Asteropine A, a Sialidase-Inhibiting Conotoxin-like Peptide from the Marine Sponge Asteropus simplex

Kentaro Takada, Toshiyuki Hamada, Hiroshi Hirota, Youichi Nakao, Shigeki Matsunaga, Rob W M van Soest, Nobuhiro Fusetani

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Marine sponges contain structurally intriguing and biologically active peptides of nonribosomal peptide synthase origin, often containing amino acids with novel structures. Here we report the discovery of asteropine A (APA), a cystine knot to be isolated from marine sponges. The solution structure of APA as determined by NMR belongs to the four-loop class of cystine knots similar to those of some conotoxins and spider toxins. However, the highly negatively charged surface of APA is uncommon among other cystine knots. APA competitively inhibits bacterial sialidases, but not a viral sialidase. APA was inactive against all other enzymes tested and did not have any apparent antitumor activity. Our data suggest that APA and other knotting peptides may be important leads for antibacterial and even antiviral drug development.

Original languageEnglish
Pages (from-to)569-574
Number of pages6
JournalChemistry and Biology
Volume13
Issue number6
DOIs
Publication statusPublished - 2006 Jun
Externally publishedYes

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Conotoxins
Cystine
Neuraminidase
Porifera
Peptides
Spiders
Antiviral Agents
Nuclear magnetic resonance
Amino Acids
Enzymes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Asteropine A, a Sialidase-Inhibiting Conotoxin-like Peptide from the Marine Sponge Asteropus simplex. / Takada, Kentaro; Hamada, Toshiyuki; Hirota, Hiroshi; Nakao, Youichi; Matsunaga, Shigeki; van Soest, Rob W M; Fusetani, Nobuhiro.

In: Chemistry and Biology, Vol. 13, No. 6, 06.2006, p. 569-574.

Research output: Contribution to journalArticle

Takada, Kentaro ; Hamada, Toshiyuki ; Hirota, Hiroshi ; Nakao, Youichi ; Matsunaga, Shigeki ; van Soest, Rob W M ; Fusetani, Nobuhiro. / Asteropine A, a Sialidase-Inhibiting Conotoxin-like Peptide from the Marine Sponge Asteropus simplex. In: Chemistry and Biology. 2006 ; Vol. 13, No. 6. pp. 569-574.
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