Cytotoxic Bastadin 24 from the Australian Sponge <i>Ianthella quadrangulata</i>

Greve, Hendrik; Kehraus, Stefan; Krick, Anja; Kelter, Gerhard; Maier, Armin; Fiebig, Heinz‐Herbert; Wright, Anthony D.; König, Gabriele M.

doi:10.1021/np070373e

Cited by 29 publications

(33 citation statements)

References 12 publications

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“…203 This compound is part of a larger family of metabolites that consists of more than 26 members, 204 which have been reported to display a range of biological activities. 205–208 Bastadin 9 inhibited BACE1 cleavage of APP with IC 50 values of 0.3 and 2.8 μM in enzyme- and cell-based assays, respectively. Although other analogs inhibited BACE1 as well, they were less potent.…”

Section: Protease Inhibitors (Amyloid Cascade Hypothesis)mentioning

confidence: 99%

Natural products as a source of Alzheimer's drug leads

2011

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Section: Protease Inhibitors (Amyloid Cascade Hypothesis)mentioning

confidence: 99%

Natural products as a source of Alzheimer's drug leads

2011

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“…768, which was identified as Curvularia sp. [8] In the current study, we were able to isolate and identify the novel fungal macrolide 1 , which is characterised by a 14-membered macrolide like the RALs (e.g., zearalenone and radicicol) on the one hand, but resembles the phenylacetic acid lactone moiety of the curvularins on the other hand. Such nonaketide based carbon skeletons as for curvularins found in 1 have so far exclusively appeared in a Japanese patent as lead structure concerning the inhibition of neuropeptide Y receptor for anti-obesity programs.…”

Section: Introductionmentioning

confidence: 99%

Apralactone A and a New Stereochemical Class of Curvularins from the Marine Fungus Curvularia sp.

et al. 2008

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Chemical investigations of the cytotoxic extract of the marine-derived fungus Curvularia sp. (strain no. 768), isolated from the red alga Acanthophora spicifera, yielded the novel macrolide apralactone A (1), as well as the antipodes of curvularin macrolides 2–7. Compound 8, a dimeric curvularin was recognised as an artefact. The structures of 1–8 were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, CD, MS, UV and IR). Apralactone A (1) is a 14-membered phenyl acetic acid macrolactone, and the first such compound with a 4-chromanone substructure. Compounds 1, 2, 4, 5 and 6 were found to be cytotoxic towards human tumor cell lines with mean IC50 values in the range of 1.25 to 30.06 µM.

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“…Ianthella basta contains brominated macrocyclic alkaloids, so-called bastadins. Bastadins represent a unique class of natural products based on tyrosine-derived dipeptides (Kazlauskas et al, 1980, 1981; Pordesimo and Schmitz, 1990; Greve et al, 2008) with interesting medicinal properties (Franklin et al, 1996; Aoki et al, 2006; Kotoku et al, 2008). For example, they are cytotoxic against cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Chitin-based scaffolds are an integral part of the skeleton of the marine demosponge Ianthella basta

Brunner

Ehrlich

Schupp

et al. 2009

Journal of Structural Biology

161

136

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The skeletons of demosponges, such as Ianthella basta, are known to be a composite material containing organic constituents. Here, we show that a filigree chitin-based scaffold is an integral component of the I. basta skeleton. These chitin-based scaffolds can be isolated from the sponge skeletons using an isolation and purification technique based on treatment with alkaline solutions. Solid-state 13 C NMR, Raman, and FT-IR spectroscopies, as well as chitinase digestion, reveal that the isolated material indeed consists of chitin. The morphology of the scaffolds has been determined by light and electron microscopy. It consists of cross-linked chitin fibers approximately 40-100 nm in diameter forming a micro-structured network. The overall shape of this network closely resembles the shape of the integer sponge skeleton. Solid-state 13 C NMR spectroscopy was used to characterize the sponge skeleton on a molecular level. The 13 C NMR signals of the chitin-based scaffolds are relatively broad, indicating a high amount of disordered chitin, possibly in the form of surfaceexposed molecules. X-ray diffraction confirms that the scaffolds isolated from I. basta consist of partially disordered and loosely packed chitin with large surfaces. The spectroscopic signature of these chitin-based scaffolds is closer to that of α-chitin than β-chitin.

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Cytotoxic Bastadin 24 from the Australian Sponge Ianthella quadrangulata

Cited by 29 publications

References 12 publications

Natural products as a source of Alzheimer's drug leads

Natural products as a source of Alzheimer's drug leads

Apralactone A and a New Stereochemical Class of Curvularins from the Marine Fungus Curvularia sp.

Chitin-based scaffolds are an integral part of the skeleton of the marine demosponge Ianthella basta

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