Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum

Reiko Sugiura, Ayako Kita, Nozomi Tsutsui, Osamu Muraoka, Kanako Hagihara, Nanae Umeda, Tatsuki Kunoh, Hirofumi Takada, Dai Hirose

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

By the newly developed assay method, the glycolipid Acremomannolipin A (1) was isolated from a filamentous fungus Acremonium strictum as a potential calcium signal modulator. The structure of 1 elucidated on the basis of intensive spectroscopic analyses as well as its degradation studies is quite unique: the d-mannopyranose is connected to d-mannitol through a β-glycoside linkage; all the hydroxyls in the mannose are highly masked as peresters with aliphatic acids, and this moiety is made hydrophobic, whereas the mannitol part exhibits a highly hydrophilic property. The compound (1) showed the characteristic bioactivity property, enabling calcineurin deletion cells to grow in the presence of Cl-, which would be caused by calcium signal modulating. The activity was so potent as to exert the effect at a concentration of 200 nM.

Original languageEnglish
Pages (from-to)6735-6739
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number21
DOIs
Publication statusPublished - Nov 1 2012
Externally publishedYes

Fingerprint

Acremonium
Glycolipids
Mannitol
Mannose
Fungi
Modulators
Calcium
Calcineurin
Glycosides
Bioactivity
Hydroxyl Radical
Assays
Fatty Acids
Degradation
acremomannolipin A

Keywords

  • Acremomannolipin A
  • Acremonium strictum
  • Calcium signal modulator
  • Glycolipid
  • Phenotypic screen

ASJC Scopus subject areas

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

Cite this

Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum. / Sugiura, Reiko; Kita, Ayako; Tsutsui, Nozomi; Muraoka, Osamu; Hagihara, Kanako; Umeda, Nanae; Kunoh, Tatsuki; Takada, Hirofumi; Hirose, Dai.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 21, 01.11.2012, p. 6735-6739.

Research output: Contribution to journalArticle

Sugiura, Reiko ; Kita, Ayako ; Tsutsui, Nozomi ; Muraoka, Osamu ; Hagihara, Kanako ; Umeda, Nanae ; Kunoh, Tatsuki ; Takada, Hirofumi ; Hirose, Dai. / Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum. In: Bioorganic and Medicinal Chemistry Letters. 2012 ; Vol. 22, No. 21. pp. 6735-6739.
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