title: Ceylonins A-F, Spongian Diterpene Derivatives That Inhibit RANKL-Induced Formation of Multinuclear Osteoclasts, from the Marine Sponge Spongia ceylonensis.
abstract: 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 C3unit (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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University , Oe-honmachi 5-1, Kumamoto 862-0973, Japan.
authors.forename: Ahmed H
authors.initials: AH
authors.lastname: El-Desoky
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University , Oe-honmachi 5-1, Kumamoto 862-0973, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Kato
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University , Oe-honmachi 5-1, Kumamoto 862-0973, Japan.
authors.forename: Ippei
authors.initials: I
authors.lastname: Kagiyama
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University , Oe-honmachi 5-1, Kumamoto 862-0973, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Hitora
authors.affiliation: Faculty of Fisheries and Marine Science, Sam Ratulangi University , Kampus Bahu, Manado 95115, Indonesia.
authors.forename: Fitje
authors.initials: F
authors.lastname: Losung
authors.affiliation: Faculty of Fisheries and Marine Science, Sam Ratulangi University , Kampus Bahu, Manado 95115, Indonesia.
authors.forename: Remy E P
authors.initials: RE
authors.lastname: Mangindaan
authors.affiliation: Naturalis Biodiversity Center , P.O. Box 9517, 2300 RA Leiden, The Netherlands.
authors.forename: Nicole J
authors.initials: NJ
authors.lastname: de Voogd
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University , Oe-honmachi 5-1, Kumamoto 862-0973, Japan.
authors.forename: Sachiko
authors.identifier: 0000-0002-7993-381X
authors.initials: S
authors.lastname: Tsukamoto
mesh_terms: D000818:Animals; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007214:Indonesia; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010010:Osteoclasts / Q000737:chemistry / Q000187:drug effects*; D011161:Porifera / Q000737:chemistry*; D053245:RANK Ligand / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D004224:Diterpenes; D053245:RANK Ligand