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

研究成果: Article

33 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3885-3890
ページ数6
ジャーナルTetrahedron
57
18
DOI
出版ステータスPublished - 2001 4 30
外部発表はい

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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