Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Antimalarial bromophycolides J-Q from the Fijian red alga Callophycus serratus.

ABSTRACT: Bromophycolides J-Q (1-8) were isolated from extracts of the Fijian red alga Callophycus serratus and identified with 1D and 2D NMR spectroscopy and mass spectral analyses. These diterpene-benzoate macrolides represent two novel carbon skeletons and add to the 10 previously reported bromophycolides (9-18) from this alga. Among these 18 bromophycolides, several exhibited activities in the low micromolar range against the human malaria parasite Plasmodium falciparum.

SUBMITTER: Lane AL

PROVIDER: S-EPMC2707147 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Antimalarial bromophycolides J-Q from the Fijian red alga Callophycus serratus.

Lane Amy L AL Stout E Paige EP Lin An-Shen AS Prudhomme Jacques J Le Roch Karine K Fairchild Craig R CR Franzblau Scott G SG Hay Mark E ME Aalbersberg William W Kubanek Julia J

The Journal of organic chemistry 20090401 7

Bromophycolides J-Q (1-8) were isolated from extracts of the Fijian red alga Callophycus serratus and identified with 1D and 2D NMR spectroscopy and mass spectral analyses. These diterpene-benzoate macrolides represent two novel carbon skeletons and add to the 10 previously reported bromophycolides (9-18) from this alga. Among these 18 bromophycolides, several exhibited activities in the low micromolar range against the human malaria parasite Plasmodium falciparum. ...[more]

PMID: 19271727

Similar Datasets

Bromophycolides C-I from the Fijian red alga Callophycus serratus.

Project description:Bromophycolides C-I (1-7) were isolated from extracts of the Fijian red alga Callophycus serratus and identified by NMR and mass spectral techniques. These novel natural products share a carbon skeleton and biosynthetic origin with previously identified bromophycolides A (8) and B (9), which form a rare group of diterpene-benzoate macrolides. Bromophycolides C-I (1-7) displayed modest antineoplastic activity against a range of human tumor cell lines.

| S-EPMC2528861 | biostudies-literature

Callophycoic acids and callophycols from the Fijian red alga Callophycus serratus.

Project description:Callophycoic acids A-H (1-8) and callophycols A and B (9 and 10) were isolated from extracts of the Fijian red alga Callophycus serratus, and identified by NMR, X-ray, and mass spectral analyses. These natural products represent four novel carbon skeletons, providing the first examples of diterpene-benzoic acids and diterpene-phenols in macroalgae. Compounds 1-10 exhibited antibacterial, antimalarial, and anticancer activity, although they are less bioactive than diterpene-benzoate macrolides previously isolated from this red alga.

| S-EPMC3374858 | biostudies-literature

Antineoplastic diterpene-benzoate macrolides from the Fijian red alga Callophycus serratus.

Project description:[structures: see text] Three diterpene-benzoate natural products, with novel carbon skeletons and an unusual proposed biosynthesis, were isolated from extracts of the Fijian red alga Callophycus serratus and identified by a combination of X-ray crystallographic, NMR, and mass spectral analyses. Bromophycolide A (1) displayed cytotoxicity against several human tumor cell lines via specific apoptotic cell death. This represents the first discovery of natural products incorporating a diterpene and benzoate skeleton into a macrolide system.

| S-EPMC3374863 | biostudies-literature

Bioactive bromophycolides R-U from the Fijian red alga Callophycus serratus.

Project description:Four new bromophycolides, R-U (1-4), were isolated from the Fijian red alga Callophycus serratus and were identified by 1D and 2D NMR and mass spectroscopic analyses. These compounds expand the known structural variety of diterpene-benzoate macrolides and exhibited modest cytotoxicity toward selected human cancer cell lines. Bromophycolide S (2) also showed submicromolar activity against the human malaria parasite Plasmodium falciparum.

| S-EPMC3375676 | biostudies-literature

Bromophycoic acids: bioactive natural products from a Fijian red alga Callophycus sp.

Project description:Bioassay-guided fractionation of extracts from a Fijian red alga in the genus Callophycus resulted in the isolation of five new compounds of the diterpene-benzoate class. Bromophycoic acids A-E (1-5) were characterized by NMR and mass spectroscopic analyses and represent two novel carbon skeletons, one with an unusual proposed biosynthesis. These compounds display a range of activities against human tumor cell lines, malarial parasites, and bacterial pathogens including low micromolar suppression of MRSA and VREF.

| S-EPMC3474338 | biostudies-literature

Iodinated Meroditerpenes from a Red Alga Callophycus sp.

Project description:Unique iodine-containing meroditerpenes iodocallophycoic acid A (1) and iodocallophycols A-D (2-5) were discovered from the Fijian red alga Callophycus sp. Because flexibility of the molecular skeleton impaired full characterization of relative stereochemistries by NMR spectroscopy, a DFT-based theoretical model was developed to derive relevant interproton distances which were compared to those calculated from NOE measurements, yielding the relative stereochemistries. The correct 2S,6S,7S,10S,14S enantiomers were then identified by comparison of theoretical and experimental ECD spectra. Biological activities of these iodinated and brominated meroditerpenes and additional new, related bromophycoic acid F (6) and bromophycoic acid A methyl ester (7), were evaluated for relevant human disease targets. Iodocallophycoic acid A (1) showed moderate antibiotic activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF) with MIC values of 1.4 and 2.2 μg mL-1, respectively. It also potentiated the anti-MRSA activity of oxacillin in a synergistic fashion, resulting in an 8-fold increase in oxacillin potency, for a MIC of 16 μg mL-1.

| S-EPMC5538829 | biostudies-literature

Antibacterial neurymenolides from the Fijian red alga Neurymenia fraxinifolia.

Project description:Two novel alpha-pyrone macrolides, neurymenolides A (1) and B (2), were isolated from the Fijian red alga Neurymenia fraxinifolia and characterized using a combination of NMR and mass spectral analyses. These molecules represent only the second example of alpha-pyrone macrolides, with 1 existing as interchanging atropisomers due to restricted rotation about the alpha-pyrone ring system. Neurymenolide A (1) displayed moderately potent activities against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF).

| S-EPMC2646105 | biostudies-literature

Antimalarial Peptide and Polyketide Natural Products from the Fijian Marine Cyanobacterium Moorea producens.

Project description:A new cyclic peptide, kakeromamide B (1), and previously described cytotoxic cyanobacterial natural products ulongamide A (2), lyngbyabellin A (3), 18E-lyngbyaloside C (4), and lyngbyaloside (5) were identified from an antimalarial extract of the Fijian marine cyanobacterium Moorea producens. Compounds 1 and 1 exhibited moderate activity against Plasmodium falciparum blood-stages with EC50 values of 0.89 and 0.99 µM, respectively, whereas 3 was more potent with an EC50 value of 0.15 nM, respectively. Compounds 1, 4, and 5 displayed moderate liver-stage antimalarial activity against P. berghei liver schizonts with EC50 values of 1.1, 0.71, and 0.45 µM, respectively. The threading-based computational method FINDSITEcomb2.0 predicted the binding of 1 and 2 to potentially druggable proteins of Plasmodiumfalciparum, prompting formulation of hypotheses about possible mechanisms of action. Kakeromamide B (1) was predicted to bind to several Plasmodium actin-like proteins and a sortilin protein suggesting possible interference with parasite invasion of host cells. When 1 was tested in a mammalian actin polymerization assay, it stimulated actin polymerization in a dose-dependent manner, suggesting that 1 does, in fact, interact with actin.

| S-EPMC7142784 | biostudies-literature

Genome of the red alga Porphyridium purpureum.

Project description:The limited knowledge we have about red algal genomes comes from the highly specialized extremophiles, Cyanidiophyceae. Here, we describe the first genome sequence from a mesophilic, unicellular red alga, Porphyridium purpureum. The 8,355 predicted genes in P. purpureum, hundreds of which are likely to be implicated in a history of horizontal gene transfer, reside in a genome of 19.7 Mbp with 235 spliceosomal introns. Analysis of light-harvesting complex proteins reveals a nuclear-encoded phycobiliprotein in the alga. We uncover a complex set of carbohydrate-active enzymes, identify the genes required for the methylerythritol phosphate pathway of isoprenoid biosynthesis, and find evidence of sexual reproduction. Analysis of the compact, function-rich genome of P. purpureum suggests that ancestral lineages of red algae acted as mediators of horizontal gene transfer between prokaryotes and photosynthetic eukaryotes, thereby significantly enriching genomes across the tree of photosynthetic life.

| S-EPMC3709513 | biostudies-literature

Unusual antimalarial meroditerpenes from tropical red macroalgae.

Project description:Three antimalarial meroditerpenes have been isolated from two Fijian red macroalgae. The absolute stereochemistry of callophycolide A (1), a unique macrolide from Callophycus serratus, was determined using a combination of Mosher's ester analysis, circular dichroism analysis with a dimolybdenum tetraacetate complex, and conformational analysis using NOEs. In addition, two known tocopherols, ?-tocopherylhydroquinone (4) and ?-tocopherylhydroquinone (5), were isolated from Amphiroa crassa. By oxidizing 5 to the corresponding ?-tocopherylquinone (6), antimalarial activity against the human malaria parasite Plasmodium falciparum was increased by more than 20-fold.

| S-EPMC2939151 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data