Isolation of a Cyclic Depsipetide, Aspergillicin F, and Synthesis of Aspergillicins with Innate Immune-Modulating Activity.
Innate immunity is the front line of self-defense against microbial infection. After searching for natural compounds that regulate innate immunity using an ex vivo Drosophila culture system, we identified a new cyclic depsipeptide, aspergillicin F, from the fungus Aspergillus sp., as an innate immune suppressor. The total synthesis and biological evaluation of the aspergillicin family, including aspergillicin F, were performed, revealing that slight structural differences in the side chains of amino acid residues alter innate immunity-regulating activity.
Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba-yama, Aoba-ku, Sendai 980-8578, Japan.
Haruhisa
H
Kikuchi
Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba-yama, Aoba-ku, Sendai 980-8578, Japan.
Tsuyoshi
T
Hoshikawa
Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba-yama, Aoba-ku, Sendai 980-8578, Japan.
Shimpei
S
Fujimura
Bioresource Laboratories, MicroBiopharm Japan Co., Ltd. (MBJ), 1808 Nakaizumi, Iwata, Shizuoka 438-0078, Japan.
Noriaki
N
Sakata
Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba-yama, Aoba-ku, Sendai 980-8578, Japan.
Shoichiro
S
Kurata
Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba-yama, Aoba-ku, Sendai 980-8578, Japan.
Yasuhiro
Y
Katou
Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba-yama, Aoba-ku, Sendai 980-8578, Japan.
Yoshiteru
Y
Oshima
D000818:Animals; D001230:Aspergillus / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004330:Drosophila; D042783:Endothelial Cells / Q000378:metabolism; D007113:Immunity, Innate; D007155:Immunologic Factors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D047630:Depsipeptides; D007155:Immunologic Factors; C000602739:aspergillicin F