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Wednesday 6 July 2016

Darwinolide

Abstract Image



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.

 Figure



 NMR Data for Darwinolide (CDCl3)
positionδC, typeaδH (J in Hz)bCOSYHMBCROESY
1a38.6, CH21.08, m1b,2a,2b2,3,4,9,18,19,20 
b 1.54, m1a,2a,2b2,3,4,5,10,20 
2a18.7, CH21.50, m1b,3a,3b1,4,10 
b 1.59, m1a,1b,3b4 
3a39.2, CH21.11, m2a2,4,18,19 
b 1.37, m2a,2b4,10,18,19 
430.8, C    
5a50.5, CH21.08, d (14.1)5b3,4,9,18,19,20 
b 1.38, d (14.1)5a1,2,3,4,11,18,19,20 
615.6, CH32.39, d (2.3)147,8,9,13,1720
7119.5, C    
8159.5, C    
957.3, CH2.08, m11a,11b1,5,6,7,8,10,11,12,2014
1036.0, C    
11a19.2, CH21.42, m9,12b8,9,10,12,13,16 
b 1.64, m9,12a,12b8,9,12,13 
12a25.6, CH21.92, m11b,139,13,14,16 
b 1.19, m11a,11b13,14,16 
1343.2, CH2.24, m12a,14,1612,16 
1445.1, CH3.93, tt (7.0, 2.4)6,13,1579,13,15
15103.9, CH6.07, d (7.0)147,14,1714
16103.8, CH5.93, s1312,13,14,15,2112a
17167.7, C    
1833.9, CH30.86, s192,3,4,5,10,1919
1928.5, CH30.98, s183,4,5,10,1818
2022.1, CH31.14, s 1,5,9,106
21169.7, C    
2221.2, CH32.08, s 16,21 
a
Recorded at 125 MHz.
b
Recorded at 500 MHz.


 http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2016/orlef7.2016.18.issue-11/acs.orglett.6b00979/20160628/images/large/ol-2016-009793_0003.jpeg


 

 

 

 

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

Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE205, Tampa, Florida 33620, United States
Center for Drug Discovery and Innovation, University of South Florida, 3720 Spectrum Boulevard, Suite 303, Tampa, Florida 33612, United States
§ Department of Cell Biology, Microbiology and Molecular Biology, University of South Florida, 4202 East Fowler Avenue, ISA2015, Tampa, Florida 33620, United States
Department of Biology, University of Alabama at Birmingham, Birmingham, Alabama 35294, United States
Org. Lett., 2016, 18 (11), pp 2596–2599
DOI: 10.1021/acs.orglett.6b00979
http://pubs.acs.org/doi/full/10.1021/acs.orglett.6b00979
*E-mail: bjbaker@usf.edu.







 



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