Two new antibiotics from the red sea sponge Psammaplysilla purpurea

Rotem, Michal; Carmely, S.; Kashman, Yoel; Loya, Yossi

doi:10.1016/s0040-4020(01)91843-5

Cited by 47 publications

(50 citation statements)

References 10 publications

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“…8,9 We recently reported the isolation of psammaplysins K−W, together with 19-hydroxyplammaplysins E, P, Q, S, T, U, and W, from an extract of the Balinese sponge Aplysinella strongylata (order Verongida, family Aplysinellidae), with five of these new psammaplysins showing variation in the structural motif attached to C-16 of the aromatic ring, while the remaining compounds contained fatty acid side chains; 19-hydroxypsammaplysin E showed potent antimalarial activity. 11 The relative configuration of psammaplysin A (1) was first determined as (6S*,7S*) in 1985 by single-crystal X-ray crystallographic analysis of its diacetyl derivative (2). 3 Subsequent reports on the relative configuration of psammaplysins C−H were made by comparing their specific rotation values with those of psammaplysin A, 4,8,9,11,12 by chemical shift comparisons, [5][6][7]11 or by ROESY/NOESY correlation data.…”

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Absolute Configuration and Conformational Study of Psammaplysins A and B from the Balinese Marine SpongeAplysinella strongylata

et al. 2015

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The absolute configuration of psammaplysin A (1) has been assigned as (6R,7R) using experimental and calculated electronic circular dichroism (ECD) data and NMR analysis of MPA esters prepared from the acetamide derivative of 1. Detailed conformational analyses of a truncated model compound of 1 with an in vacuo method and with the PCM solvent model for MeOH have identified the major conformers and factors governing the ECD spectrum of 1. The correlation of the ECD data with the stereochemistry of 1 allows configurational assignment of related psammaplysin analogues on the basis of their ECD spectra.

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Absolute Configuration and Conformational Study of Psammaplysins A and B from the Balinese Marine SpongeAplysinella strongylata

et al. 2015

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“…The natural product 11-deoxyfistularin-3 11 contains two spirocyclic isoxazoline moieties and is cytotoxic toward estrogen dependent MCF-7 breast cancer cells (LD 50 =17 mg/L). Other closely related natural products such as psammaplysin A, 12 aerothionin, 13 homoaerothionin, 13 fistularin-3 14 and 11-ketofistularin-3 15 also have spirocyclic isoxazolines as well as physiological activities. However the therapeutic value associated with the paucity in natural occurrence of biologically active molecules have been a long term inspiration for designing, synthesizing and investigating the biological activity of new molecules for the discovery and development of novel pharmaceuticals.…”

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Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Das

Omollo

Sitole

et al. 2015

Tetrahedron Letters

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A series of structurally diverse 4-bromo spiro-isoxazolines possessing a variety of aromatic and aliphatic substituents at the 3 position, were synthesized through a 1,3-dipolar cycloaddition followed by intramolecular cyclization of a pendant hydroxyl or carboxylic acid group. The biochemical antiproliferative activity was evaluated in vitro by using two breast cancer cell lines (MCF-7 and MDA-MB-231) and two prostate cancer cell lines (PC-3 and DU-145) using the MTT viability assay, and the IC50 values were obtained. Spiro-isoxazoline derivatives bearing a p-chloro or an o-dichloro aromatic substituent at the 3-position of the isoxazoline showed considerable antitumor activities in all four cell lines with IC50 value ranging from 43μM to 56μM.

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“…2 Many of these metabolites show interesting antibiotic 3 and cytotoxic properties in cell lines. 4 Recently, particular interest has been given to the chemical analysis of these species because the presence of the bromotyrosine derivatives seems to be peculiar to the order and can be used as a chemical marker to support taxonomic work.…”

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confidence: 99%