Sulawesins A-C, Furanosesterterpene Tetronic Acids That Inhibit USP7, from a Psammocinia sp. Marine Sponge
| Autor: | Nicole J. de Voogd, Nagwa M. Ammar, Hikaru Kato, Ahmed H. Afifi, Remy E. P. Mangindaan, Ahmed H. El-Desoky, Sachiko Tsukamoto, Mohammed S. Hifnawy, Ippei Kagiyama |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Sesterterpenes Stereochemistry Dimer Pharmaceutical Science Stereoisomerism Marine Biology Biology 01 natural sciences Analytical Chemistry Ubiquitin-Specific Peptidase 7 03 medical and health sciences chemistry.chemical_compound Inhibitory Concentration 50 Structure-Activity Relationship Drug Discovery Moiety Structure–activity relationship Molecule Animals Humans Furans Pharmacology Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Terpenes Organic Chemistry Diastereomer biology.organism_classification 0104 chemical sciences Porifera Sponge 030104 developmental biology Complementary and alternative medicine chemistry Indonesia Molecular Medicine Enantiomer Drug Screening Assays Antitumor Sesquiterpenes Ubiquitin Thiolesterase |
| Zdroj: | Journal of natural products. 80(7) |
| ISSN: | 1520-6025 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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