Brominated Compounds from Marine Sponges of the Genus Aplysina and a Compilation of Their 13C NMR Spectral Data

Lira, Narlize Silva; Montes, Ricardo Carneiro; Tavares, Josean Fechine; Silva, Marcelo Sobral da; Cunha, Emídio Vasconcelos Leitão da; Athayde-Filho, Petrônio Filgueiras de; Rodrigues, Luís Cézar; Dias, Celidarque da Silva; Barbosa-Filho, José Maria

doi:10.3390/md9112316

Cited by 50 publications

(47 citation statements)

References 132 publications

(137 reference statements)

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“…Marine organisms have played a relevant role among the natural products. They make many secondary metabolites with broad chemical diversity and complexity and with great pharmaceutical potential [3,4,5], such as conotoxins from cone snails [6] and compounds from algae [7] and tunicates [8]. Nowadays, there are four marine natural product-derived drugs approved for marketing: cytarabine and vidarabine, nucleosides with anticancer and antiviral properties, respectively; ziconotide, a peptide with potent analgesic activity; and trabectedin, a tetrahydroisoquinoline alkaloid approved for the treatment of soft tissue sarcoma and ovarian carcinoma [9].…”

Section: Introductionmentioning

confidence: 99%

Spasmolytic Effect of Caulerpine Involves Blockade of Ca2+ Influx on Guinea Pig Ileum

et al. 2013

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In this work, we investigated the spasmolytic effect of caulerpine, a bisindole alkaloid isolated from marine algae of the Caulerpa genus, on guinea pig ileum. Our findings indicated that caulerpine inhibited phasic contractions induced by carbachol (IC50 = 7.0 ± 1.9 × 10−5 M), histamine (IC50 = 1.3 ± 0.3 × 10−4 M) and serotonin (IC50 = 8.0 ± 1.4 × 10−5 M) in a non-selective manner. Furthermore, caulerpine concentration-dependently inhibited serotonin-induced cumulative contractions (pD′2 = 4.48 ± 0.08), shifting the curves to the right with Emax reduction and slope of 2.44 ± 0.21, suggesting a noncompetitive antagonism pseudo-irreversible. The alkaloid also relaxed the ileum pre-contracted by KCl (EC50 = 9.0 ± 0.9 × 10−5 M) and carbachol (EC50 = 4.6 ± 0.7 × 10−5 M) in a concentration-dependent manner. This effect was probably due to inhibition of Ca2+ influx through voltage-gated calcium channels (CaV), since caulerpine slightly inhibited the CaCl2-induced contractions in depolarizing medium without Ca2+, shifting the curves to the right and with Emax reduction. According to these results, the spasmolytic effect of caulerpine on guinea pig ileum seems to involve inhibition of Ca2+ influx through CaV. However, other mechanisms are not discarded.

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Section: Introductionmentioning

confidence: 99%

Spasmolytic Effect of Caulerpine Involves Blockade of Ca2+ Influx on Guinea Pig Ileum

et al. 2013

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“…However, this is yet to be adequately tested. Of further note, several DMT derivatives have potent antimicrobial activity 14 and thus may also contribute to the inhibitory activity reported in our study. Further studies are required to test these compounds for growth inhibitory activity against the bacterial pathogens screened in our study.…”

Section: Discussionmentioning

confidence: 94%

Swainsona Formosa (G.Don) Joy Thomp. Solvent Extractions Inhibit the Growth of a Panel of Pathogenic Bacteria

Chikowe¹,

Mpala²,

Cock³

2017

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Introduction: Swainsona formosa is a legumous plant which is endemic to the arid inland regions of Australia. Several Swainsona spp. were valued by the first Australian for their antiseptic properties and were used traditionally to treat a variety of bacterial diseases. Despite this, S. formosa solvent extractions have not been rigorously examined for antibacterial properties against many bacterial pathogens. Methods: The antimicrobial activity of S. formosa leaf extracts was investigated by disc diffusion and growth time course assays against a panel of pathogenic bacteria. The growth inhibitory activity was quantified by MIC determination. Toxicity was determined using the Artemia franciscana nauplii bioassay. Results: S. formosa leaf extracts inhibited the growth of a wide range of gram positive and gram negative bacteria. The methanolic extracts were generally more potent than the aqueous extracts. The methanolic and aqueous S. formosa leaf extracts were particularly potent inhibitors of A. faecalis, A. hydrophilia, K. pneumoniae, P. mirabilis, B. cereus, S. aureus and S. pyogenes growth, with MIC values substantially <1000 µg/mL and as low as 150 µg/mL against some bacteria (methanolic extract against P. mirabilis). The antibacterial activity of the methanolic and aqueous S. formosa leaf extracts was further investigated by growth time course assays which showed significant growth inhibition in cultures of all bacterial species within 1 h of exposure. All extracts were determined to be nontoxic in the Artemia franciscana nauplii bioassay, indicating their safety for therapeutic uses. Conclusions: The lack of toxicity of the S. formosa leaf extracts and their growth inhibitory bioactivity against a panel of pathogenic bacteria indicate their potential in the development of antiseptic agents.

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“…The metabolites responsible for these biological activities were among the earliest marine natural products described, and they came from Aplysina species collected in the Mediterranean (Fattorusso et al, 1972) and the eastern Pacific (Andersen and Faulkner, 1973) in the quest for new drugs from the sea. Since then, over 100 halogenated tyrosine alkaloids have been described from Aplysina species worldwide (Lira et al, 2011), with considerable speculation about their importance in ecological interactions and use in human applications (Niemann et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Metabolite variability in Caribbean sponges of the genus Aplysina

Puyana

Pawlik

Blum

et al. 2015

Revista Brasileira de Farmacognosia

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BJP 168 1-8 Revista Brasileira de Farmacognosia xxx (2015) xxx-xxx w w w . s b f g n o s i a . o r g . b r / r e v i s t a Original Article a b s t r a c tSponges of the genus Aplysina are among the most common benthic animals on reefs of the Caribbean, and display a wide diversity of morphologies and colors. Tissues of these sponges lack mineralized skeletal elements, but contain a dense spongin skeleton and an elaborate series of tyrosine-derived brominated alkaloid metabolites that function as chemical defenses against predatory fishes, but do not deter some molluscs. Among the earliest marine natural products to be isolated and identified, these metabolites remain the subject of intense interest for commercial applications because of their activities in various bioassays. In this study, crude organic extracts from 253 sponges from ten morphotypes among the species Aplysina archeri, Aplysina bathyphila, Aplysina cauliformis, Aplysina fistularis, Aplysina fulva, A. insularis, and Aplysina lacunosa were analyzed by liquid chromatography-mass spectrometry (LC-MS) to characterize the pattern of intra-and interspecific variabilities of the twelve major secondary metabolites present therein. Patterns across Aplysina species ranged from the presence of mostly a single compound, fistularin-3, in A. cauliformis, to a mixture of metabolites present in the other species. These patterns did not support the biotransformation hypothesis for conversion of large molecular weight molecules to smaller ones for the purpose of enhanced defense. Discriminant analyses of the metabolite data revealed strong taxonomic patterns that support a close relationship between A. fistularis, A. fulva and A. insularis, while two morphotypes of A. cauliformis (lilac creeping vs. brown erect) were very distinct. Two morphotypes of A. lacunosa, one with hard tissue consistency, the other soft and thought to belong to a separate genus (Suberea), had very similar chemical profiles. Of the 12 metabolites found among samples, variation in fistularin-3, dideoxyfistularin-3 and hydroxyaerothionin provided the most predictive influence in decreasing order. Except for one morphotype, weak relationships were found from within-morphotype analyses of metabolite concentrations as a function of geographic location (Florida, N Bahamas, S Bahamas) and depth (<10 m, 10-20 m, >20 m). Our data suggest that metabolite profiles are strongly influenced by sponge phenotype rather than by the diverse microbiome which many Aplysina species share.

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Brominated Compounds from Marine Sponges of the Genus Aplysina and a Compilation of Their 13C NMR Spectral Data

Cited by 50 publications

References 132 publications

Spasmolytic Effect of Caulerpine Involves Blockade of Ca2+ Influx on Guinea Pig Ileum

Spasmolytic Effect of Caulerpine Involves Blockade of Ca2+ Influx on Guinea Pig Ileum

Swainsona Formosa (G.Don) Joy Thomp. Solvent Extractions Inhibit the Growth of a Panel of Pathogenic Bacteria

Metabolite variability in Caribbean sponges of the genus Aplysina

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