Darwinolide, a New Diterpene Scaffold That Inhibits Methicillin-Resistant Staphylococcus aureus Biofilm from the Antarctic Sponge Dendrilla membranosa

Jacqueline L von Salm; Christopher G Witowski; Renee M Fleeman; James B McClintock; Charles D Amsler; Lindsey N Shaw; Bill J Baker

doi:10.1021/acs.orglett.6b00979

Darwinolide, a New Diterpene Scaffold That Inhibits Methicillin-Resistant Staphylococcus aureus Biofilm from the Antarctic Sponge Dendrilla membranosa

Org Lett. 2016 Jun 3;18(11):2596-9. doi: 10.1021/acs.orglett.6b00979. Epub 2016 May 13.

Authors

Jacqueline L von Salm^{1

2}, Christopher G Witowski^{1

2}, Renee M Fleeman^{2

3}, James B McClintock⁴, Charles D Amsler⁴, Lindsey N Shaw^{2

3}, Bill J Baker^{1

2}

Affiliations

¹ Department of Chemistry, University of South Florida , 4202 East Fowler Avenue, CHE205, Tampa, Florida 33620, United States.
² Center for Drug Discovery and Innovation, University of South Florida , 3720 Spectrum Boulevard, Suite 303, Tampa, Florida 33612, United States.
³ Department of Cell Biology, Microbiology and Molecular Biology, University of South Florida , 4202 East Fowler Avenue, ISA2015, Tampa, Florida 33620, United States.
⁴ Department of Biology, University of Alabama at Birmingham , Birmingham, Alabama 35294, United States.

Abstract

A new rearranged spongian diterpene, darwinolide, has been isolated from the Antarctic Dendroceratid sponge Dendrilla membranosa. Characterized on the basis of spectroscopic and crystallographic analysis, the central seven-membered ring is hypothesized to originate from a ring-expansion of a spongian precursor. Darwinolide displays 4-fold selectivity against the biofilm phase of methicillin-resistant Staphylococcus aureus compared to the planktonic phase and may provide a scaffold for the development of therapeutics for this difficult to treat infection.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Animals
Antarctic Regions
Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology
Biofilms / drug effects*
Cell Line
Diterpenes / chemistry*
Diterpenes / isolation & purification
Diterpenes / pharmacology
Inhibitory Concentration 50
Methicillin-Resistant Staphylococcus aureus / drug effects*
Methicillin-Resistant Staphylococcus aureus / growth & development
Mice
Microbial Sensitivity Tests
Molecular Structure
Porifera / chemistry

Substances

Anti-Bacterial Agents
Diterpenes

Abstract

Publication types

MeSH terms

Substances

Grants and funding