Cyclodidemniserinol trisulfate, a sulfated serinolipid from the Palauan ascidian Didemnum guttatum that inhibits HIV-1 integrase.
[structure--see text] Bioassay-guided fractionation of extracts of the Palauan ascidian Didemnum guttatum led to the isolation of cyclodidemniserinol trisulfate (1) as an inhibitor of HIV-1 integrase, which is an attractive target for anti-retroviral chemotherapy. The structure of cyclodidemniserinol trisulfate (1), the stereochemistry of which was only partially determined, was elucidated by interpretation of NMR and mass spectral data.
Mitchell
S S
SS
Scripps Institution of Oceanography, University of California at San Diego, La Jolla 92093-0212, USA.
Rhodes
D
D
Bushman
F D
FD
Faulkner
D J
DJ
D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D001685:Biological Factors; D003587:Cytomegalovirus / Q000201:enzymology; D004264:DNA Topoisomerases, Type I / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D019427:HIV Integrase / Q000378:metabolism; D019428:HIV Integrase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D050356:Lipid Metabolism; D008055:Lipids / Q000737:chemistry / Q000302:isolation & purification; D008386:Marine Biology; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011412:Propanolamines; D011409:Propylene Glycols / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D013431:Sulfates / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D059004:Topoisomerase I Inhibitors; D014561:Urochordata / Q000737:chemistry*
D019380:Anti-HIV Agents; D001685:Biological Factors; D004791:Enzyme Inhibitors; D019428:HIV Integrase Inhibitors; D008055:Lipids; D011412:Propanolamines; D011409:Propylene Glycols; D013431:Sulfates; D059004:Topoisomerase I Inhibitors; D019427:HIV Integrase; D004264:DNA Topoisomerases, Type I; C072422:serinol