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A small library of semisynthetic analogues of fuscol and eunicol have been prepared and evaluated for in vivo topical anti-inflammatory activity using the mouse-ear edema assay. The first glycosylation of fuscol and eunicol has been achieved using a modified Koenigs-Knorr glycosylation to synthesize...
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Marine diterpene glycosides (MDGs) respresent a small but highly significant group of the much larger class of marine diterpenes. The three well-studied examples of MDGs are eleutherobins, pseudopterosins and fuscosides, all of which exhibit extremely promising biological activity. The eleutherobins...
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Marine invertebrates have proven to be a rich source of secondary metabolites. The growing recognition that marine microorganisms associated with invertebrate hosts are involved in the biosynthesis of secondary metabolites offers new alternatives for the discovery and development of marine natural p...
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Gorgonian corals have proven to be a prolific source of a variety of biologically active terpenes. Corals of the genus Plexaurella are known to be the source of a diverse array of sesquiterpenes, and past reports have indicated variability in terpene content. This study involved an examination of th...
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LC-MS/MS-based screening of the dichloromethane extract of the gorgonian coral Pseudopterogorgia acerosa led to the isolation of a novel bis(pseudopterane) amine (1). The structural assignment of 1 was achieved by 1D and 2D NMR and mass spectrometry analysis. A biomimetic synthesis of 1 and the know...
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Gorgonian corals continue to provide a wealth of novel structures, many of which exhibit potentially useful biological activity. Notably, the families Briareidae, Gorgoniidae and Plexauridae have been demonstrated to contain a wide variety of natural products including steroids, acetogenins, sesquit...
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We recently reported that the biosynthesis of fuscol, a diterpene from the octocoral Eunicea fusca, is inducible by the application of plant signaling factors such as salicylic acid to the coral's algal symbiont. In this study, an mRNA differential display approach has been employed with the di...
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Novel lipidyl pseudopteranoids, lipidyl pseudopteranes A-F (1-6), have been isolated from the soft coral Pseudopterogorgia acerosa collected from the Bahamas. Structure elucidation of the six new compounds was based on 1D and 2D NMR data and mass spectrometry, and a biomimetic synthesis of 1 from ps...
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The close association between marine invertebrates, zooxanthellae, and numerous bacteria gives rise to the question of the identity of the actual producer of secondary metabolites. In fall of 2005, a widespread bleaching event occurred throughout the Caribbean Sea in which some colonies of the gorgo...
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This study examined the symbiotic microbiota of the hexacoral Cirrhipathes lutkeni using traditional plate culture, fluorescence in situ hybridization ( FISH) and 16S rDNA characterization. FISH counts for the whole coral (holobiont) showed a major presence of gamma-Proteobacteria (22%) and Actinoba...
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This study examined the microbiota associated with the marine azooxanthellate octocorals Leptogorgia minimata, Swiftia exertia, and Iciligorgia schrammi collected from moderate depths (45 m). Traditional aerobic plate culture, fluorescence in situ hybridization (FISH), and molecular identification o...
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This report describes a series of experiments designed to determine if terpene biosynthesis is inducible in two families of marine terpenes, pseudopterosins from the gorgonian coral Pseudopterogorgia elisabethae and fuscol from Eunicea fusca. Since we have recently shown that terpene biosynthesis is...
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The Bahamian octocoral Pseudopterogorgia elisabethae is the source of pseudopterosins, diterpene glycosides with potent anti-inflammatory activity. The first committed step in pseudopterosin biosynthesis comprises the cyclisation of the universal diterpene precursor geranylgeranyl diphosphate to eli...
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The pseudopterosins are a family of diterpene glycosides isolated from the gorgonian coral Pseudopterogorgia elisabethae. These metabolites exhibit potent anti-inflammatory activity, and this review describes our efforts to elucidate their biosynthetic origin. A radioactivity-guided isolation was us...
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Amphilectosins A and B have been identified from the organic extract of Pseudopterogorgia elisabethae collected in the Florida Keys, along with seco-pseudopterosins and pseudopterosins. The structures of the amphilectosins, "C-12-C-13 dehydro seco-pseudopterosins", suggested that these metabolites p...
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The diketopiperazine of DOPA was synthesized in high yield from the diketopiperazine of tyrosine using PC12 cell lysate, which expresses high levels of tyrosine hydroxylase. This represents the first use of this enzyme to prepare DOPA-containing peptides.