Microsclerodermins F–I, Antitumor and Antifungal Cyclic Peptides from the Lithistid Sponge Microscleroderma sp.

Qureshi, Asfia; Colin, Patrick L.; Faulkner, D. John

doi:10.1016/s0040-4020(00)00286-6

Cited by 81 publications

(52 citation statements)

References 8 publications

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“…Biological studies showed that especially 1 showed good antifungal activity, which corresponds to the structurally related microsclerodermins. Yet we could find neither potent antitumor activity nor microtubule aberrations as has been described for some of the microsclerodermins [14,16]. First investigations into the mechanism of action showed that 1 seem to interfere with membrane integrity.…”

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confidence: 56%

Pedein A and B: Production, Isolation, Structure Elucidation and Biological Properties of New Antifungal Cyclopeptides from Chondromyces pediculatus (Myxobacteria)

et al. 2008

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Two new secondary metabolites, named pedein A and B, were isolated from the cell mass of the myxobacterium Chondromyces pediculatus. Their planar structures were elucidated by spectroscopic methods, in particular 2D NMR as 24-membered cyclic hexapeptides composed of a variable tryptophan residue, glycine, sarcosine and three unusual hydroxy b-and g-amino acids. The main component, pedein A, strongly inhibited the growth of yeasts and fungi, induced hemolysis of erythrocytes, and caused changes in membrane permeability of Rhodotorula glutinis. The structures of the pedeins are closely related to the large family of the microsclerodermins, which have been isolated from lithistid sponges of Microscleroderma and Theonella species. Keywords myxobacteria, pedeins, cyclic peptides, antifungal IntroductionMyxobacteria of the genus Chondromyces, suborder Sorangineae, have been shown to produce a variety of novel biologically active substances with different mechanisms of action. Thus, chondramides are inhibitors of the actin skeleton [1ϳ3], crocacin and ajudazols are mitochondrial electron transport inhibitors at different sites [4ϳ7], and apicularens are specific inhibitors of V-ATPase [8ϳ10]. Extracts of Chondromyces pediculatus, strain Cm p3 were noticed for their marked antifungal activity. HPLC/DAD/MS analysis of the extracts indicated the presence of six major components with molecular weights in the range of 781 to 924 mu of which two were correlated with the antifungal activity. The compounds responsible were isolated by column chromatography of the cell extract and named pedein A (1) and B (2). A tentative structure of 1 was depicted in the GBF Scientific Annual Report 1993 and at the international conference of microbial secondary metabolism in Interlaken 1994 [11] anticipating the structures of the related microsclerodermins [12ϳ14]. Here we describe in detail production, isolation, physicochemical properties and structure elucidation of 1 and 2 as well as biological properties of 1. Results Production and IsolationIn order to obtain smooth growth and reasonable cell densities, the producing organism had to be adapted to growth in liquid media by 4 to 8 transfers in shaken cultures. After that, the strain could be cultivated also in media based on technical substrates, e.g., Probion (single cell protein prepared from Methylomonas clarae; Hoechst AG, Frankfurt), soy flour, or oatmeal. effect of various technical substrates on the yields of 1 in 100-ml shake cultures of Chondromyces pediculatus strain Cm p3. By increasing the concentration of the technical substrates from 0.4 to 0.9% the amount of 1 usually decreased, with the exception of oatmeal, in which 1 production increased up to 11.9 mg/liter.The production of pedeins on a larger scale was performed in bioreactors containing media on the basis of different technical substrates. Yet comparable amounts of 1 as produced by cultivating strain Cm p3 in shake cultures, could not be achieved. In a 65-liter fermentation batch described in the experiment...

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confidence: 56%

Pedein A and B: Production, Isolation, Structure Elucidation and Biological Properties of New Antifungal Cyclopeptides from Chondromyces pediculatus (Myxobacteria)

et al. 2008

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“…Microscleroderma sp. from Palau gave 4 new cyclic peptides, Microsclerodermins F–I (7–10) , all of which inhibited the growth of C. albicans with MIC value of 1.5, 3, 12, and 25 μg per disk, respectively, and also showed cytotoxicity against the HCT-116 cell line with IC 50 value of 1.8, 2.4, 1.0, and 1.1 μg/mL, respectively (Qureshi et al, 2000). …”

Section: Anticancer Nrps From Marine Sponges and Tunicates (Figures 1–6)mentioning

confidence: 99%

The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates

2016

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Marine biodiversity is recognized by a wide and unique array of fascinating structures. The complex associations of marine microorganisms, especially with sponges, bryozoans, and tunicates, make it extremely difficult to define the biosynthetic source of marine natural products or to deduce their ecological significance. Marine sponges and tunicates are important source of novel compounds for drug discovery and development. Majority of these compounds are nitrogen containing and belong to non-ribosomal peptide (NRPs) or mixed polyketide–NRP natural products. Several of these peptides are currently under trial for developing new drugs against various disease areas, including inflammatory, cancer, neurodegenerative disorders, and infectious disease. This review features pharmacologically active NRPs from marine sponge and tunicates based on their biological activities.

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“…by Faulkner and coworkers. 59 These compounds contain several nonproteinogenic amino acids including Z-DTrp, g-amino-b-hydroxybutyric acid (GABOB), 3-amino-6-methyl-12-phenyl-2,4,5-trihydroxydodeca-7,9,11-trienoic acid (AMPTD), and a pyrrolidone-containing residue. Both 27a and 27b possess antifungal and antitumor properties.…”

Section: Trisubstituted Ab-dehydroamino Acidsmentioning

confidence: 99%

Bulky α,β-dehydroamino acids: their occurrence in nature, synthesis, and applications

Jiang

Castle

2015

Tetrahedron

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Microsclerodermins F–I, Antitumor and Antifungal Cyclic Peptides from the Lithistid Sponge Microscleroderma sp.

Cited by 81 publications

References 8 publications

Pedein A and B: Production, Isolation, Structure Elucidation and Biological Properties of New Antifungal Cyclopeptides from Chondromyces pediculatus (Myxobacteria)

Pedein A and B: Production, Isolation, Structure Elucidation and Biological Properties of New Antifungal Cyclopeptides from Chondromyces pediculatus (Myxobacteria)

The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates

Bulky α,β-dehydroamino acids: their occurrence in nature, synthesis, and applications

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