Calbistrin B
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| Category | Antibiotics |
| Catalog number | BBF-00200 |
| CAS | 147384-56-3 |
| Molecular Weight | 540.64 |
| Molecular Formula | C31H40O8 |
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Description
Calbistrin B is an antifungal antibiotic produced by Penicillum restrictum and has anti-candida effects.
Specification
| IUPAC Name | (2E,4Z,6E,8E)-12-[[(3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,8,9,10,10a-hexahydrobenzo[f]chromen-10-yl]oxy]-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid |
| Canonical SMILES | CC1CC(C2C(=C1)C=CC3(C2(C(=O)CC(O3)O)C)C)OC(=O)C(C)C(C(=CC=CC(=CC=CC(=O)O)C)C)O |
| InChI | InChI=1S/C31H40O8/c1-18(10-8-12-25(33)34)9-7-11-20(3)28(36)21(4)29(37)38-23-16-19(2)15-22-13-14-30(5)31(6,27(22)23)24(32)17-26(35)39-30/h7-15,19,21,23,26-28,35-36H,16-17H2,1-6H3,(H,33,34)/b9-7+,12-8+,18-10-,20-11+/t19-,21?,23+,26-,27-,28?,30-,31-/m1/s1 |
| InChI Key | YKPRQPBIYQBKND-YEFXOKEYSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 750.8°C at 760 mmHg |
| Density | 1.23 g/cm3 |
Reference Reading
1. A Penicillium rubens platform strain for secondary metabolite production
Carsten Pohl, Fabiola Polli, Tabea Schütze, Annarita Viggiano, László Mózsik, Sascha Jung, Maaike de Vries, Roel A L Bovenberg, Vera Meyer, Arnold J M Driessen Sci Rep. 2020 May 6;10(1):7630. doi: 10.1038/s41598-020-64893-6.
We present a Penicillium rubens strain with an industrial background in which the four highly expressed biosynthetic gene clusters (BGC) required to produce penicillin, roquefortine, chrysogine and fungisporin were removed. This resulted in a minimal secondary metabolite background. Amino acid pools under steady-state growth conditions showed reduced levels of methionine and increased intracellular aromatic amino acids. Expression profiling of remaining BGC core genes and untargeted mass spectrometry did not identify products from uncharacterized BGCs. This platform strain was repurposed for expression of the recently identified polyketide calbistrin gene cluster and achieved high yields of decumbenone A, B and C. The penicillin BGC could be restored through in vivo assembly with eight DNA segments with short overlaps. Our study paves the way for fast combinatorial assembly and expression of biosynthetic pathways in a fungal strain with low endogenous secondary metabolite burden.
2. A metabolomic study of vegetative incompatibility in Cryphonectria parasitica
Thomas E Witte, Sam Shields, Graham W Heberlig, Mike G Darnowski, Anatoly Belov, Amanda Sproule, Christopher N Boddy, David P Overy, Myron L Smith Fungal Genet Biol. 2021 Dec;157:103633. doi: 10.1016/j.fgb.2021.103633. Epub 2021 Oct 5.
Vegetative incompatibility (VI) is a form of non-self allorecognition in filamentous fungi that restricts conspecific hyphal fusion and the formation of heterokaryons. In the chestnut pathogenic fungus, Cryphonectria parasitica, VI is controlled by six vic loci and has been of particular interest because it impedes the spread of hypoviruses and thus biocontrol strategies. We use nuclear magnetic resonance and high-resolution mass spectrometry to characterize alterations in the metabolome of C. parasitica over an eight-day time course of vic3 incompatibility. Our findings support transcriptomic data that indicated remodeling of secondary metabolite profiles occurs during vic3 -associated VI. VI-associated secondary metabolites include novel forms of calbistrin, decumbenone B, a sulfoxygenated farnesyl S-cysteine analog, lysophosphatidylcholines, and an as-yet unidentified group of lipid disaccharides. The farnesyl S-cysteine analog is structurally similar to pheromones predicted to be produced during VI and is here named 'crypheromonin'. Mass features associated with C. parasitica secondary metabolites skyrin, rugulosin and cryphonectric acid were also detected but were not VI specific. Partitioning of VI-associated secondary metabolites was observed, with crypheromonins and most calbistrins accumulating in the growth medium over time, whereas lysophosphatidylcholines, lipid disaccharide-associated mass features and other calbistrin-associated mass features peaked at distinct time points in the mycelium. Secondary metabolite biosynthetic gene clusters and potential biological roles associated with the detected secondary metabolites are discussed.
3. Identification of the decumbenone biosynthetic gene cluster in Penicillium decumbens and the importance for production of calbistrin
Sietske Grijseels, Carsten Pohl, Jens Christian Nielsen, Zahida Wasil, Yvonne Nygård, Jens Nielsen, Jens C Frisvad, Kristian Fog Nielsen, Mhairi Workman, Thomas Ostenfeld Larsen, Arnold J M Driessen, Rasmus John Normand Frandsen Fungal Biol Biotechnol. 2018 Dec 19;5:18. doi: 10.1186/s40694-018-0063-4. eCollection 2018.
Background: Filamentous fungi are important producers of secondary metabolites, low molecular weight molecules that often have bioactive properties. Calbistrin A is a secondary metabolite with an interesting structure that was recently found to have bioactivity against leukemia cells. It consists of two polyketides linked by an ester bond: a bicyclic decalin containing polyketide with structural similarities to lovastatin, and a linear 12 carbon dioic acid structure. Calbistrin A is known to be produced by several uniseriate black Aspergilli, Aspergillus versicolor-related species, and Penicillia. Penicillium decumbens produces calbistrin A and B as well as several putative intermediates of the calbistrin pathway, such as decumbenone A-B and versiol. Results: A comparative genomics study focused on the polyketide synthase (PKS) sets found in three full genome sequence calbistrin producing fungal species, P. decumbens, A. aculeatus and A. versicolor, resulted in the identification of a novel, putative 13-membered calbistrin producing gene cluster (calA to calM). Implementation of the CRISPR/Cas9 technology in P. decumbens allowed the targeted deletion of genes encoding a polyketide synthase (calA), a major facilitator pump (calB) and a binuclear zinc cluster transcription factor (calC). Detailed metabolic profiling, using UHPLC-MS, of the ∆calA (PKS) and ∆calC (TF) strains confirmed the suspected involvement in calbistrin productions as neither strains produced calbistrin nor any of the putative intermediates in the pathway. Similarly analysis of the excreted metabolites in the ∆calB (MFC-pump) strain showed that the encoded pump was required for efficient export of calbistrin A and B. Conclusion: Here we report the discovery of a gene cluster (calA-M) involved in the biosynthesis of the polyketide calbistrin in P. decumbens. Targeted gene deletions proved the involvement of CalA (polyketide synthase) in the biosynthesis of calbistrin, CalB (major facilitator pump) for the export of calbistrin A and B and CalC for the transcriptional regulation of the cal-cluster. This study lays the foundation for further characterization of the calbistrin biosynthetic pathway in multiple species and the development of an efficient calbistrin producing cell factory.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
