@article{de93641f61ef4301b9c94e3df965933f,
title = "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",
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.",
keywords = "Biologically active compounds, Enzyme inhibitors, Marine metabolites, Steroids and sterols",
author = "Masaki Fujita and Yoichi Nakao and Shigeki Matsunaga and Motoharu Seiki and Yoshifumi Itoh and {Van Soest}, {Rob W.M.} and Markus Heubes and Faulkner, {D. John} and Nobuhiro Fusetani",
note = "Funding Information: We are indebted to the crew of R/V Toyoshio-maru of Hiroshima University for assistance in collection of the sponge samples. This work was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture of Japan, and Japan Society for the Promotion of Science, {\textquoteleft}Research for the Future Program{\textquoteright} (JSPS-RFTF 96I00301). M. H. thanks the Deutsche Forschungsgemeinschaft for a fellowship (HE 3242/1-1).",
year = "2001",
month = apr,
day = "30",
doi = "10.1016/S0040-4020(01)00259-9",
language = "English",
volume = "57",
pages = "3885--3890",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Ltd",
number = "18",
}
