Structure Elucidation and Anticancer Activity of 7-Oxostaurosporine Derivatives from the Brazilian Endemic Tunicate Eudistoma vannamei

Jimenez, Paula Christine; Wilke, Diego Veras; Ferreira, Elthon G.; Takeara, Renata; Moraes, Manoel Odoríco de; Silveira, Edilberto R.; Lotufo, Tito Monteiro da Cruz; Lopes, Norberto Peporine; Costa-Lotufo, Letı́cia V.

doi:10.3390/md10051092

Cited by 38 publications

(22 citation statements)

References 33 publications

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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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“…The mixture of 236 and 237 displayed cytotoxic activity across a panel of tumor cell lines with IC 50 values in the range of 10.3-144.47 nM and was 14 times more cytotoxic than staurosporine (238). 96 The occurrence of such alkaloids in E. vannamei may be correlated to the presence of associated biota, such as Streptomyces bacteria. In the light of to this hypothesis, marine microorganisms associated with E. vannamei were recovered and cultured.…”

Section: Ascidiansmentioning

confidence: 99%

Natural Products from Marine Invertebrates and Microorganisms in Brazil between 2004 and 2017: Still the Challenges, More Rewards

Ióca¹,

Nicácio²,

Berlinck³

2018

J. Braz. Chem. Soc.

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The Brazilian marine biodiversity represents a unique, yet underexplored resource of biologically active compounds. This review provides an analysis of the development of marine natural products chemistry in Brazil within the period comprised between 2004 and 2017. Emphasis is directed towards marine invertebrate and marine microorganisms metabolites, including isolation, structure analysis, biosynthesis, bioactivities and total synthesis. An overview of the research on marine natural products by Brazilian researchers is also discussed, as well as perspectives for the development of the chemistry of marine natural products in Brazil.

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“…This region is characterized by a high degree of endemism over different taxonomical groups [8,9]. Its biotechnological potential is robust and has been noted in a series of recent studies [10,11,12,13,14,15]. As part of a program to expand natural product science in Brazil, we were interested in further exploring Zoanthidea, as a potential source for new structural classes.…”

Section: Introductionmentioning

confidence: 99%

Palyosulfonoceramides A and B: Unique Sulfonylated Ceramides from the Brazilian Zoanthids Palythoa caribaeorum and Protopalyhtoa variabilis

et al. 2012

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The zoanthids Palythoa caribaeorum and Protopalythoa variabilis are among the most abundant marine species along the Brazilian coast. We now report the isolation and structure elucidation of two unprecedented sulfonylated ceramides, palyosulfonoceramide A (1) and palyosulfonoceramide B (2) from specimens collected off Brazil’s northeastern coast. The structures of 1 and 2 were established using a combination of NMR analyses, including: evaluation of 1H, 13C, 1H–1H COSY, 1H–13C HSQC, 1H–13C HMBC, and 1H–15N HMBC NMR spectra, high-resolution mass spectrometry and chemical degradation. In addition, we also isolated the corresponding known ceramides, N-((2S,3R,4E,8E)-1,3-dihydroxyoctadeca-4,8-dien-2-yl)-hexadecanamide (3) and N-((2S,3R,4E)-1,3-dihydroxyoctadeca-4-en-2-yl)-hexadecanamide (4), which provided further support for the assignments of 1 and 2.

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Structure Elucidation and Anticancer Activity of 7-Oxostaurosporine Derivatives from the Brazilian Endemic Tunicate Eudistoma vannamei

Cited by 38 publications

References 33 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

Natural Products from Marine Invertebrates and Microorganisms in Brazil between 2004 and 2017: Still the Challenges, More Rewards

Palyosulfonoceramides A and B: Unique Sulfonylated Ceramides from the Brazilian Zoanthids Palythoa caribaeorum and Protopalyhtoa variabilis

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