New bromotyrosine alkaloids from the marine sponge Psammaplysilla purpurea

Tilvi, Supriya; Rodrigues, Celina; Naik, C.G.; Parameswaran, P.S.; Wahidhulla, Solimabi

doi:10.1016/j.tet.2004.09.009

Cited by 61 publications

(59 citation statements)

References 19 publications

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“…Many of these compounds were reported to possess cytotoxicity, 17 anti-inflamatory 18,19 and anti-microbial activities. 20 As a part of our effort to the discovery of bioactive metabolites from marine organisms, 21 here, we wish to report the isolation of two norcembranoid diterpenes (1 and 2) that are epimer at one carbon atom (C-9) from the soft coral of the genus sinularia. Bioassay of the compounds against some microorganisms or clincal isolates viz.…”

Section: Introductionmentioning

confidence: 99%

Structural studies and antimicrobial properties of norcembrane diterpenoid from an Indian soft coral Sinularia inelegans Tixier-Durivault

2009

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Two metabolites featuring norcembranoid diterpene skeleton have been isolated from chloroform extract of soft coral of the genus sinularia, which was collected from the southern coast of India. The structures of the metabolites were determined by 1D, 2D NMR spectroscopic data and HRESIMS data analysis. The compounds have shown moderate-to-high antimicrobial activities. The structure and the relative stereochemistry of the metabolite 1 have been determined by X-ray crystallography.

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Section: Introductionmentioning

confidence: 99%

Structural studies and antimicrobial properties of norcembrane diterpenoid from an Indian soft coral Sinularia inelegans Tixier-Durivault

2009

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“…1,2 In particular, sponges of the order Verongida have been the source of a variety of biologically active dibromotyrosine-derived modified peptides and alkaloids. Recent examples of compounds belonging to this structural class are the purpurealidins A -D, F -H isolated from the sponge Psammaplysilla purpurea, 3 trisulfide psammalin A, (E,E)-bromopsammalin A and bispsammalin A from the association of the sponges Jaspis wondoensis and Poecillastra wondoensis, 4 purpuroceratic acids A and B from Pseudoceratina purpurea, 5 several new and known psammalins active as histone deacetylase and DNA methyltransferase inhibitors, from the sponge Psammaplysilla purpurea, 6 the moderately cytotoxic purealidin S and purpuramine J isolated from the sponge Druinella sp., 7 and nakirodin A from an unidentified Verongida sponge. 8 We have recently reported the isolation of two new members of the dibromotyrosine derivatives, caissarines A (1) and B (2), from the sponge Aplysina caissara.…”

Section: Introductionmentioning

confidence: 99%

Further dibromotyrosine-derived metabolites from the marine sponge Aplysina caissara

Lira¹,

Berlinck²,

Nascimento³

et al. 2006

J. Braz. Chem. Soc.

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A re-investigação química do extrato bruto da esponja Aplysina caissara levou ao isolamento de cinco novos derivados da dibromotirosina, denominados agelocaissarinas A1, A2, B1, B2 e caissarina C, além dos já conhecidos fistularina-3 e 11-hidroxiaerotionina. Os compostos isolados tiveram suas estruturas determinadas pela análise de seus espectros de RMN mono-e bidimensionais, espectro de massas de alta resolução, infravermelho e ultravioleta. A configuração relativa das agelocaissarinas pôde ser estabelecida por análise dos espectros de RMN-1 H e modelagem molecular, enquanto que a configuração absoluta do sistema espiroxazolidínico da fistularina-3, da caissarina C e da 11-hidroxiaerotionina pôde ser estabelecida pela análise de seus espectros de dicroísmo circular. A fistularina-3 e a 11-hidroxiaerotionina apresentaram atividade antibiótica moderada contra várias linhagens de bactérias patogênicas.The re-investigation of the crude extract obtained from the sponge Aplysina caissara led to the isolation of five new dibromotyrosine derivatives, named agelocaissarines A1, A2, B1, B2 and caissarine C, along with the already known fistularin-3 and 11-hydroxyaerothionin. All compounds were identified by analysis of mono-and bidimensional NMR spectra, high resolution mass spectra, infrared and ultraviolet spectra. The relative stereochemistry of agelocaissarines could be established by analysis of 1 H NMR spectra and molecular modeling, while the absolute configuration of the spiroxazolidine moieties of fistularin-3, caissarine C and 11-hydroxyaerothionin was established by analysis of 1 H NMR and circular dichroism spectra. Fistularin-3 and 11-hydroxyaerothionin displayed moderate antibiotic activity against several pathogenic bacteria.

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“…[6][7][8][9] More recently it was found that spiroisoxazoline containing SJ755 shows a remarkable integrin antagonist behavior, showing a new application Some stereoselective synthesis of unnatural spiroisoxazolinoheterocycle-based derivatives in which exomethylene heterocyclic compounds react as a dipolarophile with nitrile oxides is also reported. [11][12][13][14][15] We have found a strong evidence for a predictive anti-diastereoselective 1,3-dipolar cycloadditions of nitrile oxides and nitrones to the substituted heterocyclic compounds possessing an exocyclic double bond.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of chiral NiII complex of Schiff base of (S)-2-N-(N-benzylprolyl)aminobenzophenone and 5-amino-4,5-dihydro-3-(2,4,6-trimethylphenyl)isoxazol-5-carboxylic acid

Micuch¹,

Fišera²,

Kožı́šek³

et al. 2006

Arkivoc

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The chiral Ni II complex of Schiff base of (S)-2-N-(N-benzylprolyl)aminobenzophenone and 5-amino-4,5-dihydro-3-(2,4,6-trimethylphenyl)isoxazol-5-carboxylic acid (6) was prepared via the cycloaddition of chiral complex of Ni 5 with mesitonitrile oxide 1. The cycloaddition proceeded with complete regioselectivity to provide 5-substituted isoxazolines 6 and 7. The approach of the dipole takes place predominantly from the less sterically hindered side of dipolarophile 5, the diastereoisomers were formed in 96:4 ratio. The detailed structure of 6 was established by X-ray analysis.

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New bromotyrosine alkaloids from the marine sponge Psammaplysilla purpurea

Cited by 61 publications

References 19 publications

Structural studies and antimicrobial properties of norcembrane diterpenoid from an Indian soft coral Sinularia inelegans Tixier-Durivault

Structural studies and antimicrobial properties of norcembrane diterpenoid from an Indian soft coral Sinularia inelegans Tixier-Durivault

Further dibromotyrosine-derived metabolites from the marine sponge Aplysina caissara

The synthesis of chiral NiII complex of Schiff base of (S)-2-N-(N-benzylprolyl)aminobenzophenone and 5-amino-4,5-dihydro-3-(2,4,6-trimethylphenyl)isoxazol-5-carboxylic acid

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