Rhodocomatulin-type anthraquinones from the Australian marine invertebrates Clathria hirsuta and Comatula rotalaria

Khokhar, Shahan, Pierens, Gregory K., Hooper, John N. A., Ekins, Merrick G., Feng, Yunjiang and Davis, Rohan A. (2016) Rhodocomatulin-type anthraquinones from the Australian marine invertebrates Clathria hirsuta and Comatula rotalaria. Journal of Natural Products, 79 4: 946-953. doi:10.1021/acs.jnatprod.5b01029


Author Khokhar, Shahan
Pierens, Gregory K.
Hooper, John N. A.
Ekins, Merrick G.
Feng, Yunjiang
Davis, Rohan A.
Title Rhodocomatulin-type anthraquinones from the Australian marine invertebrates Clathria hirsuta and Comatula rotalaria
Formatted title
Rhodocomatulin-type anthraquinones from the Australian marine invertebrates Clathria hirsuta and Comatula rotalaria
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 1520-6025
0163-3864
Publication date 2016-04-22
Year available 2016
Sub-type Article (original research)
DOI 10.1021/acs.jnatprod.5b01029
Open Access Status Not Open Access
Volume 79
Issue 4
Start page 946
End page 953
Total pages 8
Place of publication Washington, DC United States
Publisher American Chemical Society
Collection year 2017
Language eng
Formatted abstract
Chemical investigations of an Australian sponge, Clathria hirsuta, from the Great Barrier Reef, have resulted in the isolation of two known anthraquinones, rhodocomatulin 5,7-dimethyl ether (1) and rhodocomatulin 7-methyl ether (2). Additionally, four new anthraquinone metabolites, 6-methoxyrhodocomatulin 7-methyl ether, 3-bromo-6-methoxy-12-desethylrhodocomatulin 7-methyl ether, 3-bromo-6-methoxyrhodocomatulin 7-methyl ether, and 3-bromorhodocomatulin 7-methyl ether (3–6), were also isolated and characterized. This is the first report of the rhodocomatulin-type anthraquinones from a marine sponge, as 1 and 2 were previously isolated from the marine crinoid genus Comatula. An additional chemical investigation of the marine crinoid Comatula rotalaria enabled the isolation of further quantities of 1 and 2, as well as two additional new crinoid metabolites, 12-desethylrhodocomatulin 5,7-dimethyl ether and 12-desethylrhodocomatulin 7-methyl ether (7 and 8). An NMR spectroscopic analysis of compounds 7 and 8 provided further insight into the rhodocomatulin planar structure and, together with the successful implementation of DFT-NMR calculations, confirmed that the rhodocomatulin metabolites existed as para rather than ortho quinones.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
Centre for Advanced Imaging Publications
 
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