Isolation and structure elucidation of two phosphorylated sterol sulfates, MT1-MMP inhibitors from a marine sponge Cribrochalina sp.

Revision of the structures of haplosamates A and B

Masaki Fujita, Youichi Nakao, Shigeki Matsunaga, Motoharu Seiki, Yoshifumi Itoh, Rob W M Van Soest, Markus Heubes, D. John Faulkner, Nobuhiro Fusetani

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Two inhibitors of membrane-type matrix metalloproteinase (MT1-MMP) were isolated from a marine sponge Cribrochalina sp. Their structures were elucidated as unusual phosphorylated sterol sulfates by spectroscopic and chemical methods. One of the sterol sulfates was found to be identical to haplosamate A, whose structure was previously proposed to be a steroidal sulfamate ester, which led to structure revisions of both haplosamates A and B. The absolute stereochemistry of haplosamate A was determined by chemical transformation and the modified Mosher's method. The sterol sulfates inhibited MT1-MMP with IC50 values of 150 and 160 μg/mL, respectively.

Original languageEnglish
Pages (from-to)3885-3890
Number of pages6
JournalTetrahedron
Volume57
Issue number18
DOIs
Publication statusPublished - 2001 Apr 30
Externally publishedYes

Fingerprint

Matrix Metalloproteinase 14
Matrix Metalloproteinase Inhibitors
Porifera
Sterols
Sulfates
Membrane-Associated Matrix Metalloproteinases
Stereochemistry
Inhibitory Concentration 50
Esters

Keywords

  • Biologically active compounds
  • Enzyme inhibitors
  • Marine metabolites
  • Steroids and sterols

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Isolation and structure elucidation of two phosphorylated sterol sulfates, MT1-MMP inhibitors from a marine sponge Cribrochalina sp. Revision of the structures of haplosamates A and B. / Fujita, Masaki; Nakao, Youichi; Matsunaga, Shigeki; Seiki, Motoharu; Itoh, Yoshifumi; Van Soest, Rob W M; Heubes, Markus; Faulkner, D. John; Fusetani, Nobuhiro.

In: Tetrahedron, Vol. 57, No. 18, 30.04.2001, p. 3885-3890.

Research output: Contribution to journalArticle

Fujita, Masaki ; Nakao, Youichi ; Matsunaga, Shigeki ; Seiki, Motoharu ; Itoh, Yoshifumi ; Van Soest, Rob W M ; Heubes, Markus ; Faulkner, D. John ; Fusetani, Nobuhiro. / Isolation and structure elucidation of two phosphorylated sterol sulfates, MT1-MMP inhibitors from a marine sponge Cribrochalina sp. Revision of the structures of haplosamates A and B. In: Tetrahedron. 2001 ; Vol. 57, No. 18. pp. 3885-3890.
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