Microsporins A and B: new histone deacetylase inhibitors from the marine-derived fungus Microsporum cf. gypseum and the solid-phase synthesis of microsporin A

Wenxin Gu; Mercedes Cueto; Paul R. Jensen; William Fenical; Richard B. Silverman

doi:10.1016/j.tet.2007.04.025

Microsporins A and B: new histone deacetylase inhibitors from the marine-derived fungus Microsporum cf. gypseum and the solid-phase synthesis of microsporin A

Wenxin Gu, Mercedes Cueto, Paul R. Jensen, William Fenical^*, Richard B. Silverman

^*Corresponding author for this work

Chemistry

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

73 Scopus citations

Abstract

Two new cyclic peptides, microsporins A and B (7 and 8), were isolated from culture extracts of the marine-derived fungus Microsporum cf. gypseum obtained from a sample of the bryozoan Bugula sp. collected in the U.S. Virgin Islands. The structures of the new compounds were determined by extensive interpretation of 2D NMR data and by chemical methods. Microsporins A and B are potent inhibitors of histone deacetylase and demonstrate cytotoxic activity against human colon adenocarcinoma (HCT-116), as well as against the National Cancer Institute 60 cancer cell panel. The total synthesis of microsporin A on solid-phase is also reported.

Original language	English (US)
Pages (from-to)	6535-6541
Number of pages	7
Journal	Tetrahedron
Volume	63
Issue number	28
DOIs	https://doi.org/10.1016/j.tet.2007.04.025
State	Published - Jul 9 2007

Keywords

Aoda
Cyclic tetrapeptide
Cytotoxins
Histone deacetylase
Marine fungus
Microsporum gypseum
Solid-phase synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

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

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10.1016/j.tet.2007.04.025

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title = "Microsporins A and B: new histone deacetylase inhibitors from the marine-derived fungus Microsporum cf. gypseum and the solid-phase synthesis of microsporin A",

abstract = "Two new cyclic peptides, microsporins A and B (7 and 8), were isolated from culture extracts of the marine-derived fungus Microsporum cf. gypseum obtained from a sample of the bryozoan Bugula sp. collected in the U.S. Virgin Islands. The structures of the new compounds were determined by extensive interpretation of 2D NMR data and by chemical methods. Microsporins A and B are potent inhibitors of histone deacetylase and demonstrate cytotoxic activity against human colon adenocarcinoma (HCT-116), as well as against the National Cancer Institute 60 cancer cell panel. The total synthesis of microsporin A on solid-phase is also reported.",

keywords = "Aoda, Cyclic tetrapeptide, Cytotoxins, Histone deacetylase, Marine fungus, Microsporum gypseum, Solid-phase synthesis",

author = "Wenxin Gu and Mercedes Cueto and Jensen, {Paul R.} and William Fenical and Silverman, {Richard B.}",

note = "Funding Information: We appreciate financial support provided by the National Cancer Institute under grants CA44848 and CA55060 (W.F.) and CA116971 (R.B.S.). M.C. acknowledges a post-doctoral fellowship of the Ministerio de Educacion of Spain. We gratefully acknowledge Chris Kauffman (SIO) for his assistance with the fermentation aspects of this project. ",

year = "2007",

month = jul,

day = "9",

doi = "10.1016/j.tet.2007.04.025",

language = "English (US)",

volume = "63",

pages = "6535--6541",

journal = "Tetrahedron",

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TY - JOUR

T1 - Microsporins A and B

T2 - new histone deacetylase inhibitors from the marine-derived fungus Microsporum cf. gypseum and the solid-phase synthesis of microsporin A

AU - Gu, Wenxin

AU - Cueto, Mercedes

AU - Jensen, Paul R.

AU - Fenical, William

AU - Silverman, Richard B.

N1 - Funding Information: We appreciate financial support provided by the National Cancer Institute under grants CA44848 and CA55060 (W.F.) and CA116971 (R.B.S.). M.C. acknowledges a post-doctoral fellowship of the Ministerio de Educacion of Spain. We gratefully acknowledge Chris Kauffman (SIO) for his assistance with the fermentation aspects of this project.

PY - 2007/7/9

Y1 - 2007/7/9

N2 - Two new cyclic peptides, microsporins A and B (7 and 8), were isolated from culture extracts of the marine-derived fungus Microsporum cf. gypseum obtained from a sample of the bryozoan Bugula sp. collected in the U.S. Virgin Islands. The structures of the new compounds were determined by extensive interpretation of 2D NMR data and by chemical methods. Microsporins A and B are potent inhibitors of histone deacetylase and demonstrate cytotoxic activity against human colon adenocarcinoma (HCT-116), as well as against the National Cancer Institute 60 cancer cell panel. The total synthesis of microsporin A on solid-phase is also reported.

AB - Two new cyclic peptides, microsporins A and B (7 and 8), were isolated from culture extracts of the marine-derived fungus Microsporum cf. gypseum obtained from a sample of the bryozoan Bugula sp. collected in the U.S. Virgin Islands. The structures of the new compounds were determined by extensive interpretation of 2D NMR data and by chemical methods. Microsporins A and B are potent inhibitors of histone deacetylase and demonstrate cytotoxic activity against human colon adenocarcinoma (HCT-116), as well as against the National Cancer Institute 60 cancer cell panel. The total synthesis of microsporin A on solid-phase is also reported.

KW - Aoda

KW - Cyclic tetrapeptide

KW - Cytotoxins

KW - Histone deacetylase

KW - Marine fungus

KW - Microsporum gypseum

KW - Solid-phase synthesis

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U2 - 10.1016/j.tet.2007.04.025

DO - 10.1016/j.tet.2007.04.025

M3 - Article

AN - SCOPUS:34249290099

SN - 0040-4020

VL - 63

SP - 6535

EP - 6541

JO - Tetrahedron

JF - Tetrahedron

IS - 28

ER -

Microsporins A and B: new histone deacetylase inhibitors from the marine-derived fungus Microsporum cf. gypseum and the solid-phase synthesis of microsporin A

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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