Betaenone A
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| Category | Mycotoxins |
| Catalog number | BBF-00139 |
| CAS | 85269-22-3 |
| Molecular Weight | 366.49 |
| Molecular Formula | C21H34O5 |
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Description
Betaenone A is a biologically active substance produced by Phoma betae PS-13, which inhibits DNA, RNA and protein synthesis. It is a kind of phytotoxin, which can inhibit the growth of the seedlings of Borage and cause chlorosis of the beet leaves.
Specification
| IUPAC Name | (10Z)-12-butan-2-yl-1,4,11-trihydroxy-10-(hydroxymethylidene)-4,6,8,11-tetramethyltricyclo[6.2.2.02,7]dodecan-9-one |
| Canonical SMILES | CCC(C)C1C2(C3C(CC(CC3C(C1(C)O)(C(=CO)C2=O)O)(C)O)C)C |
| InChI | InChI=1S/C21H34O5/c1-7-11(2)16-19(5)15-12(3)8-18(4,24)9-13(15)21(26,20(16,6)25)14(10-22)17(19)23/h10-13,15-16,22,24-26H,7-9H2,1-6H3/b14-10+ |
| InChI Key | FHJXKTOXQHRDTL-GXDHUFHOSA-N |
Properties
| Appearance | White Crystal |
| Boiling Point | 499°C at 760 mmHg |
| Melting Point | 153-155 °C |
| Density | 1.24 g/cm3 |
Reference Reading
1. α,β-Enone Borylation by Bis(Pinacolato)Diboron Catalyzed by Cu3(BTC)2 Using Cesium Carbonate as a Base
Amarajothi Dhakshinamoorthy, Mercedes Alvaro, Abdullah M Asiri, Hermenegildo Garcia Nanomaterials (Basel). 2021 May 25;11(6):1396. doi: 10.3390/nano11061396.
Cu3(BTC)2 (BTC: 1,3,5-benzenetricarboxylate) as a heterogeneous catalyst in the presence of cesium carbonate as a base is reported for the borylation of α,β-conjugated enones by bis(pinacolato)diboron (B2pin2). According to the hot-filtration test, Cu3(BTC)2 is acting as a heterogeneous catalyst. Further, Cu3(BTC)2 exhibits a wide substrate scope and can be reused in consecutive runs, maintaining a crystal structure as evidenced by powder X-ray diffraction (XRD). A suitable mechanism is also proposed for this transformation using Cu3(BTC)2 as catalyst.
2. Total Synthesis of Brasilicardins A and C
Masahiro Anada, Taiki Hanari, Kosuke Kakita, Yasunobu Kurosaki, Kazuki Katsuse, Yuta Sunadoi, Yu Jinushi, Koji Takeda, Shigeki Matsunaga, Shunichi Hashimoto Org Lett. 2017 Oct 20;19(20):5581-5584. doi: 10.1021/acs.orglett.7b02728. Epub 2017 Oct 4.
The first total synthesis of brasilicardins A and C, novel diterpenoid-saccharide-amino acid hybrid metabolites with unique immunosuppressive activity, is described. The key step is a Diels-Alder/reductive angular methylation sequence capitalizing on a trans-fused bicyclic α-cyano-α,β-enone as its precursor to construct the 8,10-dimethyl-trans/syn/trans-perhydrophenanthrene skeleton. Other notable features include an anti-selective aldol reaction, a stereocontrolled glycosylation of a C2 alcohol, and a one-pot, two-step global deprotection sequence that did not damage these sensitive molecules.
3. A polyketide synthase gene cluster associated with the sexual reproductive cycle of the banana pathogen, Pseudocercospora fijiensis
Roslyn D Noar, Elizabeth Thomas, De-Yu Xie, Morgan E Carter, Dongming Ma, Margaret E Daub PLoS One. 2019 Jul 25;14(7):e0220319. doi: 10.1371/journal.pone.0220319. eCollection 2019.
Disease spread of Pseudocercospora fijiensis, causal agent of the black Sigatoka disease of banana, depends on ascospores produced through the sexual reproductive cycle. We used phylogenetic analysis to identify P. fijiensis homologs (PKS8-4 and Hybrid8-3) to the PKS4 polyketide synthases (PKS) from Neurospora crassa and Sordaria macrospora involved in sexual reproduction. These sequences also formed a clade with lovastatin, compactin, and betaenone-producing PKS sequences. Transcriptome analysis showed that both the P. fijiensis Hybrid8-3 and PKS8-4 genes have higher expression in infected leaf tissue compared to in culture. Domain analysis showed that PKS8-4 is more similar than Hybrid8-3 to PKS4. pPKS8-4:GFP transcriptional fusion transformants showed expression of GFP in flask-shaped structures in mycelial cultures as well as in crosses between compatible and incompatible mating types. Confocal microscopy confirmed expression in spermagonia in leaf substomatal cavities, consistent with a role in sexual reproduction. A disruption mutant of pks8-4 retained normal pathogenicity on banana, and no differences were observed in growth, conidial production, and spermagonia production. GC-MS profiling of the mutant and wild type did not identify differences in polyketide metabolites, but did identify changes in saturated fatty acid methyl esters and alkene and alkane derivatives. To our knowledge, this is the first report of a polyketide synthase pathway associated with spermagonia.
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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 ╳
