Calcaripeptides A–C, Cyclodepsipeptides from a <i>Calcarisporium</i> Strain

Silber, Johanna; Ohlendorf, Birgit; Labes, Antje; Näther, Christian; Imhoff, Johannes F.

doi:10.1021/np400262t

Cited by 27 publications

(31 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Production of scopularide A in STRs demonstrates that marine fungal compounds can be suitable for scalable production, even with the native production organism, and similar strategies should be applied to enhance production of other recently discovered cyclic peptides which have only been produced in flask culture (e.g. [17-20]).…”

Section: Discussionmentioning

confidence: 99%

Production of scopularide A in submerged culture with Scopulariopsis brevicaulis

et al. 2014

Self Cite

View full text Add to dashboard Cite

BackgroundMarine organisms produce many novel compounds with useful biological activity, but are currently underexploited. Considerable research has been invested in the study of compounds from marine bacteria, and several groups have now recognised that marine fungi also produce an interesting range of compounds. During product discovery, these compounds are often produced only in non-agitated culture conditions, which are unfortunately not well suited for scaling up. A marine isolate of Scopulariopsis brevicaulis, strain LF580, produces the cyclodepsipeptide scopularide A, which has previously only been produced in non-agitated cultivation.ResultsScopulariopsis brevicaulis LF580 produced scopularide A when grown in batch and fed-batch submerged cultures. Scopularide A was extracted primarily from the biomass, with approximately 7% being extractable from the culture supernatant. By increasing the biomass density of the cultivations, we were able to increase the volumetric production of the cultures, but it was important to avoid nitrogen limitation. Specific production also increased with increasing biomass density, leading to improvements in volumetric production up to 29-fold, compared with previous, non-agitated cultivations. Cell densities up to 36 g L-1 were achieved in 1 to 10 L bioreactors. Production of scopularide A was optimised in complex medium, but was also possible in a completely defined medium.ConclusionsScopularide A production has been transferred from a non-agitated to a stirred tank bioreactor environment with an approximately 6-fold increase in specific and 29-fold increase in volumetric production. Production of scopularide A in stirred tank bioreactors demonstrates that marine fungal compounds can be suitable for scalable production, even with the native production organism.

show abstract

Section: Discussionmentioning

confidence: 99%

Production of scopularide A in submerged culture with Scopulariopsis brevicaulis

et al. 2014

Self Cite

View full text Add to dashboard Cite

show abstract

“…[23] The DhdaA strain produced three labdane-related diterpenoid compounds (9-11)a sc haracterized by NMR spectroscopy (Table S14, Figures S35-S44). [25] Thenew diterpene arbusculic acid A (11) is structurally related to 9 and 10,and most likely derives from cassadiene 15 (Scheme 2). [24] Both compounds are heavily oxidized derivatives of isocassadiene 14.…”

Section: Angewandte Chemiementioning

confidence: 99%

Epigenetic Genome Mining of an Endophytic Fungus Leads to the Pleiotropic Biosynthesis of Natural Products

Mao

et al. 2015

Angewandte Chemie

View full text Add to dashboard Cite

The small-molecule biosynthetic potential of most filamentous fungi has remained largely unexplored and represents an attractive source for the discovery of new compounds.G enome sequencing of Calcarisporium arbuscula, am ushroom-endophytic fungus,r evealed 68 core genes that are involved in natural product biosynthesis.T his is in sharp contrast to the predominant production of the ATPase inhibitors aurovertin Ba nd Di nt he wild-type fungus. Inactivation of ah istone H3 deacetylase led to pleiotropic activation and overexpression of more than 75 %o ft he biosynthetic genes.Sampling of the overproduced compounds led to the isolation of ten compounds of which four contained new structures,i ncluding the cyclic peptides arbumycin and arbumelin, the diterpenoid arbuscullic acid A, and the meroterpenoid arbuscullic acid B. Such epigenetic modifications therefore providearapid and global approach to mine the chemical diversity of endophytic fungi.

show abstract

“…that is a part of the marine fungal strain collection of the Kiel Center for Marine Natural Products [14]. Extracts of cultures from the Calcarisporium sp.…”

Section: Resultsmentioning

confidence: 99%

Calcarides A–E, Antibacterial Macrocyclic and Linear Polyesters from a Calcarisporium Strain

et al. 2013

Self Cite

View full text Add to dashboard Cite

Bioactive compounds were detected in crude extracts of the fungus, Calcarisporium sp. KF525, which was isolated from German Wadden Sea water samples. Purification of the metabolites from the extracts yielded the five known polyesters, 15G256α, α-2, β, β-2 and π (1–5), and five new derivatives thereof, named calcarides A–E (6–10). The chemical structures of the isolated compounds were elucidated on the basis of one- and two-dimensional NMR spectroscopy supported by UV and HRESIMS data. The compounds exhibited inhibitory activities against Staphylococcus epidermidis, Xanthomonas campestris and Propionibacterium acnes. As the antibacterial activities were highly specific with regard to compound and test strain, a tight structure-activity relationship is assumed.

show abstract

Calcaripeptides A–C, Cyclodepsipeptides from a Calcarisporium Strain

Cited by 27 publications

References 24 publications

Production of scopularide A in submerged culture with Scopulariopsis brevicaulis

Production of scopularide A in submerged culture with Scopulariopsis brevicaulis

Epigenetic Genome Mining of an Endophytic Fungus Leads to the Pleiotropic Biosynthesis of Natural Products

Calcarides A–E, Antibacterial Macrocyclic and Linear Polyesters from a Calcarisporium Strain

Contact Info

Product

Resources

About