Abstract
Three new furanosesterterpene tetronic acids, sulawesins A-C (1-3), were isolated from a Psammocinia sp. marine sponge, along with the known compounds ircinins-1 (4) and -2 (5). Although ircinins-1 and -2 were previously isolated as (+)- or (-)-enantiomers from marine sponges, we isolated them as enantiomeric mixtures. Sulawesins A and B possess a new carbon skeleton with a 5-(furan-3-yl)-4-hydroxycyclopent-2-enone moiety and were also found to be diastereomeric mixtures of four isomers by an HPLC analysis with a chiral-phase column. Sulawesin C has a dimeric structure of ircinin-1 and is the first dimer in this family. USP7, a deubiquitinating enzyme, is an emergent target of cancer therapy, and the isolated compounds inhibited USP7 with IC50 values in the range of 2.7-4.6 μM.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Furans / chemistry
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Furans / isolation & purification*
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Furans / pharmacology*
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Humans
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Indonesia
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Inhibitory Concentration 50
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Marine Biology
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Molecular Structure
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Porifera / chemistry*
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Sesquiterpenes
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Sesterterpenes / chemistry
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Sesterterpenes / isolation & purification*
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Sesterterpenes / pharmacology*
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Stereoisomerism
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Structure-Activity Relationship
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Terpenes / chemistry
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Terpenes / isolation & purification*
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Terpenes / pharmacology*
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Ubiquitin Thiolesterase
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Ubiquitin-Specific Peptidase 7
Substances
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Furans
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Sesquiterpenes
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Sesterterpenes
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Terpenes
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ircinin-1
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sulawesin A
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sulawesin B
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sulawesin C
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USP7 protein, human
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Ubiquitin Thiolesterase
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Ubiquitin-Specific Peptidase 7
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tetronic acid