Total Synthesis of (+)-Papuamine:  An Antifungal Pentacyclic Alkaloid from a Marine Sponge, <i>Haliclona </i>sp.

Barrett, Anthony G. M.; Boys, Mark L.; Boehm, Terri L.

doi:10.1021/jo951413z

Cited by 46 publications

(18 citation statements)

References 52 publications

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“…Sponges are a significant source of new bioactive metabolites and while there are no reports of bioactive metabolites being isolated from Haliclona simulans , over 190 metabolites have been isolated from other Haliclona species (Yu et al ., 2006). These compounds have a wide range of biological activities, including antifouling (Devi et al ., 1998; Sera et al ., 2002), antimicrobial (Clark et al ., 2001; Richelle‐Maurer et al ., 2001), antifungal (Barrett et al ., 1996; Clark et al ., 2001), antimalarial (Sakai et al ., 1986) and cytotoxic activities (Erickson et al ., 1997; Rashid et al ., 2000). The range of compounds isolated from Haliclona sp.…”

Section: Introductionmentioning

confidence: 99%

Diversity of microbes associated with the marine sponge, Haliclona simulans, isolated from Irish waters and identification of polyketide synthase genes from the sponge metagenome

Kennedy

Codling²,

Jones

et al. 2008

Environmental Microbiology

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Samples of the sponge Haliclona simulans were collected from Irish waters and subjected to a culture-independent analysis to determine the microbial, polyketide synthase (PKS) and non-ribosomal peptide synthase (NRPS) diversity. 16S rRNA gene libraries were prepared from total sponge, bacterial enriched sponge and seawater samples. Eight phyla from the Bacteria were detected in the sponge by phylogenetic analyses of the 16S rRNA gene libraries. The most abundant phylum in the total sponge library was the Proteobacteria (86%), with the majority of these clones being from the gamma-Proteobacteria (77%); two groups of clones were dominant and together made up 69% of the total. Both of these groups were related to other sponge-derived microbes and comprised novel genera. Within the other bacterial phyla groups of clones representing novel candidate genera within the phyla Verrucomicrobia and Lentisphaerae were also found. Selective enrichment of the bacterial component of the sponge prior to 16S rRNA gene analysis resulted in a 16S rRNA gene library dominated by a novel genus of delta-Proteobacteria, most closely related to the Bdellovibrio. The potential for the sponge microbiota to produce secondary metabolites was also analysed by polymerase chain reaction amplification of PKS and NRPS genes. While no NRPS sequences were isolated seven ketosynthase (KS) sequences were obtained from the sponge metagenome. Analyses of these clones revealed a diverse collection of PKS sequences which were most closely affiliated with PKS from members of the Cyanobacteria, Myxobacteria and Dinoflagellata.

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Section: Introductionmentioning

confidence: 99%

Diversity of microbes associated with the marine sponge, Haliclona simulans, isolated from Irish waters and identification of polyketide synthase genes from the sponge metagenome

Kennedy

Codling²,

Jones

et al. 2008

Environmental Microbiology

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“…Our route to trans - 4 and trans - 5 began from the known chiral racemic diols, 14a-b , 9 themselves prepared through Diels-Alder reaction of dimethyl fumarate with the appropriate dienes, followed by LiAlH 4 reduction ( 13→14 ). As shown in Scheme 3, diols 14a-b were converted to ketones 19a-b using methods analogous to those employed in the preparation of trans -bicyclo[4.3.0]non-3-en-8-one 10. Thus, treatment of 14a-b with p -TsCl in pyridine at 0 °C afforded ditosylates 15a-b , which were then subjected, without further purification, to the action of ethanolic solutions of sodium cyanide, under reflux.…”

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confidence: 99%

Syntheses of isomerically pure reference octalins and hydrindanes

Lee

Kim

2009

Tetrahedron Letters

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“…The genus of Haliclona sponges are known for their high chemical various secondary metabolites with interesting biological activities (Faulkner 2002 ) including the antifungal (Barrett et al 1996 ; Clark et al 2001 ; Wattanadilok et al 2007 ), antileishmanial (Dube et al 2007 ), antioxidant (Regoli et al 2004 ), cytotoxic (Erickson et al 1997 ; Fusetani et al 1989 ) and other activities (Hattori et al 1998 ; Randazzo et al 2001 ; Lakshmi et al 2009 ; Roper et al 2009 ).…”

Section: Resultsmentioning

confidence: 99%

Activity of Haliscosamine against Fusarium oxysporum f.sp. melonis: in vitro and in vivo analysis

et al. 2015

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Marine sponges are a potential source of new molecules with diverse biological activities. We have previously isolated a sphingosine derivative, (9Z)-2-amino-docos-9-ene-1,3,13,14-tetraol (Haliscosamine) from the Moroccan sea sponge Haliclona viscosa. The aim of this study was to test Haliscosamine in vitro and in vivo for its antifungal activity against Fusarium oxysporum f.sp. melonis causing fusarium wilt of melon.Overall, in vitro test showed that haliscosamine has a similar effect as DESOGERME SP VEGETAUX®. In addition, in vivo showed a significant effect against Fusarium oxysporum f.sp. melonis. Taking to gather, our results suggest that haliscosamine constitutes a potential candidate against Fusarium oxysporum f.sp. melonis and the possibility to use in phytopathology.

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Total Synthesis of (+)-Papuamine: An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp.

Cited by 46 publications

References 52 publications

Diversity of microbes associated with the marine sponge, Haliclona simulans, isolated from Irish waters and identification of polyketide synthase genes from the sponge metagenome

Diversity of microbes associated with the marine sponge, Haliclona simulans, isolated from Irish waters and identification of polyketide synthase genes from the sponge metagenome

Syntheses of isomerically pure reference octalins and hydrindanes

Activity of Haliscosamine against Fusarium oxysporum f.sp. melonis: in vitro and in vivo analysis

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