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

doi:10.1016/S0040-4020(01)00259-9

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

39 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 language	English
Pages (from-to)	3885-3890
Number of pages	6
Journal	Tetrahedron
Volume	57
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4020(01)00259-9
Publication status	Published - 2001 Apr 30
Externally published	Yes

Keywords

Biologically active compounds
Enzyme inhibitors
Marine metabolites
Steroids and sterols

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/S0040-4020(01)00259-9

Cite this

Fujita, M., Nakao, Y., Matsunaga, S., Seiki, M., Itoh, Y., Van Soest, R. W. M., Heubes, M., Faulkner, D. J., & Fusetani, N. (2001). 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. Tetrahedron, 57(18), 3885-3890. https://doi.org/10.1016/S0040-4020(01)00259-9

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, Yoichi; Matsunaga, Shigeki et al.
In: Tetrahedron, Vol. 57, No. 18, 30.04.2001, p. 3885-3890.

Research output: Contribution to journal › Article › peer-review

Fujita, M, Nakao, Y, Matsunaga, S, Seiki, M, Itoh, Y, Van Soest, RWM, Heubes, M, Faulkner, DJ & Fusetani, N 2001, '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', Tetrahedron, vol. 57, no. 18, pp. 3885-3890. https://doi.org/10.1016/S0040-4020(01)00259-9

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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.",

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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).",

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AU - Itoh, Yoshifumi

AU - Van Soest, Rob W.M.

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AU - Faulkner, D. John

AU - Fusetani, Nobuhiro

N1 - 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, ‘Research for the Future Program’ (JSPS-RFTF 96I00301). M. H. thanks the Deutsche Forschungsgemeinschaft for a fellowship (HE 3242/1-1).

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