Ptilocaulin and isoptilocaulin, antimicrobial and cytotoxic cyclic guanidines from the Caribbean sponge Ptilocaulis aff. P. spiculifer (Lamarck, 1814)

Harbour, Gary C.; Tymiak, Adrienne A.; Rinehart, Kenneth L.; Shaw, Paul D.; Hughes, Robert G.; Mizsak, S. A.; Coats, J. H.; Zurenko, Gary E.; Li, Li H.; Kuentzel, Sandra L.

doi:10.1021/ja00408a071

Cited by 79 publications

(49 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…These spectral characteristics showed similarities with those of the ptilocaulin alkaloids. [2][3][4][5] Examination of the 1 H and 13 C NMR results and comparison with published data revealed a data set assigned to the known compound 1,8a;8b,3a-didehydro-8β-hydroxyptilocaulin. 5 Another set of 1 H and 13 C NMR data were assigned as in Table 1 by analysis of 1 H NMR, 13 C NMR, DEPT, and HMQC spectra, and by comparison with compound 1.…”

Section: Resultsmentioning

confidence: 99%

“…1 Members of this class include the series called ptilocaulins, [2][3][4][5] crambescins (crambines), [6][7][8][9] ptilomycalin A, crambescidins, [9][10][11][12][13][14][15] and batzelladines. [15][16][17] They were isolated separately from marine sponges belonging to the genera Batzella, Monanchora, Arenochalina, and Crambe (Order Poecilosclerida) and Ptilocaulis (Order Axinellida) and starfish Fromia monilis, and Celerina heffernani.…”

Section: Introductionmentioning

confidence: 99%

“…[15][16][17] They were isolated separately from marine sponges belonging to the genera Batzella, Monanchora, Arenochalina, and Crambe (Order Poecilosclerida) and Ptilocaulis (Order Axinellida) and starfish Fromia monilis, and Celerina heffernani. 18 These metabolites display diverse biological activities including cytotoxicity against P388, L1210, HCT-16, KB cell lines, 2,[10][11][12]14 antifungal activity against Candida albicans, 10 antiviral activity against Herpes simplex virus type 1 (HSV-1), and Hepatitis-B virus [10][11][12][13] and potent calcium channel antagonist activity. 14 Batzelladine A and B were reported to inhibit the binding of HIV-gp 120 to the CD4 cell-surface receptor protein 16 and crambescidins 826, 800, and fromiamycalin inhibited HIV-envelope-mediated fusion and as a result are potential inhibitors of HIV.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Crystallographic and NMR Studies of Antiinfective Tricyclic Guanidine Alkaloids from the Sponge Monanchora unguifera

et al. 2005

View full text Add to dashboard Cite

Three tricyclic guanidine alkaloids, including 1,8a;8b,3a-didehydro-8β-hydroxyptilocaulin (1), 1,8a;8b,3a-didehydro-8α-hydroxyptilocaulin (2) and mirabilin B (3), were identified from the marine sponge Monanchora unguifera. 1,8a;8b,3a-Didehydro-8α-hydroxyptilocaulin (2) is a new stereoisomer of 1, the structure of which was elucidated by spectroscopic analysis, comparison of its spectral data with those of 1, and confirmed by X-ray analysis. Compounds 1 and 2 cocrystallized in an unusual perfect order and packed around an approximate inversion center. A mixture of 1 and 2 is active against the malaria parasite Plasmodium falciparum with an IC 50 value of 3.8 μg/mL while mirabilin B (3) exhibited antifungal activity against Cryptococcus neoformans with an IC 50 value of 7.0 μg/mL and antiprotozoal activity against Leishmania donovani with an IC 50 value of 17 μg/mL.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Crystallographic and NMR Studies of Antiinfective Tricyclic Guanidine Alkaloids from the Sponge Monanchora unguifera

et al. 2005

View full text Add to dashboard Cite

show abstract

“…O sinal em δ 156,4 foi atribuído ao carbono da ligação dupla carbono-nitrogê-nio guanidínico e os dois sinais em δ 136,3 e 132,9 foram atribuí-dos a dois carbonos de uma ligação dupla carbono-carbono. A aná-lise conjunta dos espectros de RMN de 1 H (MeOH-d 4 , 500 MHz), de 13 C e bidimensionais (HMQC, HMBC e COSY), espectro de massas, bem como a comparação com dados da literatura 3,4 permitiram identificar a substância 1 como sendo a isoptilocaulina.…”

Section: Investigação Química Da Esponja Monanchora Arbusculaunclassified

Isolamento e atividades biológicas de produtos naturais das esponjas monanchora arbuscula, aplysina sp. petromica ciocalyptoides e topsentia ophiraphidites, da ascídia didemnum ligulum e do octocoral carijoa riisei

et al. 2007

View full text Add to dashboard Cite

Recebido em 13/7/06; aceito em 18/1/07; publicado na web em 24/7/07 ISOLATION AND BIOLOGICAL ACTIVITIES OF SECONDARY METABOLITES FROM THE SPONGES Monanchora aff. arbuscula, Aplysina sp. Petromica ciocalyptoides AND Topsentia ophiraphidites, FROM THE ASCIDIAN Didemnum ligulum AND FROM THE OCTOCORAL Carijoa riisei. The investigation of extracts from six species of marine invertebrates yielded one new and several known natural products. Isoptilocaulin from the sponge Monanchora aff. arbuscula displayed antimicrobial activity at 1.3 μg/mL against an oxacillin-resistant strain of Staphylococcus aureus. Five inactive known dibromotyrosine derivatives, 2 -6, were isolated from a new species of marine sponge, Aplysina sp. The sponges Petromica ciocalyptoides and Topsentia ophiraphidites yielded the known halistanol sulfate A (7) as an inhibitor of the antileishmanial target adenosine phosphoribosyl transferase. The ascidian Didemnum ligulum yielded asterubin (10) and the new N,N-dimethyl-O-methylethanolamine (11). The octocoral Carijoa riisei yielded the known 18-acetoxypregna-1,4,20-trien-3-one (12), which displayed cytotoxic activity against the cancer cell lines SF295, MDA-MB435, HCT8 and HL60.Keywords: marine sponge; ascidian; octocoral. INTRODUÇÃONos últimos anos, investigações químicas e farmacológicas de organismos marinhos têm contribuído significativamente para a descoberta de novas substâncias químicas potencialmente bioativas para fins terapêuticos 1 . Embora o litoral brasileiro seja o segundo mais extenso depois da Austrália, o desenvolvimento da química de produtos naturais de organismos marinhos no Brasil foi negligenciado por muitos anos, porque o principal foco da química de produtos naturais brasileira foi direcionado ao estudo de plantas. Desta maneira, a fauna marinha brasileira ainda é pouco explorada na pesquisa por produtos naturais biologicamente ativos, estruturalmente inéditos ou taxonomicamente relevantes 2 .No presente trabalho relata-se a investigação química dos extratos brutos bioativos de quatro esponjas, uma ascídia e um octocoral. Descreve-se o isolamento de um alcalóide guanidínico a partir da esponja Monanchora aff. arbuscula, de cinco derivados da dibromotirosina, a partir da esponja Aplysina sp., o isolamento do mesmo esterol trissulfatado a partir de ambas esponjas Petromica ciocalyptoides e Topsentia ophiraphidites, o primeiro isolamento da asterubina, a partir de uma ascídia, Didemnum ligulum, da qual também foi isolada a N-N-dimetil-O-metiletanoamina, inédito na literatura, além do 18-acetoxipregna-1,4,20-trien-3-ona a partir do octocoral Carijoa riisei. Também são apresentados os resultados de testes de atividade biológica realizados com estes metabólitos secundários.

show abstract

“…Adams HJ, Blair MR, Jr., Takman BH (1976 Ptilocaulin (Harbour et al 1981;Snider and Faith 1984 Abstract The great diversity of K + channels and their wide distribution in many tissues are associated with important functions in cardiac and neuronal excitability that are now better understood thanks to the discovery of animal toxins. During the past few decades, sea anemones have provided a variety of toxins acting on voltage-sensitive sodium and, more recently, potassium channels.…”

Section: Referencesmentioning

confidence: 99%

Developmental Biology of Neoplastic Growth

Macieira‐Coelho¹

2005

Progress in Molecular and Subcellular Biology

View full text Add to dashboard Cite

Ptilocaulin and isoptilocaulin, antimicrobial and cytotoxic cyclic guanidines from the Caribbean sponge Ptilocaulis aff. P. spiculifer (Lamarck, 1814)

Cited by 79 publications

References 0 publications

Crystallographic and NMR Studies of Antiinfective Tricyclic Guanidine Alkaloids from the Sponge Monanchora unguifera

Crystallographic and NMR Studies of Antiinfective Tricyclic Guanidine Alkaloids from the Sponge Monanchora unguifera

Isolamento e atividades biológicas de produtos naturais das esponjas monanchora arbuscula, aplysina sp. petromica ciocalyptoides e topsentia ophiraphidites, da ascídia didemnum ligulum e do octocoral carijoa riisei

Developmental Biology of Neoplastic Growth

Contact Info

Product

Resources

About