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A Chemical Study of Cyclic Depsipeptides Produced by a Sponge-Derived Fungus

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Taro Amagata,^† Brandon I. Morinaka,^† Akiko Amagata,^† Karen Tenney,^† Frederick A. Valeriote,^‡ Emil Lobkovsky,^§ Jon Clardy, and Phillip Crews*^†

Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California Santa Cruz, Santa Cruz, California 95064, Henry Ford Health System, Department of Internal Medicine, Division of Hematology and Oncology, Detroit, Michigan 48202, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, and Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115

J. Nat. Prod., 2006, 69 (11), pp 1560–1565

DOI: 10.1021/np060178k

Publication Date (Web): October 19, 2006

†

University of California Santa Cruz.

‡

Henry Ford Health System.

Cornell University.

Harvard Medical School.

To whom correspondence should be addressed. Tel: (831) 459-2603. Fax: (831) 459-2935. E-mail: phil@chemistry.ucsc.edu.

Abstract

Two novel cyclic depsipeptides, guangomides A (1) and B (2), together with a new destruxin derivative (3) were isolated from the cytotoxic extract obtained from the saltwater culture of an unidentifiable sponge-derived fungus. The new structures were elucidated on the basis of analysis of extensive 1D and 2D NMR data sets, and the absolute configurations of 2S, 9S, 13S, 19S, 24R, 28R of 1 were determined on the basis of the combined X-ray and Marfey's method structure analysis. Identical absolute configurations were assumed for 2. The cytotoxicity of the extract was found to be due to brefeldin A, while 1 and 2 showed weak antibacterial activity against Staphylococcus epidermidis and Enterococcus durans.

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Published In Issue November 27, 2006
Received April 20, 2006

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Article

A Chemical Study of Cyclic Depsipeptides Produced by a Sponge-Derived Fungus

Abstract

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Recommend & Share

Related Content

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Cyclic Peptides from an Endophytic Fungus Obtained from a Mangrove Leaf (Kandelia candel)

Highly N-Methylated Linear Peptides Produced by an Atypical Sponge-Derived Acremonium sp.

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