Kakeromamide A, a new cyclic pentapeptide inducing astrocyte differentiation isolated from the marine cyanobacterium Moorea bouillonii

Fumiaki Nakamura; Hiroshi Maejima; Midori Kawamura; Daisuke Arai; Tatsufumi Okino; Meng Zhao; Tao Ye; Jungyeol Lee; Young-Tae Chang; Nobuhiro Fusetani; Yoichi Nakao

doi:10.1016/j.bmcl.2018.04.067

Kakeromamide A, a new cyclic pentapeptide inducing astrocyte differentiation isolated from the marine cyanobacterium Moorea bouillonii

Bioorg Med Chem Lett. 2018 Jul 1;28(12):2206-2209. doi: 10.1016/j.bmcl.2018.04.067. Epub 2018 Apr 30.

Authors

Affiliations

¹ Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
² Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
³ Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan.
⁴ State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055, China.
⁵ Department of Chemistry, POSTECH, Pohang 37673, Republic of Korea.
⁶ Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan; Fisheries and Oceans Hakodate, 3-1-1 Minato-cho, Hakodate 041-8611, Japan.
⁷ Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan; Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan. Electronic address: ayocha@waseda.jp.

PMID: 29773503
DOI: 10.1016/j.bmcl.2018.04.067

Abstract

Kakeromamide A (1), a new cyclic pentapeptide encompassing a thiazole ring moiety and a β-amino acid, was isolated from the marine cyanobacterium Moorea bouillonii. Its structure was elucidated by the spectral analysis and the modified Marfey's method. Compound 1 induced differentiation of neural stem cells into astrocytes at the concentration of 10 µM.

Keywords: Astrocyte differentiation; Cyanobacterium; Marine natural products; Neural stem cells; Pentapeptide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Astrocytes / drug effects*
Cell Differentiation / drug effects
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Cyanobacteria / chemistry*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Mice
Molecular Conformation
Oligopeptides / chemistry
Oligopeptides / isolation & purification
Oligopeptides / pharmacology*
Structure-Activity Relationship

Substances

Antineoplastic Agents
Oligopeptides