| total synthesis of flustramine c via dimethylallyl rearrangement. | the marine natural product flustramine c from the bryozoan flustra foliacea was synthesized in five steps and 38% yield starting from nb-methyltryptamine. the key step is the biomimetic oxidation of the natural product deformylflustrabromine causing selective 1,2-rearrangement of the inverse prenyl group. by 1h,15n hmbc experiments, it is unambiguously shown that the reaction with t-buocl commences with chlorination of the side chain nitrogen. deformylflustrabromine itself was synthesized via da ... | 2007 | 17217285 |
| further studies on the chemistry of the flustra alkaloids from the bryozoan flustra foliacea. | since 1980, over a dozen novel brominated alkaloids, named flustramines, have been isolated from scandinavian and canadian collections of the marine bryozoan flustra foliacea. this paper describes the reisolation of the known compound dihydroflustramine c (1) and the isolation of 11 new flustramines (2-4, 6-13), including two dimers (12, 13) that may be isolation artifacts. together these compounds, some with an unexpected aryl substitution pattern, reveal an intricate network of metabolites pre ... | 2009 | 19785389 |
| the complete mitochondrial genome of flustra foliacea (ectoprocta, cheilostomata) - compositional bias affects phylogenetic analyses of lophotrochozoan relationships. | the phylogenetic relationships of the lophophorate lineages, ectoprocts, brachiopods and phoronids, within lophotrochozoa are still controversial. we sequenced an additional mitochondrial genome of the most species-rich lophophorate lineage, the ectoprocts. although it is known that there are large differences in the nucleotide composition of mitochondrial sequences of different lineages as well as in the amino acid composition of the encoded proteins, this bias is often not considered in phylog ... | 2011 | 22111761 |
| synthesis and evaluation of n(1)-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands. | in this study thirty-three novel indole derivatives were designed and synthesized based on the structure of deformylflustrabromine b (1), a metabolite isolated from the marine bryozoan flustra foliacea l. the syntheses were carried out using standard methodologies and in good yields. the molecules were tested for their affinities for the α4β2(∗), α3β4(∗), α7(∗) and (α1)(2)β1γδ nicotinic acetylcholine receptor (nachr) subtypes. binding assays showed that, among these ligands, compound 7c exhibite ... | 2012 | 22609074 |
| secondary metabolites from marine bryozoans. a review. | secondary metabolites from marine bryozoans are reviewed. two ctenosome bryozoans are dealt with, one, alcyonidium gelatinosum containing a sulfoxonium ion acting as hapten in an allergic contact dermatitis and the other, zoobotryon verticillatum yielding bromogramines. five cheilostome bryozoans have given rise to the isolation of unique secondary natural products. bugula neritina is the source of the antineoplastic bryostatins and bugula purple while flustra foliacea have yielded an array of b ... | 1985 | 3907226 |
| variation of brominated indoles and terpenoids within single and different colonies of the marine bryozoan flustra foliacea. | the variation of the brominated indole and diterpenoid content within single and different colonies of the bryozoan flustra foliacea was investigated. the secondary metabolite profile and concentrations of individual components of f. foliacea samples were established using gc-ms. samples from 17 different collecting sites were analyzed. the alkaloid and diterpene composition of f. foliacea varied greatly depending upon the site of collection. investigation of f. foliacea samples from a single si ... | 2004 | 15303321 |
| electron diffraction studies of the calcareous skeletons of bryozoans. | electron microscopy and electron diffraction were used to investigate mineral crystallites dissociated from the skeletal walls of six species belonging to the bryozoa, a phylum of predominantly marine colony-forming invertebrate animals. four cheilostome bryozoans (flustra foliacea, membranipora membranacea, thalamoporella novaehollandiae and cellarinella foveolata) and two cyclostomes (fasciculipora ramosa and hornera robusta) were analysed. in each case, an attempt was made to relate the cryst ... | 2002 | 11897358 |
| potentiation of human alpha4beta2 neuronal nicotinic receptors by a flustra foliacea metabolite. | the effects of various flustra foliacea metabolites on different types of human neuronal nicotinic acetylcholine receptors (nachrs) expressed in xenopus oocytes were investigated. whereas most of the compounds tested had a small blocking effect, one of them, deformylflustrabromine, selectively increased the current obtained in alpha4beta2 receptors when co-applied with acetylcholine (ach). the current increase was reversible and concentration-dependent. this potentiating effect was still present ... | 2005 | 15567570 |
| total syntheses of five indole alkaloids from the marine bryozoan flustra foliacea. | a general, efficient, and conceptually new approach to the total syntheses of marine-derived indole alkaloids, including (+/-)-flustramines a (1) and b (2), (+/-)-flustramides a (3) and b (4), and (+/-)-debromoflustramine b (5), is outlined. the key step in the syntheses involves the conjugated addition of an organomagnesium species derived from prenyl bromide to 2-hydroxyindolenines. compounds 1, 2, and 5 have been synthesized in five steps with 23%, 17%, and 16% overall yield, respectively, wh ... | 2001 | 11312946 |
| secondary metabolites of flustra foliacea and their influence on bacteria. | the north sea bryozoan flustra foliacea was investigated to determine its secondary metabolite content. gas chromatography-mass spectrometry analysis of a dichloromethane extract of the bryozoan enabled 11 compounds to be identified. preparative high-performance liquid chromatography of the extract resulted in the isolation of 10 brominated alkaloids (compounds 1 to 10) and one diterpene (compound 11). all of these compounds were tested to determine their activities in agar diffusion assays agai ... | 2003 | 12788752 |
| isolation and structure elucidation of deformylflustrabromine from the north sea bryozoan flustra foliacea. | the brominated pyrrolo[2,3-b]indole deformylflustrabromine was isolated as a new natural product from the bryozoan flustra foliacea, collected in the north sea. deformylflustrabromine appears to be the missing link in the biosynthetic sequence from flustrabromine to flustraminol a. flustramines a, d, and dihydroflustramine c were determined as other major constituents of the investigated sample. deformylflustrabromine is cytotoxic against the human colon cancer cell line hct-116 (ic50 5.8 microm ... | 2002 | 12562094 |
| flustramine inspired synthesis and biological evaluation of pyrroloindoline triazole amides as novel inhibitors of bacterial biofilms. | anti-biofilm agents have been developed based upon the flustramine family of alkaloids isolated from flustra foliacea. a garg interrupted fischer indolization reaction was employed to access a core pyrroloindoline scaffold that was subsequently employed to create a pyrroloindoline triazole amide library. screening for the ability to modulate biofilm formation against strains of gram-positive and gram-negative bacteria identified several compounds with low micromolar, non-toxic ic(50) values. | 2011 | 21674109 |
| marine alkaloids, 15. two alkaloids, flustramine e and debromoflustramine b, from the marine bryozoan flustra foliacea. | a new alkaloid, flustramine e [1], with inhibitory activity towards rhizotonia solani and botrytis cinerea was isolated by gas-phase extraction from the marine bryozoan flustra foliacea. the structure was determined as 3a,8a-cis-1-methyl-3a-(3-methyl-2- butenyl)-6-bromo-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole, based on spectroscopic investigations. another alkaloid, debromoflustramine b [2a], was detected in trace amounts and identified by comparison of the mass spectrum with that of a synth ... | 1994 | 7964794 |
| in silico ligand-receptor docking of potentially selective butyrylcholinesterase inhibitors structurally related to the marine natural product debromoflustramine b. | selective human butyrylcholinesterase (bche) inhibitors such as cymserine have shown considerable promise for restoring cognition in alzheimer's disease. recently, (-)-debromoflustramine b, 1, a hexahydropyrrolo-[2,3-b]indole natural product isolated from the marine bryozoan flustra foliacea, has demonstrated micromolar potency as a selective bche inhibitor. since (±)-demethyldebromoflustramine b, (±)-2, has an even lower ic(50), and the active enantiomer is (-)-2, derivatives of (-)-2 were cons ... | 2010 | 20632975 |
| prenylated indole alkaloids from flustra foliacea with subtype specific binding on nachrs. | several brominated indole alkaloids and a diterpene (1-7) were isolated from the dichloromethane extract of the north sea bryozoan flustra foliacea. alkaloid 4 is a new natural product, whose structure was elucidated by interpretation of spectroscopic data (nmr, mass, uv, and ir). all compounds were tested for their in vitro affinity towards the alpha4beta2* and alpha7* subtype of the neuronal nicotinic acetylcholine receptor (nachr) using radioligand binding assays. deformylflustrabromine (3) a ... | 2004 | 15490312 |
| four new bromotryptamine derivatives from the marine bryozoan flustra foliacea. | ten brominated alkaloids, 6-bromo-2-(1,1-dimethyl-2-propenyl)-1h-indole-3-carbaldehyde (1), n-(2-[6-bromo-2-(1,1-dimethyl-2-propenyl)-1h-indol-3-yl]ethyl)-n-methylmethanesulfonamide (2), deformylflustrabromine (3), flustrabromine (4), (3ar,8as)-6-bromo-3a-[(2e)-3,7-dimethyl-2,6-octadienyl]-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]-indol-7-ol (5), flustramine c (6), dihydroflustramine c (7), flustramine a (8), flustramine d (9), and flustraminol a (10), and the diterpene 4,6-bis(4-methylpent-3-en-1-y ... | 2002 | 12444689 |
| studies of swedish marine organisms. ii. muscle-relaxant alkaloids from the marine bryozoan flustra foliacea. | | 1983 | 6675420 |
| microbial diversity of cultivatable bacteria associated with the north sea bryozoan flustra foliacea. | the microbial diversity of cultivatable bacteria associated with the bryozoan species flustra foliacea from the north sea was investigated by a molecular approach. amplified ribosomal rna restriction analyses (ardra) and 16s rdna partial sequence analysis revealed differences in the composition of cultivatable bacteria populations from single bryozoan colonies collected from two different sampling sites in the north sea as well from one site taken at different points in time. whereas gamma-prote ... | 2001 | 11876370 |