Oxidative processes in the Australian marine sponge Plakinastrella clathrata: Isolation of plakortolides with oxidatively modified side chains

Yong, Ken W. L., Lambert, Lynette K., Hayes, Patricia Y., De Voss, James J. and Garson, Mary J. (2012) Oxidative processes in the Australian marine sponge Plakinastrella clathrata: Isolation of plakortolides with oxidatively modified side chains. Journal of Natural Products, 75 3: 351-360. doi:10.1021/np200619q


Author Yong, Ken W. L.
Lambert, Lynette K.
Hayes, Patricia Y.
De Voss, James J.
Garson, Mary J.
Title Oxidative processes in the Australian marine sponge Plakinastrella clathrata: Isolation of plakortolides with oxidatively modified side chains
Formatted title
Oxidative processes in the Australian marine sponge Plakinastrella clathrata: Isolation of plakortolides with oxidatively modified side chains
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 0163-3864
1520-6025
Publication date 2012-03-23
Year available 2011
Sub-type Article (original research)
DOI 10.1021/np200619q
Open Access Status Not yet assessed
Volume 75
Issue 3
Start page 351
End page 360
Total pages 10
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Formatted abstract
Sixteen new cyclic peroxides (1−16) with a plakortolide skeleton and the methyl ester derivative of a didehydroplakinic acid (17) were isolated from the Australian sponge Plakinastrella clathrata Kirkpatrick, 1900. Structural elucidation and configurational assignments were based on spectroscopic analysis and comparison with data for previously isolated plakortolides and revealed both phenyl- and methyl-terminating side chains attached to the plakortolide core. Plakortoperoxides A−D (5−8) each
contained a second 1,2-dioxine ring; a cis configuration for the side chain endoperoxide ring was determined by a low-temperature NMR study and by comparison of chemical shift values with those of reported compounds. An enantioselective HPLC study compared natural plakortoperoxide A with a synthetic sample prepared by cyclization of plakortolide P with singlet oxygen and revealed that the natural sample was a mixture of cis diastereomers at C-15/C18. Four other cyclic peroxides (9−12) possessed a C9-truncated side chain terminating in a formyl or carboxylic acid functionality, suggesting that these metabolites may have been formed by oxidative cleavage of the Δ9,10 bond of dienefunctionalized plakortolides. A final group of four metabolites (13−16) with hydroxy or the rare hydroperoxy functionality
unexpectedly revealed a C8 side chain, while the ester (17) represents further structural variation within the growing family of cyclic peroxy sponge metabolites.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Publication Date (Web): November 3, 2011

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
School of Chemistry and Molecular Biosciences
Centre for Advanced Imaging Publications
 
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Created: Mon, 14 Nov 2011, 19:40:44 EST by Sandrine Ducrot on behalf of Centre for Advanced Imaging