Ceylonins A–F, Spongian Diterpene Derivatives That Inhibit RANKL-Induced Formation of Multinuclear Osteoclasts, from the Marine Sponge Spongia ceylonensis
| Autor: | Yuki Hitora, Nicole J. de Voogd, Ahmed H. El-Desoky, Remy E. P. Mangindaan, Fitje Losung, Hikaru Kato, Sachiko Tsukamoto, Ippei Kagiyama |
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| Rok vydání: | 2016 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Metabolite Osteoclasts Pharmaceutical Science Ring (chemistry) 01 natural sciences Analytical Chemistry chemistry.chemical_compound Drug Discovery Animals Nuclear Magnetic Resonance Biomolecular Acrylic acid Pharmacology Molecular Structure Bicyclic molecule biology 010405 organic chemistry RANK Ligand Organic Chemistry biology.organism_classification Spongia Porifera 0104 chemical sciences 010404 medicinal & biomolecular chemistry Sponge Complementary and alternative medicine chemistry Indonesia RANKL biology.protein Molecular Medicine Diterpenes Diterpene |
| Zdroj: | Journal of Natural Products. 80:90-95 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.6b00725 |
| Popis: | Six new spongian diterpene derivatives, ceylonins A–F (1–6), were isolated from the Indonesian marine sponge Spongia ceylonensis along with spongia-13(16),14-dien-19-oic acid (7). They contained three additional carbons in ring D to supply an ether-bridged bicyclic ring system. Their structures were elucidated by analyzing NMR spectroscopic data and calculated ECD spectra in comparison to experimental ECD spectra. The bicyclic ring system may be derived from the major metabolite 7 and a C3 unit (an acrylic acid equivalent) through an intermolecular Diels–Alder reaction, which was experimentally supported by the formation of 1–6 from 7 and acrylic acid. The inhibitory effects of the isolated compounds on the RANKL-induced formation of multinuclear osteoclasts in RAW264 macrophages were examined. |
| Databáze: | OpenAIRE |
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