Calbistrin A
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| Category | Antibiotics |
| Catalog number | BBF-00199 |
| CAS | 147384-55-2 |
| Molecular Weight | 540.64 |
| Molecular Formula | C31H40O8 |
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Description
Calbistrin is an antifungal antibiotic produced by Penicillum restrictum and has anti-candida effects. Calbistrin A also has the effect of reducing cholesterol and promoting the production of nerve growth factor (NGF).
Specification
| IUPAC Name | (2E,4E,6E,8E)-12-[[(3R,4aS,8R,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+/m0/s1 |
| InChI Key | YKPRQPBIYQBKND-IXBFLDGTSA-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. One Polyketide Synthase, Two Distinct Products: Trans-Acting Enzyme-Controlled Product Divergence in Calbistrin Biosynthesis
Hui Tao, Takahiro Mori, Xingxing Wei, Yudai Matsuda, Ikuro Abe Angew Chem Int Ed Engl. 2021 Apr 12;60(16):8851-8858. doi: 10.1002/anie.202016525. Epub 2021 Mar 1.
Calbistrins are fungal polyketides consisting of the characteristic decalin and polyene moieties. Although the biosynthetic gene cluster of calbistrin A was recently identified, the pathway of calbistrin A biosynthesis has largely remained uninvestigated. Herein, we investigated the mechanism by which the backbone structures of calbistrins are formed, by heterologous and in vitro reconstitution of the biosynthesis and a structural biological study. Intriguingly, our analyses revealed that the decalin and polyene portions of calbistrins are synthesized by the single polyketide synthase (PKS) CalA, with the aid of the trans-acting enoylreductase CalK and the trans-acting C-methyltransferase CalH, respectively. We also determined that the esterification of the two polyketide parts is catalyzed by the acyltransferase CalD. Our study has uncovered a novel dual-functional PKS and thus broadened our understanding of how fungi synthesize diverse polyketide natural products.
3. 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.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
