TY - JOUR
T1 - Sameuramide A, a new cyclic depsipeptide isolated from an ascidian of the family Didemnidae
AU - Machida, Koshi
AU - Arai, Daisuke
AU - Katsumata, Ryosuke
AU - Otsuka, Satoshi
AU - Yamashita, Jun K.
AU - Ye, Tao
AU - Tang, Shoubin
AU - Fusetani, Nobuhiro
AU - Nakao, Yoichi
N1 - Funding Information:
We would like to thank Prof. Teruaki Nishikawa of Toho University for the identification of the ascidian. We are also indebted to the Materials Characterization Central Laboratory of Waseda University for An Open-Ended Laboratory Program for Fourth-Year Undergraduate and Graduate Students.16 This work was financially supported in part by a Waseda University grant-in-Aid for Scientific Research, the Strategic Research Platforms for Private University, a Matching Fund Subsidy from the Ministry of Education, Science, Sports, and Technology (MEXT), Japan, and JSPS KAKENHI grant Numbers 26221204, 25560408, and 19310138; Shenzhen Peacock Plan (KQTD 2015071714043444). This work was supported by JSPS Core-to-Core Program, A. Advanced Research Networks. Also, this work was inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, Asian Chemical Biology Initiative (ACBI) and JSPS A3 Foresight Program.
Funding Information:
We would like to thank Prof. Teruaki Nishikawa of Toho University for the identification of the ascidian. We are also indebted to the Materials Characterization Central Laboratory of Waseda University for An Open-Ended Laboratory Program for Fourth-Year Undergraduate and Graduate Students. 16 This work was financially supported in part by a Waseda University grant-in-Aid for Scientific Research, the Strategic Research Platforms for Private University , a Matching Fund Subsidy from the Ministry of Education, Science, Sports, and Technology ( MEXT ), Japan, and JSPS KAKENHI grant Numbers 26221204 , 25560408 , and 19310138 ; Shenzhen Peacock Plan (KQTD 2015071714043444). This work was supported by JSPS Core-to-Core Program, A. Advanced Research Networks. Also, this work was inspired by the international and interdisciplinary environments of the JSPS Asian CORE Program, Asian Chemical Biology Initiative (ACBI) and JSPS A3 Foresight Program.
Publisher Copyright:
© 2018
PY - 2018/7/30
Y1 - 2018/7/30
N2 - 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.
AB - 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.
KW - Colony formation
KW - Didemnid ascidian
KW - Embryonic stem cells
KW - Marine natural products
KW - Peptide
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U2 - 10.1016/j.bmc.2018.06.042
DO - 10.1016/j.bmc.2018.06.042
M3 - Article
C2 - 29983284
AN - SCOPUS:85049325781
SN - 0968-0896
VL - 26
SP - 3852
EP - 3857
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 13
ER -