didemnid ascidian
  • Embryonic stem cells
  • Marine natural products
  • Peptide

ASJC Scopus subject areas

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

Cite this

Sameuramide A, a new cyclic depsipeptide isolated from an ascidian of the family Didemnidae. / MacHida, Koshi; Arai, Daisuke; Katsumata, Ryosuke; Otsuka, Satoshi; Yamashita, Jun K.; Ye, Tao; Tang, Shoubin; Fusetani, Nobuhiro; Nakao, Youichi.

In: Bioorganic and Medicinal Chemistry, Vol. 26, No. 13, 30.07.2018, p. 3852-3857.

Research output: Contribution to journalArticle

MacHida, K, Arai, D, Katsumata, R, Otsuka, S, Yamashita, JK, Ye, T, Tang, S, Fusetani, N & Nakao, Y 2018, 'Sameuramide A, a new cyclic depsipeptide isolated from an ascidian of the family Didemnidae', Bioorganic and Medicinal Chemistry, vol. 26, no. 13, pp. 3852-3857. https://doi.org/10.1016/j.bmc.2018.06.042
MacHida, Koshi ; Arai, Daisuke ; Katsumata, Ryosuke ; Otsuka, Satoshi ; Yamashita, Jun K. ; Ye, Tao ; Tang, Shoubin ; Fusetani, Nobuhiro ; Nakao, Youichi. / Sameuramide A, a new cyclic depsipeptide isolated from an ascidian of the family Didemnidae. In: Bioorganic and Medicinal Chemistry. 2018 ; Vol. 26, No. 13. pp. 3852-3857.
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